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Die Mutter meines besten Freundes will mich feminisieren – Crossdressing-Geschichten — Transcript

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0:00Who do you think the woman in the white
0:01dress is? "I asked my older daughter,
0:03Judy. I was showing her photos from an
0:06old family album." That's Aunt Doris,
0:09Mom, "my younger daughter Claire
0:11replied." She looks like her, but she
0:13is not Aunt Doris. "" But there is a
0:16certain resemblance, "I replied with a
0:18smile. I had arranged to meet with my
0:20daughters while their father Simon was
0:22out for his monthly lunch with his
0:24long-time friend Tom. The photo showed
0:28a tall, young woman in a white,
0:29loose-fitting English peasant-style
0:31blouse with a matching knee-length
0:33tiered skirt. A wide red belt
0:36accentuated her slim waist and matched
0:38her shoulder bag. White sandals rounded
0:41off her feminine look. Her blonde hair
0:43was long and curly, very much in the
0:45style made popular at the time by
0:47Stevie Nicks of Fleetwood Mac. She
0:49stood there, one hand on the thin strap
0:52of her shoulder bag. The other held
0:54onto her wide skirt." Mom, are you
0:56wearing the same dress as the woman in
0:58the picture?, "Judy asked curiously."
1:01I've never seen it before and it
1:02actually looks a bit old-fashioned. ""
1:04That's true, the dress is almost 50
1:06years old. I found it in an old
1:09suitcase in the attic. I didn't even
1:11know we still had it. But Mom, take a
1:14look at this photo of you here. The
1:16dress would have been way too big for
1:18you back then. Judy pointed to the
1:20photo next to the picture of the woman
1:21in white. Oh my God! Claire shouted. Is
1:25that Dad? Why do you think that? Claire
1:27flipped back in the album and pointed
1:29to a photo of Simon in his early 20s.
1:31If that's not Auntie, then it can only
1:34be him. Yes, exactly. My daughters,
1:37despite their age and even though Judy
1:39is a mother, were hopping up and down
1:41with excitement. "Mom, you have to tell
1:44us everything!", they shouted in unison
1:46. "Your father is a secret crossdresser
1:49," I quickly added. "He is not gay. We
1:52know all about crossdressers.""Mom,"
1:54Judy said, "you don't have to explain
1:56to us that a man isn't gay just because
1:58he wants to wear a dress. I know that,
2:01honey. But with all the noise from the
2:04anti-woke movement with its populist
2:06politicians and newspapers jumping on
2:08the bandwagon, I wanted to reassure you
2:10that your father isn't like that. This
2:13is all very exciting, but why are you
2:15telling us this only now? Judy asked.
2:18That is a good question and I have my
2:20reasons, but first I will tell you
2:22about Dad and me. We met at a party in
2:26a large student dormitory where your
2:27father also lived. One of the students
2:31was a transvestite. Nowadays, we would
2:33call him a crossdresser. Society became
2:35more liberal. It was the decade after
2:38the wild 60s, and it wasn't unusual to
2:41see a boy dressing openly as a girl. He
2:44often did this himself on the weekends.
2:46Your father had fantasized about it. He
2:49had always worn girl's clothes, but had
2:51kept it a secret. Now he no longer
2:54lived at home, but in a house where one
2:56of his roommates was often dressed as a
2:58girl and accepted by the others. He
3:01decided to come out as a crossdresser.
3:04With the help and encouragement of his
3:06roommate, your father put together a
3:08collection of women's things and
3:09learned to apply makeup and style his
3:11hair. He had shoulder-length hair back
3:13then. When I met him, he was already
3:16very practiced and could easily pass as
3:19a woman." You said you met him at a
3:22party in his student dorm, "Judy said."
3:26Was he dressed up? "" Did you know he
3:28was a man? "" How did you two meet? "
3:31Claire added. Slow down, girls. So many
3:35questions. Yes, he was dressed as a
3:38woman, and no, I didn't know at first.
3:41I was confused when she approached me
3:43with two drinks and offered me one." It
3:46was a white wine spritzer, the first
3:48one I had here, and it's still one of
3:50your favorite drinks, "Claire remarked.
3:53Of course, well, back to the party. I
3:56was fascinated by this young woman.
3:59There was something special about her.
4:01We talked like two women about the men
4:03at the party we didn't find attractive,
4:05or about the women we didn't find
4:07attractive. She wasn't trying to hit on
4:10me. We just chatted animatedly amidst
4:13the bustle of a student party and the
4:15disco music from the stereo. I felt we
4:19would become good friends. After a
4:21while, he finally revealed the truth.
4:24The woman who had brought me a drink
4:27was a man, and I was fascinated. I told
4:30him I wanted to get to know him better.
4:32And we made a date at the student union
4:34cafe. He was to come dressed normally.
4:37And so began a wonderful friendship, a
4:39long marriage, and of course, two
4:41enchanting daughters and a great
4:43grandchild. What was he wearing, though
4:45? Asked Mom Claire, who was always
4:47interested in fashion. It was a black
4:50mini dress with a shimmering wavy
4:52pattern. It had long, wide sleeves, it
4:55was very short, and he was constantly
4:57tugging at the hem every time he sat
5:00down or moved. He wore knee-high boots
5:03with low heels to go with it. Block
5:05heels. High heels were just coming back
5:08into fashion back then. He had long,
5:10straight blonde hair and wore a
5:12headband that matched the dress. He had
5:15applied light makeup and had very dark
5:18eyes. I remember it clearly. But why
5:21have we never seen Dad in a dress? I'm
5:24getting to that, honey. A room became
5:26free in the house where I lived with
5:29other students, and we invited him to
5:31move in with us. He enthusiastically
5:34accepted the invitation. From then on,
5:36he dressed like one of us whenever he
5:38wasn't on campus or doing guy things.
5:41The girls in the house accepted him.
5:43Our friends and visitors only knew him
5:45as a woman, and he simply became one of
5:47us. Then came the day of our graduation
5:51. Your father began a management
5:52training program at a reputable company
5:54in the city. Any suggestion that your
5:57father was a transvestite was
5:58completely out of the question. He got
6:01his hair cut and went to work as a man.
6:04And you know, with a steady income, we
6:06were able to get married and later buy
6:08our first house. Did Dad wear a wedding
6:10dress? Judy asked, giggling. No, of
6:13course not. No one in the family knew
6:16about it, and we had invited some of
6:18Dad's colleagues. He didn't even wear
6:21anything underneath his suit. I was the
6:25only bride. What a shame. I would have
6:27loved to see wedding photos of you both
6:30as brides, said Judy. Maybe the
6:32opportunity will still arise. Well,
6:34something like that. What do you mean?
6:36Judy asked, grinning. I have a plan.
6:40I'll tell you about it later, but first
6:42, I'll answer your question from
6:44earlier. After Judy was born, Dad
6:46packed away his women's things and
6:48never dressed up again. He didn't want
6:51the two of you to be confused or
6:52embarrassed in front of your friends
6:54and others. You know how girls react
6:57when they find out or suspect that your
7:00father is homosexual. He isn't, but to
7:03them, any sign of femininity means a
7:06man is totally gay. And back then,
7:09there was open, widespread hostility
7:11and discrimination against homosexuals,
7:13and an ignorance about transvestism
7:15that still exists today. My so-called
7:18better half is totally against the
7:20wokeness movement and often makes
7:22disparaging remarks about trans people,
7:24but fortunately not within earshot. If
7:26he saw his masculinity being questioned
7:28, I wouldn't know what he would do,
7:30said Claire. I have noticed changes in
7:33Nigel's behavior. He has become much
7:36less tolerant lately. We talked about
7:39having a baby, but I'm not so sure
7:41anymore, I said. I wish for every one
7:44of my children to have a loving father
7:46and a father figure like mine. And now
7:49I understand why my father is so
7:51wonderful and wasn't as distant as the
7:53fathers of so many of my friends. Your
7:55father was ahead of his time. As a
7:59cross-dresser, he could be a father
8:00figure who understood his all-female
8:02family and could empathize with them.
8:05After we got married and before you
8:07were born, your father continued to
8:09wear women's clothing at home. Not all
8:11the time, only when we weren't likely
8:13to have any visitors. The neighbors
8:15never noticed a thing and we
8:17occasionally went out as two women,
8:18just as before. But your father had to
8:22wear a wig now, and we avoided places
8:24where we could be recognized. Society
8:27wasn't ready yet for men to dress as
8:30normal women in public, only for drag
8:32artists on stage or in private clubs.
8:36Your father's reputation and career
8:38were too important to take unnecessary
8:40risks. That is why your father hasn't
8:43worn a dress in the last 40-plus years.
8:45Never, nothing feminine. And it was
8:48perfectly fine for him. Didn't it drive
8:51him crazy not being able to satisfy his
8:53desires? The longing never went away.
8:56He simply neglected his dressing. The
9:00office and we as a family kept him busy
9:02, and he loved you both too much to put
9:04his own desires above your well-being.
9:07Since his retirement, your father has
9:09been sitting at home bored. He worked
9:11hard for his company. He hardly had
9:14time for hobbies or other interests,
9:16just his regular lunch with his old
9:18friend Tom, which luckily he still
9:20keeps up. Society has changed. Dad is
9:24retired and we are no longer children.
9:27Why doesn't he start dressing again? I
9:30told you, I have a plan. He's turning
9:34seventy this year, and I'm giving him
9:36something special. On the day itself, I
9:38want to have lunch here with him. Just
9:40the four of us. And then I'll present
9:42him with his gift. That sounds exciting
9:45. What are you giving him? A diamond
9:47necklace. Both girls looked confused
9:49and then the realization struck them.
9:52Gee, Mom, you want him to start
9:55dressing again? She asked. Then Judi
9:58understood. You're amazing, Mom. I know
10:01, and yes, I want him to start again.
10:05It will be like a hobby for him, and he
10:07can accompany me on activities reserved
10:09for women. You know, in a few years
10:12we'll be celebrating our golden wedding
10:14anniversary. My plan is to prepare him
10:16for that. She should show herself to
10:19everyone, not in a wedding dress, but
10:20dressed for a celebration. I think we
10:23could rent a banquet hall and host a
10:25formal dinner followed by a social
10:27gathering. Just like at a wedding. The
10:31wedding party, that’s when he can
10:32wear the necklace. What if he doesn't
10:35agree? Asked Judi. Always the fighter.
10:39I won't pressure him into anything he
10:41doesn't want. If he doesn't like the
10:43idea, then I'll just have a diamond
10:44necklace for myself. Not that I
10:47wouldn't borrow it from him. Have you
10:49bought the necklace yet? Not yet. Can I
10:51come along?" I’d love to buy him
10:53matching earrings, "said Claire." And
10:56can I buy him a bracelet? ", Judy added
10:59." Mom, did Dad have a girl name? ",
11:02asked Claire." Yes, well, he had one.
11:06His best friend was named Tom. "" You
11:08mean Uncle Tom? ", Claire interrupted."
11:10Yes, Uncle Tom always called your
11:12father Blondie when he was dressed as a
11:14woman. "He looked a bit like Debbie
11:17Harry, the singer from Blondie, who was
11:19very popular back then. I don't know
11:22how it happened, but after a while
11:24everyone called him Debbie. The
11:26birthday, Munja, Simon's special
11:28birthday, is here. I told him our
11:31daughters would come for lunch and he
11:33was pleased. He doesn't like making a
11:36fuss, and lunch with his wife and
11:39daughters means more to him than
11:41partying with others. His alter ego.
11:45Debbie was outgoing and quite the party
11:47girl. I hope the older Debbie will be
11:50just as sociable so I can enjoy the
11:52debut. After lunch, we retreated to the
11:55living room. I handed him a gift. Happy
11:5970th birthday, darling. This is a token
12:04of a new life we can enjoy together. He
12:07looked puzzled as he opened it and a
12:09long, narrow case appeared. When he
12:12opened the case and saw the glittering
12:15necklace, I saw his eyes light up, only
12:17to quickly become confused again. Uh,
12:20thanks. Isn't this meant for you? No,
12:22it's for you. Or rather, for Debbie. I
12:26paused while he processed what I had
12:29just said. Now you are retired. I would
12:32love to see Debbie again. There is no
12:34reason for you to keep her hidden
12:36inside. Debbie never left me, as you
12:39know. But what will our neighbors,
12:41friends, and the rest of the family
12:43think? That remains to be seen. But if
12:46they were to get to know Debby the way
12:48I do, their lives would be enriched. If
12:50not, then it’s their loss. I don’t
12:52understand. Am I supposed to live as
12:54Debby permanently? Oh no, only as you
12:57wish. I love you as my husband and I
13:00don’t want to lose you, Simon. But I
13:02do want Debby to be a part of our lives
13:04again. Girls, did you know about this?
13:07Here is my gift. Dad, please open it.
13:10Begged Claire. He opened it and saw the
13:13diamond earrings. And here is mine,
13:16said Judi. She had bought the matching
13:18bracelet. I think there is something
13:21going on here. So, I assume you are
13:24both in agreement with your mother. Oh
13:26yes, Dad. We think it’s a wonderful
13:29idea, replied Judi. Ever since Mom told
13:33us about Debby, we’ve been dying to
13:35meet her, added Claire. But why
13:38diamonds? Wouldn’t a dress be more
13:40appropriate, if you’re into that? We
13:42planned for you to dress up glamorously
13:45for our golden anniversary. That’s a
13:47high bar to set. I’m not sure if
13:50I’ll be ready to meet everyone. But
13:53you have convinced me. It’s all very
13:55exciting. These are almost the best
13:58birthday gifts I’ve ever received,
14:00even if I have to wait to wear them.
14:03What do you mean by" almost "? I asked.
14:06The best gift is that the three of you
14:08want to meet Debby. I can hardly wait
14:11to dress as a woman again, even if I am
14:14a grandmother now and not the young
14:16woman I was last time." Well, then you
14:19will be a glamorous grandmother, "
14:21laughed Claire. The performance was the
14:23next morning and we were having
14:25breakfast. I had kept the day free. I
14:28planned on going shopping. So, how are
14:31we really going to do this? Asked Simon
14:34. Do what, dear? I teased him. Of
14:38course. You know, getting me some
14:40clothes. The ones we have in storage
14:43wouldn’t fit me anymore. If they’re
14:46even still up there at all. That’s
14:48true. Some items survived and still fit
14:50, but most are too youthful for me. So,
14:53I suggest we go shopping and get you an
14:56outfit. I know your size and your
14:59figure very well. That’s why I can
15:01estimate what I should buy for you. You
15:04used to wear a size 44. I guess
15:06you’re a few sizes larger now, but
15:09considering that manufacturers have
15:11increased their sizing over the decades
15:13. A size 46 should fit. Your shoulders
15:17are equal in width and should be
15:19proportional now. You used to have to
15:22wear size 46 jackets, if I recall
15:24correctly. Yes, that’s right. A size
15:2744 jacket was too tight across the
15:29shoulders. We also need a wig for you.
15:32You can’t grow what you don’t have.
15:35I want my partner to look attractive,
15:38not like a bald old woman. Simon drove
15:41us into town. He’s still the man in
15:44our relationship, but he decided on my
15:46car. Better for shopping, he said. Our
15:50first stop was Marks&Spencer. Where
15:52else? I wanted to buy him a complete
15:55outfit. I knew we would find clothes
15:58and shoes in his size and that they
16:00offer something for all ages. He used
16:03to shop at Amontes often and is still a
16:05regular in the men’s department. So I
16:07knew we would be familiar with the
16:09place. Once we know better what fits
16:12and suits him, I wanted to take him to
16:14specialty stores. Debby’s revival was
16:17my project and I looked forward to
16:19dressing my man like a woman I could be
16:21proud of. First, of course, bras. The
16:25selection of bras is truly overwhelming
16:27. Back when I last bought one, it was
16:31much simpler. How about this one? He
16:34used to only buy white lingerie. He
16:36said it felt virginal and he could wear
16:39matching bras and panties without
16:41breaking his student budget. I thought
16:44black would be more suitable for
16:46starters. Older women who feel young
16:49wear black. Or so I read. Besides, I
16:53like black. I held up a full-coverage
16:55black lace bra. Simon surprised me by
16:59going to another shelf and returning
17:01with a black underwire T-shirt bra with
17:03full cups. What about this one? Well,
17:05this one was exactly the same style I
17:08usually wear. I found it soft,
17:11comfortable, and it gave me good
17:12support. Support and shape. My breasts
17:15are real. Simon’s won’t be, but it
17:18was a good choice. I thought he would
17:21have preferred something girlier.
17:23Anyway, I was flattered that he chose
17:26something I usually wear. Nothing, I
17:30think it would suit me. I almost said
17:33it would suit you. But stopped when a
17:36woman nearby started looking around. I
17:39checked the size. 36C. Was that a lucky
17:43guess or did he know? I put it into the
17:46basket I had picked up on the way in.
17:49Well, for his panties, we bought a pair
17:52that matched the bra. You'll need some
17:55shaping to keep everything in check. I
17:58know you don't get out as much these
18:00days, but you still have a bulge, and
18:03these panties are designed more for
18:05women's comfort than for holding
18:07everything in place. Of course, go
18:10ahead, McDuff. I don't know why he
18:13keeps saying that. I picked out a
18:16high-waisted shaper in black that
18:18should also accentuate the waist. Are
18:22you sure it will work? It doesn't seem
18:25as effective as the girdles I used to
18:27wear. Modern women prefer comfort, and
18:30unnaturally slim waists are not in
18:32fashion these days. Ultimately, it
18:35depends on what you're wearing. You
18:37just have to try it out. You've gone
18:40without comfort for decades. Experience
18:42he needs to catch up on. Okay, let's go
18:45. Now for the pantyhose. You're going
18:48to shave your legs, right? Well, I have
18:51done it before. So why not now? Good,
18:54Sunday. We'll start with some sheer
18:56pantyhose. I grabbed a pack of two
18:59pairs of 20 denier nude pantyhose. In
19:03case he had forgotten how to put them
19:06on, a spare pair could be useful. I
19:09hope, however, that this is not just a
19:11one-time attempt. So, do you want to
19:14wear a dress, a skirt with a top, or
19:17maybe even pants? A dress, please, he
19:20answered firmly. Okay, let's head to
19:23the dresses. We looked at the various
19:25displays. It didn't take long for us to
19:28find a dress that we both liked. It was
19:31a navy blue calf-length wrap dress with
19:33three-quarter sleeves and a tie belt. I
19:37thought the flexible cut and fit would
19:39be good while finding the right
19:41combination of underwear, cut, and size
19:43for a convincing and comfortable look.
19:46I can't wait to try on the dress, he
19:49whispered. This path you're showing me
19:53is so exciting. What about shoes? Or is
19:56it still too early? Not at all.
19:59Naturally, with heels. We went to the
20:01area where the shoes were displayed.
20:04Simon walked straight to the shelf full
20:06of patent pumps. He looked at them and
20:09picked up a pair of black shoes in size
20:1138 with a 7.5 cm heel. How about these?
20:15They go well with the dark blue dress.
20:18But are you sure you want to wear heels
20:20this soon? It must be like riding a
20:23bike. You never forget that, I'm sure
20:25of it. And it will definitely be fun.
20:28What about the size? You're a size 39,
20:30aren't you? Size 38, and they should
20:33fit with pantyhose. I used to wear a
20:37size 37. Besides, these are the largest
20:40they have and they're wide-cut. So, I
20:43think that won't be a problem. If not,
20:46we can just return them. You could sit
20:49down and try them on. I don't think so.
20:52At least not yet. Besides, I don't wear
20:55pantyhose. Why not? I asked, feigning
20:57surprise. When we got home, I finished
21:01a few things I had to do and then
21:03started preparing dinner. Simon went
21:06upstairs with the shopping. Some time
21:09later, he came down in the new clothes
21:12and the heels. He took my breath away.
21:15He still had it. My plan would work. He
21:18had shaved. His whole body, as I later
21:21found out, and his legs looked good in
21:24pantyhose and high heels. I had known
21:26that. The dress suited him perfectly.
21:29The tie belt accentuated his waist and
21:32hips, and the wrap top highlighted his
21:35bust. He had used some of my makeup;
21:38not bad after such a long time and
21:40being unfamiliar with today's cosmetics
21:42. What was noticeable was his thinning
21:45hair. He needs a wig. What do you think
21:48? He did a spin, his skirt swaying back
21:51and forth. I wrapped my arms around him
21:53and gave him a deep kiss. I know that.
21:56I answered his question about lunch
21:58with Tom. Life had settled into a new
22:02routine, but not quite how I had
22:04planned and hoped. Simon spent a lot of
22:07time in the study, on the computer and
22:09the internet. Luckily, he wasn't
22:11watching porn, but educating himself
22:13and learning more about dressing and
22:15acting as a woman. He followed various
22:18tutorials and practiced diligently. He
22:21improved his makeup skills, his sense
22:23of style, and his dress sense for the
22:25modern older woman, and developed a
22:27passable female voice. He ordered
22:29various things online, including a wig.
22:33I had hoped to be able to dress him,
22:34but since that shopping trip, he hasn't
22:36asked me for advice anymore. A kind of
22:40misguided male pride, wanting to prove
22:42to himself that he hadn't lost it. I
22:45don't know, but I'm disappointed that I
22:48can't share it. I wanted to pass on my
22:50experiences to him, not my lifelong
22:52experience as a woman. Once or twice a
22:56week, he would dress up and then listen
22:58to my comments as if a dress could
23:00cover his male pride. I was happy that
23:03I could help him and guide him gently.
23:06I know he's taking it seriously. He
23:08gets his beard removed regularly. His
23:11make-up is more natural now, less
23:13concealing, more feminine. That has
23:16given him more self-confidence. He had
23:18his ears pierced. The diamond earrings,
23:22which were clip-ons, were not. It
23:25hadn't occurred to her and Simon didn't
23:27want to disappoint him. Today Simon is
23:29going out for lunch with Tom as always.
23:31While he was preparing breakfast, I
23:34dressed casually. I didn't have
23:36anything special planned. I thought I
23:38might do some baking. Simon helps out.
23:41He bakes our bread and I bake our cakes
23:43. When I joined him, breakfast was
23:46already on the kitchen table." Are you
23:48going somewhere today? "I asked him
23:50while he poured two cups of freshly
23:53brewed tea." Yes, since it's supposed
23:55to be dry and unusually warm. "Tom had
23:57made a reservation a long way out. A
24:00table on the porch. Oh, very fancy. I
24:04heard they have a new chef and she put
24:06together an incredible menu. If it's
24:09really as good as everyone says, you
24:12absolutely must take me there. We
24:14chatted animatedly while we ate
24:16breakfast. I cleaned up while Tom got
24:19dressed. It was almost noon when I
24:22wondered what was going on with him. He
24:25had to leave soon, then I heard the
24:26clicking of heels on the tiled kitchen
24:29floor. I looked up and caught sight of
24:31this woman. For a moment I was confused
24:33as to who she was and what she was
24:35doing in our kitchen, before I realized
24:37it was Simon. He was wearing a white
24:40floral A-line dress that I didn't
24:42recognize. He had never even hinted
24:45that he would go to lunch with Tom
24:47dressed as a woman. Dressing like that
24:50in public wasn't part of the plan. Not
24:53yet, at least. I quickly composed
24:56myself." Wow, that's a pretty dress. ""
24:59What? This old thing, "he said shyly,
25:02tilted his head, lifted the skirt a
25:04little and spun around once." That's
25:07not old, that's brand new. "I was
25:10disappointed that he had bought the
25:12dress himself. And the white heeled
25:14sandals and the shoulder bag he was
25:16wearing, too." You look okay. "" I
25:19ordered it online and it was delivered
25:21yesterday. "I was a bit worried about
25:24buying it without trying it on, but it
25:26fits perfectly. Looking at you now, I'd
25:29say you can confidently go shopping
25:31when you're dressed up. Although, I
25:34should accompany you to protect you in
25:36the changing room, if there is one."
25:39Would you? That would be great. "I need
25:41to expand my collection. He said need.
25:45What was he thinking? He must have
25:48spent all morning getting ready. I was
25:51surprised that he had plucked his
25:53eyebrows. Before, they looked a bit
25:56androgynous, now he has beautifully
25:58arched feminine brows. I don't know
26:00what he was thinking. What will happen
26:03when he goes out dressed normally? I
26:06suppose he could always use an eyebrow
26:09pencil to restore his original look. Do
26:12you think I look good? I don't want to
26:16embarrass Tom. I want him to be proud
26:19of me. Does Tom know about this, I
26:21asked a bit embarrassed. It was his
26:23idea. It took some persuasion before I
26:26agreed. Now I'm quite excited. I had
26:30told him about the birthday gifts and
26:32that I would be out as a woman again.
26:35And he doesn't mind that you're having
26:36lunch with him like that. Of course. As
26:39I said, it was his idea and he was
26:42thrilled. Reliving old times. Don't
26:46forget, he was my best friend before I
26:48met you. We often went out together or
26:52to parties, where I was dressed as a
26:54girl. Now I am a glamorous pensioner. I
26:57looked at Simon more closely. Glamorous
27:00might not have been the most accurate
27:01description. He wasn't dressed
27:03particularly elegantly, but he was an
27:05attractive man in chic casual wear. Not
27:08old-fashioned like many women our age.
27:11With his fashionable, youthful, yet
27:13age-appropriate style and the recently
27:15acquired, shoulder-length, curly,
27:17straw-blonde wig with bangs, he looked
27:1910 years younger. The top of the dress
27:22clings loosely to his upper body,
27:24accentuating his round breasts and
27:26narrow waist. He was clearly wearing
27:29his new waist belt. The round neckline
27:32and the three-quarter sleeves
27:33underlined the subtle style. The skirt
27:36fell over his hips and flared out to
27:37the middle of his torso. The pattern of
27:40large, yellow, orange, and red flowers
27:42on a white background was striking. He
27:45was only wearing a thin chain bracelet.
27:47I recognized it. It was one he had
27:50bought me a few years ago and the studs
27:52he was now wearing in his pierced ears.
27:56His white sandals had 3-inch block
27:59heels. Nowadays, I would have worn flat
28:02sandals. I probably need to rethink my
28:04style. You look too young to be a
28:07pensioner. That's sweet of you, but
28:10under this dress is a grandfather. At
28:12that moment, we heard a car pull up.
28:15That must be Tom. He said he would pick
28:18me up instead of both of us driving. He
28:21came over and gave me a kiss on the
28:22cheek, not on the mouth as usual. He
28:25probably didn't want to smear his pink
28:27lipstick. See you later, honey." Enjoy
28:32your meal, "I replied, watching him run
28:34out the front door and rush down the
28:36path to his open car. He got into the
28:39SUV. He was all woman, with no trace of
28:42his usual masculine behavior. I
28:45wondered if I’d made a mistake by
28:47letting Tom explore his love for
28:49cross-dressing again. Whatever, I
28:53thought, and turned back to my baking.
28:55It was almost afternoon when I heard
28:58Tom’s car. Usually, Simon is back
29:00after a few hours when he has lunch
29:02with Tom. Simon didn’t get out right
29:05away. They seemed to be deep in
29:07conversation. Then Simon leaned over
29:10and gave Tom a kiss on the lips. Just a
29:12fleeting kiss, but on the lips
29:14nonetheless. My heart sank. I had never
29:17seen them hug before. Let alone be
29:19together. Tenderly. Simon came into the
29:22house feeling upbeat. He hugged me. But
29:25no kiss, not even on the cheek. How was
29:28it? The menu was excellent. Tom and I
29:31are going back again. When are you
29:33taking me? I thought to myself. No, I
29:35mean your first public appearance. Oh,
29:38you mean me as Debby? It was really
29:41nice. Tom treated me like a lady and
29:43complimented me on my dress. Our
29:46conversation wasn't the usual
29:48showboating or talk about our wives.
29:51The staff was courteous and I felt very
29:54comfortable. I’ve come to the
29:56conclusion that I prefer being a mature
29:59woman over the transvestite of my youth
30:01. What about the goodbye kiss you gave
30:04Tom? Mon, isn't that what you do when a
30:08man drives you home after a nice lunch?
30:11Besides, Tom has kissed me before. What
30:14? On the mouth? Yes, that was at a
30:17party before I met you. I was being
30:20harassed by this guy who wouldn't
30:23accept my disinterest. And he started
30:26to get pushy. Tom came to my aid. Help,
30:28by grabbing me and kissing me
30:30passionately on the mouth. I played
30:32along and pretended we were exploring
30:34each other, even though it was just lip
30:37contact. Then Tom let me go, turned to
30:40him, and said with a grin:" Back off,
30:42she's mine. "Funny, as Simon I could
30:45never touch Tom tenderly, let alone
30:47kiss him. But as Debby, it felt
30:49completely natural. So would Debby kiss
30:52a woman? Honestly, I meant it. I didn't
30:56want to mock him. He took me in his
30:58arms, pressed his artificial breasts
31:00against mine, and kissed me
31:02passionately. I couldn't shake the
31:04doubt. Was I benefiting from the
31:06aftereffects of his afternoon with Tom,
31:08or from 50 years with a loving husband?
31:11Never mind. I enjoyed the embrace.
31:14Simon, the woman in black, continued to
31:16go to lunch with Tom regularly, but now
31:19always dressed as a woman. He bought
31:21more dresses online, but wore the white
31:24floral dress several times. Apparently,
31:26Tom liked seeing him in it. My wish was
31:29finally coming true. After his outings
31:32with Tom, Simon felt confident enough
31:34to go shopping with me, just like women
31:36do. I was really looking forward to
31:39contributing to his slowly growing
31:41wardrobe. I really wanted to get him
31:43into skirts and tops for our first
31:45shopping trip. He came downstairs
31:48already dressed in his navy blue wrap
31:50dress. It would be easier to change him
31:53. When he was in the fitting room, his
31:56phone rang. It was Tom. I should answer
32:00it. He went into the study. After about
32:0210 minutes, he came back out,
32:04ashen-faced. I have some sad news.
32:08Audrey had a brain hemorrhage. Tom
32:10called emergency services, but the
32:12paramedics couldn't revive her. He is
32:14completely devastated and desperate. I
32:17can't believe it. She was so full of
32:19life and his everything. What is Tom
32:22supposed to do now? I hadn't had a
32:24chance to ask him about his future yet.
32:28I offered to come over, keep him
32:29company, and help with the arrangements
32:32. He seemed very grateful. I'll change
32:35clothes first. I don't know what to
32:37expect. Simon hurries upstairs. I had
32:40been looking forward to getting more
32:42involved, as I had always intended to.
32:45Now our shopping trip is off and he is
32:47wearing a shirt and chinos again.
32:50Audrey's sudden death is a tragedy and
32:52I know Tom will need all the support of
32:54his best friend. Simon had been gone
32:57for almost the whole day. When the
33:00phone rang, it was him. How is Tom
33:02doing? He is holding up bravely, but
33:05honestly, I think that is because I am
33:07here. We were at the hospital and I
33:09have made an appointment with the
33:11funeral director for tomorrow. Are you
33:13okay? Are you coming along? Yes, of
33:15course. I am staying here for a few
33:17days, otherwise he won't make it
33:18through this. I will come by tomorrow
33:20to pick up a few things. Stay as long
33:23as he needs you. Simon never came to
33:26pick anything up. I assume Tom is
33:28lending him some of his things. We
33:30talked on the phone several times a day
33:33, so I didn't feel left out. He told me
33:36about the funeral arrangements. Dan,
33:38I’m going straight to the crematorium
33:40with Tom. We’ll see you there.
33:42Don’t you need your suit? No, not
33:45necessary. Tom has organized something
33:48for me. I arrived at the crematorium
33:49early. I was dressed traditionally in
33:52black. I wore a form-fitting lace dress
33:55I’ve had for a few years. I saw Tom
33:58outside the entrance talking to a
34:00white-haired woman in black. Simon told
34:03me they didn't expect many mourners, as
34:05Tom and Audrey had lived very
34:06reclusively. Apparently, Simon and
34:10Tom's regular lunches were the only
34:12time they spent apart. Their daughter
34:15and her family had moved to New Zealand
34:17and would attend the service via video
34:20link. Where was Simon? He surely would
34:22have been here with Tom. As I got
34:24closer, I wondered who the woman was.
34:27For a moment, I thought it was Audrey.
34:30She was the same age, maybe she had a
34:33sister. She was tall and slender and
34:35wore a dress with a jacket. The dress
34:38looked like mine, a few years old, but
34:40a classic. The hem of the tight skirt
34:44was shorter than this year's fashion,
34:46revealing well-shaped legs for her age,
34:48encased in sheer black nylon. She wore
34:51four-inch stiletto pumps, very
34:54elegantly. I now regretted choosing
34:58seven-centimeter heels. As I approached
35:02, Tom looked up, waved, and then nodded
35:04to his companion. She turned and smiled
35:07. I was completely stunned. It was
35:10Simon. I greeted Tom with a kiss on the
35:13cheek and the usual, yet heartfelt,
35:15condolences. Then I turned to Simon and
35:18just stared at him. He leaned forward
35:21and initiated the gesture of a faux
35:23kiss that female friends love to use as
35:25a greeting, something we had never done
35:27before. I could see the carefully
35:30applied makeup with the bright red
35:32lipstick. That was not his handiwork.
35:34It was professional makeup. I could
35:37smell the familiar scent of Audrey’s
35:39favorite perfume. As I stepped back, I
35:41noticed the elegant necklace with its
35:44silky sheen of high-quality pearls
35:46standing out against the black. His
35:48dress and the matching pearl earrings.
35:51The dress clung to his figure. I
35:53couldn't quite put my finger on it, but
35:55something was different about him. His
35:58frame looked so natural; he seemed to
36:00have lost weight. The blonde wig was
36:03gone, replaced by a short white haircut
36:05under a black hat with a netting veil
36:07that obscured half his face. He
36:11radiated the timeless elegance of an
36:13ageless, well-dressed woman." Simon, "I
36:16said." I’ll explain later, "he
36:19replied curtly. Tom explained that
36:23Simon had kindly granted my request to
36:25wear Audrei’s clothes, to bring her
36:27memory to life for me and help me get
36:29through the day. Alone, without his
36:32comfort standing in for Odri, I would
36:34have been completely overwhelmed." You
36:37are very lucky, Dian, to have such a
36:39wonderful husband as Simon. "As he
36:41spoke, Audrei’s casket was carried in
36:44. As it was led into the chapel, Simon
36:47took Tom’s arm and they followed
36:48behind it. I was unsure what to do, but
36:52kept my distance. The other mourners
36:55had already taken their seats. Tom and
36:57Simon sat in the front row, and I
36:59slipped into a row further back. Simon
37:03looked back as if expecting me to sit
37:05with him, but he couldn't see me. The
37:08officiant greeted Tom and Debora. It
37:10was as if Simon were the grieving widow
37:13and not Tom, the grieving widower. So
37:15it was Debora, not Debby. Was that Tom
37:18now, or Simon? In the middle of the
37:21service, the officiant announced," And
37:22now, Debora will recite an excerpt from
37:24Audrei’s favorite poem. "Simon stood
37:26up and walked gracefully to the lectern
37:28. I didn't know what to expect, but I
37:31hadn't expected to hear Simon’s
37:33feminine voice in a duet. He read the
37:36lines with so much feeling and strength
37:38, without his normal voice shining
37:40through in the slightest. His
37:43mannerisms were feminine and elegant,
37:46so consistent with the image he
37:48projected; whatever he had done since
37:50his birthday to become the woman
37:52standing there enchanting the mourners,
37:54he had far exceeded my expectations.
37:58That was when I also noticed he was
37:59wearing a gold women's watch and a
38:01four-strand pearl bracelet on his other
38:03wrist. I think I also caught the
38:06sparkle of a diamond ring, but not on
38:08his ring finger, and long, curved
38:10fingernails with a dark polish that
38:12matched his lips. Tears streamed down
38:16my cheeks. Of course, a funeral is an
38:20emotional affair, but the joy that
38:22Simon was realizing his dream, mixed
38:24with the fear of losing my husband,
38:27made me cry. I took a tissue from my
38:30bag and dabbed at my tears. We gathered
38:33in front of the chapel. The mourners
38:35offered their condolences to Tom and
38:37Simon. I don’t know if they knew who
38:40Simon was, but all the women kissed him
38:42lightly, and most of the men gave him a
38:44kiss on the cheek. I stayed back,
38:47hoping to be the last one in line.
38:50Unlike the other mourners, I kissed
38:52Simon on the lips. Dian, said Simon.
38:56I'm driving back with Tom. Would you
38:58drive yourself? I didn't answer. I
39:00wanted him to come along. My silence
39:03was taken as consent. Good, we'll see
39:07you at Tom's. When I arrived, I
39:09couldn't park near Tom's house. When I
39:13finally entered the house, it seemed
39:15everyone else was already there,
39:16enjoying the refreshments. A young girl
39:19was serving food and drinks. Otherwise,
39:22Simon was clearly the host. He was open
39:25and exuberant. Quite different from
39:28when he wasn't with Tom. Usually quiet,
39:31shy, yet polite, he made sure everyone
39:33felt welcome and had everything they
39:36needed. Everyone except me; I needed my
39:39husband, as I hadn't seen him since
39:41that tragic day. Simon had taken off
39:44his jacket, revealing that his
39:46sleeveless dress fit his body perfectly
39:48. Not a young woman's body, of course,
39:51but that of a man our age who took care
39:54of himself. The amazing thing was that
39:57when he was younger, Simon couldn't
39:59wear sleeveless tops or dresses, as his
40:01shoulders and arms were too masculine
40:03for a young woman's. Now, he had
40:06attractive arms that many a woman our
40:09age would have been proud of. As he
40:12aged, his arms had lost the muscle
40:14definition of a younger man. I didn't
40:16know anyone there, only Tom and Simon.
40:19And of course, I knew Odri. I mostly
40:21talked to strangers or sat or stood
40:23alone, listening to the conversations
40:25nearby. You won't be surprised to learn
40:29of the mysterious Debora. Who was she?
40:32Had Tom already found a new partner?
40:35She was clearly his type, as she
40:37resembled Odri in many ways—in dress
40:39and style. Appearance and personality.
40:42At our age, you attend many funerals
40:45when friends and their partners die,
40:47and that means lonely old men. That is
40:50nothing unusual. Today was no different
40:53. I saw men who were visibly taken by
40:56Simon, perhaps hoping to spend their
40:58twilight years with a good-looking
41:00widower. He skillfully deflected their
41:04tentative advances by standing next to
41:06Tom, as if to say he was taken. Was
41:10this a modern version of the trick Tom
41:12used when he kissed Simon at that
41:13student party in the 70s? Or had I
41:16missed something? People began to leave
41:18. I waited to drive Simon home." Hello
41:23darling, "Simon said finally." Thanks
41:26for coming. "" You don't need to thank
41:28me, "I blurted out." Shouldn't Tom be
41:31thanking me, or was Simon still playing
41:33the hostess? "Tom had asked me if I
41:35could help him sort out Audrey's things
41:38. The poor guy had no idea what he was
41:40supposed to do. So, I stayed with him a
41:43little longer. The girl helping him,
41:46Simon—or rather, Debora—came over,
41:48and I felt a bit rejected when he asked
41:51what she wanted. I was annoyed, so I
41:55drove home. Although I spoke to Simon
41:57on the phone several times a day, the
41:59calls were brief, and I still didn't
42:01know what was going on. I decided that
42:04it would be for the best. I wanted to
42:07get my hair done. A little pampering
42:09would do me good. No sooner was I home
42:12than I heard a car pull into the
42:13driveway. I looked out the window. It
42:16was Tom's SUV. I expected Simon to come
42:20in himself, but then the doorbell rang.
42:23I opened the door and there stood Simon
42:25. He was dressed as a woman. He wore a
42:28light green cashmere sweater, a tweed
42:31A-line skirt, and brown ankle boots
42:33with high, sturdy heels. He still had
42:36the short white wig and the improved
42:38makeup I’d last seen on him. He wore
42:41a different lady's watch with a thin
42:43brown leather strap, a thin gold chain
42:45bracelet, and small gold earrings. And
42:48I could now see that the ring was
42:50indeed a diamond ring, larger than my
42:53engagement ring, with a diamond
42:55surrounded by several smaller ones. I
42:58smelled the same scent as at the
43:00funeral. I couldn't recognize a trace
43:02of Simon, except for the familiar
43:04features behind the feminine makeup."
43:07Hi, Diane, "he said, leaning in to kiss
43:10me on the lips. Better than an air kiss
43:13or a quick peck on the cheek, and
43:14exactly what we would do for a greeting
43:16." Tom and I brought some of Audrey's
43:19things over. "" I'm just going to help
43:21Tom. "Take them out of the car and
43:23bring them into the guest room.
43:25Together, they carried an seemingly
43:27endless parade of suitcases, garment
43:29bags, and boxes. I noticed that Tom
43:31carried the larger ones and Simon the
43:33smaller ones. Tom had everything firmly
43:36under control." That's everything. "" I
43:38hope you're happy with this, Simon. ""
43:41Good to see you again, Diane, but I
43:43have to go before I change my mind. "I
43:46wondered what he meant by that. He gave
43:49me a quick hug and a kiss on the cheek.
43:52Then he turned to Simon." You were a
43:54wonderful friend. "" Simon, I don't
43:57know what I would have done without
43:59your help and your company. "" Come
44:01here. "They hugged each other tightly
44:03and finally pulled away with a kiss on
44:05the lips. No lingering one. I was
44:07relieved. I was also relieved to
44:10realize that Simon had actually come
44:13home." Come on, darling, "Simon said,
44:16taking my hand." I have a lot to tell
44:18you, and I have made a decision. We
44:21need to talk, Debora. I had only cooked
44:24for one, but Simon said he was on a
44:26diet and would be satisfied with a
44:28light meal. I wasn't particularly
44:31hungry, so I shared my food with him.
44:34While we ate, we talked. Tom is saying
44:37all these things now. Audrey's things
44:39were in the guest room, I said. Yes,
44:42exactly. We went through her things.
44:45Most are still wearable, or in the case
44:47of the cosmetics, let's say still
44:50usable. They are here now. Why? I don't
44:53quite understand that. What are we
44:55supposed to do with them? Do you
44:57remember the outfit I wore to the
44:59funeral? Yes, you looked elegant.
45:02Everything suited you perfectly and it
45:04was of good quality. Well, those were
45:07her things, just like what I am wearing
45:09now. It turns out that Audrey and I are
45:12the same size. I can wear her clothes.
45:16I thought she was slimmer than you. But
45:18she wasn't. When necessary, she wore a
45:21corset. In order to wear her clothes, I
45:24wear one too. No wonder you look
45:27slimmer. Are you wearing her corset now
45:29? No, I'm wearing a waist cincher. All
45:32her waist cinchers and corsets are
45:34boned. She was old-fashioned, and her
45:36appearance was important to her. My
45:38appearance is important to me, and they
45:41give my figure a good foundation. So
45:43you are saying that the clothes
45:44upstairs belong to you now. Yes,
45:47exactly. I have a complete wardrobe for
45:49all seasons and occasions for a woman
45:52of my age and status. And like the
45:54mourning dress and the jacket, they are
45:56all of good quality. Seeing how much
45:59you both brought and knowing Audrey's
46:01love for shopping and fashion, you now
46:03have a larger closet than I do. True,
46:06but there are also things we can share,
46:08like jewelry, bags, and scarves. So,
46:11what are you doing? I am already doing
46:14it. Since the first day with you, I
46:15have been wearing her things and will
46:17continue to do so. From now on, I am
46:19Debora. Only for Tom, you, and our
46:22daughters am I Simon, regardless of my
46:24official identity. Tomorrow I will go
46:27through my old clothes. I'll set aside
46:30a few pieces for emergencies and the
46:32rest will go to charity or recycling. I
46:35need room for my new things. Everything
46:38of Odri's that I don't expect to wear
46:40or that doesn't fit me will also go to
46:43charity. There is a second-hand shop
46:45here in town with high-quality clothes.
46:47You should take them there. They can
46:50raise more money than the other thrift
46:52stores. Good idea, but it's getting
46:55late. I've packed a kind of travel bag
46:57with sleepwear and an outfit for
46:59tomorrow. I'll get it and then come to
47:02your bedroom. May I have a say before
47:04you leave? Future. Our future. Simon
47:09looked surprised, but his expression
47:11quickly shifted into shock and then
47:13into guilt. The guilt of a person who
47:16has unintentionally hurt their loved
47:18one. He put his arm around me. I'm
47:21sorry, my dear. I was being selfish and
47:24only thought of myself. I will do
47:26anything you want. Back to my life as
47:29Simon. It's not too late yet. I just
47:32need time to cover my tracks. I only
47:35want what you want. I'm happy that you
47:38are the woman you want to be, as long
47:40as you remain my husband. It just hurts
47:43me that you didn't ask me beforehand,
47:45even if it doesn't contradict what
47:46happened in my plan for Simon.
47:49Full-time crossdressing shouldn't
47:50happen so quickly, if at all, and
47:52certainly not before coming out on our
47:54wedding anniversary. I will involve you
47:57in the future. We will continue this
48:00adventure together. Simon was in the
48:02bathroom when I came upstairs. When he
48:05came out, he was wearing a sheer
48:07nightgown. It was the first time I saw
48:10him in women's sleepwear. I would have
48:12imagined something like that for Odri.
48:14It was sheer, black, floor-length, and
48:17gathered below his chest. Or where it
48:20would be if he had one. He had one,
48:22trimmed with lace and with wide straps.
48:25It floated with every step. He seemed
48:28so much more feminine than I did. I
48:30felt a tingle in my stomach. Maybe my
48:32plan is more for me than for Simon. But
48:35there was something else. Darling,
48:37you're still wearing your wig. It's
48:40actually made of a mix of my own hair
48:42and hairpieces, attached to a net over
48:45my scalp and dyed to match my natural
48:47white. As my own hair grows longer, the
48:50pieces are lengthened or thinned
48:52accordingly, so it looks like I have a
48:54full head of hair. It's firmly attached
48:57and I can only have it removed at the
48:58hairdresser's. Do you like the style?
49:01Yes, I think the shorter cut looks
49:03better than the wig you bought, and
49:05your white hair looks more natural and
49:08is quite striking. I like it. I'm glad
49:11to hear that, because I want to keep it
49:13this way. But it’s one of the reasons
49:15, along with my longer nails and shaped
49:17eyebrows, why it’s harder to slip
49:19into Simon spontaneously or switch back
49:22and forth between the two. That, and
49:24the irresistible appeal of Audrey's
49:26wonderful wardrobe. We agree on that,
49:29even though it’s not my style. Two
49:31unknown creams were lined up. Simon
49:34must have adopted Audrey’s beauty
49:36rituals as his own. I got ready and
49:39joined him in bed. With increasing age,
49:42our sex life had become less intense.
49:45It was more about pleasing each other
49:47and feeling close. I wasn't sure if it
49:50was his absence from our marital bed or
49:52his ultra-feminine nightgown, but Simon
49:54was more sensual, more feminine that
49:56evening. I loved it. I loved having him
50:00back home. I had gotten up before him
50:03and went downstairs to make breakfast.
50:05He joined me shortly thereafter.
50:07Another surprise. He was wearing a
50:10matching negligee over his nightgown
50:12and embellished mules with kitten heels
50:14. He wasn't wearing makeup, but with
50:16his new hairstyle, shaped eyebrows, and
50:18stud earrings—not to mention that he
50:20no longer had a beard—he could have
50:22passed for a woman, and his facial
50:24features seemed quite feminine in that
50:26outfit. That was when I realized that
50:29Simon was enjoying Audrey’s clothes
50:30to the fullest. He had intentionally
50:32set aside the negligee and nightgown
50:34for the previous night. Whether it was
50:37intentional or he was simply taking
50:38advantage of the new opportunity
50:40presented to him, Audrey has become his
50:41role model, hasn't she? And her style
50:44was certainly a feminine mix of modern
50:46classic and old school. If so, Deborah
50:49will probably be quite demanding, but
50:51fortunately, our pensions are more than
50:53enough. Are you still in the mood to
50:56sort through your closets? I can hardly
50:58wait to show you my new things. I went
51:02through them at Tom’s and took the
51:04items I know I’ll wear, and that was
51:06almost everything. The rest went to
51:09charity. Hardly anything was recycled.
51:12Audrey bought quality and took good
51:14care of it. I’m going upstairs now to
51:16get changed. An hour later, Simon
51:19reappeared in a skirt and blouse, some
51:21jewelry, and high heels. He had applied
51:24his makeup skillfully, so his face now
51:26looked feminine and matched the rest of
51:28his appearance. He will undoubtedly
51:31pass as a woman. His fitted
51:33long-sleeved blouse was made of royal
51:35blue silk and featured a collar and
51:37buttons. His black A-line skirt was
51:40knee-length, and he wore sheer black
51:42pantyhose and black pumps. He looked
51:45like he was heading to the office, not
51:47like he was staying home. You look
51:49overdressed, darling. And why high
51:52heels? You’ll be on your feet all day
51:55. Audrey was always elegantly dressed.
51:58Casual wear was out of the question for
52:00her. All of her shoes had heels. Three
52:03inches was standard. All the time I
52:06spent with her, Tom, I wore her fancy
52:09dresses and high heels. Even while
52:11sorting through her things, Tom liked
52:14that I dressed like her, and I got used
52:16to it and liked it. Simon seemed
52:19thoughtful for a moment before he
52:21continued. Sorry, I like getting advice
52:24from you on what to wear and how I look
52:26. We were just about to go shopping
52:28when Tom called. How about tomorrow?
52:32Simon just earned some brownie points.
52:34For now, wear what you have. I always
52:37admired Audrey, but she had a different
52:39style than you. Let’s see how your
52:42personality and style develop as
52:45Deborah. If you need something more
52:47practical or something that fits your
52:49own style better, we can go shopping.
52:52In the meantime, I know you will enjoy
52:54wearing the whole ensemble. It took all
52:57day, but we finally put together his
53:00new outfits. I was surprised and proud
53:02that Simon didn’t take off his high
53:04heels when we were finished. He just
53:07wore them for the rest of the evening.
53:10We decided to pack all of his men’s
53:11clothing into the boxes we had unpacked
53:13Audrey’s clothes from and store them
53:15in the attic for now. I wondered how
53:19long they would remain there
53:20undisturbed. There simply wasn’t
53:22enough space. His new collection is in
53:25our bedroom, so the guest room is
53:27becoming the overflow. Maybe I’ll
53:30store a few of my things in there too.
53:32It’s only fair to give him more space
53:34in our bedroom. I have to say, now I
53:37see that he has many beautiful dresses
53:39and elegant accessories. He won’t be
53:42lacking anything. I’ve decided that
53:44everything should belong to him. The
53:46designer bags, the exquisite jewelry,
53:48and so on. Audrey had excellent,
53:51expensive taste and a generous husband.
53:54I’ve been thinking about the evening
53:56gowns and cocktail dresses. Many were
53:59low-cut, but it would be a shame to
54:01give them away already. There are
54:03surely ways for him to be able to wear
54:05them. It was time to introduce the
54:08girls to the new Deborah. The girls
54:11knew everything about their father's
54:13progress and his unexpected happiness
54:15and couldn't wait to see him as Deborah
54:17. I wanted it to be special,
54:20introducing the girls to the new woman
54:22their father had become. So, I reserved
54:26a table at a restaurant with a strict
54:28dress code. We all had to dress up. I
54:31didn't know how the husbands would
54:34react, especially Nigel with his newly
54:37acquired anti-woke views. In the end,
54:40it didn't matter. Claire didn't say
54:43anything. Nigel and Harry were away on
54:45business. Simon seemed nervous. Don't
54:48worry, darling. The girls will be here
54:50soon. They are going to love you. You
54:53look stunning. I saw a look of surprise
54:55in his eyes. I looked up and saw our
54:58two daughters with wide grins, rushing
55:00toward our table. They both hugged
55:03Simon. Claire first. Simon’s
55:06nervousness vanished and a broad grin
55:08appeared on his face, too. I had kept
55:12them up to date via our WhatsApp group
55:14chat, including photos. We called him
55:17Aunt Deborah. That’s what we wanted
55:19to call Dad in public. Debbie didn't do
55:21Simon justice. He had to be Deborah, as
55:24he and Thomas had apparently already
55:26decided. We liked the upgrade and it
55:28was definitely better than Blondie. "
55:31Dad, or should I say, Aunt Deborah, you
55:34look fantastic!" shouted an excited
55:37Claire as she sat down. Simon looked at
55:39me inquiringly. I suggested they call
55:42you Aunt in public. They can hardly
55:44call you that within earshot of others.
55:47To others, you are now the matriarch of
55:49this family and them and their Aunt
55:51Deborah, he mused. I like that, but I
55:54will always be your you-know-what.
55:56Invitation to Abel. I heard Tom's car
55:59outside when he dropped Simon off after
56:01one of their lunches together. Simon
56:04said that Tom, now that he's alone,
56:06looks forward to his company even more.
56:10He makes a special effort to look good
56:12and carefully selects the dresses from
56:14Audrey that Tom likes to see him in.
56:17Today he's wearing one of the older
56:18dresses from the collection. It looked
56:21very similar to a Laura Ashley dress I
56:24had in the 80s. It was made of sturdy,
56:26high-quality cotton fabric with a
56:28beautiful print of red roses on a
56:30purple background. It had a very full
56:33skirt with lots of fabric, a sweetheart
56:35neckline, and short, puffy sleeves with
56:37bows. The cut was fitted with a flared
56:41skirt and a deep square back neckline.
56:44Did you like it, darling? What did Tom
56:46think of the outfit? He was thrilled.
56:49Apparently, it's a real Laura Ashley
56:51dress from the 80s. I remember you had
56:54one very similar, but yours was light
56:57green. It is very comfortable to wear.
56:59I’m glad that I have one now, too. So
57:02nostalgic. I also once had a light
57:05green one in a similar style. I’m
57:07impressed that you remember that. Yours
57:10was much smaller than mine. Oh yes,
57:13I’m a crossdresser, darling. I could
57:15be wrong. Although I’ve been
57:17interested in fashion for a long time,
57:19I’ve always been into women's fashion
57:22and your style. I know you were a
57:24wonderful shopping companion. We had a
57:27delicious lunch and lively
57:29conversations. I enjoy Tom’s company
57:31more than ever. He told me he bought
57:35this vintage dress for Audrey’s
57:37birthday and loved seeing her in it.
57:41Simon lifted the skirt and spun me
57:43around briefly. Careful, darling,
57:45you’re not as young as you used to be
57:48and are wearing high heels. Yes,
57:50you’re right. I think I overdid it a
57:53bit. I’ll sit down. Come here. I have
57:56to tell you something. Go into the
57:58living room. I’ll make us some tea. I
58:00brought in two cups of tea and sat down
58:03opposite Simon. Thank you. Simon took a
58:06sip. Tom is a member of a society that
58:09hosts an annual ball, and he and Audrey
58:11attend it regularly. It was the
58:14highlight of their year. Tom had bought
58:16tickets for this year’s ball, and she
58:19had received the dress she ordered
58:21shortly before she died. She had also
58:24bought shoes and a clutch to match the
58:25dress. The dress, shoes, and bag are
58:28mine now. That must be a disappointment
58:31for Tom. Can he get his money back? No,
58:34it’s not that simple. It’s a
58:37complete package, including a hotel
58:39stay where the ball will take place.
58:41But I don’t want to talk about that.
58:44The dress is low-cut and I don’t have
58:46the figure for it. Perhaps you could
58:49wear something over it to cover up or
58:51choose a different dress. How could
58:54this happen? Did I just agree to my
58:56husband going away with Tom and
58:58attending a ball? I’ve been thinking
59:01about getting breast implants for some
59:03time now. I would feel and look more
59:06natural, and then I could finally wear
59:08all my dresses and tops. I have so many
59:11great things that I unfortunately
59:13cannot wear. As you know, I am a huge
59:15fan of Audrey’s clothes. There is
59:18something about the style that gives me
59:20comfort and joy. Simon paused as if he
59:23were thinking. I am happy with my
59:25gender and have no intention of
59:27changing it. But now I want to live as
59:30a woman. I feel like a woman now and,
59:32with your support, I want to live as
59:34one permanently. He paused again, as if
59:37he needed to gather his courage. I see
59:40no reason anymore why I shouldn't have
59:42my own breasts to feel like a woman and
59:44be perceived as one. I wanted you to
59:48enjoy your retirement and thought that
59:50taking up your crossdressing passion
59:52again would be something we could both
59:54enjoy. Enjoy it. I wanted it to be open
59:59, not just confined to the bedroom, and
1:00:01to use our golden anniversary to, as
1:00:04they say, introduce you to our friends
1:00:07and family. What happened next exceeded
1:00:11my wildest dreams. I know you too well.
1:00:14You are not going back. I don't want to
1:00:16either. I love my new life. It's almost
1:00:19as if a dam had broken and a flood of
1:00:21joy had been released. I am enjoying a
1:00:24retirement that exceeds my wildest
1:00:26dreams, and breasts would make it
1:00:28perfect. Once you have your breasts, do
1:00:31you want to take it a step further? No,
1:00:34I am happy keeping my male sexuality.
1:00:38Even though I am over 70 now, I can
1:00:40still keep up. I enjoy our lovemaking
1:00:43and breasts would only enhance it. I
1:00:45have researched hormone therapy.
1:00:49Apparently, I am too old for female
1:00:50hormones, and even if I weren't, I
1:00:52wouldn't want to wait for my breasts to
1:00:54grow. I don't have time for that.
1:00:57Besides, I don't want to lose my libido
1:00:59prematurely. That's why I am opting for
1:01:01implants, and I still have enough time
1:01:03before the ball. I never told Simon my
1:01:06thoughts, and he never asked for my
1:01:09consent, but I assume my silence was
1:01:11taken as agreement. He had the
1:01:14procedure done and is very proud of his
1:01:16new breasts. Audrey wore a size 36B bra
1:01:19. Simon had had the padding reduced so
1:01:23he could wear her bras and dresses. It
1:01:26really suited him. Larger breasts just
1:01:29looked too bulky on his male torso. The
1:01:32enhanced breasts created by the surgeon
1:01:34fit Audrey's figure and her bras
1:01:36perfectly and looked excellent on Simon
1:01:38. I am glad he didn't want to lose his
1:01:41masculinity. It still gave me pleasure,
1:01:44and I agree with him. His breasts were
1:01:47a wonderful bonus. I loved caressing
1:01:50and kissing them. He did not show off
1:01:52his new breasts. He continued to dress
1:01:55discreetly and appropriately. He could
1:01:58now wear dresses and tops that showed
1:02:00his cleavage or were low-cut. Audrey
1:02:03had class, which had rubbed off on
1:02:05Simon. Never provocatively sexy, just
1:02:08tasteful and revealing. The day of the
1:02:11boat had arrived. I had never seen the
1:02:13dress before she left, but Simon had
1:02:15mentioned it was gold. Tom arrived
1:02:18early, but Simon was ready long before
1:02:20that and had everything packed. But he
1:02:22did what women just do. He made Tom
1:02:25wait, although I had already been
1:02:27making Simon wait for years myself. I
1:02:29don’t mean waiting for years, just a
1:02:31few minutes every time. Spread out over
1:02:34years, of course. For the trip, he wore
1:02:36a flowing midi dress. It was black with
1:02:39small dots and sheer. It had long
1:02:42sleeves and a tie-neck collar. A thin
1:02:44black leather belt accentuated his
1:02:46waist. Underneath, he wore a short
1:02:49black slip dress. You could see the
1:02:51contours of his décolleté. He wore a
1:02:54short black blazer, knee-high heeled
1:02:56boots, and his usual gold watch and
1:02:59bracelet. His makeup was perfect as
1:03:02always, but they left in time for a
1:03:03hair and beauty appointment at the
1:03:05hotel salon to get him ready for the
1:03:07ball. The appointment had originally
1:03:10been for Audrey. Both Tom and Simon
1:03:12gave me a kiss on the cheek. Tom packed
1:03:15the garment bag with the ball gown and
1:03:17a large suitcase for just one night. I
1:03:19watched them drive away, thinking that
1:03:21maybe he didn't want to show much
1:03:23affection in front of Tom. The sex last
1:03:26night had been great. One of our best
1:03:29in years. So, the casual goodbye didn't
1:03:32bother me. Then a thought occurred to
1:03:34me. Was last night a goodbye? No,
1:03:37that’s nonsense. It was around 11
1:03:40p.m. when my phone rang. It beeped. I
1:03:43had a message from Simon. A photo of
1:03:46Tom and Simon. No text. Tom looked
1:03:49stunning in his tuxedo and black tie.
1:03:52He had his arm around Simon’s waist,
1:03:54who looked radiant. I became jealous.
1:03:58Was it because of the dress, or that
1:04:00Simon was clearly enjoying himself in
1:04:02Tom’s company at the ball? He looked
1:04:04at him as if to say, "This is my man."
1:04:07If so, why send me the photo tonight?
1:04:10Simon’s pose reflected him as a
1:04:12confident, timeless, attractive, and
1:04:15elegant woman. Any man would be proud
1:04:18to have her as a partner. And tonight,
1:04:20Tom seemed to be exactly that man, and
1:04:22that should surprise no one. He, my
1:04:25husband, looked sensational. His hair
1:04:28was curled and put up. His own hair was
1:04:31long enough to show off his dangling,
1:04:34sparkling earrings. Though not the ones
1:04:36Claire had given her father. His makeup
1:04:39matched the dress and the occasion
1:04:41perfectly. It brought out his best, and
1:04:44there was no hint of the Simon
1:04:46underneath. Unless you knew him. The
1:04:49tight bodice of his dress sparkled with
1:04:51golden sequins. His youthful, firm
1:04:54breasts nestled into the cups of the
1:04:56bodice. No wonder he wanted his breasts
1:04:59. The skirt was also golden and
1:05:01shimmering, though that was hard to see
1:05:04in the photo. It clung to his hips and
1:05:06then fell wide over him onto the floor.
1:05:09His shoes couldn't be seen, but judging
1:05:12by his height, he was definitely
1:05:14wearing very high heels. He was wearing
1:05:17a necklace and a bracelet. Obviously a
1:05:19set matching the earrings. They
1:05:22sparkled. I hadn't seen them in his
1:05:24jewelry box, but if they belonged to
1:05:26Audrey, they were surely high-quality
1:05:28diamonds. They were elegant, and the
1:05:31necklace drew the eye to his breasts.
1:05:35His hands with the long red nails
1:05:36clutched a small evening bag that
1:05:38matched his top in color. Did Simon
1:05:41want to share the moment with me or
1:05:42tell me something? I am quite sure that
1:05:45everything was completely harmless. It
1:05:47was late in the evening the day after
1:05:49the ball when I heard Tom's SUV turn
1:05:51into the driveway. I resisted the
1:05:54temptation to run and open the front
1:05:56door and decided to wait until Simon
1:05:58had gotten out and sought me out. I
1:06:01wasn't making it easy for him. I sat in
1:06:03the dark living room. I was annoyed
1:06:06that he was so calm and hadn't told me
1:06:08anything about it. I heard the front
1:06:10door open and muffled voices, followed
1:06:12by the clacking of Simon's heels on the
1:06:14wooden floor. He and I both knew that
1:06:17Tom would be with him as we moved from
1:06:19the hallway into the living room. There
1:06:21was laughter, glasses clinking, and
1:06:23there were moments of silence again and
1:06:25again. An hour later they were back in
1:06:28the hallway and I heard the front door
1:06:30open. Voices could be heard and I could
1:06:32hear Simon say that he had had a
1:06:34wonderful time and that he would never
1:06:36forget his wife. That was a shock.
1:06:39There was silence again before I heard
1:06:41the front door close and Simon went
1:06:43upstairs and entered our bedroom. I am
1:06:46sure that nothing bad had happened and
1:06:48being his wife must be some kind of
1:06:51inside joke. I heard him call "Diane,"
1:06:54but I didn't answer. I heard him
1:06:56walking around the house, obviously
1:06:58looking for me. The door to the study
1:07:01opened. I saw his silhouette against
1:07:04the light falling in from the hallway.
1:07:07The light gave away my presence. I
1:07:09could see that he was wearing a dress
1:07:11with a short jacket. I think it was
1:07:14purple. In the bright light behind it,
1:07:17it was hard to tell. He wore his hair
1:07:19in his usual chic bob, which now
1:07:21reached his shoulders. Darling, why are
1:07:24you sitting in the dark? I was waiting
1:07:27for you. Where were you? Were you there
1:07:29already? I was expecting you for lunch.
1:07:32I had a wonderful day, but I'm very
1:07:35tired. I’m going to bed now. He
1:07:38turned around, his skirt swirling, and
1:07:40went upstairs. I was sad that he didn't
1:07:43want to talk, even though I had been
1:07:45alone all weekend and he apparently had
1:07:47a great time with Tom. I followed him
1:07:50to bed. We never talked about the
1:07:52weekend. Tom, A and D, Debora, Tom and
1:07:55I are invited to a dinner party next
1:07:58week. Sorry, what was that? I asked
1:08:01Simon. Dinner party. A couple invited
1:08:04Tom and me to dinner. There will be
1:08:06other guests there, as the guy finally
1:08:09wants Tom to move on with his life. Not
1:08:11that he misses Odrien Tag and would
1:08:13have accepted the invitation. I had to
1:08:16think about it. Having lunch with them
1:08:19regularly is one thing, but going out
1:08:21with Tom as a woman and other people we
1:08:24don't know is something else entirely.
1:08:27On the other hand, I set Simon on this
1:08:29path and Tom is his best friend, so
1:08:31it's probably just a natural
1:08:33development. It just wasn't part of my
1:08:36plan. I still do my own thing and I
1:08:39should let Simon do his. After all, he
1:08:42just wasted his time at home until I
1:08:44encouraged him to dress as a woman more
1:08:46often again. I just had it in the back
1:08:49of my mind that as a crossdresser he
1:08:51would only find new friends after he
1:08:53had come out to our anniversary party,
1:08:55the rest of the family and our existing
1:08:57friends. That's nice, darling. When is
1:09:00it? Next Saturday night. Then I can
1:09:04finally wear a low-cut cocktail dress,
1:09:06now that I have breasts. Simon returned
1:09:09from the hairdresser late Saturday
1:09:11afternoon with a new, longer hairstyle.
1:09:14His own hair had grown longer and a
1:09:16revision of the extensions was long
1:09:18overdue, a more voluminous bob that
1:09:20curled at the neck. He had his nails
1:09:23done and had been styled for the
1:09:25evening. What do you think? Would Tom
1:09:28be proud of me? The hairstyle really
1:09:30suits you. Really? Absolutely. I have
1:09:33never seen him so naturally feminine. I
1:09:35don't know how Tom feels, but I was
1:09:38proud of him. Get ready, otherwise
1:09:40you'll keep Tom waiting. Later, Simon
1:09:43came down in a very glamorous red midi
1:09:45dress. It must have been one of Audri's
1:09:48newer dresses, as it was fashionably
1:09:50cut longer than many of her other
1:09:51dresses. It had a tight-fitting,
1:09:55sequin-covered bodice. Like her ball
1:09:58gown, this style must also have been
1:10:00Audrey's favorite. Short fluttering
1:10:02sleeves and a V-neck that showed a deep
1:10:05yet subtle décolletage. In contrast to
1:10:08the bodice, the softly gathered
1:10:10Talamidi skirt fell gently from the
1:10:11waist. She had chosen sheer black
1:10:14pantyhose, strappy stilettos with 10-
1:10:17centimeter heels, and a black sequined
1:10:19clutch. Apparently, Audrey had a shoe
1:10:22collection perfectly suited for special
1:10:24occasions, and she and Simon both loved
1:10:26wearing high heels. Good for them. The
1:10:29surprise for me was that he was wearing
1:10:32the same diamond necklace I had seen in
1:10:34the photo from the ball. I don't
1:10:36remember this necklace when we went
1:10:38through Audrey's jewelry. No, you
1:10:40wouldn't have. Tom gave it to me. He
1:10:43had planned to buy it for Audrey and
1:10:45give it to her as a surprise at the
1:10:47ball. When I agreed to accompany him to
1:10:51the ball, he was so happy that he
1:10:52bought me the necklace he had intended
1:10:55for Audrey as a thank you. I wore it
1:10:58tonight to show my appreciation. It
1:11:02really suits you, and I must say, I
1:11:04have never seen you look so stunning.
1:11:06Tom will be very proud. Thank you,
1:11:09darling. I hope you don't mind that I'm
1:11:12wearing Tom's necklace and not the one
1:11:15you gave me. Yours is truly beautiful.
1:11:18It is something special, and I am
1:11:20saving it for our anniversary, when my
1:11:22relatives and friends will meet me as
1:11:24Deborah for the first time. Simon knows
1:11:27when to say the right thing. The
1:11:29doorbell rang. That must be Tom. Don't
1:11:33wait up for me. Have fun. We gave each
1:11:36other an air kiss so as not to ruin his
1:11:38flawless makeup. I could smell that he
1:11:41was wearing the same scent as he did at
1:11:42Audrey's funeral. I will, he said,
1:11:45walking to the door. His heels clicked,
1:11:48his skirt swished. After that dinner
1:11:51party, Tom and Simon must have been
1:11:52included in a larger circle of friends.
1:11:55Simon was now going out with Tom much
1:11:57more often than just for their usual
1:11:58lunches, and he was always well dressed
1:12:00. Although it was part of my plan for
1:12:03Simon to go out, I had expected to be
1:12:06more involved. I suppose if I were to
1:12:09join them, it would be confusing and I
1:12:11would be the outsider. Simon, me, and
1:12:14then one day, maybe Simon would finally
1:12:17realize that I, too, would enjoy his
1:12:19company in public and not just at home.
1:12:22Don't get me wrong. We enjoyed our life
1:12:25together as two women and as a married
1:12:27couple, but it always took place only
1:12:29at home or while shopping at the
1:12:31supermarket. We saw our daughters, but
1:12:33for the time being, neither their
1:12:35husbands nor our granddaughter knew
1:12:37anything about Simon's new life. Dian,
1:12:39you said if it was any good, you wanted
1:12:42to try out the pub that Tom and I went
1:12:44to. You know, the one with the new menu
1:12:47. That must have been months ago. Yes,
1:12:50I remember. Was it good? It was
1:12:53excellent. Tom and I enjoyed it very
1:12:55much. I thought, I don't have any plans
1:12:58today. Would you like to go there for
1:13:00lunch? Yes, I'd love to. I'll go change
1:13:03quickly. I wore white ankle-length
1:13:06pants and a white long-sleeve shirt
1:13:08with horizontal blue stripes. Pretty
1:13:11chic, but too casual for Simon. He was
1:13:14already wearing a black, straight,
1:13:16knee-length skirt with an ivory blouse
1:13:18that showed a bit of cleavage, and his
1:13:20usual stilettos. I decided on a
1:13:24straight red wool dress. It wasn't too
1:13:27tight. It looked good on me because it
1:13:29didn't emphasize my figure. I am not
1:13:31overweight like many women my age, but
1:13:34I have lost my youthful figure. Maybe I
1:13:37should take an example from Odri and
1:13:39Simon and get myself a Mida or Cette,
1:13:41like my mother used to wear. I wore my
1:13:44unfamiliar stilettos. I didn't want to
1:13:47be overshadowed by my husband. When I
1:13:50came downstairs, Simon had put on an
1:13:52ivory dress. His jacket matched his
1:13:55blouse perfectly. It was fastened with
1:13:58a single button and had a narrow waist.
1:14:00that emphasized his figure. Not to be
1:14:03outdone, I took a short black blazer
1:14:05from my closet and then decided to
1:14:08casually put on my single-strand pearl
1:14:10necklace. I think we were the most
1:14:13elegant among the women who were
1:14:15enjoying their lunch. I really enjoyed
1:14:18Simon's company. I don't know, but he
1:14:21has changed. Well, of course he has,
1:14:23but I mean that his developing feminine
1:14:26side is so much more pleasant than the
1:14:28old Simon. We used to sit in silence
1:14:30most of the time and enjoy our meal.
1:14:33Now we were chatting animatedly like
1:14:35two women, which, essentially, we were.
1:14:38We had more in common, fashion above
1:14:40all. I enjoyed today's lunch. We should
1:14:44do this more often. I found that a
1:14:46strange remark to make to my wife after
1:14:485 years of marriage. A few weeks later,
1:14:51Simon came home one evening. He and Tom
1:14:53had been to a restaurant with other
1:14:56couples, as he called them. Dian, some
1:14:59of the women are meeting for a
1:15:01ladies-only lunch tomorrow and I
1:15:02thought you might like to come along.
1:15:05That came completely unexpectedly. I
1:15:08had always kept Simon and his wife
1:15:09separate in my mind. My life with Tom
1:15:12had grown out of our own lives. It was
1:15:15my goal for Simon to become more
1:15:17involved in my life. As a woman, it is
1:15:19naturally clear that it worked, but not
1:15:22quite how I had expected. This
1:15:24invitation from Simon would be an
1:15:26opportunity to shift the balance of
1:15:28power in Tom's favor and include me.
1:15:31Yes, I would like that. Great. I should
1:15:34warn you, though. So, there is always a
1:15:37catch. My friends are all of the same
1:15:40breed as Odri. They dress very
1:15:42elegantly. As you know, Audrey’s
1:15:45fashion collection is an incredible
1:15:47source of inspiration for me and helped
1:15:49me be accepted by them. What do you
1:15:52mean by that? That I don't meet your
1:15:54standards? No, no, no, of course not. I
1:15:58know you can dress very elegantly, and
1:16:01this is an opportunity to show it.
1:16:04Besides, I would be happy if you did.
1:16:07Okay, I'm sorry. That’s not what I
1:16:10meant. You are always elegantly dressed
1:16:12, even at home. We should get you some
1:16:15lighter things so you feel more
1:16:17comfortable. Maybe, but I like dressing
1:16:20this way. We spent most of the morning
1:16:23in our bedroom, where I tried on all
1:16:25sorts of outfits and accessories until
1:16:27Simon was satisfied. What a turn of
1:16:30events. I had actually expected to
1:16:32advise Simon on his outfit, my journey
1:16:35into the world of cross-dressing. And
1:16:38there he was, sharing his newly
1:16:39acquired experience as a woman in high
1:16:42society with me. It turned into a warm,
1:16:45sunny day, and we both decided on
1:16:47summer dresses. Simon chose, as I was
1:16:50pleased to note, upon my suggestion, a
1:16:52fitted sleeveless knee-length dress
1:16:55with a round neckline in primrose
1:16:56yellow, plus white stilettos and a
1:16:58clutch. I also wore a fitted white
1:17:02dress with a floral pattern. Mine was
1:17:05calf-length. Against my better judgment
1:17:07, I chose the same stilettos as Simon.
1:17:09I drove us to the restaurant. Simon
1:17:12seems to have given up driving. It was
1:17:14an exclusive club on a country estate.
1:17:17It slowly dawned on me that Simon was
1:17:19serious about his new friends. As we
1:17:22parked, a thought suddenly struck me.
1:17:24Simon, do your friends know who we are?
1:17:27No, that’s exactly the point. As far
1:17:30as they know, I am a woman. I could
1:17:32hardly introduce you as my wife. What
1:17:35do you think they believe you are to me
1:17:37? They actually believe I am Tom's wife
1:17:39. Although neither of us claimed to be
1:17:43married, we didn't deny it either. Is
1:17:46that why you moved the diamond ring you
1:17:48always wear to your ring finger? I
1:17:51think I’d better. Explain that to me.
1:17:55You remember that I came home late the
1:17:57day after the ball. Yes. I remember. I
1:18:01never wanted to ask, and unusually for
1:18:03you, you never told me. When we arrived
1:18:06on Saturday, the room was reserved for
1:18:08Mr. and Mrs. Fleetwood. And naturally,
1:18:11the receptionist and the hotel staff
1:18:13assumed. That I was Tom's wife.
1:18:16That’s what the booking said. I
1:18:18decided to play along. I wore my
1:18:20diamond ring, which I secretly switched
1:18:23to my ring finger. Tom saw it and
1:18:25signaled that he was up for it too.
1:18:28When he booked the room, he was, of
1:18:30course, married and had chosen a double
1:18:32room. When we arrived in our room, he
1:18:35tried to book another room for me
1:18:37online under my name, and as expected,
1:18:39there were no rooms left. At our age,
1:18:43sleeping on a chair or the floor was
1:18:45not an option. So we shared the bed
1:18:48that night, but not in the biblical
1:18:50sense. He had brought pajamas and I had
1:18:53one of my nightgowns—feminine, but
1:18:55definitely not sexy. Although I really
1:18:58had no idea what to expect that night,
1:19:00I still had an uneasy feeling in the
1:19:02back of my mind. I was surprised. They
1:19:05had slept together, and Simon hadn't
1:19:07told me anything about it. He had also
1:19:10never told me why he came back so late.
1:19:12At the ball, we sat at a table with
1:19:14three other couples. All of them
1:19:17retired members with their wives, all
1:19:19of us getting on in years. I got along
1:19:22well with them, and since I had known
1:19:24Tom before he married, I knew enough
1:19:27about him to answer the inevitable
1:19:29questions convincingly. When did you
1:19:32two meet? Do you have children? Things
1:19:35like that. I just had to imagine I was
1:19:38Audrey, or a woman and not a man. The
1:19:40next morning, Tom was supposed to
1:19:42attend a members 'meeting. Since I
1:19:45would be alone, I was invited to take a
1:19:48trip to a nearby garden with the women.
1:19:51Afterward, there was lunch. When one of
1:19:54them learned that they lived not far
1:19:56from Tom's house on our way home, she
1:19:59insisted we stop by for dinner. I
1:20:02accepted on our behalf because I
1:20:04enjoyed their company, but mostly
1:20:06because I thought it would be good for
1:20:09Tom to meet another retired member. But
1:20:12instead of the two men meeting, Tom and
1:20:14I were invited to a dinner party along
1:20:17with the other couples we had met at
1:20:19the ball. Over time, we became part of
1:20:22their circle of friends. So much so
1:20:24that I was even invited to a luncheon
1:20:27just for wives. "I'm sorry you couldn't
1:20:30tell me sooner," I replied. "I know you
1:20:35asked me that evening, but honestly, I
1:20:37was too tired to give you the answer
1:20:39you deserved." The next day, the right
1:20:42opportunity never came up, and as time
1:20:44went on, I kept putting it off. He
1:20:47never mentioned it again and seemed
1:20:49content with me going out with Tom to
1:20:51meet other people. I knew Tom and, of
1:20:53course, Simon well. I could trust them,
1:20:56and they would never do anything
1:20:58inappropriate or hurtful to me. But
1:21:01pretending to be husband and wife, even
1:21:04if it only happened due to an
1:21:05unfortunate circumstance and a
1:21:07misunderstanding without telling me,
1:21:09was unacceptable. Tom had recently been
1:21:12widowed, and Simon was a very desirable
1:21:15woman. If I had found out another way,
1:21:18I would have feared the worst and been
1:21:21devastated. It was like one of those
1:21:23bizarre scenes in a play. That may be,
1:21:26but I was really looking forward to
1:21:28going to this lunch with you. I could
1:21:30introduce you as the wife of Tom's best
1:21:32friend. Which is true, I can do that. I
1:21:36just need to remember that my husband's
1:21:37name is Simon. And you are Debora. Okay
1:21:40, let's go inside. I need a drink
1:21:43before we eat. The lunch and the ladies
1:21:46, Victoria, Penelope, and Mary, were
1:21:48delightful. I was very entertained. It
1:21:52was pleasant that we were all the same
1:21:54age and had husbands who were retired
1:21:56after long, successful careers. They
1:21:59looked timeless and had all stayed
1:22:02young, just like Simon. Simon was
1:22:04obviously very popular and highly
1:22:06regarded, and they said, "Tom is a very
1:22:08lucky man," to which I could only agree
1:22:11. He was indeed lucky to have Simon as
1:22:13a best friend and Debora as a wife.
1:22:16Simon blushed and looked at me, and I
1:22:18just shrugged my shoulders. I wanted to
1:22:21forgive him, but not quite yet. I could
1:22:24understand why Simon felt drawn to this
1:22:26group. They insisted I come again, and
1:22:30since I could be with Simon and keep an
1:22:32eye on him, I agreed. Besides, I
1:22:35enjoyed their company and was happy to
1:22:38see Simon as one of them. They wanted
1:22:40to invite my husband and me to their
1:22:42next meeting. I declined, as my husband
1:22:44has an illness, and we therefore could
1:22:46not attend as a couple. That got me
1:22:49thinking about what might happen if
1:22:52Debora and Tom were to host. At a
1:22:55dinner with friends. As lunch drew to a
1:22:59close, I realized that in this lady's
1:23:01company, Simon wasn't just Debora. But
1:23:04Debora Fleetwood. He was playing a
1:23:07different role. His body language and
1:23:09the way he treated me were subtly
1:23:10different. It was as if he were married
1:23:14to Tom, not me, as if the whole
1:23:16performance were real. On the way home,
1:23:19I asked Simon about it. Simon, how does
1:23:22it feel when you’re Tom’s wife?
1:23:24What do you mean, his wife? At lunch,
1:23:27you were different. You played the role
1:23:29of Tom’s wife so convincingly, it was
1:23:31like it was real. When we were with the
1:23:34ladies, I was your best friend, not
1:23:36your wife. Yes, you’re right. It
1:23:39isn’t intentional, but when we’re
1:23:42with our friends, I unconsciously
1:23:44become her. Tom’s wife, not Audre. I
1:23:47could never be her. But Mrs. Fleetwood,
1:23:50I’ve known Tom and Audre my whole
1:23:52adult life, and I dress from head to
1:23:54toe in her style, following Audre's
1:23:56example. With that in mind, it’s very
1:24:00easy for me to mentally transform into
1:24:02his wife, not Tom. I haven't had the
1:24:05experience of their life together, but
1:24:07socially, I have. It’s as if I have a
1:24:10pre-made backstory as his lifelong wife
1:24:13, and our friends pick up on that.
1:24:16Especially the wives. Actually, I can
1:24:19understand how that happened. But what
1:24:21is it like now that you’re alone with
1:24:23me? Now I’m completely back to normal
1:24:25. I am your husband. Simon, who dresses
1:24:28as a woman and goes by the name Debora.
1:24:31Which of your two lives do you prefer?
1:24:33I love being Debora Fleetwood. Only Tom
1:24:36knows my secret. Our friends think
1:24:39I’m a woman, and that feeling brings
1:24:42me great joy. And when I unconsciously
1:24:44become her, I forget about being Simon.
1:24:47When I’m alone with Tom, I become
1:24:50Simon again. But I enjoy how he treats
1:24:53me as a woman and not as his best
1:24:55friend. When I’m with you or our
1:24:57daughters, I’m Simon, the husband and
1:24:59father I’ve always been, only now
1:25:01I’m actively wearing women’s
1:25:03clothes again. Wearing women’s
1:25:06clothes brings me joy, and I appreciate
1:25:08your acceptance. When we’re in bed, I
1:25:11am your husband in every way. Well,
1:25:14except for the hair, nails, and
1:25:16nightgown. I grinned. When we got home,
1:25:19it struck me that Simon had never said
1:25:21whether he prefers being Tom's husband
1:25:23or being a transvestite by my side.
1:25:26Maybe he doesn't even know yet and can
1:25:28enjoy both roles. And is that a problem
1:25:31? Not at the moment. Actually, it means
1:25:34he leads a fulfilled life. The reason
1:25:37for my plan, albeit different than
1:25:39expected, is that things will
1:25:40inevitably change as soon as he comes
1:25:43out to our relatives and friends and
1:25:44appears publicly as Debora. Life went
1:25:48on. Simon continued to enjoy it. Being
1:25:50Mrs. Debora Fliedwo. At least as far as
1:25:52his life with Tom was concerned. Simon
1:25:56and I regularly met the wives for lunch
1:25:58, shopping, excursions, and other
1:26:00activities that wealthy retirees like
1:26:03to do. Simon and I spent more time
1:26:06together. We went out more often. Simon
1:26:10became more and more natural in every
1:26:12aspect of womanhood, even though he is
1:26:13a man, the closer our wedding
1:26:15anniversary approached. I had lunch
1:26:17with Penelope and Mary for the first
1:26:19time with Simon's friends without him.
1:26:22Tom and Simon had traveled to Victoria
1:26:24and her husband, who were in southwest
1:26:26England due to a hotel mishap. I was
1:26:29very pleased that Penelope and Mary had
1:26:31assumed I would have lunch with them
1:26:33without Debora. Victoria and Debora
1:26:37seemed to be in a friendly rivalry,
1:26:40judging by the WhatsApp photos, said
1:26:42Penelope while we waited for our food.
1:26:46The friendly rivalry was probably about
1:26:48who could present themselves more
1:26:49fashionably. Simon had packed a summer
1:26:52dress or skirt for every day and a
1:26:54cocktail dress for every evening, along
1:26:56with matching shoes, bags, and
1:26:57accessories. Luckily, Tom's SUV had
1:27:00plenty of space for luggage, and Debora
1:27:03surpasses Victoria in my opinion,
1:27:05Penelope continued. I agree with that,
1:27:08said Mary. She has a natural talent for
1:27:11dressing perfectly for every occasion.
1:27:14I wish I had her looks and her figure.
1:27:17She has aged well. That has always been
1:27:20my opinion, but of course, I am biased.
1:27:23When he and Tom were invited to visit
1:27:25Victoria and her husband, Simon said
1:27:27there was no reason to refuse. He knew
1:27:31he would enjoy being Tom's wife for a
1:27:33week and therefore naturally accepted.
1:27:36A double room was obviously booked as
1:27:38well. I was a bit hurt at first, not
1:27:41because I was jealous. Simon had
1:27:43actually packed very modest nightwear,
1:27:45but because I would be alone. At least
1:27:48I'm enjoying my lunch. They have become
1:27:51good friends of mine by now as well.
1:27:52Tom can consider himself lucky to have
1:27:55a wife like Debora, Mary continued. I
1:27:57agree with that. Although she appears
1:28:00to be an independent woman on the
1:28:01outside, she is very devoted to him.
1:28:04They are always proud of one another,
1:28:05and they still enjoy each other after a
1:28:07lifetime of being together. Did you
1:28:10notice how they finish each other's
1:28:12sentences or intuitively know what the
1:28:13other is thinking? "That is a true
1:28:16marriage," said Victoria. The
1:28:18conversation was slowly becoming too
1:28:20much for me. It was obvious that they
1:28:22had no idea of Simon's true gender or
1:28:24that he is married to me and lives with
1:28:27me, which was a relief. But if they
1:28:29knew, would they still speak so
1:28:31enthusiastically about Simon and me? I
1:28:33am already curious about what Debora
1:28:35will wear this evening. Certainly
1:28:37something special. After all, it is
1:28:39Tom's birthday, Victoria continued. Of
1:28:42course, I could tell you. He had packed
1:28:45his favorite dress, the little black
1:28:47one. It was one of Audrey's designer
1:28:50dresses. It was strapless with a tight
1:28:53bodice shaped by a corset, showing more
1:28:55cleavage than usual, and a flared skirt
1:28:57with a mid-high waist and a mesh
1:28:59overlay. He will wear strappy pumps and
1:29:03the diamond necklace that Tom gave him.
1:29:05A birthday present for Tom. A small
1:29:08trump for Victoria no doubt and a
1:29:10little joke for her husband. Simon will
1:29:13feel perfectly at home. The
1:29:15conversation continued in a similar way
1:29:17during lunch. They admired Debora very
1:29:19much and envied her for her marriage to
1:29:21Tom. I lay in bed waiting for Simon to
1:29:24come out of the bathroom so I could
1:29:26turn off the light. He had returned
1:29:29from his break this afternoon. When the
1:29:32door opened, my breath caught. I
1:29:34couldn't believe it. He was wearing a
1:29:37sheer black negligee over a very sexy
1:29:39red and mauve corset. Attached to the
1:29:43corset were six garter clips holding a
1:29:45pair of sheer black seamed stockings.
1:29:48He was wearing incredibly high heels.
1:29:50He was having some trouble with them. I
1:29:52think he has reached his limit. Simon,
1:29:55what on earth are you wearing? Well, my
1:29:58bachelor party was 50 years ago. Well,
1:30:01I could hardly organize a reunion with
1:30:03perfectly styled hair and nails and, of
1:30:06course, my plucked eyebrows. Besides,
1:30:09only Tom is left from the original
1:30:11group, but that doesn't explain it yet.
1:30:13I was just about to get to that,
1:30:16darling. I have wanted to try on this
1:30:18corset for so long, ever since I first
1:30:20discovered it in Audrey's things.
1:30:22Audrey wore something similar. Our
1:30:24Audrey was a real surprise. Among her
1:30:28things are some, let's say, erotic
1:30:30items. Some may not quite suit our
1:30:33taste, but I really like this ensemble.
1:30:37This corset cannot be hidden under a
1:30:39dress. It must be seen, but only in
1:30:42private, and that means only for you
1:30:44and me, not even for Tom. He loves to
1:30:47see you in Audrey's dresses. I am sure
1:30:50he had a lot of fun seeing Audrey in
1:30:52them. I wondered if Tom had ever seen
1:30:55Simon in lingerie, other than his
1:30:58pajamas when they shared a hotel room.
1:31:01Not even Tom, just you and me. I must
1:31:03admit, Simon looked very sexy. It
1:31:06proves, contrary to the idealized
1:31:08depiction of women in the media, that
1:31:11you don't have to be slim, young, and
1:31:13female to look sexy in a corset. I
1:31:15found this side of him very attractive
1:31:18when we met. And I am so glad that my
1:31:21plan to revive his cross-dressing
1:31:24worked. I hope his coming out at the
1:31:26party doesn't go catastrophically wrong
1:31:28. I see you are struggling with those
1:31:31heels. Maybe a step too far. Yes, you
1:31:34are right. I don't know how Audrey
1:31:36managed with them, but they hardly look
1:31:39worn, so maybe she didn't. Simon sat on
1:31:42the edge of the bed. Take them off so I
1:31:44can come to you. He took off his shoes
1:31:47and then the negligee and got into bed.
1:31:50I was no longer tired. I felt Simon and
1:31:52his wonderfully shaped body and the
1:31:54silky stockings. Oh yes. A while later
1:31:57he stood up and I helped him take off
1:32:00the corset. I don't know how he managed
1:32:03to put it on so tight. He was sweating
1:32:06in the sheer nightgown that belonged to
1:32:08a very feminine set with the negligee.
1:32:10I was glad that Audrey wanted to buy
1:32:13such things. But perhaps it was a gift
1:32:15from Tom or even an admirer. We slept
1:32:18soundly for the rest of the night. My
1:32:20hand rested gently on his chest.
1:32:23Tomorrow he will be with Tom. The
1:32:24golden wedding anniversary celebration.
1:32:27It was to be an evening reception with
1:32:29dinner and dancing in a private hotel
1:32:30ballroom. Simon and I had decided to
1:32:34get ready separately and arrive
1:32:35individually, just like at our wedding.
1:32:38I went to my regular hairdresser and
1:32:39then got dressed at home with the help
1:32:41of my younger daughter. I knew he
1:32:43wanted to wear the gold dress again. He
1:32:46loved it and it meant a lot to him.
1:32:49Besides, only Tom has seen him in it
1:32:51and only I knew of the photo of them. I
1:32:54bought a long red evening dress that I
1:32:56thought would go well with the gold.
1:32:59Simon was staying with Tom and would
1:33:01accompany him to the party. He told me
1:33:03he would visit the salon he had also
1:33:06been to for Audrey's funeral. We had
1:33:09arranged to meet in the hotel lobby and
1:33:11intended to go to the ballroom together
1:33:13once our guests had taken their seats.
1:33:16When I saw Simon waiting with Tom in
1:33:18the foyer, my breath hitched. Seeing
1:33:21him in his evening gown, arm in arm
1:33:23with Tom, who looked so good in his
1:33:25tuxedo, made me realize the photo from
1:33:27the ball didn't do them justice. Simon
1:33:30was beaming. I had never seen him look
1:33:32so stunning, so perfect. He was wearing
1:33:35my diamond necklace, just as I had
1:33:37planned—which feels like an eternity
1:33:39ago now—along with the bracelet and
1:33:41earrings our daughters had given him.
1:33:43His confident posture and the joy on
1:33:45his face confirmed to me that I had
1:33:47made the right decision for his
1:33:49happiness in his later years. Despite
1:33:52his age, he outshone everyone else in
1:33:54the foyer, myself included, of which I
1:33:56was immensely proud. I exchanged kisses
1:33:59with Tom. Ready? he asked. Yes, I
1:34:03whispered. I was nervous that
1:34:05everything might go wrong. Simon pulled
1:34:08his arm away from Tom's hand, took his
1:34:10hand, drew him closer, and kissed him
1:34:12on the lips. Thank you, my dear Tom, he
1:34:15whispered. Then he let him go and
1:34:18linked his arm with his. I took my arm,
1:34:21let go of him, opened my purse, took
1:34:23out a small box, and handed it to Simon
1:34:26. He opened it. This is a token of my
1:34:30love and in memory of 50 years of a
1:34:31happy life, I explained. It is a
1:34:34wedding ring. He looked at my left hand
1:34:37, or rather, at a duplicate. Who else?
1:34:40Silly man. He slid the wedding ring
1:34:43onto his ring finger. Now everyone
1:34:45could see that he was married. Judi,
1:34:48who had been waiting quietly in the
1:34:50foyer, came over. Dad, Mom, you both
1:34:53look stunning. Are you ready? Let's go.
1:34:57Our audience is waiting, Simon replied.
1:35:00As Simon lifted his skirt, I could
1:35:02finally see his shoes. I was surprised
1:35:05at what Audrey had bought at her age,
1:35:07and indeed, Simon was wearing them at
1:35:10his age. I was also a little jealous.
1:35:13He was wearing strappy sandals with at
1:35:15least 4-inch heels. The straps
1:35:18glittered with sequins that matched the
1:35:20top of the dress, and his clutch and
1:35:22perfectly painted red toes were visible
1:35:24. I guess Stella knows no limits. If
1:35:28you can pull it off, go for it. We
1:35:30followed Judy into the room, Claire and
1:35:32Tom behind us. At first, we heard a
1:35:35murmur from our guests, then someone
1:35:37started to clap. Very quickly, the
1:35:40others joined in, applauding as Judy
1:35:43led us to our table. Sitting there were
1:35:45Judy's husband Harry, our granddaughter
1:35:48Jessica, and Doris, Simon's sister.
1:35:50Claire's husband, Nigel, had decided
1:35:52not to come. He was the only one on the
1:35:55guest list who had declined the
1:35:56invitation. Claire and he argued about
1:35:59it and subsequently separated. For
1:36:02Claire, her father, regardless of his
1:36:03gender identity, was more important
1:36:05than her marriage to Nigel. I must
1:36:08confess that I am not at all sorry that
1:36:10I will likely never see my so-called
1:36:12son-in-law again. As everyone had taken
1:36:14their seats, I looked around at our
1:36:16family. Tom has always been a part of
1:36:19us, and I am proud of how much he has
1:36:21loved and supported Simon. That was
1:36:24when the scales fell from my eyes. Our
1:36:26Jessica, now a young woman, looked so
1:36:28much like Simon did when we first met.
1:36:32Perhaps more feminine and delicate, but
1:36:34she is a young woman and you can
1:36:35clearly see that she inherited her
1:36:37grandfather's features. We enjoyed the
1:36:40meal, chatted animatedly, and shared
1:36:43family memories. Of course, we all knew
1:36:46who the lady in the gold dress, unknown
1:36:48to at least some, was, and we played
1:36:50along. Simon seemed so natural, sounded
1:36:53so authentic, and behaved so normally
1:36:55that it was easy to accept him. Keep
1:36:58playing along. The best man's speech,
1:37:01part 2. Hello everyone, I'm Tom
1:37:04Fleetwood. The older ones among you who
1:37:06still remember—there was some quiet
1:37:08laughter—will remember me as the best
1:37:10man at Dian and Deborah's wedding
1:37:12exactly 50 years ago. Back then,
1:37:14Deborah was still called Simon,
1:37:15although I called him "Blondie" after
1:37:17Debbie Harry. Kids and everyone else
1:37:19who isn't quite as young anymore, ask
1:37:22your grandparents who she was. Before I
1:37:25continue, I would like to thank Judy
1:37:27and Claire for organizing this
1:37:28wonderful celebration for their parents
1:37:30. There was loud applause and a bit of
1:37:33table thumping. Judy seemed a bit
1:37:35embarrassed, but Claire enjoyed it to
1:37:37the fullest. Don't worry, I won't
1:37:40repeat the stories I told back then as
1:37:42the best man. My material is no longer
1:37:45suitable for our more tolerant and
1:37:47respectful audience of today. There was
1:37:50more laughter, this time with more
1:37:52understanding. Simon and I were best
1:37:54friends. Simon was what they called a
1:37:57transvestite back then. He was very
1:37:59pretty and a typical partygoer of the
1:38:01seventies. But it wasn't all just fun
1:38:03and games. He studied hard and got a
1:38:06respected job during that time.
1:38:09Eventually, he met Di at a party and
1:38:11they fell in love. Soon she also got to
1:38:14know Simon, and they had a perfectly
1:38:16normal romance, except she had the best
1:38:18of both worlds: a boyfriend and a
1:38:20girlfriend. After Judy appeared, Simon
1:38:23hung up his bra for good. His
1:38:25priorities were now to support his
1:38:28young family and be a good father. When
1:38:31he retired, he didn't know what to do
1:38:33with himself. No more career, and his
1:38:35daughters were now living their own
1:38:37lives. Dian was concerned, but she had
1:38:39a plan. She gave him a diamond necklace
1:38:43for his 70th birthday. Her idea was to
1:38:46introduce the new Simon wearing the
1:38:48diamond necklace to family and friends
1:38:50at their golden anniversary. That day
1:38:52has now arrived and you are all here.
1:38:54But instead of Simon wearing a dress,
1:38:56we welcome Debora together with Dian's
1:38:59dress, the girl, and of course, me.
1:39:01Love and support. She now lives fully
1:39:04as a woman. She is still Dian's husband
1:39:06and, as Aunt Debora, a kind of father
1:39:08to her daughters. If you have
1:39:10understood all that, perhaps you can
1:39:12explain it to me. There was laughter
1:39:14and murmuring. Some were in the know,
1:39:17some were confused. Or, of course, you
1:39:19can read the excellent announcement and
1:39:21the letter from Judy and Claire, as
1:39:23that was part of your invitation. We
1:39:25didn't want any surprises today. Of
1:39:27course, Debora is not the star tonight.
1:39:30That honor belongs to Dian. No one can
1:39:32hold a candle to her, and it was her
1:39:34love and courage that awakened the
1:39:36woman sleeping within Simon. Dian,
1:39:38please stand up. That wasn't planned,
1:39:42not that there had been a script. I
1:39:44hadn't expected it. When I was the
1:39:47bride forty years ago, I just sat there
1:39:49, smiled, and listened to the speeches.
1:39:52But that was then and now is now. So I
1:39:55stood up, and as I did, applause and
1:39:57cheers broke out. I must have done
1:40:00something right. As I said, I was
1:40:02Simon's best man. And we remained
1:40:05friends. We met regularly for lunch and
1:40:07I was, besides Dian, the only person
1:40:10who knew that Simon used to be a
1:40:12crossdresser. The desire and the
1:40:14feeling had never left him and had
1:40:16remained dormant for almost five
1:40:18decades. With Dian's help, Simon
1:40:21reached a point last year where he
1:40:22could easily pass as a woman again.
1:40:25Then a personal tragedy struck me. My
1:40:28wife Odri, to whom I had been married
1:40:30for 50 years, died suddenly. She was my
1:40:33everything. At our age, one's circle of
1:40:36friends shrinks as people pass away.
1:40:39But I still had regular contact with my
1:40:41old friends. My friend Simon. He was
1:40:44the one I turned to when I needed
1:40:47someone. He helped me organize the
1:40:50funeral and settle my affairs. But I
1:40:53was feeling sorry for myself. I missed
1:40:55Odri. I missed the company of a
1:40:58charming and cultured lady. I needed
1:41:01female company and I encouraged my best
1:41:03friend to take her place. Of course not
1:41:07all the time, but on the days when Odri
1:41:09would have accompanied me. By stepping
1:41:12in for her, Debora, as she is now
1:41:14called, eased my grief for my late wife
1:41:17by giving me back a piece of my
1:41:19once-normal life. Before I continue,
1:41:23and I hope you continue to understand,
1:41:25because I am telling you all this for a
1:41:27reason, I want to share some truths to
1:41:29avoid misunderstandings. I was slowly
1:41:33getting restless, wondering what Tom
1:41:34was getting at. I squeezed Simon’s
1:41:36hand and looked into his perfectly
1:41:38made-up eyes. He was calm and composed
1:41:40while listening to Tom and looking
1:41:42around at the guests. First of all, I
1:41:45would like to clarify that Debora is
1:41:46not a woman. She hasn't had a sex
1:41:49change and is definitely not
1:41:51considering one. She simply dresses and
1:41:53presents herself as a woman at all
1:41:54times. That’s why she’s called
1:41:56Debora now. She is definitely not trans
1:41:59. Everything you see is reversible. She
1:42:02can become a man again if she wants to
1:42:04or has to. She has told me many times
1:42:06—sometimes I think to make sure I
1:42:08really understood it—that she loves
1:42:10her even more than ever because of that
1:42:12and doesn't want to leave her. Today is
1:42:15an important day for you, because it is
1:42:17your golden wedding anniversary and not
1:42:19just her debut as Debora. What I had
1:42:22just heard was reassuring, but I must
1:42:24admit, even though I had convinced
1:42:26myself there was nothing to fear, I had
1:42:28feared the worst. I squeezed his hand
1:42:31again and he turned to me and gave me a
1:42:34disarming smile. Tom’s speech was a
1:42:37revelation to me. I wondered what the
1:42:39others were thinking. When he paused,
1:42:42he looked at me. I’ll wrap this up
1:42:44now so you can dance. There was the
1:42:47inevitable applause. Everyone was in
1:42:49the best of moods. Tonight we are
1:42:51celebrating two extraordinary women who
1:42:53have been together for over half a
1:42:55century. We are also celebrating Debora
1:42:58, who has entered our lives, and I hope
1:43:00that you will welcome her into your
1:43:02lives and make her a part of them, just
1:43:04as you did with Simon, as we all grow
1:43:07older. Ladies and gentlemen, please
1:43:09raise your glasses to Dian and Debora
1:43:12MC. Dian, you did something wonderful
1:43:15during the last dance. Tom and I were
1:43:19dancing, and that gave us the chance to
1:43:21talk. Simon was a quiet, shy man.
1:43:25Constantly busy with work or caring for
1:43:27his family, he hardly had any time for
1:43:29social interactions. Our regular
1:43:32lunches and, when we were younger, our
1:43:35pub visits were the only regular
1:43:37activities he enjoyed outside of home
1:43:39or the office. Simon as Deborah, on the
1:43:43other hand, is outgoing, likable, and
1:43:45loved by everyone who meets him. Look
1:43:48at him now. He is in his element,
1:43:51greeting and chatting with the guests.
1:43:54Simon as Deborah, as you say, needs a
1:43:56man by his side. I pause briefly to
1:44:00reflect: someone to take him out,
1:44:02accompany him to special occasions,
1:44:04chat with other couples with him, go
1:44:07dancing with him, someone to compliment
1:44:09him, tell him how beautiful he is, give
1:44:12him flowers, someone loyal, someone he
1:44:14can be proud of, who protects him and
1:44:17makes him feel safe. And that man is
1:44:20you, Tom. You were that man. For once,
1:44:23Tom was speechless. And Tom, you
1:44:26obviously need a woman by your side.
1:44:29Not someone to replace Audrey, but a
1:44:32friend. Someone like Deborah. Simon was
1:44:35your best friend, now Deborah is your
1:44:38best friend. You are a perfect couple.
1:44:41But Diane, Simon is a husband. You take
1:44:43care of him. You give him love. You are
1:44:46the mother of his children. You are the
1:44:48homemaker. Audrey and I always thought
1:44:51you were the perfect couple. Simon
1:44:53tells me constantly how much he owes
1:44:55you and that he loves you very much. I
1:44:57know, that’s true. Simon is happy
1:45:00living as a woman with me.
1:45:02Cross-dressing and the desire to
1:45:04present himself as a woman have always
1:45:06been a part of him. He is my best
1:45:09friend, but he is still my beloved
1:45:11husband, the man I share my bed with.
1:45:14But as a woman, he needs more than that
1:45:16. Things that I cannot give him or
1:45:18share with him. And that is where you
1:45:20come in. I want us both to continue
1:45:23sharing his life so he can enjoy his
1:45:25retirement to the fullest. I must admit
1:45:28, he has been a lifesaver since I lost
1:45:31Audrey. Not as a replacement, but he
1:45:33was there when I needed help or company
1:45:35. He really reminds me so much of her.
1:45:38He wears her clothes and her perfume
1:45:40and maintains her style by expanding
1:45:43her wardrobe. Yes, I know, the clothes
1:45:46were perfect. For him and for both of
1:45:48us, his new style is pleasing. It suits
1:45:50him well. With your blessing, I would
1:45:52like to be that man. I love Simon as
1:45:54Deborah. He was my best friend. Now he
1:45:58is my best friend. Our new relationship
1:46:00is purely platonic. No, that doesn't
1:46:03quite describe it. We are more like
1:46:05brother and sister. We kiss and hug
1:46:08each other, but only to show affection,
1:46:10not for romantic reasons or to seek
1:46:13physical pleasure. I am happy to leave
1:46:16that side to you. After all, we are
1:46:18both heterosexual men. He laughed. Well
1:46:20, you have always been an honorary
1:46:22member of the family. You were Uncle
1:46:24and Odri, an aunt to the girls, when
1:46:26they were small. So if Simon is your
1:46:29sister, then you are basically still
1:46:31her uncle. Thank you, Diane. I am very
1:46:34happy to be part of your family. Could
1:46:37you separate Simon's relationship with
1:46:38you as Mrs. Debora Fleetwood from his
1:46:40new life with me? Of course, I will
1:46:42simply be Simon's best friend to your
1:46:44extended family and friends. Simon had
1:46:47told me about that night at the hotel
1:46:49when you lay in bed together. To
1:46:51protect Debora's honor and to put your
1:46:54mind at ease, I behaved like a
1:46:56gentleman all night long. As he said
1:46:58that, Tom looked at him. I said it to
1:47:01him as if to say: "Simon is truly loyal
1:47:03to me and I am safe in his company." He
1:47:06also told me that he was known as Mrs.
1:47:08Fleetwood, your wife, that weekend and
1:47:11you both played along. "Nothing
1:47:14inappropriate, I assure you, but a
1:47:16perfect example of how people have
1:47:18taken Debora into their hearts." And
1:47:20that is how we became part of her
1:47:22circle of friends. Diane, I hope you
1:47:24can forgive me and continue to treat
1:47:26Debora as my wife in social settings,
1:47:28otherwise I will be in trouble. I
1:47:31leaned forward and kissed Tom on the
1:47:33lips and I can show him my gratitude.
1:47:36Welcome to the family. If Simon wants
1:47:39to enjoy his retirement a bit more and
1:47:41see more people, I would prefer Tom
1:47:43over anyone else. Besides, we owe Tom a
1:47:46lot, and he should continue to be able
1:47:48to enjoy seeing him in Audrey's dresses
1:47:51and skirts. Tom had more or less
1:47:53confirmed what Simon had already told
1:47:56me. I knew that my husband had remained
1:47:58faithful to me, but it is nice to know
1:48:01for sure. Ladies and gentlemen, it is
1:48:03time for the final dance. The DJ is
1:48:06being announced. So grab your loved one
1:48:09and we will see you on the dance floor.
1:48:11Tom and I let go of each other as I
1:48:14looked for Simon. He had been dancing
1:48:16all night long. Among the men in our
1:48:18family and our friends, he seemed
1:48:20completely at ease, dancing as the
1:48:22glamorous Debora, whom they had only
1:48:24known as Simon until this evening. Then
1:48:26I saw him rushing toward me as fast as
1:48:29he could in his high heels. Slow down,
1:48:31darling. I was afraid he would fall in
1:48:34those heels if he wasn't careful.
1:48:37You’re not a young man anymore. We
1:48:39hugged tightly, pressing our chests
1:48:41together and dancing, completely
1:48:43unfazed by everything around us. On our
1:48:46golden wedding anniversary, I knew that
1:48:49everything had gone to plan, more than
1:48:51I could have ever imagined. I felt that
1:48:54the connection between us was as strong
1:48:56as ever. I would never lose him on our
1:48:59journey through the golden sunset of
1:49:01our lives. Darling, I looked Simon in
1:49:04the eyes. The diamond ring you’re
1:49:07wearing, did Tom give it to you or was
1:49:09it in Audrey’s jewelry box? It was
1:49:11Audrey’s engagement ring. Tom asked
1:49:13me to wear it to the funeral. He said
1:49:16it would help him mourn. I’ve been
1:49:19wearing it ever since. Should I take it
1:49:21off? He sounded a little sad. Oh no,
1:49:24you must wear it for Tom. Why don’t
1:49:26you put it on your ring finger next to
1:49:28your new wedding band? Simon, he smiled
1:49:31. We stopped dancing. He took the ring
1:49:33off and gave it to me. I slid it onto
1:49:36his ring finger, placed it next to the
1:49:38wedding band I had just given him, and
1:49:40kissed him on the lips. We continued
1:49:42dancing, holding each other even closer
1:49:44. M.

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