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Aunt Helped Me Achieve My Feminization Dream (Crossdressing Stories) — Transcript

by Sissy Maya · 3,448 words · 518 segments · language en · Watch on YouTube

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0:00Welcome back to Maya.
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0:12and much more.
0:13Years ago, during a visit to my aunt
0:15Margaret, I mustered the courage to ask
0:18her to dress me in my cousin Sally's
0:20clothes. Aunt Margaret, whom I adored,
0:23always made my summer stays enjoyable.
0:26Unlike my mother, she was easy to talk
0:28to. Aunt Margaret, divorced from her
0:31husband, had lived with Sally until
0:33Sally left for college last year.
0:36Spending summers with Aunt Margaret felt
0:38like the right time to ask. But how
0:41would she react? I harbored a lifelong
0:43desire to wear girls' clothes, but never
0:46understood why. I'd sneak into my
0:48mother's and sister Nancy's wardrobes
0:50occasionally, but I couldn't confide in
0:53them about my secret wish. I almost got
0:55caught a few times when Nancy or mother
0:58returned home unexpectedly. I'd rush to
1:01change back into my own clothes, hiding
1:03theirs. Occasionally, I'd dare to go
1:06further, dabbing on nail polish,
1:08lipstick, slipping into high heels, or
1:11even trying on Nancy's prom dress.
1:13Despite feeling exhilarated, I also felt
1:16ashamed for sneaking around. I wondered,
1:19what if a compassionate woman or girl
1:22agreed to dress me as a female and let
1:24me explore being a girl under their
1:25guidance? Auntie Margaret appeared as
1:28someone approachable to pose my question
1:30to. Auntie Margaret, may I ask you
1:33something? And can you promise not to
1:36chuckle? Jonas, what's on your mind?
1:39Have I ever belittled your thoughts?
1:41"Tell me," she said, sensing something
1:44might be amiss. "Well, I've been
1:47pondering for a while now, curious about
1:49the differences between boys and girls.
1:51I mean, in what they wear, how girls'
1:53attire differs so greatly from boys.
1:56I've often wondered how it might feel to
1:58be dressed as a girl. I've been too
2:00afraid to ask mother or Nancy, but I've
2:03always felt at ease conversing with
2:05you." I stumbled over my words, my
2:08eagerness palpable. "Do you think
2:10perhaps, while I'm staying with you this
2:12week, you'd allow me to experience what
2:14it's like to pretend to be a girl and
2:16wear my cousin Sally's clothes?" "Why,
2:19Jonas, what's the motivation behind
2:21wanting to do something like this? What
2:24makes you believe being a girl would be
2:26easier or preferable to being a boy? You
2:29understand that being a girl involves
2:31more than just trying on dresses. You
2:33wouldn't truly understand unless you
2:34experienced it for a week or longer,"
2:37she said, clasping my hands in hers,
2:39offering comfort despite her words.
2:42"There are neighbors and others who
2:43might visit. If you were to play the
2:46role of my niece for the next week or
2:48two, I'd have to treat you as a girl,
2:50you know." Doubt crept into my mind.
2:53Could I convincingly pass as a girl?
2:56"But honestly, you're not being serious,
2:58are you? What sparked this idea? Is
3:02there something else you're keeping from
3:03me? Are you perhaps questioning your
3:06sexual orientation, maybe thinking
3:08you're gay?" "No, not at all. I
3:11genuinely like girls. I have crushes on
3:14them all the time," I protested
3:16anxiously, not wanting her to doubt my
3:18feelings, yet feeling the need to
3:20explain. "But unlike some boys who see
3:22girls only for pleasure, I find girls
3:25and women intriguing, unique. For some
3:28reason, I've always wished I could
3:30occasionally dress up as a girl, not to
3:32be ridiculed or seen as strange. I'm
3:35really unsure what to do, but I thought
3:38if I had the chance to be a girl for a
3:39while, perhaps with you, I could see if
3:42the desire fades. If I could try being a
3:45girl for a few days." "Well, then,
3:47Jonas, perhaps to address your
3:49curiosity, your auntie could agree to
3:52dress you in clothes you find enjoyable
3:54to wear. But what if, after a while, you
3:57realize that wearing girls' clothes
3:59isn't as enjoyable? She pondered,
4:01shaking her head with numerous
4:03questions. "Will you enjoy wearing and
4:06walking in high heels? Have you
4:08considered that wearing girls' clothes
4:10might not be as appealing? And if you
4:12try it and don't like it, and our
4:14neighbors have seen you as a girl, do
4:16you have the courage to see it through
4:18until your visit is over?" "Yes, I
4:21haven't taken this decision lightly. I
4:23wouldn't have asked you if I thought it
4:25was just a whim. I feel this is
4:27something I truly need to do. With Sally
4:30away at college and just the two of us
4:32here for 2 weeks, I thought this might
4:34be an opportunity one might not have
4:36again." "All right, I can see you're
4:39committed to this. But if you truly want
4:41to experience being a girl, simply
4:43dressing up won't suffice. We'll need to
4:46immerse you in the experience of being a
4:48girl. We'll give you a girl's name, keep
4:51you exclusively in girls' clothes for
4:53several days, let you experiment with
4:55curling your hair and keeping nail
4:57polish on constantly, everything
4:59possible to help you truly feel like a
5:01girl. Eventually, as you live and act as
5:04a girl, you'll likely realize how much
5:06better off you are as a boy." She nodded
5:09confidently, satisfied with her plan.
5:12"Your name will be Cynthia, Jenny. I'll
5:15try not to think of you as my nephew
5:17Jonas. You'll be my niece, Jenny. Of
5:20course, you'll need to shave off any leg
5:22and body hair you have, except what's
5:24covered by your panties, especially if
5:27you want to look good in a party dress.
5:29To fully embrace your femininity, you
5:31must look entirely female. Your body
5:34hair will grow back in time," she
5:36suggested, testing my commitment to
5:38being a complete girl. "Be a good sport.
5:41With my new electric razor, you won't
5:44feel a thing." With nerves jangling, I
5:47pondered how long it might take for the
5:49hair to grow back. How would I explain
5:51it when I went swimming later in the
5:53summer? Yet, if I didn't shave, my
5:56adventure would come to an abrupt end.
5:59"Okay, I'll shave it off, I promise,"
6:02acknowledging that the decision was
6:03made. Once my body was shaved, there was
6:06hardly any chance to turn back. "Good.
6:10Head upstairs to my bathroom where the
6:12electric razor is. Once your body is
6:15shaved, I want you to take a nice bubble
6:17bath. While you're pampering yourself,
6:20I'll search through Sally's belongings
6:22she left behind. Perhaps some of her
6:24older clothes, which were smaller, would
6:27fit you nicely." Once completely shaved,
6:30I cautiously eased into the pink foaming
6:32bubble bath, relishing the soothing
6:34comfort as I heard Aunt Margaret in her
6:37bedroom. After bathing, drying off, and
6:40dusting myself with the girlishly
6:41scented powder she handed me through the
6:43partly opened door, I hesitantly wrapped
6:46my now all too dainty form in a bath
6:48towel before nervously entering the
6:50bedroom. She positioned me with my back
6:52to her as she eased a pair of Sally's
6:54Spandex panty briefs up my legs,
6:57smoothing my lower body. Seeing my
6:59embarrassment, she half giggled with
7:01amusement. As she ran her fingers over
7:04my body to use her razor and skin cream
7:07to remove what little body hair I had
7:10missed, she then plucked my eyebrow
7:13hairs with a pair of tweezers until I
7:15feared that all that was left was a thin
7:18ultra-feminine line that would not
7:20vanish in 2 weeks. Satisfied with
7:23denuding me, she reassured me that my
7:25feminine brows could be brushed into a
7:28masculine look by demonstrating the
7:31change before the vanity mirror. And as
7:34I sat, looking at the growing femininity
7:37of Jenny's face, she set my longish hair
7:40into rollers. "Now that you are wearing
7:43only your underpants, I mean your
7:45lingerie, we can get proper
7:47measurements," she noted, seeing that my
7:50modesty was protected, even if I was
7:52blushing as she took a sewing tape to
7:55carefully measure. "My, my, I can no
7:58longer see my nephew, just a young girl.
8:01Soon I will know you only as Nancy's
8:04sister. Now, we will be sure to get all
8:07your sizes, bust, hips, waist. We will
8:11add a few inches to your bust with bust
8:14pads. All young ladies want to enhance
8:18their nearly be look with falsies, and I
8:20am certain you will look great in
8:22Sally's." Then she took the tape measure
8:25to my foot. "And your feet, I don't know
8:28if Sally's shoes or mine would fit you
8:31better. They may be snug, but to be a
8:34woman is to suffer." Auntie had me sit
8:36as she gave me a manicure and polished
8:39my fingernails a lovely pink, and then
8:42had me let them dry while she went to
8:44Sally's room to get other clothes for me
8:47to try on. Before departing, she made a
8:50commitment to ensure I remained dressed
8:52in feminine attire for the entire
8:54upcoming week. I anticipated embracing a
8:57female identity during this period,
8:59adopting the name Jenny, as my male
9:01clothing would be securely stored away
9:03upon her departure, leaving me with only
9:05girls' garments to wear. After she left,
9:08I found myself sitting very carefully
9:10with my hands on the vanity table so
9:13that my pretty nails could dry, seeing
9:16in the vanity mirror a young girl
9:18sitting in her underwear with her hair
9:21up in curlers. Shortly thereafter,
9:23Auntie Margaret returned bearing a
9:25sizeable box brimming with delightful
9:27attire, which she cheerfully emptied
9:29onto her bed, accompanied by a camera.
9:32"Extend your fingers. I'll apply another
9:35layer of polish to your fingernails.
9:37Then I'll attend to your toenails.
9:39Wearing nail polish will truly enhance
9:42your femininity. Keep them painted all
9:44week as you practice embracing your
9:46feminine side," she remarked, reaching
9:48for the polish to begin my manicure
9:50before using a buff pad to refine the
9:52skin on my feet and concluding with a
9:54pedicure, followed by the application of
9:57nail polish. To my astonishment, she
10:00then captured a snapshot with her camera
10:02just for my scrapbook. But perhaps you'd
10:05appreciate me sharing copies with your
10:07mother and sister, she joked, noticing
10:10the sheer fear in my eyes. Well, maybe
10:13for now, just for myself. Now that we
10:16have your sizes, I want you to put on
10:18your female foundation garments all by
10:21yourself. You will feel quite different.
10:24As a high school sophomore in feminine
10:26lingerie, under her playful instruction,
10:29I eased into the lingerie, absorbing the
10:31lesson on enhancing my chest by leaning
10:34forward to fill the padded cups, then
10:36adjusting the bra straps. Next, she
10:39demonstrated the technique for rolling
10:41up my stockings and fastening them to
10:43the garter snaps on the girdle. Finally,
10:46I slid the white silk slip over my
10:48feminized figure, reveling in the
10:50delicate sensation of lace brushing
10:52against my sleek stockings. You appear
10:55quite feminine in your lingerie. Just
10:57wait until we're done with you, she
10:59assured, gazing at her initial efforts
11:01with her approving nod, which filled me
11:03with satisfaction, knowing she
11:05recognized potential in the
11:07transformation. Auntie, I'm truly
11:09grateful for your help. I already feel
11:12wonderful. Do you think I'm simply a
11:15I inquired with amazement,
11:17reveling in the sensation of being
11:19dressed so elegantly. It surpassed even
11:22my wildest dreams. Listen, sweetie, I've
11:26never had an opportunity like this
11:27before. I'm actually looking forward to
11:30it. If being a girl is what you want,
11:33then a girl is what I'll help you
11:35become. Making you convincingly pass as
11:38a girl will be a challenge for both of
11:39us, she pledged, snapping another photo
11:42as a reminder of my first moments in
11:44skirts. With these encouraging words, a
11:47lovely pink teenage dance dress slipped
11:50over my head and zipped up the back.
11:52Matching pink pumps with 2-in heels
11:54followed, and then she draped a frilly
11:56pink makeup cape around my shoulders.
11:59Auntie placed her arm behind my neck as
12:01she applied lipstick to my lips with her
12:04other hand. Swiftly, she affixed false
12:07eyelashes, trimmed to fill in where mine
12:09weren't as full as a girl's. A touch of
12:12eye makeup and blush came next. She
12:14styled my hair into a feminine coif
12:17before removing the cape to add clip-on
12:19gold earrings, a charm bracelet,
12:21necklace, and a woman's watch,
12:23completing my transformation. She then
12:26escorted me to the full-length mirror to
12:28admire how lovely I looked while
12:30snapping more photos for her collection.
12:32Jenny, be a dear and change out of your
12:35dress now. I'll help you unzip. Once
12:38we've applied a bit more makeup, we'll
12:40outfit you in another ensemble, and I'll
12:42take more pictures for you, perhaps to
12:44share with your mother, Sally, or Nancy.
12:47You'll truly experience what it's like
12:49to be dressed as a girl all day, every
12:52day. If you'd rather switch back into
12:54your boy clothes now, feel free to do so
12:56if you can find them. Otherwise, you'll
12:59need to stay in girl mode for the entire
13:01week, she chuckled. Then, noticing my
13:03contemplative expression in the mirror,
13:05she continued, "Young lady, Jenny, are
13:08you certain about what you want? How
13:11often have you dressed up as a girl
13:13before? Perhaps I should offer you
13:15lessons on being a proper girl, so
13:17you'll know how to look and behave
13:19charmingly. If you truly wish to look
13:21elegant, you'll need to let me train you
13:23correctly. Auntie couldn't suppress her
13:26giggles as she sifted through the
13:27clothing strewn across the bed, while I
13:30patiently awaited the next outfit she
13:32wished me to try on. My makeup was
13:34touched up, expertly applied in a
13:36glamorous manner, far more
13:38professionally than I had anticipated.
13:41She had me rehearse dressing, each time
13:43outfitting me in a different combination
13:45of panties, stockings, a panty girdle,
13:48padded bra, full nylon slip, and black
13:51high heels with straps. Following a
13:53spritz of perfume, she guided my arms
13:56through the sleeves of a silk blouse,
13:58which she proceeded to button and zip
14:00up. Auntie demonstrated the proper way
14:03to sit with my skirt neat and my legs
14:05crossed. Auntie instructed me on
14:08adopting feminine mannerisms, walking
14:10gracefully in high heels, and
14:12efficiently applying makeup. She
14:14emphasized that femininity was a state
14:17of mind rather than a physical
14:19attribute. She assured me, "I'll assist
14:22you until you're a flawless little
14:23lady." She snapped an entire roll of
14:26photos of Jenny in various poses and
14:28outfits. Before we knew it, it was time
14:31for me to change into a nightgown and
14:33retire to Sally's room, which was
14:35designated as Jenny's room for as long
14:37as she remained in petticoats as Auntie
14:39Margaret's niece. I relished being
14:42attired and treated as a girl. The
14:44expert guidance and encouragement made
14:47me feel absolutely marvelous. Falling
14:49asleep with my hair in curlers, I
14:52dreamed of my new life as a girl. The
14:54following morning, as she woke me, she
14:57skillfully supervised my dressing and
14:59makeup routine. I wore a knee-length
15:02princess style yellow cotton dress, and
15:04she remarked that I would remain a girl
15:06for the entire day, suggesting that
15:08perhaps my parents would appreciate
15:10seeing what a beautiful daughter they
15:11had. As we descended to breakfast, which
15:14she designated I was responsible for
15:16preparing, she retrieved her video
15:18camera, explaining her intention to
15:21record me in several different outfits
15:23throughout the week as I experienced
15:24life as a girl. She intended to review
15:27the footage each day to provide me with
15:29better coaching and aid my development
15:32as a girl. I'll keep guiding you on how
15:34to refine your mannerisms and walking
15:36style while you perform the household
15:38tasks I'd anticipate any girl to
15:40undertake. Then, after dinner, I'll
15:43offer you additional lessons in
15:45femininity. It's truly delightful to
15:48dress you as a woman. I eagerly
15:50anticipate maintaining your polished
15:52nails, ensuring your body remains
15:54hair-free, and guiding you in embodying
15:57femininity. You'll dedicate hours to
15:59mastering the art of walking, speaking,
16:02and behaving like a woman. Perhaps you'd
16:05even like to venture out in public as a
16:07girl, though you'd need to use the
16:09ladies' room exclusively. I'll
16:11demonstrate how to manage your skirt and
16:13slip to ensure they're out of the way
16:15while using the toilet, just like a
16:17woman. There's a lot for me to teach you
16:19about womanhood. Dressing you up is even
16:22more enjoyable than I anticipated. It's
16:25all about having fun. You enjoy wearing
16:28nail polish,
16:30and high heels. You admire the beauty of
16:33girls who indulge in such things. You
16:35yearn to be a female just like them. So,
16:38what does it matter if you're a boy? Not
16:41everyone finds males in panties, bras,
16:44and dresses appealing, but as long as it
16:46brings you joy and I find fulfillment in
16:48assisting you, let's revel in it
16:50together. I'll allow you to embody the
16:53woman you pretend to be. Are you
16:55relishing being compliant and willingly
16:57accepting my efforts to dress you as a
16:59lady? I might just send you home in a
17:02lovely feminine ensemble, so everyone
17:04can perceive you as Jenny. By then,
17:07you'll have acquired more of the
17:08subtleties of womanhood, from applying
17:10makeup to strolling through town in high
17:12heels like a woman, perhaps even
17:15receiving whistles from men unaware of
17:17your true identity. I eagerly
17:19anticipated Auntie Margaret guiding me
17:21through a week of womanhood. On Saturday
17:24night, at the conclusion of the first
17:26week, as she assisted me in preparing,
17:28she declared her intention to truly
17:30glamorize me for our evening out as a
17:33token of appreciation for being her
17:35niece all week. She guided me through
17:37another perfumed bath and once more
17:39shaved off any remaining boyish hairs to
17:42catch the ones we missed earlier. She
17:44laid out all the attire she wanted me to
17:46don. I couldn't help but feel feminine
17:49and girlish. Auntie handed me a pair of
17:52black silk panties. She fastened a black
17:55lace bra behind my back, adding silicone
17:58inserts to enhance the cups. The bra
18:01perfectly matched my panties. The gentle
18:04weight of the bra straps was delightful.
18:06Next, she fitted me with a waist
18:08cincher, which nicely shaped my
18:10waistline, followed by a black panty
18:12girdle with padded hips to lend me a
18:15feminine silhouette. She then secured a
18:17black lacy garter belt around my waist
18:20and proceeded to roll seamed nylons up
18:22my legs. You must be feeling quite
18:24alluring by now, she remarked. Those
18:27black nylons look incredibly seductive
18:30on you. Auntie adjusted the toes of my
18:33nylons, subtly revealing my polished
18:35toenails. She slid the open-toed heels,
18:38featuring slingbacks, onto my feminine
18:41feet, mentioning they would be suitable
18:43for an evening outing. The heels were
18:45moderately high yet comfortable, crafted
18:48from white patent leather with 4-in
18:50heels and buckled straps. I delicately
18:53eased my feet into them, relishing the
18:55wonderful sensation as my polished
18:57toenails peeked through the open toes of
19:00the shoes. Auntie crouched down and
19:02fastened the straps, then instructed me
19:05to rise to my feet. I wobbled slightly
19:08before making my way over to the vanity
19:10table and taking a seat. I felt
19:12incredibly feminine in my high heels and
19:15eagerly anticipated donning my lovely
19:17dress. Aunt Margaret retrieved the long
19:20black slip from the bed, instructed me
19:22to slip my arms through the straps, and
19:24then pulled it down over my shoulders,
19:26smoothing it over my body. She admired
19:29my girlish appearance as she began
19:31applying my makeup. Auntie applied a
19:34frosty blue shade to my eyelids,
19:36penciled in my eyebrows, affixed long
19:39false eyelashes, and applied eyeliner. I
19:41felt incredibly feminine as I blinked
19:44with my false eyelashes. Next came blush
19:47on my cheeks, expertly feathered out
19:49with a the
19:51A gold necklace and dangling earrings
19:53adorned me just before Auntie placed my
19:55curly blonde wig on my head. "You'll
19:58have more fun as a blonde," she assured
20:00me as she sprayed my wig with hairspray.
20:03Soon, a delightful, pretty woman stared
20:06back at me from the mirror. I cherished
20:08being Jenny as Auntie assisted me into
20:10my long-sleeved frilly blouse, buttoning
20:13it up the back. With care, she helped me
20:16step into my skirt, ensuring not to snag
20:19it with my heels. It was a dark, slim
20:22skirt matched with a coordinating
20:23jacket. She fastened the buttons and
20:26zipped me up. "Now, no one will suspect
20:29you're a boy," she remarked as she
20:31applied fresh lipstick to my lips. After
20:34she finished, we departed in the car,
20:37ready to explore the town as an aunt and
20:39her visiting niece. My confidence
20:41surged, feeling capable of successfully
20:44embracing my new female role. This was
20:47not the end, but rather my new
20:49beginning.

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