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Experiences Of A Crossdresser

This is an introduction to my crossdressing experiences – touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever.I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like slips and sheer blouses. I would typically be drawn to anything black, but did have a fondness for nude tights and white slips, also. I usually...

How I became Jayne The Crossdresser

It started in 1976,around August,I had just met John a guy my around my age,who lived alone near me. He wasn't shy to admit he was gay,and I was curious,and I told him one Friday after we got back from the pub about my interest. Before I knew it John & I had undressed & I had Johns cock in my mouth,sucking him off,& he soon quaked into an orgasm,cumming in my mouth so fast I gagged slightly before I managed to swallow most of it.John was keen to make it a pleasure for me &...

firsts time I m seen as cd crossdresser

From a young age I liked dressing up in womens lingerie and clothing.... as I got older I grew up over weight a little and more so the older I got..... by the time I was I was in my late teens I had nice size breasts....nice enough to fill a bra. So worked up the courage to buy some lingerie online and when I received it in the mail I was so excited. I couldn't wait to try everything on.... I had brought a white lace bra, matching panties and white suspenders and stockings.....I tried them...

Motel Fun for College Crossdresser

Before I start the story I want to describe the setting so you get a better idea: it's a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that's for sure. The layout of the motel is a rectangle. The rooms surround the rectangle's perimeter, in the center there is a pool, a park area, and a parking lot. There is a walkway around the entire inside perimeter of the rectangle and every room has two doors, one facing the exit and...

Crossdressing

Natural Ingredients for a crossdresser

It was still snowing outside and I wasn't going to be recieving any visitors today so I decided to treat myself and while the day dressed how I wanted.... I had set the heating up high at my place, so I could wear one of my sexy side tie bikinis which show off my sweet little ass so well. Having enjoyed the view in a full length mirror and got some self shot snaps, I found myself sitting at my dressing table wondering how to amuse myself next.... Looking at my face in the mirror I noted a...

Patni Patni A Crossdresser

“Oh Ramesh! I am so happy that you came today.”, I pressed my boobs against his chest and wrapped my arms around him, as soon as Ramesh entered in my flat. And he grabbed be in his arms too like a real man. He began to touch my body and moved his hands all over my back and lower waist. I was titillated by his sensual touch. “Where else I could be, my darling.”, he said and slowly slipped one of his fingers from the back of my saree blouse. He was feeling my bra strap with his finger. We two...

transforming into ashley crossdresser

durring the day,i'm working i'm dressed in my work clothes,but when I come home I take a hot bath washing all over my body,then shave my legs,arms chest,and face.I even add babyoil in the water so that my skin becomes soft.then I will clean myself ass inside/out.then as i'm drying off i'll start ptting on my makeup,this takes me about an hour,I like taking my time so that my makeup looks perfect,so that when I put my wig on I'll have that female look.then go in the bedroom pick out something to...

First Time With A Hot Crossdresser

My email id is Please contact me for any queries, doubts or proposals. I usually work late nights, and leave home by 1 am. I take a rickshaw for home, which happens to cross this one spot where post-midnight you usually find young crossdressers here on business at the side of the road. They are dressed mostly in skimpy western outfits, some of them are really attractive. That’s saying a lot coming from me, for a 26-year-old straight guy. I’ve never been bi-curious either. It’s been months I’ve...

Gay Male

A Tale Of Crossdresser

Hey, this is my first story that I am writing but not definite new to the glorious crossdressing field, Kindly forgive me if there are any mistakes, suggestions are welcomed people who are moving to Bangalore or in Bangalore if they want to my friends or a hook up we a cross dresser can contact me at m First, I don’t have a perfect girl figure but I wanted to be dressed as a girl, do a girl activity from a long time but it didn’t come true. I always used to wear my mom’s clothes like bra &...

Gay Male

Party Surprise First sex as a Crossdresser

This is a work of Fantasy. I hope you enjoy.Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly she was jealous of my legs. She was a petite sexy woman and we were almost the same size but I still had my own stuff that I’d secretly obtained from eBay and op shops.I didn’t consider myself bisexual,...

Made My Friend A Crossdresser

I am having a tsunami of mixed feeling about this friend of mine who’s name shall remain anonymous but for now lets call him Anshul. He’s a good guy and a hot one. He got flawlessly creamy skin with awesome bubbly butts. This started a few years ago when we met for the first time in India. We worked in same company and he was a friend of a friend. At that time I was crazy about my physique and was well built up and he got motivated and asked about my workout routine and slowly he started...

Gay Male

A great experience as a crossdresser

Note: ——I am NOT the author!so plz Don't ask me about part two,am simply sharing this lovely story with all of you because I have not seen it on hereI was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie.I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and...

A great experience as a crossdresser

I was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie.I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and wearing sexy lingerie.One of my early experiences was when I was 18 going on 19. I had been to a thrift store and purchased several items of ladies...

Beauty And A Crossdresser

Hi this is hotslutaddy back with my friend ishika’s story. Hi this is ishika. Those who have read my first story “lost virginity from behind” in virgin archive should know that I am a cross-dressing bottom gay.It had been 8 months till that incident and I had completed my schooling. Kartik had become my boyfriend and I love him more than my life. Now I was in a college in a nearby town and I lived at a house on rent. I lived alone there so I had an almira full of female clothes and make up.Most...

Lesbian

Telling Mom I m A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

Crossdressing

The 2nd Halloween for a Boy Dressed as a Girl Part 1 A Blissful Young Crossdresser

5th Grade. 11 years old. Dressed as a girl again on Halloween. As a cheerleader. My next old sister's cheer uniform. Her idea. Her bra and panty too. My special "Boob" socks to give the appearance of breast. A discussion I had with my next 2 older sisters. How ample were my false breast to be? Normal size for girls my age? Bigger for my ego as a girl, for all the times I have dressed up with them through the years? Dolly Parton size? Because my 2nd oldest sis Joan, made...

SALLY S RELUCTANT CROSSDRESSER

CHAPTER ONE Sally and Dave had been dating since high school, it was a turbulent relationship, and at this moment in time they were having a few arguments, Sally called them dicusions. They were both nineteen and in love with each other, and both were jealous and possessive of each other. Sally was the one with the ideas, and Dave let things fall into place as he could never emulate her suggestions. They were sitting in the lounge of the flat they rented, they were not married...

indian crossdresser

hiiiiiiiiii every one here's kiran from india ,punjab first of all its not a fictitous story ,it is a real part of my life my actual name is rahul and me a guy now of 20 yrs old. so lets start frm my age of 12 yrs............................... me frm starting was very likely to kiddish me always remain at home .not to go any where else than in my street. in mid of june when our holidays were going on my parents were with at home ,i asked them about there relationship .they bit were not happy...

Crossdressing

A great experience as a crossdresser

I was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie.I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and wearing sexy lingerie.One of my early experiences was when I was 18 going on 19. I had been to a thrift store and purchased several items of ladies...

Crossdressing

The girl that wore a red dress

I have a small store in the city there is this young lady that pops in ever day now dont know her she is about 16 maybe she is tall with long legs and wears high heels the kind were you can see the foot and toes and a short dress she hads long black hair and she comes in about the same time every day and gets a coke she makes my dick hard just looking at her she smells great so one day she came in I put a candy bar in her bag I started to yell at her telling her you Steel candy she said I did...

The Silver Dress

It was Friday night. My wife and I often go out for dinner on Friday night. A new place had opened up not too far from our home. There was a piano lounge in front, and some tables for dining at the rear. The place was advertised as having a quiet and relaxing atmosphere, suitable for a sexy cocktail dress or dressy blue jeans. I mentioned the sexy cocktail dress because that’s how it all started. My wife was successful and beautiful, a five foot nine brunette with B sized breasts and womanly...

Caught in a Prom Dress

If you can remember the stories LUCK RAN OUT AND I GOT CAUGHT then good this has escalated from there if not please read it first. It was a few weeks before my G/f college prom and said had her prom dress all prepared and hung up in the spare bedroom where i stayed. (her folks where very strict) As you can probably guess by now i wanted to try it on, it was a gorgeous gold long dress with 7 layers of skirt from the outside it felt so good but i wanted to feel the inside, so there i was...

The Ring AOChapter 51 Getting the Dress

On Monday Morning Julie picked up Helena, drove to Suzanne and they went to the bridal shop for their final dressing. Again Julie had a few tears for her favourite clients. They looked out of this world in their wedding dresses. They packed their dresses in suitable suits and returned to the Hilton for lunch. They made plans for Thursday. Suzanne would stay overnight with Helena and dress there. Helena would take the dresses home and place in the 2nd bedroom. As Helena requested Suzanne to...

I Begin to Undress

I begin to undress. Trying to think of other things, other than sex, other than the beautiful woman standing in front of me, telling me to undress now. "I have to be able to asses your ability to hold a pose, and I suppose that you are comfortable enough naked, when I'm not. That you won't, well, chicken out on us, on the night.""Uh, sure, um, I just wasn't expecting to that's all.""Well then."I stood, sort of waiting for her to insist, or to produce a screen."Is there a screen?""Well, yes...

Christmas Crossdressing

Over the Christmas holiday I was in the gay adult book store and some big old white guy asked me to go to a gloryhole booth. I went in and he went to the other side. I popped in my quarters and as I was unzipping my pants an old floppy dick came through the hole. I just heard “suck it boy.” I licked the head and watched it raise and raise and raise. The more I sucked the fatter it got and I was honestly surprised, he was a good 8 inches. He started pumping his dick through the hole into my...

My journey into crossdressing

The following story is 100% true. Only the names have been changed. About 11 years ago, when I was 28, I met a 40 year old single mum of 2 called Michelle. We met through a mutual friend. The relationship was purely a sexual relationship. I had just broken up with my girlfriend of 3 years, and she had been single for 7 years after splitting with her violent ex. The first day we met, we ended up sl**ping together. As we lay in bed afterwards, we started talking about what we liked and didn’t...

Mom finds son crossdressing

Your mom is away a lot with her friends and she has recently divorced her husband. Right now she's away with her friends to celebrate breaking loose from that bastard and getting back on the market. Your older sister is 26 years old and just bought an apartment a couple of towns over. When moving out she found a bunch of old clothes she didn't want anymore so she left them at home for your mother to send to some charity. Now, you're home alone, your mom isn't coming home tonight since she's...

Incest

Caught crossdressing

The below is a true story so naturally names and places changed but the rest of it remains to be one of my memorable moments!!What seems like many years ago now when I finished university my then girlfriend Lexy and I went down to Cornwall to stay in her parents holiday home for the summer while we worked out what to do. To be honest at this point we both know that we aren’t “the one” for each other but I think we both had the same thought, see what happens over the summer and then make...

I was his bitch first time crossdressing

My growing curiosity was really starting to take control. I've spent so many years married, hiding my true thoughts and fantasies about sex.My wife and k**s were going out of town a couple of weeks ago and I was going to explore more of what I wanted. As the day they were going to leave got closer, my pulse would race and my palms would sweat.I just hoped I wouldn't chicken out.Finally, I dropped them off at the airport and as soon as I did, I was freaking out. Just thinking about visiting my...

My journey into crossdressing

The following story is 100% true. Only the names have been changed.About 11 years ago, when I was 28, I met a 40 year old single mum of 2 called Michelle.We met through a mutual friend. The relationship was purely a sexual relationship. I had just broken up with my girlfriend of 3 years, and she had been single for 7 years after splitting with her violent ex.The first day we met, we ended up sleeping together. As we lay in bed afterwards, we started talking about what we liked and didn't like...

Christmas Crossdressing

Over the Christmas holiday I was in the gay adult book store and some big old white guy asked me to go to a gloryhole booth. I went in and he went to the other side. I popped in my quarters and as I was unzipping my pants an old floppy dick came through the hole. I just heard “suck it boy.” I licked the head and watched it raise and raise and raise. The more I sucked the fatter it got and I was honestly surprised, he was a good 8 inches. He started pumping his dick through the hole into my...

caught my son crossdressing

I had come home early from work and found my son, Jamie, sitting at my vanity, putting on make-up. He was wearing one of my cocktail dresses -- and my stockings, my high heeled sandals and, it appeared, my lingerie. He hadn't heard me come in, so I just stood silently in the doorway watching him put on mascara, blush and lipstick. He was completely mesmerized by his own ladylike reflection, completely entranced by the girl in the mirror. He did a very good job with his make-up; clearly he...

My Early Crossdressing

I started cross dressing around 12. At first it was knickers or tights. As I got older I started to get more serious with it. Just after I turned 16, I'd often go out round the streets round town dressed in full girls clothes. I'd always prefer going out late in the evening in winter, as I'd not pass many people and id normally only pass a few cars, some would slow down as I walked along the side of the road.One day I was home alone, my parents were away for the week and my sister was staying...

my first cock experience true story crossdressing

I will never forget my first experience with another cock , it was the only time I have ever been with another man, now saying that I do date ts women, I love them as much if not more then I do genetic women. I was 12 years old and like any young boy , very horny . At that time my best friend liam and I would have sleep overs and do normal k** stuff , sports , video games , camping , never did I think that one day I would have his warm milky cum in my mouth or his warm hard throbbing Dick...

Crossdressing

Hi back again… This is my friend new story. I met him in London last week .his name was mike. So let start… It all started a few weekends ago when I (mike) had been incredibly horny and my girlfriend was out of town. She wasn’t expected to be back for another two days and I needed some relief. She always wore really sexy panties and I loved the way they felt when she would grind up against my bare cock during foreplay. Being as horny as I was I went to the dirty clothes hamper and found the...

Gay Male

Friday night crossdressing

Silky long sleeved blouse and skirt? A dress? Or just lounge around in my lingerie. Parking my truck my anticipation only grew to full out excitement, a huge smile was plastered on my scruffy face. I was almost skipping up the sidewalk. I'm sure some of my nosy neighbors saw me but I didn't care. It was a long week to hide Lisa within me. Once inside my apartment, I quickly got undressed from my work clothes and stood in front of the floor length mirror to admire my lingerie I always...

My first time going out as a Cross Dresser

MY FIRST TIME OUT AS A CROSS DRESSER A true storyIt was 14 years ago and I had been married to a beautiful petite woman she had long Cole black shiny hair with green eyes.. We had been married about a year and one night I came out playing around in a pair of her sexy blue panties and a sexy blue Teddy and started rubbing on her and having fun it made her so hot we both had the best sex we ever had in our lives.. The next Friday when I got home there was a bag on the table she told me to open...

How Hockey predisposed me to be a Cross Dresser

I had a thought the other day, my hockey equipment has a number of striking similarities to lingerie!To set the stage, I am a cross dresser. Like most of us, I love everything about ladies undergarments. I like seeing lingerie in stores, on models, on women, on men and of course on me! I love the feel when I am dressed up. I love the taboo of wearing them. I love the thrill of being "underdressed", that is wearing lots of lingerie under your manly clothes, when I go to work. I especially...

Tea party for a cross dresser

I decided I'd walk over to her place. It wasn't far and it was a nice day. Once dressed I picked up the bag and headed out the door. I arrived just before 8. She answered the door in her dressing gown. "darling" she said and we kissed each other on both cheeks as I entered. I stood in the hall. The flat had high ceilings. We went to the kitchen. We discussed proceedings over tea and toast. Showers were a must. I had a lot of shaving to do. That would take some time. There was one...

Window Dressing

Window Dressing By Rubberwolf 2009?Story codes: f, reluctant, stuck, bd, toys.Angela had been working at the department store since she left college five years ago. She had picked up various qualifications to do with retail since then, but the main thing that had gotten her off of the shop floor and into window decoration had been her diploma in fashion, along with an A level qualification in art. She had started in underwear, but after a year, her flair for art and arranging displays had...

Summer Dress

She was wearing a light blue checkered summer dress that stopped right at her thighs and looked very sexy on her. I was standing at the door looking at her walk to the car. ”Hey baby, we need some juice also, I said to her as she walked down the path. “Ok, boo,” she said back to me, her sunglasses now on, looking sexy as hell as always. Then she did something I was expecting. She looked over her shoulder, lowered her glasses slightly gave me a kiss turned away and then lifted up her skirt and...

Cross Dressing

It was the early 80's and I was over my friends house who's dad had a ton of porno mags in his laundry hamper in his bathroom. We used to look at it while his mom and dad were at work. We loved the looking at the hot girls but what got me the hottest were the guys who dressed as girls. When we couldn't take it anymore we would jerk each other off but I was the only one willing to give head. At 18 years old these guys would explode down my throat. What really got me off was when I would go...

Head Dressing

"Head Dressing" The title of this short story is a bit strange but it's a punishment the neighbor lady made up and later I was to suffer. But before I get ahead of myself I will start at the beginning. I was a typical teenage boy living with my step mom in a modest duplex apartment. We had a neighbor lady named Madge who lived in the apartment next door. I was just learning about women and would always notice Madge when ever she would come over to have coffee with Ruth. I always...

Blowjob in a Housemaid dress

There you are. In the bathroom of the hotelroom you took to explore your kinky side. You always wanted to know what its like to suck a cock and take a load. Something about Dicks seems to mesmerize you. Because of that you decided to take a hotelroom over a weekend and see if you find a seizable cock to blow the night. To top if of you even bought a housemaid dress, wig and some make-up to look more feminine for your lover. After you posted the ad, it didn't took long for several guys to find...

Gay

The Yellow Dress

She’s wearing a yellow empire waist dress with black swirls and flowing patterns with black Mary Janes. A black sash runs under her breasts and ties behind her back. Her breasts are high and he realizes she’s not wearing a bra. He can’t tell if she’s wearing panties either and this makes him hard. She walks over to him and he likes the way the skirt softly twirls around her knees. He’s sitting on the couch and moves slightly as the pressure of his growing erection is making him uncomfortable....

Toys

Molly Starts To Dress

Molly Starts To Dress By Molly Zed It's midnight; his girlfriend is away and unlikely to call, It's time for the crossdressing, transvestite teaser, Sissy Molly to come alive! Pulling on her sheerest seamed nylon stockings, yes the barely black ones with the pretty lace tops mmmm the electric sensuous feeling of nyloned legs. Carefully she attaches each stocking top to the suspender straps dangling from her Purple PVC corset, mmm yes the same PVC corset that is pulled...

I Too Can Dress

(Author's note: I'm not trying to be morbid or anything, this is just more like what I'd expect here on Fictionmania. Not for the weak of heart. Then again, most of you read femdom stories anyway.) I, Too Can Dress! by Androgynous Bosch See Jane. Jane is a girl. Jane is very big. See big girl Jane. See the ball. See the other ball. See the two balls. See the dick. Up, dick, up. Dick is big. Dick is very big. One ball on Jane. Two balls on Jane. Dick on Jane. Dick...

The Fall of Brooklyn ch09 Party Dress

The lights came on but there was no music this time. It was the older girl from last night. She hit the cage doors. "Empty yourselves out, I don't want any accidents tonight." The other two girls on her row moved to the back and Brooklyn followed suit. As she flushed and looked up she saw the redhead moving down the ladder with her practised grace. As she moved to the front of her cage her door was opened and Miss walked away, leaving her to awkwardly climb out on her own. Herding them...

Wedding Dress

Copyright© 2006 by Kien Reti A close friend told me the following, in strictest confidence. I have reason to believe that the events depicted actually happened. Dana was having that dream again. So very exquisite in that dress, the one with the white lace, the bridal gown. (Oh! How cute! All the women standing round had sighed.) The reception had just ended and in scant moments John was going to whisk the two of them away in his gleaming white Studebaker convertible to the rented cabin...

GoddessChapter 7 The Night Hebe Fell Out of Her Dress

HEBE DIDN'T BRING THE HOUSE down the night she fell out of her dress, but it was a close call for a few minutes. Oscar had his hands full. Jacob and the other bouncer, plus me and Rick and Persephone, helped. After we'd untangled ourselves that afternoon, Hebe got out of bed and stretched, her joints cracking and her breasts rising as she extended her hands above her head. In his cage by the window her parakeet, Jupiter, chattered. "I'm going to do it tonight." I was sitting on the...

Mom Undressing

This is a story i like and would like to share with you all if you like you can find more here https://www.literotica.com/storiesMom Undressing For the last 7 days I have been working every evening and missed the best part of my days. Today I was at home and had a GREAT seat when Mom came arrived.She walked in and we exchanged hugs and kisses then began the ritual of telling how our day went as I watched the best ass in the world walk towards her closet to get to what I had been anxiously...

First Time Dressing

My first time didn't actually start out as a 'solo' experimentation as it seems like so many other girls' first times. It didn't start out as raiding the laundry basket of a mother, sister, neighbor, or girl down the street; finding a pair of pantyhose in some trash container; or even reading about crossdressing in some stashed away porn magazine. In fact... my first time was actually like something out of a fantasy story somewhere... you know, those stories you read where boy meets...

Me My Uncle And Cross Dressing

This is my story. The story about my introduction to the sex world. Hello guys i m Ankit from Hisar, Haryana. This story is from my past or i should say this a biography. It was all happened when i was in 12th class. But i m telling it in present tense. I am slim and cute. We are 4 members in our family. My parents, my older sister and me. We are living at the end of the city in. My uncle lives next to our house. He live alone. He is retired from his job and living a luxurious life. He is very...

Gay Male

The Address

So, again....these are a few cell phone stories I had to send to a friend. When she and I were in our younger 20s, she turned me out. She showed me what sex is REALLY supposed to be like. She moved a few states away and we lost contact. She searched me out when she moved back to the area and of which, we are now in our late 40s. She was still as hot as ever and was curious to see if her student had learned anything new. Well....THIS time....I turned HER out. I showed her what sex could REALLY...

Journey From Disney To Sundress

Philip Johnson It started out with the four neighbors gathered on the back deck talking about a little bit of everything. That is until the subject of Disney World came up. When Kristen commented on how badly she wanted to go, that got Joanne going and she said the same thing. Then Charlie, Kristen’s husband sealed it when he said, ‘I think the four of us should go and do it soon.’ ‘Can the four of us get vacation at the same time is the first issue,’ was Jess’s comment and on they went...

Trying on Sallys new sundress

I watched Sally wiggle her skirt to the floor. She had already removed her top to expose a cute black bra. I was treated to a nice view of her decolletage as she bent over to push down her skirt. My cock began to harden in my jeans as I examined how the pale skin of her breasts met the top of her bra. Her covered breasts hung and jiggled enticingly as she bent over. I shifted my stance as my groin started to become tight and uncomfortable. Sally stood up and stepped out of her skirt, she...

Nipple Rings A SunDress

I spent the morning doing what I always do, classes first at the local college I attend, and then off to breeze by Dads office to bring him lunch, and today I thought perhaps Id go to the gym and work out for a bit. I pulled my Honda into the parking garage at Dads office, I adjusted the mirror to put on some lip gloss and ran my fingers through my hair. I grabbed the Chinese I had picked up for Dad. I locked the door and walked to the elevator. I pressed the button to the elevator and the door...

Started as cross dressing

This is my true story that happened with I was 26 yrs old. I am currently 28, married for 4 yrs now. I have been a horny guy every since I was in my 6th class and was always turned on by girls. I even made full use of the opportunity of co-ed and used to have fun with most of the innocent girls. I got married when I was 24 to a girl who was two years younger to me. She was a typical traditional girl with a very reserved and religious view of sex. She hardly liked variety and soon I discovered...

Cross dressing

Hello is my story. This happened. It was the mid 80’s and I just turned 17 so I thought I would go to the mall near my home town on Long Island and go shopping with my birthday money. I was looking for clothes with and I need to use the rest room. I walked into the bathroom, and the floors were wet so when I made a turn, I slipped. I put my hand against the door of a stall that was closed as not to fall, and the door it flung open because it was not locked properly. I looked inside and a man...

Angela Undress

I, Mitchell Ryan Magnuson, born February 2d, 1959 in The city of Joplin, Jasper County Missouri, declare this Document to be my last will and testament, there being no others. Being of sound mind and unbelievably unsound body do herein state: 1. My attorney, Norman Atchison, is the executor of this will. He shall serve without bond and has discretion in the execution of this will. 2. I require of my executor that he arrange for my burial at the Grainger, Kansas Cemetery. Norm, I’d like a...

A tale of two wedding dresses

I have never been married but I love seeing a sexy bride and imagining the lingerie underneath etc. Anyway a few years ago I hooked up with a married woman, Sara,who was in the middle of getting separated/ divorced and we or rather she would have some serious angry sex on a weekly basis. We got around to talking about fantasies and I told her of mine, about stripping a bride down to her lingerie and fucking her in white. Well, up the stairs she went, came back down in a big meringue dress and...

Fun with a cross dresser

I had a really good experience with a cross dresser yesterday. A mutual friend had recommended him after enjoying his services so I got in touch and he immediately responded by inviting me to go and meet him. It was most enjoyable. I have never been with a CD before but he seemed okay. He is late 50s and very slim. It was really quite strange. He came to the door in a dressing gown and invited me into the lounge where he explained how he had got involved in all of this by dressing up in his...

Me Mom and the Hair Dresser

Growing up as a only c***d I was smothered by my Mother, I don't know if it was normal ,but at 14 she was still breast feeding me,bathing me, and sharing one bed . I was a very shy boy, we moved every year so I was always getting beat up at the new school. I had no thoughts until my 14th birthday. It's funny how these things change so fast,I had received my first computer, I was looking up and typed in the words "Mother and Son" I was directed to a porn site one of the pictures was of a mature...

My First Time with a cross dresser

Growing up, like many children I went through phases. I would climb trees and play football, then as I reached my mid-teens I continued these phases but also became a lot more sexually aware, thanks to the porn magazines and porn films usually belonging to my mates dads or older brothers.Now I am in my late teens and at college.One day my Dad made a pot of tea and breakfast.“Did you sleep well, son?” he asked as I entered the kitchen.“Not bad thanks, Dad, how about you?” I replied.“Pretty good...

Crossdressing

How I Became A Paid Cross Dresser

Hello friends, without making you feel bored directly coming to the story. It was the time when I was in need of money and I asked my friend Rahul. He told that he will help me and when I met him he told me that I have to work his boss. I asked what kind of work then Rahul said that his boss is a bisexual who prefers crossdressers more than gays. Me:- so what I should do for your boss Rahul:- don’t get me wrong, you said that you were in need money so am telling this. You need to get dressed...

Gay Male

She d Left No Forwarding Address

Fleeting love lost and then found again a decade later. A brief, ill advised affair that couldn’t possible have been more than it was—couldn’t in a million years be the basis for anything that might endure. Romance as the top priority with enough sex to keep things interesting. As Lisa pulled her ocean blue Travelpro Crew6™ down the jet way, her thoughts drifted back a decade. She was a magna cum laude graduate of one of the country’s most prestigious private women’s colleges, Ivy League in...

The Wrong Address

Luke checked the address he had written down. It was the right block of flats so he went to the front door and was about to press the entry button when a young woman came out. Luke smiled at the woman who smiled back and held the door open for him.“Thank you,” Luke said, still smiling.The young lady smiled back but didn’t say anything as she walked away from the flats.Luke walked in and closed the door, went to the stairs and started to climb up. He got to the second floor and saw the flat he...

Spanking

The Wrong Address

Luke checked the address he had written down. It was the right block of flats so he went to the front door and was about to press the entry button when a young woman came out. Luke smiled at the woman who smiled back and held the door open for him.“Thank you,” Luke said, still smiling.The young lady smiled back but didn’t say anything as she walked away from the flats.Luke walked in and closed the door, went to the stairs and started to climb up. He got to the second floor and saw the flat he...

Spanking

The Benefits of FriendsChapter 24 The Valedictory Address

Preparing our valedictory address presented us with a few problems to overcome, not the least of which was that it had to be a joint presentation, since we had been named as the co-winners of the honour, albeit after a little nudge from us to the school administrators. We had started tossing realistic ideas back and forth a few weeks previously, and finally hit on what we felt was the perfect solution, especially in that it could be delivered as a 'duet' of sorts, with each of us taking on...

My First Time in a Dress

PART-1 When I was younger I used to go and stay at my grandmas house during the summer. It was a small country town with about 15,000 people. She lived on a quiet street and there was only a couple of other kids close to my age. I used to go and hang out with one guy, Dan who was about 3 yrs older than I and his sister, Pam who was my age. Dan and I used to go mess around everyday. His parents worked from early in the morning to around six to seven in the evening. One day we were out messing...

My First Time in a Dress

PART-1 When I was younger I used to go and stay at my grandmas house during the summer. It was a small country town with about 15,000 people. She lived on a quiet street and there was only a couple of other kids close to my age. I used to go and hang out with one guy, Dan who was about 3 yrs older than I and his sister, Pam who was my age. Dan and I used to go mess around everyday. His parents worked from early in the morning to around six to seven in the evening. One day we were out messing...

Crossdressing

Remembering that first time dressed

HI! I have been crossdressing since I was about 7-years-Old. Just the other day a lady friend of mine, (who knows I'm a crossdresser), anyway, she asked me how I first started dressing. She also wanted to know what made me put on a dress in the first place? It's funny, I haven't told that many people how I started out. I would just say that I was hooked with this great feeling I had as soon as I put the dress on. I was hooked so bad that I would steal and hide one of my sister's party...

My first halloween dressed

My First Halloween (Dressed) By tied2ava I had been invited to a Halloween costume party by a former co worker and had accepted even though my wife had refused to go saying her usual costume parties are stupid and a waste of time! After deciding to go I thought about what kind of costume I could wear? I thought of all the usual costumes vampire, bum, army solder, batman and so forth then came upon the idea of dressing up (I have been a deep closet cross dresser for years) I figure...

First time Cross Dressing

My growing curiosity was really starting to take control. I've spent so many years married, hiding my true thoughts and fantasies about sex.My wife and k**s were going out of town a couple of weeks ago and I was going to explore more of what I wanted. As the day they were going to leave got closer, my pulse would race and my palms would sweat.I just hoped I wouldn't chicken out.Finally, I dropped them off at the airport and as soon as I did, I was freaking out. Just thinking about visiting my...

Raunchy sex and cross dressing

Marcella and I were a perfect match. I was in my 40s and just out of a 20 year marriage with all sorts of sexual fantasies She was divorced, in her 30s and scaring guys off with her sexual desires, fantasies and needs. On our first date she was very touchy with her hands. We were out eating and she rubbed my leg and gave me a boner. There was something special (weird?) about her that grabbed me. When we got back to her place she gave me a women’s book showing pencil drawings of sexual...

When dressed

Properly start from down to above..When dressed I could never pass as a woman. I am clearly a sissy put into woman’s close. Love being sent out like that. Exposed. Knowing whoever sees me knows just what I am. I have only done that at adult bookstores and at adult theaters. When openly dressed there, either in nothing but lingerie and stockings and panties, or if I go in a skirt, stockings, blouse, bra and breast forms, it is not only clear what I am, but most men who enjoy sissies see it as an...

First time in full on cross dressing

From my last story, Fred, the man I met at the gay bar, contacted me again a while ago. He said he couldn't stop thinking about me. He told me had had other one night stands, but felt very comfortable with me. I was pretty flattered to say the least. Compliments are few and far between when you get to be my age.He told me he'd like to see me again. My heart started to race a little. I mean, this is still all new to me and suddenly I have a regular thing? He said he had some down time during the...

Dressed

I could never pass as a woman. I am clearly a sissy put into woman’s close. Love being sent out like that. Exposed. Knowing whoever sees me knows just what I am. I have only done that at adult bookstores and at adult theaters. When openly dressed there, either in nothing but lingerie and stockings and panties, or if I go in a skirt, stockings, blouse, bra and breast forms, it is not only clear what I am, but most men who enjoy sissies see it as an open invitation to use me. When dressed like...

When dressed

I could never pass as a woman. I am clearly a sissy put into woman’s close. Love being sent out like that. Exposed. Knowing whoever sees me knows just what I am. I have only done that at adult bookstores and at adult theaters. When openly dressed there, either in nothing but lingerie and stockings and panties, or if I go in a skirt, stockings, blouse, bra and breast forms, it is not only clear what I am, but most men who enjoy sissies see it as an open invitation to use me. When dressed like...

Dressed

I could never pass as a woman. I am clearly a sissy put into woman’s close. Love being sent out like that. Exposed. Knowing whoever sees me knows just what I am. I have only done that at adult bookstores and at adult theaters. When openly dressed there, either in nothing but lingerie and stockings and panties, or if I go in a skirt, stockings, blouse, bra and breast forms, it is not only clear what I am, but most men who enjoy sissies see it as an open invitation to use me. When dressed like...

Caught in the act of cross dressing

I'd been fantasizing about my day off for weeks, planning what I would wear and what naughty things I would get up to, home alone for the whole day. I hadn't jerked off in days as I wanted everything to feel that much more sensitive when I finally did touch myself.I woke up early and jumped straight into the shower, shaving my legs and arms, then rinsing myself off with soapy shower gel until I could feel the smoothness of my skin all over. After wrapping the towel around my chest and waist,...

First Time

How women undress

I do a lot of voyeur videos, initially testing techniques and cameras on my wife in our home. She was totally unsuspecting and would have gone ballistic if she knew. I now set up my new micro recorders in our guest room and bathroom to catch visitors who stay the night or visit the bathroom to urinate or shower.Watching other people's secret videos from locker rooms, store changing rooms and beach cabins I am always amused how the ladies undress. Little things catch my mind. How the dress can...

Forced Into Female Dressing

Hi everyone I am new on this site and this is my first pen downed story here. Please mail your responses @ All you girls reading this message it will give you lot of enjoyment as you read my experience. Please do mail me if you want to take the fun as they did. To begin with, my name is prince… Ya ya feminized prince. I am 21 yr old residing in Mumbai, slim and thin. After my graduation I started working. In our team of 5. Four of them were girls. To name them temporarily- sonia, seema, sana...

Lesbian

Daddy Issues 8211 Part 2 Issues Addressed

As I walked out of the bathroom, I knew what I wanted. I entered the hall found her checking notes on her calendar. She looked at me and smiled. I walked beside the couch and looked at the photographs of her family on the wall, old, new, many. They looked weirdly bright in the dim light of the chandelier coloring the room with a shade of yellow. I pointed at a picture on the wall, “Your dad is an exceptionally handsome man.” She stepped beside me and nodded, looking at the photograph tenderly,...

SRU Well Dressed

SRU: Well Dressed By Bashful Jack Edward Wilson was a relatively happy man. He had a good job and a wonderful wife. They had not been blessed with children yet but that was just a matter of time, he was sure. Jack really enjoyed his job, it was something he liked doing and he was good at it. He worked for a good company that treated it's employees well. You'd think he had the perfect life and you'd be right, except for one little thing. Jack wished he was a...

Sister Caught Me Dressed

Having her stay was limiting my dressing time and meeting people but it was my sister and she needed help. As we were having a meal, she cooked she told me that she would be going out with one of her friends and that she would be staying overnight. What a chance I had and decided there and then that would be spend the evening as Chloe and spend the evening dressed and on cam and chat with anyone who wanted to chat. When she had left with her overnight bag, I raced to get dressed to make...

Desperate Enough to Cross Dress

A couple of months ago I was on a business trip to a major city. I was looking forward to visiting the city and the opportunities that it should offer to have some extramarital fun, as I like to have some man-to-man action on my business trips. To my disappointment, the meeting was held at an office in a remote industrial park far from the city, where there was one lone hotel and nothing else but empty office buildings after-hours. I had to endure a business dinner at the hotel dining room and...

Gay Male

The Woman in the Insanely Short Dress

She stepped into the cross walk in front of me, and then, realizing that I might have the right of way, she quickly took a step back. She was wearing stiletto heels, and an insanely short flower print ensemble that just eluded sex appeal. She had gorgeous stockingless long legs and her black hair was neatly pinned up. It was about nine thirty in the morning in the downtown area of the small town in which I lived. Since I worked in the area and knew most of the shop owners and shop employees,...

Quickie Sex

That Summer Dress

“Damn,” she shouted to herself as her middle finger hit the delete key on her MacBook. She had spent the whole night trying to write her first lesbian erotic story for publication on the RedSite, which she had joined to express her sexuality. Mary had successfully written stories about straight sex but had set her heart on completing a lesbian tale. The frustration was evident. She was still learning her craft and despite never having been with a woman, she was completely curious about it.It...

Lesbian

Damsel in Dis dress

I am having marital problems for the past year and you have been my confidant at the office. Listening so attentively as I cry on your shoulder about the latest husband drama. You are consoling, gently suggesting I consider leaving him.After months of me sobbing out the same shit over and over, you finally say rather sharply-"for Christ's sake woman, why don't you just leave? You have no c***dren, nothing holding you there."This is when I burst into tears and through the sobbing I stammer out I...

Wrong Address

Well I guess that is one benefit of going away for a week, I have a big pile of mail waiting for me. I dumped the load on the dining room table and started sorting through it. Bill, bill, junk, junk, … not for me, not for me, … bill, not for me. Does the mailman use a white cane or a seeing eye dog? By the time I finished, the ‘not for me’ pile was almost as big as my pile. Mine mostly junk mail. They all had yellow change of address stickers on them. Sheila Johnson? What a screw up someone...

Wrong address

This adventure began with F****P delivering to the wrong address. I had purchased a sybian for my wife and was impatiently awaiting its arrival. Expecting it last week I was disappointed it hadn’t arrived. Monday morning the doorbell rang it was about 9:15. It was the lady that lived across the street. We knew each other to speak that was it. Her husband had taken a job assignment out of town for two years which ended up in them divorcing. She said hi, I’m Janet (not her name), I have a package...

Wrong Address

Well I guess that is one benefit of going away for a week; I have a big pile of mail waiting for me. I dumped the load on the dining room table and started sorting through it. Bill, bill, junk, junk, ... not for me, not for me, ... bill, not for me. Does the mailman use a white cane or a seeing eye dog?By the time I finished, the 'not for me' pile was almost as big as my pile. Mine mostly junk mail. They all had yellow change of address stickers on them. Sheila Johnson? What a screw up someone...

First Time Dressing

A few weeks ago my gay friend Paul phoned and asked if I would go out with him on Friday night. My husband John and I have known Paul for ages and we knew he was getting over breaking up with his long term boyfriend so I happily agreed. John stayed until Paul came round so we could all have a drink together and then he went off with a couple of his mates. After John left we had some more wine and then I went through to the bedroom to get changed. Paul followed me in and sat on the bed while I...

First Time Dressing

A few weeks ago my gay friend Paul phoned and asked if I would go out with him on Friday night. My husband John and I have known Paul for ages and we knew he was getting over breaking up with his long term boyfriend so I happily agreed. John stayed until Paul came round so we could all have a drink together and then he went off with a couple of his mates. After John left we had some more wine and then I went through to the bedroom to get changed. Paul followed me in and sat on the bed while I...

Crossdressing

Spanking School 6 Jennifer un dresses

Spanking School is the name my students use informally for my exclusive Erotic Education Enterprise.Our institution is inviting interns interested in inspection for fresh well-bred virgins of high social standing.Spanking School is presided by Professor Peter and head mistress Jennifer to dressage the tasty teens.Our Institution is a fame for its name and teen tuition to become submissive wives worth lots of money.Spanking students feel like a penguin in bondage boing to quote a song from Frank...

Episode 32 Getting Dressed

FantasyYou know the feeling: lying in a warm bed, breathing in a faint whiff of her perfume, new stiffy just starting, your wife / girlfriend / mistress / s1ster-in-law returns from the bathroom. Hair wrapped in a towel, skin all clean and smooth after a vigorous shower to wash your sperm out of her crevices."Come back to bed darling, you look gorgeous, all freshly fucked. Come on we've still got time for another quickie"."Get lost; you've had me all night. My arse is still sore. You're not...

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