Confession and testament of a crossdresser
- 4 years ago
- 21
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Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...
it should be noted that i did not ask for this disposition to crossdress, rather it was presented to me quite by accident. circa 1958...grade school PTA fashion show. PTA fathers were asked to put on a fashion show dressed as their better halves. my dad was right in the mix. I remember he wore some mid calf, grey business suit w/jacket, tan stockings and black heels. i remember this because he practiced dressing days before the show. he wore some makeup and a wig. not very passable, but not...
crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – braI've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight...
In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my brother and sister. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer...
The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods. During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of life. Each person is absorbed by their own petty concerns, each oblivious to what is happening on the...
CrossdressingIt was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...
A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or...
For once, I actually decided to look at some of the other categories on the streaming sites I'd visit. So many things came up under fetish. Some of it I don't get but to each their own. A BBW was mixed in with the fetish and as I had expected before hand, it wasn't my cup of tea. Several videos had girls dominating guys in leather or latex outfits. I liked how tight they were, showing off every curve of their body, leaving little to the imagination. Upon thought, I had never been...
Hi ISS friends, this is banisa from Chilakaluripet. Na age 38 years, working in a private office in Chilakaluripet naku English baga radu andukani Telugulo cheptunna. Naku chinnappatinunchi ante younger years nunche modda jadinchukovatam baga alavatu ayindi. Theatre lo kurchuni cinema heroines ni chustu modda jadinchukune vadini. Na modda 5 inches untundi. Chilakaluri peta lo lanjalu chala ekkuva mandi untaru. Okasari oka malahyalam sex cinema chustunna. Adi black and white movie. Andulo...
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 MaleMy email id is Do not forget to let me know how this sex story was. Who knows, we might get even lucky if everything goes well ;) Clean shaved men inside female clothes (or people who are known by the name crossdressers) are my new found favorites. Believe me, I always make it a point to taste every bit of them with passion and fire. My hands and tongue never leave an inch of their body. Hairless, like women and the ‘EXTRA’ jackpot called ‘COCK’, is simply divine. This is a story of how a...
Gay MaleThis 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...
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...
CrossdressingNote: This is not your usual Lush story. It is an experimental play in a theater of the absurd style. There is no sex but it is an entertaining comment on marriage. I encourage you to indulge in something different. I think it will make you laugh and maybe cry.Scene: A formal living room. Mortimer is seated on a sofa in the center of the room when Myrtle enters and sits on the sofa next to him. She is wearing a blue floral dress and a pearl necklace, her gray hair is tied in a bun. Mortimer is...
Love StoriesWhen 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...
I am a bisexual cross-dresser/sissy and have been enjoying my life as such for many years. It all began for me when a friend asked me to look at some of his 'girlie' magazines.We went up to his bedroom and looking through the magazine got Chris really excited and he got his cock out and started to masturbate. I couldn't take my eyes off his cock and I slowly reached out and touched it and when he removed his hand I curled my fingers around his erect shaft and began to slowly wank him.I just...
CrossdressingIt finally happened. I got a response! I’d been corresponding with him on Craigslist, but then suddenly Craigslist personals were banned. I tried to reply to the Craigslist generated email that I thought was his, but I’d deleted all of his email’s in a moment of weakness. Now I had no way to get in touch with him. He’d posted about hosting crossdressers and providing a safe, relaxed place for us to fulfill our fantasies. He said he would be gentle. I’d told him who I was, that I liked to wear...
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...
CrossdressingHey, 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 Malehiiiiiiiiii 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...
CrossdressingI 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...
CrossdressingWhen Father Mortimer checked into the hotel it was eight in the evening.The room was a basic no frills double with a small bathroom. He would never stay in such a hotel if he was attending one of his ecclesiastical conferences but for what he had planned it was just perfect.He got down on his knees and bent his balding aged head over a black gilt leaf Bible he had respectfully placed on the edge of the bed.“Blessed Lord Jesus forgive me for my sins,” he muttered and crossed himself three...
SpankingDedicated to a lovely young lady that would have graduated in 1960 with a first initial of "J" First and most important, this is a totally true story. Because it is true, there is little sex and what there is, has not been embellished to the best of my knowledge. One almost always remembers their "Firsts." Their first kiss, first date, first love, first sex and first crush. This is a story of all the above and more. I have always been a shy person. All through my freshman and sophomore...
Its 18 months ago. I had now become comfortable wearing womens clothes. I had been experimenting for around 3 months. I gradually started to get more confident in both my clothes ......and without. I started to dress more like a slut. Short skits. Suspenders. Corsets. I had also become more comfortable with my body as well. My hole was tight as could be. Like everyone, i started with fingers, one, two .....before moving on to small toys. After a few months, i had graduated to a 9 inch...
I had never really been with another man before and I had always thought about it as I dressed up as a slutty girl and played with my little toys to orgasm. I'm a little tall at 5, 9 and with heels a monster! I have an average body, nothing feminine, but not out of shape and a nice big bubble ass.Until that night. I had been sent to Dallas for a business trip and was super excited to dress up in my hotel room and play around! I played around a couple days in my room and just got dressed did...
Hi friends, I hope all readers are fine and happy, am a regular reader of iss, my name is sebi of 32 age, belongs from Kerala, working in a Pvt it company. This story happened when I was 26 yrs.This is my first story here. Any way lets come to story , this story in between me and my neighbor seena she is very rich and 41 years old at that time me at 26 only. She is white in color and married having one child, her huss is working in Dubai in it company. Am not married at that time. Appa, amma...
When I was out on my own I started to buy a few things' mostly panties and thigh high stockings then a skirt and a blouse things that where ease to get to fit me. From there I learned to find my size in dresses and shoes this started to put my wardrobe to gather, but I still needed a wig and makeup so it was back online for more shopping, With lots of practice I became pretty good at putting on my makeup, plus doing my wig hair and a waste cincher I looked pretty darn good if I say so my...
Chucky open’s his eyes as he awakes, looking around at his familiar surroundings in his bedroom. Band posters, comic books and video games all over the floor. His parents always gave him crap about the things he liked and tell him the typical “you’re too old to be into thoses kinda things!” He didn’t care though. He stepped out of his bed in his black t-shirt and grey track pant’s that he wear’s to bed and walks over to the window to look out as he...
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...
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 with each other...
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...
I am not a good writer but this was the hottest night of my life.I was out of town on a Business trip, staying alone at a nice hotel. After a long day of meetings, I was sitting at the Hotel bar drinking a glass of Scotch.The bar wasn’t crowded but wasn’t empty either. The seat next to me was open. Wasn’t long before what I initially thought was a woman came in and sat next to me. She said hello and ordered a glass of white wine. I realized then that she was a Cross Dresser. she looked to be...
TinkerbelleMy sister , Candy, and I were fraternal twins, but looked nearlyidentical. Pretty much the same height weight and build. In high school,she was always teased about having small tits and I was always teasedbecause I was small, thin and had a big ass for a guy. Because of this wewere extremely close. Best friends really. We spent nearly all our timetogether.After college she became a consultant and I became a math teacher. Becausewe were so close, I spent lots of time at her house...
Hi guys im a cd from Orange County and i had the sex ever last night with someone I never expected. So it was around 1 and i had just soent the night with my “friend” well I had just blew him and watched a movie and he got me an uber so i kissed him and left when tge uber came and I went on my night. He told me it was a white truck and espanic i went in and told me my “friends” name and we drove off. It wasnt even 10 seconds and he said what was my name i told him i was “. “ and he said nice to...
Only a few years back in my young 20's i discovered Craigslist. I had no idea something like that existed and was immediately drawn to it. After building up the courage to meet up with a few guys a couple times i found an add in the T4M section. I got instantly hard when i seen this girls pictures. A slim sexy girl with an ass to die for and a desire for Cock. After some back and forth emailing for a few days we agreed to meet in her place.I went around to her place late that night when the...
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 joining...
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 &...
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...
“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...
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...
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,...
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 MaleNote: ——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...
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...
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...
Lesbian5th 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...
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...
I was drinking with my friend Curtis one night as his girlfriend Jane was out with her friends having some drinks. The topic turned to cross dressers, as I had had let it slip, that one time I mentioned to him, I had dressed as a girl a few times when I younger in my moms clothes, and it felt great. He asked if I had any girl’s clothes at home that I wear from time to time, which I reluctantly said yes. With that Curtis asked if I would wear some of Jane’s clothes to see how I looked. “Sure,...
BisexualTHE AMAZING MR. MORTIMER My girlfriend Rachel and I had decided to take a two week vacation to PuertoRico. I had first come across the girl on the streets of San Juan. She cameup to me and begged me for some money. At first I was going to say no. ThenI noticed how beautiful this young girl was and I was intrigued. I startedto reach into my purse to get her something, and she smiled at me. She hada very beautiful smile. It was in fact an entrancing smile. I kept her close to me with small bribes...
Note: This is not your usual Lush story. It is an experimental play in a theater of the absurd style. There is no sex but it is an entertaining comment on marriage. I encourage you to indulge in something different. I think it will make you laugh and maybe cry. Scene: A formal living room. Mortimer is seated on a sofa in the center of the room when Myrtle enters and sits on the sofa next to him. She is wearing a blue floral dress and a pearl necklace, her gray hair is tied in a bun. Mortimer is...
When I was 27 years old and single, I really liked going to shows at night, to nightclubs, especially when it came to beautiful women. One day I went to a transvestite show and was fascinated.These men dressed as women groomed themselves more than any of the women he knew; her wardrobe, her makeup, even her movements, were more feminine than any woman's.I started visiting an exclusive nightclub, where every night there were transvestite performances imitating well-known artists and singers.I...
Hi indian sex friends. This is rahul54545 with my continuation of my first story my sexy aunty seena. As I had narrated in my first story I seduced my horny aunty seena who is a sex bomb of 32 years old. I was 18 at the time and she called me to help with something in the kitchen. And I just played her by covering her eyes and my cock rubbed her ass and as she was a horny bitch who didn’t get regular fuck, we ended up having sex in the kitchen floor until her children called for her. As I had...
IncestAs was his habit at lunchtime, Hal left the building and walked through the office park for exercise. It was a partly cloudy day, and for the moment it seemed overcast. On his way to a small path through the woods, he saw her. Sandy was an attractive redhead with a sensual voice who almost always wore a tailored blouse, a roomy ankle-length skirt, and one-inch pumps. Her wardrobe varied in color, patterns, and material, depending upon the season, but always the same ensemble. Hal watched as...
Hi friends .. Mera naam viraat hai mai uttrakhand ka rehne waala hu. Meri umra 24 saal hai dikhne me ek achaa khaasa naujawaan hu. Dosto ye meri pehli aap beeti kahaani jo mai kissi site pe daal rahaa hu. Maine bhut si kahaania iss site pe padi aur mujhe lgaa ki mujhko bhi apnaa kissa yahaa share krnaa chaahiye . To dosto meri kahaani pade aur mujhko mail kr k bataaye ki story kaisi lagi aapko .Jiss aunty yaa bhaabi ko mujhse secret sex chaahiye wo bhi mail kare il.Com To dosto pesh hai meri...
Elizabeth Fleming told me some of this story in the years before she died, aged eighty, in 2010. The more graphic scenes are mine but the emotions and surrounding history are hers. She was my Great Aunt, great in so many ways for she was the third family member I ever revealed my sexuality to, the first two being my parents. I had known since girlhood that she shared a cottage in Hampshire with her friend, Portia, but had never known their relationship was more than sisterly. When I told her...
Lesbian"I need to find someone to take me camping," she said while standing in my cubicle. We'd just been talking about how much we enjoyed camping and the outdoors and I'd been showing her some of my nature photos. I can't even remember what brought it all up, but it was fun to open up with a coworker like that. I like to feel the intimacy that comes from opening up to others and having them accept me. It's even better when we have similar interests and I can feel that rapport growing almost...
She wanted to remember. The hookah was a beautiful piece. It stood at 4 ½ feet. Dark red… it always was her favorite color. This hookah was her personal prize. It only had one hose, one smoker. She pulled the airtight box from its hiding place and opened the lid. Once released, the heady aroma drifted, tickling her nose. The new batch of bud was a dark green, but the crystals were so thick it turned everything pastel. Breaking it apart just enough to smoke easy, she arranged the weed in...
Introduction: While a few details have been tweaked, this story is as close as I can remember it Prologue She wanted to remember. The hookah was a beautiful piece. It stood at 4 ½, feet. Dark red&hellip, it always was her favorite color. This hookah was her personal prize. It only had one hose, one smoker. She pulled the airtight box from its hiding place and opened the lid. Once released, the heady aroma drifted, tickling her nose. The new batch of bud was a dark green, but the...