Made My Friend A Crossdresser free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
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 me in gym.

Few months later he moved to my apartment and we became good friends. We became such good friends that we never hesitated in talking about anything. I remember I used to ask him why he took so long in bathroom and he would say that I was masturbating and this time my load was so much that I could impregnate 10000 women. Lol.

One day I don’t know how but I decided to buy a lungi and try it on. I feel comfortable with bare minimum and roam around in my flat in just underwear but that day I bought a lungi and checked in youtube how to wear that. I put that on and took out my underwear and amazingly it felt good and different with your jewels enjoying and happily bouncing. I told Anshul about it and asked him to try too.

He borrowed my lungi and went inside and tried that on. I touched his butts and realized he’s wearing underwear beneath that so I told him to remove that and I put my hands inside his lungi and tried to pull them down. Earlier he used to wear some stupid Jockey euro underwear but after seeing me he bought some good expensive ones. So back to story, I pulled his underwear from his back while lungi was still on and that was the first time I touched his bare butts. You wont believe it but I got a hard on immediately and his butts were so smooth and not a single scar or hair. Just like I was touching a piece of marble.

I tried to hide my hard on and asked him to tell he how he felt. He turned around and walked a few steps and then he blushed and said “this is awesome and crazy”. He was too trying to hide his hard on but then I asked him to come near me as I want to tie the knot properly. Without knowing my intentions he came near me and I untie the knot and started making adjustment and suddenly his dick popped out. I boldly took his penis and hid it under the lungi again. I wanted to see his butts more than his dick.

So I asked him to turn around and acted as I am adjusting his lungi. The moment he turned around I dropped his lungi and saw his hairless smooth butts. The second I dropped it he bent down to pick it up and I got a glimpse of his virgin ass surrounded by cute little pubes. I enjoyed how the fair and flawless butts changed colors when they were meeting there. It turned light brown to little dark brown.

I got up immediately and stepped back and tried to tie the knot. I came near him innocently and took his penis in my hand and said “ So Anshul, looks like someone is enjoying lungi”. He blushed and said yeah this is really good. I slowly started stroking his penis and he was getting harder and harder.

Then I asked him if he wants to jerk off. He said yes and without a moment’s notice I removed my underwear and was butt naked in front of him and he was still holding his lungi and penis together and giving a very exotic butt exhibition. We went to bathroom and on one hand I took his penis and on another I started caressing his butts. He dropped his lungi and held my penis and started stroking. We jerked off for the first time together.

The story doesn’t end here. Later that day we went out and bought him a lungi too. He was so excited to wear that that as we reached home he went to his room and changed to lungi. We jerked off again that day. We sleep together so the best part about lungi is that you can slide you hand in and enjoy whatever you want.

I too continued wearing just lungi but in the morning when I get up I realize that I was sleeping naked. I had other roommates too and maid used to come early in the morning to clean the house so I stopped wearing lungi at night. But I have never seen him wearing anything other than lungi since then. He tried too many different styles that made me crazy and he knows that how much I love his butts. I would ask him if I found any scar on his butts or put an ointment if there’s any acne or boil.

We were together for another 3 years and now we’ve met again after 2 years and we’re living together. One day I saw he got a women night gown in his bag and I asked him why he got this then he replied that this is better than lungi, no knots and hangs all thru the body. I told him to try Arabic gown not this women gown but he told that he liked this more than that and he tried all those too. Not sure if he’s turning into a cross dresser or not but I am surely enjoying his new avatar.

Right now he’s lying on bed wearing that night gown with his legs and butts clearly outlined form outside and this is what motivated me to write this story.

Same as Made My Friend A Crossdresser Videos

4 years ago
  • 0
  • 25
  • 0

Amazing Night With A Sexy Crossdresser

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...

2 years ago
  • 0
  • 36
  • 0

my life as a sissy crossdresser

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...

4 years ago
  • 0
  • 33
  • 0

Room 209 First Sex as a Crossdresser

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...

3 years ago
  • 0
  • 43
  • 0

Night Trawling The Crossdresser

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...

Crossdressing
1 year ago
  • 0
  • 38
  • 0

Hitchhiking teen crossdresser

It 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...

1 year ago
  • 0
  • 25
  • 0

My first time with another crossdresser

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...

4 years ago
  • 0
  • 21
  • 0

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...

2 years ago
  • 0
  • 23
  • 0

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
4 years ago
  • 0
  • 49
  • 0

My Date with a Crossdresser

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...

4 years ago
  • 0
  • 24
  • 0

First Time With Crossdressers

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...

2 years ago
  • 0
  • 34
  • 0

Chronicles With Sexy Crossdressers

My 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 Male
2 years ago
  • 0
  • 43
  • 0

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...

3 years ago
  • 0
  • 22
  • 0

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
2 years ago
  • 0
  • 60
  • 0

firsts time Im 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...

3 years ago
  • 0
  • 39
  • 0

Telling Mom Im 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
2 years ago
  • 0
  • 63
  • 0

Fucked Girlfriend8217s Bestfriend In Oyo Room

Hi friends! My name is Divine and I’m here with another story and I hope you will like this one. This happened last week. I’m in last year of my graduation and fortunately, I have a girlfriend since second year. So, coming to the story. The name of the girl in this story is Vaishnavi. She is my girlfriend’s bestfriend and they are like sisters. One day, my girlfriend and I were casually talking and I asked my her to have sex with me. But she said I won’t do it till marriage. I tried to convince...

2 years ago
  • 0
  • 20
  • 0

Telling Mom Im 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...

2 years ago
  • 0
  • 29
  • 0

The start of my life as a submissive crossdresser

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...

Crossdressing
4 years ago
  • 0
  • 30
  • 0

Craigslist crossdresser

It 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...

2 years ago
  • 0
  • 34
  • 0

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
3 years ago
  • 0
  • 31
  • 0

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
3 years ago
  • 0
  • 17
  • 0

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
4 years ago
  • 0
  • 18
  • 0

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
4 years ago
  • 0
  • 70
  • 0

Bestfriend to sexfriend

My name is Amy. My bestfriend, who also happens to be my new recent ‘fuck buddy’, is Joey. We have known each other since the 7 th grade. All through high school we were quite flirtatious with each other, but never once acted upon it. Until now. I’m 18, and he just recently turned 19. On his birthday he asked me to go to the beach with him. So I made sure I had a nice clean shaven pussy, and then I put on the sexiest bikini I own. It’s skanky, and hot pink, and it’s thin enough that when my...

4 years ago
  • 0
  • 64
  • 0

Bestfriend to sexfriend

My name is Amy. My bestfriend, who also happens to be my new recent ‘fuck buddy’, is Joey. We have known each other since the 7 th grade. All through high school we were quite flirtatious with each other, but never once acted upon it. Until now.I’m 18, and he just recently turned 19. On his birthday he asked me to go to the beach with him. So I made sure I had a nice clean shaven pussy, and then I put on the sexiest bikini I own. It’s skanky, and hot pink, and it's thin enough that when my...

Straight Sex
3 years ago
  • 0
  • 21
  • 0

Cock sucking Crossdresser

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...

2 years ago
  • 0
  • 21
  • 0

The feminine crossdresser

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...

3 years ago
  • 0
  • 15
  • 0

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 with each other...

2 years ago
  • 0
  • 21
  • 0

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...

4 years ago
  • 0
  • 43
  • 0

My Night with a Crossdresser

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...

4 years ago
  • 0
  • 40
  • 0

Halloween cd crossdresser

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...

3 years ago
  • 0
  • 26
  • 0

Uber driver fuckes teen Crossdresser

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...

3 years ago
  • 0
  • 24
  • 0

My first time as a Crossdresser

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...

2 years ago
  • 0
  • 30
  • 0

First taste of cum for a Crossdresser

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...

2 years ago
  • 0
  • 36
  • 0

My First Crossdresser

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...

2 years ago
  • 0
  • 23
  • 0

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 &...

4 years ago
  • 0
  • 25
  • 0

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...

3 years ago
  • 0
  • 32
  • 0

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...

2 years ago
  • 0
  • 29
  • 0

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...

2 years ago
  • 0
  • 28
  • 0

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,...

3 years ago
  • 0
  • 15
  • 0

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...

2 years ago
  • 0
  • 16
  • 0

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...

2 years ago
  • 0
  • 20
  • 0

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
2 years ago
  • 0
  • 36
  • 0

The 2nd Halloween for a Boy Dressed as a GirlPart 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...

3 years ago
  • 0
  • 43
  • 0

SALLYS 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...

1 year ago
  • 0
  • 17
  • 0

The hottest crossdresser

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,...

Bisexual
4 years ago
  • 0
  • 27
  • 0

Madeleine has been working late with her new boss

Madeleine was working late with her new boss Deirdre. They’d been working late for two weeks trying to tidy the mess left by the previous manager. At last they’d cleared the backlog. Deirdre sighed, looked directly at Madeleine, and stretched up her arms – her large soft breasts pushed forward in her skintight jumper making it ride up to reveal a stretch of suntanned stomach. ‘I think this calls for a celebration.’ Madeleine was disturbed by the sinking feeling in...

4 years ago
  • 0
  • 33
  • 0

Madeleine Improves the Odds

After a long stressful day at work, Andy and Warren were winding down at Distiller's Microbrew & Tap. Each were on their second beer when Warren said, "Andy, did you read the news this morning?""Didn't have time. What, another story about the President's Tweets?""No, Andy, something worse.""Immigrants being deported?""Worse.""Well then, Warren, what in the hell is upsetting you so much?"The two men were talking sports, politics and women. Warren took a swig from his glass and said, "You're not...

Cheating
4 years ago
  • 0
  • 23
  • 0

Madeleine Ch 07

March, 1920 Le Havre, France It was with a deep sense of melancholy that I stood along the rail at the stern of the ocean liner, watching the coast of France recede into the distance. I was going home, after seven years of service with the American Embassy in Paris, and while part of me was glad to be returning to America, a larger part of me knew I was leaving behind a large part of my life. It was a cold, blustery day on the cusp of spring, and I had my overcoat buttoned to the top to...

4 years ago
  • 0
  • 21
  • 0

Madeleine Ch 04

December, 1915 Paris, France Madeleine looked resplendent in her dark green dress, with the bright red corsage I had pinned on her breast. She looked very much in keeping with the holiday, which was the idea, since we were entering the ballroom at the Ritz Hotel, the same one where we had spent our wedding night, for the American Embassy’s annual Christmas banquet. Because the United States was still neutral in the Great War that was raging not far away, we were not under the same moral...

2 years ago
  • 0
  • 31
  • 0

Madeleine Ch 03

June, 1915 Paris, France ‘A toast! A toast to Robert,’ cried Sergei Hoffmann, over the din of well-wishers. ‘Hear, hear!’ was the response from several corners of the room. We were gathered in the private room of a well-known Paris restaurant for the traditional bachelor’s night, and the good food and copious amounts of spirits in all varieties had made for a memorable evening. Stories – many of them bawdy – had been told and conversation had been brisk. These were my friends, the people I...

4 years ago
  • 0
  • 27
  • 0

Madeleine Ch 08

CHAPTER 8 Paris, France March, 1918 I had been on furlough from my duties as an attache from the U.S. Embassy to Gen. Pershing’s headquarters, and Madeleine and I had finally reconnected after months of forced celibacy after her miscarriage and subsequent emergency hysterectomy. I had finally come to realize how close she had come to dying that day. Only a quick transfusion of blood helped her survive the surgery that saved her life, but deprived her of the ability to have any more...

2 years ago
  • 0
  • 25
  • 0

Madeleine Ch 06

June, 1917 Paris, France It was on a warm late spring morning that I arrived in my office to be greeted with a summons to the ambassador’s office. When I arrived, I stopped short, for Mr. Stark had a visitor, someone I knew well, and for whom I had decidedly mixed feelings. Gen. John James Pershing was seated in a chair across from the ambassador’s desk, and he rose when I entered the office. ‘Sergeant Guidry,’ he said as he offered his hand in greeting, using the rank to which I had risen...

2 years ago
  • 0
  • 28
  • 0

Madeline in Oregon

Madeline in Oregon She hadn't seen her Aunt Margo in many years but she wasn't feeling guilty. Her family had made it clear. They did not agree with two women living together. The telephone call had to be dealt with immediately though. Margo was her mother's sister and had received the lion's share of the estate at the probate three years earlier. The call wasn't from her Aunt, rather from Margo's younger 'partner' Allen. Aunt Margo had been married but after nineteen years they had...

3 years ago
  • 0
  • 40
  • 0

Girlfriends Bestfriend

True story about my girlfriends bestfriendSince her mouth was at just the right height anyway, she immediately bent over and pulled my dripping cock right into her mouth. Her mouth was working wonders on my cock so I decided to test her sucking ability as a true slave. I reached out with my hands and pulled her entire head down onto my cock as I stuffed my foot up her cunt. Her gasp for breath was overwhelmed by her grunt from my foot fucking her cunt. Her cunt was taking my foot deeper and...

2 years ago
  • 0
  • 25
  • 0

Madeleine Ch 02

Paris, France February, 1915 It was cold, bitterly cold, as I turned up the collar of my overcoat and walked out of the embassy into the gathering gloom of the late afternoon. On impulse, I decided to turn down the little side street that was so familiar and visit Marcel’s again. I hadn’t been there since my return to France a few weeks earlier, and I found I missed it. So much had changed in Paris since those heady days of August, when the young Frenchmen had so eagerly sought out war. No...

3 years ago
  • 0
  • 20
  • 0

Madeleine Ch 05

September, 1916 Paris, France It was a Monday, when my life took a significant turn. I had completed my morning exercise at the embassy and had arrived in my office when I was summoned to Mr. Stark’s office for what was described as an urgent meeting. This in itself was not unusual, as I spent almost half my time in the ambassador’s company, discussing events, planning strategies or interpreting for him. But this time, I found him in the company of a high-ranking British general and the...

4 years ago
  • 0
  • 21
  • 0

Madeleine Ch 01

Author’s note: It has been nearly a year and a half since my last submission, and over these past few months of idleness, I’ve been searching for some idea, some story line that would challenge me, and get me excited about writing again. I have about a dozen stories that I’ve started, but never got fired up over, so they sit in a file somewhere and will likely never see the light of day. I kept coming back to this scenario, however, and each time I did, the more it intrigued me. With the...

Porn Trends