CL Memories #1 - Crossdresser (True Story) free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
I used to get a lot of fun out of CL. I'll post some short stories about some of my experiences there. I sure do miss it. This happened about 10 years ago. I was divorced and living alone, and playing whenever I got the hots and had a good opportunity.

I checked CL one weekend night to see if there was any fun to be had, and found a post from a crossdresser visiting a nearby city and looking for company. She (I'll use that pronoun here) had a room in a local motel for the night. I responded to the ad with a nude of my body, and she wrote back a short while later telling me the motel and room number. The motel was one of the less expensive chains with outside entrances to the rooms, but a decent and safe place. It was later in the evening, after dark, so I put some condoms and lube in my jacket pocket and headed over.

I parked in the back, well out of sight of the street, and walked to the room. She answered my knock dressed in sexy lingerie, wearing a blonde wig. She was no spring chicken, probably in her early 40s, but I was in my 50s, so I had nothing to complain about. She was shorter than me, and very slender, with a nice fuckable ass. She was in black - bra, stockings, and garter belt, with no panties. Her small hairless cock hung flaccid between her thighs.

When I got inside the room there was another man there, naked from the waist down. I didn't mind sharing, so I sat down to watch them get back to what they were doing. He was younger and bigger than me, but visibly smaller where it counted. She sat on the edge of the bed, got him between her legs, and went to sucking his cock. After a few minutes he was fully hard, and she put a condom on him, then got up on all fours.

She moaned as his cock entered her. He slid in slowly, going balls deep in her ass. They were obviously enjoying themselves. I undressed to join in. I got completely naked, leaving my clothes on a chair in the corner. Stroking my cock, I moved to the head of the bed in her line of sight. I didn't want to interrupt them or spoil his fun, just show them that I was ready if they wanted me to join.

It was her party, and she was moaning her pleasure as he pounded her boy-pussy. She saw my erect, shaved cock, and eventually motioned me onto the bed. I lay down on my back and slid down until my cock was under her face. She was really into what she was feeling at her other end, and slid her mouth down over my bare cock. She put one hand at the base and stroked it with her hand and mouth together. I just lay back and put a pillow under my head, and enjoyed his thrusts pushing her mouth down on my dick. The other guy smiled - I guess he was enjoying the spit-roast as much as I was.

He fucked her ass for 10 minutes or so at a varying pace, then began to speed up his thrusts. She was holding my shaved balls as she sucked me. I could see the look of concentrated pleasure and impending orgasm on his face. He was holding her hips and pounding as deep as he could go. Finally he grunted and pulled her tight against him as he filled his condom with cum. I was in no hurry as long as my prick was in her mouth. I just watched as he pumped a few more times, then withdrew and went off to the bathroom. He came back within a minute or two, and started dressing, and she got off the bed to shepherd him to the door. I told him I didn't mind if he stayed, but he said he was done.

Then he was gone and it was just us two. I got up and got a condom out of my jacket, then asked her to get on top and ride me. I slipped the condom on and lay back. She got a bottle of lube and covered my rod with it, then knelt over me and slowly slid down onto me, taking me all the way in within a couple of strokes. We fucked that way for a few minutes, then I wanted on top. I rolled her onto her back without slipping out, put her legs over my elbows and began pounding down into her tight little hole. It wasn't too long until I was cumming. I let go of her legs, lay down on top of her and kissed her neck while I enjoyed the feeling of cumming in a tight hole.

After a few minutes that way I got up and went to dispose of the condom. I came back into the room and she was lying where I'd left her, on her back in the middle of the bed. I sat down to enjoy the afterglow and we chatted a little. She told me where she was from, and that she came to town every few months to get a room and live out her gurly fantasies. I moved over to the bed with her as we talked and began caressing her boy parts. She didn't start getting hard, so I assumed that reciprocation wasn't in her playbook for the night. I, however, did start getting hard, and asked if she was up for another round. She smiled and said yes.

I pulled another condom out, then went back to stand by the bed while she sucked me to a full stand. When I was ready I slipped the condom on and got her on all fours. I slid right into that wonderfully tight spot and started fucking. Soon I was driving her forward across the bed. We wound up with her flat on her belly, me on top of her fucking deep into her. Being older, I just couldn't get to that second cum. Eventually I just lay on top of her for a few minutes, enjoying her tightness. Then I got up, disposed of the condom, and started getting dressed.

When I was ready, she guided me to the door, and kissed my cheek. I told her to keep my email for the next time she was in town, but I never heard from her again. I sure would like to.

Same as CL Memories #1 - Crossdresser (True Story) Videos

2 years ago
  • 0
  • 24
  • 0

A Crossdresser Gets Caught

Johnny was gentle and had slightly feminine mannerisms for a guy. He had had quite a few escapades with women, a couple of failed marriages and a dozen or so relationships but all had fizzled out. He had never thought about the fact that maybe he was gay or bisexual and although he was not homophobic he thought the idea was not for him. He found women attractive and loved them wearing sexy lingerie and became almost obsessed with lingerie and all its variations, sometimes even more than the...

Crossdressing
3 years ago
  • 0
  • 24
  • 0

Jaq Invites Crossdresser Over

Anyone who follows our adventures will know what type of lifestyle we lead.A short while ago Jaq got chatting to a crossdresser online. It turned out that he only lived a short drive from where we live. Kieran was twenty-two, his pictures looked amazing. Jaq asked me if she could invite Kieran to visit, an offer that I could not refuse.All was set for the Friday evening. To say we were excited would be an understatement. Jaq and I showered and dressed. Jaq looked amazing as always in a very...

Crossdressing
2 years ago
  • 0
  • 133
  • 0

Milwaukee Cuckoldrsquos Wife and the Crossdresser

Judy used several sites over the years to find her friends with benefits. She never tells me until afterwards what she has done. It’s rare she tells me anything in advance. One day she advised me the k**s were at my parents and she was entertaining that night and I would have to stay in the family room. My curiosity was getting the better of me.She went and took a shower and asked me to come in and shave her pussy. She had me paint her fingernails and toenails. Once she was ready she put on her...

2 years ago
  • 0
  • 22
  • 0

Crossdresser for mature couple

I am a bi crossdresser....love some pussy or cock. I registered on an fabswingers looking for a meeting with similar people.I was actively looking for an older couple to have some fun with. To cut a long story short, I finally got talking to a guy called Bill. He and his wife could entertain a gurl like me for a fun filled evening, if I was game. We both had a list of dos and donts for the night and we went over a few ground rules etc.I was to be their maid and waitress for the evening. They...

2 years ago
  • 0
  • 37
  • 0

A Crossdressers Night in the Park

Last night I was on line in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with him. I told him that I was and then he asked me what I was wearing. I told him that I was all dressed up wearing a black silk mini skirtwith a black stretchy lace blouse. Master Brian then asked me what I had...

3 years ago
  • 0
  • 31
  • 0

Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.There is no cross dressing in the story but this is how I began my transformation fromregular boy into cock suckking teenage crossdresser.We were having a really hot heat wave. i meat with my older brother (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going...

4 years ago
  • 0
  • 56
  • 0

crossdressers 1st time

hi, im new to this. this happened about 3 years ago now.I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser.I thought enough...

3 years ago
  • 0
  • 21
  • 0

mature crossdresser 18 year old PART 1

Myself being a fulltime crossdresser and wear mini skirt and dresses all the time an high heels. A few weeks ago some new people move in across the street from me to be extact it was a woman and her 18 yr son.I talked to her few times and she was very nice and in our talks asked her if it bother her that i was a cd/tv she said nope. Well after couple weeks we became good friends and found out her son was shy and kind of a nerd. One day she came over to me and was little upset over something she...

4 years ago
  • 0
  • 19
  • 0

The Crossdresser Body Swap Part 1

The Crossdresser Body Swap Chapter 1 Ashleigh finished polishing her toenails with a final dab of red nail paint. She rolled onto her belly whilst letting her feet dangle off the bed to dry. She noticed the time on her phone and let out a sigh of annoyance, her neighbours would be coming around for another dinner night soon. Ashleigh always thought they were a weird bunch, always practicing meditation in their garden, plus their house was littered with all this voodoo and spiritual...

3 years ago
  • 0
  • 28
  • 0

Crossdresser Got Caught By The Neighbor

Hello readers, my name is Rajesh, a 24-year-old guy who likes to dress like a girl. I am in Australia now.  This story will tell you how a crossdresser got caught by a neighbor and had to do whatever the neighbor ordered. His name is Roy (name changed), he is 6’1 height with a well-built body, and he is in his late 50’s. I recently had to move to another unit as my old unit’s lease got finished. On a Friday morning, I was leaving for my office. I saw an old man (who lives in the next door unit)...

Gay Male
4 years ago
  • 0
  • 21
  • 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
  • 33
  • 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
  • 31
  • 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...

4 years ago
  • 0
  • 19
  • 0

Cd crossdresser sissy caught by mom and dad

Backstory - I just turned 19, in college and still live in my hometown with my parents. I've been crossdressing on and off for the last probably 10-12 years. Till I was about 15 it was just whatever my sister or mom had that I could get my hands on while they were gone. Then when I was 15, I would order some online, or sneak out and go to a store right before they'd close. I've only told two girls, one who didn't believe me and the other who was supportive but didn't really care. For the last...

4 years ago
  • 0
  • 13
  • 0

First time with a crossdresser pt1 True Story

Ive been married for a few years now, but I always find myself straying from time to time to get my fill of kink. Guess you'd say it is a way of easing stress every once in awhile. I got alittle break one time when the wifie was away visiting her parents for a few days. I was good at the start but after a couple of days had passed, you guessed it, the familier itch to go out and try something crazy hit. I have always been facinated by sub/dom and knew just were to take my search. Well it...

3 years ago
  • 0
  • 41
  • 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
2 years ago
  • 0
  • 21
  • 0

Crossdresser Turns Gay To Seduce His Tailor

Hi all! I am a family man with a loving wife, but she doesn’t know about my crossdressing. It just so happened that she had gone to her mother’s place during her pregnancy, and I got ample time for my crossdressing. I did all of my shopping on Myntra and bought myself some nice soft satin sarees, dresses, gowns, tops, high-heel shoes, a makeup kit, perfumes, and loads of bras. I was waiting for the delivery like a curious kid waits for their birthday gifts. Finally, the day arrived and the...

Gay Male
2 years ago
  • 0
  • 29
  • 0

My first Crossdresser Part One

When she walked in to the restaurant I knew I was in trouble. It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.Convincing she was not, a crossdresser without question. But pretty, really...

3 years ago
  • 0
  • 38
  • 0

A Crossdresser8217s Life

Hi! This is my first story on ISS so don’t be harsh on me. This isn’t a real story, but a fantasy which i am going to share with you,though the characters are real. I am a boy(21)(crossdresser) doing my engineering in Bangalore in a reputed college. I stay at one of my fathers friends house, his name is Rajesh. His first wife died due to cancer so he married again. His new wifes name is Rajni. Rajni, in her 30s, is a damn hot woman with a plus size figure. Now lets move on to story… Initially i...

Gay Male
2 years ago
  • 0
  • 22
  • 0

Danni The Crossdresser First Time Sissy

by - sissy debbie This is a true story about what happened to me after graduating high school and how I became a sissy for woman who was nearly twice as old as me. --------------------- The summer after my senior year of high school a neighbor asked me to look after her house and her cat for a week while she took a trip with some friends. Her name was Heidi and she was an attractive woman about 38 years old. She just wanted me to stop in and check on everything a few times. I...

1 year ago
  • 0
  • 27
  • 0

Nenu Crossdresser Nunchi Gay

Hi, na peru ajay. nenu tenth class ki vachinappatiki naku crossdressing alavatu ayyindi. enduko emo telidu, kani adavalla laga chira, jackettu vesukovatam istham. mukhamga Bra and Panty. ma inti venaka oka portion lo vunde oka ammayyi thana battalu vutiki bayata aresedi. ala aresina vatilo thana Bra lu kuda vundevi. mamuluga avi sayantram avi tisesedi. kani oko sari marichipoyo emo battalu tisedi kadu. ala tiyanappudo leka oko sari Valla bathroom lone vadilesina battallono (valla bathroom...

4 years ago
  • 0
  • 37
  • 0

crossdresser ashleythis my story

hi my name is ashley,I'm 48,and have been crossdrssing since I was 14.its about the time I discover masturbation.when ever I would take a bath or a shower I would take out of the hamper my sister panties and bra sit the and stroke my cock thru the material.often I'd find a pair of pantyhose,and would slip them on.felt so hot wearing them,I even wore them to school.lot times if no one was home I would sneek down to our shop that we had out back where you could not see it.inside I would strech...

2 years ago
  • 0
  • 23
  • 0

crossdresser violation

My house is a small two-bedroom cottage with a study, lounge and combined kitchen-dining room. My bedroom has an ensuite. It is located in a quiet cul-de-sac in a quiet neighbourhood where everyone keeps to themselves. It is perfect for me. Perfect because I am single (due to a messy divorce where she got everything except the debts), perfect because I work odd hours, and prefect because I like my privacy; oh, and also perfect because I am a closet transvestite. Like most...

3 years ago
  • 0
  • 242
  • 0

CD crossdresser daughterrsquos bitch

Note : This story is completely fictional!How did I end up like this? On my hands and knees dressed in just sexy stockings and suspenders and a lacy corset, my face in slutty make up, my lips wrapped around my daughter's boyfriend's cock while my daughter herself rammed an eight inch strapon up my arse. The worst of it was, humiliated though I felt, this was really turning me on. This is the story of how I became my daughter's bitch and how I came to love it.I suppose I shouldn't have let...

3 years ago
  • 0
  • 44
  • 0

Crossdresser in Love

I woke up with my hands bound, my mouth gagged, and my ass plugged. The bed I was on was comfortable enough. This was just a reminder that these parts of my body were no longer mine to do with as I pleased. For tonight would be my wedding night. For months we had planned things out. Picking out a dress, a place for the ceremony, all the things that brides do with their future husbands. But for me, it also included a regimen of hormones to complete my becoming as feminine as can be for my man. I...

Crossdressing
1 year ago
  • 0
  • 34
  • 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
  • 22
  • 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...

3 years ago
  • 0
  • 22
  • 0

Crossdresser wanting some dick on the road

I`ve been crossdressing since I was 20 years old.One of my favorite things to do is get all dressed up in womens clothes and drive around on the open road.Several years ago I was mad at my ex wife for doing some stupid shit with our checking account and we were split up for some well needed cooling off time.The more I got to thinking about her stupidity the more I got to smoking some pot and drinking a few mixed drinks to get the crap off my mind.I got pretty stoned and decided to get dolled...

2 years ago
  • 0
  • 32
  • 0

Telling Mom Im A Crossdresser Part 2 The Adult Store

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived. It was just past 9am when I heard a fumbling at the door, my mother had walked in with her heels in her hands and her clothes hanging loose...

Crossdressing
2 years ago
  • 0
  • 23
  • 0

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

Crossdressing
1 year ago
  • 0
  • 22
  • 0

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

4 years ago
  • 0
  • 27
  • 0

Crossdresser to Trans Escort Part 3

This is a continuation of my Crossdresser to Trans Escort series.After my first fuck for money with the restaurant owner, things escalated. I arrived at work the next morning wearing a pair of black trousers, black blouse and flat ballet shoes. The owner called me into the back office before we opened up for the customers. He was sitting behind his desk wearing a tight black t-shirt which showed off his tanned skin and bulging muscles. 'I really enjoyed our transaction last night' he grinned,...

3 years ago
  • 0
  • 42
  • 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...

3 years ago
  • 0
  • 23
  • 0

olderman and mature crossdresser part 1

It was just a normal friday day so I went to the store to buy some food for the week.I wore a jean mini skirt and pink t-shirt and tan pantyhose with my 3"heels and make up and all. As I made my way down thru the ailse I notice a older tall gray haired slim man following me.Well I gave him a couple bending over shots and eye contact.I made my way to the check out an seen him in other line.I finshed checking out when I got outside to load my bags in my car he was parked next to me.He spoke to me...

2 years ago
  • 0
  • 22
  • 0

Crossdresser ke saath maza

Hello frnds.How is everybody.I recently got another hot encounter in July 2008.It happend at my sis home.Both my sis and her husband work for an MNC.They had recently employed a new maid.They were supposed to go to Pune for some seminar from their company.Since this new maid is new in town and has nowhere to go so my sis said me to stay at her at home so that maid will not face any difficulty.i said ok.I understood the problem and said ok for the proposal.So i reached her home on the day on the...

Incest
3 years ago
  • 0
  • 30
  • 0

AutoRide Made Me A Crossdresser Whore 8211 Part 5

Except for some dirty and humiliating ones, most of Raghav’s dialogue will be in English in this part about the crossdresser whore. I thought that it is easier for me than translating each of the dialogues. The ride home was uneventful. I just sat dumbfounded in the back seat while Ragahv just fled the auto fast. In a short time, we reached my place. I picked my bags and climbed the stairs. Raghav followed me, carrying another small bag. Where did he get it from? I am sure he was spotting a...

Gay Male
4 years ago
  • 0
  • 19
  • 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
  • 31
  • 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
4 years ago
  • 0
  • 64
  • 0

Bi Beki TrueStory

This is the girl who is in this story with me : http://xhamster.com/photos/gallery/1352687/bi_sexual_beki.htmlThis all starts off with me going downtown just by myself to a well known gay bar. I have been bi-sexual since I was about 14 and I am 18 now. I was wearing a burgundy dress which flared out a lot at the bottom and was showing a fair bit of cleavage, my legs were bare and I had black lace panties on and a matching bra. I was in the mood for a girl tonight seen as I hadn't had sex with a...

2 years ago
  • 0
  • 39
  • 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
  • 19
  • 0

Blackmailed Crossdresser part II

A few weeks after that first incident with Stefan where he had blackmailed me into having sex with him, I got a text message off him. I was a bit surprised, as we had managed to ignore each other in work. I was growing optimistic that this incident was behind me. Even though it was left me feeling violated and with lots of confused feelings about myself.I was shocked to open the message on my phone and seen two pictures of him fucking me in the hotel! I was on all fours on he bed, in bustier,...

3 years ago
  • 0
  • 23
  • 0

Bisexual Crossdresser Fucked By Drunken Roommate

Hello, people. I am Sahil. I am currently living in Mumbai in a shared apartment with my roommate Raj. We both doing our engineering from different colleges in Mumbai. This story is based on my and my roommate’s real life experience. Which is how I am engaged in a sexual relationship with Raj. Let us start with the introduction. Introduction: Sahil The author of the story. I am 24 years old. Since I was at 14 I have a very strange fantasy of Crossdressing as a beautiful girl. Whenever I was...

3 years ago
  • 0
  • 19
  • 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
  • 37
  • 0

A Crossdresserrsquos Life

Initially i use to wear my sisters dresses or my mothers bra,panties,saree,blouse,petticoat and see myself in a mirror and admire myself. Though i wasnt so good at makeup, i used to apply lipstick and put some jewellery items. It couldnt make me look like a girl but the feel of women’s clothes turned me on. And then i used to masturbate after my every crossdressing session, thinking about being fucked by a guy. But then as i grew up chances of being alone became less and i had to kill my desire...

2 years ago
  • 0
  • 56
  • 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
  • 28
  • 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
4 years ago
  • 0
  • 17
  • 0

Picking up a Crossdresser in a Bar

This happened about 20 years ago. The basic events are completely true, but in those days I drank a lot, so I don't remember many of the details. For the purposes of a good story, I made up a few things to fill in the blanks in my memory.It was a weekend, and my wife had taken the k**s to visit her father 400 miles away. I was alone at the house, and I knew an opportunity when I saw it. At the time we lived in a small city, and there was a gay bar in town that advertised a weekly drag show on...

2 years ago
  • 0
  • 19
  • 0

Crossdresser Stories 8211 Assfucking in panties

I have been ‘mildly’ crossdressing for over a year now. I say ‘mildly’ because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it’s like having your whole lower half caressed persistently. I have thought of wearing a bra but, although I can almost imagine how amazing it would feel, I don’t think men look...

2 years ago
  • 0
  • 17
  • 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...

3 years ago
  • 0
  • 21
  • 0

crossdresser confession part 1

I really loved my wife; she was the most beautiful creature I have ever known. Tall, brunette and the longest legs you have ever seen. Myrtle's beautiful face is framed by her gorgeous brown hair. She was about 5'8" and had a great ass. Her curves were soft and very feminine, not a big chest but nice and perky tits I loved to play with.She would drive me crazy when she donned a pair of pantyhose and heels with a short skirt. She didn't know it, but she would not have been able to keep my hands...

Crossdressing
2 years ago
  • 0
  • 27
  • 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
2 years ago
  • 0
  • 18
  • 0

The Next Night Crossdresser Part 2 of 2

I woke up early from the sunlight shining through the windows. We’d forgotten to close the curtains when we collapsed into bed last night. Jenny was already awake and watching me. ‘I was just about to wake you up with a blow job,’ she smiled.‘Funny, I was thinking of doing the same to you!’ I laughed.Jenny kissed me then turned around in the bed to lay on her side so our cocks were facing each other. We both had erections already. I shuffled close and took her long cock in my mouth, closing my...

Crossdressing
4 years ago
  • 0
  • 22
  • 0

Simran A Crossdresser Part 3

After that rather eventful evening with Ram, I opened up to my fears and inhibitions. Now performing on cam or coming out dressed in front of an online crowd was something I could do easily. I still covered my face, since I wasn't yet ready to reveal my identity. As far as I remember, it was a couple of weeks after my interaction with Ram that I heard a commotion outside the house. I went downstairs and looked through the window, and what I saw was astonishing. People were running, screaming...

Crossdressing
1 year ago
  • 0
  • 13
  • 0

First Time With A Crossdresser Part 1 of 2

I’m Scott, 36 years old and recently divorced from my wife of 12 years. It was an amicable split with no kids to complicate matters. We sold up, divided everything two ways and went on our merry way. Our sex life was good and regular but a little boring. We stuck to the same three positions – missionary, her on top and spooning. I’d give her oral but she wasn’t that keen on going down on me and her facial expression when she was blowing me put me off asking for it! I’ve never needed more than...

Crossdressing
3 years ago
  • 0
  • 28
  • 0

Memoirs of a Crossdresser Chapter 1

My True Story Chapter 1: I was a kid when I first discovered women's underwear. I loved the way it made me feel. I had a friend who I'd play the normal games that kids play with, and I would always be the girl character. We were children, so nothing out of line went on, but even at a very young age, I had felt an attraction to femininity. There was something that made me feel like I should be the damsel in distress, waiting to be rescued. I remember wanting to feel girly. As I got older, my...

Crossdressing
4 years ago
  • 0
  • 20
  • 0

Crossdresser Business Trip to South India

Sheila Boy Mon, Jun 3, 11:09 AM to meHi All.Guess you all know i am a bisexual guy and i love to crossdress whenever i get a chance and i am alone.Well as it happened I was on a work trip to chennai and bangalore some time back. It was not a planned one and my boss told me in the night that i had to go and all arrangements have been made. I reached by the afternoon flight, took a cab and checked into the hotel booked by the office. After completing all this and...

2 years ago
  • 0
  • 19
  • 0

Simran A crossdresser part 2

Well after my little adventure in the bathroom with my mom's panties, I went out for a couple of drinks with my friends. But, in spite of having company, the only thing that kept playing in my mind was the feel of those satin panties and how horny I had felt in them. All I could imagine was getting back to the house as soon as possible, before my parents returned, and having one more go at it. I returned around seven in the evening. Since my parents had a convenience store, I knew they wouldn't...

Crossdressing
2 years ago
  • 0
  • 18
  • 0

Simran A Crossdresser Part 1

Well I still remember the day back in the summer of 2010. I had just turned sixteen and was introduced to the world of cross dressing in the most fantastic way possible.I guess introductions are in order. I am Simar, an average guy from India, who goes to college, has a great family, great friends. Well something you gotta know first. My family follows sikhism so I have a beard, a mustache and body hair which I cannot remove because of religious reasons. But it is a blessing in disguise because...

Crossdressing

Porn Trends