The Hottest Crossdresser - Part 2 free porn video

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

The next day seemed like it would never come. The phone rang, it was Curtis, he said it was on and gave me the address to the hotel we would meet at, and that John was all in. Curtis said that he told John how hot I looked the night before, and he was excited to get together. I packed a small suitcase of lingerie, heels, make-up, wigs and skirts, blouses and headed over to the hotel about mid-afternoon.

I called Curtis and told him to not show up with John until about 7pm as I was going to take time to fully get ready. As I got into the room I took a hot bath and shaved my whole body, then I painted my toenails a powder pink, and had some long press-on nails that I painted the same and would put on last.

What was I going to wear? I decided after about 30 minutes that I was going to start by putting on a lace pair of “v” shaped pink panties, then I squeezed into a pink teddy with six garter straps, carefully I pulled on these black stockings that are sheer, yet stretchy that have these pink seams in the back with the keyholes, I pulled them to very top of my legs and adjusted the straps to keep them as high on my legs as possible!

I put on my Cover Girl base make-up, then black eye-liner, blue eye-shadow, with white eye shadow on the eye-lids; and thick slutty mascara. Finally I put on some hot pink lip stick with lip gloss over it. Now it was time to put on this nasty tight, see-through pink blouse, and wiggled myself into a black mini-skirt, I put on the 5 1/2” pink closed toe heels, put on a short sassy curly black wig, and attached the pink finger nails.

I was done! I looked so fucking nasty. I was shaking with nervousness, that I poured a stiff drink to calm my self down, and started to smoke a cigarette. Midway through the smoke, I got a knock on the door. My heart was racing so bad, I thought I was going to pass out.

I felt like I was floating towards the door, when I opened it. “Hey, boys…how are we doing….?” Curtis and John walked in and just couldn’t keep their eyes off of me. “Stop, you guys already have me a nervous wreak – hopefully you cocks will calm me down.” I strutted over to the center of the room and turned away from them, I bent over, put my hands on my knees and gyrated my ass from side to side, I knew my skirt was short enough and exposed my stocking tops, they also got shot of my pink panties. I turned back around to see the look on their faces, and they looked mesmerized!

I moved over to the small dining table, sat on it, took a big sip of my drink and dangled my stocking legs back and forth. “Which one of you has the biggest cock?” With that, both men started to pull down their basketball shorts, take off their shirts and shoes, till they were naked. Curtis black cock was about 13” long and hung to the right, John’s cock was really thick, was about 11” and hung straight down.


“How do I look guys…am I nasty enough for you?” I asked in my hottest voice. They were now fully erect. Without a word they both carried me to the bed. I got on top of Curtis and John positioned himself behind me, I pulled my panties to the side as knew what was next.

Me and Curtis started to kiss and John was kissing my neck, after some maneuvering they were both inside of me. It was so exhilarating! I stated this chant: “When the cow goes moe, sih-ha, sih-ha, it’s time to screw sih-ha, sih ha, don’t be afraid cause you’re father does it too, sih-ha, sih ha.” I was doing it in rhythm to the serious pole fucking I was getting. John started to whisper in my ear. “Oh, you’re a fucken nasty whore, your pussy-ass is on fire…you’ve got my cock sooo hard, you dirty bitch!”

I broke up the position and ordered the guys to put the mattress on the floor. I ordered Curtis to lie towards the corner of the mattress and put his feet on the floor. I got on top, facing away from him and spread my legs over his – I had John swing over towards my face and started to lick his shaft and wrap my hands around his super thick cock and tongue-lashed his head, after a few minutes I had his pipe deep in my throat, flicking out my tongue along his swollen shaft, meanwhile Curtis was ramming his black Python snake into my smoking hot ass-hole.

John pulled away and started to lick the seam of my stockings down to my ankles – then he took off my heels and licked my toes through my stockings. My goodness, it was driving my crazy!

I need a small break – I got to my feet walked over to the full length mirror and adjusted my stockings, made sure the seams were straight in the back, I put my heels back on, touched up my make-up. Curtis went to make himself another drink, John came up behind me and wrapped his muscular arm around the front of my waist and whispered “Let me carry you to the couch and fuck you hard and deep!”

“Okay, I’m easy baby…I love the way you licked my stockings.”

He cradled me over to the couch and I spread my legs apart for his rock hard pole. He lifted my legs into the air and put them on his shoulder – slowly he squeezed his cock into my waiting hole, I was in heaven – we slowly started to get into a passionate french kiss when Curtis showed up and wanted some head – which I was more than happy to do. His 13” cock had trouble fitting into my mouth, but I managed to slurp on that manly piston. John by this time had my legs pushed so far back that my heels were hitting Curtis in the top of his head.

I could feel John was ready to explode and I had Curtis’s dick deep into my mouth and I was working on having him erupt soon. All of a sudden, John pulled out and started to cum everywhere, all over my stockings, my wig, blouse – Curtis as well started to gush sperm all over my face and neck, they both were yelling at the top of their lungs as the explosion continued. I had hot cum spewing out of my mouth; unbelievably John was still squirting his juice all over the couch!

Later on I cleaned up and put on another hot outfit and we fucked all night into the morning. I’m addicted to dick, I love to dress like a nasty slut, in stockings (I don’t fuck without them) garter belts, high heels, tight shirts, the works – I love to please all night.

Same as The Hottest Crossdresser - Part 2 Videos

4 years ago
  • 0
  • 17
  • 0

Portrait of a Crossdresser as a Young Man

Portrait of a crossdresser as a young man By Sara Keltaine I didn't write this for others but instead as an outlet to release the demons that have haunted me since I was a child. Some might think this story funny, others might think it sad, and the people that think they know me the best would be shocked. I'm writing under a pseudonym that has become my alter ego but I will get into why's of that later. I've been told I was a happy infant and my memories of that time...

2 years ago
  • 0
  • 27
  • 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
  • 26
  • 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
4 years ago
  • 0
  • 23
  • 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...

2 years ago
  • 0
  • 150
  • 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
  • 25
  • 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
  • 43
  • 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
  • 32
  • 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
  • 65
  • 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
  • 24
  • 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...

3 years ago
  • 0
  • 30
  • 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
  • 24
  • 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...

4 years ago
  • 0
  • 22
  • 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...

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
2 years ago
  • 0
  • 24
  • 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
3 years ago
  • 0
  • 31
  • 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
  • 42
  • 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
  • 23
  • 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
  • 28
  • 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...

2 years ago
  • 0
  • 26
  • 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
  • 265
  • 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
  • 46
  • 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
  • 37
  • 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...

3 years ago
  • 0
  • 25
  • 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
  • 38
  • 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
  • 25
  • 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
2 years ago
  • 0
  • 24
  • 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
  • 28
  • 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,...

4 years ago
  • 0
  • 47
  • 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
  • 25
  • 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...

3 years ago
  • 0
  • 24
  • 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
2 years ago
  • 0
  • 29
  • 0

CL Memories 1 Crossdresser True Story

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...

3 years ago
  • 0
  • 35
  • 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
  • 22
  • 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
  • 33
  • 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
  • 17
  • 0

Sensual Game Leads To Steamy And Hottest Sex 8211 Part 2

This is the second part of my story-Sensual Game Leads To Steamy And Hottest Sex – Part 1 So continuing my story after the first task was over everyone was so excited for the next task and that I had planned very nicely. For this task I asked all of them to remove their shorts and show me their dicks and the one with the biggest cock will get to touch kiss suck etc my beautiful pink pussy and my waist and belly. Because my breast and lips were already given to rahul so the one with the shortest...

2 years ago
  • 0
  • 42
  • 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
  • 21
  • 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
  • 24
  • 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
  • 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
  • 404
  • 0

Antheas baby 1

“What’s wrong? What’s wrong?”Anthea looked up at her mum as she sat down at the dining table. “Nothing is wrong,” Anthea responded watching as her mum hurriedly dried her hands with a tea towel.“Is the baby okay? Are you okay? Is Jack okay?” she asked as her husband came into the room and pulled up a seat at the table.“We’re all fine Mum,” she responded exasperated with her mum’s anxiety. “I have something to tell you.”“Sit down Helen,” her dad snapped. “Give the lass a chance to speak.”Anthea...

2 years ago
  • 0
  • 42
  • 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
  • 59
  • 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
  • 36
  • 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
  • 19
  • 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...

4 years ago
  • 0
  • 324
  • 0

Uther

Uther By Ellie Dauber (c) 2006 Introduction According to the legends of King Arthur, Merlin changed Uther Pendragon into a double for Duke Gorlois, so he could spend the night with Ygraine, the Duke's wife. Ygraine and Gorlois had three daughters: Elaine, Morgause, and Morgan le Faye. During their time together, Ygraine became pregnant with the child who was to become King Arthur. Uther's men killed Gorlois that same night. This is my TG (of course) version of what...

2 years ago
  • 0
  • 78
  • 0

Fernanda Peituda Safada hottest stories part2

Below a new set of real life stories about a beautiful hot Brazilian women Fernanda, nick name Peituda Safada.You can meet her at the strip-club Rota96 in Curitiba Brazil!Fernanda & Paulla entertaining a guy.I had sex 2 days ago with together another dancer from the club:An american guy wants see how 2 girls do lesbian sex.He orders us to put out all clothes, only we must wear our shoesAfter that we must kissing. He wants see how our tongue goes deep in each other mouth .We must play by...

2 years ago
  • 0
  • 22
  • 0

Sex With The Hottest Girl In My Class

Hi Friends, My name is Erik. I am 27 and i work and stay in Bangalore. This is my first story in ISS. It is about how I fucked my girlfriend when I was in 12th class. Coming to the story, it’s about my first love making with my the hottest girl in my class whom I fucked her in her house when no one was present. I moved to a new school in a new town and she was in my class. Her name was padmalaya. She was very fair and good looking. she was the hottest girl in class. Slowly i started to chat and...

2 years ago
  • 0
  • 21
  • 0

How Jeff Became The Hottest Girl In The World

*** Sore Thumbs and all characters are the copyrighted property of Owen Gieni and Chris Cosby, I am simply a huge fan! Please support there amazing web-manga. **** "How Jeff Became The Hottest Girl in the World" by Serena Kaden Hi, my name is Jeff. And this is the story of how I became the hottest girl in the world. I was a short curly-haired skinny loser of a man. At twentyfive years old, I had never been with a girl before. Wanted too badly, but I got nervous around the...

2 years ago
  • 0
  • 308
  • 0

Carruthers Bride

The the wind howled around the quayside as I stepped onto terra firma for the first time in weeks, the wind threw sharp shards of ice to sting our faces as we looked up at the sails as they were finally furled and stowed as our captain grinned at our discomfiture, "Au revoir!" he joked as if he knew we should soon be recalled. Those such as were left, and we were few enough, I shuddered. My best uniform packed securely in my Valise, awaited me, and just a few more duties before I...

2 years ago
  • 0
  • 19
  • 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
3 years ago
  • 0
  • 20
  • 0

The Young Crossdresser Part 2

So after my little adventure at mom and dad's bookstore,the next couple of years were uneventful. I did have sex a couple of times with Phylis,the older lady that was part of mom and dad's swinger group. I knew that I was wanting something more,something was still missing and I kept thinking back to how the guy's cock felt as it spewed cum into my panty covered ass. Now I was 15 and one weekend my parents went away with some friends and I knew that this would be the perfect oppurtunity to...

Crossdressing
4 years ago
  • 0
  • 22
  • 0

The Young Crossdresser Part 3

So the next night arrives and once again I find myself dressing up to head back to mom and dad's porn store to see if my lover from last night might be there. We had scheduled to be there around 8:00pm. I arrive in my car,check myself in the mirror and go inside. I see him instantly standing in the front looking at magizines and walk over to him and say hi. He smiles and looks me up and down and tells me I look hot tonight. He asks me if we could go back to  my place since my folks were still...

Crossdressing
2 years ago
  • 0
  • 28
  • 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
1 year ago
  • 0
  • 281
  • 0

Motherless Vintage

Do you know of the porn site Motherless.com? You should. I’ve reviewed it a few times on my site, The Porn Dude, although it was for different genres every time. This time around, I’m going back to this place and looking at a specific and niche little category many of you are just begging me to cover. We’re looking at vintage porn today. While it doesn’t have the same resolution and quality as the porn you can find today, it’s definitely a genre of porn that has a lot of personality to it and...

Vintage Porn Sites

Porn Trends