Cross Dressing free porn video

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

Hello is my story. This happened.

It was the mid 80’s and I just turned 17 so I thought I would go to the mall near my home town on Long Island and go shopping with my birthday money. I was looking for clothes with and I need to use the rest room. I walked into the bathroom, and the floors were wet so when I made a turn, I slipped. I put my hand against the door of a stall that was closed as not to fall, and the door it flung open because it was not locked properly. I looked inside and a man was sitting on the toilet jerking off. We looked at each other and we both froze, not knowing what to do, him with embarrassment and me shocked seeing a grown man jerking off. I looked down at his cock and stared at it because it was much bigger than mine. It was about 9 or 10 inches which is twice my length.
Finally the shook wore off for both of us and he smiled at me as he saw me staring at his cock. He was a handsome man about 28 or 30, blonde hair with a mustache. His cock was still in his hand and motioned for me to touch it. I don’t know what overcame me but I walked in and took it in my hand and started rubbing it. What happened next surprised me as I don’t know what overcame me. I took to one knee and started sucking on it. It wasn’t for long just a couple of times, but I knew I had to have more. The problem was the bathroom was not the place for this.
I stood back up and he started caressing between my legs, but I pushed his hands away and told him we needed to go somewhere else perhaps his car. My plan was to follow behind him, walk back to his car, and there I would have sex with him. Stepping out of the stall I let him go past and I got a whiff of his cologne which I can still smell today, Aramis.
He walked out of the bathroom and I followed behind him about 30 feet, he kept checking behind him to check to see if I ran off. We went out the door and to his car, getting in, It was obvious we had to drive to a more secluded section of the mall. We drove around the mall a couple of times and found a spot we thought would work. He parked the car and started to unzip his pants when a security car drove by and looked at us. The guard drove by several other times and it made us uncomfortable. Since he was older I asked him why not go back to his place and we could take our time. My plan was rejected because the last thing he wanted his neighbors to see was a slightly built young man going into his home. The truth be told, I was 17 but looked 15. I am 5’6” 120 pounds with a slight build.
My suggestion was for him to drive back to his house and drop me off on the block behind his house. I then would give him time to get back to his house and unlock the back door. Once I thought he made it back to his house I would cut through the property and walk into the door leading from his backyard. He was thinking about it and the thing that made him go ahead with my suggestion was my hand stroking his crotch outside his pants. It’s amazing what a guy will do with a hard on.
So he we put my plan in action and I gave him the time needed to get back to his house and ran through the house behind his and into his the door in the back. He was looking out the window to make sure no one saw and no one did. There is that moment when you look at each other and no words need be said and we both knew how this was going to play out. Looking at him, he was much bigger than me, over 6 ft’, muscular and very good looking
We embraced each other and started kissing. I thought I was going to cum right there and then. He was taking the lead and led me back to his bedroom where he laid me onto his bed. We started making out again and caressing each other’s bodies. The clothes started to come off and all that was left on were my jean cutoff shorts. I stood up to take them off and I noticed his wife’s dressing table and make up stand. Looking at it, I got an idea.

My sisters were always talking about their makeup and discussing between them how they applied it and had countless times seen them put on their makeup. My thought was to put on his wife’s clothes, and wear her makeup so I could pretend to be a woman. I asked him for a few minutes to get ready and told him I had a surprise for him.
His wife, who was working that day, had some very nice lingerie, and quality makeup. I took my time choosing an outfit and started applying her makeup. My outfit was all white, with stockings, garter belt, panties, gloves and a camisole. The high heels were the finishing touches to the outfit. Finished, I walked out to the bedroom, using my sexy walk. The look on his face said everything. His mouth drooped and his cock saluted me.
I strolled up to him, went to my knees and started stroking him and quickly put him in my mouth. I took my time and tried to swallow as much of his cock as I could, I got about 6’inchs down my throat. He put his hand on my head and leaned back and moaned in enjoyment. He started bucking before I knew it there was nothing left to swallow. The whole thing was down my throat. A couple of more deep throats and he blew his load. It was thick and creamy and I swallowed it all.
I started kissing him so he could taste himself. We explored each other’s bodies some more, and he started to rim me. A tongue slipped in, a finger, then two. He was hard again and he started rubbing his dick against my rosebud, spit on his dick then took the plunge into my ass and went deep. My god it hurt, I told him to stop but he said wait it out, I would stretch and it would not hurt so much. He was right. He spit some more onto his cock then start to ride me. I looked into his eyes and I was so turned on. He started calling me sweetie and telling me how sweet my ass was. I pushed back now onto his cock and he could only moan. He picked up the pace and you could hear the slapping sound as his cock plowed into my ass. I came all over my chest and he saw that and smiled. He wouldn’t last much longer and before I knew it he planted his seed into me. He collapsed on to me and I could feel his cock shrink. My ass eventually squeezed out his now soft cock.
We started making out and he got off me and we both knew it was time to clean up and have me leave. We got together many times after that. Eventually his wife came home early and caught us and divorced him. I never saw him after that.

0
0

24.07.2022
9
0

Same as Cross dressing Videos

Crossover

Crossover Janet L. Stickney [email protected] There was never any doubt that I was going to be a girl someday. I mean, from early on I would wear pale lipstick and eyeliner with my hair usually braided. Then came the Crossover week and I was able to dress like a girl from the skin out, complete with hips and boobs. My father was a drunk that never cared what I did, and my mom was long gone so how I dressed was never an issue. I work at a small shop that makes and repairs video...

Crosstraining

Cross-training Belladonna "Are you ready, pet?" "Yes, mistress," George Bloom responded as Celene knocked upon the iron door. George heard the loud clink of the old fashion knocker upon the door as he pulled at the hem of his short skirt. He anxiously waited for the door to open, hopeful that he would not be noticed by those passing by on the street below the staircase leading to the porch he was standing upon. George had never been to a Dom-sub party like the one that his...

Cross Dressing Cock Slut Party

Sadly this wonderful story is just a fantasy, but who wants to make something similar a reality!?!The evening had taken a while to arrange, but had finally arrived. All 5 guests turned up within 15 minutes of each other and as they did, I fixed them a quick drink and showed them into the living room to get to know each other. Alan was a suited businessman in his mid thirties. Dave and Brian were dressed casually in jeans and Tshirts and both in their mid forties. Jeff and Keith were my age,...

CrossFeed

Cross-Feed --------------- This is the first story I've written in a while. I have started several stories, but put them on the back burner because I just can't find a good ending for them. I always want to get a story 'just right'. Anyway, here's my latest installment. There is really no TG or cross dressing in it, but I feel it belongs in the genre in a weird sort of way. I hope you like it. --------------- He was a stallion, and she rode him hard. He did not...

Cross Dressing Led To Sexual Heaven 8211 Part 1

Addiction lets you do anything.. I addicted to cross dressing, addicted for the femininity.. Hi, I am 24 old close door part time cross dresser from Mumbai, regular reader of ISS. Narrating my own story for first time. I am good and beautiful looking, 5’3” height, perfectly slim as like every “women” wants to be and every man feels to hold, as I kept it with having exercises and yoga because I feel sexy with it.. I started cross-dressing when I was only 12. I haven’t knew it was called as a...

Cross Dressing Lover

The weekend started off the same as any other for Dhiren. He threw off his drab male work clothes with alacrity and stepped into the shower. He shaved his face, legs and pubic area as was his custom, then, after turning off the tap, moisturized his legs, stepped into a pair of lacy pink panties and hooked on a matching bra. The feel of the light, soft, feminine fabric had always been a thrill to Dhiren, ever since that fateful day when, aged fourteen, he found himself alone in the house all...

In her Dressingroom

With a make-up wipe I took the orange glaze, the white glitter and the sweat of my face. It was always such a satisfying moment. After the show was done, my muscles sore, I would take off the sweaty costume of the Sugarplum fairy, but before I jumped into the shower of my private dressing room I first took the make-up off my face. Seeing the Sugarplum fairy disappear and my own face reappear. A moment of self care. A moment off calm, no sounds, no music, just the soft rumbling of the...

Sidedressing

Sidedressing By Tyrone Slothrop Older sisters can be a boy's good friend and most effective torturer. Bernadette, charged with watching her little brother, was getting bored and decided to see how far she could manipulate him. Nothing nasty just keeping her hand in. Practice makes perfect. "Ralphie, come here, I want to try a new game." Ralph heard his sister and put down his videogame. He wandered into her room. At thirteen he was fairly average in height, about five feet...

Crossroads RulesChapter 5

Sid arrived in class early to watch the arrival of Cynthia. It was her grand unveiling - the first day in which she was going public, wearing her new wardrobe. He wondered which of the new outfits she would wear. He hoped that it was the blue dress since it was the sexiest of them. When Cynthia glided into the room, even Sid was surprised at the transformation. The loose fitting blue dress came down to her knees, was tight at the waist, and had a plunging neckline that just begged a man to...

Cross One Mans Journey into Darkness Part One

No light reached this part of the room. The solitary sunbeam that had managed to poke its way through the curtains fell on a dirty heap of ripped up clothing in the far corner. But here, there was only darkness, and the ragged breathing of the room's sole inhabitant. Tyler lay naked, his arms and legs strapped to the corners of the bed with leather belts, allowing him no room to move or stretch his sagging limbs. Premature wrinkles lined the strong, angular features of his now gaunt visage....

CrossDressed Fairy Tales 3 The Adventures of Pierrot

Cross-Dressed Fairy Tales Part 3 By Dawn DeWinter In parts 1 and 2, Sherry and Sadie, two married men, went to a lesbian bar on their "girl's night out." There they came into the clutches of Mike and Big Sue, and are in danger of being raped - or worse - if Sherry cannot keep Big Sue entertained with "original" stories. This task has just become a mite more difficult with the arrival of two more people. Can they too be kept satisfied? Part 3 is based on Pinocchio, the story of the...

Consequences of Cross Dressing

Consequences of Cross Dressing by Cindy Johnson ([email protected]) My dilemma was that I masturbated all over mother's gown and nylons and I frantically tried to clean everything up as fast as possible. I was frightened that it would leave a stain and I didn't know what to do but after twenty minutes of cleaning everything with soap and water, I felt like I was in the clear. I put everything back where it I found them and ran to my room reflecting on what had just happened. I...

Crossroads A Young Hero

I walked through the headstones towards Dad's car. It was my car now after that accident. I was walking away from the double funeral for Mark and Carol Arrowstone. It was less than a week ago that I had come home to the cops sitting in my driveway to tell me that Mom and Dad had been in a car accident. The drunk driver that hit them was dead too. Standing next to the car was Mike Larter, Dad's lawyer. He was handling the reading of the will and the distribution of my parent's assets. I knew...

Crossdress dreams come true

A seductive CD fulfills some of my secret fantasies. And I bring him pleasure into the bargain.Jeez, you bust your ass all year to be among the top sales people so you can get invited to the annual conference. Supposed to be in Hawaii or Vegas or somewhere exciting. And what happens? The company needs to save some money and holds it in the city where it's based. Cincinnati. For fuck's sake. I nearly didn't bother but there'd been some lay-offs already this year, so I decided I should go. You...

Cross Dressers First Time

I was in my mid 40's and divorced and living a great life. I ran my own successful from home and lived in a large house in it's own grounds at least 5 miles from my nearest neighbour.Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet up for sex or go away for a break all no strings attached. They all knew of each other and I was aware they saw other men or ladies if they...

Crossdressed By Friends 8211 Part I

I have been cross-dressing since the age of 15. I like to wear saree, suits and lehngas. This is a story about me getting dressed up by my friends when I was doing my engineering. My group in college consisted of 3 guys and 3 girls. The girls were all staying at their places and I had rented out a place in the city with my relatives. Two of my other friends used to stay in the boys hostel. This incident happened in the third year about a month before the exams when the guys had gone to their...

Cross Dresser Enslaved

CROSS DRESSER ENSLAVED A Fictional Account Of A Cross Dresser’s FantasiesPROLOGUEI am a cross dresser and a slave to my wife and her friends. Let me tell you how I got this way. Since I was a little boy, I liked being tied up. I had always had a petite, almost feminine body. When I was 15 years old I started dressing in my mother’s lingerie and fucking myself with whatever I could fit inside my ass. I also gave my first blow job to one of my friends. This was my only sexual experience with a...

Crossword

I so needed a vacation badly. I couldn't find more than a part-time job, my apartment was too small, and I'd been single so long that my mother thought I was a lesbian. I couldn't believe she asked me if I was gay last week. The question just made my mind spin. I was in a dire situation, the best and cheapest idea I could come up with was to spend an off-season weekend at a nearby ski resort.When I arrived the place was all but deserted. Perfect. I went up the steps to the lobby and approached...

Ultimate fetish dressing

0. She was sitting on the edge of her bathtub completely naked looking out into her bedroom with a kind of thill of anticipation. She had had a full bath and had just finished shaving her body except for her beautiful dark hair. She also had been given several huge cleansing enemas, until what she expelled was as clear as water. She wasn't a perfect girl, she new, slightly smaller than usual with her 163 cm, and she wasn't as thin as some of her friends, but she had full breasts and an inviting...

Cross Country Flight

I wasn’t looking forward to this flight. I hate flying cross country. It’s long and the planes are usually packed. I was fortunate that I had found a straight flight, no stops or layovers. As I settled in my seat, all the way in the back, I tried to relax. This was going to be a red-eye flight so I hoped to get a little rest along the way. As the plane filled, I watched the people getting on. Travellers are interesting people. I hoped I would be spared any travelling companions in my row. Just...

CrossDresser Delight

As a cross dresser you feel like such a woman when you have on your sexy panties and bra, and other feminine unmentionables. Sometimes you just wear them underneath your boy clothes. But sometimes I like when you have a dress and even high heels on too. I get to look at you, a beautiful and sexy woman. You get to tease and titillate a guy like me with your sexy body. You make me so horny and hard when you prance around the house looking so pretty. You always wiggle your sweet ass when you...

Cross Dressing to go to Girls School

As a boy I was slim and in some ways feminine looking. For example it used to annoy me when I went into a shop with the hood of my coat up because of the weather to be addressed as “hen” rather than “son” – these being terms used in the Glasgow area back then. I went to a co-educational school and had a great time with the girls I met there, all the way from my first day in “primary one” to the sixth form. I did have a fling with one of the PE teachers there brought on by too much to drink...

Cross dressing journey

Hello everyone I wanna tell you all about my cross dressing fetish and how it all started. Before I begin let me start by telling you all a bit about my family and myself. We are a family of three, my mom, dad and myself. Both my parents worked which gave me a lot of time to be alone. Although both of them worked it was my Mom who was the main bread earner of the family. Her name is Shikha and she is the vice president of a private company and earning a good salary apart from amenities like...

CrossDresser Loves being used

I have cross dressed for almost fifty years. It started in the UK when I was eighteen, I had often read the various catalogs for mail order purchases and used to look at the women's lingerie pages where the ladies were wearing garter belts, girdles, panties, stockings etc., and I used to get hard and play with myself and jack off to the pictures.I was always fascinated at my older sister who used to wear stockings, garter belt, etc. and it excited me. One day when nobody was home, I went to my...

Cross dresser caught at home by wife and boss

Let me start off by saying that i have been secretly cross dressing for about 8 years now i also go to the local bookstore for an ocasional blow job ( i give and recieve ).I have been wanting to suck and be fucked for quite some time now and it is about to happen. It started when the wife brought home some fine under garments i just had to feel for my self. I was hooked and started a small collection of clothes . I dress up when the wife is away at meetings. Well as i said i was working at home...

My Road to cross dressing

I was bought up in a time when taboos about something alternative like transgender people or cross dressing was still considered to be a no go area. Society made one feel that you were an out cast or mentally ill. Luckily times have changed and it has become much more acceptable, even though we still have a long way to go. I first started dressing when I was about eighteen. My sister had this old green dress that she had thrown away. I remember liking that dress and secretly retrieved it from...

Crossroads Part 1 fiction

CrossroadsI had a lonely couple of years with no job and without much contact with other people and I really was beginning to find life a bit lonely after my divorce and eventual move into a small flat. What I really would have liked is a partner, someone to share things with and most importantly someone to come home to. Having seen an advert for help wanted in a charity shop in my town I thought I might try that as a way of meeting people. I was taken on and over a short period of time I was...

French Dressing

French Dressing Chapter One: Mr Fox Everything I am I owe to Mr Fox. That is such a strange statement that I suppose I will have to explain it. See, when I went to secondary school I went to a single-sex school. That's slightly odd in its self, I know, but that's how things were organised where I lived. And for the first two years Mr Fox was both our form master and our English teacher. And for most of that time nothing out of the ordinary happened. And as for me, well I was...

How I Got Intyo Dressing

From the begininng when Kerry and I started dating it was ALL about SEX. We could be anywhere at anytime and she would jump me. It would start with the question "Do you trust me ?". Then in elevators, department store dressing rooms, movie theaters, airplane restrooms, just about anywhere, we'd be having great sex. She would try any type of sex or any position in any place, nothing was off limits it seemed. I knew once she asked me that question I was about to have sex in some place or in...

Friends With Benefits 8211 CrossDressing

Hi sexy people. Hand shake to guys and boobs shake to girls. I appreciate your comments on my previous stories. I’m going to narrate one more story which could be few people’s fantasy – Cross dressing. So let’s get started. Well one day I was hanging out with my fellow colleague Sindhu. We were quite close, as in, we have had sex couple of times earlier. But we were not committed. In fact she had a boy friend who was still a virgin. That means Sindhu never had sex with anyone else. We were not...

First time dressing

I do not claim to be a grammar expert and as such you will find some grammatical errors in this story. The errors can be the switching of tense, spelling errors, or typos. I ask if you find an error please send me an email so I can correct and make the story enjoyable for others.WARNING! This text file contains sexually explicit material. If you do not wish to read this type of literature, or you are u******e Eighteen, PLEASE DELETE THIS FILE NOW!!!!II did not know I had a disorder did...

My neighbor blackmailed and fucked me for Cross dressing

I had recently moved in a townhouse unit in Oklahoma. Still trying to adjust to the new neighborhood, I was also doing my best to keep my hobbies a secret. You see, I am a cross-dresser by passion. But my new neighborhood is strictly catholic and I can imagine the uproar my fantasies might stir. My next-door neighbor was an old man in his 60’s. He looked younger and stronger than his age. But, my secret unfolded and the neighbor fucked me for cross dressing. Within a couple of days of...

Dressing

Dressing Synopsis Many people see me as a girl when in girl mode, But I am not. No, I am a guy blessed with an androgynous body. [-][+][-] I am Robin Lee Anderson and due to my small size, can successfully dress as a boy or a girl, which pleases my wife Maryanne Lee as she has both a loving husband and girl friend rolled into one. Growing up, my parents had fun dressing me and my twin sister Roberta Lynn in identical outfits as well as outfits of the opposite gender to confuse their...

Salad Dressing

At the age of eighteen I got involved with Pierre, a man almost twice my age. Given the history of his former relationships I should have seen the writing on the wall, because by the time I was twenty-six, I had become too old for him. I was replaced by a nineteen-year-old, who was twenty-three-years younger than Pierre. Pierre only liked young meat. The bust-up was disappointing but not particularly traumatic, and my generous settlement assuaged my disenchantment.I moved to a small town where...

Cross dressing gay fantasy

I would wear black stockings and no other clothes. My whole body would be shaved. I put on cream that makes my skin look even whiter and blemish free. I want my skin to look as feminine as possible. I would wear a jet black wig like a messy bob. One were I can pull the hair over to partially cover my face. I would wear oversized black sunglasses with dark red lip stick and maybe some temporary acrylic nails. I sit on top of the kitchen work top with my knees up at my chest and feet crossed...

Crossdressed in public

hi ppl i m rohit….i m 16 yrs old and i live in delhi…i love to crossdress when i m all alone. i hv been doing this sicne i was 13 yrs old.i used to wear my mom’s clothes n gaze myself at mirror. though i was not a gay but i wanted to try gay sex once by turning to a women. it was in d month of june when my parents had to go to noida for some work and i was left all alone at home for a week. one evening i thought i should try crossdressing and go out to enjoy in public n tease some ppl.i...

Crossroads RulesChapter 2

Sid stepped through the portal and gazed upon the loveliness that was Sally Caretaker. It was hard to believe that she looked even lovelier since his last visit. All thoughts and questions Sid had wanted to ask flew from his mind to be replaced by desire for this woman. He moved to her like a man possessed. Sally’s smile could have lit the night brighter than a full moon. Her translucent green gown hinted at the treasures it contained. It captivated him and drew his eyes to seek out glimpses...

crossdress in tight flared jeanswent out in publi

well i have always crossdress and dressed up in my house but that recently has turned boring. i figure do something more thrilling and excited. i desided to put my tight junior size 9 flared jeans and go in public. I know that if someone saw me i probably ganna get laught at. so i started practicing by wearing the jeans and going outside my house like in the back when it was night. it really felt so good. the tightness on my hips and ass and seeing the sexy flare of the jeans made me feel so...

Crossdress Sex 8211 Mami Fucks Using Strapon

Hi my name is Sunil(although I call myself Sunita). I 29 and I am a beautiful crossdresser with very nice body. I own three beauty parlor in Delhi, and I am always dressed as a girl. I go out wearing woman clothing and no one can say that I am a boy. Now coming to the story, it happened 10 years ago. I was 19 then. I was bottom crossdresser then also and had sex with many top guys until then. I was fair and my body was very girly. I had a round bubbly ass although my boobs weren’t developed...

Dressing

Dressing Janet L. Stickney The inability to express oneself is one of the worst things I can think of. Myself, I didn't know that boys were not supposed to wear dresses until I showed up at the dinner table completely dressed as a girl. I was about 5 or 6 I guess. I can remember my dad going ballistic, and right after dinner mom had me change back into my own clothes while she told me it was wrong for boys to dress as girls. After that I was always careful so as not to get...

Summer dressing

It was the mid 1980s, I was 20 years old and it was the summer holidays. For the long break from college I'd managed to find a vacation job in Kent in the south of England. It wasn't brilliant but I was going to get some experience of working with computers, and earn a bit of money to keep me going during term time. The company was based in a small town where I had found a room in a house with a fairly old-fashioned landlady. The freedom of being fairly anonymous in this new job and town was...

Cross country run

Three of us were on a cross country run on a summer’s day when we fell victim to a sudden thunderstorm. The rain came down in sheets and we were thoroughly drenched. We were each wearing white shorts and thin white vest and embarrassingly these were now completely see-through. The rain kept pouring down, and we finally spied a cottage up ahead and decided to seek shelter. My two mates huddled behind me as I knocked the door. I covered my crotch as best I could. The door opened and a vision of...

Cross Driving

I was 'cross-driving' through one of our state parks on a beautiful summer afternoon. Cross-driving is what I refer to as dressing up (crossdressing) and going for a drive to get my juices flowing and to see if anyone else is up for a little action. There are a few older gentlemen that like to cruise the state park to look for a little action and today, I was hoping to entertain a few. With my dark cosplay wig with little ponytailes, short school girl skirt and an oxford style shirt, I had...

Cross Country Slut Part 5

Cross Country Slut, Part 5We made it to our destination for the load, a few days later. I made it my job to keep Bill happy and myself well-fucked. Neither of those things seemed to be a problem for us; I was always happy to please him in any way I could. My only little problem was the case of NSU that was persistent as hell. The discharge continued along with the burning sensation when I peed. All I could do was keep a supply of cranberry juice around and drink a lot of it. It didn’t help that...

Cross Country Slut Part 4

Cross Country Slut, Part 4I woke up in the darkened room [at least I realized it was a room] my first realization was that I was sore; not only my gaping cunt but up inside. My insides had really been re-arranged. I also realized that, not only did Bill have me firmly in the spoon position – with his cock jammed between my cheeks – but there was another body in the bed. As my mind started to work a little better, things started to cum back to me. I would find out later that, not only had I had...

Cross Country Slut Part 3

Cross Country Slut, Part 3Once things had returned to normal – whatever the hell that was/is – we just lay there for a while in basic ‘recovery’ mode. I finally stopped shaking like hell all over and could breathe kind of normally following a lot of hugging and kissing. I found myself wondering if there would be a knock at our door; I’d been a little loud. Bill thought it was funny; he was also amazed.Yep, that had been a true multiple orgasm.I was glowing so hard that I was just tingling all...

Cross Country Slut Part 2

Cross Country Slut, Part 2The next morning I didn’t know where I was at first; I DID know that someone had given me a good sexual workout. My cunt was raw, I had general aches all over and…my insides had been re-arranged. In some ways I’d always found the first and last things, as far back as I could remember, kind of erotic. I’d had a good time. Without disturbing the sleeping Bill; I slipped out of bed and made a bee-line for the bathroom; I really had to pee! The sun was coming up so, I...

Cross Country Slut Part 1

Cross Country Slut, Part 1It began as just a little on-line chat in one of the old Yahoo chat rooms. It became private and steamy after a while. I asked him to wait for a few minutes, did my hair and a little makeup then, turned on my web cam. For the next few hours we chatted as things became VERY hot. By the time we said ‘good night’ I was sitting on my favorite butt plug, I’d cum twice – my panties were long gone after I’d made a mess in them after a while – my nightie was up around my waist...

Cross Dressing Pegging and the Promise of a Three

After my last session with Ann, the gorgeous older woman (we’d call her a MILF nowadays) who’d discovered my love for cross-dressing, things were quiet for a couple of weeks. She’d only ask me to visit her when she knew her husband and son would not interrupt which so far meant when they had gone off to watch their football team playing away. It seems that they had a run of home games.Mind you, keen as I was to play with Ann again I did also enjoy replaying our sessions whilst lying on my bed,...

Cross Dressing play turned horribly wrong fantas

It was just another warm Sunny weekday morning like any other in summer. My wife kissed me goodbye as she left for work, I took my usual pervy glance at her as she wiggled her hot behind out the door, I was setting up in my home office, ready for another day of working from home. I listened to the car roll out the driveway then the gate closed, I started working through the usual emails and meeting requests.. I got bored of work after a couple of hours I decided to go into our bedroom and rifle...

CrossDressed Fairy Tales Snow White and the 7 Trolls

Sherry and Sadie, two married men, have a girl's night out at a bar. The evening goes badly and, like Sheherazade, who related the 1,101 tales of the Arabian Nights, they end up in great danger, desperately spinning stories to protect their derrieres. For material, they transgender fables they have read, hoping that their captors won't know the original. Will this strategy work? It will depend on you, the reader, because Sherry and Sadie will soon run out of ideas unless you...

CrossDressed Fairy Tales Rapunzel

Some familiar fables transformed for readers of transgendered tales. In part 1, Sherry and Sadie, two married men on a "girl's night out" visit a lesbian bar and go home with Big Sue and Mike, two women who are dangerously upset to discover that they've been seduced by two cross-dressed males cheating on their wives. Like Sheherazade in the Arabian Nights, Sherry decides that the only way to protect their -- um, posteriors, is to entertain Big Sue with fabulous stories. ...

Crossdressing the beginning

I would assume that for most men, interest in women’s clothing started at a young age. For me, this occurred when I was 11 looking through the Littlewoods, Gratton and Freeman catalogues that my mother used to have.At the time, I lived with my mother Jane, who was divorced, my brother Anthony and sister Sharon, who were five and three years older than me. It was quite easy to sneak one of the catalogues up to my room and thumb through them. If one of them had bothered to look at the catalogue,...

Cross Country Vayage For Sex 8211 Part II

We all got ready to look around Liverno City. It was almost noon time. Before we go out, Nila Used my ‘One sim card’ mobile to call her friend along with their parents in a’telecom’call to convince them. We disembarked from the ship but, the weather was not so favorable. We walked through the shopping thorough fare and bought some souvenir and gift items. We walked along the broad walk and shoreline. We had lunch in a restaurant . After the lunch Nila went to the bathroom. I asked Mila,”did you...

Cross country run

Three of us were on a cross country run on a summer's day when we fell victim to a sudden thunderstorm. The rain came down in sheets and we were thoroughly drenched. We were each wearing white shorts and thin white vest and embarrassingly these were now completely see-through. The rain kept pouring down, and we finally spied a cottage up ahead and decided to seek shelter. My two mates huddled behind me as I knocked the door. I covered my crotch as best I could. The door opened and a vision of...

Cross dressing for my boyfriend

My name is Chris and I’m a 25 year old, white, bisexual male. I stand 5’9″ and weigh 135 pounds with light brown hair and brown eyes. I’ve always had somewhat of a feminine body and I’ve always enjoyed being a “bottom” when with other men. I met my boyfriend Mark about a year ago at a bar. The minute that I saw him, I knew I had to have his cock inside of me. Mark is 27 years old, 6’2″ and weighs 195 lbs with brown hair and a very hot body. He works out a lot and plays some sports. You could...

CrossDresser Fuels Feminine Passion In Sai Now Sindhu

Hi, My name is Sindhu (using a female name). Here, I am going to write about how I am smitten by my girlfriend’s brother and turned from a straight guy to a dick-loving cross-dresser. My girlfriend and I started living together after both of us got a job in the same city. Both our families knew about this, and they were cool with us. We were happy together; we were enjoying our life to the fullest until her elder brother came to stay with us and took me to a fantasy world which showed me how...

CrossDresser Fuels Feminine Passion In Sai Now Sindhu

Hi, My name is Sindhu (using a female name). Here, I am going to write about how I am smitten by my girlfriend’s brother and turned from a straight guy to a dick-loving cross-dresser. My girlfriend and I started living together after both of us got a job in the same city. Both our families knew about this, and they were cool with us. We were happy together; we were enjoying our life to the fullest until her elder brother came to stay with us and took me to a fantasy world which showed me how...

Porn Trends