Crossdressing HD Porn Videos

The Adult Theatre

I got to the hotel early so that I could get myself fully prepared to meet a guy I had been chatting with via a chat room. I decided to wear my favorite pink check mini skirt with my sexiest pink undies to match. I added a white silk blouse and a white garter belt with some white stockings. I took time applying my make up, making sure I had dark sultry eyes and perfect red lips, I wanted to look perfect for my date. It had been a very hot day and the temperature was still sticky even with the...

Joann s Club Paradise

Sis rented Mom’s old bedroom to two of the gurls on my soccer team. They would also look after the house so she and Chrissy could come down and join us as we spent the last week preparing for the grand opening of “Joann’s Club Paradise”. When they arrived, Sis and Michelle started on setting up the salon. They couldn’t believe how good the old motel looked. Chrissy set-up the booking and charge system while I worked with the newly hired cooks and bartenders stocking the kitchen and bar. Joe...

Where Did My Damn Key Go Part 3

Four days; I've dealt with four grueling days of not being able to touch myself. Jesus, how can anyone even do this without even going insane?!Ever since I crossed paths with that dominating bimbo, my entire routine had changed. And to be honest, I was surprised at how much sex was in my life. From the moment I woke up to the second I crashed and fell asleep, my mind was very frequently in the gutter, wondering when I was going to get some ass or where can I go to beat one off real quick....

Adventures of Kristof and Marci Part 1

ADVENTURES OF KRISTOF AND MARCI PART I The Meeting I sat on the chair in front of the computer, wearing a tiny black swing skirt, black nylons and red high heels. Beneath the skirt I wore a little pale pink lycra thong and I was naked from the waist up, save for the chain that hung at my chest, the ends connected to each nipple by a little clip. ‘I really need to pee’ I said. ‘Mmmm. Go on then, you know you like it. I think I will, too.’ Marci responded. ‘I can just...

Busted by My Step Sister s Boyfriend Chapter 1

My step-sister Alicia is two years older than I am and built like a Greek Goddess with her braided blonde hair, slender body, long silky legs, tight round ass, and 36D breasts. Her boyfriend Bob is a college freshman soccer player who regularly spends the weekends at our house. My parents do a lot of weekend travel to relieve the stress of their jobs, so the house is virtually ours to do whatever we wish when Friday rolls around.This particular weekend wasn't much different than the others. Mom...

Stage eight of my journey to becoming Joann

After returning home from dropping Mom and Dave off at the airport, I immediately jumped in the bathtub and took a long bubble bath. While I was in the bathtub, I shaved the stubble that was starting to form from days of neglect. When I finished my bath, I rubbed most of my body with a good lotion to restore its smoothness, followed by a badly needed pair of sexy red lace bikini panties with a matching bra. I pushed a pair of “B” cup self-adhesive breast forms into the bra. They are quick and...

Extended Vacation Part 2

Chapter Two in my novel of Cassie living 24/7 as a woman...please read Chapter 1 and let me know if you want more. EXTENDED VACATION Chapter 2 After experiencing a great sexual adventure less than two hours after becoming Cassie full time, I was now in a even better mood as I got back on the freeway and headed north. Due to the low air pressure in my tire, I drove around 50 MPH for about ten minutes until I saw a big truck stop and gas station at the next off ramp. As I took the exit, my two...

Confessions of a Sex Crazy Cross Dresser Part 3

Part 3 of Book #1. Chapters 5 and 6. Please review and let me know if you want moreChapter 5: Da’ Place Adventures Sunday that week was definitely going to be a day of rest. After all my adventures on Saturday including a coast to coast airplane flight, I was exhausted. Collette called me and asked me if I wanted to get together tonight and I asked her for a rain check. I ran some errands during the day and late afternoon I spent watching a football game on my television and around 6 PM when...

Jessie and the Office Girls

I spent the weekend trying to recover from the pounding that I received from Dan, Aaron, and Zach. I was their slave, and I had enjoyed it immensely. What I didn’t plan on was having all of my moans, groans, and enjoyment being filmed from twelve different angles, along with Dan telling me that he was going to share this video with our office mates. I was worried, yet anticipating what Monday would bring to me in the office. Come Monday, my ass was still sore from what Dan, Aaron, and Zach did...

Jessie s Fantasy Chapter 4 The House That Adam Built

What a crazy twenty-four hours it had been. It all started last night with me losing a bet to my friend John, one which I should have never lost, but did. My payment was to dress up as a female while going out with my friends until I was able to successfully have a guy try to pick me up. Earlier today, I went to my friend Tracy’s house and told her about my dilemma. After a few laughs, Tracy took me seriously and enlisted two other friends of hers to help me pay my bet. I was too shy to tell...

Dan Becomes Dawn Chapters Three Six

Chapter Three: Coming Out! I felt much more confident, to the point of euphoria, as I drove to meet Andrew and Marie. Just having the seat belt bisect my bosom was a thrill.I found the correct address, parked in the driveway, took a deep breath, retrieved my purse and the bottle of vodka, went up the steps to the front door.Seconds after I rang the doorbell, Andrew answered. "Good evening, Dawn. You look fantastic. Please come in.""Thank you, Andrew. I am just a little nervous." I handed him...

Wifey s Panties

Our phone sex is always so hot; you egg me on in so many ways. My wife has no idea how much I wear her panties not to mention her lingerie, stockings and dresses. We talk about what I'd wear when we get together as I suck your cock. You always have me send you pictures of me dressed in panties, stockings and high heels, telling me how perfectly stunning my penis looks in silky panties and you tell me what a hottie little sissy bitch I have become. I tell you when I'm lucky and find a perfectly...

Cindytranee meets the maintenance crew

This is a true story that happened a few years ago when Iwas living in an apartment complex while looking for a house. I had taken a small one bedroom on the 2 nd floor. It was very nice and private and I really enjoyed being there. This was the first time in years that I had lived alone and I loved it. It gave me the freedom to enjoy my favorite thing, cross dressing and having sex with as many people as possible. I had settled into a routine of dressing up every night and all weekend and...

My Sissy Summer part 1

It was a hot summer and my parents had sent me to stay at my aunts house while they went away on vacation. My aunts house was huge, so big that it was easy to get lost in one of the many rooms that now lay mostly empty. My uncle had left years ago and my cousins had all long since moved out, all except for the youngest, Veronica, but she was away at college.My Aunt worked during the day so I spent most of my time in the house on my own. The first few days went really slow and I found myself...

Capri

Friend of the family -Bi Curious story This is my very first story, I hope you enjoy reading it and I hope it inspires you to contribute My name is Jools I grew up in the west country from the late 60’s until the present day My tale based on a true story happen in 1970. At the time I would be at the tender age of 16. When your young the time can't pass fast enough. cold winters and hot summers. Being a male and the eldest of six brothers, you could say that I had...

One On The Way The Conclusion

He had been in the makeup chair longer than he imagined he would be, but the results were worth it. As he drove he would steal glances at his reflection as he still couldn't believe the results. In the space of a few hours and thanks to the skills of the very talented makeup technician, he went from a typical American male to dammed fine looking female.As he drove, Ryan was thankful for the heavily tinted windows on his car which helped to hide him. He hoped to make it home before one of his...

Taking That First Step Part 5

Lana began to protest at being pulled toward the bed; she felt she had been punished enough. Her ass was on fire due to the spanking she had just received. Her protests were ignored.Lana was pushed face down on the bed and she felt Cassandra sit on her back before she could attempt to rise. She felt Cassandra attach something to her wrists. Lana opened her eyes and saw restraints. These were not the restraints made of nylons that had been used in the back of the shop; these were made of...

I did not know I had a disorder

I did not know I had a disorder CindyUSA I am not sure if I should be embarrassed, ashamed, depressed about my condition. I do not look unwell; does it show? I look normal to my wife, family and co-workers. I wonder if they know about my disorder. If they had, why did they not tell me? Like most illness, they start slow and build up and suddenly, bang; right between the eyes it hits you. Maybe for years I suspected, but not wanting to admit that to me. I did not think my condition was...

Cruising The Drive In

It was a Friday night and all of my friends were at home with family. I was really bored and I asked my dad if I could take the van and go to the movies. He said it was ok and told me to be home by midnight. The van was a 1977 Chevy van, it was brown in color and had the moon windows cut into the side. It had the typical "Captain' s chairs" up front and in the back had what you'd expect from a '77 van. It had a couch that turned into a bed. Around 7:00pm I grab the keys and tell my parents...

Being Joann

I sat in front of my computer and started surfing transgendered sites when I came across an article on psychiatrists specializing in cross-dressers, transvestites, and transsexuals. Some of their treatments included a psychological evaluation, hormone therapy, group sessions, and preoperative assistance. The mail order hormones I was taking were having some positive effects, but I read there were better and safer hormone medicines available by prescription. also really wanted to get some breast...

Getting A Grip On The Situation

As our story opens we find sixteen-year-old Ken almost naked and laying at Vanessa's side enjoying the slow descent from his orgasmic high. The wonderful feeling is made even better by the fact that Vanessa's body is pressed against him and one of her satiny smooth legs is on top of his leg.He smiles to himself as he glances over at her and recalls her asking him not to tell anyone. It was a request that was not really necessary. Being jacked off by your buddy that was dressed and made up as...

Stephen and Stephanie

As neighbors, Carol, Karen and I regularly met up on weekends during school term and more often during the holidays. We played many games together, and I happily joined in, despite their girly nature; I even played with dolls. Of course, the kids at school found out about this, and I was bullied mercilessly for being a sissy. I tried to explain that no boys were living nearby to play with, but in truth, I didn’t relate to macho boys while I was happy and comfortable with Carol and Karen. Our...

Towards an Advanced Degree Part Two

So it began. My next official act as Daddy’s submissive slut was about to begin. I was strapped by ankles and wrists into the sling. The sensations of complete helplessness had me even harder than I’ve ever been. I was lit up with an acute awareness of my sensuality and the need to surrender my body completely to him. My surrender was like some kind of strange relief in my heart. I was his and I was soon getting fucked furiously. My reflection in the mirror on the ceiling seemed incredulously...

Attractive to a Fault Part Two

Jack seemed more than surprised when he set eyes on me. I was soon aware that he also seemed quite pleased. As I stood in front of him dressed in sheer red silk, looking like a true bedroom seductress, I realized the true error of my ways! What in the world was I doing? Why on earth was I suddenly standing in front of him practically naked, like some kind of sensual, naughty sexy slut?Things immediately began to happen at high speed. Jack didn’t bother to hand me the roses. In a flash of a...

Telling Mom I m A Crossdresser Part 17 Seven Days Of Sex Days 1 2

This is a fairly long story but I broke it into two parts so that you can read the first half in one sitting and find your place easier if you want to come back and read some more. Also, I would like to say that this will be the start of a seven day sexcapade for Missy involving two of her past flings. Please enjoy and rate and comment at the bottom. Happy reading!! It was now Monday and mom had to work. I was left home alone and I had already began a 10 day holiday with about 8 days remaining....

Jamie s Gradual Grooming Part 3a

I gradually woke up from a deep and warm sleep. My slow awakening became very sudden as I came to two realisations. One, I was wearing underwear from the night before and two, they were wet! I quickly pulled the duvet up and over my head, as if lots of people were watching. I slowly put my hands into my panties and felt a warm liquid all over them, I'd had a wet dream. Straight away I tried to think about what I had dreamt, but I couldn't recall. I wondered what Mike would say and what he would...

An Introduction to Crossdressing Pt 2

So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. The right side had several racks of all sorts of women’s clothes including lingerie, dresses, shoes, wigs and...

Towards an Advanced Degree Part One

At age eighteen I had finally made it into one of the best universities in the country, yet my true life lessons and deepest learning would ironically take place for me during the weekends. I’ve had the complicated urge to dress up as a girl since my early teens. Eventually I consciously chose to act on my need to do so. Though I live a mostly normal existence and also do enjoy my male side, I was driven to find out more about the feminine side of my persona. A year ago at age seventeen my...

Ashley s Crossdressing Adventures

It's Sunday and Mommy wants to hear what sissy things I have been up to, and don't leave anything out Sissy Ash, Don't be shy, out with it sissy, I already know you love being a complete sissy!Did you buy anything sissy? Yes Mommy, I did, I want to hear, everything you bought you little sissy, let mommy remove your bra, to access your sissy nipples,Mommy I bought 4 pairs of sheer nylon panties to add to my collection, pink, blue, white and yellow.What else sissy? I ordered 3 packages of...

Night on the Town

Night on the Town Barbara Marsh“Well, come on, chicken!” I responded, “Cluck, cluck.” Okay, so I know it’s not original, but it was the best I could do. Despite my misgivings, I got out of the minivan, smoothed my skirt across my hips, and waited for Alexis. Her name’s really Alice, but she was Alexis for the night. The same way Jeanna was Gina and I was Betinna. I don’t remember whose idea it was, but it was supposed to make us more exotic. Yeah, right. Three going on forty (or slightly over...

The Feminization of Michael 2

The Feminization of Michael. Chapter 2 I continued with the “weekend” clothes for another few weeks and consistently had people commenting, laughing and making things difficult when I was out shopping. I continued at work in the more feminine suits and blouses too. The rumours increased and somehow word had got around that at the weekend I wore dresses and full make up! This couldn’t go on like this, I had come very close to being beaten up when I was out and the chanting was just crazy. My...

Being Christy Part 2

To be honest, I was panicking. From the outside I looked like an average teenager. Skinny black jeans. Indie band tee, maybe a size too small on my Bowie-thin frame. Cherry red Converse high tops. Straight dark hair cut into a fashionable (if you were an NME reading indie-kid) boy bob. But underneath I was sporting skimpy black panties and stockings and suspenders, all ‘borrowed’ from my sister’s underwear draw. Drenched to the bone and locked out of the house, I was having a Hugh Grant in...

I Still Love You Tomorrow

How could she be so forgiving? I didn't understand... Caught with the evidence of my secret on my face, my body, and in my hair, I was frozen by her stare as she stood in the bedroom doorway, eyes wide as teacups. “Oh,' she said, too shocked for anything more. I had lied to her! I wouldn't have blamed her if she had left me in that instant, but she stayed. Why? How? We sat together on the bed. I took her hands in mine and our eyes spoke before our mouths ever opened. She wasn't afraid, wasn't...

Attracting some attention

Like most people in their late teens and early twenties, I enjoyed going out to pubs and clubs. I would go out with my friends and my girlfriend, always in guy mode. I was still in the closet pretty much back then. I would dress up at home when I was alone, never venturing further than the back garden to have a sneaky cigarette in the cool evening air, but that was as far as I ever got. I would watch my girlfriend getting ready before we would go out and always feel a little touch of jealousy...

Steve the Crossdressing Cat Lover

My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please.Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land Steve has that he'd keep a couple of horses to ride but no. The barn is filled with cats that curl up and sleep...

My First night

This is a true story that I personally have experienced and wanted to share with like minded people. Thankyou. The evening drew closer after work which had been busy and made me rather stressed. I work as a graphic designer/illustrator in a well known and respected company. I left my studio in London and drove the twenty minute journey that I make, day in day out, to my flat which I share with my loving and devoted fiancée. Marie and I have been together for three years and have known each...

Jenny and Mike Date Night

It’s Friday night, but for me and my wife it’s Date Night. Most couples have date nights on Saturday, but we have it on Friday nights to get an early start on the weekends. Michelle and I have been married for a little over two years now and we live a very happy life. I was not always so happy because I am a crossdresser and have been dressing up ever since I was 16. I met Michelle when we were in college in 2005. She was studying law, while I was in the IT field. We met at a college party and...

My New Life As A TGurl Slut Pt 4 DP d By The Bouncers

Jack was the first person I met on my first night out dressed as a girl... a sexy, slutty girl.He is the head bouncer/ co-owner of the security firm that deals with security for various gay and tranny nightclubs including this particular TS/ TV/ CD club which was my first introduction to 'the scene'.And I must say it's an awesome club. The trans scene is much larger than I realised but this isn't just a venue that hosts transgender nights, it offers much more.It certainly isn't a sex club...

A Nanny Femtastic Chapter 11

A NANNY FEMTASTIC! Chapter 11 We walked to the harbour and found the boat. There were too bulky security guards checking people as they entered. The boat was in fact a massive cruiser! We joined the queue, it was obviously not a little gathering. The other women were dressed in classy whites and float summer dresses, we looked like too cheap hookers! “Trinity this was a mistake, lets go,” I said. “No come on honey who gives a fuck.” She linked her arm in mine and stood provocatively with her...

Girly Obsessions

All of my life from the time I was young to now at twenty-five, I have had an obsession with women. It is not that I like them (which I most certainly do) but more that I want to be like them, act like them, and most importantly dress like them.It started when I was very young and developed an interest in the legs and nylons of women which I found fascinating. The sheer and soft material was incredible to look at and to touch. I was entranced with the way girls' legs would look with them on...

This one is for Tracy

This story requires a short preamble. I had e-mailed erotic stories and fantasies back and forth with my friend Paul for several months. He liked to be a dominant, so one day I asked him to send me exacting instructions on how he would like me to masturbate, which I would have to do and then describe back to him. He sent the instructions, which involved me getting fully cross-dressed before sitting down to watch a particularly hot she-male video, and about a week later I was finally able to...

Bo Peep and the neighbor

It had been a hot summer and I had no luck finding a job. My parents did not seem to understand that there just weren't that many companies hiring that year due to the economy so they had really been pressuring me to find a job. They all wanted someone with experience but having just graduated high school I had none. I was nearly at my wits end so when I was asked to house sit for my uncle I jumped at the chance. He lived a half an hour out of town in a nice quiet neighborhood and had a nice...

A night at the resturant

I met John online; he was the owner of a small town restaurant, who was also married. I agreed to meet him that night after he closed. When I pulled up to the restaurant the lot was dark. I hustled up to the door in my tight mini and stiletto heels, my heart was racing faster with each step. When I got to the door John was waiting and quickly let me in. We sat in the back and he offered me a drink. I noticed he couldn't stop staring at my thighs. After some small talk and a few drinks,...

Teenage CD Awakening Part II

I had crossed the Rubicon. I had tried on my sister's panties for the first time. Now I felt guilty. Incredibly guilty, and dirty. I went to school as normal the next day, but despite the guilt I couldn't get the amazing thrill of trying on that little pair of blue and white striped cotton panties out of my head. As 3.30pm and with it the school bell neared, the overwhelming urge to do it again overcame my guilt. I was ready and willing to try on my sister's panties once more, as soon as...

Mischa s First Time With a Man

I have been cross dressing for a very long time, but it wasn't until recently that I decided to go full time girl. I have very feminine features and learned to embrace them over time. I always wanted to be the live-in 'girlfriend' of an older daddy-type of man, who would let me please him all the time. The thought of being a man's personal companion and sex toy is extremely gratifying. There's no better feeling than waiting for your Daddy to come home from work, grabbing him a drink and sucking...

I am Sissy

The year was 1888. My name was Sebastian but I was now called Sissy since I was taken a slave. My father’s merchant ship was captured and sunk by the pirate crew of the Black Bess. I alone was saved for Captain Booth's pleasure. He was an escaped convict from the prison island of Australia. He was a huge beast of a black man, dark ebony skin stretched tight over enormous muscles that bulged everywhere. He towered over every other man I have ever seen and he was not a kind man at any time. He...

The Making of Kairi Fox

The taller man of the two moved behind me. He carressed my cheek with a calloused hand, sending shivers shooting up my spine. His rough hands grabbed at my ass, pulling apart my cheeks and exposing my hole. I quivered a little in my restraints and moaned. I couldn't believe it - I was about to lose my virginity. Part 1For a guy, I wouldn't say I was bad looking. I had a slender athletic frame, often swaying more towards the former of the two. My hair was a dark brown, and I'd grown it out...

Jaime s Way Part 3

As Jeff closed the door he grabbed me by the hand and spun me around, pulling my nude body close to his, breathing in my perfume before locking his lips over mine. My fingers found the button on his jeans and opened them with urgency, more than a little pleased when his huge cock sprung out. “Damn, I want you so badly, Jaime,” Jeff moaned when he broke the kiss. “I'm yours to do with as you please,” I answered and wondered where THAT cheesy line had had come from. Pulling his jeans and shorts...

What a Girl Wants

"Come on, Katie. Give in to your desires. You've gone this far. You're almost there. You're so close to your goals and dreams of being treated like a lady. Accept it. Embrace it. Give in and complete your journey. Tell me what you want." Todd and I had been friends for years and even co-workers at one point in our respective careers. It had been almost ten years since I'd seen him and it seemed like fate that after all that time, I ran into him the first night I finally gathered the courage to...

48 Hours Chapter 1

Chapter 1: Sexual EqualityIt was Saturday morning, they were both lying in bed awake and the tension was almost suffocating. At last, Chris had the courage to speak."Look, I'm sorry, but I just can't switch on like a computer at least not right now, I need something to get me going. I do love you, but all this stress with my job just makes it really hard for me.""Or not hard!" came the barbed reply from Lynn."Well, that's helpful... It is pretty frustrating for me, you know! All I'm saying is I...

A Panty Boy in Paradise Part One

I wasn't sure how it was going to go. My new client hadn't given me any specifics. But I was excited about the glamour of being on a yacht with a rich older man and his young crew. We would be sailing for the weekend to the Bahamas and I would have my own cabin to sleep in and take naps during the day. All expenses, including the lingerie and bikini bathing suits I would wear, were paid for.When I arrived at the dock to go on board, I was greeted by three handsome young men who all were very...

The Bodysuit

“The process is actually very simple Mr. Smith,” she said.“It is very much like 3D printing, just using different materials and in a printer that prints on your body. We can print anything on top of your body to make you look however you want. The technology was originally developed for use in movie special effects, but we have seen there are, well, more personal uses that some of our clients like to use the service for.”How could I pass on this I thought. The chance to have a body in effect...

Pam s First Time

Just a few days of spring break left and I was planning on making the most of it. Well, the most for me anyway. I'm a crossdresser and I have been for a long time. All through high school I'd secretly dressed, slowly building a wardrobe of pretty panties, a few skirts and blouses, bras, my silicon boobies, and most importantly, my shoes. The most important thing I had going for me, at least from my point of view, was my stature, which was slight, no, it was petite. I have one year of college...

Andrew to Andrea Part 3

BRRRRIIIIIIINNNGGGGGGGGGG!!!!!!The alarm clock that my wife and I mockingly referred to as “Baby Ben” sounded off and pulled me from what I first thought was a great dream. As my senses slowly came online, I could feel my hand laid over my naked wife’s breasts and that I wasn’t in my usual gym shorts and t-shirt. I was surrounded in silk, and it was not unpleasant, but it was a floor length nightgown! The events of the previous night slowly began to trickle back into focus, and the...

Prom Night

When I was in high school, I was seventeen-years-old and dating an older man. He was forty-years-old and very handsome. He had taken me out to dinner and for ice cream and for walks on the beach. We had held hands and kissed but had never gone any further, but I knew he wanted to go further by the way he looked at me when we were riding in his car. I would see him looking down at my sexy, smooth tan legs and I would know, instinctively, he wanted what I had between them. Darryl had already been...

Happy to be Used Pt 6

Sir now knew I was his slut and would question nothing he told me to do. Though I presume this excited him, there is no way it excited him as much as it excited me.I was distracted every waking minute thinking about past experiences and future erotic scenes to come. I spent hours day dreaming and was masturbating at least four times a day. Every time I masturbated I shoved something up my ass.I worked endlessly on improving my feminine image. I spent all my time in feminine clothing at home...

It s Just Dinner My Sissy Transformation

I bet you're wondering how I got here. It was only six months ago that I was your normal American guy living every bit of his bachelor life to the fullest. Good job, good friends, good looking...not a worry in the world. But now here I am, standing in front of a mirror wearing a wedding dress trying to figure a way out of this. Nope, that wasn't a typo. I said wedding dress. Hmm, my body is better suited for mermaid style over ballroom. Ugh, see that's the stupid shit that I’ve been saying for...

The Sexy Ball Girl

When I was twenty years old and going to college, I had a steady boyfriend who treated me just like a girlfriend at all times. He opened car doors for me and he always paid when we went on dates. He was very sweet to me, making me feel feminine like a girl. He also liked having lots of sex with me in public places like the beach and parks and movie theaters, so we had an exciting, fun and romantic relationship. Ricky was a hottie with dark hair, dark eyes and a nice body. He had been a...

First Time For Everything

I have been crossdressing since my mid-teens, from sneaking a pair of my sister's knickers to sneaking into the gardens of my parents' neighbors and pinching underwear from washing lines. In my late teens, when I found girls and sex, I purged any clothing that I had and managed to put the ’urge’ behind me. I settled down and got married.Unfortunately for me (or not?), my wife liked to wear very sexy underwear, stockings, and very revealing outfits. This meant there were a lot of these ‘things’...

Working It

I’ve needed some repairs and painting done in a bedroom for a long time and decided to get some estimates. I had a water leak in the ceiling, and there was a hole there since it was fixed a month ago. Several professional painters came in and they all wanted $700 or more to do the job. I decided to ask my friends if they knew someone who might do it for less. One of my friends told me about Jim, a young guy going to college, who also has a painting business on the side. She told me that he...

Sexy Stewardess on a Hot Flight Part One

After arriving in Los Angeles, I became a tranny call boy to support myself. Working for an agency, I was sent to perform sex on many older rich men. Being a hot twenty year-old tranny slut with fresh meat in my panties, I instantly became one of the more popular call boys in the agency. Some men even took me out on dates for dinner then back their places or motel rooms for lots of sexy blow jobs and good fucking. I loved my work. I was especially satisfied by a handsome stud pilot who flew me...

Wife Gets Even Chapter 2

Amy said, “So I think you are going to need to take next week off from work. I guess you could go to work with your new look if you want to but I am doubting you will want to subject yourself to the ridicule and questions about your look. You should get some sleep so you are ready to go in the morning. Have coffee made by seven and make sure you shave your face and body again.”I simply nodded my head in agreement and said, “Okay.”I was up at sunrise and made sure I brought coffee to Amy by...

The Maid s Morning Part 2

So Ian sat there enjoying another cup of coffee and smoking a cigarette. He didn't do the dishes or vacuum the carpets. The minor dust on the hardwood furniture remained untouched and he intended to leave everything as it was. His mistress had threatened him with punishment and he looked forward to it.Way back when he had left home and moved into his apartment he had accidentally discovered that he liked to be disciplined. This occurred while he was living at home and had just finished...

Night at the Video Store Part 2

There were some strong, black street toughs in the SUV, but they got quiet when they saw me step off the curb into the parking lot. My nipples began to get hard under my little black micro mini dress and I could tell they were looking at them. I must admit, my platinum blonde wig, a huge Vegas style wig that went down my back to my butt, swung right and left as I moved my head back and forth looking at them.My make-up was perfect. I spent almost two hours on it before I left home, and my...

First Encounter Ch 7 Conclusion

I approach the bed cautiously. I can tell you still want me and I definitely desire you. How can that be so? You're not en femme, but still, I am transfixed by your waving appendage. I take my place at your side and our lips meet in an old familiar embrace. We kiss long and passionately. "Wow! I exclaim," I've never kissed a man before," I pant. "Of course you have, silly, you've been kissing one all weekend," is your breathless reply. My mind races to make sense of the situation. You are still...

Jenny Mike A Day out

I woke up in the morning with Michelle’s arm around me. We were spooning. She was the big spoon. I held on-to her arm stroking it gently as I recalled how ‘Mike’ and I had gotten it on in the living room the previous night. ‘Mike’ had fucked me on numerous occasions in the past, but my ass was still sore after what we had gotten up-to last night! God it was so hot! I turned my head to look at the clock on the night-stand and saw that it was 9:30 a.m. I slowly lifted Michelle’s arm from around...

Jessie and Sue

I felt like my life was spiraling out of control. It all started that one fateful weekend when my secret love of cross dressing was discovered by my coworker Dan. He knew he had me, and he had his way with me. Then came the next weekend when Dan invited me to his house only to have himself, Aaron, and Zach take turns with their sissy slave. And now last night, I was humiliated because of my performance with Tracy while being pegged by Karen and Sue. I was a wreck and it was the first day that I...

A weekend with Nancy part 3

Upon arriving back at the car Nancy said that we had to hurry to our next destination because it would be closing soon and then she instructed me to drive while Alice and herself got in the backseat. "Honey, do you know that porn shop up the road a couple of miles?" said Nancy. I nodded that yes I did and I was instructed to drive there quickly. At the porn shop, Nancy suggested that I fix my makeup and then she told me that I could remove my leash and put it in my purse because I would be...

Bookstore Crossdressing

It was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out. The hallway was empty where the booths were so I ducked into the booth that had a video of a luscious...

Tina and Me Part 2

We kissed deeply, my tongue twining around Tina's, as our nylon-clad bodies gently rubbed against each other. My dick was rock hard, pressing thru my tight panties, dripping with pre-cum, leaving a faint trail on her nightgown.I also realized I had to pee. Badly."Say, uh, I have to go take care of something," I said. "I gotta pee.""No fair!" she said with a playful pout. "I have to go too!"Really? Was this going to come out now, too?Tina had, for as long as I'd known her, used an odd turn of...

Minding the House

My neighbours Tom and Paula were going away on vacation and they asked me to keep an eye on the house for them. I gladly accepted as I wanted to see what their house was like on the inside but my curiosity really lay in exploring Paula's underwear collection. Paula was a 34 year old pretty mom of two kids, 5ft 7 with blue eyes and shoulder length brown hair. She possessed a slim but athletic body, pert tits and a nice rounded bottom. I let myself into their house the day after they left for...

GAG A RIFIC BARRY part 2

After leaving Barry out in front of my apartment complex for 5 minutes, Jenna and I went to check on him. Actually, we went to laugh at him. What we saw was Barry trying to hop (handcuffed and anklecuffed) towards some bushes for cover. If you remember, Barry was wearing only a pink thong panty. We watched through the glass in the apartment stairwell and laughed until we cried. Barry hopped towards some trees as a car approached him. Barry quickly jumped into the bushes and straight into...

Put it on

I was living and working in London, my first job after college. No chance of having a place of my own with these crazy house prices and this being my first job at the age of 23, so I rented a room from a guy older than me, in his mid-30s. His name was Steve and he was a masculine type, split up from his wife but seeing a feisty Spanish woman called Manuela. There were big arguments now and again but at least the sex sounded good, if the rather loud sighs, moans, groans and shrieking I could...

While the Cats are Away

Thursday night, mom is going to visit relatives out of town; dad is away on a business trip and not supposed to be back until Saturday. It took a lot of convincing that being sixteen is old enough to be able to stay home by myself and not have to go with mom to visit relatives. Dad was going to be home in two days and I would be going with him to the family ranch. Finally my mom relented and made me promise to be careful and stay out of trouble.After waiting for an extremely long fifteen...

In An Alley

It's a lonely fall night,I'm walking down a fairly empty street in town. Not the best part of town,but it's my only way to get home. I am in my grey business suit. Grey jacket,grey knee length skirt,black blouse,black pantyhose,black panties and bra,brunette wig and black heels. As I walk, the people that are out,glance my way,checking me out as I go through their neighborhood. Run down row houses,old abandoned buildings,adult bookstores on almost every corner. It's pretty seedy. As I approach...

Wife Gets Even Chapter 1

My wife and I get together with our neighbors to play cards to play cards about once a month. We generally have a good time but there are no stakes involved. For a poker player like me who is accustomed to gambling for large amounts of money playing just for fun is a little, well… boring. One night about a month ago, I tried to make the game a little interesting by including some drinking. We started the night playing pitch, with the loser required to drink a shot of Jack Daniels.With the...

Number Off A Bathroom Wall

Back in highschool I got a job working at the local mall at the Sears store. I was a stockboy and all around general gopher. I would always wear sexy outfits under my work clothes. On my second day I was asked to clean the bathrooms and I did. I started in the womens room,kind of hoping I would stumble onto a pair of panties or something,but no luck. I then work my way over to the mens room and as I clean and make my way to the stalls I open the first door and see writing on the wall,the...

Telling Mom I m 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...

Pure Innocence

It was an unseasonably warm Saturday and I decided to go out for a walk and clear my head. Instead of my normal guy garb, I decided to go out dressed as Aimee. But I was looking for a different look—totally cute and innocent which was not like me at all. I put on a little blue cotton dress, a pair of sandals, and donned a blond wig. The wig was long enough that I could put pigtails on either side. Even the light blue cotton panties I was wearing gave me the feeling of a young innocent female,...

A Terrific Threesome Part Three

Before I met Sherry, she had been having affairs with other girls. That was why she had a strap-on dildo to wear. She told me about the sex parties she would have with three or four lesbians that would last all weekend long. The girls would all get together on a Friday night and drink some wine and get naked and have all-female orgies for the entire weekend. Sherry had licked a lot of girl's pussies before, so she was open to me sucking men's cocks and still being her boyfriend. When she met...

A Little Naughty Fun When My Wife Is Away

When I was in high school, I always loved to dress in women’s clothes. The problem is I'm a guy. Whenever my mother was out, I'd always go into her room and try on her intimate apparel. I just loved how it felt on my skin. I'd especially liked how her bras and panties felt. I loved to get dressed in her dresses and even apply make-up. I really never told anybody about this. The lacier the better. I especially liked satin panties. They always felt real nice pressed against my cock. Fast...

A Close Encounter Part 1

A few weeks ago my wife remarked on how "the gals" hadn't had a night out in months and suggested that we should perhaps go out later that evening."What! Yeah, sure! What's brought that on?" It wasn't like Judy hadn't been around, on the contrary, she'd been around twice last week.I'm one of those cross-dressers whose wife gladly shares her wardrobe. And Samantha's the kind of wife that guys with my quirky habit can only dream of. We've been out together as a couple of girls on countless...

Seeking a Greater Perfection

I was on personal display for him. He would have me walk sensually while emulating the grace of a pretty blonde haired runway model. In my role of girlish temptress, I wiggle my sexy bottom in my exotic, six inch pink, high heeled, platform sandals. My body is slim, lithe, feminine and smooth.At the far end of his large living room he has me turn around, smile, and pose like a show girl for him. My exaggerated wink brings a genuine and enthusiastic smile to my bright red, pouty lips. As I...

First Encounter Ch 4

I awaken several hours later. The afternoon sun is slanting through the window illuminating your slumbering body. My head is beginning to clear from the effects of the Scotch and I slip silently into the bathroom to freshen up. When I return, you roll over and groggily say, "Is that you, Monique? You are wonderful."I kiss you lightly on the lips and say, "Yes, it's me and the pleasure was all mine."It's late in the afternoon and I suggest we get cleaned up and go for a bite to eat. "Will we go...

Telling Mom I m A Crossdresser Part 5 Movie Night and Gangbangs

I had decided to take a few days off from being Missy after Stan and Roger had left and my mom and I were finished with our little girl time. I spent the next few days just continuing with life as normal except for the throbbing pain in my asshole and my cock from the 3 days of constant sex. I couldn’t stop thinking about all the things I had done as Missy and all the kinky fetishes I had experienced since I came out to my mother, but I guess I have her to thank for all my new wonderful clothes...

Friday Night Maid 1

Friday Night Maid - By: Diane Leonard I am a Friday night maid. After a week of hard work, I relax by dressing up in a sexy maids outfit and serving, pleasing and pleasuring my wife. While she is out dancing with her friends, I am dressed up as a Friday uniform waiting for my wife to return home. She doesn't like my fetish, but this agreement, once a week seems to work for us. But this last week was to be totally different. It started out like any other Friday night session. I got home from...

Ladies Night at the Leather Bar Part 1

Chloe McGill never led me astray. I was a fulltime, tax paying citizen of Astrayville long before I met her - I just wasn't that good at it. Then Chloe came along, and that girl has ended up getting me into some of the most outrageous adventures. I adore her. It must be made clear how much more she is than just a cohort in gangbangs and sexual trysts of all sorts and sizes. She is the most influential person in my life after my parents. She found me as an insecure fledgling bisexual...

An Unforgettable Halloween

This past Halloween I took advantage of a chance to attend a charity Halloween ball. I had to travel for business to a city in upstate New York for a few days, and my first day there I saw an advertisement for an annual Halloween costume ball taking place in the mansion of local philanthropist. The annual party raises a significant amount of money for a designated charitable foundation. This year all proceeds were designated to go to Hospice. The cause itself was good enough reason for me to...

My New Life As A TGurl Slut Pt 2 2 Men My Girlfriend Me

It was only two weeks earlier that I'd met Lucy and the girls but what a fortnight it'd been.I was having the time of my life being girly and feminised so much of the time, being given an endless supply of gorgeous new lingerie, clothes, shoes, boots, and costumes to try on and wear - on top of my own already extensive slutty wardrobe. All the girls took turns doing my hair and makeup and trying different looks, colours, and styles. I was learning fast and loved spending whole weekends as a...

The Photographer And The Sissy

I was 2twenty-two, closeted fully and living out my sex life in fantasy and on the internet. I had discovered my love of dicks in my teens, followed a few years later by my fetish for dressing up like a girl. I have no idea why, but the sight of my own body in tights, knickers, stockings and heels made my boy pussy (dick) wetter (harder) than anything else, straight or gay.Luckily, I lived alone (in a private studio apartment, in a major city in the Netherlands), so I could basically live out...

Car Park No 1

The Car Park No 1 The car park has always been a great place for meeting a fellow for a good time. I had been there several times over the years and felt a great satisfaction in satisfying the needs of a horny participant.It has become more of a challenge since the police seem to patrol it more often than in past years. However, I had the opportunity to have a few hours to my self as my wife was out. I decided to look in to any prospects at the park.I drove in and parked to view all in coming...

The Day My Secret Was Discovered

My wife and I have been happily married for four years. She is the dominant one in this marriage. Just recently I have discovered how much I enjoy wearing women's clothes. I love how the panties feel between my ass cheeks. The silkiness of the nylons on my legs as I slide them causes an erection every time. My wife had no idea until one day when I had Friday off from work. As soon as she left for work, I went to our bedroom. There, I quickly stripped off my t-shirt and shorts. Glancing at the...

My First Real Outfit

My First Real Outfit I started completely dressing in women’s clothes shortly after high school. I didn’t really own anything of my own but I would fully dress in my mothers clothes a few times when I knew she would be gone for a few hours.. Usually it was just pantyhose, bras, and panties that I would borrow from my mom . I had experimented with it a bit when younger, stealing my mom’s pantyhose and jerking myself to incredible orgasms while wearing them or being forced to wear them from a...

My New Boyfriend

I recently moved to a new town and joined a gym. It's not one of those fancy gyms with weight machines, a latte bar, and women in spandex running around trying to be noticed by men. It's a sweaty men's gym with barbells and dumbbells that require men to double up and spot for each other. The first day I was there, Jack "Kell" Kellson, a solid built six-foot-three-inch muscle boy my age, came over and spotted for me, right away. Since he seemed to like spotting for me, we developed a friendship....

Aunty s New Girl

This is the continuation of Tickets Please! Shakily, I keyed in the URL from Trixie's card, my mind in turmoil, heart racing as her sweet gift seeped from my aching pussy and soaked into the lacy panties I was wearing. I was wedged behind one of the 'tables' thoughtfully supplied for the busy passenger. You know the ones, if you move a fraction either way you end up concussing your neighbour, or at the very least, be greeted with the very English insult of a shake of the morning paper and a...

Shopping with the Boss s Daughter

I came home from work after a successful morning meeting where we finalized a big project. I decided to celebrate by going out to buy a new dress. I changed out of my business suit and grabbed a quick shower to shave smooth. I put on my make-up, choosing to go with a conservative look for the day with a pink lipstick. I got dressed with black panties and bra, and pulled on the silky nylons and attached them to my black lacy garter belt. I then slipped into a long navy skirt with matching blazer...

His Dirty Little Secret

Julia was doing some spring cleaning in the house. She had scrubbed everything, cleaned the oven, scrubbed the floors and was in the process of cleaning out the closets. Stuffed in the back of a closet was a bin. She didn’t know what was in it. The sight that greeted her caused a jumble of emotions in her. The bin was full of women’s clothing. It was all silky and sexy; Nightgowns, little panties and thongs, silk scarves and some thigh highs. But none of it was in her size. It was all too large...

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