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First Time a Cross Dresser Gets Laid Pt 1

Mark was a shy guy who had always found it difficult chatting up girls. There was always some reason. He didn’t like their hair, or their body, or their look, or their personality, or his family would not approve. His upbringing was very conservative, old fashioned and his stoically minded, overbearing, controlling parents, forced their ideology on him. This had left its mark on him and he was a nervous, timid person. Any idea of an alternative life style was just not something he could do or...

First Time

Aunt Convinced me for a cross dresser romance session Free Sex Stories and Adult Erotica Stories

Hi, my name is Sam and I am a 26-year-old, slim physic cross dresser. I am a fashion designer and have a thing for female clothing. Not only I love designing female clothes but I also enjoy dressing as a girl. Coming to my story, this incident took place some years back when I was around 20 years old and had cross dresser romance session with my real Aunt. With fair and curvy physic, I can look more girly than a girl with my cross dressed attire. On one weekend, I went to my aunt’s place...

Cross Dresser

Confessions of a Sex Crazy Cross Dresser

The Confessions of a Sex-Crazy Cross Dresser Book I: The incredible first few weeksChapter 1: Panties Thief and the Late Night Swim My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used to describe people like me can make you confused. I prefer to be called a cross dresser and yes you can call me...

Crossdressing

Confessions of a Sex Crazy Cross Dresser Part 4

Hi Everyone, I hope you like these chapters, please let me know if you want the next two. Chapter 7: Triangle of Fun I slept great that night with a full stomach of drink, food and Peter’s cum. I woke up on Friday and thought this is going to be a hell of a weekend. I played around with my cameras and had finally figured out how to use the self timer on the 35mm and how to use all the options on my movie camera. They were both relatively new as I bought them in Phoenix, just before moving...

Confessions of a Sex Crazy Cross Dresser Part 4

Hi Everyone, I hope you like these chapters, please let me know if you want the next two. Chapter 7: Triangle of Fun I slept great that night with a full stomach of drink, food and Peter’s cum. I woke up on Friday and thought this is going to be a hell of a weekend. I played around with my cameras and had finally figured out how to use the self timer on the 35mm and how to use all the options on my movie camera. They were both relatively new as I bought them in Phoenix, just before moving back...

Crossdressing

Confessions of a Sex Crazy Cross Dresser

The Confessions of a Sex-Crazy Cross Dresser Book I: The incredible first few weeks Chapter 1: Panties Thief and the Late Night Swim My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used to describe people like me can make you confused. I prefer to be called a cross dresser and yes you can call me...

A Cross Dresser s tale

You may think of me as Fiona, and I am a cross-dresser.A story by Erica inspired me to pen my saga of cross-dressing. I am also a recovering alcoholic, with a few days over 19 years without a drink as I write this, and I suppose the two tales are intertwined to some extent. Not that I am a saint by any means, a lot of people with a lot less time have a better sobriety than I. But I learned that alcohol is a poison to me, so I avoid it. I just do irrational things when I add alcohol to my...

Confessions of a Sex Crazy Cross Dresser Part 8

Chapter 15: Dangerous Duo I woke up the following morning to an empty bed. I went to the bathroom and when I came out there was a knock on the door. I looked out and saw Peggy with a bag and two cups in her hands. Upon opening the door, Peggy came inside and placed the drinks and bag on the table and gave me a kiss. “I thought you might want some breakfast,” she said. She had on a pair of white shorts, a light blue tank top and her sneakers. “I brought coffee and donuts.” This girl might be a...

Crossdressing

Confessions of a Sex Crazy Cross Dresser Part 10

Only 1 chapter left after this installment....I hope you are still enjoying Sandy's adventures Chapter 19: Last Day in Vegas The next morning Tanya left for her house after exchanging numbers with us and promising to visit Peggy in Phoenix next month. The hotel had arranged a car to take Peggy to the airport for her 9:00 flight. I was sad to see them go, but at the same time, I knew I had work to do and I wanted to have some time to myself. I had to go to two accounts and I finished by noon....

Crossdressing

Confessions of a Sex Crazy Cross Dresser Part 2

Chapter 3: New York with Linda I didn’t really get a lot of time to think about what I had just done with Carlos. I fell asleep shortly after he left due to all the drinks I put away during the night. I actually fell asleep on my couch, still full dressed except for my jacket and shoes. When I woke up, I had a headache and was starving; I never even had a piece of the pizza Carlos brought. It was 2:00 in the morning and I was scared to look in the mirror.I took a shower to clean off the make up...

Crossdressing

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...

Gay Experience With a Stranger Cross dresser Sex 2 Free Sex Stories and Adult Erotica Stories

This is the second part of my previous story. I will write about how I had rough Cross dresser Sex with him. Please continue to read the story, I know it’s a bit long story but I wanted to put in all details of my Gay experience. Ok, let’s move on to the story. We reached his place by a Cab. As we entered, he locked the door and grabbed me by surprise and pulled me closer. He planted his lips on mine, and I gave in too as we kissed deeply. He parted lips and walked me to his...

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Alison Goes to London chapter 11 A Dirty Filthy Motherfucking Assfucking Whore

Dear friends, let us love one another, for love comes from God. Everyone who loves has been born of God and knows God. Whoever does not love does not know God, because God is love. This is love: not that we loved God, but that he loved us and sent his Son as an atoning sacrifice for our sins. Dear friends, since God so loved us, we also ought to love one another. No one has ever seen God; but if we love one another, God lives in us and his love is made complete in us.It was Saturday morning,...

Incest

Confessions of a Sex Crazy Cross Dresser Part 6

Here are the next two chapters of Sandy’s adventures Chapter 11: Photo Shoot and the Elevator Ride I slept great on Monday night after my craziest night of cross dressing. My body felt great as I slept in late. However, I had to admit, I felt like my ass had been torn up from Stan’s incredible cock. I realized now that almost all men wanted to get their rocks off with strangers. Stan and Bob were perfect examples, they wanted to fuck a girl or at least get a blow job. They were so happy they...

Confessions of a Sex Crazy Cross Dresser Part 6

Here are the next two chapters of Sandy's adventures Chapter 11: Photo Shoot and the Elevator Ride I slept great on Monday night after my craziest night of cross dressing. My body felt great as I slept in late. However, I had to admit, I felt like my ass had been torn up from Stan’s incredible cock. I realized now that almost all men wanted to get their rocks off with strangers. Stan and Bob were perfect examples, they wanted to fuck a girl or at least get a blow job. They were so happy they...

Crossdressing

Young Cross Dressers Secrets

Young Cross Dressers Secrets *Sandy was busting at the seams to tell someone some very exciting secrets she was keeping. She couldnt tell anyone she knows. She decided to tell them here. __After reading My Bra and Panties are Missing, my own real story kept nagging at me to be told, but I wasnt sure how. I decided to change all the names and write a story all about this secret world I stumbled into. I started getting very horny just thinking about all that had happened&hellip,. __My story...

How Hockey predisposed me to be a Cross Dresser

I had a thought the other day, my hockey equipment has a number of striking similarities to lingerie!To set the stage, I am a cross dresser. Like most of us, I love everything about ladies undergarments. I like seeing lingerie in stores, on models, on women, on men and of course on me! I love the feel when I am dressed up. I love the taboo of wearing them. I love the thrill of being "underdressed", that is wearing lots of lingerie under your manly clothes, when I go to work. I especially...

My first time going out as a Cross Dresser

MY FIRST TIME OUT AS A CROSS DRESSER A true storyIt was 14 years ago and I had been married to a beautiful petite woman she had long Cole black shiny hair with green eyes.. We had been married about a year and one night I came out playing around in a pair of her sexy blue panties and a sexy blue Teddy and started rubbing on her and having fun it made her so hot we both had the best sex we ever had in our lives.. The next Friday when I got home there was a bag on the table she told me to open...

Auto Ride Made Me A Cross Dresser Whore 8211 Part 1

I’m a male, and cross-dresses occasionally in private. After cross dressing I get hard and then get off rubbing my dick against bed. Sometimes I post my cross-dressing photos online and get excited by comments and chats. I fantasizes about being seduced/forced to cross-dress and made to serve like a whore by dominant stranger(s). I’m darkish brown, lean. Has little hair on my upper body. Thin. Have slender arms. Soft face. And thick lips. And finger thick but long. My butt is rather fine and...

Gay Male

My First Time with a cross dresser

Growing up, like many children I went through phases. I would climb trees and play football, then as I reached my mid-teens I continued these phases but also became a lot more sexually aware, thanks to the porn magazines and porn films usually belonging to my mates dads or older brothers.Now I am in my late teens and at college.One day my Dad made a pot of tea and breakfast.“Did you sleep well, son?” he asked as I entered the kitchen.“Not bad thanks, Dad, how about you?” I replied.“Pretty good...

Crossdressing

The Cross Dresser and The Big Fat Fuck

As soon as the door closed to her place Debbie started squeezing me tight. Before I knew it I was the one with my dress around my ankles. Soon I was being pulled down the hall to Debbie’s bedroom. While I sat on her bed, Debbie went in her bathroom to freshen up. When she came out she was wearing a sexy red night gown. If it weren’t for the fact it was a size 6X you might have thought Debbie bought the thing at Victoria’s Secret. ...

The Cross Dresser and The Big Fat Fuck

As soon as the door closed to her place Debbie started squeezing me tight. Before I knew it I was the one with my dress around my ankles. Soon I was being pulled down the hall to Debbie's bedroom. While I sat on her bed, Debbie went in her bathroom to freshen up. When she came out she was wearing a sexy red night gown. If it weren't for the fact it was a size 6X you might have thought Debbie bought the thing at Victoria's Secret. ...

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...

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...

Crossdressing

Confessions of a Sex Crazy Cross Dresser Part 11

Hi All, it required a couple of re-writes to make it better. The final chapter of Sandy’s adventures in book 1. Please let me know if I should publish book 2 Chapter 21: Nikki’s Night and Sandy ’s Night to Remember I finished shaving Nikki spending a lot of time shaving her pubic hair. I made a small heart shape right above her clit and took off all the rest of her hair. When I finished shaving my new love muffin, I took a shower. When I was dry we got dressed together after a couple more...

Cross Dresser 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...

Confessions of a Sex Crazy Cross Dresser Part 11

Hi All, it required a couple of re-writes to make it better. The final chapter of Sandy's adventures in book 1. Please let me know if I should publish book 2 Chapter 21: Nikki’s Night and Sandy ’s Night to Remember I finished shaving Nikki spending a lot of time shaving her pubic hair. I made a small heart shape right above her clit and took off all the rest of her hair. When I finished shaving my new love muffin, I took a shower. When I was dry we got dressed together after a couple more...

Crossdressing

Auto Ride Made Me A Cross Dresser Whore 8211 Part 4

Thanks for the nice feedback I received for this series about a cross dresser. If not for them, I might have discontinued this as I was making progress at an agonizingly slow pace. Apologies for the delay in the update. I am sending the next part, so for the first time, I sending two parts together. I also have some plans for another 2-3 parts of Rakhi’s journey and her slow conversion into a whore. I will start right from where we left off. Please read part three and parts before that to find...

Gay Male

Young secret cross dresser 8217 s 1st experience

Hello everyone. I am Anuradha / Sameera, a Secret Crossdresser of 29 years old from Telangana. My breast might be around 34-36 as 36 size too fits well. I love sports bras and padded bras. started in my junior college days when my friend became my boyfriend. It started with him sitting beside me. We used to stroke each other’s cocks secretly under the bench. The handjobs slowly turned into blowjobs. I also had my boobs squeezed by a few others in the class. But I was too scared to tell my...

Confessions of a Cross dresser June 29 1982

It is 8:35 on a warm summer morning. I hear the front door close and already the excitement is building. I hear the car start and then pull out of the drive way. I run to the front of the house and watch my mother pull up the hill and off to work. My sister left for work 5 minutes ago and Dad is gone until 2PM.I turn and walk up the green carpeted stairs. With each step I feel my heart pounding harder and harder. As I reach the top of the stairs I take one last look out the window to make...

Bi Cross dresser that s me part 2

A week later Chris and I met to go cloths shopping. We met at a coffee shop in a town a hour drive from me. She greeted me with a warm hug followed by a deep kiss. Our obvious age difference drew some judgmental stares from a lot of the other patrons. Chris sensed the fact that I was uncomfortable. She whispered in my ear "If only they knew all of the cum I licked from your ass". We grabbed two coffees to go and headed out."So Eric said I needed to get something kinky to wear the...

Fun with a cross dresser

I had a really good experience with a cross dresser yesterday. A mutual friend had recommended him after enjoying his services so I got in touch and he immediately responded by inviting me to go and meet him. It was most enjoyable. I have never been with a CD before but he seemed okay. He is late 50s and very slim. It was really quite strange. He came to the door in a dressing gown and invited me into the lounge where he explained how he had got involved in all of this by dressing up in his...

Step Mother s Sex Slave Cross dresser blackma

My heart pounds as I tip-toe across the soft, pink carpet in my parents' room. I'm home alone. My stepmother's lingerie collection awaits.A floorboard creaks as I make my way to the dresser. I'm facing my worst nightmare--getting caught playing with Ann's lacy undies. But I'm totally hooked on wrapping myself in her silk and lace. I decide to move forward. The risk adds to the adrenaline rush.I stretch out my fingers to grab the drawer's brass knobs. The sensual pleasures of cross-dressing are...

How I Became A Paid Cross Dresser

Hello friends, without making you feel bored directly coming to the story. It was the time when I was in need of money and I asked my friend Rahul. He told that he will help me and when I met him he told me that I have to work his boss. I asked what kind of work then Rahul said that his boss is a bisexual who prefers crossdressers more than gays. Me:- so what I should do for your boss Rahul:- don’t get me wrong, you said that you were in need money so am telling this. You need to get dressed...

Gay Male

Cross Dresser 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...

Gay Male

Cross Dresser 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...

Gay Male

Tea party for a cross dresser

I decided I'd walk over to her place. It wasn't far and it was a nice day. Once dressed I picked up the bag and headed out the door. I arrived just before 8. She answered the door in her dressing gown. "darling" she said and we kissed each other on both cheeks as I entered. I stood in the hall. The flat had high ceilings. We went to the kitchen. We discussed proceedings over tea and toast. Showers were a must. I had a lot of shaving to do. That would take some time. There was one...

The twin sisters of the cross dresser policewoman

（This post is a fictional story on a bondage forum in China, and I am the prototype of the story. I just translated it into English. The copyright belongs to the original author, and the portrait right of the photos in the original link belongs to the original author and me）In the middle of a gloomy and horrible room stood a woman with a shawl. She was wearing a sexy red cheongsam, a pair of sparkling flesh-colored stockings like cicada wings wrapped around the beautiful woman's slender legs....

A Cross Dresser s Revenge

CROSS DRESSERS REVENGE BY JANICE I was fifteen years old when I was beaten up and raped by three big adults. I was on my way home from Martial Arts school when it happened. I was pretty good, tops in my class, but that was little help to a teen age boy against three big drunks, aside from being beat up, I was also sexually assaulted. The three of them were arrested a few days later but not for what they did to me,...

Boy Made Cross Dresser

Hi, I am a male of 32 years, but I like to cross dress. I used to work as a techie in a company in Bangalore but my love for a cross dress made me leave it. My parents broke relation with me when they caught me with my bf in college days and from then I am living alone. They don’t know even that I am alive or dead. This is my story of why I left my job. I used to work in this it company in Bangalore and my team leader was an arrogant person. I never used to get along with him. I liked to cross...

Gay Male

An Incident in a Cross Dresser s Life Part 4

An Incident in a Cross Dresser's Life Part 4I always dressed in pantyhose while teaching class. I had on an extra tight pair of panties to hold in my butt plug. Every movement sent shivers across my nipples. The only person who knew was my fuck buddy and fellow teacher. She was the first to let me explore my cross-dressing (see previous stories). After school, we would go to the park in her van that had dark windows that no one could see in. She would sit back and I would eat her pussy until...

A Cross dresser 8217 s Fantasy

Hello everyone, I’m a regular reader of the site and figured that it’s about time that I write a story. Let me first say that the story is completely fictional. Let me first give you a description of myself. I’m really petite and have an average ass. I’m 21 years of age and weigh about 50kg. If my face and chest weren’t visible, one could easily mistake me for a girl of 18-20. I’ve a light brown complexion and a darker ass. And my cock is about 6 and a half inches. Going back a few years, I got...

Gay Male

Cross Dresser 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...

Crossdressing

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...

Bisexual

Topanga Lawrence Becomes Violet Vortex

TOPANGA LAWERENCE BECOMES THE VIOLET VORTEX Hi fans, I know most of you don?t know who the actress Danielle Fishel is but she is this hot actress who was on a terrible sitcom who grew up into a babe. I just had to put her in a story. You may be seeing another actress Monica Keena in tights [email protected] Ms American is Mr X creation but the rest is mine. If you are a minor stop reading this awful story filled with bondage, forced sex and other adult...

50 00 Bet Cross dresser

My friend Cristina and I were just sitting around watching porn. It's something we do for fun now and then. Believe it or not, it has never led to anything. A scene came on where a guy was put in a wig and satin nightgown and fucked by a beautiful blond dominatrix with a strap on. We laughed at what an ugly girl he made and somehow it came up that I had a girlish look to me. She said that I would look much more like a girl in the wig and nightgown than the guy from the movie. I just...

How I Became a Cross Dresser

For as long as I can remember, my sister dressed me in her clothes and makeup every chance she could find. She was two years older than me, so I didn't have much choice when I was very young. Up until I was about 12 or 13, my mother allowed this to go on, and by the time she said no more dressing me up, it was too late. My sister and I continued to dress me up in whatever we could find every time my mom left the house.When I was 15, she had a group of girls sleep over, and they called me into...

Telling Mom I m A Cross Dresser Part 19 Christmas Special

Christmas Special It was now around Christmas time and I couldn’t have been happier. Any other year we would have had family over which meant I had to dress normal because the other members of our family still had no idea or at least weren’t talking. However this year we had no plans at all, our cousins were off on vacation to Mexico until new years, my grandparents were not in a visiting mood because of some family matters that keep us from talking to each other at the moment and others we...

Incest

3 Teen Cross Dressers Misadventure Part 2

Here are 4 men all at least 6" taller than us with athletic builds; we really thought we were about to get our asses kicked and robbed. One man got up an opened my duffel bag and of course found all of my crossing clothes. "We have us a couple of fags don't we." He said, opening the other bags finding more of the same. We were silent until Sean said that we just do it to get a kick from people and that we weren't gay. They all stood up and one put the chain lock on the door. "You are tonight...

Incidents in a cross dressers life Part 3

How I wish I knew more about cross-dressing when I was young and attractive.I had an Auntie James who cross dressed with his friends but I was way too shy to ask about it. It was not until I was home on leave from the Marines that I had my first experience with dressing. I went to Rocky Horror Picture Show with James and his friends who were all dressed up. Some of them were very hot. We went to a coffee shop where all the Gays go after the bars close. A lot of Gurls where hitting on me. I have...

Teen Cross dressers First Man

This is a true story that happened to me only a few monthe ago. I just moved to a new town, I was an average 18yo male about 5'8 lean and athletic with a few female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought about how great it would be to hook up with a shemale. I never thought it would happen of course, I didn't know where that stuff happened and I was always really shy. One Friday after a grueling 4 hour study session...

Teen Cross dressers First Man

This is a true story that happened to me only a few monthe ago. I just moved to a new town, I was an average 18yo male about 5'8 lean and athletic with a few female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought about how great it would be to hook up with a shemale. I never thought it would happen of course, I didn't know where that stuff happened and I was always really shy. One Friday after a grueling 4 hour study session...

Confessions of a Sex Crazy Cross Dresser Part 2

Chapter 3: New York with Linda I didn’t really get a lot of time to think about what I had just done with Carlos. I fell asleep shortly after he left due to all the drinks I put away during the night. I actually fell asleep on my couch, still full dressed except for my jacket and shoes. When I woke up, I had a headache and was starving, I never even had a piece of the pizza Carlos brought. It was 2:00 in the morning and I was scared to look in the mirror. I took a shower to clean off the make...

my first time cross dresser

It all started when 13.when I on a chat room talking to this really nice guy and he sounded hot so I added him on msn. He went on cam and he was stunning he was clean shaven thoses jaw droping abs and huge 8 and half inch cock I woz dribbling just looking at him. I told him that I loved wearing girls cloths he love it too he told me he love young boys cross dressing so I got dressed up in my sister slutty outfit that was black lasce g string thong matching bra grater and fish net stocking...

From Cross Dresser To A Cheap Slut

Hi this is Vinnie Cd slut again with another hot adventure. I dress in panties all the time and I am addicted to thick hairy cock. I am 5’7 32 waists med built but curves which show when I dress up like a slut. I had a job interview which went on very long.After the interview it was very late and I was waiting to get an auto back home. Some autos came by but them Were charging too much. Is waited almost an hour and thought should maybe call a cab. I realized the battery Died and phone was...

Gay Male

Crossdressersa ed and Turned Out Ch 02

So, after I blew the guy downstairs and told him to come and knock on my door and pay me to blow him again anytime, I went up and took a long hot shower and put on a nighty and went to sleep. I slept surprisingly well considering I had just spent a long night out selling my ass. I thought about how much it scared me and aroused me as I drifted off to sleep. The next day I called Jesse and talked about what happened. We talked about how turned on I was by the whole thing she told me I was nuts....

The Crossdresser s Club

The Crossdresser's Club By Tammy Richards CHAPTER 1: THE DISCOVERY It was the Saturday before Christmas. Natalie was in the attic looking for boxes to wrap the last few presents, while John was running last-minute errands. As she dug through a pile of boxes in the corner, she happened to open a large box that had been pushed behind the rest. Imagine her surprise when she discovered that the box was full of women's clothes. There were dresses, lingerie, high heels, even a...

Crossdresser s Surprise

A Crossdresser' s Surprise - by: by Deborah Pinto I guess I should have seen it coming. My wife, Virginia, and I were drifting apart sexually, and I should have suspected that she was having an affair. Afterall, we had not made love in over a year except for one night she had come home a little drunk from her office Christmas party and had virtually raped me in the middle of the night. I remember her laughing and saying, "Tim, what's wrong with you tonight? You feel so tiny inside...

Crossdresser s Placement Agency

I know it's a little dated, but read it anyway. Crossdresser's Placement Agency By Ricky With apologies to those of you who weren't around to listen to radio in the sixties, I'll start this with a famous quote. In the immortal words of the Chicken Man: "They're everywhere, they're everywhere." Crossdressers, that is. In the last week everywhere I look I see a crossdresser, right out there in public. First there was the color coordinated Dennis Rodman with green hair and...

The Crossdresser s Quiz

The Crossdresser's Quiz By Ricky I have recently been educated. After all these years of simply wearing frilly clothes and thinking them feminine I have finally found out the secret of how to be a real woman. And all because my car is a clunker that just passed 100,000 miles... It happened this way. As soon as the odometer turned over, every time I got in the car something else major broke down. Within 3 weeks I replaced the rear main seal, the fuel injectors, water pump,...

Humor

A Crossdresser s Night in the Park

A Crossdresser's Night in the Park cd, bdsm, con, mm, anal, oral, toy 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...

Crossdresser s Paradise

Crossdresser's Paradise By RogerGirl Charles had just returned from his summer trip with Stan and Desiree. It was a rare time of year since both his parents were home at their main mansion. Charles was feeling nervous, but felt he had to finally tell his parents about Charlene, his feminine side, and that he was bisexual. He walked into the kitchen where his parents were eating lunch. His father, Simon, came from a long line of wealthy businessmen and had expanded his family's...

Crossdresser s Spanking Scene

My roommate and I were both bi and part-time cross-dressers. We were also familiar with consensual B & D and had already worked out several code words, then went a step further and wrote scenes for each other, so that when we're in the mood, we could call up the scene rather than try to explain it or coach someone through it. Sometimes we did a scene to please each other sometimes we asked for a scene because we were in a specific mood. So it was that I got an e-mail at work, which...

Crossdressing

Incidents in a cross dressers life Part Two A tr

My first "outing" was with a female fuck buddy. She loved sex. Any time, place, or person. Damn she was a great fuck buddy! She asked about any fantasies I had. I mentioned I always wanted to cross dress in pantyhose, panties, bra, and a great wig. We spent the afternoon shopping and found all of my needs and a great wig that matched my natural hair color. There is a nice pic of me labeled "first pic." in the gallery. My nipples and cock were rock hard the whole time, especially while she...

My first Cross Dresser and me

I laid down beside her and gave her the soda. We sipped slowly and talked about what had just happened. I sat the sodas on the night stand and moved up closer to Toni (a name we will use for this article) crossing my leg over hers so that my clitty rested on her nylons. We kissed for several minutes as I played with her nipples thru the silky bra. Toni looked up with lust in her eyes and said she wanted me to fuck her.I started kissing her neck and started down her soft body, I raised her bra...

Crossdressing

tied to the dresser with a blindfold

I had found the door to your place unlocked. Your instructions were to make myself at home, and so I decided to look around. When I approached the bedroom I heard some kind of noise and peeking inside I found you; Sitting on and tied to the dresser with a blindfold covering your eyes. Your breathing was heavy and irregular. I approached you, slowly, without noise. I wondered if you could tell someone was in the room with you. When I was next to you I gently reached out and touched your leg. You...

Reluctance

My First Time with a cross dresser

Growing up, like many children I went through phases. I would climb trees and play football, then as I reached my mid-teens I continued these phases but also became a lot more sexually aware, thanks to the porn magazines and porn films usually belonging to my mates dads or older brothers. Now I am in my late teens and at college. One day my Dad made a pot of tea and breakfast.“Did you sleep well, son?” he asked as I entered the kitchen. “Not bad thanks, Dad, how about you?” I replied. “Pretty...

Craig s List Cross Dresser

I find your address and knock on your door. You answer and let me in. I give you a peck on the cheek and give you a hug, with my hand on your lower back I pull you in and feel your body press against mine. I sit in a comfortable chair and ask for a glass of water. I watch your legs and ass as you walk away from me in your stockings and sort skirt. You return with the water and hand it to me. As I take it with my right hand, I put my left hand on the inside of your knee. You freeze and I rub...

Telling Mom Im A Cross Dresser part 18 Missys Halloween Party

I had enjoyed my week of sex with Thomas and Lemar but in the end it left me sore and used but not like I was complaining. It was now getting close to Halloween and mom and I were making plans to go to a Halloween party a few city blocks away from us. Yeah, sounds kind of boring I know but it was no ordinary party with costumes and drinking alone. It was an orgy for bisexual people. It was only a few days away and Mom and I decided to go costume shopping both online and in the local stores to...

Confessions of a Sex Crazy Cross Dresser Part 8

Chapter 15: Dangerous Duo I woke up the following morning to an empty bed. I went to the bathroom and when I came out there was a knock on the door. I looked out and saw Peggy with a bag and two cups in her hands. Upon opening the door, Peggy came inside and placed the drinks and bag on the table and gave me a kiss. “I thought you might want some breakfast,” she said. She had on a pair of white shorts, a light blue tank top and her sneakers. “I brought coffee and donuts.”

Confessions of a Sex Crazy Cross Dresser Part 5

I hope you enjoy Sandy’s continuing adventures. Please comment and let me know if I should include the next two chapters. Chapter 9: Joe’s Pizza Sunday morning I got up pretty early. I decided to call a cab and go over and pick up my van from Glenn and John’s. After I got back I decided to do some sit ups, as I had not been exercising as much lately. A quick shower after my exercises and then I decided to get ready for my trip. I spent a couple of hours packing as I was going to be gone...

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 more Chapter 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...

Confessions of a Sex Crazy Cross Dresser Part 10

Only 1 chapter left after this installment….I hope you are still enjoying Sandy’s adventures Chapter 19: Last Day in Vegas The next morning Tanya left for her house after exchanging numbers with us and promising to visit Peggy in Phoenix next month. The hotel had arranged a car to take Peggy to the airport for her 9:00 flight. I was sad to see them go, but at the same time, I knew I had work to do and I wanted to have some time to myself. I had to go to two accounts and I finished by noon. I...

Craig s List Cross Dresser Part 2

I turn you upside down so you back is on the chair with your legs over the back. I take off my pants and underwear. My dick is only half hard but I rub it into the cum on your face and feed it to you with the head of my dick. Then I rub my balls all over your face before leaving them for you to tongue and suck them into your mouth. I am getting harder now. I pull my scrotum up so you can tongue the sensitive area between my sack and my anus. As you lick this area, I reach forward and rub your...

Halloween cross dresser

This year for Halloween I planned to dress like a slutty secretary. I wanted everyone to be shocked it was me. It was to be my ultimate costume. Cause nobody would ever expect it. Nobody knows about my alone time. That I like to dress up and play with my boy hole! I set the plan in action months before. Watching makeup tutorials I mastered the seductive look. I worked on my voice and practiced walking in 6” stilettos. On the outside I’m a mans man. I have a long 3 year old beard, tattoos, I...

My life as a cross dresser 7TRUE STORY

About half hour went by another beer was given to me and MarkI was feeling a little tippsy , the conversation had been really exciting , John had been asking me questions about my sex with Mark and wearing knickers,He asked did I wear my sister's or mum's underwear , my shyness was disappearing with the beerBoth mine and marks cocks was still sticky and leaking, he told me to lick marks cock and balls clean,I knelt on the floor between marks legs his cock was soft , I held it to my face and...

My life as a cross dresser 6 John TRUE STORY

Mark told me he had a message for me he was going to John's house Saturday and I had been invitedMark told me a lot about John he had asked or rather ordered Mark to steal his mum's and sisters knickers And he had a suitcase full of women's clothing, He gave Mark drink , mainly beer and cigerrets and lots. Of porn magazines , John would suck him but he never had fucked him , he would rather watch but he liked mark dress as a school girl and almost alway cum in a pair of knickers,John would the...

My life as a cross dresser 5 introductionTRUE STO

Mark and I was having sex every opportunity we could get, we was borrowing our sisters and mothers underwear and dressing up whenever we could , Mark one day dared me to go running with my sister's her and knickers on under my running kit, although nervous in was excited so I agreed, i put on white cotton knicker and and a small cupped bra and we ran our usual route had a drink of lemonade before running back through the woods, we stopped half way he wispered keep quiet , there's people in a...

My life as a cross dresser 4 TRUE STORY

I kept the knickers for a number of years, as a trophy, I couldn't tell you how many times I used those knickers while masturbating, thinking back, over what I saw that night still makes me feel hornyMark sort of got things sorted out with Linda, our friendship got closer, we wanked or sucked each other off on a daily basis, either in the woods or in one of our house's, if no one else was home, Mark had told me he wasn't the only one John had at his home, and described in great detail what John...

My life as a cross dresser 3 TRUE STORY

Mark told me during the half term he had met John and went back to John's house a couple of days and looked at porn books drank beer smoked and watched a few blue films John had wanked and sucked him off and ever let Mark stick his cock in his bum and fuck him, my. Cock was stiff and leakingHe told me John liked him to dress as a girl and he had asked Mark to steal a pair of his mum's and sisters knickers for him Why I asked?Mark explained he had a suitcase full of bras knickers and tights...

My life as a cross dresser 2 TRUE STORY

The next couple of days felt strange, I had seen Mark and John nothing had been mentioned about what had happened , I was going to bed at night masturbating at the thoughts of what had happenedOn the Friday mark and I arranged to meet for training Saturday afternoon.I arrived at his house about one o'clock, in shorts and shirt he wasn't changed he invited me in to his bed room, he told me his parents and sister was out and wouldn't be back till five at the earliestWe then started talking about...

My life as a cross dresser TRUE STORY

In my early teens I had done behind the bike sheds , smoking and playing you show me yours I will show you mineI was a average student but was great at sports , I was asked to play football for the school team and trained with boys two years older then meI made friends with mark who helped me alot and protected me against bullies.The teacher also spent time with me and pushed me to my limit of fitnessThree weeks had past , I was loving life we finished training mark and I was asked to put away...

Sex anyway I can get it Bi Cross Dresser That a

The weeks that followed our "Initiation" were filled with great sex for Joan and I. She has shown me her very submissive side. Something I have tried to pull out of her for years. She loves being tied up and fucked until she begs for me to stop. Once a week she stays late at work for a "moral" building party. Joan's boss tells me she's quite the star although the other girls have become jelious and have been crashing the parties.Chris has joined in on several sex sessions One...

Bi Cross Dresser That s Me

For the longest time I would only top. Then one day my Bi male fuck buddy brought his wife and her well hung boy friend to one of our hotel meets. Her BF was very gentle then once he was inside me he slowly picked up the pace. Soon he was pounding me like a madman. It seemed like an hour but it was more like 15 mins. When he finally came in my ass I saw stars. There's nothing like a real cock filling you with hot cum. This was the one and only time I came from being fucked anally. I've had...

Craig s List Cross Dresser Part 2

I turn you upside down so you back is on the chair with your legs over the back. I take off my pants and underwear. My dick is only half hard but I rub it into the cum on your face and feed it to you with the head of my dick. Then I rub my balls all over your face before leaving them for you to tongue and suck them into your mouth.I am getting harder now. I pull my scrotum up so you can tongue the sensitive area between my sack and my anus. As you lick this area, I reach forward and rub your...

Craig s List Cross Dresser

I find your address and knock on your door. You answer and let me in.I give you a peck on the cheek and give you a hug, with my hand on your lower back I pull you in and feel your body press against mine.I sit in a comfortable chair and ask for a glass of water. I watch your legs and ass as you walk away from me in your stockings and sort skirt. You return with the water and hand it to me. As I take it with my right hand, I put my left hand on the inside of your knee. You freeze and I rub my...

Auto Ride Made Me A Cross Dresser Whore 8211 Part 3

Sitting there with only a towel that too late in the night I was feeling cold. All this as very overwhelming for me, but yet I felt numb. Maybe lack of sleep, the slaps, and all the tears have hardened me to face anything that night. “Here put this on.” Sheena woke me up from my thoughts and handed me a black cotton panty. I stared at it for a moment and slowly pulled it up. My hard and bound cock made a huge bulge. It was followed by a matching bra. Sheena helped with the hooks and used some...

Gay Male

Auto Ride Made Me A Cross Dresser Whore 8211 Part 2

The fact that I was getting excited further had me worried. Now I was sucking her toes. I could sense she too was excited from the way she was moving about in the chair. I started licking all over her feet now. I licked her dirty heel clean and sucked on it. She pushed her toe further into my mouth. I gagged. “Chal chusna seekh le, kaam aa jayega!” the driver said and I was terrified by the implications. By this time the driver’s toes were pushing against my asshole. My cock has gone rockhard...

Gay Male

Telling Mom I m A Cross Dresser part 18 Missy s Halloween Party

I had enjoyed my week of sex with Thomas and Lemar but in the end it left me sore and used but not like I was complaining. It was now getting close to Halloween and mom and I were making plans to go to a Halloween party a few city blocks away from us. Yeah, sounds kind of boring I know but it was no ordinary party with costumes and drinking alone. It was an orgy for bisexual people. It was only a few days away and Mom and I decided to go costume shopping both online and in the local stores to...

Crossdressing

Cross Dresser And Escort Bhabhi

Hello reader! I’m NaughtGuy 21 years from Mumbai and any Girls, Bhabhi, Aunty, Mom, Milf, BBW wants to have some good time for free, email me at This is my real sex story. This is my first sex story, and my best sexual experience, Crossdressers name is Pinky. Escort’s name is Reema (Names Changed) One day, I happened to watch porn in which a guy has fun with crossdressers and a female, it was a group fun which made me really horny, So I decided to jerk off but it didn’t satisfy me, then I...

Milky Cross Dresser Part 1

This is my sex story how I started exploring myself as a guy who always loves to wear women attire and explore myself from a man. I started crossdressing from the age of 16 years. After my 12th standard exams, I went to Delhi from my graduation. I used to stay in Noida alone in a flat. Slowly I started doing part time jobs. So, that I can buy my women attire’s and can live the dream I want to. I started with a bra, panty, and nighty. Later I moved towards salwar kameez. Blouse, Saree, and...

Gay Male

A young cross dresser s first gay experience

I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my sisters red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my sisters panty drawer held no interest for me......they were wrong.It had been a great afternoon jacking off in my sisters bra and panties and watching my first porno when it happened, I saw the most beautiful thing ever, Peter north...

Cross Dresser Become Whore 8211 Part II

I am a Anis a crossdresser and I had got a female persona Sonal and I use to crossdress in secrecy at my home. One day my friend Rajesh caught me while crossdressing buthe like my female persona.That day we make love as lovers. Then whenever we get chance I use to dress up as a girl for Rajesh and he use to make love to me. I had almost become his wife but mean while Rajesh got bad habit of drinking and betting gambling etc.He use to spend lot of money on gambling sometime he even take money...

Confessions of a Sex Crazy Cross Dresser Part 5

I hope you enjoy Sandy's continuing adventures. Please comment and let me know if I should include the next two chapters. Chapter 9: Joe’s Pizza Sunday morning I got up pretty early. I decided to call a cab and go over and pick up my van from Glenn and John’s. After I got back I decided to do some sit ups, as I had not been exercising as much lately. A quick shower after my exercises and then I decided to get ready for my trip. I spent a couple of hours packing as I was going to be gone for...

Crossdressing

How I became a cross dresser pt 1

When I wake up in the morning after a well-slept night, I wear myself a bra and a women’s top with beautiful lace at the bottom. The morning starts much nicer when you get to do as you want. Very often I get an erection just when I wear beautiful women’s clothes. Some mornings I wake up and wear my menswear, a black t-shirt with a big print on the front. That, too, is okay, I am a man, however. In this case, the erection is not visible.In my free time I can be what I want. I don’t think my...

A Surreal Party for a Cross Dresser

Lucy and Stevie had a very open relationship. He knew she loved sex and had arranged many nights where his friends had fucked her. They had planned to go to a party on Saturday night that was not far from Stevie’s house.She could go dressed and really went for it—sexy lingerie, false boobs, wig, makeup, jewelry, perfume and a very short dress. Lucy loved guys getting excited over her. Little did she know what to expect. Just before getting to the house, he pulled the car over and said he...

Group Sex

3 Teen Cross Dressers Misadventure Part 3 Final

I was with two of them on the bed. One of them spread my legs and began to rub his cock up and down my stockings, I could feel him growing hard. The other sat over my chest and told me to open my pretty mouth. I did but no way could I take it all, he must have been around 8". He shoved his cock into my mouth and down my throat thrusting as I gagged. Although I couldn't see, I heard pleasurable moaning from the man on the bed with Sean. Craig, on the couch with Brett said "I’m gonna screw that...

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