Crossdresser indian porn

Crossdresser wanting some dick on the road

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

Bo s Dumb Luck Part One

The year I graduated from a school in 1987, I started working at the hospital full time.I was born in 1969, and the Woodstock gen was my parents; I grew up to excellent music, the smell of some pot and incense, and pretty loose morals. There were disciplines out there I follow. I believed in some; I do not believe in others.Dad is a mechanical engineer. Mom called him "your smart mother fucker", mom was always kissing dad; in return, dad was ever feeling her up, and they had lots of affection...

Crossdressing

Dawn And Patti Move To Denver

Part One: Preparing to MoveI returned from two weeks in Kansas with Patti. During that time, she insisted I dress as a woman. This had worked until my purse spilled and Patti’s friend Brenda Hess picked up my driver's license. Fortunately, Brenda was very accepting, even encouraging me to transition into living as a female full-time.Patti and I were introduced to swinging with Brenda and her boyfriend, Martin. The initial purpose of my trip was to appraise the property Patti’s parents had owned...

Crossdressing

Second Encounter

We have arranged our second encounter to be at a beach house in Duck, on the Outer Banks of North Carolina. You have made the arrangements and sent me the address, and I am to meet you there.I am filled with anticipation as I pack my bags. I include my makeup, wig, sexy teddy, stockings, and my latest purchase, a 38D silicone breastplate complete with realistic nipples. I also pack a one-piece bathing suit and several sundresses and sandals.I arrive at the address and am impressed by how...

Crossdressing

A First Time For Everything

Matt looked exceptionally young for his age and blessed with a complexion that meant he wasn’t all that troubled by facial hair. Spots were non-existent, always had been, even in his teens. Yet at twenty-eight years old you could never classify him as normal. His slim body, born out of long legs and a standard-sized upper torso fulfilled all his needs. He couldn’t be described as ripped at all. In fact, with the right hair, makeup and clothes he would pass as a woman.It wasn’t that he hadn’t...

Crossdressing

My Transition Chapter 4 Crossdressing I

I was a straight-acting 24-year old slim and fit man, once upon a time. Then Sally got inside my head and now, I crave cock. I have evolved from being a school-jock and a dick to being fucked by an older man, then on the weekends by a DJ. I had my ass broken in by a big black guy when the club I frequent was closed. Only for a motorbike gang to dress me as a girl and fuck me silly. At work, I dared not test the waters and dress like a woman but at night I evolved into a full-on...

Crossdresser and I at Costco

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

Crossdresser to Trans Escort Part 3

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

My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or...

olderman and mature crossdresser part 1

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

Crossdresser ke saath maza

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

Incest

CL Memories 1 Crossdresser True Story

I used to get a lot of fun out of CL. I'll post some short stories about some of my experiences there. I sure do miss it. This happened about 10 years ago. I was divorced and living alone, and playing whenever I got the hots and had a good opportunity.I checked CL one weekend night to see if there was any fun to be had, and found a post from a crossdresser visiting a nearby city and looking for company. She (I'll use that pronoun here) had a room in a local motel for the night. I responded to...

Auto Ride Made Me A Crossdresser Whore 8211 Part 5

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

Gay Male

My crossdressing fantasies Free Sex Stories and Adult Erotica Stories

I had an affinity towards womenâ€™s clothes and have a lot of crossdressing fantasies. The soft silks, shimmery fabrics and bold colours â€“ I loved them all. But I was a boy and all my friends would laugh if ever a boy wore a pink shirt. And I loved hose colours. I wanted to raid my momâ€™s closet, wear her dresses, put on makeup and strut like the diva that I was. But I held this in me for many years, until one night I saw my parents. They had dressed up in costumes I believe. My mom was a...

Cross Dresser

Crossdressers in a bisexual sex bar gang bang

I'm sitting in a crossdresser's sex bar – it’s dark. My companion Fifi is wearing only a pair of sheer silk panties in light blue, stocking and suspenders, and a pale blue matching corset that pinches his waist. His balls peak out of the tight panties. I’m wearing silk patterned stay-up stockings in black and a scarlet and black thong. The string of the thong rubs against my sensitive asshole and the soft skin of my ball sack: it’s a turn-on every time I move.A group of men and women approach...

First time crossdressing with another CD

This is part one of a story, from a former user. I’d like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great. First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. —– It was the height of summer, and my girlfriend was out of town for 2 weeks. I’d had a handful of experiences with guys before, but ever since I...

First time crossdressing with another CD

This is part one of a story, from a former user. I'd like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great.First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. ----- It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I...

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...

Crossdressing

Stranger Fuck

I noticed the time strike 10pm on my watch as I got out of the cab outside the Red Circle. Hopefully tonight I was going to get lucky. After paying the cabbie and stepping out of the cab, I fixed my tight pink and black striped dress as I stood outside the club. The Red Circle was the most notorious Sex Clubs in the city where couples and singles went to hook up. Tonight was their Gender Bender Fetish night, which is why I had got dressed up tonight.I have been crossdressing since I was quite...

Crossdressing

Meeting an Asian Sissy

The first time I saw Zoey was on a hookup site. Asian. Mid-twenties. Long black hair. Dressed in a royal blue satin corset, panties, black stockings, and high heels. She didn't show her face or her cock. Just a sexy body in lingerie.It was just still photos on that first post. But over the course of a year, I saw more ads posted to different sites. Sometimes there'd be videos. In one she rode a dildo in a leather dress and stroked her cock. She was getting bolder. She posted links to an...

Crossdressing

Experiences Of A Crossdresser

This is an introduction to my crossdressing experiences – touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever.I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like slips and sheer blouses. I would typically be drawn to anything black, but did have a fondness for nude tights and white slips, also. I usually...

Blackmailed Crossdresser part II

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

Bisexual Crossdresser Fucked By Drunken Roommate

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

Jessi s coming out party

Hi everyone. My name is Jessi, I'm 23 and I have been a crossdresser for over three years. Recently I decided to go full time and was going to met up with some friends to come out to them. I arranged to go hang out with them at my friend Derek's house, them thinking I was still coming as my old self. My roommate, who started my path into crossdressing (that's a whole other story), told me if I was going to come out to friends that I should do it in style. She lent me her cream colored dress...

Crossdressing

Crossdressing Hooker and the Creampie

I've always had a feminine body, slim but some female curves so I've been able to pull of being woman in public a few times already. I started by placing an ad in the local erotic escort guide with some of my best pictures and immediately got replies from interested men. I decided to call one of them who wanted to bring a buddy and we set a date at a local hotel for 8 pm. I wanted to look amazing for the first time so I started by shaving and making sure I had no body hair...

Unexpected Turn of Events

I sat in my favourite bar sipping at my glass of Chardonnay; I had been coming to ‘The R Lounge’ for a couple of years. I watched the guy talking to his friends across the room. They were all dressed with a bit if style but he had caught my attention. He was wearing trousers with a casual blue and black stripped shirt. He was probably five feet nine inches tall. He had an average build; not to slim but trim enough to know that he tried to stay fit. I guessed he was around forty years old. But...

Crossdressing

576 Shadow Oak Drive Part 2

As Molly drove down the highway, I sat in the passenger seat. Although I had always had a feminine side, I was experiencing all kinds of new emotions and feelings that I hadn't felt before when dressed. I don't know exactly what brought it out. Maybe it was the love and support of Molly. Maybe it was seeing myself truly dolled-up for the first time, seeing my own cleavage, having my manhood taped and pushed back. Whatever it was, for the first time in my life I felt more girl than man. Molly...

Crossdressing

The Adventures of Patty

“You're wearing my things again!” Brenda screamed when she came home early from community college and found me prancing around the house in one of her short skirts. “Take them off, you little pervert!” It wouldn't be nearly as bad if I were her little sister and trying on her clothes but I was her brother. But it wasn't as bad as it could be. I mean, if she knew what Tommy and I had been doing just two short hours ago, she'd really be pissed. Truthfully, Tommy and I had never really done...

Crossdressing

Duped Into Being a Crossdressing Bull Part I

During my second year in college I was in between girlfriends and at the time I was greatly indulging in my crossdressing fantasies. I spent a lot of time in lingerie sections of stores buying bargain panties and bras since that is all that I could afford. The pickings were fairly slim for a big guy, so I developed a love of granny panties because those are so easy to find at a store like Walmart or Target. Craig's List and similar websites did not yet exist at this time (including Fet-Life)...

Becoming John Collins Mistress Part Two

The next day, everyone was a bit hung over. I needed to pick up my car, which I’d left at the bar the night before. Joe said it was on his way and he’d be glad to take me. I borrowed a raincoat from John to wear over my skimpy outfit, then Joe and I headed out. Joe was making eyes at me during the drive, and I decided it would be best to come clean. “Joe, there’s something you should know about me,” I started. Joe quickly said, “Hey, baby, there’s a lot I’d like to know about you.” “Yeah,...

Crossdressing

First crossdressing experience 3 cocks in1 hr pa

I started with crossdressing a few month ago, first just panties or strings when i had a wank over videos and pics of other crossdresser getting taken or dominant trannies and women humping devot men.By now i wear black stockings and suspender belt, a white lace string, black shiny mini skirt, white blouse, 4" black heels and a blonde wig.I also had an extreme urge in me to feel a real cock in my arse, to satisfy these needs i began to visit adult cinemas in my area, first just with stockings...

The story of how i began crossdressing Part 1 3

Entry #1:I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :PI decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She told me she’s looking for a slave to entertain “them”Thought it was a spelling mistake (since it was german its not really much of a difference)So i agreed...

A Crossdresser rsquo s Life

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

firsts time I m seen as cd crossdresser

From a young age I liked dressing up in womens lingerie and clothing.... as I got older I grew up over weight a little and more so the older I got..... by the time I was I was in my late teens I had nice size breasts....nice enough to fill a bra. So worked up the courage to buy some lingerie online and when I received it in the mail I was so excited. I couldn't wait to try everything on.... I had brought a white lace bra, matching panties and white suspenders and stockings.....I tried them...

Losing my crossdressing virginity

This is the true story of my first time with a man while fully crossdressed.I answered an ad in the local paper for a guy looking to meet a crossdresser and exchanged some text messages before agreeing to meet.I took the bus to where we had arranged to meet, it was a flat in a not great area of town. Nervously I rang the buzzer and entered the block, getting the lift to the fourth floor I went to the door and rang the bell.The door was answered by a man in his early fifties of middle eastern...

first time web hook up crossdressing dominatrix

crossdressing has always been my secret pleasure I even had a cache of out fits make up wigs and heels. it started when I was younger but evolved as I got older, now as I got older ive refined my skills and abilities and can pass as a girl when dressed. I had fooled around with guys before but I had never dressed for one only indulging in self pleasure with toys and my fingers. when I got off work on friday I was excited for the up coming three day weekend going home to get dressed up maybe go...

The story of how i began crossdressing

This is copied from my blog http://cdcutiepie.tumblr.com, so the main updates will be therei did think it would be nice to have it up here as well though :)Entry #1:I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :PI decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She...

Crossdressing Karte Hue Pakad Liya

Hello indian sex stories dot net friends , my name is preeti(fake name) age 20. Ye baat kafi purani hai lagbhag 3 saal pehle ki . Mai ek part time crossdresser tha aur mujhe meri chachi bahut pasand thi aur hain . To mai jab vo aur ya koi b ghar pe nahi hota tha to mai unke room mai jake unke innerwear pehnta tha . Aur jaise ki mujhe bondage bahut pasand hai to chachi ke kapde pehnke self bondage karta tha jab ghar pe koi ni hota tha . Isi tarah ek din ghar pe koi ni tha aur mai chachi k room...

Summer dressing

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

Crossdressing

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...

Crossdressing

A Tale of Two Clitties

A Tale of Two ClittiesOne day I was checking out the bulletin board in a local adult bookstore. My eyes danced across the listings. Dungeon masters, couples looking for a third, but then I stopped, there it was, "Lonely virgin crossdresser seeks same". My heart jumped in my chest, and my cock twitched in anticipation. I tore off a tab with her number and promised my feminine side I'd call.A few days later I finally worked up the nerve to call her. I had battled all the familiar fears; would I...

Crossdressing

Son s Bikini

It was a hot day. I told my mom, “I'm going to cool off in the pool.” My sister, Jan, was already out there sunning herself.Mom eyed me over. “You know, Mark, that swimsuit of yours is getting kind of old. You should get a new one. I'll look online to see what I can find for you.”Mom and Dad divorced several years back, but the split was amicable. Jan and I stayed with our mother as Dad traveled a lot. Mom did well working as an executive in a local company. Jan and I each had jobs elsewhere. I...

Crossdressing

Pinked

At twenty-five, everyone Brad knew said he looked a lot younger, more like nineteen. He'd still get carded at bars which both intrigued and annoyed him. He had a good if boring office job and had his own apartment. Like most guys, he also watched a lot of porn at home and would jack off. At first, it was just the usual stuff, large breasted women sucking and fucking big stiff cocks, drinking their cum or getting facials. After a while though, he'd ventured into more what he considered bisexual...

Crossdressing

Spying on my sissy slut husband

Part oneI am married to a very sweet guy. We are both twenty-two years old and have been married for two years. Our sex life is great; he is very horny and affectionate. I never have to ask for sex as he is always willing and able.He is a Social worker and I am a nurse. We met while he was in the hospital where I work. He was working on a child abuse case. He isn’t a hunk by any means, in fact, quite the opposite; he is very feminine. Maybe him being this way attracted me to him as I had...

Crossdressing

Pleasing Bill A Crossdressing Story 2

“That’s what i like to hear. Now at 12AM tomorrow i want you to be at our house dressed up in the sexiest outfit that you can get your hands on. I’ll text you our address.” “I can't. My family are still at home by 12.” I pleaded. “That’s not my concern. Now this is your first task i’m telling you to do. Are you going to fail me already? Because you be here at 12 o'clock on the dot or you can forget about ever seeing me again.” Bill said annoyed. I couldn't disappoint him. I need to...

Rite Of Passage John Or Jennifer

John turned eighteen that day. His father was at work. His mother and sister Lisa were spending the day shopping, saying they wouldn't get back until very late in the afternoon. He decided he wanted to pamper himself, celebrating in the best way possible. That way was by dressing up as a female. John had been a crossdresser since he was sixteen. He believed he had managed to keep that part of himself hidden from the rest of the family.After taking a luxurious bubble bath, he carefully made up...

Crossdressing

The Brother Bride

My twin sister Julie and I had always been close. Growing up, we shared each other’s deepest secrets. I had always told her I would do anything for her.Julie was a girly-girl, and loved being female. She had said she would be happy if she could wear dresses and heels all the time. Her wardrobe reflected that. She had also known about my urge to wear female clothes since we were young, and being my dear sister, never told anyone else. She told me she could never mock me or embarrass me in front...

Crossdressing

Practice Pays Off

It was a beautiful Saturday late afternoon. I was done with all the things I had to do around the house. My wife was gone for the weekend and I was feeling a bit bored. I thought I would take a shower, shave and pull out the makeup and see if I could do myself any justice in looking passable. Many attempts before had failed, but I was getting a little better each time.I got out of the shower and was nice and clean, smooth from head to toe and went to the bedroom and pulled on a pair of my...

Crossdressing

Crossdresser Stories 8211 Assfucking in panties

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

Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5’10’ in height. She is also a fairly busty woman with a 30DD chest with about 35′ hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

Wonderful crossdressing shopping experience

Following is a true account of my recent experience of shopping for clothes (crossdresser, no sex). I just wanted to share a couple of very pleasant experiences I had shopping at the Natick Mall near Boston. It was the first time ever that I managed to shop with confidence and without any stress. I really want to give compliments to lovely women who made this possible (in case any one of you ever went to shop there, tell them about this story). The first experience I had was at a small...

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...

Crossdressing

How to Treat a Lady

Being a pretty, petite, believably passable crossdresser makes me a very happy person. I have been dressing up as a sexy girl while daring to go out in public for the past two years since I was sixteen. I have had this urge and desire to dress as a female for as long as I can remember so I have gradually come to accept that I have a feminine side that needs to be nurtured and encouraged.I have managed to accrue several wigs, dozens of dresses, many pairs of high heels and enough makeup to last...

Crossdressing

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...

Crossdressing

My first time in a bar

For a while now I had been chatting with a sweet guy named Allen, who was bisexual and was eager to meet a crossdresser. He was very muscular and handsome, a hard body but with friendly eyes. He seemed to really like my pictures and said he had cum, stroking himself, while looking at them several times, and was eager to meet me in person. He wanted to meet in a bar which is something I had never done before. I have had sex outdoors before but in a secluded spot, I had only toyed with the idea...

Crossdressing

Being Christy Part 3

My experiences with Jenny and James had been amazing, but summer drew to an end and it was time for me to take up my place at university. I didn’t need much and only took a couple of bags with me, but the move did mean saying goodbye to my sister’s wardrobe. My parents gave me a lift to my student digs and after some typically over the top parental farewells, I was left alone three hundred miles from home.Settling in to student life was simple. There was an immediate social network in my fellow...

Crossdressing

She Made My Dream Cum True

I had been seeing Ellie for a few months before I told her about my little secret. We enjoyed straight sex, but something was always missing for me. After I told her about Vanessa, and my desires to dress up and be treated like a woman, I was really scared she was going to cut and run, but she actually was interested in knowing more. I confessed some of my innermost desires to her. I told her about how I loved being with her, but that I really wanted to know what it was like to be with a...

Crossdressing

My best friends dick

I was a closet crossdresser with a crush on my best friend and finally, after we had both graduated I worked up the courage to show him how I felt. I invited him only and met him at the door dressed in my sexiest/sluttiest outfit. I fell to know knees and gave him his first bj. It was also the first j I had ever given. It was wonderful for the both of us. It was something I had wanted to do for a long time and he had no idea that I was into cross dressing or wanting to be with a guy. After...

Crossdressing

crossdresser confession part 1

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

Crossdressing

The Best of Both Worlds 2

"Oh, God, Daniel!" Arya cried out in ecstasy, as her body came to orgasm. Sitting on top of Daniel, she let her body bounce on him, as he shot a load of cum into her with every upward thrust. She screamed excitedly with each push that Daniel gave until he was finally finished, and Arya rolled off and lay beside him.The sex had been both exhilarating and disappointing. As always, it physically felt incredible, as Daniel certainly knew what he was doing in bed. The problem that brought the...

Crossdressing

It Wasn t Love But It Sure Felt Good

Al called me first thing Saturday morning to express how much he enjoyed our time together last night. He also asked if we could do it again soon. I told him that we could this coming Friday if he was available. I could show him some of my other outfits and the pictures that he took of me as well. He gleefully responded that it was a date.As the week progressed ever so slowly, we spoke at least twice a day and were both looking forward to Friday night. I spent my free time trying to decide on...

Crossdressing

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...

Crossdressing

Crossdressing With Walt pt2

Walt and I headed out to the living room and as i sat down, Walt went into the kitchen and came back with two beers. As he sat down next to me he handed me a beer and for the next several minutes we sat there quietly drinking our beers. Walt finished his first and after he put his empty can aside he looked over at me. "You were fuckin' great" he said as he moved his hand over and laid it on my crotch. We were both still had on our outfits and as he now started to caress my crotch, I looked at...

Crossdress Rendevous

I had to be out of town for a few of days for a demonstration an I knew there was a alternate lifestyle club located there and so I decided to take along with me a white silk dress, bra and panties and white hose and a pair of white stiletto heels. I didn't tell Carmen that I was hoping to connect with another man for sex, me dressed as a crossdresser in my outfit. I had finished early with the demonstration and went back to my motel and quietly changed into my white outfit. I left the motel...

Office Caught

My name is Peter. I'm twenty three and I'm a member of the small internal IT team at a large corporation. It's a typical office setup and our small team of three were kept busy with the day to day tasks; failures, PCs and printers and general support. I'm generally pretty quiet and unassuming and, whilst polite and good at small talk, I'm pretty shy, so just keep my head down and do my job. I joined as a junior aged twenty one straight from University. The office was full of people of all ages...

Crossdressing

Jaime s Way part 2

I awoke to feel the dried cum on my face, ass and balls, and then remembering how I got that way made me smile. Crawling out of bed I made my way to the bathroom and took a hot shower and then easily shaved my already smooth legs. Out of the shower I brushed my hair and did what I could to make it appear more feminine. After I put on my make up I walked back to the bedroom and slipped into a pair of sheer blue panties. The cage Sherry had put on my dick prevented me from jacking off but since...

Crossdressing

I AM A Slut part 1

My roommate and I live in a nice house in a very nice neighborhood. We're roommates because of convenience and not because we're lovers. Well, not steady lovers anyway. Sandy is drop dead gorgeous and a very free spirit, meaning that when at home she is usually running around naked or nearly so. I'm a cocksucking, take it in the ass crossdresser with very little interest in women. I guess when you get down to it both Sandy and I are cum dumps. Yes, it's a strange living arrangement but we like...

Crossdressing

The start of my life as a submissive crossdresser

I am a bisexual cross-dresser/sissy and have been enjoying my life as such for many years. It all began for me when a friend asked me to look at some of his 'girlie' magazines.We went up to his bedroom and looking through the magazine got Chris really excited and he got his cock out and started to masturbate. I couldn't take my eyes off his cock and I slowly reached out and touched it and when he removed his hand I curled my fingers around his erect shaft and began to slowly wank him.I just...

Crossdressing

Carolyn Makes Her Way Part 1

After tucking my penis and balls away, I started dressing with the basics: panties first, a sheer yellow thing, then my bra with the silicon helpers we girls so love and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of how it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long sleeve silky cream colored number that I left the top two buttons open.Dressed now, I went to the vanity and...

Crossdressing

Carolyn Makes Her Way

After tucking my penis and balls away, I started dressing with the basics, panties first, a sheer yellow thing, and then my bra with the silicon helpers we girls so love, and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of house it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long sleeve silky cream colored number that I left the top two buttons open. Dressed now, I went to the vanity...

Crossdressing

The Next Night Crossdresser Part 2 of 2

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

Crossdressing

Jenny Learns Her Place

His hands held my hips tightly and his very large hard cock slammed into my asshole again and again, as if he were was going to ram it all the way out my mouth. I whimpered with each long stroke while my own small dick dripped the remains of my orgasm. It was amazing that he was hard so quickly after pumping my mouth full of sweet jism, some of it even spraying onto my face. “Oh! Oh! Oh! Ooohhh fuck me good, baby,” I moaned over and over. I'd known Bobby since grade school and had even enjoyed...

Crossdressing

Simran A Crossdresser Part 3

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

Crossdressing

First Time With A Crossdresser Part 1 of 2

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

Crossdressing

Memoirs of a Crossdresser Chapter 1

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

Crossdressing

Crossdresser Business Trip to South India

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

All The Way Part 3

When I awoke it was later than usual but considering the fact that I'd been through back to back fuck marathons in as many nights, I thought it wasn't bad. Slipping out of bed I stepped into a robe and went to the potty, before looking at myself in the mirror. I was a mess so I took the time to freshen up my makeup, washing some off before putting any more back on. Satisfied with how I looked, I padded to the kitchen and started the coffee before taking out the eggs and breakfast steaks. I was...

Crossdressing

All the Way Part2

When Michael stepped inside and closed the door, he gave Kathy the same kind of kiss as his wife had. He was quite an imposing man; short cropped blonde hair, very piercing pale blue eyes, a little over six feet tall and built sturdily, weighing somewhere around two hundred pounds. My heart skipped a beat when I took in the complete picture. Now I wondered how Kathy would convince the woman to get naked while her husband was right there. Donna gave me a hug and a nice kiss and then her husband...

Crossdressing

Simran A crossdresser part 2

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

Crossdressing

Simran A Crossdresser Part 1

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

Crossdressing

Free Clothes

I guess it is something that goes through the mind of every new or closeted crossdresser. Shopping for new clothes as a guy is awkward because it is difficult to do without making it obvious it is for you. Yeah you can go online, but it’s tough if you’re not used to the sizing and the clothes never seem to look the same as the picture. Thus, when searching for playmates on Craigslist, if you find someone purging some clothes, you have to check it out. And that’s exactly what happened. I was...

Crossdressing

Crossdressed In best friends mom clothes 3

I woke up the next morning alone in bed. I didn't had a clue what time it was. But my head felt somewhat sore. I can only remember climps of what happened last night. I then realized that i was still in her lingerie, and that the door stood open to the bedroom. As i laid there, i could hear a radio going in the background. “Good Morning!. The time is now 10:30 and your listening to Radio Morning Tunes” Then Queen with bohemian rhapsody started playing. I then heard Margret started singing, and...

Crossdresser gets more than she bargained for

My story is like many I have read on here and which I only fantasised about, till now. This story is all true, I thought about embellishing it to make it sexier but thought I’d let you know what happened just as it did. A short history of me and dressing up first.I have been crossdressing for as long as I can remember, from sneaking a pair of my sisters panties, to even sneaking into the gardens of my parents neighbours and pinching underwear from washing lines. In my late teens when I found...

Veronica fists me crossdressed Part 2

I'm sure you all know how tomorrow can turn into a year, but better late than never, right? Sorry for the delay! We didn't get to tape the finale of Veronica's session with the crossdresser with two cocks. That was a shame because it was a rare and unbelievably hot scene that will never be duplicated. But I certainly couldn't deny the woman her "pussy time" to get more tape! She was completely satisfied except for what she had planned for me. I did talk her into getting more tapes so she...

Tyrone s Crossdressing White Pussyboy

Submissive whiteboi becomes a sissy faggot pussyboy for his nigger master.It was to be a night of romance. My Nigger lover, Tyrone, gruntedas he pulled his glistening cock from my aching, cum filled asscunt. Hehad just shot a massive load of man slop into my steamy, grippingentrails. Our lovemaking had been a brutal affair, as it always is, which is just the way I like it. I am a subjugated fuck slave, nothing but a sissy faggot sperm receptacle for my dominant nigger lover.Tyrone is the envy...

Beginnings My First time as a crossdresser PT 1

( Hi I am repostng because I want to string everything together for continuity ) Everything is connected so you should start at the beginning.) (This is a true story, the conversations in it are only as accurate as my memory can supply, as this happened Thirty years ago)When I was 17 I was dating a girl from the local college. I lived in a medium sized college town in a western state and it was 1983. It was Halloween weekend and we were both drinking some wine coolers she’d bought, the drinking...

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...

Crossdressing

Motel Fun for College Crossdresser

Before I start the story I want to describe the setting so you get a better idea: it's a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that's for sure. The layout of the motel is a rectangle. The rooms surround the rectangle's perimeter, in the center there is a pool, a park area, and a parking lot. There is a walkway around the entire inside perimeter of the rectangle and every room has two doors, one facing the exit and...

Crossdressing

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

First Crossdressing Sex After Marriage With A Mature Guy

Before I bare the details of the night that took me back in time, I should tell you a bit about my past, and my present. Before marriage, I used to cross-dress quite often for tops who enjoyed my slutty alter-ego. I enjoyed being the dressed up slut, begging and hogging on cock. I had shoulder-long hair, pretty slim body, and I used to keep it hairless. Despite all that, in normal life, I looked pretty much like any straight guy. But with the right dresses on, a bit of makeup and lipstick, I...

Gay Male

crossdresser ashley this my story

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

A Tale Of Crossdresser

Hey, this is my first story that I am writing but not definite new to the glorious crossdressing field, Kindly forgive me if there are any mistakes, suggestions are welcomed people who are moving to Bangalore or in Bangalore if they want to my friends or a hook up we a cross dresser can contact me at m First, I don’t have a perfect girl figure but I wanted to be dressed as a girl, do a girl activity from a long time but it didn’t come true. I always used to wear my mom’s clothes like bra &...

Gay Male

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....

Crossdressing

Telling Mom I m A Crossdresser Part 15 2 Kinky Girls

It had been a week since Mom and I spent the 4 days at the spa and hung out with my old babysitter Laci and for a while it was back into our old routine of working and coming home. Day after day I kept thinking about how her warm wet pussy felt wrapped around my cock while the feel of a sexy thong rubbed against my asshole.I came home one day to find my mom was packing a bag. I asked her what she was doing and she told me that she was going out for the weekend to visit an old friend from high...

Crossdressing

Telling Mom I m A Crossdresser Part 14 Back to the spa and a familiar face

Part 14: Back to the spaI'm sorry this story is a fair bit longer then my usual ones however I didnt want to separate thes and have another story with almost no sex in the first one so soon. Having said that I hope you enjoy my story and please read the whole thing. I promise you will not be dissappointed. I woke up the next morning lying next to mom in her bed. I was wearing a pair of white stockings and a corset and mom had her bra on. After Thomas had left Mom and I spent the night licking...

Crossdressing

Telling Mom I m A Crossdresser part 13 5 Missy Brings Home A Stud

I told Thomas all the details of why I was out this night and he loved the idea. He took one of his Viagra and he led me out of the bar. I felt a little embarrassed at all the cum leaking down but some of the cross dressers were just smiling at me like they were saying “you go gurl!” which made me a little proud.Thomas followed me in his car until we got to my place and I took him by the hand until we got in the door. When I walked in I heard a thumping upstairs and asked Thomas if he would...

Crossdressing

Telling Mom I m A Crossdresser part 13 Missy s Turn

Sorry not much sex in this one but its a lead up to 13.5 and I hope you enjoy both of them. Once mom and I had gotten our car back, we took it out for a spin and I have to say it worked and looked like new. It had everything from a new paint job to new parts in the engine. Now in all honesty, I did have to go back a few times and give Ray a few blowjobs to help pay for them but it was definitely worth it and I didn’t mind sucking his huge cock anyway. Mom helped as well by going over to “visit”...

Crossdressing

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