Do It Yourself True Transvestite Story
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My now ex-wife Karen H is in her sixties now. Over many conversations and indiscretions on her part, I have much of her sexual life written down, but not all of it as she was such a slut. I enjoyed her telling me her sexual past and though it happened years ago, I will always treasure the voyeuristic moments that she shared. When Karen was 16 years old, she was with one of her first boyfriends (James) and during their dates she loved being fondled and touched, as you do at that age. She was a...
This is the sequel and finale to the first storyAfter a great fuck session with Angel, we were applauded by our fans in the next room, Mike and Craig walked in and they were cheering and hooting, like fans of an Arsenio Hall show." Hey Angel, I did not know you had it in you,your such a naughty girl", said Craig. We were both still naked, and sweaty and Angel was a little surprised that the guys were listening. She was mad and ran into the bathroom with the bed sheets wrapped around her. She...
I hadn't seen my uncle Jon since I was 10. He had been over seas serving in the military and then had lived in Korea for 3 years. My parents told me he was coming back to live in the States. He would stay with us until he found a place of his own. After all he was my fathers brother. I barely remembered him and they said it would be good to get see my Uncle. He was family. I thought that would be great. I heard so much about him from my dad. I had just turned 17 years old. It...
Introduction: 17 year old girl seduces her hot uncle Intro: Just another made up character of mine. I wrote this in about an hour with no editing. I plan on writing the followup to this. I hadnt seen my uncle Jon since I was 10. He had been over seas serving in the military and then had lived in Korea for 3 years. My parents told me he was coming back to live in the States. He would stay with us until he found a place of his own. After all he was my fathers brother. I barely remembered him and...
The Private Transvestite Detective (Or The Undercover Dick) By Michele Nylons With apologies to the writers of the various movies from which I borrowed some inspiration (and a few good lines). Chapter One It was late Friday afternoon and I sat behind my desk smoking a cigarette, leaning back in my chair with my high-heels resting on yesterday's newspaper. I contemplated my red-painted...
Last night I went into a local porn shop to pick up a cock ring and a ball stretcher. I’ve had this fetish about how I love low hanging balls on men and decided I’d like to try to stretch mine. The clerk was a very nice middle-aged woman who took me around the store to find those items and she described everything as we walked around. We went to the back of the store and could see an area with video booths and I could hear lots of moaning from one of the movies. I had heard of some store booths...
I recently got divorced having had to move out I was looking for a mattress. I went to one of our local mattress stores in the store clerk there was with someone. I was forced to look around the store for a while without help. The girl there noticed me and said she would help me when she was finished up with this customer. So I’m going bed to bed laying on them trying to figure out what I liked while I waited for her. The whole time that she was helping that person I noticed that she was...
(Are you the girl we met? Get in touch!)My wife and I were spending 2 weeks in Mexico. We've been to swingers clubs several times and my wife is definitely fond of a ladies company.We were spending our days around the pool watching all the girls in bikinis, and getting horny. By mid-afternoon it was too much and we'd sneak off back to our room to fool around and screw. Then in the evenings we'd watch the hotel entertainment. Eyeing up the same girls wearing their tight dresses and short...
it all begin when i graduate from high school,i was at home bored and had nothing to do,so i decide to go look for a job.when i got the job the next week i started training for the job, 23 of us started on the job...this was my first job and i was nervous so i wen and took a seat and and i saw this beautiful woman next to me sh look a little older about mid 30's i think 32 years old. we started talking and for that one month of training we became friends.as i remember it clearly it was the last...
Most weeks I'm away on business, which leaves my wife home by herself quite a lot. I feel bad about this, so about three weeks ago I decided to buy my wife a gift. Something to keep her company while I was away. I actually asked a colleague of mine, a co-worker, what I should get my wife. He laughed and said, "Fifty Shades of Grey, man," like I should know what he was talking about.Mind you, I don't watch the news, watch TV or read the news online. I'm a stock broker and a marathon runner on...
I am a horny little nympho. I'm the first to admit it. I love dick. I love pussy. Ever since my cherry was popped ive been hooked. But as many dicks as i try and as many guys as i take at once, there has always been one dick ive went back to no matter what. And that dick belongs to gsgangrel. He was the 3rd guy i ever fucked. He is also the first guy who gave me a genuine orgasm. We dated for a while and we had a great sex life. My appetite for sex had always been big but after i felt my...
it all begin when i graduate from high school,i was at home bored and had nothing to do,so i decide to go look for a job.when i got the job the next week i started training for the job, 23 of us started on the job...this was my first job and i was nervous so i wen and took a seat and and i saw this beautiful woman next to me sh look a little older about mid 30's i think 32 years old. we started talking and for that one month of training we became friends.as i remember it clearly it was the...
I was working in a local factory that employed about 1100 people. The assembly line I was on had about 110 people both men and women. This was the second factory I had worked in and it was totally different than the first. The first had only two women and the second had almost as many women as men which was good and bad. Anyway, I was just doing my job, minding my own business when a female union steward came up and started talking to the guy working next to me. They were just bullshitting,...
Chapter 1 This is a story that was found In Sin Loos. It appears that someone in Sin Loos wrote it before the city was defeated. No one seems to be able to verify whether or not it's true. It is known that women were mistreated violently and cruelly. Extreme caution should be exercised before reading. It is a violent, sad story and doesn't end well. My name is Ban. I turn eighteen today. Years ago, Master had decided to terminate my service to him on this day. I will tell some of my...
* This is transferred across from my old profile (LookingForSomething) *This isn't a 'story' at all, because it really happened. I just thought I'd share my experience with you; perhaps you'd care to comment if you enjoyed it, found it sexy, or want to know more.There isn't a 'transvestite' niche on xHamster, so this is filed rather awkwardly under 'Shemales' 'Gay male', and 'First Time'.OK, about 15 years ago I discovered that I got turned-on by 'shemales'. Let's be clear about that: shemale...
This isn't a 'story' at all, in the sense that it really happened. I just thought I'd share my experience with you; perhaps you'd care to comment if you enjoyed it, found it sexy, or want to know more.There isn't a 'transvestite' niche on xHamster, so this is filed rather awkwardly under 'Shemales' 'Gay male', and 'First Time'.OK, about 10 years ago I discovered that I got turned-on by 'shemales'. Let's be clear about that: shemale is a casual term for transsexual men, that is, they were born...
TRANSVESTITE MAID (A story that may not be what you think...) by "c.c. The day I discovered the truth about Cynthia's Transvestite Black Maid marked a turning point in my life. But I didn't know it at the time! We had just finished making love in her lavish bedroom - which was in her luxurious condo apartment-which was in the most exclusive condo development in the city-and were lying in Cynthia's bed, atop the covers, gasping with pleasure as we recovered our strength, her...
My aunt and uncle lived two doors down from me when I was growing up. They had a son one year younger than me. We played together all the time and I was at his house or him at mine all during the summer months. My aunt was a big woman, she was 6ft. tall and weighed around 165. She was even taller in her 3 inch heels. She had long auburn hair with beautiful waves in it. She wore a 9 1/2 shoe. Her hands and feet were large, but so sexy looking with nail polish on. Her blue eyes would melt you....
I’d enjoyed soapy showers then sex with hubby but didn’t feel sexy while caring for babies. Sex was another domestic routine, a chore for his horny rush. I didn't care. It was duty booty. I accepted his need, was pleased he wanted me, was happy to give it but just didn’t feel sexy. If aroused I had to get mine on top first but usually was too tired and laid back and let him have it, pleased he wanted it.As the kids grew out of diapers and choo-choo train baby talk ended, however, we began to...
CheatingThe job of a traveling salesman can be very lucrative but being a road warrior can also be exhausting. That type of job is usually handled better by younger men, but I have been very successful. It's hard to give up the commissions and bonuses for a mundane desk job back home at our Minneapolis headquarters. I have been on the road an average of four days a week for the last twenty-five years. My name is Ed, and now at forty-nine years old it has taken a toll on my marriage.With me being gone...
TransFirst of thanks for reading my story!Second of course this isn't my first sexual experience but it was my frist with a transvestite/maleIt was 5 years ago, i found her on a sex contact website. I kept looking at her profile for months, building up the courage to contact her. I finally did no answer. I hung up the phone my heart pounding out of my chest, i felt disappointed. I took it as a sign that it wasn't meant to be. However i decided to give one more try later that afternoon. She picked...
Transvixen By Michele Nylons Chapter Five: Panti Pops Her Top Cherri had no intention of going to lunch. She read the contract on the bus on the way back to Debenhams and did some mental math. If Wendy was right about the band's success Michelle Murphy could set herself up in her own right. She could move out of home and live full time transgendered until she decided how far she intended to transition. It was early days but she knew she couldn't keep living a lie. Mike...
"Please don`t make me beg for it…" he said,"…please." He knelt face down on the carpet, his hands tied behind his back, his ass jutting in the air; his pantied ass, clad in the shiny, smooth, black nylon, lace-trimmed women`s knickers. The high-heels of his shiny patent leather shoes pointed up towards his tormentor, their straps taught round his ankles, the smooth toe-caps polishing themselves on the thick, white pile carpet. The black nylon suspenders stretched across his soft, white, shaven...
Fetish“Sssss” “Sssss” “Sssss”Jacob dropped the raw hamburgers and brats onto the hot grill as I walked out the back door. Immediately, the sound of the grease sizzling and the smell of the fat cooking made my mouth water. The potatoes had already been incubating in their shiny tented foil homes, and the seasoned vegetables were in their wire basket, anxiously waiting to join the fiery party.I slid my arms around the waist of my shirtless, sweaty chef and peeked my head around his arm, sniffing, “Mmm,...
Straight SexThe first time I was with a transvestite was only by happenstance. It was late at night, and I was in the parking lot of a porn shop, drinking a beer before I went in to watch porn in one of the booths. I saw a woman come out and get into her car. She looked at me and smiled when I tipped my bottle up for another drink.When she started her car, I turned on my own car, and then followed her down the road. As we drove, I was thinking that women do not usually go into a porn shop alone. Then at a...
Transvixen By Michele Nylons Chapter One: Panti and Cherri Pops Panti's red nailpolished finger lazily circled the glans of Cherri's erect penis through Cherri's gauzy nylon pantyhose gusset. Preseminal fluid seeped from Cherri's palpitating member and darkened the sheer nylon. Cherri's white satin panties were bunched around her thighs and she bucked and heaved as Panti gripped Cherri's engorged phallus and stroked it until creamy white semen erupted from the eye of her...
This is a continuation of Carli - An Uncle Travis Story part 1 published as a Post. You may want to read it first, though this does stand on its own, I believe.That next weekend, Ellen told me that she was going shopping with Jennifer and Carli and that they would be gone most of the day on Saturday. Carli had been begging her mom for some new clothes and Jennifer recruited Ellen to go with them. Jennifer and Ellen had been friends for longer than Ellen and I had been together. They had been...
It was a sunny Saturday afternoon. The sun blazed high in the sky, the blue ocean shimmered with light as the waves crashed rhythmically onto the shore. Noah Centineo walked side by side with his girlfriend Alexis Ren. He gazed adoringly at her, unable to get over how gorgeous he was, and how fortunate he was to have a woman like her. With all good things come bad things. Noah thought about how other guys would check her out wherever they went, sometimes blatantly and sometimes they attempted...
I noticed her right away, or maybe I should say, I noticed him. It didn’t matter then and it doesn’t matter now, “she” was so beautiful, so strikingly beautiful. I was stopped in my tracks, as they say. Struck like a lightening bolt by her gorgeous face. I thought to myself that this had to be the cutest, most boyish girl ever or the cutest, most feminine boy ever. That first glimpse of her happened as I walked through an up scale, expensive, department store. She was working there and when our...
THE NIGHT OF MY WIFE'S GANGBANG IN A NEIGHBORS DUNGEON[/b]Spontaneity can lead to the most erotic and fun adventures that await. Leaving caution to the wind and going with what is happening at the moment are some of the times we most cherish on our sexual experience. One such night of depravity transpired at a neighbors BDSM thralldom basement gathering. On the surface, Rick and Jan were the banner couple of suburbia....
Life's a bitch, and so am I now This is a fiction story!! The people in the story are not real!Please exsuse the puntuation and spelling I'm just a blond sissy!I start of my story with my wife leaving to go bingo with her mum, as soon as the car pulls away I'm up to my secret girl cloth's and sex toys.I am a sissy cross dresser, I can't help it i love the feel and how girlie it makes me look. I have tried many times to stop but I cant, so i lay on my bed and put my computer on. I don't know...
This week when I met Irene for a short after work session, she wasn’t really into it from the beginning. Something had happened at work. Is it a running joke or is it real: as a typical (?) woman Irene had to talk about it.At first I thought ‘shit, I want to f*ck and not listen to your problems’. But then it turned out to be not that bad. In fact it was quite amusing…Irene does have some sexual relations around her job, that is known ever since. But neither me nor any of my buddies work in the...
My name is Mitty Linden. I am 49, single, white and an ass addict. Don't judge me too quickly. Listen to my story and tell me if I had any other choice. Like so many women here, I am a mother of a 21 year old, beautiful boy. I still remember when Justin was born. He was so beautiful that one look at him, and I forgot everything else.I forgot that I was single and hand no one to care for me or my c***d. I forgot that I was broke and had no money to care for him.I even forgot that my "boyfriend"...
Back to work.There are two sides to every story.The wife’s story.I’d finished my lunch, hardly a hearty meal, but I did feel a little like the condemned. I sipped my drink, and listened as Gerry chatted to my husband. They’d always got on well, and had been catching up. It had been five years since I had last “worked” but the recession had hit us hard, and me in particular. Mike would have given me the cash to see me by, but I was too stubborn, or too proud to take more money from him. I’d...
After the cocksucking session, Henry had reinserted the inflatable buttplug. He was fascinated with gape. Having rested for a few hours, Henry reinspected my pussy and told me that my gape was improving. He stuck the plug back in and inflated. The pressure was intense, just beyond pleasurable until my hole adapted. He bound my hands again and tightened the nutsack rope. He then took the leather belt and cracked my cheeks a few times and waves of pain and pleasure rushed through my body. My...
Miley stewart had been posing as the teen pop sensation Hannah Montana for as long as she could remember. She knew the basically every guy in the country wanted to fuck her. Some guys had even gone to her shows and begged her to take her top off on stage, but miley knew her dad would kill her if she even thought about that. Miley on a few occasions had found herself rubbing her wet cunt and eating her sweet juices. But one day things changed Miley had walked into the house and threw her blonde...
Guys! To understand this New Fictional Story of mine, U must know the meaning of few Indian words, which will be constantly used herein:-'Mangalsutra'- A necklace worn by women as symbol of her marriage.'Saree'- A Beautiful Dress, which a majority of Indian Women wear.'Blouse'- A Sexy Bra, worn with 'Saree'.'Pallu'- A piece of cloth from 'Saree', to cover blouse.'tilak'- A Red Colored circle, made from powdery stuff and applied right above forehead.(Here it Goes)This is sameer and my mom is...
Sweet transvestites from transexual transilvania.......sweet transvestites..... I don't know about you but I love Rocky horror picture show and in particular I really love that song, why you ask? well for starters it has to do with the fact that I myself am a transvestite a crossdresser if you will and yes I am still one even though I have not dressed in a couple of years, see the thing about being a TV/CD is that you will always be a TV/CD. No matter how straight you try to act, how many times...
This is a true story that I would like to share, and happened during a holiday trip to the beautiful country of Philippines, 4 years ago. A group of four friends and myself, decided to spent a week at a resort near Cebu city. The guys were talking about the crazy nightlife,and how they wanted to meet local girls and get hammered. I mostly wanted a peaceful few days next to a pool bar. I had the luck to hadhad extensive holidays in my time, as I was mostly working at resorts around the med for...
A Transvestite Autobiography I've had a number of questions and responses and thought someone should write why they do this cross dressing stuff. So if I may, I'd like to tell readers of my sad tale. I come from a large Catholic family, five brothers and two sisters, and I'm right in the middle. At an early age, one of my older brothers told me that my parents didn't want me; they were trying for a girl. I don't know if he told that to my younger brother, but he's so messed up...
TRANSVESTITE CAUGHT by R.J.D. & "c.c." Like a lot of men, I've always been fascinated by Lesbians. I would often go down to the Times Square Bookstores and go through rack after rack of those magazines that feature models in simulated lesbian poses, and I'd get a charge out of it every time, often returning to my plush apartment with stacks of magazines, paperback books and videos to keep me entertained. I don't know just what it is that has always turned me on about the idea of...
Chapter 1 It was late Friday afternoon and I sat behind my desk smoking a cigarette, leaning back in my chair with my high-heels resting on yesterday's newspaper. I contemplated my red-painted toenails through the gauzy nylon of my fully-fashioned stockings. They were overdue for a touch-up, and so was I. The fading light feebly outlined the sign painted on the glass panel of my office door. It read: ycnegA evitceteD etavirP- snolyN elehciM. A shadow darkened the glass panel and I leaned...
I have been cruising since I was a teenager. As I got into my 20's I became more adventurous and began wearing women's underwear underneath my male clothes.Some men I met loved it, others didn't.Online one day I chatted to a transvestite who agreed to meet me fully dressed that evening in a toilet in a country park. I went at the agreed time but to my shame I really did not think it was seriously going to happen. I just could not picture someone taking such a risk with a stranger.When I pulled...
The Reluctant Transvestite By Pippa HighHeels [email protected] Synopsis: James Miller has a secret vice. He loves it and hates it at the same time; he revels in his perversity and is ashamed of it all and it's implications. He finally gets an exciting lifeline, then the professional help of a trained psychologist. But all is very far from what it seems... [James Hillman, a psychologist, wrote: "Loving oneself is no easy matter, because it means loving all of oneself,...
Transvixen By Michele Nylons Chapter Two: Transvixen begins "No fucking way!" Panti and Cherri shrieked in unison. They were sitting at the kitchen table opposite Wendy. "Look! Here's the fucking bottom line." Wendy pointed to a bunch of figures on a spreadsheet. "Vixen is losing money. If I can't get you decent venues and crowds you might as well break up the band right now," Wendy explained. "Before you say definitely no, listen to my plan," she went on. "The band...
Chapter One: The First Meeting Preface. This is a full account by David, a closet submissive mature bisexual male transvestite of the first meeting with a mature bisexual assertive male she met online via Skype video chat by the name of Geoff. By day David, 45, 5ft 8, bald under the wig, not fat, but not skinny, is a quiet unassuming post office worker, at night and weekends he transforms into a very classy Transvestite called "Jak" The meeting is set for Friday evening, it is...
What a time to be me Seeing my reflection in the mirror Reminding myself That IS me Would my sisters mind Trying on everything of theirs so fine Would they pitch a fit and rankle With me learning to walk in their heels and try to not break an ankle So many times before Dressed in their clothes I adore Trying to copy their looks as a cool hip chick Even as I apply their lipstick How satisfying it was to me The look on their faces When I stepped out of my room To present to...
Why Some Men Prefer Transvestites by Michele Nylons Copyright© 2009 by Michele Nylons Introduction To set the scene, I am a middle-aged, married, businessman who also happens to be a part time transvestite. That is I like to dress like a woman and experience sex with men, other transvestites, crossdressers and women. I do NOT want to be woman, I don't stay dressed as a woman all day every day, nor am I interested in sex with men unless I am dressed as a woman. I used to...
Introduction To set the scene, I am a middle-aged, married, businessman who also happens to be a part time transvestite. That is I like to dress like a woman and experience sex with men, other transvestites, crossdressers and women. I do NOT want to be woman, I don't stay dressed as a woman all day every day, nor am I interested in sex with men unless I am dressed as a woman. I used to consider myself a 'crossdresser' until a few years ago. To explain; that means I used to dress in female...
This is the last part of my true story. I had expected it only to need two parts, but it seems that I'm quite a wordy writer, so it now spans 3 parts.Where did I leave off last time? Oh yes; Toni, the gorgeous Brazilian TV was leaning forwards, dressed in her black lingerie, her firm arse towards me, ready for me to enter her. Read on...I wasn't expecting this to go well, as I'd only had a little anal sex before, with a woman, and this had been on a bed, where I could jockey around for best...
This is the last part of my true story. I had expected it only to need two parts, but it seems that I'm quite a wordy writer, so it now spans 3 parts.Where did I leave off last time? Oh yes; Toni, the gorgeous Brazilian TV was leaning forwards, dressed in her black lingerie, her firm arse towards me, ready for me to enter her. Read on...I wasn't expecting this to go well, as I'd only had a little anal sex before, with a woman, and this had been on a bed, where I could jockey around for best...
I have always enjoyed cross dressing, and in the few years I have been divorced, I have been lucky enough to dress whenever I pleased, but at 6, 2" and 15 1/2 stone, I'm never going to pass as a girl. If you see my favourite videos on my profile, you'll notice that quite a few are transvestites fucking guys, and this is something I have always wanted to do, but the opportunity has never arisen....until last weekI was in Amsterdam on a business trip, and was supposed to fly in and back in a day....
Transvixen By Michele Nylons Chapter Six: Bliss Michelle Murphy studied Tony Carlotta carefully as she sipped her Chateau Lafleur 1982. Only the best for Tony. He was a big man for sure but he carried his weight well distributed on his large frame. In his dark Italian-cut, hand-crafted suit he looked distinguished and projected an aura of wealth and power. To put it crudely; he looked like someone you didn't fuck with both physically and professionally. His head was large...
OK this is the second part of my true story. I think I'd best point out that beyond the (I'm told) common early sexual experiences most straight men have as youngsters, with other men of their age, I'd not had any experience of men. You won't, of course, get many straight men who admit to this. But I'm not like most men.However, this early experience was enough to leave me curious as to what it would be like to have fun with a cock. As you may have read in part one of this story, I was rapidly...
OK this is the second part of my true story. I was going to leave it at two parts, but I think there's enough to make it three parts, now!I think I'd best point out that beyond the (I'm told) common early sexual experiences most straight men have as youngsters, with other men of their age, I'd not had any experience of men. You won't, of course, get many straight men who admit to this. But I'm not like most men.However, this early experience was enough to leave me curious as to what it would...
As I laid back against the wall of the toilet with my nylon-clad thighs spread wide and my erect cock jutting up lewdly from between them, the wooden door in front of me slowly opened to admit the guy from the stall next to mine. “Oh yessss!” the guy hissed quietly, slowly wanking his rigid cock and bolting the door behind him as he took in the erotic sight of me lying back in front of him, me now totally exposing my sexy undies to his gaze, “That’s nice very...
As I lazily drove along in the evening’s dim light and looked down at the hem of my black PVC mini-skirt, I saw that as I passed under the orange glow of the street-lights, the knob-end of my semi-hard cock, my black suspenders and my stocking-tops were plainly visible between my nylon-clad thighs! I seldom if ever wear panties or briefs preferring to let my cock and balls dangle naked and unhindered underneath a short skirt or dress. Maybe I should explain right here and now that...
Confessions of a transvestite hooker or whore – you cannot be serious I hear you cry – well I am as I reflect on my life in dresses to date and some of my experiences which I am about to write about here as a memoirs of a life in dresses.So why use the term ‘hooker’ or ‘whore’ – well what I am about to relate from my current stage of life the memories are that upon reflection the meets I am about to relate felt more like me being a provider of sexual services and pleasure to people desperate...