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my life as a sissy crossdresser

it should be noted that i did not ask for this disposition to crossdress, rather it was presented to me quite by accident. circa 1958...grade school PTA fashion show. PTA fathers were asked to put on a fashion show dressed as their better halves. my dad was right in the mix. I remember he wore some mid calf, grey business suit w/jacket, tan stockings and black heels. i remember this because he practiced dressing days before the show. he wore some makeup and a wig. not very passable, but not...

Pamala s first adventure

I joined the army after I quit school in the 12 th grade. After joining the army it put a crimp in my dressing up as a girl. I did wear panties whenever I got the chance but I really wanted to dress up completely as a girl. I wanted to go out dressed and I have to admit I was attracted to several guys in my unit. My third year in the army I went to Viet Nam in December 1967. I was in the 101 st Airborne. I had a best friend in my unit and we were friends since we were both assigned to the...

Not just another day dressing up as Gemma

Not just another day dressing up as Gemma Marks and Spencer is a wonderful shop. Their gorgeous lingerie is worn by so many women. They sell some wonderful dresses, skirts and blouses too. I often wear their women's clothes and derive a huge amount of pleasure from doing so. That paragraph could have been written by thousands of women living in the UK, however I'm not a woman. My name is Gemma and I'm a Transvestite or if you like, A Crossdresser. I'd even own up to being something...

A Young Crossdressers Beginnings

( . Y . )I just found out my Mom told a whole group of parents about an incident when she caught me in her cloths. Specifically, she caught me in her bra, panties, panty hose, and makeup. I am approaching thirty-five years old now and the individual that told me must have heard it from his mother, who was one of the other parents. We used to go camping every year and one night when the k**s were playing or sleeping the parents were talking. She let it slip that she caught me in her room with...

Dan Becomes Dawn

Chapter One: The InvitationI work from home and am able to dress enfemme most days.Today I am wearing a pink flower-pattern, button front blouse, knee-length white a-line skirt, a pair of white walking sandals with a wavy, medium brown wig and clip-on earrings. Under that I am wearing a corset to flatten my gut, matching white lace panties and underwire 40-D bra to support adhesive-attached breast forms, which give me a comfortable bosom.I had just received a call from an investment group...

Terry Gets It In The End

The converted attic was my room and it gave me loads of privacy. So as I grew up I could wear the clothes I liked, as long as I stayed in my room. By the time I was a senior in high school, I kept my toe nails painted all the time and I wore panties every day. At night I wore frilly little night gowns and more likely than not I would masturbate, always fantasizing that I was the girl and some faceless guy was fucking the shit out of me. I learned to dance and I loved the way my skirt flew up...

Adventure in St Louis

A NIGHT IN ST. LOUIS Work can really suck. At this moment I am sitting on an airplane wrapping up a three day business trip. Thank goodness I know how to make work fun. If someone gives you lemons, I say make lemon meringue pie, because lemonade is not good enough. What I am getting at is you have to make the most fun in your life, because life is too short. If you have a passion, make the most of it and enjoy your passion. My passion I have to keep hidden most of the time, but when I travel...

Dawn And Patti Move To Denver Part Three

Part Three: A New HomeAt one-thirty, we left for the title company offices. First American Title Company was located less than two miles from the hotel, and the same distance from our new home. Teresa met us in the lobby.“Thank you for inviting Laura and me to the inaugural party tomorrow. I understand Andrew and Marie, as well as Harry and Jean, will also be there. We look forward to the evening. It should be a fun time. Let us get you the keys to your new home!”Teresa led us into the title...

Crossdressed In Best Friend rsquo s Mom rsquo s Clothes 8

I arrived at my step dad's place and paid the cab driver, plus tips. My body was shaking with nervousness and found myself in doubt if I should do this. I got in the elevator and pressed ‘4’. I held my bottle of ‘Pink’ firmly in my hands and the elevator stopped and opened.I walked down the hallway to Steve's front door. Breathe in and breathe out. I rang the doorbell and I was just gonna tell him that ‘It is me, Brian’. But then, the thought of me sucking his cock and everything that happened...

Jaime s Way part 3

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

Jaime s Way Part 3

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

Crossedressed In best friends mom clothes 20

Part 20We stepped out of the car and inside. Such an old yet classy place. Noah came with the suitcase. Lauren was talking to the receptionist and was handed 2 keycards. She turned around and gave me one.“Here, Caroline. The room number is on the card. Do what you like. I need to go with Jonas and Noah to their tuning factory to check up on some things. It's very important that this racing deal goes smoothly. So don't wait up for me!”I nodded “Ok miss. What about your suitcase?”“Take it into...

My Foggy Late Night Story

It was a cold, wet December night. Here I was in my room, feeling exhausted, and laying on my bed doing the whole Netflix and chill thing. I had just pulled a long afternoon and evening event with my college study group. We spent the day as total masochists painfully cramming whatever we could into our tired brains for our finals. It had worn me out so much that I didn’t want to do anything, including exercising, which was another problem I had to deal with since I hadn't exercised in nearly a...

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...

From the Bookstore to the Bedroom

Some of my stories are true, or at least, based on actual experiences. Others are complete fantasy. This one starts with an actual experience and turns into a fantasy of how I wish it would end. I never get as much “gurl time” as I would like. It seems when I dress, the time flies by too fast. So, when I get the rare opportunity to get away from my captive male life for more than the usual few hours, I make the best of it. In this case, taking the hours required for a complete transition...

Pleasures at Dressing Manor

Pleasures at Dressing Manor - part 6 of 7 The story so far: Young teacher Miles Johnson receives a letter from his pupil, Lyndon Blonding, 18, telling how his spiteful stepmother is keeping him prisoner and dressing him childishly. He takes the letter to his Headmistress, Alison Forceman, who secretly feeds Miles the feminizing drug Fem-Agra, so that he becomes addicted to girls' clothing and suffers embarrassing changes to his body, before accompanying him in his bid to rescue the...

Crossdress Sex 8211 Mami Fucks Using Strapon

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

Georgina s First Steps

Mary and Linda met at primary school, became best friends, and supported each other as they grew to womanhood. Both married at twenty. Mary's daughter Julie was born a year later, and I followed within a few months. For both of us, the first few years were a blissful blur of happy families. Sadly, this idyll changed when Julie’s Dad, soon to be followed by my own, succumbed to the wanderlust, and sought out pastures or at least lady gardens new. Life was now hard for the single mums, but they...

The Yellow Sundress Ch 04 Observation

The Yellow Sundress © Titania Midsummer - 2016 Chapter 4 - Observation Adam did not return the next day, though he did drop a note into her letter-box saying he would be a few days. He had to give notice to his landlady and to the restaurant manager. He wrote that as casual staff are easily found he would be under no further obligation after three days. Judy was a little disappointed, but at least he was doing the right thing which boded well for their future...

Cindy s makeover

I would like to share my latest cross-dressing experience. Like many cross-dressers, I dress up part-time. I am married and my wife does not know of my fetish of warning woman clothing. My dressing need stems from my enjoyment to the attention I received from admires. I am new at this cross-dressing having only started dressing five years ago. Many cross-dressers started their fetish when they were young, preteen or in their teens. As a cross-dresser, I now pay more attention to woman's...

A Night of Firsts

I have been crossdressing in private since I was young. Now in my late forties and after three failed marriages, I had decided to step outside as Jessica.So after a lot of planning over several months, the day had finally come.I stepped in the bath as JD and shaved any hairs on my body that should not be there. It did not take long as I had been preparing my body for weeks to be smooth. I stepped out of the bath as Jessica and dried myself off. I wrapped the towel around myself just like any...

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...

Chris s First Oral Experience

My name is Christopher, I’m twenty-eight years old, and have my own apartment. I work for a company which furnishes custom programs for businesses. We build the programs in our office, then some of us have to go to the customer to implement it, train their employees, then monitor it for a few weeks to assure it operates properly.While we’re at the customers, we look for improvements that can be made so we can expand the program, increasing our charges to them. This starts a cycle of going back...

Little and Strong

Authors Note: One of the many traditions in the British legal system is that in the law offices, often called chambers, the male lawyers are always addressed as sir by the support staff and the female lawyers, irrespective of whether they are married or not, are addressed as Miss. The Dinnie Stones mentioned in the story are real. You can view a very strong woman lifting them on YouTube https://www.youtube.com/watch?v=RWbZTzMtw1E Little and Strong The Interview Jamie Evans...

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,...

My Qualifications to Write About Crossdressing

My Qualifications to Write About Crossdressing By Ricky How ironic! While looking for something in my files the other day I found I have been writing about crossdressing more than 10 years now. The problem is, I now realize I am completely unqualified to be a crossdresser, let alone a writer on the subject. Think about it, just what are the qualifications for a crossdresser? Surely you've read a multitude of "true life stories" in the crossdressing magazines. Perhaps if we...

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...

All Dressed Up

All Dressed Up by Pat T. Being a dominant woman, I'm naturally attracted to passive men. I like to wear the pants, so to speak, and love to bend males to my whims. Several months ago I was having a drink after work when I noticed a man from the office staring at my shoes. They were my highest heels, about 5", and were made of sparkling red patent leather. They were darned uncomfortable, but I put up with them because they were outrageously sexy. I shifted my weight to give...

Pleasures at Dressing Manor 3

Chapter 3. Mr Johnson to the Rescue The story so far: Vera Hidebotham is set on taking revenge on her runaway new husband by desexing his18-year-old son, Lyndon Blonding. She feeds him a feminising agent, Fem-Agra, which alters his gender and gives him an urgent appetite for girlish dresses, enabling her to torment the youth through his fetish desires. The boy smuggles a letter pleading for help to his school teacher, Miles Johnson, who is horrified at the boy's treatment at the...

The Change Up

Finally a break comes my way. The children are off to college, the wife has to go out of the country for two months on business. I can’t remember the last time we had sex. She used to dress in all types of lingerie for me. It helped me suppress some of my crossdressing desires. That stopped and my crossdressing started to grow again. What an opportunity for me, I can change up and dress the entire time except for when I have to go to the office. Lucky me, most times I work from home. Sunday, my...

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...

WoMen In Red

WoMen in red Writen by: Julian069 1. Part. Julian is caught by 4 women in his penchant for women's clothing and forced to become a Dolly. 2. Part. Julian's wife gambles Julian's self-determination, both of them get into slave service. 3. Part. Julian takes on his role as a woman, experiences erotic adventures, but also finds an explanation for his passion. Part 1: I am male, my name is Julian, live in Berlin Germany, I am 44 years old, 178 tall, weigh 70 kg, happily married,...

The Dress Shop Part Two

CHAPTER FIVE TRAINING WEEKEND We started Saturday with another failed attempt at love making. Within about 30 seconds of Beth playing with my penis, I gave in and orgasmed. I wasn't even erect, but just the sight of my beautiful, stunning girlfriend playing with me was enough to tip me over the edge. Once again, like last night, there was no evident frustration from Beth. Only embarrassment from me. "Awwww. Such a pretty penis!", Beth remarked, grinning and playing with it in...

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...

Xdresser Roxxi s black cock obsession Part 1

This is only a fantasy of mine at the moment however I hope one day it comes true .For a long time now I have been going to hotels and dressing up spending the night wearing various sexy outfits .Taking pictures of myself fantasizing about being a girl and what type of guys I would like and what I want them to do to me .After years of doing this I have worked out what really turns me on and off, this story is my fav fantasy .I'm very submissive when I dress up as a girl ,i want to be man...

Xdresser Roxxi s black cock obsession Part 1

This is only a fantasy of mine at the moment however I hope one day it comes true .For a long time now I have been going to hotels and dressing up spending the night wearing various sexy outfits .Taking pictures of myself fantasizing about being a girl and what type of guys I would like and what I want them to do to me .After years of doing this I have worked out what really turns me on and off, this story is my fav fantasy .I'm very submissive when I dress up as a girl ,i want to be man...

Consequences of Cross Dressing

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

Double dildo Please

In my mind, there are two types of closeted cross-dressers. One dresses strictly for themselves in the confines of their home or other completely private area. The second, ventures out into public or semi-public for the thrill of being dressed as a woman in front of others, but still keep their cross-dressing a secret from those who know them. Many in the second category, also engage in sexual activity. I fall in the enhanced second category. However, due to limited time and resources, my...

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...

Paris Sex Extreme

Seated in the famous Champagne Bar of the Euorstar Terminal at London's St Pancras Station, Nick toyed with his champagne flute. With one eye on the giant overhead clock, he was getting anxious about the departure of the Paris train. Then he saw Cathy approaching. She looked stunning, turning several heads as she alighted from the escalator. She was wearing a long-sleeved double-breasted cerise suede jacket, nipped tight at the waist and flared out in pleats over her hips, the shortest-possible...

Looking for Tess Dressed just So

Looking for Tess, Dressed just So by MadQuill Please remember this is a copyrighted work and all legal disclaimers apply. This story is a subtly revised version of the story "Dressed So". The intent is a response to a comment from a reader. She suggested that the story "belongs in the Lesbian category. I arrived here from a 'stories like this reference'. I found myself captivated by your series that was romantic, with character development, and quite different; re: lesbian and...

Noodles Part 7

Lori is coming back home tonight, I had to remind myself. Mark and I slept together last night, then I had to tell him goodbye this morning. That was a bittersweet ending to an amazing weekend. I washed all the laundry and sheets, putting everything back the way it was before my wife went out of town. I hadn't heard anything from Mark since he left this morning. That's probably for the best anyway, I reasoned. I need to get my head right and remember my masculine identity. Lori will be...

Wedding Dress Surprise

Wedding Dress Surprise At last Jack's wedding dress from Ebay had arrived and he could play dressups as a bride. But when he takes a walk in the garden things take an unexpected turn - for the good. I stood there staring at the package. I had been waiting weeks for the delivery after ordering it from eBay. I had taken a chance and told them I was male, so when they made it from my measurements it would be the right shape perfectly for my body. For my measurements I had...

Sharon Goes The Distance

When I woke up Saturday morning, I knew it would be a very eventful day. My wife, Donna, had been making plans for quite some time, which included me dressing up as Sharon, my female alter ego. Three years ago, I had confessed to Donna my desire to wear feminine attire from time to time and she had embraced it more than I could ever imagine. In fact, she took pictures of me all dressed up or even while she fucked me with her large strap on dildo. We posted these photos on a free, picture...

Dressed Just So

Dressed Just So by MadQuill As evening approached I entered my dressing room and set the glass of Chardonnay on the bureau. I had planned to wear a simple black dress but decided a white V-neck with a fitted waist and open back would look best. Due to a hectic work schedule I'd lost nearly two kilos over the past two weeks and decided to enjoy the slimness. This mild winter allowed some freedom from the boots and long sleeves and a sheer nude pair of hose would suffice. I selected...

Crossdress swaps clothes and gets assfucked in pub

A few years ago I was on a weekend trip to Brussels and Amsterdam with some friends, and found out a girl I knew from Ukraine was now living in Lille, not so far away, so I decided to make a quick trip to see her the evening before we were due to fly home. I caught the train from Brussels to Lille and she and her boyfriend picked me up at the station. She was a short, curvy blonde, with equally large breasts and ass. She loved wearing sexy outfits which showed them off. This evening she was...

Caught

It seemed to Ken that time had slowed down to a snails pace as he watched the events unfold before him. The door to his sister's bedroom seemed to take forever to open and for Connie to step inside. Connie's head was down as she placed something in her purse before it rose up. That act also seemed to take forever as did her eyes growing wide as she took in the scene in front of her.Ken could blame no one but himself as had been pushing his luck as of late, but never imagined that he would...

Sidedressing

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

Cross Dressing Cock Slut Party

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

Wet Dreams to Crossdressing

Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I started out as a young teen as a panty fantasizer and have progressed to where I am today. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a f****y. But, I have evolved to a cock sucking crossdresser. I’m writing to try to...

Becoming Anthea

My name is Anthony and I am twenty-two years old. I have extra-long dark hair and darker eyes. I tie my hair into a ponytail and have a close trimmed beard. I look handsome and enjoy keeping myself in shape. I am a lucky guy as I have a very sexy girlfriend who is two years older than me. Zoe and I met at a mutual friend’s party and hit it off right away. She has short blonde hair and blue eyes. Her small beautiful mouth sits beneath a cute button nose. All in all, Zoe is a goddess and I love...

Teenage CD Awakening Part II

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

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...

Pledging Tau Geta Delta Part 1 Dressing Up

Pledging Tau Geta Delta - Part 1 - Dressing Up By Farleven "You're never going to get in." Max laughed as I looked over towards fraternity row. All of the frats were lined up there, one stately building after another. All of those opportunities hiding behind brick walls and Greek columns. "Well, at least I'm going to try," I replied. When I'd started at the University I laughed at the whole fraternity thing like a lot of people. It all seemed too chummy, and I wasn't a wild partier....

Tennis

Sandra and I had been going out together for about six months. She was the perfect looking girl for me, with her beautiful freckled face, slim turned-up nose, pouty red lips, light green eyes, long blonde hair that she usually kept in a ponytail or braids, a great body topped with perky B-cup tits, and a cute firm ass that just screamed to be pumped. She was only 23, but Sandra already knew what she wanted out of life, and wasn’t afraid to go for it. She had met her latest acquaintance at the...

The Sexy Girl Next Door Part Two

Once a girl gets a big hard cock in her, there is no stopping her from wanting another one in her. At least, that's how it was for me after my first fuck with my neighbor, Ben. He had just fucked me with his twelve inch cock, with a big head on it and I loved it so much I couldn't wait to do it again. Our friendship was growing like our dicks were. And I was now having an affair with my next-door neighbor, who wanted to have threesomes with me and his wife, Jennifer. Being a sixteen-year-old...

Pleasures at Dressing Manor

Pleasures at Dressing Manor - part 1 of 7 Chapter 1: Who can help poor Lyndon Blonding? Dear Mr Johnson, I am writing this letter to tell you about my stepmother, Vera, and how she has kept me away from school for the past two weeks. I am not allowed out of the house; in fact I am imprisoned in my bedroom with the door and windows locked. Not only that, sir, but my stepmother has taken away all my clothes. I have to wear a little short sleeved white shirt and pale green...

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...

What Happened After Police Arrest

Hi.I am now a mature gay crossdresser.A bit of history of my life as a crossdresser.I have been gay for as long as I can remember. I have always lusted after men. As with most crossdressers, I have tried to be (normal) but have always returned.I even got married and still am officially. Very rarely did I get hard for sex and was often punished for my failure, ordered to lick her out. I only enjoyed the punishment and luckily, she found sex elsewhere.Many encounters leading to my first anal and...

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...

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...

Vicky s First Time

I was very open about crossdressing when I met my wife when we were in our 20s. She has been very supportive and helpful. She helps me with my hair, makeup, and picking outfits. We started having sex with me dressed up as Vicky. This soon escalated to her taking me with a strap on. I loved the times she would fuck my ass with her cock. I had never considered myself gay or bisexual but the feeling of her cock inside me opened up the possibility for more.One Thursday she told me that we were...

Chronicles With Sexy Crossdressers

My email id is Do not forget to let me know how this sex story was. Who knows, we might get even lucky if everything goes well ;) Clean shaved men inside female clothes (or people who are known by the name crossdressers) are my new found favorites. Believe me, I always make it a point to taste every bit of them with passion and fire. My hands and tongue never leave an inch of their body. Hairless, like women and the ‘EXTRA’ jackpot called ‘COCK’, is simply divine. This is a story of how a...

Crossdresser and driving

A little about me, I'm married, and wife doesn't have a clue I like to dress up. I would love to have her know and accept it, but I don't think she would. I do cam and love to get instructions from people that are watching on cam. Am I a sub? I think I am. I like to drive dressed. When I take a drive up to northern Wisconsin, I love to drive while dressed. It is always around 5 am when I leave a little dark but getting light. I can't get dressed at home and walk out to my vehicle. I don't have...

The Green Dress

The Green Dress A man buys a dress for himself ... and then pays for it. Note: the first half of this story is true. The second half I alternately wish and dread will come true. Part 1 "Can I help you find anything?" the salesgirl said. I was standing at a sale rack in a women's wear store. The salesgirl was a young girl in her late teens or early twenties. She's pretty cute, I thought reflexively. For a moment, I froze. Was I really going to go through with...

Brianna and Jayden Episode 2 a TG Dress Shop Story

Brianna and Jayden, Episode 2 a TG Dress Shop Story Read my previous short solo "Brianna and Jayden - A TG Dress Shop Story" from 2015 for the back story. Reviewers asked for a continuation, but my mind has been away from fiction writing. In the last two years society has changed and Jayden has learned a great deal about herself. She is excited to talk again with Brianna. Let's listen in as they come to closure. ___________ "Hi, Brianna, recognize me?" A short, slender, smooth...

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...

Deja Vu AscendancyChapter 65 The Best Dress I Have Ever Seen in My Life

Saturday, April 16, 2005 (Continued) We saw Cindy's car arrive as close to 7pm as made no difference, making me suspect that Julia had been specific in her instructions. Cindy walked up the path carrying something fairly large and reflective, although I couldn't see much of it. I opened the door as she neared it, and she walked right in. The mystery of the object was quickly solved. It was my HUGE first place trophy. The damned thing was big enough to mount in the front yard with a...

The Compromise Part 1

My wife, Ally, and I have been married for eight years. What once could be considered a torrid love affair had subsequently lost its sexual passion. We don’t have any children, both being career focused, but our sex life had become quite stagnant from the steady grind of life and over-familiarity we had with one another’s sexual tastes. That is, until one crazy night changed everything. About one year ago, we were fighting constantly. We didn’t know why, but we were both at our wits end with...

The summer of dresses skirts stockings and high heels Part 2

My mother had a huge smile on her face. A look of passion and excitement in her eyes, as she got up from the couch. She walked over to me, extended her hand to assist me in getting up from the chair. I was mesmerized by her eye makeup and lipstick. We momentarily locked eyes. I began to feel chills running up and down my spine. The same chills that I felt for Christine in my French class. I ashamedly looked away. But that was not done quickly enough. My mother immediately understood my...

Miss Pink Part 4 The Dress Code

ONE When I got home I closed and locked the door and immediately headed for the bathroom. I undressed, calmly at first, but then panicking and fumbling with my bra and the hooks of the suspender belt. I had to get out of these clothes! Finally naked, I collapsed to my knees and vomited in the toilet. What had I done? Kat's cheer-leader game had rippled out with massive unforeseen consequences. I heaved and cried, wondering how I could let myself be violated as I had today. And...

Crossedressed In best friends mom clothes 24

Part 24We took the elevator down to the parking garage and drove off in my pretty pink Rolls Royce.“Where are we going, Caroline?”We drove to the city where I knew there was this shop with all kinds of Victorian and l****a dresses.“First, we need to get your nails done, so we need to find a salon! I know there is one in the mall. So let’s start there!”He looked at me a bit frightened. “No...I can't! I'm in pantyhose and panties! I refuse!”I parked the car outside the mall and stepped out, but...

An Unforgettable Halloween

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

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,...

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...

Seven Years a Woman

Seven Years a Woman Holly Sharp Seven years ago, Shane Turner became a wanted man. Losing his balaclava during a bank robbery led to him becoming the subject of a relentless nation-wide manhunt. With every police officer in the country chasing him and with a substantial bounty on his head, Turner did the only thing he could do: hide. For seven years, this man has hidden himself away in the last place anyone would ever think to look: under the makeup of a woman named Bonnie...

Crossdressing Porn Story 2

Jack let himself in the front door. It had been a long day at the store. He’d noticed Ray’s Porsche in the garage. “Honey, I’m home.” From the kitchen came a sweet “Hi Janice how was your day.” “Pretty rough.” “Well just sit down on the couch and relax. I’ll have dinner ready in jiff.” They had divided up the house chores and Jack was glad that Ray had taken over the cooking. The meals were always delicious. Ray walked in...

The Bodysuit

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

Glimpses of Consequences

GLIMPSES OF CONSEQUENCESBy DrBill"HOWA we going to start?" The ritual joke having been followed by the ritual groans, the Housewives of Worthington Acres came to order. The group had evolved from informal visits for coffee and complaining to a neighborhood organization of sorts. While the meetings still tended to be primarily boast and bitch sessions, they also traded useful information and occasionally took on neighborhood improvement projects and the like. But they did not try to pretend that...

A boy s femininity awakened Part two early girlhood

Sissy boy John was petticoated at Secondary School after falling foul of Jenny Tough, a school bully. During his week of penance, John found that he was more at ease and happier amongst girls than with boys. John decided, therefore, to explore his feminine side by trying to live as a girl. John’s Mum was shocked when he first arrived at home wearing a schoolgirl’s uniform but calmly listened to his story.“Well, sweetie, this is a bombshell. You’ve always been a sensitive boy, but I never...

Sissy Blane and the Hydraulic Inevitable

The story so far: debt-ridden Sissy Blane's first obligatory date with Mr. Plumrose is about to take place. '...there's nothing good or bad, but thinking makes it so.' The truth of the old saying occurred to me as I awoke on the fateful Friday and was surprised to discover that I was looking forward to the events of the coming evening.Arising from my bed feeling energized I bounced downstairs to make a breakfast of oatmeal and raisins and some french-press coffee. I decided that would be it,...

The Halloween Crosdressing Mistake

The Halloween Crossdressing Mistake My wife Stacy and I were standing in a room with about 30 other people. The room, was one of those fancy ballrooms that you only find in old universities, or houses that were owned by people with entirely too much money. I mean really, who has the extra money just lying around to build a ballroom!? You can use these things what, four times a year if you are lucky? Well, I digress. So we are standing there in this ballroom, at what is...

The Red Dress part 1

The Red Dress - Part 1 Final installment in the adventures of a husband who buys himself a dress. Husband comes out for a charity event, wearing a red dress of course. A few months ago, my wife caught me after I secretly purchased a dress for myself. Since that fateful day, I've steadily slipped deeper and deeper into feminimity, all at the hands of my wife, Ann, and her wickedly inventive best friend, Susie. Since our casino adventure, the three of us spent more time...

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...

Dan Becomes Dawn Chapters Twelve Twenty

Chapter Twelve: Time For WorkI woke on Monday morning while still snuggled with Patti.Getting out of bed, trying to not disturb her, I went to the bathroom and removed my nightie and g-string. First, I gently peeled my breast forms off then showered, dried, and shaved. I rubbed some body lotion on my chest to soothe the effects of the adhesive. Getting dressed, I put on white lace panties, then khaki trousers and a polo shirt, with socks and hiking shoes. I took nail polish remover and cleaned...

Confession and testament of a crossdresser

Italy, september 2011. Sorry for bad english, I try to write correctly but don't know if I did. From tonight, I was a crossdresser. I'm been crossdresser from 12 to one day before my 27th birthday. Irony. I begin to have an answer to the question: "What feel girl?" Yes, a simple question. What feel girl when wear panty, tights, dress, skirt? What feel a woman in heels, purse, with her hair falling down the shoulder? What feel a teenage when begin to make up herself? When wear lipstick,...

A Condition of Endearment

I am a young, petite, passable and enthusiastic transvestite. I’ve been crossdressing and working on improving my look and appearance ever since I was a sixteen year old boy. Now after two years of weekends dressed in public as Cari, I had developed quite an attractive look and appearance. It often seemed at times, that many a man would come my way.Because of my exotic and sexy appearance, things could get interesting at times. When you are dressed as an alluring, sensual woman in high heels,...

My Sexual Odyssey Part 2 Becoming a Slut

After having had a few experiences, I became slightly more comfortable with my sexuality. I decided to branch out a bit, and see what life had to offer. I wondered whether there were any bars or clubs that I could go to to meet people who were looking for someone like me, so I went online and discovered, that yes, there were quite a few such places. It is so wonderful having the internet at times like these; I have no idea how I would have learned about these things without being able to go...

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...

The Feminisation of Michael Chapter 3

The Feminisation of Michael. Chapter 3 I endured the rest of the afternoon with continued suppressed sniggers and laughter. I was glad when 5.00pm came and I buttoned up my jacket and put my handbag over my shoulder and left with a big sigh of relief. Sue was waiting outside in the car. “Hi Michaela,” she greeted me. “How did it go honey?” she beamed. “Fucking awful!” I blurted out. I was close to tears. “Just drive!” “I hear they put you on that secretarial course honey. That will be better I...

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...

Diapers Dresses and Domination

Diapers, Dresses, and Domination Or How in the heck did this happen to me? By Missy Satinpanties It started simply. I was fairly young, and a very successful stock broker. Thanks to some luck, a few shrewd guesses, and the guts to take a real risk, I was now sitting on a rather sizable nest egg, owned a nice house outright, and a beautiful Black Lexus. Nothing...

Ethan s Prom Dress

Ethan, like a lot of teenagers was subconscious about his body, although he did have more reasons than most boys as he suffered from a form of gynecomastia, a condition that gave him perfectly formed, feminine breasts. He also secretly wishes to wear skirts and dresses, which would be a perfect combination if he wasn't too embarrassed by both his body and his desire to follow through with this idea. So instead he bandages his chest flat each morning and desperately tries to hide all of...

Next Time I ll Wear the Dress

Next Time I'll Wear the Dress I was shoving paper around on my desk keeping half an eye on the clock waiting for lunch to come around. I had a date that I was really looking forward to. Doris and I had been friends a long time ago but hadn't been in touch for a while. We ran into each other over the weekend and decided it was time to meet up for some long lost conversation. Beep! Beep! Beep! The phone on my desk alerted me to an incoming call. I snatched the receiver from the...

Pleasures at Dressing Manor part 7

Pleasures at Dressing Manor - by PRIM The story so far: Young teacher Miles Johnson has tried his best to rescue his pupil, Lyndon Blonding, 18, from the sissifying plans of his spiteful stepmother, Vera Hidebotham, who aims to turn her stepson into a girl. His Headmistress, Alison Forceman, accompanied the young teacher to the boy's home, Dressing Manor, outwardly to help him but secretly in league with Vera. The two males have been fed the feminizing drug Fem-Agra,...

Room 209 First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – braI've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight...

Night Out Ch 5 Shopping Spree

June's heart was racing; he visibly shook. Sweaty palms, nervous demeanor, he may as well be a dealer based on his level of suspicion–he'd just be noted as a bad one.The bag he carried felt heavy despite not holding anything of significant weight. Its contents may as well equate to a full ton due to the knowledge of what was inside.It was crazy to think a few moments ago this very man was imagining bending Evy over the next sturdy object he could see. Their games of teasing each other after...

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