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Andrew to Andrea Part One

Hi, I'm Andrew; at least I was Andrew full time until about a month ago. I have always been fascinated by lingerie: its feel, its appearance, how it just makes a body look that much more sexy. Like most curious types I started young (at sixteen, so not all that young), swiping what I could from my sisters or cousins when I could and squirreling my prizes away until I could find time for them. I will always remember the first time I put a pair of lace panties on; my erection was instantaneous! I...

Webmeets Diary Ch 01

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible.I was nineteen when I found the site. Like most male nineteen year olds, in fact like most males past the start of puberty, I had sex on the brain a lot,...

Halloween

This story is not to be copied or moved to another web site Well here it is Halloween and I have an idea to dress up with my older bro and take the two younger bros out to trick or treat. When the big night came I got some of my sisters things to dress up in. I took all I needed to look just like her with the panties bra and skirt and blouse with a short jacket over it all. I must say so myself that after I was dressed and ready to go I did look just like my sister. I could not believe it I...

A Saturday Afternoon Visit to the Office

I usually work from home as I have a very private place with a wonderful view and Lord knows I’ve put in more than my fair share of office hours over the years. But I do occasionally elect to make visits to the office both during normal office hours and off-hours to make copies, restock my home supplies and have a cup of coffee with a long-term friend or two. Usually when I do hit the office, I find time to spend some me time in the restroom, jerking my cock and fantasizing about taking cock...

The Party

I am a closet cd. It was Halloween. My wife called from work and said she wanted to go to a party at a friends house. It was a costume party. She said she had a costume and I was to wear one as well. What, I don’t have one. Yes you do, your going as a girl. But I’ve never done this. Well you’re going to tonight. No one will care because it’s a costume party so get dressed and make it good. This ran shivers down my spine thinking about it. So I shower and shave very close-everything. Since...

Free Drinks aren t always free

Where is the line that separates having a little fun and taking advantage of someone?I’m not really sure, but if the universe didn’t want me to do this, then it would make it harder to manipulate guys for free drinks.It’s not that I’m a bad person, I think; I’m just a poor college student who dresses up as a woman to get men to buy me drinks. One trip to a thrift store landed me a wig, heels, and a dress; the grocery store had a cheap makeup kit. Online tutorials took care of the rest.It’s...

Realized Fantasies Chapter 1 Exposure

Steve wasn’t sure, but he thought he heard the bathroom door close. He was in the shower and the bathroom fan was running, so he stopped for a moment to listen. Maybe one of the guys came in to use the toilet, he wondered.“Hello?” he said aloud.No reply. It was probably just one of the other guys getting something they’d left in the bathroom, he thought. Steve was one of the last to shower, and the other guys had left a variety of toiletry items at the sink. So he went on showering but hurried...

Belle brings back a girl

Lucy was lazing around in the living room when she heard Belle drunkenly try to scrape the key in the front door's lock. She heard giggling - a second voice. A woman's. Lucy put her tattered copy of Asimov's Second Foundation down on the coffee table and owled the door with interest, her nylon legs sprawled across the arm of the sofa. Lucy and Belle were both avid readers. Between them they made their way through perhaps 8 to 12 books a month. More, when they had no university deadlines or...

Dad Catches Me With His Friend

From an early age like most I started to get a desire to wear womens clothing. I would always take my mom's thing's and put them on and masturbate in them. The feeling was nothing like I have ever felt before. Around the age of 16 I had gotten a job and started buying my own things,lingerie and such with the money I earned from the job. Prior to that,around the age of 13 my mom had left my dad and he struggled to keep his head above water to provide he and I with a good home. Mom left him...

Happy to be Used Pt 5

I was walking gingerly in my heels and panties from the assault my ass had just received. While it likely looked like I was just trying to be more effeminate, my ass hurt so bad it was the only way I could walk.When I reached the front of the store I saw Sir talking to an older man who was behind the counter with him. The man appeared to be in his early sixties. I looked at him and Sir and then opened the gate to walk behind the counter. I strutted towards them all the time realizing the older...

Just For The Taste Of It

Many years ago, before I was the experienced sissy girl I am now, I was living with a man named Jake. Jake took me under his wing. He wanted to help me become as girly as I could be. One of the things that he wanted to get me used to was the taste of cum. I had tasted it before, but only my own and his. Jake wanted to make sure that I was a cum expert.He said to me, “A true sissy will appreciate the taste of a man’s cum in all of its many flavors. When we’re done with our assignments, you will...

My First Encounter

I had been cross dressing for years but only in private. I had also had a thing for bondage for a long time. A couple of years ago, I met two other cross dressers who were into bondage. We had been getting together every couple of months and playing bondage games with each other. We would take turns tying each other up and taking photos and videos. But, it was always clear that the other two were completely straight and nothing sexual would be involved. I was fine with that as I thought that I...

A Meeting of TV Girlfriends Part 1

I spent my day getting ready - shaving all over, showering, and cleaning myself inside too. I gave myself a close shave and then moisturised fully. My outfit was set - black holdups, matching red & black satin bra & knickers (a thong, maybe), black PVC midi skirt (or optional mini-skirt), and a dark lacy blouse. Black patent stiletto heels. Jewellery included rings, bracelet, watch, and earrings. Night-time makeup was decided upon, with smokey eyeshadow too. A quick spritz of...

I become my wife s girlfriend Part II

This day at work was unusually tedious and seemed like it was never going to end. At the beginning I occasionally dropped my boss's cup and the coffee poured on floor, but luckily the cup survived. After this some guy stepped on my toe and caused me much pain, I bent to touch it and suddenly had a feeling like my butthole was cut by the string of thong. Later my boss was very angry all the day, I was nervous too, but only I knew the reason for this. When I finally got home after a long day,...

Roomate

RoommateIt had been a hell of a year with a divorce, a new job that had me traveling more and having to move into shared housing because my ex was sucking my bank account dry. Carl, my roommate, was a decent enough guy. I found the room on dougslist.org and we seemed to be compatible. He was neat without being compulsive about it, was a working student and was not inclined to throw wild parties. I had not been dating thanks to the bad break up, but in the two months I had been living there I...

A Night With Robyn

I met Robyn in one of the chat rooms on Lush Stories. She too was a cross-dresser, but far more committed to it than myself. She was a full-time dresser on hormones and is probably considered a T-girl. It was a strange relationship. We were both gurls constantly looking for cock, yet, at the same time, teasing each other like two lesbians. With so much role-playing and cybersex amongst the multitude of participants in the chat rooms, it is difficult to separate reality and fantasy. I...

Derek and Amy

We're holed up in a nice little hotel room in the middle of nowhere. No one around here knows us and no one will bother us. Tonight's all about us. Once we get settled in I send him off to take a shower. Now that I'm sure he's busy it's time to get to work. Digging out my bag I lay out the outfit I've had prepared for a long time. The panties are black silk, as soft as butter. There's a black garter belt to go over them to help keep up the black stockings. The garters are ones that I've had...

Beyond the bookstore

One day after work at the dinner table, my wife told me her sister was going to have a minor operation. She said she wanted to stay with her a few days after the operation to cook, clean, and take care of her while she was recuperating. “Would you mind? I’ll only be gone from Thursday to Sunday. I can make a few dinners, so all you’ll have to do is heat them up.” I replied, “Of course, I don’t mind. It’s your sister. I’m sure I can get through a few days on my own.” Her sister lived about five...

Satin2

As Cloe and I walked into the lingerie department her eyes lit up, hey what do you think to that? In the corner was a stunning silk dress all in black with a sexy halter neck and a large slit up one side. Imagine that dress with stockings and suspenders 4” heel and you wearing it she said. Our basket was already full of sexy items; Cloe pulled the dress form the rail and asked me to go into the changing room to try it and some lingerie on. Here now I gasped. Course don’t worry Hun the...

A Nanny Femtastic 8

A Nanny Femtastic Chapter 8 When we got back to the villa I needed some time alone and left Thomas with Bradley and Felicity. We were all to meet for dinner that evening on the terrace. I had a few hours to myself and ran a big deep, bubbly bath. I had got used to pampering myself with an array of oils and scents. This and of course the regular hormone injections had softened my skin and redistributed my body mass into a gorgeous feminine shape. I probably spent too much time stroking and...

Valentines Panties

“If you like them so much you wear them,” Sara quipped, flinging the red silk panties across the bed.I should explain that in my hurry to buy her some Valentines lingerie, I had overlooked her size requirements. Sara was always fussy about her underwear, everything had to match and fit perfectly. Not only that, but she valued comfort over style. In an attempt to appeal to her more slutty side, I had been seduced by the usual man-made red silk set, complete with suspenders and stockings.“You...

My wife finally indulges in my fantasy

I come home from work to find you dressed in your sexy jeans, a tighttee shirt, and a pair of heels. I can tell you are horny by the way you tell me to get into the shower and that my clothes are laid out for me after I finish cleaning up. My cock throbs as I shower and lather my body up with some scented soap. I know you want me squeaky clean so I insert a soapy finger into my ass, cleaning myself as deep as I can. My legs are weak as my cock throbs from lack of attention. I dry off, head into...

An Introduction To My Crossdressing

Many of the crossdressing life stories I've read on Lush have similar beginnings. The early adolescence, the mother's or sister's clothes, the masturbation! It's fifty years since my first urge to dress in feminine garments, and ever since then, it has been an integral part of my colourful life.I remember the day fairly vividly. I was settling down in our bathroom, to do what EVERY adolescent does at that age. Wank! My inspiration back in those days were my mum's pals, her sister, and a couple...

Auntie s Panties

I was supposed to be home alone that day.At least that was the plan.It was the break between college semesters and I was staying near the beach with my uncle and his girlfriend, Pam. The plan had originally been to come down with a pal and spend the week blowing off steam before classes started back. A supervised vacation in the eyes of my parents --one where I couldn't get into too much trouble since there was adult supervision.But, at the last minute, my friend had to back out. I could have...

An Uneven Romance

I couldn’t believe I’d gotten her home with me. We’d met in a bar when I was drinking with my friends, I spotted her early in the night but didn’t have the courage to talk to her. She looked perfect. She was slim, with long red hair that came down to a tight, round ass. When she turned around, I saw she had a truly beautiful face but there was a sexy, dangerous look in her eyes that scared me. Incredibly, she came up to me when I was ordering drinks. “I saw you looking at me cutie, do you want...

With the wifes help

Last night I finally lived a long time dream of mine. My wife Melody of three years came home from work around 7pm and told me to follow her upstairs. Once we arrived in the bedroom, she laid back on the bed and spread her legs wide for me. She was dressed in a long white light cotton dress with a floral print and a belt cinched at the waist. The dress fell long enough to conceal most of her knee high black shiny leather boots. As I looked down at her beautiful shaven pussy, I saw first that...

July 4th Celebration

On July first I returned home from our health club. Ann was packing my suitcase for a mini vacation at a bayside resort. My suitcase was filled with all my girlie things: lubes, vibes, wrist and ankle restraints and the paddle she used on me when I was bad. She also said Ben, his brother Josh, and two others were joining us. Before continuing, I should mention how I became the man I am and how Ann took charge of me. My wife Ann and I met in college and had been married for twenty-five happy...

Caught and the Consequences Part 4

Part 4 I served dinner at 7.00pm as requested and I was made to stand by the table so that I could serve wine as their glasses were emptied and attend to them as requested. I did find the whole experience satisfying in a kind of way as I knew I was pleasing my Mistress and hopefully Sir as well, although neither of them had any conversation for me. Once finished I poured them both a brandy and cleared the table, Mistress told me I could eat...

Very Good Friends

I'd moved my print shop to a new location across town recently for a cheaper and more long-term lease. One of my first customers at the new place was a guy named Gerry. As we spoke, I found out that he was the owner of a small business as well. Gerry was a cabinetmaker and created some primo custom-built cabinetry. He'd come in to get some updated cards and stationery and wanted something with a little more pizazz than his former printer offered.We spoke for some time, and I threw out a few...

Carlos and The Garter Belt

Carlos sat in the car for a moment looking up at the sign of the sex shop. He had been in the shop on more than one occasion. A lubricant here and a toy there, to spice up the bedroom with the wife. This trip was not for that purpose.Every time he was in the shop, he was drawn to the lingerie section. In the past, when the sales girl would approach, he would say he was just looking for something for the wife. In the beginning, it was true but over time he was picturing how the bra and panties...

One of my first times

They say you never forget your first time. For me that's kind of true but in my attempts to seduce over the years I've claimed to have so many first times and I definitely don't remember all of them. Being bisexual and, of course, with my dual gender identities I have probably had more first times than most though. I was still cross-dressing in secret in my late teens and I'd never had an experience with a guy but I had fantasised about it. I'd been on a night out with a couple of friends and...

Crossdressing Fun From A Woman s Point of View

I have enjoyed reading the stories written by men to get a better understanding of what it is like to crossdress. As a woman, I find that I really enjoy and am very aroused with a feminized man. I guess I have always been a bit of a tomboy and enjoy doing athletic things, so being with a man that is the opposite seems natural to me. I used to play gender swap cross dress role play with my ex boyfriend. It started one afternoon when he came back from playing basketball. I had just finished...

Taking That First Step Part 4

It had been a long week for Lance. He didn't think the weekend would ever arrive. It was his summer job and kept his mind occupied during the seemingly endless days. He worked for a small company in their shipping department. The job was not very glamorous, but it paid well and kept him clean. Even as we worked his mind thought about what Saturday would bring when he visited Cassandra's house.Wearing the silky lingerie that Cassandra had provided got him through the long evenings. He...

First time going out for a while

I haven't been dressing much lately. I haven't been doing anything fun really. I've had a lot going on, and just haven't had the time. Friday night when I got home from work, I just plopped down on my couch as usual. I don't know what made me horny, I hadn't been out in weeks, hadn't fucked in months, hell I hadn't even jacked off for a week, but for whatever reason I was rock hard and couldn't think about anything other than getting off. If that’s going to happen, I am going to have...

Another Halloween Party Part 1

I managed to control my temper when the program director informed me that I would be making a personal appearance to function as an emcee for a Halloween bash. I thought my promotion to full time air personality would change things. I was wrong.Now, before I could launch into my rant my boss informed me that this was a costume party at the popular nightclub that was located inside of the larger hotels. The hotel had purchased a ton of commercial time to promote their party. Along with the pay...

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...

Getting A Grip On The Situation The Conclusion

"You OK, son?" Dad asked Van as he saw him shift constantly in his kitchen chair."Yeah, Pops, I'm fine, just a little sore. Went to the BMX park and for a couple of hours and then a group of us raced through the woods," Van responded."You need to slow down. That's too much abuse on your body for one day, " his parent responded knowingly.'If you only knew,' Van said to himself before he excuses himself from the kitchen table.Once safely in his room, he removed the small butt plug he...

Airing Out the Laundry

Rick was so excited to be moving to the big city. He was 22, from a small town, and got a good factory job in the city a few hours from his home town. Rick would be far enough away from his parents that Renae would be able to roam free. Rick found a little 2 bedroom apartment on the ground floor of a building in a gay community, though he did not tell his parents it was. Rick's parents were very old fashion and would disown him if they found out about Renae. Rick spent the first few days...

My date with Ben part 2

I got a call from Ben Monday morning, and he needed to talk to me urgently. His wife was going to be coming to the proposal meeting that he had talked about and she was looking forward to seeing me there. Ben asked if I would be able to be free for the day on Thursday. My work schedule was light, and the thought of going to a business meeting with them seemed interesting, so I accepted. Ben promised that if everything went smooth and his company won this project, that he would reward me...

Mike s new girlfriend

It started as a typical Monday really; I waved my wife off to work and then went upstairs for a long bubble bath and shave, as I stood drying myself and rubbing baby lotion into my body my cock started to grow as I got excited about the morning ahead. I quickly put on sweat pants and then raced to the outbuilding at the back of the garden to fulfil my cross-dressing desires. I opened the door to the outbuilding and pulled down the dressing up trunk from the roof rafters, my heart was beating...

Further Exploration

After Jerry kissed me goodnight and returned to his own room, I had time to reflect. Sex with him was so different than it had been with Jack. Jack took his time, slowly and steadily pumping his hard shaft in my man-pussy and making me feel like his special girl. Jerry was passionate and urgent, riding me hard and making me feel special in a whole different, slutty, way. I was Jerry’s special little slut, and I loved every second of being pummeled by his big thick cock. There was no doubt that...

My Road to cross dressing

I was bought up in a time when taboos about something alternative like transgender people or cross dressing was still considered to be a no go area. Society made one feel that you were an out cast or mentally ill. Luckily times have changed and it has become much more acceptable, even though we still have a long way to go. I first started dressing when I was about eighteen. My sister had this old green dress that she had thrown away. I remember liking that dress and secretly retrieved it from...

Explorations beyond my expectations

I was nineteen at the time and Lili was my first college girlfriend. She was a virgin when we met. I had only had one intimate girlfriend before her. We loved to explore together and every weekend her roommate would leave town on Friday night and wouldn't return until Sunday evening, giving us plenty of time to explore and play. She knew I liked ass play from conversations about things we'd done in the past and I held no secrets back about how I really wanted to explore those feelings further....

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,...

My First Boyfriend Part Five

Things had pretty much gotten back to normal after our wildweekend a week or so before. My boyfriend Steve and I had our unofficial “honeymoon” where I had dressed in a wedding dress and we made love. I had been out dressed as a girl for the first time and had gone to a party where I sucked off a bunch of guys for money. Steve and I had taken two of those guys home with us and they all banged me all night until their dicks wouldn’t get hard and then had started putting other stuff up my butt. I...

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...

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...

Caribean Vacation part 2

We strolled down the hall to the elevator. I did not notice what floor we went to, as I was so pre-occupied examining my sexy self in the reflective surface of the elevator. We got off the elevator and walked down the hall to a door marked 469. “This isn’t the dining room,” I objected. “No, this isn’t,” she replied as she knocked on the door. “Who’s room is this.” I asked. Before she could answer, the door swung open and there stood the beautiful Tish. She was wearing a black latex out fit...

Jessie s Office Interlude with Sue

I could not believe what a great time I had on my first date with Sue. Her planning was impeccable. From getting caught at the department store, to my new set of lingerie and clothes, and then a feminization session at the salon. Only to wrap this up with a surprise sexual encounter with Sue, her male friend Quenten, and all whom I met at the various retailers. It was a first date that I would never forget. I still was in awe at how Sue was able to plan the entire night, and have it happen all...

Friday Night Maid Part 3

Friday Night Maid - Part 3 - by Diane Leonard[I walked towards his side of the bed, stood just out of reach. Took my models pose, leaned back, and said, "Good evening sir. May I stay here for a while? I have no place to sleep anymore." part 2 ending]With that, Roger got this huge smile, jumped out of bed and almost broke the door off as he closed it. He walked over towards me, stood about 5 feet away and began to take in the image. Walking over to me, his hands began to touch me softly. I...

Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

Dressed for the Beach

Like many cross-dressers I’ve been sentenced to a life of secrecy. Over the years I have accumulated a small stash of panties, bras, shorts, slacks, blouses, stockings, and shoes. I wear them on the too little opportunities where I can sneak away without suspicion, mostly to the trusty adult bookstore. It is such a thrill to walk around in a semi-public area dressed like a woman and, sometimes, being pursued as a woman. I’ve had both oral and anal sex several times with men when dressed as...

My First Walk On The Wild Side

It wasn't until I was in my mid-twenties that I plucked up the courage to leave the house dressed as a young woman. Initially, it was short walks to the end of our street (a relatively quiet suburban road in a relatively quiet town). My hair was fairly long in those days, with blonde streaks through a feather-cut. I'd comb down a fringe to my brows to give me a more feminine look. Over the years, I had tinkered with make-up, and by the time I was ready for a "Walks On The Wild Side", I was...

First Encounter Ch 1

We have arranged to meet for the first time at a hotel in a large city halfway between our home towns. I arrive first, pay for the room, and text you the room number.While I'm waiting for you to arrive, I decide to get dressed. I remove my clothes from my suitcase and proceed to the bathroom. I strip down and admire my naked body in the mirror. I begin with a complete body shave, paying particular attention to my private area and rear door. I want these to look attractive to you so I take extra...

In Wonderland Pt 2

To recap, our protagonist didn't want to dress up for a halloween party, so his girlfriends decided it was time he joined in the fun. They styled his hair, did his makeup and put him into an 'Alice' dress. However, the disguise worked a little too well, as Chris Smith has taken 'Tilly' back to his house after a passionate kiss on the street corner... Chris put his key in the door and unlocked it. It swung open into a dark hallway with wooden floors, and he said "Ladies first," indicating for...

My New Life As A T Gurl Slut Pt 3 Nine Cocks in 48 Hours

I was going to be the gurls' slutty French maid for the night and couldn't wait to get to Karen's so the fun could start with four hot t-gurls and four hot cocks for my mouth and ass. Lucy picked me up, and as soon as I got in her 4x4, I slipped out of my jeans to reveal my knee-length black boots, black lace top hold ups, black suspenders, and wet look black micro mini skirt. I unzipped my jacket to show off my sexy black bra around my C cup tits that were firmly attached making me feel sooo...

The End In

The following afternoon, I can’t concentrate on the class I’m supposed to be giving. Jordan sits in the middle row. The lecture still interests him, but his eyes lose focus every once in a while as he switches positions. He’s being a good girl.One of the other students asks whether the air-conditioning is ever going to be repaired. I can only offer her a shrug and a commiserative smile. The superintendent has promised to take care of it but has idled by the overgrown orchard all day. Perhaps,...

Caught in My Girlfriend s Panties

Bella was wearing a black and white checkered wrap dress. The deep-v neckline teased her ample cleavage. Without seeing it, I knew she was also wearing a half-slip and lingerie chosen to please me. I pinned her to the foyer wall as soon as we entered her house. We kissed. I grabbed her soft ass.She had a midwestern look with fair skin, dirty blond hair, and blue eyes. She was fit, but not slender, with a big sexy ass, smooth thighs, and nice bell-shaped tits. I took her hand and led her to...

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...

The Party I Fucked

Phebe stepped out of the bathroom and pulled on my panties. Bill had been fun but she needed to get home and change into men's clothes to go to work. The wig, frilly skirt, stockings, blouse and wig would stay at home."Bye Bill, need to get home." With a peck on his cheek, Phebe rushed out the door to her car. Her ass was a little sore from Bill trying to fuck the shit out of her. Phebe had loved every stroke.My phone rang just as Phebe started driving home."Hey George, what's up?" "Hey...

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

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

the summer I became Suzie

I was 18 years old and taking estrogen for about two years. As my ass and tittles started to grow my desire to dress up became all consuming. I wore sexy panties to school everyday and the excitement about getting caught, grew as well. I was very tiny for my age and picked on by the jocks at school regularly. I'm 5foot 5inches tall, with long brunette hair and blue eyes. I had no body hair and a penis so small, my panties made it almost disappear. Which was OK by me, but I wore baggy clothes...

In My Panties

Larry and Sarah were your typical yuppie couple working two professional careers. Larry a techno wiz was the research and development department head at a local manufacturer while Sarah was the office manager at a local Saturn car dealership. Their weekends off work were filled with their hobbies of camping and outdoor fun. Both loved nature and enjoyed their time together on beaches and in parks relaxing and having fun. Larry was enamored of Sarah and all her strong ways. She was so confident...

Married Crossdressing Fun Ch 2

Caz and I had been living in our new home for about two months. Our life was wonderful. We loved each other more deeply every day. Caz enjoyed her new job and she was really good at it. She was a beautiful, sexy woman and in the field of international finance surrounded by mainly middle-aged men, she had the advantage and wasn’t ashamed to use it to further her cause. Her company was making record profits and she had already had a pay rise. She was also in line to get a huge bonus at the end of...

The Cardboard Fort The Conclusion

My duo identity was not an easy thing to maintain. My lingerie was washed in the half bath sink in the wee hours of the morning. I then had to creep downstairs and hang them in the fort. They along with the wig and makeup were kept hidden in an old suitcase with a working lock I found in the second-hand store.All this secrecy was necessary because young men did not want to dress and behave like a girl. Heaven forbid my parents to find out about this and how Gene and I spend our time together in...

My First Trip Out of the Closet

I have wanted to write this story for many years but I hesitated to do so out of my fear of the unknown. Since moving to Florida , I have pretty much been on my own for the first time in a long time. Let’s just say that now that I am older, I’m bolder! I no longer care who knows my sexual interests. It’s funny, because everyone I currently see understands my desires and approves of my different fetishes. Foremost of these, is my predilection to live my...

Meating Samantha

It had been almost two years since my first experience with Dave. That was the first time a man had sucked my cock. It was the first time I had touched another cock and the first time I had sucked a cock. That day was the birth of a new me. I no longer was a homophobe. Although, I did not look at men the same way I looked at women. I did not lust after them. What I did lust for was for a cock in my mouth, loads of cocks. My god, I had become a cock-craving freak!I did not have any guilt....

Ready to Perform Part Two All Crossed Up

Much happened in the next twelve months following that first session with my ex and her new partner: Ann began divorce proceedings which I didn’t contest, I financed myself into another home, and Ann, David and I met for two more sessions of torrid sex. These sessions were pretty much replays of the first; I would first screw Ann thoroughly through at least two climaxes, and then she would watch avidly as I serviced her partner David, playing with herself and having a further orgasm as she...

Learning to be submissive part 1

Before the days of internet chat rooms and social media I was very lonely as a young cross dresser. I can't speak for everyone of course but I would use telephone messaging services to talk to like minded people. I had received my first mobile phone for a recent birthday and I would often call up to chat to people. Sometimes things would turn into phone sex and on the rare occasion I would give out my phone number. One person whom I deemed worthy enough to have my number was a man called Jack....

One On The Way

Ryan arrived home from work earlier than normal thanks to lighter than normal rush hour traffic and he was quite happy. This would give him plenty of time to get ready and ensure that his mobile home was clean enough to receive visitors. Once satisfied on the condition of his place, he stripped off his work clothes and headed to the shower.He spent an extra amount of time allowing the warm soapy water to clean every inch of his body. Still dripping with warm water, he reached out of the shower...

Girlyboy Gone Wild Part Three

With my little sexy blue plaid school girl skirt pulled up, I leaned over the desk for teacher Dan to spank me. Dan reached down and pulled down the back of my little white cotton panties revealing my very sexy ass. I saw how big his eyes got when he saw two of the sweetest cheeks he ever saw. He looked up at me."You have a nice butt on you, Courtney."I smiled. "I hope I get to sit on your lap with it teacher."I saw his cock growing even bigger as he thought about me sitting on his lap like a...

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...

Beach Day

Wearing my sexy panties to the gay beach always gets the men turned on for me. Being the only girlyboy there, I get hit on by lots of big studs. The attention they give me is flattering and leads to lots of sexual pleasure. Being topless, I get to show off my nice titties and the sexy panties I'm wearing let the men know I want some dick like a woman gets.It was a beautiful day for the beach and I had off from work. Just a few miles from my house is the gay beach where lots of men go to meet...

Mrs Robinson s Panties

Mrs. Robinson was like a little sister to my mother. I wasn't even sure how they'd first met, but she was always around when I was growing up. When I was in junior high she'd gotten married and bought a house just up the street from my family. Unfortunately, the guy had turned out to be a jackass and she'd caught him cheating on her--just after their first kid was born. She got to keep the house. And, of course, my mother felt it was her duty to offer the services of her teenage son to help...

The Only Cure Possible

Mia was standing in front of the dresser, checking her reflection in the large mirror that gave me such a wonderful view of her beautiful face and upper body. I could see her glance to the side and knew she caught me staring at her ass and legs. Her smile was warm and genuine, and I knew she didn’t mind the lasciviousness in my countenance. If anything she considered it a complement, or at least a confirmation that the outfit she had chosen to wear tonight was having its desired effect on me....

Seducing Uncle Frank

This is a story that happened some time ago, when I seduced my Uncle Frank. Uncle FrankUncle Frank was married to my mum's sister. He was about 10 years older than Aunt May, and it was both their second marriages. Uncle Frank had an Italian father, French mother, three older sisters, loads of nephews and nieces, and had property in Kensington, the Algarve, and Telluride. You could say he was quite wealthy.They had met in the early 1970's, and spent their wild and wonderful life traveling the...

My First Time in a Dress

PART-1 When I was younger I used to go and stay at my grandmas house during the summer. It was a small country town with about 15,000 people. She lived on a quiet street and there was only a couple of other kids close to my age. I used to go and hang out with one guy, Dan who was about 3 yrs older than I and his sister, Pam who was my age. Dan and I used to go mess around everyday. His parents worked from early in the morning to around six to seven in the evening. One day we were out messing...

Neighbor Camilla

This is a work of fiction, if you do not like it move to another post.Chapter 1:I sit looking out my window thinking about my life and the past couple of years, living in the city in this nice apartment with wonderful neighbors and now friends. I first moved in and the older man that lives next door, Alex, offered to help. I was glad for the help, and as the day went found myself more and more attracted to him. I knew he was attracted to me, the number of time I caught him looking at me and my...

Mistress Hannah s Pathetic Husband

My life had become miserable. It had taken two years of marriage for it to happen, but it had become much worse in the past few months. The worst part about it was that it was clear that my sweet wife's life had also become miserable and that she thought it was my fault. And maybe it was, but I didn't know why. I suspected it was because I'm a miserable example of a man and she deserves better. I'm a lousy lover. I have a tiny dick and I come too quickly. Even if I lasted longer, I don't have...

A Maid Story

It had been a long day and Paul was tired. After a week of traveling and a full day of meetings, Paul was ready to unwind with his wife, Marie. They were what many people might describe as soul-mates. They were best friends who shared their deepest, darkest secrets with one another and who regularly consulted with one another on a wide variety of topics. Their love life had suffered lately and had grown somewhat predictable but that didn’t bother Paul too much. There was so much...

Ray and the Halloween Party

I have had sex with a few guys since my last story but there nothing much worth writing about so I thought I would “go retro” and tell you about a hot experience I had in my senior year of high school. At that time I kept my crossdressing pretty much private and only a handful of people knew about my slutty side as Lisa. Even most of my best friends had no clue. (At least that’s what I thought at the time.) One of my best friends was a good looking guy named Ray. Ray lived...

Exposing Myself To A Group

Rachel decided it was time for me to come out to others more than I ever had. She did some research and found that a meeting for trannies was taking place at a motel just outside the city. She took a room and checked us in, then we had dinner and went to the meeting room. The room was in a large motel suite. We arrived early. Rachel had dressed me and I was definitely 'out'. I was wearing open-toe wedge sandals, my toes polished pink, a thin sundress with a short skirt mid-thigh, a soft white...

Jessie s Payback Continues

It was turning into a wild night, and I was the party favor. After Zach and Aaron had their way with me, I thought I was done for the night. But I couldn’t have been more incorrect with my assumption. As I was getting ready to leave the living room, Dan tugged on the chain that was attached to my neck choker. I went to my hands and knees much to Dan’s pleasure. Zach, and Aaron had been giving each other high fives for their conquest, and commenting about my need to be a sissy and a cum slut. I...

Meeting my Ex Girlfriend s New Boyfriend

Not long after I got out of the service, I met Trish at a house party. She was a hot little brunette with a great body and we hit it off right away. After a few months of dating we ended up moving in together and she was a great lover...with one little quirk. She always wanted me to wear a pair of her panties while we were having sex. I readily obliged because she was so good on her back and also gave the best blow job I've ever had. I got used to wearing her underwear and have to admit that I...

Confessions of a Sex Crazy Cross Dresser

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

My 2 AM Phone Call

It was about 2 AM when the phone rang. The voice on the other end simply said to get dressed. He told me exactly what to wear. Exactly. He wanted me in a black micro mini skirt, little black mesh top that barely came below my nipples, five inch platform heels, lots of junk jewelry and a bushy Vegas platinum blonde wig. He said to come to the Diamond Motel on the Gulf Freeway and then he hung up. I recognized his voice as the black man who I had met at a video store several years ago. I'd seen...

High and Dry Part 3 You re Gorgeous

Affairs began to hit their stride between Emma and me after that Queen’s Birthday long weekend. We had spent much of the remainder of that weekend either in or around my bed: we made love a few more times, but much of the time was spent just cuddling up under my quilt. Eventually on the Monday I dropped her off at her mother’s house, our parting kisses taking even longer than ever.While her and her sister Amber’s living arrangements reverted back to fortnight-long stretches with each parent,...

Frank

Frank didn’t vocalize his orgasms. So I never knew he’d cum until he stopped his motion and pulled out of me. Then I’d look over my shoulder with a smile and ask, “Did you cum?”And Frank, already backing off the bed, his big cock curving downward now, would reply, “Yeah.”Although normally quite chatty, in the immediate aftermath of sex Frank turned into a man of few words, a regular Clint Eastwood (though not nearly as tall or handsome). Without having to be asked I would back off the bed as...

No Strings Attached Penitence Chapter 19

My fingertips graze against the silken, soft fabric, then travel under, greeting taut, warm, muscular skin. Low, gentle moans hang heavy with lust; sexual heat rising as my nipples are pinched, grow erect and brush against the satiny material. My tongue trails over my bottom lip as my need elevates and I reach down, finally, and touch smooth, unyielding steel whilst my mind becomes flooded with indecency."Mmm, Ashleigh... Ahh, fuck!"The flash of pain from my sensitive flesh, being crushed...

Bought

I love the transvestite lifestyle. Since I was sixteen, I have been boldly going out dressed to the nines as Cari in public. Now finally of legal drinking age, I go out to one of Boston’s gender friendly nightclub establishments on the weekend. I am lucky to be considered one of the prettiest and the most believable of the girls at these clubs. At five foot five inches tall and one hundred and thirty five pounds I have a body that looks good in almost any kind of dress!I have naturally blonde...

Confessions of a Sex Crazy Cross Dresser Part 10

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

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...

Two Cowboys and One Dancehall Girl Part One

I live in a town where the national rodeo cowboys come to town every year. And each time they come the testosterone level in town goes up, immensely. All of the big handsome, strong men in spurs and chaps and jeans and western-cut shirts and cowboy boots and cowboy hats get my clitty dick stirring down in my little panties when I see them around town in their pickup trucks or sitting tall in the saddle on horseback. They look rough and rugged and ready. And I'd be lying if I didn't tell you...

Once Again in Silk Part 1

It had been many years since my time in Florida and my transformation to Melissa to please my lover, Lydia, and also my own inner desires. She soon grew out of her desire to see me dress up and wanted a normal lifestyle and to date other men.It seemed that our time together had come to an end. I gave up my apartment and I moved back North.As I still had a sizable amount of money left from my settlement. I didn't need full-time employment and I took a part-time job as a bartender in an upscale...

Caught

He had a stressful day and just wanted to relax when he finally made it home. However, when he arrived back he realised the place was a mess and needed tidying up.He then hit on an idea to make it a bit more fun. He stripped off all his clothes and went to his sissy wardrobe. He took out the very skimpy maid uniform, tights, and a pair of pink panties.Soon he had changed and then went to his toy chest and took out his thick collar that restricted the movement of his head. Finally, he put on...

The Adult Theatre

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

Joann s Club Paradise

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

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