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Crossdressing

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20

A Real Lady

What's a real lady, anyway.

It doesn't matter to me in the least. I just love it. Sex, that is. I love it all. Well, I don't suck cock, and I don't take it up the ass, except from a beautiful woman, after I have screwed her ass hole, and every other hole she has. Turn about is fair play for the ladies. I don't play that game with the guys. She was a pretty little thing in a red dress. I was sitting at the bar. We...Read On

19

Hitch-hiking Baby Doll: Part One

Hitching a ride with a trucker leads to loads of fun for this sexy little tranny boy.

I hadn't been in his cab for more than a half hour when the driver who picked me up, brought up the subject of sex to me. "Last week, I had a guy and girl riding with me and they both liked giving me blow jobs. And, you know, if I closed my eyes, I couldn't tell the difference of which one was sucking me off. They were both excellent at sucking cock." "That sounds like you had a fun ride,"...Read On

4

Night at the Video Store, part 3

bimbo crossdresser cruises video store in Black part of town

There I was a sissy bimbo dressed like a slut in a short black micro mini skirt, spike heels, lots of junk jewelry, huge platinum blonde wig, shoulder strap white fur purse and, of course, perfect make up. I had never been to this video theatre before and was nervous at first, but I waited for my eyes to adjust to the darkness and then moved into the theatre area. Screen five was recommended...Read On

21

An Uneven Romance - Part Two

He's taken further into her strange, kinky world

“Hey, Sam.” I jumped and spun around, startled. One of my housemates, Mark, had walked into the kitchen where I was preparing breakfast for Sarah, the incredible girl I’d brought home the night before. Sarah was a pretty special girl; after a night spent with my head between her legs she had eventually let me cum this morning. She’d somehow coaxed me into wearing her wet panties from...Read On

12

My First Encounter

This is about my first sexual encounter with a man

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...Read On

11

A Welcome Predator

A crossdresser discovers his bisexual nature

I first met Jim in the lobby of the youth hostel. I wanted to check with the receptionist if my parents had wired through any money. I was supposed to be studying, but I’d spent most of my time going to parties with other kids of around my age. They knew all about the fun stuff in life and where to go to get some action. My money was all spent. I desperately needed some smokes. “How are...Read On

19

Just For The Taste Of It

Vanessa is trained to love the taste of cum

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...Read On

22

Accepting an invitation

On the third day of house sitting, I awoke to a nice surprise. After my neighbour, Daniel, had unexpectedly visited, I had decided to work on my make up and mannerisms. After a day of walking in heels, I had perfected my sexy walk as well as getting my make up just right. I was feeling in the mood to show off my new found skills so was excited to see a note waiting by the front door. It was...Read On

16

Andrew to Andrea - Part 3

..the next step...

 BRRRRIIIIIIINNNGGGGGGGGGG!!!!!! The alarm clock that my wife and I mockingly referred to as “Baby Ben” sounded off and pulled me from what I first thought was a great dream. As my senses slowly came online, I could feel my hand laid over my naked wife’s breasts and that I wasn’t in my usual gym shorts and t-shirt. I was surrounded in silk, and it was not unpleasant, but it was a floor...Read On

25

The Young Crossdresser Part 3

So the next night arrives and once again I find myself dressing up to head back to mom and dad's porn store to see if my lover from last night might be there. We had scheduled to be there around 8:00pm. I arrive in my car,check myself in the mirror and go inside. I see him instantly standing in the front looking at magizines and walk over to him and say hi. He smiles and looks me up and...Read On

27

Hot Fuzz

Caught by a cop

If you have read my profile you would know that I am married with three kids, and no privacy. That being said, I try to indulge in my favorite pastime of cross dressing whenever and wherever I can. I was working as a manager for a convenience store where I would have to get up early in the morning to open the store. It was a 24 hour store, so I just had to get there to send the graveyard...Read On

20

My Dream story Part 1

My first story, be nice! Just a start to this story line.

My name is John, and this is my dream. I am 18 years old, I have dressed before but never seriously, and down the street from me lives a woman named Sarah. She is the mother of a very wealthy family and just radiates control and success. Ever since I had seen her, this story has played over and over again in my mind. So here it is. I woke up and the weather couldn't have been nicer. The sun...Read On

14

A night at the resturant

I was looking sexy enough to eat at the resturant.

I met John online; he was the owner of a small town restaurant, who was also married.  I agreed to meet him that night after he closed.  When I pulled up to the restaurant the lot was dark.  I hustled up to the door in my tight mini and stiletto heels, my heart was racing faster with each step.  When I got to the door John was waiting and quickly let me in.  We sat in the back and he offered...Read On

8

Adventures in a Woman’s Body – Chapter 5: Secretarial Duties

Serving some very important people as the secretary

John waited for me to finish eating my cum burger, and then he told me to get up because we were leaving. I stood back up onto my six inch stilettos and walked with his arm around me, which firmly grabbed my ass. We exited the food court and made our way to his office building. The mall had a vast underground network so we were able to walk to his workplace without going outdoors. Along the...Read On

10

Girls Night Out Part 2

Cassie and her friend's evening continues

Girls Night Out Part 2 Well everyone wants to hear about the second part of my night with Julie when I was in New Jersey. In case you didn’t read my first story, my name is Cassie, short for Cassandra (I also go by Sandy sometimes) and I am a cross dresser (CD). A while ago I was spending a hot summer night in New Jersey at a hotel with my friend Julie. We were attending a girl’s night out at...Read On

22

My New Boyfriend

Workout buddy sweeps Courtney off her feet

I recently moved to a new town and joined a gym. It's not one of those fancy gyms with weight machines, a latte bar, and women in spandex running around trying to be noticed by men. It's a sweaty men's gym with barbells and dumbbells that require men to double up and spot for each other. The first day I was there, Jack "Kell" Kellson, a solid built six-foot-three-inch muscle boy my age,...Read On

21

In Her Shoes

I opened my online mail box as usual, looking down the list in case any new spam was in amongst the thirty-seven mails I had received. As I scrolled down the page I noticed a new mail from one of the sites I used to find new partners for sex. I clicked it open straight away not wanting to waste any time, hoping that this mail for once was from someone more sane and rational than the usual,...Read On

16

Becoming Mary - Part II

A girl discovers her dominance while a guy discovers his submissiveness

When Lucy had told me about Amanda liking men wearing panties I thought she was talking about a fetish thing. I didn’t realize there was more to it than that. About a week later I had just arrived home from work when I met Amanda in our apartment hallway. She had been to see Lucy and was on her way out. “Hi Amanda,” I said as she stepped into to the elevator, “How are you?” “I’m fine,”...Read On

28

Tickets please!

My life changed forever on the 07:28 from Bristol

Standing by the window, I watched as the countryside flashed by. My train had been delayed due to a dodgy signal just outside the station, but judging by the speed the driver was maintaining there shouldn't be much of a delay, thank goodness. Even though I hated my job and boss I needed the money desperately. With a sigh, I turned away from the dreary grey outside and tried to make...Read On

22

My First Date

I had met Pete over an on-line dating site, and we had chatted for several weeks and developed a rapport when we decided to have our first real date. We agreed to meet at a local shopping mall parking lot and would do some shopping together. I spent the morning shaving my body smooth and getting ready. I went with a natural look for my make-up, and peachy pink lipstick. I slipped into a...Read On

22

Being Christy - Part 2

Caught by the neighbour!

To be honest, I was panicking. From the outside I looked like an average teenager. Skinny black jeans. Indie band tee, maybe a size too small on my Bowie-thin frame. Cherry red Converse high tops. Straight dark hair cut into a fashionable (if you were an NME reading indie-kid) boy bob. But underneath I was sporting skimpy black panties and stockings and suspenders, all ‘borrowed’ from...Read On

16

While the Cats are Away

Kelly's best friend catches him dressed up

Thursday night, mom is going to visit relatives out of town; dad is away on a business trip and not supposed to be back until Saturday. It took a lot of convincing that being sixteen is old enough to be able to stay home by myself and not have to go with mom to visit relatives. Dad was going to be home in two days and I would be going with him to the family ranch. Finally my mom relented and...Read On

16

How It Started

I looked and saw her panties in the hamper.

At twenty five and being a blonde haired blue eyed light skinned guy, I had little hair except on my head. So, it didn't take long to achieve the smooth feminine look that I wanted. Of course, I left some "down below" because I looked young and if I shaved it all off I feared looking underage. My blonde hair was long, during the week I wore it in a guy style. On the weekends it was different,...Read On

Mistress Hannah's Pathetic Husband Part 5

I serve lunch to sorority sisters

I was making progress as a slave but unkown to me, one of my stories helped Mistress Hannah see an opportunity for a particularly fun afternoon and a chance to help an old friend through a rough spot in her marriage. Several months of aerobic classes and feminization had increased my stamina and made me more comfortable when we spent our Sunday evenings out for dinner and as member/patrons at...Read On

19

Office - Caught 2

I couldn't focus, my head was racing with all kind of thoughts. I had no idea what this would result in. My manager and teammate noticed something was wrong. I just told them I was coming down with something and felt ill. As there was only about an hour before closing time, my boss told be to finish early and get myself home, dosed up and to recuperate over the weekend. I didn't need to...Read On

33

Becoming Sarah

A man embraces his femininity and gets changed forever.

I was driving home from a work trip. That is how it started. There was roughly 85 miles to home. I had been driving for about an hour when my mind began wandering the way it always does when I'm not preoccupied. It always goes to the same place. For the better part of five years, I have been cross-dressing in secret whenever I have the house to myself. Sometimes I do it because it...Read On

17

Laying the Groundwork

Extending the boundaries with my fiancee

My fiancée and I always have been a bit more adventurous than the average couple when it comes to sex. While we both enjoy the sensual feeling of pure, romantic love-making, we also tend to get a bit rough and voracious when the moment calls. In the past, we had experimented with some anal play, with me initiating most of the contact on her. Fortunately for me, her hands also had wandered a...Read On

26

Jessie's Reward

After a hard week at work, Jessie gets her reward.

It had been an unusually long and hard week at the workplace. The week started on the wrong foot when a major project was likely to be delayed by a month because of a supplier issue. Stress was adding up through the week as my manager kept demanding that I get the project back on course by week’s end. Come Thursday, there wasn't an end in sight. I was thinking my job will be on the line. I...Read On

19

Extended Vacation

The first chapter of my second novel

Hi Everyone...this is the first chapter of my second book. I will publish more chapters if you like this one. Extended Vacation Chapter 1 Hello my name is Cassandra. You can call me Cassie (or Sandy, but recently, I like Cassie). I have been cross dressing for many years. However, the last year, since I turned 40, I have been dressing more than I ever have in my entire life. I made a...Read On

30

Emmy's Games (Part 1)

Emmy takes control. Continuing on from the original encounter 'A Surprise Ass-Fucking in Panties'

“Put my panties on,” says the text message from Emmy. It is 9:30am and I have just woken up. I look across to the bedside table and see Emmy’s panties sitting there all dried out from last night's shenanigans. I lean over and pick them up, and can’t resist the urge to hold them to my face momentarily and savour their aroma. I do as the text message asked and put on Emmy's cotton panties....Read On