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Crossdressing

13

Andrew to Andrea - Chapter 2

Andrea's first small steps.

In all honesty, I should have been mortified by the events of the past few minutes, but I wasn’t…I was excited. I walked into our bathroom and set up the steamiest shower that I thought my skin could handle. I grabbed for my body wash, but realized the scent might be too masculine, so I set it back and grabbed my wife’s. It had a slight scent of vanilla and had a couple of butters and oils...Read On

22

Andrew to Andrea (Part One)

Andrew is about to really see the other side

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....Read On

21

My Day in Panties

The day I spent at work in my hot panties

I'm a 21 year old sales rep for a drinks supplier. I'm tall and skinny, and love little sexual secrets....today was just another day in this secret life. The alarm clock rang out like a drill sergeant screaming at his soldiers. 6 AM and it was already light outside. It looked like it would be yet another clear sunny hot summers day and I awoke laying naked in my bed. It appeared that my...Read On

10

I Still Love You Tomorrow

How could she be so forgiving? I didn't understand... Caught with the evidence of my secret on my face, my body, and in my hair, I was frozen by her stare as she stood in the bedroom doorway, eyes wide as teacups. “Oh,' she said, too shocked for anything more. I had lied to her! I wouldn't have blamed her if she had left me in that instant, but she stayed. Why? How? We sat together...Read On

19

The Slut Within part 2

part 2 of the slut within and if you like it PLZ comment :) enjoy!!!

As I continued on my knees, I felt my little thong riding up my tight little butt. My skirt got in the way of spreading my legs and my tube top and my skin was all sticky with cum. Thankfully, I wouldn’t be wearing any of this much longer. Their watching eyes so aroused my slutty nature. I took off my tube top and skirt leaving my fishnets and six inch heels. I also wore a black thong and...Read On

46

The Panty Princess

Dominant girlfriend discovers her love for submissive boyfriend

Jane and I had only been living together for three weeks when I was caught red-handed. I was mortified when I saw her in the mirror, standing behind me with her mouth wide open. She had managed to come through the front door, up the stairs and into the bedroom without making any noise. I tried to explain that it was the first time I’d ever done such a thing, but she was having none of it. ...Read On

6

Can't Judge A Book By Its Cover

Not everything is as it seems.

Hillary sat on the bench outside the courtroom that Monday morning. She tugged at her skirt, trying to make it appear longer. She tucked stray tendrils of hair back into her casual chignon. Hillary was nervous and it showed. Even though everyone told her that she had an absolute barracuda for a lawyer, she still had nightmares as to how this would all turn out. Yes, Will had verbally agreed...Read On

11

Suzie and Cindy are taken to their first gay club

this is my fantasy life

As Cindy walked into the room with the outfit I picked for her, she had a distinct glow of a satisfied girl. Harry and Jack added pink nail polish, matching garter belt, thigh high fishnet stockings, jewelry, high heels and they cut bangs into her hair. She really was pretty. The three of them stood there while I was still riding Joe's cock, he was in no hurry. I must be becoming a good...Read On

16

I am Suzie

This is my fantasy.

The coach was lubing up his cock. It actually was getting bigger. The veins along the shaft were thick and gorged. I could not take my eyes off it. Then he started humping the crack of my ass. I knew he was letting me feel how huge he was against my ass. I was so turned on that I started to wiggle my ass and grind his cock. He enjoyed that so much, he stopped humping me and let me do all...Read On

18

the day i became Suzie chapter 4

this is my fantasy

I went back the next day dressed sexier than ever, but Jack and Harry did not show up. I waited for hours. Then cried all the way home. I cried myself to sleep three nights in a row. Now I knew how a women feel after being fucked then forgotten. But then on the fourth day Harry called. I instantly went into my sweetest voice and asked, "Where have you been?" "Guy stuff Suzie.You...Read On

27

The Slut Within

This is my first story. If you like it please comment and I will write chapter two :)

I was 22 years old at the time, and I had been crossdressing for a few years. For some reason I could never control my desire to put on women's clothes and prance around my apartment looking all sexy and slutty. Normally I can never decide what specifically to wear as I like to change it up all the time, from wearing latex lingerie to sexy roleplay outfits and beyond. I am 5'9 with a...Read On

24

Teenage CD Awakening Part II

A teenage boy widens his crossdressing horizons by starting to wear his mother's clothes

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...Read On

15

the summer I became Suzie chapter 3

this is my fantasy

I woke up early, hell I could not sleep any way! I had so many wet dreams about what happened yesterday, I had to change my sheets. After throwing the sheets and yesterday's outfit in the wash, I went back to my bedroom to take a shower. As I soaped up, all I could think about was Harry and Jack's huge cocks. I lubed up my pussy. And after drying off, painted my toe nails whore red. I...Read On

17

the summer I became Suzie chapter 2

this is my fantasy

CHAPTER 2 My eyes follow a trail of goosebumps to where Jack's gentle tongue teased my sensitive nipples to life, driving me crazy. He reached into a pocket of his discarded shorts and pulled out a tube then demanded I turn around so I could see my pussy. "Wiggle that ass and tell me how you loved sucking Harry's cock"! Jack grated. "Oh yes, I loved sucking his cock." "Can you still taste...Read On

15

the summer I became Suzie

this is my fantasy

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...Read On

36

Old Friend, New Relationship-Part 1

As it turns out, I confided my crossdressing desires in just the right person

Old Friend, New Relationship-Part 1 I met Karen in my divorce support group while I was dealing with my second divorce and she was trying to cope with her first. About the only thing that we had in common was that both our spouses had cheated with good friends of ours. She was a couple years older and very attractive. I remember that she always dressed so well for our group meetings. We...Read On

17

Teenage CD Awakening Part I

A tale of a teenage boy’s first overwhelming urge to try on a pair of panties

As a child I lived in a town in the North of England. It was a fairly conservative place, where boys were expected to grow up to be men, and girls to become women. Despite this my mother was a fairly liberal person, and by the time I’d reached the age of 17 the topic of sex had already been raised in our house. Sex between men and women of course, with the aim or perhaps the danger of...Read On

37

Put it on!

A not-so-reluctant housemate dresses for his live-in landlord

I was living and working in London, my first job after college. No chance of having a place of my own with these crazy house prices and this being my first job at the age of 23, so I rented a room from a guy older than me, in his mid-30s. His name was Steve and he was a masculine type, split up from his wife but seeing a feisty Spanish woman called Manuela. There were big arguments now and...Read On

31
Audio version available

My first time

First time with a CD. First gay experience.

My first story. And it is the true story of my first encounter with a CD. With a click of the mouse, I had committed… I was going to meet a cross dresser just a few miles from home. Could I go through with it? Is it really what I wanted? Who was I kidding? Of course I wanted it. Now it was time to just suck it up, princess. I took a quick shower and the dressed in my tiniest,...Read On

37

TV Repair Man

DISCLAIMER: Story is merely fantasy and completely fictional. So please do not believe this happened to me or ask me questions about it, thinking it is true. I am writing from the first person perspective simply because it is a fantasy and it’s just more fun that way;) About a month ago my TV broke and it is kinda big and expensive, so I decided to have it fixed rather than buy a new one....Read On

60

Ashley’s First Time With a Guy

Ashley’s First Time With a Guy DISCLAIMER: Story is merely fantasy and completely fictional. So please do not believe this happened to me or ask me questions about it, thinking it is true. I am writing simply because it is a fantasy and it’s just more fun that way;) So it all started on Valentine’s Day of that year. My wife and I had gone to dinner and got a hotel room for a romantic...Read On

13

Extended Vacation Chapter 3

Cassie continues her new life

Cassie has her first full day as a woman as she continues her seven weeks living as a woman 24/7. EXTENDED VACATION Chapter 3 I arrived at my new apartment around 5 PM, and it took me over three hours to unpack and get organized. It was very enjoyable to move in and have a fresh start. I loved looking at my closet and all of my drawers as everything was for Cassie. My bathroom...Read On

17

Bo Peep and the neighbor

crossdresser role play

It had been a hot summer and I had no luck finding a job. My parents did not seem to understand that there just weren't that many companies hiring that year due to the economy so they had really been pressuring me to find a job. They all wanted someone with experience but having just graduated high school I had none. I was nearly at my wits end so when I was asked to house sit for my uncle...Read On

62

My Strapon Fantasy

A girl helps her boyfriend live out his fantasy

I woke up in the middle of the day and smiled; my girlfriend had gone to work a few hours earlier and promised me a really good time when she got back. I ran upstairs to shower and make sure I was hairless before getting ready for her. I wandered into her room to dress for her arrival. I found a purple sheer thong and matching bra in her underwear draw that would be perfect. I really wanted...Read On

12

Extended Vacation Part 2

Cassie continues her new life

Chapter Two in my novel of Cassie living 24/7 as a woman...please read Chapter 1 and let me know if you want more. EXTENDED VACATION Chapter 2 After experiencing a great sexual adventure less than two hours after becoming Cassie full time, I was now in a even better mood as I got back on the freeway and headed north. Due to the low air pressure in my tire, I drove around 50 MPH for...Read On

18

Jack's Little Bitch

Learning to be a girlfriend

Steph had been gone for about one week out of her two week visit to her Mom. She'd asked me to pick up the mail and water the plants while she was away, because her boyfriend, Jack, was also going to be away for the month on a business trip abroad. “Jack wouldn’t remember to water the plants even if he was there,” said Steph, laughing. “At least I can trust you.” Steph was right...Read On

15

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

32

Cindytranee meets the maintenance crew

Cindytranee gets caught crossdressing and gets fucked by three men

This is a true story that happened a few years ago when Iwas living in an apartment complex while looking for a house. I had taken a small one bedroom on the 2 nd floor. It was very nice and private and I really enjoyed being there. This was the first time in years that I had lived alone and I loved it. It gave me the freedom to enjoy my favorite thing, cross dressing and having sex with as...Read On

31

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,...Read On

46

First time

I was 17 when I had my first experience with another man. My sister was in her sophomore year at college and I in my senior year at high school. She was going to spring break in Florida and since me and her had always had a great relationship she invited me along with her and her friends. My sister was cute, blond hair and blue eyes. Very tan and athletic. She had that all American preppy...Read On