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Crossdressing

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21

A Picnic in the Park

Wearing my sexy thong bikini to the park leads to hot action with a big stud.

It was a beautiful spring day, the kind of day a girl starts to think about wearing her new bikini to show off her hot body for lots of men. I was feeling frisky and thought meeting some new men would be fun. There was a county park near my town where lots of men go to meet up for some good blowjobs and hot encounters. I planned to go there today. My new bikini still had the tags on it and...Read On

19

Bookstore Crossdressing

Giving Up My Butt-Cherry

It was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out. ...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

16

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

31

Humiliated by my best friends

I had recently met a kinky lady online who agreed to be my mistress on a frequent basis. Tasks she set me included wearing panties to sleep in, leaving a butt plug in me, while we chatted and other kinky things. Last night, while we were chatting, I told her I was going to a friend's house with a few of the guys, to play cards and have a few drinks. Her dominant side took over and she told me...Read On

31

Chrissy's First Bookstore Trip

Chrissy's First trip to an Adult Bookstore Arcade

After my first night dressed up like a girl in my very own clothes I started to wear panties and thigh highs under my pants when I went to class or anywhere for that matter. I couldn't get over the sexy feeling of the panties on my cock and the nylons on my legs. By now I had purchased quite a few women's clothes. I had all different colors of matching bras and thongs, I loved the way the...Read On

23

Being Sissy To My Brother In Law

Caught in panties, bsque and stockings.

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...Read On

42

The Neighbour's Knickers - Part 1

A man who just can't resist the opportunity to get into his neighbour's knickers

It was a sultry summer night but it wasn’t the muggy air that was making me hot. It was my clothes. I’d felt the urge to dress up in a very sexy outfit. My preparations had started much earlier in the day, and they had been thorough: my whole body was clean and smooth, shaved so that there was not the slightest hint of hair anywhere other than on my head. My heart thumped wildly as I...Read On

20

My Oddesy 1 - Glen (here and gone)

A (mostly) true story of my first time dressing for another

"But mum. I'm too sick to go to school." I give my best fake cough. It was late senior year and I had been busting my balls for months. I just want a day at home alone. She finally replies after a minute of withering glares. "Fine. I'll call the school. But you're seeing a doctor Monday if this persists. I'll be back around five." "Sure. Whatever." I lay perfectly still until the sound of...Read On

18

The Worm Turns Part 2: The Routine

After establishing a routine, a surprise visit by a man took my tranformation to a new level.

Before I even realized it, we had fallen into a pattern of visits to the sisters’ salon. On a weekly basis, I was having my hair set, my nails done, and my make-up applied expertly by some combination of Kim and/or Kristie. Often one would do the work while the other recorded the proceedings on video or with a digital still camera. Several of the photos made their way onto the mirrors of...Read On

22

Workouts with My P.E. Coach

Courtney has a crush on her P.E.coach, Coach Cocker.

My P.E.coach, Coach Cocker, was a tall, handsome man. More than once when I saw him blow into his whistle, I wished he was blowing me. I was a seventeen-year-old tranny-in-training and I loved having a big handsome man sucking my dickie for me. So, it was only natural that I would want Coach Cocker sexually. I already liked flirting with him like the girls did. And I thought he liked me, too. ...Read On

10

Jason and Kym ~ Part Two

A story about self-discovery, now turns into a rollercoaster ride!

 Later that same night, I strolled down to my favorite watering hole to tip a few strong drinks in the hopes of either clearing my head or dulling the noises within. After flirting over those drinks with a short blonde haired gal named Kym, we stepped out onto the dance floor to press our bodies against one another to an old Jonny Cash tune. She’d been waiting for some guy to meet her for...Read On

29

Caught dressed like a sissy slut

My girlfriend was away for the weekend so I had the place to myself. I was feeling incredibly horny so I went through her knicker drawer and decided to dress up (which I've enjoyed many times before). I put on a really tight, pink thong, black fishnet stockings and suspenders, and her black mini skirt. I looked at myself in our full-length mirrored wardrobes. God, I looked so sexy and...Read On

24

Prom Date- Part 1

Jody is forced to dress as a girl for prom.

Jody was pretty much a typical 18 year old boy. He liked sports, hanging out with his friends, and playing video games. However, Jody had one deep, dark secret. He was addicted to wearing his sister's clothes. Every time the house was empty and he had the chance, he would sneak into her room and try on something pretty. Jody was always mortified of getting caught so he was very careful....Read On

17

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

17

She'll Never Know... (Part 1)

A young man discovers a taste for the finer things in his wife's lingerie drawer.

Once again they had argued before she went to work. The reason was also the usual one – sex. This particular morning Mark had woken unusually early, with his usual erection. Deciding to test Clare's mood, he had rolled over and nudged his naked penis against her, just after the alarm had gone. Letting his hand slide up her thigh, she had moaned gently and pushed back into him, letting his...Read On

21

My First Boyfriend Part Three

My boyfriend pimps me out to his friends

Steve and I had spent our first night together as a realcouple and in a real bed and it was wonderful. I had intended to wake him up with a blow job but he was already gone when I woke up so I had the whole day to wait for him to return from work. I spent the day just like a housewife would. I wore a house coat and some fuzzy slippers and after cleaning up the place sat down and watched...Read On

21

Friday Night Maid - Part 2

On Friday nights wife goes out with friends, he becomes the maid

Friday Night Maid Part II - by Diane Leonard As I finished folding his socks, he stood up and looked down on me. "Diane, remove my pants now, but do not get up after you do, just fold them and lay them on the edge of the bed." I reached up, removed his belt, and lay it on the bed. I opened his trousers and as they slid down his legs, I notice that he was wearing boxer shorts and...Read On

21

Adventures in a Woman’s Body – Chapter 3: Used by Strangers

I become their powerless cumslut

I put his softening cock back into his pants as he parked the car. He got out and I crawled up after him. Having been on my knees for so long, my knees were aching and my legs were sore, but at least my feet got a rest from walking in my seven inch black stilettos. “What’s your name, by the way?” I asked him, since I don’t know what to call him by. “Just call me your Daddy, sugarslut.”...Read On

12

Confessions of a Sex Crazy Cross Dresser Part 2

Chapters 3 and 4

Chapter 3: New York with Linda I didn’t really get a lot of time to think about what I had just done with Carlos. I fell asleep shortly after he left due to all the drinks I put away during the night. I actually fell asleep on my couch, still full dressed except for my jacket and shoes. When I woke up, I had a headache and was starving; I never even had a piece of the pizza Carlos brought....Read On

12

Pure Innocence

Well, maybe not...

It was an unseasonably warm Saturday and I decided to go out for a walk and clear my head. Instead of my normal guy garb, I decided to go out dressed as Aimee. But I was looking for a different look—totally cute and innocent which was not like me at all. I put on a little blue cotton dress, a pair of sandals, and donned a blond wig. The wig was long enough that I could put pigtails on...Read On

12

my first time

    I’m 28 now. I have been interested in women’s clothing as long as I can remember. I can remember when I was around 7 my sister caught me trying on a pair of her panties that I stole out of her room, I don’t think she ever told on me about that. As I grew I was always stealing pantyhose, dresses, skirts and etc from mostly my family and my friends sisters. I wasn’t really ...Read On

12

The Ultimate Fantasy

Paul enjoys his ultimate fantasy - an evening dressed as a bride

Paul couldn’t walk fast enough. His heart was pounding and he kept checking the time on his iPhone every couple of minutes. It was only a ten minute walk to the hotel but it seemed to Paul that he would never get there. He knew that Marie has something very special planned for him and he couldn’t wait to find out! The day started normally enough. Paul was up before anyone else in the house...Read On

12

Peer Pressure, Both Ways...

Girlfriend's boyfriend cums to the rescue!

"Fucking pervert, fucking pouffe, tosser, sissy...." Lenny had become accustomed to these names over the years, as he went about minding his own business, but the lads from out of town were relentless, as they began pushing and shoving Lenny. He tried to walk away, but they roughed him up a bit, before laughing hysterically and then shooting off. Lenny wasn't physically hurt, just a...Read On

12

My First Trip Out of the Closet

Crossdressing fun way over the edge

  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...Read On

12

Wet crossdressing fiesta M/M

Hot male on male cross-dressing action

Heading back through Texas I stopped off at the same porno shop in San Antonio, only this time I made sure to get myself a hotel room, because I already knew at that time I was going to get a man that night. I was in the mind set to please. Rubbing my cock all the way there until I got to the hotel room having it set up for wet sex. This time as well I remembered to shave my legs, dick...Read On

25

With the wifes help

wife takes me for my first gangbang

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...Read On

23

Adventures in a Woman’s Body – Chapter 2: Tease and Please

Things are happening under the table

After I got out of my house, I walked for about 20 minutes to get to this fancy restaurant I made reservations for. It was a long and tiring walk, but I loved cat walking in my sky-high stilettos and hearing the click of my heels with every step. I couldn't pay much attention to what was going on around me as I walked down the streets. I was focused on swaying my hips and crossing my heels...Read On

14

My First Boyfriend Part Five

I step out on my boyfriend and end up getting gangbanged

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...Read On

14

Jessie's Payback Continues

Jessie thought the payback was over. She was wrong

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...Read On