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Crossdressing

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40

Gang banged at a private club

This is what happened when a friend took me to a private members only gay, bi, and transgender party

After yet another hot weekend at my friend Heberto’s house, I was packing up and getting ready to go home when he told me he had something “special" in mind for us next weekend. I begged him to tell me what he had in mind but he refused. So I left. My curiosity was peaked. The week dragged on thinking about all of the possibilities. The anticipation was killing me. Finally Friday...Read On

40

A new friend

As I had a nice, big empty house I did what any good 17 year old would do. That first weekend I had a massive house party! I took a night off from dressing up and invited everyone I knew and when it came to the big night there were plenty of people, including a few I didn't know. I chatted to people and made new friends, sharing drinks and having fun. There was one girl there in particular...Read On

39

The Adult Theatre

A true story with the name and location changed for a good lush friend.

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...Read On

38

Tammy, Lisa, and Karen part 1

This is my first story so please give me some feed back.

It was Friday and the first thing I wanted when I got home was a nice warm bath to clean off the day's hard work. I filled the tub with hot water and added some bubble bath. I shaved my legs and underarms. As I slid under the hot water I looked at my toes peeking through the bubbles, and realized I needed to reapply some polish. After a long soak I got out, dried myself off and went to...Read On

28

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

23

Caribbean Vacation part 1

Lost luggage leads to wearing girlfriend's panties as a swim suit and more

Susan & I often traveledto the Caribbean for our vacations. We loved the laid back atmosphere and all the sun and gorgeous beaches. Last year though we arrived to find that the airline had lost my only bag containing all my clothing including my swim suit! Imagine arriving in the Caribbean without even having a swim suit to wear! I had just resigned myself to going down to the gift shop...Read On

23

A Fantasy to Remember

Halloween was rapidly approaching and my girlfriend of 2 years was planning something big. She had been a stripper for 10 years and was as kinky as they come. She and I had done a lot, so only a few of her fantasies were left unfulfilled. She had already had women and men, group sex, bondage, been a submissive and a dominate. We had a no holes barred policy. I could have any hole I...Read On

23

Where do I begin? Chapter 1

Young man lets his inner woman out during an encounter with an older man.

Where do I begin? I’m normally not very open about my private life, seeing as I grew up under the pretense that secrets are meant to be secrets. However it seems I have come to a point where I am comfortable with who I am and where I have been. Comfortable enough to bare to you all my deepest secrets. Deep breath in, slowly let it out. My name is Alicia, well that's my new name, my old...Read On

23

Two Girls Are Better Than One

My girlfriend sets me up with other men we share.

My girlfriend, Sherry, had nice, big C-cup titties and a face like a young Marilyn Monroe. Needless to say, she got hit on by lots of men wherever she went. She was also a nyphomaniac who liked to be fucked ten times a day, so we had a great sex life. She found out I enjoyed wearing lingerie, so, as part of our sex play, she would dress me up in her panties and bras and stockings and...Read On

16

Busted by a bud

Caught on home turf.

It's a hot summer day in 1994. Nowhere is a small, fairly poor, rural Illinois town; the kind of town where nobody locks their doors. Summer seems to be an average 19 year old. He goes to a small community college and works on the weekend's. He's kind of quiet and doesn't like to be around his parents. Both parents have jobs where they have to work the night shift. Summer's mom works for...Read On

16

The Sexy Girl-Next-Door: Part One

Wearing too many sexy clothes gets Courtney a big cock inside her.

As a sweet sixteen-year-old boy, I started my life of having transvestite proclivities. Being sexy for men and making their cocks hard for me became my favorite thing to do for pleasure. I already had a boyfriend, the blonde college boy lifeguard at my community swimming pool. He had seen me wearing some sexy little hot pants and come on to me, one day. The fact that he was handsome and all...Read On

16

Deann Finds Out

Deann finally works up nerve to go out in public

Jimmy sat up in bed and felt the dry cum on his belly from last night's masturbation. A quick look at the clock told him his parent's had already left for work and their weekend trip so he knew he had nothing to worry about. The plans he had for the day could begin right now. Stepping out of bed, he padded to the bathroom and began the process. A long shower began the day. He made sure...Read On

16

Carl, Carla and Hannah - Part 2

Hannah gets the upper hand.

I awoke to the sound of running water. Hannah was in the shower, leaving me alone in bed. A dull ache in my backside reminded me of what had happened last night: Hannah had tied me up, blindfolded me and then fucked me using a strap-on. She had called me a bitch and a slut as she held my legs over her shoulders and pounded me like a whore. And, apart from when she forced me to swallow my own...Read On

44

Total Sub CD Slut

His total sub CD slut

I could not wait to get home from work on Friday. My routine was the same. It was total preperation for the weekend. I was a highly placed executive with the company I worked for at the time. Nobody knew that I lived as a total sissy slut cock worshipping whore on the weekends. I was seeing a guy who was very dominate. I met him online. The first night he took me home he dressed me...Read On

27

The Meter Reader

Caught Wearing My Bikini

I'm basically a 'city boy' but one summer decided to rent an old two story farmhouse in the country. It had its good and bad points. The bad was that it was quite a way from town. I was working nights at a bakery and had to drive the twenty or so miles to work in the dark every night. The good part was that it was secluded. I could walk around the house in just my bra and panties, a short...Read On

22

My First Taste of Cock

Tammy blows and swallows her first cock.

After fantasizing for so long about what it would feel like to dress as a slut and suck a cock, I decided it was time I tried the real thing. I posted an ad on Craigslist with a couple of pictures of me dressed, asking for someone to let me dress for them and swallow their load. I got a lot of responses and most of them just sounded creepy except for Matt. Matt was 36 (I was 25) and a hot...Read On

22

A friend with something extra.

Ian makes a discovery about his boyhood friend.

So here Ian was standing in the doorway to his buddy's room and staring at this drop dead hottie clad in silk, lace and heels that he found inside. It was just a typical Friday and he'd dropped over his friend's house for a pizza and movie night. It was a rotating event for them on Fridays. They didn't have their own cars as of yet and had no desire to walk to the mall and hang out....Read On

22

Curious No More

I used to call myself bi-curious, but now I know!

I began dressing in my sister's clothes. I would get so hard and excited when I felt the soft panties against my cock and the bra wrapped tightly around me. But my dress up time was always short. Now that I live on my own I have my own femme wardrobe and plenty of time to dress and perfect my makeup and appearance. The more I dressed and the longer I stayed dressed, the more I wondered what...Read On

15

Jessie's Fantasy: Chapter 6 Turning the Tables

Now that Jessie fooled his friends, who will turn the table on whom?

I was floored by what Tracy had said to me. “Because, the male Jesse is no more for the time being, it is womanly Jessie that needs to go.” It seemed that my love just told me that I had to meet up with my male friends tonight. My mind was going a mile a minute. I already fooled my friends once. But can I do it again? If I do, what is going to happen? What will I let happen? My stomach felt...Read On

15

In Wonderland, Pt.1

Costume mandatory...

When I was in high school I was always very camp, which was probably why almost all of my friends were girls. This was definitely why I first ended up crossdressing. I was sixteen and round one of my 'girlfriends' house for a few drinks on Halloween before we went to a house party nearby. I never much cared for Halloween, so just came as myself. When I came in they all sighed since I wasn't in...Read On

15

Crossroads Ch.02

A young crossdresser take things farther.

The second chapter in this crazy little tale. I really loved my little adventure out as a woman. I liked the power I had over men. I was seriously thinking that I would like to live as a woman full time. That would be quite a commitment and one that would change my life forever. As I said before I worked for a really liberal company and one day I got up some courage and went to...Read On

15

A Sweet College Girl In Love

As a sweet college girly boy, I dated a real big hunk with a ten inch cock.

I went to college in a beach town in California where all of the girls wore their little thong bikinis to the beach and showed off their asses for boys with very friendly results. I noticed that when the girls were bending over while playing volleyball in their little thong bikinis, the boys all looked at them with hungry eyes that I liked a man to have for me.  The sweet little college...Read On

15

my first date with Ben

I had been chatting with Ben online for a while and we had talked on the phone several times before I decided to meet with him. I had met him through Craigslist so he knew what I was all about from my ad. We arranged to meet at restaurant for an early dinner so there would be plenty of people around. That Saturday, I spent my time getting ready. I showered and shaved smooth and used a...Read On

15

First Night Nerves - Part 2

Tina agrees to meet Barry without 'the girls'

I sat by myself on the bus, my briefcase on my knees, counting the stops and wishing it would go faster. Since Barry’s text message last night and his surreptitious call to my mobile that morning, I had been so excited, planning what I would wear to please him most. Debbie hadn’t heard the beep on my phone so didn’t know that I would be meeting him without her that afternoon. So far I had...Read On

10

Confessions of a Sex Crazy Cross Dresser Part 4

Chapters 7 and 8 of Book #1

Hi Everyone, I hope you like these chapters, please let me know if you want the next two. Chapter 7: Triangle of Fun I slept great that night with a full stomach of drink, food and Peter’s cum. I woke up on Friday and thought this is going to be a hell of a weekend. I played around with my cameras and had finally figured out how to use the self timer on the 35mm and how to use all...Read On

10

My First Time - Part 3

The story continues...

As Lydia had promised, on the first day of her vacation I got my first lessons in high heels. It took most of the day before I was able to walk across the room and not fall on my face, and these were only a moderate heel. I took her to dinner to celebrate and, at her request, I wore the satin thong under my jeans. Lydia could not resist reaching out and squeezing the bulge in my jeans,...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

10

Learning To Be Submissive - Part 2

My second meeting with Jack

I arrived slightly earlier than I was meant to. After our first meeting I had been given specific instructions. Jack had allowed me to shower and change back into my normal clothes. Once I had returned to the kitchen, I found a note with a key. "Today you excelled yourself, but you have more to learn. Next week on Monday you are to come directly here after you finish for the day. I will...Read On

10

My date with Ben part 3

I was invited to Ben’s house for dinner Saturday evening and spent the day getting ready. His wife Susie was looking forward to meeting me again and getting to know me better. I was unsure how the evening was going to go, but I decided that I was going to try and enjoy it as much as possible. I spent the afternoon getting ready, and shaved smooth all over, hoping that Ben and I would get to...Read On

10

Once Again in silk, The Conclusion

Darlene meets Melissa

As soon as I got home from the gym on Sunday, I headed to the closet and removed all the boxes containing Melissa's things. They had been cleaned and packed with great care so they looked as good as the day they had been purchased. I then inspected the makeup case and its contents seemed to be in great condition as were the contents of wig case. When Darlene said she wanted to meet my...Read On