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Crossdressing

Our crossdressing (cross-dressing) stories feature tales of either gender (usually male) dressing up in the clothes of the opposite sex, for reasons of sexual gratification. Crossdressers are akin to the transvestic fetishism, which is a sexual fetish for the clothing of the opposite gender. The crossdresser can be of any sexual orientation.

6

Jessie Caught in the Act

After Jessie and Sue's office interlude, the boss catches them in the act.

Sue and I were starting to catch our breath from our office session when suddenly someone started knocking on the door. “Jesse! You’re late to your meeting with me! What in the hell was all of that noise coming from your office? I sounded like someone was having sex in there!” Now I knew I was going to get it. That was my manager Steve. Steve burst through the door and his mouth...Read On

3

Discovery 2

Arm in arm we walked down the hallway with my heart beating wildly with anticipation. I demurely stood at the door of Rusty's room and waited while swiped his key card and then held the door open for me.  He bade me to have a seat on the small couch while he poured us glasses of wine. After handing me one he sat down next to me and we touched glasses. He saw that my eyes were fixed on the...Read On

10

He's So Pretty In Pink

Poor sissy's desires go wanting.

He is sixteen years my junior, six feet tall, blond haired and blue eyed, with an insatiable desire to be my submissive sissy slut. I never could figure out what drives his desire for an older woman, such as myself, but he can never keep his eyes off my long legs or my round, voluptuous ass. He pestered me to no end to dress him as a proper sissy and take his hungry ass with my strap on and...Read On

6
Recommended Read

Carolyn Makes Her Way (Part 1)

Carolyn meets her co-worker and the sparks fly.

After tucking my penis and balls away, I started dressing with the basics: panties first, a sheer yellow thing, then my bra with the silicon helpers we girls so love and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of how it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long sleeve...Read On

11

Sissy Slut Gets All His Holes Filled

Desperate sissy slut boy gets what he wants.

He was waiting for me as instructed, dressed in the bag of clothes I had left for him earlier in the week. I entered the motel room to find him sitting on the bed in the mini skirt, sheer blouse, lace topped thigh high stockings and stiletto heels from his goodie bag. With his legs crossed, he appeared to be quite demure but I knew the desperate, horny slut that was raging beneath the...Read On

13

The Frederick's of Hollywood Lingerie Model

Courtney's first job in Hollywood is as a Frederick's lingerie model.

When I first arrived in Los Angeles, I was staying at a motel on Sunset Strip in Hollywood. I had plans on working as a tranny call boy there. In the "L.A. Express" magazine, I saw an ad for a club on Sunset, called the Leather and Lace Lounge, that was popular with trannies and the men who liked them. I decided to go there and learn more about the tranny scene in Hollywood. It was three in...Read On

6

Carolyn Makes Her Way

After getting fired Carolyn moves in with Mike

After tucking my penis and balls away, I started dressing with the basics, panties first, a sheer yellow thing, and then my bra with the silicon helpers we girls so love, and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of house it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long...Read On

11

Discovery

Kyle is discovered indulging in his secret passion

Discovery, one of the greatest fears I have. All others take a backseat to my fear of being discovered indulging in my passion. You see, I am a cross dresser. Like so may others I don't know where this desire to dress up came from, but soon it was too strong to ignore. I started out with pilfering a few items from my sister's room and wearing them behind closed doors when the house was...Read On

5

Jessie's Office Interlude with Sue

As Jessie's first date with Sue ends, now it cums down to the office...

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...Read On

8

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

11

My feminine Urge Satisfied

My feminine urge took me to a new level at transforming myself into a sexy woman.

I had a three day weekend for me to dress en-femme, and so I took advantage of it. I was not looking to do anything other than dressing, behaving, and acting as a woman. I was content to just relax and be feminine at home without any expectations. I don’t know why I felt as such, except that I needed just to enjoy being feminine and doing so alone. With that in mind, when I got home...Read On

10

Jessie and Sue's date concludes

Jessie's date with Sue cums to a wild conclusion!

I could not believe I was going out with Sue on a date. It was our first date and she appeared to be my match made in heaven. First, we got caught with my face between her thighs while wearing lingerie in a department store dressing room. Next, we made our way to the shoe shop where not only did Sue buy me a killer set of four-inch heels that were strappy, brown open-toed sandals with...Read On

15
ralphbranca
online

Just Needed A Drink

I didn't know what kind of bar it was.

My travel plans had been totally messed up. Weather was to blame. A huge pattern of thunderstorms sweeping up the East Coast had screwed up more than a hundred flights, including mine. As a consequence I got into Boston about five hours later than I'd planned on. I was tired, irritable and, well, generally quite unhappy about life. The cab ride to my downtown hotel was uneventful but the...Read On

4

Jenny Learns Her Place (Part 2)

Jenny prepares to accept her Master

“Thank you, Master,” I said as I slowly brought myself to my feet, tears of pain rolling down my cheeks. I couldn't see my ass but it was probably purple with bruising and I was happy with that. Bobby would now know that I could withstand a hard spanking with the paddle without falling back on the safe word. “And for good measure,” Bobby said and put the clips back on my nipples. Wincing...Read On

7

Special Delivery 2

Anna remembers that she has my panties...

When I woke the following morning, I laid in bed for a long time, staring at the ceiling and thinking. Without a doubt, Anna’s discovery and willingness to use it against me resulted in one of the most powerful sexual experiences of my life. Even now, still wearing the panties, my cock stirred just from the memory. Bending over to lick my cum off of her ass was an especially clear recollection. ...Read On

9

The Next Night - Crossdresser: Part 2 of 2

The next night and a second session with Jenny.

I woke up early from the sunlight shining through the windows. We’d forgotten to close the curtains when we collapsed into bed last night. Jenny was already awake and watching me.  ‘I was just about to wake you up with a blow job,’ she smiled. ‘Funny, I was thinking of doing the same to you!’ I laughed. Jenny kissed me then turned around in the bed to lay on her side so our cocks were...Read On

11

Jenny Learns Her Place

Jenny submits to her lover's desires

His hands held my hips tightly and his very large hard cock slammed into my asshole again and again, as if he were was going to ram it all the way out my mouth. I whimpered with each long stroke while my own small dick dripped the remains of my orgasm. It was amazing that he was hard so quickly after pumping my mouth full of sweet jism, some of it even spraying onto my face. “Oh! Oh! Oh!...Read On

2

Simran - A Crossdresser: Part 3

Not much sex but a turning point in Simran's life.

After that rather eventful evening with Ram, I opened up to my fears and inhibitions. Now performing on cam or coming out dressed in front of an online crowd was something I could do easily. I still covered my face, since I wasn't yet ready to reveal my identity. As far as I remember, it was a couple of weeks after my interaction with Ram that I heard a commotion outside the house. I...Read On

6

Jessie And Sue's Date Continues

Sue takes Jessie shoe shopping, and more...

Sue and I had a great time in the lingerie section of the department store. Getting caught by the sales clerk was definitely not something we planned on happening, but in some strange way it added a whole new dimension to what we had done. Both of us got out of the store as quickly as possible and headed into the mall. Sue suddenly turned to the right and stopped at a shoe store. This...Read On

14

First Time With A Crossdresser: Part 1 of 2

Scott looks for something different after his divorce and finds Jenny

I’m Scott, 36 years old and recently divorced from my wife of 12 years. It was an amicable split with no kids to complicate matters. We sold up, divided everything two ways and went on our merry way. Our sex life was good and regular but a little boring. We stuck to the same three positions – missionary, her on top and spooning. I’d give her oral but she wasn’t that keen on going down on...Read On

9

Dressing Jaymee - Chapter 4 - Going Out

Jaymee Cate takes to the streets

Cate walked out of the bathroom and into the suite. She poured them each another glass of wine and headed over to the window. It was dark out but the city was busy and full of lights. The hotel was on a main road and looked over a series of bars, restaurants, and clubs. There were several large apartment buildings behind the bars and Cate started to scan the lit windows. She watched as...Read On

4

An Introduction to Crossdressing, Pt. 6

As our evening progresses the fun continues.

After Steven leaves me at the table with Jackie and his new friend Chandra, I start to fill them in on the details. I tell them, “It’s really Jackie’s fault that I got fucked so good; since he was being so aggressive with his dance partner, I got jealous and grabbed Steven’s ass.” Then I continued with, “This led to Steven grabbing mine beneath my skirt, and then stroking my cock and balls...Read On

18

Memoirs of a Crossdresser: Chapter 1

My True Story Chapter 1:  I was a kid when I first discovered women's underwear. I loved the way it made me feel. I had a friend who I'd play the normal games that kids play with, and I would always be the girl character. We were children, so nothing out of line went on, but even at a very young age, I had felt an attraction to femininity. There was something that made me feel like I should...Read On

6

An Introduction to Crossdressing, Pt. 5

My first time at a not-so-straight club is friendlier than I imagined.

As Jackie and I pulled up to the club my mind was racing. My main concern is whether we look passable, and that if we don’t, that we might be laughed at and teased. As I expressed my concerns to Jackie, he said, "Remember that we are at a place for people like us who are a little different." As his statement sinks into my thick skull, all my anxiety starts to slip away. For the first time in...Read On

9

Once Again in silk Part 2

As sundown approached on Saturday I showered and got ready to attend the opening of an art gallery that a member of our organization was sponsoring. I selected the suit, shirt and tie and then I retrieved the white silk panties from the laundry room. I wonder if Darlene questioned herself on the fact that I accepted her request without protest? They were beautiful and just running my...Read On

36

Special Delivery

My special delivery was given to her by mistake

My apartment complex is one of those boring, corporate, cookie-cutter types where the layouts are identical and maximized for renting. I had been there for about a year when Anna moved into the apartment next to mine. Right away she made sure I knew that she had a boyfriend, and did she ever! His name was Kevin, and he was tall, muscular and exceedingly arrogant. I did not like him, and...Read On

9

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

15

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

12

Erica Loves It (Part 1)

Erica discovers sex

For my entire life, I've always thought it was so unfair that girls gotto wear all the really cool clothes. They were softer material, better color choices, and looked so much better. In fact, when I was very young I wore dresses whenever I got to play with the girl next door, but that was always for the tea parties and such we liked to have. But by the time I discovered sex and masturbation...Read On

28

Becoming Mary - Part I

A girl discovers her dominance while a guy discovers his submissiveness

Lucy and I had been living together for a couple of months when it all started. She was in her early twenties, and I was a couple of years younger. Up until I moved in with her, I’d lived my parents. My stay-at-home mother had taken care of all the household chores while my father went out to work. It was the typical old-fashioned family structure. From day one, living with Lucy was proving...Read On