Crossdressing Stories

11

thatfemininUrge

How Easy It Is.

Until you dress En-Femme, you will not discover how easy it is for a woman to get sex.

I have gone through a few phases of crossdressing. The first phase was my private phase in that I did it at home, alone; to satisfy my feminine urge. The next phase was could I go out in public and pass. When that phase was accomplished, I needed to know if I could not only pass as a woman, but more importantly could I make a man aroused. These phases were not just a need but also a evolution...Read On

9

vote

Maid2frill

Meeting Mistress Sarah

This story, although fiction, is dedicated to Mistress Sarah, a real person who I lost.

My heart pounded fiercely as I stood at the door to Mistress's house. I did not expect to be so nervous at meeting her again. After all I had known her for quite a while now. Mistress Sarah had been gracious enough to allow me back into her world. I was fortunate to fall under the control of such a dominant woman. She had moulded me into an obedient and submissive slave through the use...Read On

6

vote

SxyJackyLeggs
online

Dreams come true. Part 1

A dream trip thanks to my Queen.

Here I am, tied up and being fucked by the biggest and first cock I've ever had. "How did I get here?" I think to myself and begin to think back on how this came to be. *** Today is Thursday and I see a huge box at my front door. Knowing that I'm not expecting anything my curiosity has the best of me. I take it in and open it to find two more boxes and an envelope. I start with the...Read On

3

vote

stockingluvr

An Introduction To Crossdressing, The Finale

As Jackie, Chandra and I finished up our food, we chatted about the evening yet to come.

Reliving our evening’s events had Jackie and Chandra pretty worked up. “You girls seem to be getting a little excited," I stated. "Are you ready for some more fun?” Simultaneously they both grunted, “Yes we are!” I leaned across the table to find them both holding the others cock and slowly working each other into a frenzy. “You should probably save some of that for back at the...Read On

24

vote

tnbiguy4men

Crossing A Different Line

A married family man's growing interst in female lingerie leads to his being taken as a woman.

In my personal journey from straight, married heterosexual to bi male, I discovered, along the way, that I was aroused by women’s lingerie. It started with trying on a pair of my wife’s nylon panties. The feel of the silky material, and the sight of how it fit, quickly brought on an erection. I used another silky pair in my hand to jack myself off, being careful not to get any cum on the...Read On

21

vote

tvk3983

Pam's First Time

Jerry is a friend from way back and meets Pam while looking for his friend, Kevin

Just a few days of spring break left and I was planning on making the most of it. Well, the most for me anyway. I'm a crossdresser and I have been for a long time. All through high school I'd secretly dressed, slowly building a wardrobe of pretty panties, a few skirts and blouses, bras, my silicon boobies, and most importantly, my shoes. The most important thing I had going for me, at...Read On

7

vote

tvk3983

Carolyn Makes Her Way (part 3)

Business is booming and so is his hand on her ass!

Once I dragged my tenderized ass out of bed, tender because Mike had used a cane on me last night, I dressed in pantyhose, a navy blue, loose skirt, a cream colored satin blouse, black pumps with four inch heels, and a bra. After applying my makeup I took a look at myself in the mirror, making sure I looked good enough to conduct an interview at the leather goods store we were opening in just...Read On

19

vote

CourtneyFux

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

20

vote

qt_sis

The start of my life as a submissive crossdresser

First forays into crossdressing and giving handjobs

I am a bisexual cross-dresser/sissy and have been enjoying my life as such for many years. It all began for me when a friend asked me to look at some of his 'girlie' magazines. We went up to his bedroom and looking through the magazine got Chris really excited and he got his cock out and started to masturbate. I couldn't take my eyes off his cock and I slowly reached out and touched it and...Read On

9

vote

Spooge

Not Crossing The Line

Crossdressing brings me closer to a woman than I expected

When I was a kid I had a book called, ‘What Do People Do All Day?’ It made a start at teaching me about the variety of jobs that exist in the world. As an adult I feel it would be equally beneficial if there was a book as simple as that one which answered the question, ‘Why do people do the things they do?’ Part of the trouble is that I often do not even understand my own...Read On

5

vote

tvk3983

Carolyn Makes Her Way (part 2)

Mike paddles Carol - Hard!

After I left the office of my former employer I went immediately to see an attorney. There were two things I had to do: one see about suing the hell out of my former employer and two: I needed to get my name changed legally to Carolyn instead of Carl. I chose this attorney because I already knew him, very well in fact, right down to the birthmark above his nice cock. He wasn't surprised to...Read On

Added: 05 Aug 2015 | Category: Crossdressing | Avg Score: 4.8 | Words: 7,595 | Tags: cd bondage spanking oral anal pee

8

vote

thatfemininUrge

Look up at Me

It is in the title

After my romp with Daren and him taking me to a whole new level for me to fulfill my feminine urge, I discovered that my sexuality to being accepted and taken as a woman had sky rocketed. It also gave me a greater level of confidence when I was dressed En-femme. For weeks, I had played the whole encounter with Daren over and over in my mind, and soon realized that I was about to hit my...Read On

7

vote

JessieCD

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

14

vote

Bunny12

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

7

vote

tvk3983

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

13

vote

Bunny12

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

16

vote

CourtneyFux

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

7

vote

tvk3983

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

13

vote

ThePhantom
online

Discovery

Kyle is discovered indulging in his secret passion.

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

4

vote

JessieCD

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

10

vote

ThePhantom
online

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

15

vote

thatfemininUrge

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

9

vote

JessieCD

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

27

vote

ralphbranca

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

3

vote

tvk3983

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

10

vote

bikerbear600

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

10

vote

tvk3983

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

3

vote

simar

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

7

vote

JessieCD

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

21

vote

bikerbear600

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

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Popular Tags

Crossdressing

How Easy It Is.

Meeting Mistress Sarah

Dreams come true. Part 1

An Introduction To Crossdressing, The Finale

Crossing A Different Line

Pam's First Time

Carolyn Makes Her Way (part 3)

My New Boyfriend

The start of my life as a submissive crossdresser

Not Crossing The Line

Carolyn Makes Her Way (part 2)

Look up at Me

Jessie Caught in the Act

He's So Pretty In Pink

Carolyn Makes Her Way (Part 1)

Sissy Slut Gets All His Holes Filled

The Frederick's of Hollywood Lingerie Model

Carolyn Makes Her Way

Discovery

Jessie's Office Interlude with Sue

Once Again in silk, The Conclusion

My feminine Urge Satisfied

Jessie and Sue's date concludes

Just Needed A Drink

Jenny Learns Her Place (Part 2)

The Next Night - Crossdresser: Part 2 of 2

Jenny Learns Her Place

Simran - A Crossdresser: Part 3

Jessie And Sue's Date Continues

First Time With A Crossdresser: Part 1 of 2