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Crossdressing

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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

8

A Terrific Threesome: Part Two

The fun threesome gets kinky in the bedroom.

When I told Sherry about the handsome maintenance man with the thirteen inch cock, she said, "He sounds delicious." I explained how he caught me wearing her panties and wanted a blow job right away. How I offered him a beer and a blow job and what a good fuck he gave me, too. We felt like two girlfriends talking about a big stud we both wanted badly and we were both very happy. "Oh,...Read On

An Unexpected Love Story

What was supposed to be a night of dressing turned into a night of making love.

I was so looking forward to Friday. My latest order of lingerie was scheduled to be delivered and knew that I would have some time after closing to try it all on. I own a small business and I work alone on Fridays for this very reason, it gives me time to indulge my secret passion. Getting dressed really helps me relax after a stressful week and have a back room where I can also take pictures....Read On

16

Jenny and Mike: Date Night

A loving husband and wife begin a long weekend of crossdressing and pegging.

It’s Friday night, but for me and my wife it’s Date Night. Most couples have date nights on Saturday, but we have it on Friday nights to get an early start on the weekends. Michelle and I have been married for a little over two years now and we live a very happy life. I was not always so happy because I am a crossdresser and have been dressing up ever since I was 16. I met Michelle when we...Read On

8

In Her Shoes Part 2

This is the second part of In Her Shoes so to fully understand what’s gone on

please read the first part. After a short time of resting my feet on Peter’s bum I now slipped my foot back rubbing the sandal against his balls and cock. His knees started to widen slightly as I teased I could see his balls quickly rise up and tighten as they had before. His cock was now straight along my foot and his body was rocking back and forth in time with my foot. I could feel...Read On

7

Sissy sperm bank

I started the morning my favorite way, really the only way I know how: with my bull's big cock between my lips. This was one of those nice slow blowjobs that he liked to start the day with. I made it especially wet for him today, slobbering all over his thick shaft while lovingly looking up at his eyes. I grasped the base with my dainty hands and licked the head like a lollipop while smiling...Read On

8

Allen's Sweet Surprise - Part Two: The Yummy Conclusion

When my boyfriend dresses in ladies clothing I'm in for a sweet surprise.

I felt a light tapping on my bottom. "Mmmm," I said. It felt kinda good, this mysterious spanking. "You can open your eyes now," said Allen. I opened my eyes and turned around. "Meet Kandi," said Allen, blinking her lush eyelashes and smiling at me sweetly like a schoolgirl. Kandi had stunning electric blue hair and dazzling green eyes. She was sporting a pink polka dot skirt that...Read On

2

My 2 AM Phone Call (Part Two)

I became a perfect motel whore that night.

My day started around 2:00 a.m. with a phone call from a Black man I knew from an intense relationship that started in a video store theater several years before. After using me as he pleased for several months, he suddenly dropped me and just vanished until this morning when he called and gave me very specific instructions where to come, what to wear and when to arrive. That is why I...Read On

8

Call Me Julie Part 4

Julie is not the only one in for a surprise.

Scott coaxed me out of the car and we walked the ten feet to the front door, he was practically dragging me while reassuring me that everything would be alright. "Kelly is expecting us, don't you worry about a thing." "She is expecting me? Dressed up like this? Somehow I don't think you are telling me everything Scott, if this ends badly I will be kicking your sweet ass," I told him. ...Read On

9

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

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

10

Fantasy Meets Reality at the Peep Show

A crossdresser's fantasy comes true

I pushed my way through the purple curtain to the cashier’s booth. He looked up from his newspaper and asked me how many tokens I wanted. I figured a stack of twenty would be enough to complete my mission. I’d been there several times before but this would be my first time taking things further. My heart was beating fast as I scooped up the tokens and made my way to the viewing room. As...Read On

12

My Good Friend Pete (Part 2)

In order to enjoy this story, I advise the reader to read "My Good Friend Pete."

From where I stood, I could hear the crunching of gravel under Pete's feet, as he made his way to the front door. I took half a dozen deep breaths, waiting for the doorbell to ring. I didn't have to wait long. "For fuck sake, pull yourself together man." I actually caught myself smiling in the wall mirror. "...or is it woman!" One of the most difficult things to achieve...Read On

15

crossdresser confession part 1

I really loved my wife; she was the most beautiful creature I have ever known. Tall, brunette and the longest legs you have ever seen. Myrtle's beautiful face is framed by her gorgeous brown hair. She was about 5'8" and had a great ass. Her curves were soft and very feminine, not a big chest but nice and perky tits I loved to play with. She would drive me crazy when she donned a pair...Read On

9

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

10

The Magician's Assistant or How it began - Part 1

Ken had led a pretty normal life until the year his longtime friend needed an assistant for his growing magic act. Magic had always been a hobby with his buddy Carl and he spent many a day watching him perform a new trick in his garage seeing if he could detect the secret. Their being forced to take woodworking classes in high school really paid off when Carl expanded into the realm of...Read On

0

Becoming John Collins' Mistress - Part Two

I'm invited to spend a day with one of John's hunky friends

The next day, everyone was a bit hung over. I needed to pick up my car, which I’d left at the bar the night before. Joe said it was on his way and he’d be glad to take me. I borrowed a raincoat from John to wear over my skimpy outfit, then Joe and I headed out. Joe was making eyes at me during the drive, and I decided it would be best to come clean. “Joe, there’s something you...Read On

5

Jenny & Mike: A Day out

Role Reversed day of shopping, a dinner date and pegging at the movie theater.

I woke up in the morning with Michelle’s arm around me. We were spooning. She was the big spoon. I held on-to her arm stroking it gently as I recalled how ‘Mike’ and I had gotten it on in the living room the previous night. ‘Mike’ had fucked me on numerous occasions in the past, but my ass was still sore after what we had gotten up-to last night! God it was so hot! I turned my head to look...Read On

11

Carl, Carla and Hannah - Part 7

Claire starts work at the office as Carla continues her voyage of discovery into femininity...

I switched the six-thirty alarm off with a groan and turned to cuddle Hannah. After our customary two minute huddle, I kissed her and then wearily got out of bed. Without thinking, I sat down on the toilet and relieved my bladder, and then took off my bra and panties before stepping into the shower. The soothing warmth of the water managed to ease some of the ache in my body from the...Read On

10

How Andrew became Andrea Part 3

Andrew leaned back on the couch feeling the warm cum had just let loose in his panties beginning to cool and a stain become visible on his slip. "Looks like you will have to clean up and change," Lacy said with a smile. "Looks like," Andy responded. "Shall I pick out something or would you like to?" "I would like you to." Andy headed to the bathroom where he removed his cum...Read On

7

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

10

My First Night Chapter 2

The second chapter to my night with Marie

Previously She also included in this bundle of sissy goodies, sheer black thigh high stocking and black three-inch wedges. My legs were so high and my body so curvaceous, my soft red lipstick tied in with the red baby doll. She had placed a blonde wavy wig which I tied into my hair with grips and styled with a middle part-in. Marie also supplied red nail varnish and some very...Read On

10

The girl with green hair

An extra-special birthday surprise

"Is this cab taken?" Languorously, she lifted her green mascara-clad eyelids and gave a half-smile. "'Fraid so." I'd left the party in the local wine bar and decided to get home before I passed out. I was feeling pretty squiffy. Two taxis cruised by with their engaged signs on. It began to spit with rain. I looked through the back window of the parked cab. The interior light was on....Read On

4

Lovers in the Afternoon

Once upon a time, on a quiet afternoon.....

Through the scrim curtains, the soft afternoon sun lights the room with a pastel glow. I sit at the chair in front of the dressing table, quietly smiling to myself. I finish putting on my make-up; a light touch of lip gloss. I look at myself in the mirror. Quite good I think. I am getting better all the time. I can feel the tension and excitement in my body. My perfume fills my head. My...Read On

16

Becoming Chloe - Part 7

Vickie and Chloe go for a ride...

I awoke to find the bed next to me empty. Disorientated, I turned over and dozed until I'm awakened by the smell of coffee and Vickie walking through the door with breakfast. All she's wearing is her thin bathrobe, through which her full breasts and nipples are clearly visible. Her hair is dishevelled and she has the most wonderful smile on her face. She looks adorable. "I thought you...Read On

9

Crossroads Ch.3

He has to find out if this is what he wants

A tale of pure fiction and fantasy. I was actually considering going all the way. Going all the way in becoming female. I had been living as a female in all phases of my life for some time. I continued on the hormones and all my desires said I should do this. I had called the plastic surgeon who had done my breasts and explained what I wanted. She suggested going to see a doctor...Read On

3

Sissy Blane's Liquid Assets

A Sissy is forced to repay a debt to a sex club in trade

I became familiar with the Plumrose Dossier one cool February morning when it was read to me in the private rooms of Madame H at the Clinic. ***** I'd arrived that morning for my weekly 'therapy' and had only enough time to hang up my outer clothes in the Sissies' cloakroom and don my Eva Gabor wig before a facilitator poked her head in and told me I was wanted in Madame H’s office...Read On

6

CD Domina training two slaves

CD Mistress commands two slaves for a hot 3-way.

Just five days had passed since my last session with my slave Candy and already I was yearning for his sexy body again. I was in need of another meeting and had something special planned for it. I called Candy's phone and just like previously he answered before it could ring twice and greeted me anxiously. "Hello Mistress Cheyenne," Candy said as he answered his phone. "Hello slave Candy,"...Read On

9

Porn Star Babe: Part Two

Time to get the lttle sluts on the set for some hot tranny action.

Being a sexy girly boy about to make her debut as a porn actress with two handsome, well-hung studs was so exciting to me. And having my friend, Chrissie Licks, along to show me how it is done was especially re-assuring. Chrissie and I were naked and about to get into our sexy lingerie for the shoot when Summer Cox, another hot tranny porn star, came to help us with our hair and make-up....Read On

6

Christina and Cheryl - Part 3

Christina encourages Cheryl to go out with a little help from her friends...

I woke up naked being spooned by Christina. Her smooth arms held me tight against her. I turned around and woke her up with a kiss. She opened her eyes and kissed back before pushing my head down. I kiss down her body and slipped her pink panties off. I kissed up her thigh and edged closer towards her clitoris, this is how we spent most mornings. "No, my ass." I lifted her legs allowing...Read On