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Crossdressing

10

The Man In The Window - II

Love discovered; love discarded

Nick and Di were the last two diners in Luigi's trattoria, though the patron seemed unconcerned about them remaining so late. He wandered across to their corner table, placed two small glasses in front of them and poured a colourless liquid into each. "Compliments of the house signora e signore !" "You always know it's going-home time when Luigi offers you a free Grappa ," Di said with...Read On

28

Feminizing Henry, Part II

Henry is turned into Henrietta by his dominant wife Sally and her mother.

When Henry Fitzwinkle's wife Sally found him wearing her panties she lost all respect for him as a man, but he became more interesting to her as an experiment. Her mother, a dominant woman named Edwina, had turned Sally's father Joe into a panty-wearing sissy, and Sally had always been curious about doing that with a man. In Sally's profession as a lawyer she regarded most men as...Read On

27

Emmy's Games (Part 1)

Emmy takes control. Continuing on from the original encounter 'A Surprise Ass-Fucking in Panties'

“Put my panties on,” says the text message from Emmy. It is 9:30am and I have just woken up. I look across to the bedside table and see Emmy’s panties sitting there all dried out from last night's shenanigans. I lean over and pick them up, and can’t resist the urge to hold them to my face momentarily and savour their aroma. I do as the text message asked and put on Emmy's cotton panties....Read On

16

Prom Night

Having her boyfriend for the first time on prom night is special to a girl.

When I was in high school, I was seventeen-years-old and dating an older man. He was forty-years-old and very handsome. He had taken me out to dinner and for ice cream and for walks on the beach. We had held hands and kissed but had never gone any further, but I knew he wanted to go further by the way he looked at me when we were riding in his car. I would see him looking down at my sexy,...Read On

34

Feminizing Henry

Henry likes wearing panties, so his wife Sally feminizes him.

When Henry Fitzwinkle married Sally Blunt he knew she was a strong woman. She already had her law degree, and she carried herself like the aggressive three-sport star she had been in high school. In college she had been an all-star volleyball player, and with her blonde hair and muscular body she looked like a Nordic goddess. Henry was a small man, and when he saw this goddess walking...Read On

9

Sexy Stewardess on a Hot Flight: Part Two

The hot flight continues for Courtney.

My trip to Catalina with a handsome pilot and two of his friends turned out to be a working sex vacation for me. So far, I had already given a great blow job to the pilot, Phillip, on take-off. Then I sucked off his friend, Harry, who also sucked on my titties and played with my clitty dick through my white lace panties. Now, I was ready for the big prize, sucking Dick's big ten inch man tool...Read On

12

Becoming John Collins' Mistress - Part One

I get to know Mr. Collins and get invited to meet his friends

Hi. My name is Chris, though some know me as Christine. I am John Collins’ mistress. We care deeply for each other. John “keeps” me. He supports me financially and in return it is my pleasure to keep his sex life exciting, as well as entertaining any of his gentleman friends who drop over. It all began innocently enough, I suppose. I had just turned eighteen and had moved out from my...Read On

16

Rick Becomes Rikki, Chapter Two

Rick gets feminized some more, and has sex in a bridal gown.

There’s just something about wearing a bridal gown to make a man feel all girly inside. Up to now Rikki had thought he still had a shred of masculinity left, but the feelings that arose when he put on that bridal gown and minced about the shop were pure girl. He felt so soft and vulnerable, so tender and emotional, that he thought he could just cry. Of course, his mistress Sally had...Read On

15

Sexy Stewardess on a Hot Flight: Part One

Working as a tranny call boy leads to a high flying adventure.

After arriving in Los Angeles, I became a tranny call boy to support myself. Working for an agency, I was sent to perform sex on many older rich men. Being a hot twenty year-old tranny slut with fresh meat in my panties, I instantly became one of the more popular call boys in the agency. Some men even took me out on dates for dinner then back their places or motel rooms for lots of sexy...Read On

37
Tanksdad
online

Who Knew a Physical Could Be Fun

Discussing Lush had an added benefit.

I woke up grumpy. I couldn’t eat or pee this morning. I had a physical scheduled for first thing this morning. Even worse, the doctor had warned me that today I even got a prostate exam. Oh well, I hope his hands aren’t too big. I arrived at the doctor’s office early and waited for my turn. The nurse ushered me into the exam room and drew blood then gave me the little plastic cup I had to...Read On

36

A New Spin On Life

An Old Party Game Provides A New Experience

After spending my teenage years hiding my cross-dressingfrom friends and family, I was away at college and on my own for the first time. Jenny was a girl from my high school who was attending the same college. We had been good friends for years and I trusted her with my secret. In fact, she was the only one who knew. I started to spend time at her place when her roommate went home for...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

18

Meeting One of the Neighbors

I meet one of my neighbors and he invites me over for drinks.

Tom was almost seventy. We lived on adjacent streets and his property backed on mine. I had moved in only a couple of weeks earlier. I was renting the place. I was so excited to be on my own at last, especially because I loved to crossdress. My new freedom was exhilarating. One day I’d been in my back yard in the late evening, dressed in a cute white bikini. I was lying face down on a...Read On

14

Mindy fashionista

Part 3 of the Minday series - Cross dressing man hires Laura and Mindy for some girl fun

Laura’s escort business was becoming very successful, and she was able to pick and choose her clients. She shied away from any who she felt uncomfortable with, and she stuck to her rule of no sex, no matter how much money was offered. Her friend Mindy, who had escorted her on two of her “dates”, was so intoxicated with the thrill of exposing herself that she longed to be able to go into...Read On

28

Adventures in a Woman’s Body – Chapter 1: Plugging Up

Dressed up, plugged up, and ready for some cocks

After two years of hard work, I've finally come as close to being a woman as possible. The hormones and drugs that I've been taking for the past five years have made my body and voice quite feminine. With the help of toning exercises, I now have long slender legs, a soft and juicy ass, very feminine hips and a thin waist. My skin is very soft, smooth, and white thanks to the skin care...Read On

7

Hitch-hiking Baby Doll: Part Three

My cross-dressing cross country trip continues with my trucker stud.

When it comes to getting men to want to fuck her, a girl has to put her ass to good work. I discovered this when I was eighteen and first started being a tranny hooker around the adult book store. I was wearing my first miniskirt with a thong panty underneath, walking down the street. My ass cheeks were hanging out of the bottom of the miniskirt and men were slowing down to look at me, blow...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

15

Just For The Taste Of It

Vanessa is trained to love the taste of cum

Many years ago, before I was the experienced sissy girl I am now, I was living with a man named Jake. Jake took me under his wing. He wanted to help me become as girly as I could be. One of the things that he wanted to get me used to was the taste of cum. I had tasted it before, but only my own and his. Jake wanted to make sure that I was a cum expert. He said to me, “A true sissy...Read On

14

Allen's Sweet Surprise Part One

Seeing my boyfriend in ladies clothing is sweeter than I expected.

My pussy was dripping as I zipped my car into the parking spot in front of the mall. I was having another secret meeting with my boyfriend, Allen. Only, this time we'd arranged a little twist to our usual tryst. After years of Allen and I seeing each other, I'd finally worked up the nerve to share my fantasy of him dressing up like a woman for me. It wasn't easy for me to do. I'm a...Read On

8

Fucked in the Fitting Room Part Two: The Explosive Conclusion

When my lover finds a dress on the sales rack, I get more than I bargain for.

I took Allen's hard cock in my mouth and began to suck it slowly. "Oh, God," said Allen. I rolled my tongue around the tip of his cock and then ran it up and down the sides. "Suck it faster, babe," said Allen. I happily complied, bobbing my head up and down on his cock as fast as I could. I grabbed his balls in my hand and stroked them gently with my fingers. "Oh, baby, that feels...Read On

13

Fucked in the Fitting Room Part One

When my lover finds a dress on the sales rack, I get more than I bargain for.

My boyfriend, Allen, loves to wear women's clothing. It's something he's been doing awhile now, probably three or four years. We both get very excited about going to our local department store to hunt for new additions to Allen's wardrobe. Last night we had one such shopping trip and we both had a luscious time. "Grab a buggy," said Allen when we entered the store. "I plan to load up tonight."...Read On

9

My First Time Final Chapter

The conclusion of this story

The Friday that Lydia told me about had finally arrived and she would be bringing some of her friends over for drinks after work, and I was to serve them as Melissa. Lydia had also advised me that unlike the dominatrix persona I used during my first outing on Halloween, Melissa the maid, was totally subservient. That morning after my usual visit to the gym I cleaned the house and set up...Read On

9

Steve the Crossdressing Cat Lover

Cat lovers are a breed of their own and my boyfriend, Steve, is one of them.

My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please. Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land...Read On

26

My Boyfriend's Blue Silk Panties

a crossdressing shortie

My boyfriend, Allen, is a man's man. Let's get that straight from the start. He rides a Harley and he scoops me up in his big strong arms like I'm light as a feather (which I'm not...let's get that straight from the start, too). So it was a big stretch for me to ask my masculine lover to slip into a pair of silk panties just for me. It was a secret fantasy I'd harbored for years but had...Read On

51

First time sex with a man!

How my first time anal started and happened.

So there is this guy who I've been talking with for awhile. I wasn't too interested because I was still on the edge about meeting up dressed with another person. At the time I was under the influence and I sent him this message.   "I have recently been dressing up more as a woman as my family have been busy. I have been eating my cum all dressed up like a sissy! I have been eating my...Read On

22

The Wedding Present

Chardonnay wants to show her boyfriend and lover how committed she is to him.

Chardonnay had been Phil’s live in sissy lover and constant companion for just coming up to two years. She wanted to do something very special for him and had saved enough money at last. She phoned an exclusive hotel, giving great detail into what she required. She made a few more calls that afternoon while Phil was working. As she finished the last call, she gave a huge grin to herself in...Read On

41

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

19

After the Show

An invitation to a drag show proved to be an invitation to more.

I‘d met David through my (now ex) wife. He lived in the Twin Cities with his partner Dennis. His being gay made it very easy for me to talk openly about being Samantha. He hosted a drag show on Saturday nights at a small gay bar so he’d invited me to come along, meet the ‘girls’ and see the show. I could stay the night so I could go dressed and have a fun ‘girl’s night out’ while he MC’d...Read On

22

The Wrong Twin, Part Three

Excerpted from the diary of Francesca Hall

Dear Diary; Well, it’s been quite a month so far! Of course my big news is that my new boyfriend, Teddie, finally reacted to literally months of me flirting with him, and we finally “did it” last week at the Drama Club’s cast party for Our Town . We all had a blast at Mr. Stephen’s house and Mr. Stephen’s “girlfriend,” Sophie, gave me just an excellent face, with eye make-up to die for...Read On

28

Keeping A Secret

The drive home from the Cities was always long. After work I had stopped at Kim’s to change and emerged as Samantha. I drove to the meeting and then went out for a drink (or maybe two) with some of the other ‘girls’. By the time I was half way home my eyes just wouldn't stay open any longer. I decided to pull over in a secluded wayside rest area. If I could just catch a little catnap I knew...Read On