Crossdressing

jimymac

Date with my wife

It started with my love of sexy lingerie. I planned a date with my wife. She was to come home from work and go up stairs to clean up. Once all cleaned up she was to put on the outfit I laid out. She had lots of questions that I wasn't answering. She wasn't to come into the rest of the house until she was dressed. Well my day started by going to the store shopping for dinner and an outfit....Read On

Added: 24 Jun 2012 | Category: Crossdressing | Avg Score: 4.86 | Tags: wife  role playing  crossdressing   | 8 Comments

CourtneyFux

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

Added: 31 Oct 2012 | Category: Crossdressing | Avg Score: 4.86 | Tags: crossdressing  exhibitionism  oral  bisexual   | 7 Comments

LoriAnn_CD

becoming LoriAnn - Part 6

Last minute preparations for our night with her husband Max!

Nikki and I got together one more time before we set her plan in motion. We had to make sure we were on the same page, that Max would have the ultimate night of his life and we had to spice up Nikki's wardrobe. Nikki was a beautiful woman, slim and sensuous, but a bit conservative in her dressing. So we made a date to go shopping. We started at Victoria's secret. We bought contrasting...Read On

Added: 01 Dec 2012 | Category: Crossdressing | Avg Score: 4.86 | Tags: oral  bi  anal  couple   | 2 Comments

Amatramp

Caribean Vacation part 2

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

We strolled down the hall to the elevator. I did not notice what floor we went to, as I was so pre-occupied examining my sexy self in the reflective surface of the elevator. We got off the elevator and walked down the hall to a door marked 469. “This isn’t the dining room,” I objected. “No, this isn’t,” she replied as she knocked on the door. “Who’s room is this.” I asked. Before...Read On

Added: 02 Nov 2010 | Category: Crossdressing | Avg Score: 4.86 | Tags: panties  crossdressing  anal sex  humiliation     | 3 Comments

anotherfeeling

Put it on!

A not-so-reluctant housemate dresses for his live-in landlord

I was living and working in London, my first job after college. No chance of having a place of my own with these crazy house prices and this being my first job at the age of 23, so I rented a room from a guy older than me, in his mid-30s. His name was Steve and he was a masculine type, split up from his wife but seeing a feisty Spanish woman called Manuela. There were big arguments now and...Read On

Added: 16 May 2011 | Category: Crossdressing | Avg Score: 4.85 | Tags: first time  housemate  crossdresser  anal   | 17 Comments

SashaCD_ThongPanties

My first halloween night as a teen CD!

My first time i dressed up like a chick and how lucky i got that whole night

This is halloween!! A day that everyone goes out and dresses up in costumes and other things, and go to parties and drink and show off their wild side until the wee hours of the next day. And I thought to myself, since everyone goes out and wears costumes, why not dress up myself into something wild and willy?? Or in fact, why not dress up in a manner of expressing who I am and what I...Read On

Added: 13 Nov 2009 | Category: Crossdressing | Avg Score: 4.85 | Tags: thong  shower  crossdressing  anal  creampie     | 2 Comments

mredd

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

Added: 11 Aug 2012 | Category: Crossdressing | Avg Score: 4.85 | Tags: dressing room  mall  lingerie  panties  oral sex   | 16 Comments

Angelia

The Party

It happened one halloween

I am a closet cd. It was Halloween. My wife called from work and said she wanted to go to a party at a friends house. It was a costume party. She said she had a costume and I was to wear one as well. What, I don’t have one. Yes you do, your going as a girl. But I’ve never done this. Well you’re going to tonight. No one will care because it’s a costume party so get dressed...Read On

Added: 19 Jan 2009 | Category: Crossdressing | Avg Score: 4.85 | Tags: crossdressing  anal  blowjob   | 12 Comments

GirlyWorld

Dressmaker's Dummy

Girls always knows best

I was happy now that Kasia and I had moved in together. Not only did it mean that we no longer had to take turns going to each other’s place, but it also meant that I had closer access to a supply of her soiled panties. Kasia was a cute Polish girl, 23 years old, with deep blue eyes, shoulder-length hair trimmed in a cute bob, and a body to die for. We had decided trying to live together to...Read On

Added: 04 Aug 2010 | Category: Crossdressing | Avg Score: 4.85 | Tags: crossdressing  panties  tease  self-discovery   | 7 Comments

Amatramp

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

Added: 25 Sep 2010 | Category: Crossdressing | Avg Score: 4.85 | Tags: panties  exhibitionism  crossdressing  lingerie     | 11 Comments

trinitytowers

The Feminisation of Michael - Chapter 3

The Feminisation of Michael. Chapter 3 I endured the rest of the afternoon with continued suppressed sniggers and laughter. I was glad when 5.00pm came and I buttoned up my jacket and put my handbag over my shoulder and left with a big sigh of relief. Sue was waiting outside in the car. “Hi Michaela,” she greeted me. “How did it go honey?” she beamed. “Fucking awful!” I blurted out....Read On

Added: 17 Feb 2010 | Category: Crossdressing | Avg Score: 4.85 | Tags: | 3 Comments

cdbottom2

Telling Mom I’m A Crossdresser Part 4: Repeat Business and Roleplays

4th installment of Missy :) please rate and comment :)

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again. Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also...Read On

Added: 25 Feb 2012 | Category: Crossdressing | Avg Score: 4.85 | Tags: crossdressing  roleplay  anal  oral  toys  group sex   | 7 Comments

Km44

Wife's crossdressing fantasy Part 3

I had to find a way to repay my wife for the wonderful anniversary gift she game me.

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. My Wife's Cross dressing Fantasy 3 Then my wife looked at me and said “Happy anniversary darling.” How did she know the effect this experience would have on me. I was changed forever. It was such a wonderful experience. She deserved that I come up with something just as exciting for her,...Read On

Added: 10 Dec 2012 | Category: Crossdressing | Avg Score: 4.85 | Tags: crossdressing  oral  anal  group sex   | 8 Comments

dougysweet

First Time Fantasy

Fantasy - The Dom, the sub and the bi-virgin After all these years of being in the closet, I finally believed that it was time to move from fantasy to reality. Years have gone by of me wanting more but not being ready to step out and experience things for myself. My stockings ran and my lingerie started to collect and time and time again, I purged and replaced more than one collection...Read On

Added: 14 Dec 2012 | Category: Crossdressing | Avg Score: 4.85 | Tags: fantasy  crossdress   | 9 Comments

Chrissy_CD_slut

Chrissy Gets Bolder Meeting Todd Again

Chrissy gets a good hard fucking by her new friend

I really hadn't expected Todd to call me after that night. I know how guys are when the night is getting short and you need someone to satisfy your needs. I did think about him a few times and wanted to see him again. I had enjoyed my first experience with a man so much it seemed that's all I could think about was my next cock. When I went to class I would catch myself looking at guys as...Read On

Added: 21 Oct 2011 | Category: Crossdressing | Avg Score: 4.85 | Tags: anal  reluctance  creampie  crossdresser  gay  bisexual   | 7 Comments