Crossdressing

TinaTim

First Night Nerves

Nervous Tim becomes Tina and loses her virginity

My name is Timothy. I live in a large city in the English Midlands with my girlfriend Debbie. We are both 22 years old and have lived very happily together for over three years. We both work in a call centre for a large financial organisation. I am not tall – 5' 4" on a good day – and have always been very slim. I am blonde with blue eyes and very fair skin. Debbie is two inches shorter than...Read On

Added: 09 Jun 2013 | Category: Crossdressing | Avg Score: 4.86 | Tags: cd  crossdressing  virgin  anal  seduction  first time   | 7 Comments

cdbottom2

Telling Mom I’m A Crossdresser Part 7.5: Amateur Pole Dancers

I thought I would try something a little different and involve more teasing to my story. enjoy :)

After our time at the spa, I spent a lot of time in my room trying out all the new sex toys we got from Richard and Monica. They were all exciting in their own ways and I came so much with each one. Some vibrated, some went deep and some felt good stretching my ass wide. The feeling of all the sensations I could get from my new plastic and electric friends were amazing and found myself...Read On

Added: 18 Mar 2012 | Category: Crossdressing | Avg Score: 4.58 | Tags: crossdressing  pole dancing  teasing  masturbation  toys  milf  voyeur   | 3 Comments

Karrenfuchmee

Karren Gets Fucked and Sucked

Sex is abundent in this story

Adventure in Nylon 3 Part 1 Karren gets Fucked and Sucked He was all dressed up in his finest outfit. Starting with the prettiest white lace panties he owned. A white lace teddy with attached garters, a built in under wire bra that was filled with breast shaped silicone pads to look and feel like the real thing. He covered these with a silky smooth full white nylon slip. His shaved legs...Read On

Added: 09 Oct 2012 | Category: Crossdressing | Avg Score: 5 | Tags: dressed  first time out  threesome   | 3 Comments

sarahsully

Yes Captain

The crew gets a little closer than normal

It had been a while since Sarah had a lover. She was aching to slip into something sexy and get a man going. She had been to a few clubs but found nobody that could fix her needs. That was until she arrived at work on Monday. Sarah was a copilot for a major airline. She entered the cockpit and met the Captain John. He was a good looking man. Tall, blonde hair, and a smile that would melt...Read On

Added: 29 Oct 2012 | Category: Crossdressing | Avg Score: 3.89 | Tags: flight attendant  captain  stewardess  crossdressing  sarah   | 2 Comments

cdbottom2

Telling Mom I'm A Crossdresser Part 17: Seven Days Of Sex, Days 1, 2

Part 17 of Missy, Sorry this is long but i hope you will like it.

This is a fairly long story but I broke it into two parts so that you can read the first half in one sitting and find your place easier if you want to come back and read some more. Also, I would like to say that this will be the start of a seven day sexcapade for Missy involving two of her past flings. Please enjoy and rate and comment at the bottom. Happy reading!! ;) It was now Monday...Read On

Added: 04 Sep 2012 | Category: Crossdressing | Avg Score: 4.75 | Tags: crossdressing  gay male  group sex  anal  oral sex  interracial  exhibitionism   | 4 Comments

LoriAnn_CD

Becoming LoriAnn - Part 3

LoriAnn takes another step towards becoming the slutty gurl she wants to be

I was enjoying my new found sexual freedom. My first steps were slow and easy but nothing felt more exciting than discovering the feel and taste of a new hot, hard cock. The boys at school never really bothered me about regular sex and long as they got to shoot their big hot creamy loads down my throat or all over my tits, and I was happy each time I was able to swallow one of those...Read On

Added: 27 Nov 2012 | Category: Crossdressing | Avg Score: 4.75 | Tags: oral  anal   | 5 Comments

MistressCheyenne

Crossdressing Domina gets a new slave

A new slave drives a crossdressing Mistress wild.

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels....Read On

Added: 29 Jun 2012 | Category: Crossdressing | Avg Score: 4.7 | Tags: slave  crossdresser  tranny  bdsm  domination  anal  oral   | 3 Comments

trinitytowers

A Nanny Femtastic! - Chapter 11

A NANNY FEMTASTIC! Chapter 11 We walked to the harbour and found the boat. There were too bulky security guards checking people as they entered. The boat was in fact a massive cruiser! We joined the queue, it was obviously not a little gathering. The other women were dressed in classy whites and float summer dresses, we looked like too cheap hookers! “Trinity this was a...Read On

Added: 18 Feb 2010 | Category: Crossdressing | Avg Score: 4.83 | Tags: | 4 Comments

ThePhantom

My First Time - Part 2, or The Beginning

Once was not enough

It was about two weeks after Halloween that the dreams began. I began to dream about being transformed again. I was able to recall the feel of the silky garment against my skin, the sensation of the nylons brushing against each other as I walked. I recalled all the women at the party who danced with me and rubbed my silk covered ass. "You feel like a real girl," more than one said, and I...Read On

Added: 08 May 2013 | Category: Crossdressing | Avg Score: 4.47 | Tags: nightgown  nylons  thong  heels   | 7 Comments

trinitytowers

A Nanny FEmtastic - 9

A NANNY FEMTASTIC! Chapter 9 Thomas quickly pulled his hand from under my skirts, and stood up abruptly. “Fucking hell I don’t believe it!” he blurted out. Felicity was suddenly by my side. “What’s wrong?” she said. “forget it!” Thomas said, and stormed back inside, knocking over the table and drinks as he went. Bradley chased after him. I burst into tears and Felicity put her...Read On

Added: 12 Feb 2010 | Category: Crossdressing | Avg Score: 4.82 | Tags:

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

Pudmeister

Crossroads Ch.4

Another chapter in this fantasy tale of a young man's journey into becoming who he is.

  I am on an airplane flying to Vancouver. I have an appointment with a doctor to have sexual reassignment surgery. I am so excited I can't stand it. I know this is what I want. My recent encounter with a woman convinced me. I have no doubt about it now and won't look back. We land and as we deplane I notice, as always, the admiring looks I am getting from men, including the pilots. I...Read On

Added: 25 Oct 2009 | Category: Crossdressing | Avg Score: 4.38 | Tags: | 1 Comment

biguy2play

My Lesbian Lover

My first adventure out as a woman ended in the arms of a woman!

My wife was trying to come to grips with the realization that I cross dressed, with marginal success. Part of her plan was for me to meet in the Twin Cities with other CDs so I could have a ‘safe’ place to dress up, away from our small town. To be safe, I was to drive up, change clothes there, meet with my friends and then change again for the drive home. A good plan … a safe plan … but not...Read On

Added: 22 Oct 2012 | Category: Crossdressing | Avg Score: 4.67 | Tags: oral  crossdressing  fucking   | 4 Comments

irishfella

A Valentine's day I will never forget - part 2

A sequel to my previous story

In my last story I was sucking my mom's plastic cock when my next surprise arrived at the door. When the bell rang my mom left, leaving my on my hands and knees wondering what my next surprise was. Even though my mind was going a 100 mph, my mom took her time to return with my surprise. When my mom returned she was being followed by a tall, muscled man with a grin on his face. My mom just...Read On

Added: 27 Aug 2012 | Category: Crossdressing | Avg Score: 4.83 | Tags: anal  valentines day  strip tease  blow job  strip club     | 1 Comment

Karrenfuchmee

Karren Gets Sucked and Fucked Part 2

It gets hotter for Karren, Nancy and Kevin

Karren followed Kevin to his home in her own car so if she had to leave she could do so at her leisure. Karren wondered what Kevin's wife looked like, would she like the idea of a man dressed like a woman making love to her? Would she like sharing Kevin's cock with another man dressed as a woman? She hoped everything would turn out for the best.  Her thoughts were arousing her cock; she...Read On

Added: 13 Oct 2012 | Category: Crossdressing | Avg Score: 5 | Tags: wife  crossdresser  sex  cum   | 2 Comments