Crossdressing

trinitytowers

The Feminisation of Michael. - Chapter 7

The Feminisation of Michael. Chapter 7 I settled in at Stanmore House quickly and Sam helped a lot and we would spend most days together with her showing me around the estate. I soon persuaded Sam to wear prettier things and we were often seen., me blonde, her brunette, rushing around giggling in little floral dresses. Alternatively we would ride the beautiful horses in...Read On

Added: 24 Mar 2010 | Category: Crossdressing | Avg Score: 4.82 | Tags: | 5 Comments

DeedraCd

The Change Up

Sexy outfit gets Deedra some lucky action

Finally a break comes my way. The children are off to college, the wife has to go out of the country for two months on business. I can’t remember the last time we had sex. She used to dress in all types of lingerie for me. It helped me suppress some of my crossdressing desires. That stopped and my crossdressing started to grow again. What an opportunity for me, I can change up and dress...Read On

Added: 25 May 2012 | Category: Crossdressing | Avg Score: 4.96 | Tags: crossdressing  oral  anal  play  hermaphrodite   | 24 Comments

missunderstood98

My First Trip Out of the Closet

Crossdressing fun way over the edge

  I have wanted to write this story for many years but I hesitated to do so out of my fear of the unknown.   Since moving to Florida , I have pretty much been on my own for the first time in a long time. Let’s just say that now that I am older, I’m bolder! I no longer care who knows my sexual interests. It’s funny, because everyone I currently see understands my desires...Read On

Added: 13 Jan 2009 | Category: Crossdressing | Avg Score: 4.7 | Tags: walking on the wild side  

libertina

The Perfect Choice

A girl works to turn her boyfriend into her toy

Andrew had moved in with Hannah a few short months ago and so far everything was going just the way she wanted. She was an endless tease; wearing short skirts and dresses when they were out during the day or tiny shorts and vest tops when they were at home together. She did everything she could to turn Andrew on, and it was working perfectly.She hadn't slept with him yet and the tension...Read On

Added: 05 Jan 2013 | Category: Crossdressing | Avg Score: 4.81 | Tags: strapon  panties  femdom  feminization  sissy  anal   | 7 Comments

CourtneyFux

Adult Bookstore in My Hot Pants

Wearing a sexy pair of hot pants, I go looking for men at the adult bookstore.

After discovering that I enjoyed wearing sexy little panties, tasting cum and having a big vibrator in my ass, I began to have these auto-erotic sessions, every day.While wearing panties and playing with my ass with a dildo, I would lay in my bed and fantasize about all the big cocks I wanted to satisfy for men. While I was only 16 years-old, I had decided I was a daddy girl's and wanted to...Read On

Added: 09 Jan 2013 | Category: Crossdressing | Avg Score: 5 | Tags: crossdressing  exhibitionism  oral  anal  incest   | 9 Comments

kinkball76

My Unexpected First Time With a Man

How a night of anal play, and crossdressing turned out to be my most intense sexual experience ever!

In the Arizona heat... It was Friday, the first day that I would be alone at home while my wife was on her trip. It was also the day that I timed a delivery of some clothing and accessories for a weekend of crossdessing and anal play. As I sat at work repeatedly checking the status of two shipments, one was a box of dildo's, lube and anal plugs, and the other was filled with lingerie, a wig,...Read On

Added: 08 Oct 2012 | Category: Crossdressing | Avg Score: 4.78 | Tags: crossdressing   | 11 Comments

Karin

The Worm Turns Part 2: The Routine

After establishing a routine, a surprise visit by a man took my tranformation to a new level.

Before I even realized it, we had fallen into a pattern of visits to the sisters’ salon. On a weekly basis, I was having my hair set, my nails done, and my make-up applied expertly by some combination of Kim and/or Kristie. Often one would do the work while the other recorded the proceedings on video or with a digital still camera. Several of the photos made their way onto the mirrors of...Read On

Added: 22 Nov 2010 | Category: Crossdressing | Avg Score: 4.75 | Tags: crossdressing  blow job  beauty salon   | 2 Comments

CDinhiding1

Warehouse slut

There I sat at my computer, ready for another morning of chatting with my new online lover, much like all other mornings for the last two weeks.  It had become quite routine for us to chat for about an hour in the mornings, then off to our lives.  I was, quite honestly, starting to lose interest, figuring he was just another of the "Internet fakes".  We have all run into them, the guys who...Read On

Added: 01 Jun 2009 | Category: Crossdressing | Avg Score: 3.72 | Tags: | 2 Comments

cdbottom2

First Time, First Fuck, New Porn Star

A story I wrote while on a short break from my Missy series. Don't worry, I just need inspiration.

I am just a normal guy however I have what some would call an abnormal fetish. I am a 23 year old guy and I like to wear and dress up as womanly as possible. I am 5’9, a little chubby but can still pass as a woman, with brown hair, brown eyes and a 5 inch cock. One night I had gone out with one of my friends and had gone drinking to a few bars. As we went from place to place we started...Read On

Added: 10 May 2012 | Category: Crossdressing | Avg Score: 4.64 | Tags: anal  reluctance  toys  first time  gay male  crossdressing   | 4 Comments

trinitytowers

Felix becomes Felicity - Chapter 2

Life gets more girly for Felix!

FELIX  becomes FELICITY Chapter 2 My Mum and Sister went downstairs and I had a moment to myself looking in the mirror.  I didn’t recognise me in the reflection I saw a teenage girl, a very attractive teenage girl! I joined my Mum and sister downstairs. I was becoming better on the heels “Mum I have to reiterate that this all ends in 6 weeks time right?”, “Of course sweet that’s...Read On

Added: 23 Jan 2010 | Category: Crossdressing | Avg Score: 4.56 | Tags: crossdressing breasts   | 4 Comments

KrissyS

Adventures of Kristof and Marci - Part 1

After a long internet relationship, Kristof and Marci finally get together to explore their fetishes

ADVENTURES OF KRISTOF AND MARCI PART I The Meeting I sat on the chair in front of the computer, wearing a tiny black swing skirt, black nylons and red high heels.   Beneath the skirt I wore a little pale pink lycra thong and I was naked from the waist up, save for the chain that hung at my chest, the ends connected to each nipple by a little clip.   ‘I really need to pee’...Read On

Added: 26 Jan 2010 | Category: Crossdressing | Avg Score: 4.75 | Tags: crosdressing  spanking  watersports  fetish  

cassandrababy

Girls Night Out Part 2

Cassie and her friend's evening continues

Girls Night Out Part 2 Well everyone wants to hear about the second part of my night with Julie when I was in New Jersey. In case you didn’t read my first story, my name is Cassie, short for Cassandra (I also go by Sandy sometimes) and I am a cross dresser (CD). A while ago I was spending a hot summer night in New Jersey at a hotel with my friend Julie. We were attending a girl’s night out at...Read On

Added: 29 Jan 2011 | Category: Crossdressing | Avg Score: 4.92 | Tags: crossdressing  group sex  anal  oral   | 2 Comments

pornoperson

An Afternoon with Suzie C*cksucker

A Mistress directs a scene with two sissies

One of the strangest relationships I've had over the years was with awoman named Laura. She saw my profile on Yahoo and dropped me a note. It was like manna from heaven. She was very into the idea of fucking a man in the ass with a strap-on dildo. She'd not done it before but had fantasized about it for years. Would I be willing to help? You bet! We chatted for a long time before we...Read On

Added: 03 Mar 2010 | Category: Crossdressing | Avg Score: 4 | Tags: anal  crossdressing  oral  fellatio   | 1 Comment

trinitytowers

The Feminisation of Michael. - Chapter 4

The Feminisation of Michael. Chapter 4 Sue had replenished my wardrobe again with new work clothes and had taken the secretary theme to heart! The skirt suits had been replaced with pencil skirts and pencil dresses. The blouses had been supplemented further with lace and ruffle fronted blouses. There were also several ribbed tight fitting cardigans in black, red and various...Read On

Added: 10 Mar 2010 | Category: Crossdressing | Avg Score: 4.89 | Tags: | 3 Comments

Pudmeister

Crossroads

A young man explores his feminine side.

A crazy little story where a young man finds out if his hidden desires are what he really wants. This all started with my desire to see what it felt like to have big breasts. That's a little odd for a guy. I was a normal heterosexual guy who dated some in high school and now that I was in my mid 20's I found myself at a crossroad. A couple of years ago I had decided to...Read On

Added: 21 Sep 2009 | Category: Crossdressing | Avg Score: 4.9 | Tags: crossdressing  oral   | 5 Comments