Crossdressing

susi_swallows

The Awakening of Susi

Susi discovers the joys of anonymous cock sucking at a glory hole (true story)

Ever since I can remember I have loved being feminized and being made to wear very slutty clothing. This is a true story of my first experience at a glory hole and a coming of age for my sissy self. I had many female friends who loved to dress me up in their sexy clothes and strut me around in front of their boyfriends. They thought it was cute to see me in full makeup and a wig wearing a...Read On

Added: 05 Dec 2012 | Category: Crossdressing | Avg Score: 4.82 | Tags: glory hole  sissy  crossdresser  submissive  cum dump  exhibitionism  public sex   | 11 Comments

CAPITALLETTERJ

Dirty Little Me

Caught, with panties on and my pants down...

Rushing around all day, it seemed like this was starting become a ritual for my Fridays but this particular Friday I would never forget!  Waking up late as usual I flew out the the door as fast as I could, not giving any thought to what I had done the night before. As usual my boss wasn't too pleased but I never really minded his attitude because everything he lacked in personality he made...Read On

Added: 15 May 2013 | Category: Crossdressing | Avg Score: 4.82 | Tags: gym  locker room  older  panties   | 6 Comments

libertina

My Girly Fantasy

A night with my friend changes everything between us

I wake up and smile, remembering where I am and who I'm with. I'm warm and comfortable, wrapped in your arms as you sleep. I think back to last night, finally showing you my girly side. We've been best friends for ages but I always had a crush on you. Finally, drunk on wine, I decided to do something about it. I came into the living room we share and straddled you; taking off my robe to...Read On

Added: 07 Feb 2012 | Category: Crossdressing | Avg Score: 4.82 | Tags: gay  crossdressing  panties  anal  boyfriend   | 6 Comments

trinitytowers

Felix becomes Felicity - Chapter 5

FELIX  becomes FELICITY Chapter 5 ..My Mum and David had announced their impending marriage with a ceremony planned in about 6 weeks time. No guessing who was to be bridesmaids. The week before we were due to start back to school Jasmine mentioned at breakfast that Thomas wanted to take her to the cinema that night and that they had talked about a foursome me with Bradley .  “Not...Read On

Added: 28 Jan 2010 | Category: Crossdressing | Avg Score: 4.82 | Tags: | 1 Comment

gloryhole31

Pumped While Wearing His Pumps

Hitching A Ride with the Lothario of Lingerie

What a place to be stuck! Under a sign that says Coors Road and practically dying of thirst. I was now two-thirds of the way across the United States but perhaps the most difficult portion of my cross-country hitchhiking adventure lay ahead. It is all deserts from there on the outskirts of Albuquerque to the Pacific coast, my ultimate destination. I had left from Maine four days earlier...Read On

Added: 19 Apr 2012 | Category: Crossdressing | Avg Score: 4.82 | Tags: anal  bisexuality  fetishism  exhibitionism   | 1 Comment

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

AndicdnSC

Andrew to Andrea - Part 3

..the next step...

 BRRRRIIIIIIINNNGGGGGGGGGG!!!!!! The alarm clock that my wife and I mockingly referred to as “Baby Ben” sounded off and pulled me from what I first thought was a great dream. As my senses slowly came online, I could feel my hand laid over my naked wife’s breasts and that I wasn’t in my usual gym shorts and t-shirt. I was surrounded in silk, and it was not unpleasant, but it was a floor...Read On

Added: 04 Aug 2011 | Category: Crossdressing | Avg Score: 4.82 | Tags: crossdressing  straight/bi   | 5 Comments

1ball

Mistress Hannah's Pathetic Husband Part 5

I serve lunch to sorority sisters

I was making progress as a slave but unkown to me, one of my stories helped Mistress Hannah see an opportunity for a particularly fun afternoon and a chance to help an old friend through a rough spot in her marriage. Several months of aerobic classes and feminization had increased my stamina and made me more comfortable when we spent our Sunday evenings out for dinner and as member/patrons at...Read On

Added: 27 Oct 2011 | Category: Crossdressing | Avg Score: 4.82 | Tags: humiliation  strapon   | 4 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:

watcherfun

All Dressed Up Part 3

The story continues...

I spent the next few days thinking over what had happened to me. Had I really enjoyed it? Over time however I began to forget about my little 'excursion'. Months past and my trip had lodged itself at the back of my memory to be forgotten. The story doesn't end there though... There came a time a few months later, where I was running low on cash. I had spent too many nights out...Read On

Added: 17 Sep 2010 | Category: Crossdressing | Avg Score: 4.82 | Tags: office  crossdress  teen  young  crossdresser  mini  skirt   | 4 Comments

1ball

Mistress Hannah's Pathetic Husband Part 4

Mistress takes the humiliation to a new level

The third and final day of my transformative weekend started poorly. I had aches and pains all over. My neck and back and thigh muscles were sore. I had a little irritation from body hair that was growing back. And of course, my asshole felt all stretched out and very tender. I wondered if it would ever feel tight again. I also wondered what the evening would hold. I couldn't imagine that...Read On

Added: 24 Oct 2011 | Category: Crossdressing | Avg Score: 4.82 | Tags: humiliation  feminization  humor  beads  strapon   | 2 Comments

Km44

Wife's Crossdressing Fantasy

My journey from boy to man to woman

This is a work of fiction. Any resemblance to persons or incidents is coincidental. My adventure began while I was a senior in high school. My mother took me to the dentist. It was late afternoon and shortly after I was called into the examination room the receptionist and assistant went home. The dentist then closed the door of the room we were in. He walked over to me and started making...Read On

Added: 29 Oct 2012 | Category: Crossdressing | Avg Score: 4.81 | Tags: crossdressing  wife   | 9 Comments

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

cindytranee

Cindytranee meets the maintenance crew

Cindytranee gets caught crossdressing and gets fucked by three men

This is a true story that happened a few years ago when Iwas living in an apartment complex while looking for a house. I had taken a small one bedroom on the 2 nd floor. It was very nice and private and I really enjoyed being there. This was the first time in years that I had lived alone and I loved it. It gave me the freedom to enjoy my favorite thing, cross dressing and having sex with as...Read On

Added: 04 Apr 2011 | Category: Crossdressing | Avg Score: 4.81 | Tags: oral  anal  orgy  crossdresser  inerracial   | 9 Comments

cdbottom2 online

The Slut Within

This is my first story. If you like it please comment and I will write chapter two :)

I was 22 years old at the time, and I had been crossdressing for a few years. For some reason I could never control my desire to put on women's clothes and prance around my apartment looking all sexy and slutty. Normally I can never decide what specifically to wear as I like to change it up all the time, from wearing latex lingerie to sexy roleplay outfits and beyond. I am 5'9 with a...Read On

Added: 29 Jun 2011 | Category: Crossdressing | Avg Score: 4.81 | Tags: group sex  fetish  bdsm  spanking  toys  first time  interracial   | 11 Comments