Crossdressing

baldie

My First Time

Fist time oral

This a fantasy of mine and my first story that I am submiting. For a long time I had thought about oral sex with another man. I was married a few times and it never really satisfied me completely, I loved sex with them but I longed for sex with a man. I had wondered what it would be like to find a man looking like a woman, I talked to female friend and she helped me to dress up like a sexy...Read On

Added: 05 Dec 2010 | Category: Crossdressing | Avg Score: 4.88 | Tags: oral  gaymale  crossdressing   | 6 Comments

cindytranee

Bo Peep and the neighbor

crossdresser role play

It had been a hot summer and I had no luck finding a job. My parents did not seem to understand that there just weren't that many companies hiring that year due to the economy so they had really been pressuring me to find a job. They all wanted someone with experience but having just graduated high school I had none. I was nearly at my wits end so when I was asked to house sit for my uncle...Read On

Added: 27 Apr 2011 | Category: Crossdressing | Avg Score: 4.71 | Tags: oral  anal  spanking  role play   | 5 Comments

duke1933

Halloween

Boys will be boys

This story is not to be copied or moved to another web site Well here it is Halloween and I have an idea to dress up with my older bro and take the two younger bros out to trick or treat. When the big night came I got some of my sisters things to dress up in. I took all I needed to look just like her with the panties bra and skirt and blouse with a short jacket over it all. I must say...Read On

Added: 12 Nov 2008 | Category: Crossdressing | Avg Score: 3.89 | Tags: hot halloween for two   | 1 Comment

Kelsie

The Ultimate Fantasy

Paul enjoys his ultimate fantasy - an evening dressed as a bride

Paul couldn’t walk fast enough. His heart was pounding and he kept checking the time on his iPhone every couple of minutes. It was only a ten minute walk to the hotel but it seemed to Paul that he would never get there. He knew that Marie has something very special planned for him and he couldn’t wait to find out! The day started normally enough. Paul was up before anyone else in the house...Read On

Added: 30 Jun 2010 | Category: Crossdressing | Avg Score: 4.55 | Tags: wedding dress  bride  smoking  mutual masturbation   | 3 Comments

AmandaK

An Unforgetable Experience

Caught By The Best

I will never forget the day Carrie enter my secret world. It was the summer I was 17, I had been dressing my sisters clothes since I was about 8yo. In more recent years I had started buying a few of my own clothes and lingerie nylons and make-up. It was a Saturday and I was home alone and decided it would be a good day to dress and be girlie, excited about my day I waxed my legs and bikini...Read On

Added: 01 Aug 2009 | Category: Crossdressing | Avg Score: 4.44 | Tags: basement   | 4 Comments

AndicdnSC

Andrew to Andrea (Part One)

Andrew is about to really see the other side

Hi, I'm Andrew; at least I was Andrew full time until about a month ago. I have always been fascinated by lingerie: its feel, its appearance, how it just makes a body look that much more sexy. Like most curious types I started young (at sixteen, so not all that young), swiping what I could from my sisters or cousins when I could and squirreling my prizes away until I could find time for them....Read On

Added: 29 Jul 2011 | Category: Crossdressing | Avg Score: 4.53 | Tags: crossdressing  straight/bi   | 9 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   | 8 Comments

misssiberia

A Tale of Two Clitties

A notice posted on a bulletin board in an adult bookstore leads to a white hot sexual encounter

A Tale of Two Clitties One day I was checking out the bulletin board in a local adult bookstore. My eyes danced across the listings. Dungeon masters, couples looking for a third, but then I stopped, there it was, "Lonely virgin crossdresser seeks same". My heart jumped in my chest, and my cock twitched in anticipation. I tore off a tab with her number and promised my feminine side I'd call. ...Read On

Added: 19 Apr 2010 | Category: Crossdressing | Avg Score: 4.92 | Tags: crossdressing  transvestites  anal sex   | 13 Comments

Aimee_Cd

Pure Innocence

Well, maybe not...

It was an unseasonably warm Saturday and I decided to go out for a walk and clear my head. Instead of my normal guy garb, I decided to go out dressed as Aimee. But I was looking for a different look—totally cute and innocent which was not like me at all. I put on a little blue cotton dress, a pair of sandals, and donned a blond wig. The wig was long enough that I could put pigtails on...Read On

Added: 15 Nov 2010 | Category: Crossdressing | Avg Score: 4.44 | Tags: panties  masturbation   | 5 Comments

summer1979

Busted by a bud

Caught on home turf.

It's a hot summer day in 1994. Nowhere is a small, fairly poor, rural Illinois town; the kind of town where nobody locks their doors. Summer seems to be an average 19 year old. He goes to a small community college and works on the weekend's. He's kind of quiet and doesn't like to be around his parents. Both parents have jobs where they have to work the night shift. Summer's mom works for...Read On

Added: 29 Aug 2009 | Category: Crossdressing | Avg Score: 4.71 | Tags: crossdressing  anal  friends     | 3 Comments

AshleyBarnes888

A Night Out with Suzanne

Young man decides to support his new girlfriend's fetish and finds out a lot about who he really is

I hadn’t seen Suzanne in 15 years. She was a member at the country club where my father had worked and, despite living in separate towns, we saw each other every summer. We enjoyed each other’s company and we spent most of our days playing tennis and swimming at the pool. When I graduated from college and went into the Army, the thoughts of Suzanne were just faraway memories. Then,...Read On

Added: 07 Sep 2011 | Category: Crossdressing | Avg Score: 4.96 | Tags: crossdresssing  oral sex  straight sex  dressup  makeover   | 21 Comments

nicole77

Mike's new girlfriend

It started as a typical Monday really; I waved my wife off to work and then went upstairs for a long bubble bath and shave, as I stood drying myself and rubbing baby lotion into my body my cock started to grow as I got excited about the morning ahead. I quickly put on sweat pants and then raced to the outbuilding at the back of the garden to fulfil my cross-dressing desires. I opened...Read On

Added: 17 Apr 2012 | Category: Crossdressing | Avg Score: 4.8 | Tags: sissy  anal  submissive     | 15 Comments

LingerieBoy

Number Off A Bathroom Wall

Back in highschool I got a job working at the local mall at the Sears store. I was a stockboy and all around general gopher. I would always wear sexy outfits under my work clothes. On my second day I was asked to clean the bathrooms and I did. I started in the womens room,kind of hoping I would stumble onto a pair of panties or something,but no luck. I then work my way over to the...Read On

Added: 25 Jul 2008 | Category: Crossdressing | Avg Score: 4.67 | Tags: | 5 Comments

1ball

Mistress Hannah's Pathetic Husband Part 2

The transformation begins

During my first week as her new slave, Hannah decided that I was too hairy for a little sissy boy, so I had to begin removing hair from the tip of my nose down. The mustache went first. It really was kind of pathetic anyways. I actually got compliments from some of the women at work about how handsome I looked without it. I had grown it because I had a "baby face" and I wanted to seem...Read On

Added: 18 Oct 2011 | Category: Crossdressing | Avg Score: 4.73 | Tags: humiliation  sissyboy  panties   | 6 Comments

Toby

Wet crossdressing fiesta M/M

Hot male on male cross-dressing action

Heading back through Texas I stopped off at the same porno shop in San Antonio, only this time I made sure to get myself a hotel room, because I already knew at that time I was going to get a man that night. I was in the mind set to please. Rubbing my cock all the way there until I got to the hotel room having it set up for wet sex. This time as well I remembered to shave my legs, dick...Read On

Added: 02 Jan 2007 | Category: Crossdressing | Avg Score: 4.53 | Tags: cross dress  porno   | 3 Comments