Crossdressing

thony777

I become my wife's girlfriend. Part II.

This day at work was unusually tedious and seemed like it was never going to end. At the beginning I occasionally dropped my boss's cup and the coffee poured on floor, but luckily the cup survived. After this some guy stepped on my toe and caused me much pain, I bent to touch it and suddenly had a feeling like my butthole was cut by the string of thong. Later my boss was very angry all the day,...Read On

Added: 25 Mar 2011 | Category: Crossdressing | Avg Score: 4.73 | Tags: crossdressing  wife  girlfriend   | 6 Comments

pantylovincumguzzler

having some in panties with friend

guzzling cum for the first time

First time ever sucking cock in panties:              This is the first encounter Taylor had with another man. Taylor had just started wearing his mothers panties after taking interest in a mesh thong he found in the laundry. After a few weeks of wearing them he wanted to share his passion with someone else but never thought of who it could be with. All he knew is that it had to happen...Read On

Added: 26 Jun 2009 | Category: Crossdressing | Avg Score: 3.97 | Tags: gay male  oral  anal  first time   | 7 Comments

Teigan_andi

First time

I was 17 when I had my first experience with another man. My sister was in her sophomore year at college and I in my senior year at high school. She was going to spring break in Florida and since me and her had always had a great relationship she invited me along with her and her friends. My sister was cute, blond hair and blue eyes. Very tan and athletic. She had that all American preppy...Read On

Added: 22 Mar 2011 | Category: Crossdressing | Avg Score: 4.62 | Tags: first time  crossdressing  thong  cum  anal   | 16 Comments

LingerieBoy

What Do You Do When....

The weekend arrives and mom and dad are going out and I assume they are going to one of their swinger parties and won't be home until early the next morning. So I do my normal thing when they are gone and play dress up and go out and hunt for dick. But this time I knew they would be gone and had already planned an evening of fun with a couple of guys I had met at the adult bookstore my...Read On

Added: 14 Aug 2008 | Category: Crossdressing | Avg Score: 4.82 | Tags: crossdressing  oral  anal     | 7 Comments

Daddysgurl

Dad Catches Me With His Friend

From an early age like most I started to get a desire to wear womens clothing. I would always take my mom's thing's and put them on and masturbate in them. The feeling was nothing like I have ever felt before. Around the age of 16 I had gotten a job and started buying my own things,lingerie and such with the money I earned from the job. Prior to that,around the age of 13 my mom had left...Read On

Added: 18 Jul 2008 | Category: Crossdressing | Avg Score: 4.83 | Tags: crossdressing  sex   | 9 Comments

PlayfulAshley

Ashley’s First Time With a Guy

Ashley’s First Time With a Guy DISCLAIMER: Story is merely fantasy and completely fictional. So please do not believe this happened to me or ask me questions about it, thinking it is true. I am writing simply because it is a fantasy and it’s just more fun that way;) So it all started on Valentine’s Day of that year. My wife and I had gone to dinner and got a hotel room for a romantic...Read On

Added: 03 May 2011 | Category: Crossdressing | Avg Score: 4.89 | Tags: crossdressing  first time  anal  oral   | 21 Comments

starbelliedboy

Fulfilling A Girl's Male Fantasy Part 1

Jennifer has a surprise request for Jack.

"Get undressed," the pretty brunette told me, and I obeyed. She was called Jennifer, we'd met the night before at the rock nightclub, and I'd thought that she looked gorgeous in her goth make up so she invited me back to her place. It turned out that she was eighteen and still living at home, so we locked her door and did our best to keep quiet as we fucked the night away. Now it was noon,...Read On

Added: 18 Aug 2009 | Category: Crossdressing | Avg Score: 4.69 | Tags: oral  crossdressing  sex  strap-on  gender bending  anal   | 1 Comment

Markdwyer1984

Minding the House

Short true story about the fun I got up to while minding my neighbour's house

My neighbours Tom and Paula were going away on vacation and they asked me to keep an eye on the house for them. I gladly accepted as I wanted to see what their house was like on the inside but my curiosity really lay in exploring Paula's underwear collection. Paula was a 34 year old pretty mom of two kids, 5ft 7 with blue eyes and shoulder length brown hair. She possessed a slim but...Read On

Added: 13 Oct 2010 | Category: Crossdressing | Avg Score: 4.69 | Tags: crossdressing  stockings  lingerie  masturbation   | 7 Comments

sexmachine

Crossdress boy's ultimate romp

Humiliated cross dresser discovers a new fetish

He was in his late 20s.. I'm in my late teens. the thought of meeting him really didn’t come across my mind. however I was won over by his passion and sincerity and he doesn’t even mind if I didn’t shave my legs! wow! we arranged to meet at the car park near my place, he asked me to wait for him and he'll reach in about 45mins. I went straight to my aunts drawer, looking for my favourite...Read On

Added: 02 Jan 2007 | Category: Crossdressing | Avg Score: 4.13 | Tags: pee  crossdress  golden shower   | 3 Comments

Jess_cd

Caught by a neighbour

I've secretly been crossdressing from a young age. In my late teens, around 17, I became more adventurous. maybe because I was enjoying it more. At that age I was very slender, had long dark hair as well has having a naturally smooth and hairless body. My brother and sister were both at uni and my parents would work a lot of the time meaning I was left home alone quite a lot. I would "borrow"...Read On

Added: 07 Oct 2011 | Category: Crossdressing | Avg Score: 4.62 | Tags: dressing  neighbour   | 14 Comments

annabell

A helping hand

Found out by a mature woman

It all started a few years ago. I was dating a girl who was bisexual. So much so that she wanted me dressed as a woman for sex. To begin with I was not sure, but eventually I came round to the idea. It was mainly just some lipstick and perfume. After a few months we split up, but I continued to dress up. One day I decided to venture out as a woman. I lay in bed thinking what I should wear....Read On

Added: 07 Apr 2008 | Category: Crossdressing | Avg Score: 4.11 | Tags: crossdressing  mature   | 8 Comments

Cdashlynninsc

Two girlfriends have a couple over for a fun night

Wife sets up night for us to be girlfriends, then invites another couple over for fun

My wife Dawn had surprised me by saying we were spending the night in as two girlfriends, laying out my clothes so we matched. Then after having amazing sex, Dawn surprised me by telling me that she had invited her friend, Maria, and Maria’s husband, Mark, over for some fun with the two of us and to fulfill the fantasies of all of us. So I was standing there with my red plaid skirt,...Read On

Added: 05 Sep 2010 | Category: Crossdressing | Avg Score: 4.84 | Tags: crossdressing  oral  girlfriends  wife   | 7 Comments

watcherfun

All Dressed Up Part 1

When I woke up naked, I had to find some clothes.I never thought I'd have to wear girls ones though!

Having been out with some mates, I woke up in the middle of the street the next morning. What was a greater worry was the fact that while I had been drunk the previous night, my mates had removed all my clothes and left me naked! With no money and no clothes, a trip home on the bus wasn't looking promising, so I decided I would try and at least find some clothes. Then maybe try and convince...Read On

Added: 06 Jul 2010 | Category: Crossdressing | Avg Score: 4.74 | Tags: crossdress  crossdresing  naked  teen  teenager  young  forced   | 11 Comments

webbyhose

Friend's Treat

A divorced man gets a treat

I had recently split with my wife and was feeling very down. I was invited to spend a few days with my old friend Dave and his wife Tracey. The first night I was there Tracey turned to Dave and said that we needed a boys' night out and why not go to his club. Dave agreed it was a good idea and within minutes Tracey was dropping us outside what appeared too be a Georgian townhouse. I...Read On

Added: 09 Nov 2010 | Category: Crossdressing | Avg Score: 4.92 | Tags: shemale  gay   | 9 Comments

sissyslut_trish

Caught dressed like a sissy slut

My girlfriend was away for the weekend so I had the place to myself. I was feeling incredibly horny so I went through her knicker drawer and decided to dress up (which I've enjoyed many times before). I put on a really tight, pink thong, black fishnet stockings and suspenders, and her black mini skirt. I looked at myself in our full-length mirrored wardrobes. God, I looked so sexy and...Read On

Added: 10 Aug 2012 | Category: Crossdressing | Avg Score: 4.62 | Tags: crossdressing anal humiliation   | 5 Comments