Crossdressing

cassandrababy

Adventure in St. Louis

Cassie's adventures on a night in St. Louis

A NIGHT IN ST. LOUIS Work can really suck. At this moment I am sitting on an airplane wrapping up a three day business trip. Thank goodness I know how to make work fun. If someone gives you lemons, I say make lemon meringue pie, because lemonade is not good enough. What I am getting at is you have to make the most fun in your life, because life is too short. If you have a passion, make...Read On

Added: 18 Jan 2011 | Category: Crossdressing | Avg Score: 4.88 | Tags: crossdressing  anal  oral  quickies   | 9 Comments

gstringguy697

An Interesting Night

I was outside dressed up in a school girl outfit...

Before I begin, I would like to inform the audience that the events in this story actually occurred, to the best of my memory. It was a cool, breezy, summer night and I felt the urge to dress up in a sexy outfit. I chose to wear a school girl skirt, top, stockings, bra, g-string, and stiletto heels. I felt sexier than ever, my whole body clean and shaven. At this point, I am 18 years old,...Read On

Added: 24 Jul 2008 | Category: Crossdressing | Avg Score: 3.96 | Tags: | 3 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: 4.78 | Tags: strapon  panties  femdom  feminization  sissy  anal   | 7 Comments

JesseS

Crossdresser's Spanking Scene

The CD to CD variation of an erotic 'spanking leads to sex' scene, already posted.

My roommate and I were both bi and part-time cross-dressers. We were also familiar with consensual B & D and had already worked out several code words, then went a step further and wrote scenes for each other, so that when we're in the mood, we could call up the scene rather than try to explain it or coach someone through it.   Sometimes we did a scene to please each other sometimes we...Read On

Added: 25 Jan 2010 | Category: Crossdressing | Avg Score: 4.62 | Tags: crossdresser  spanking  m-m  anal   | 1 Comment

cum_dump_boy

Cruising The Drive In

It was a Friday night and all of my friends were at home with family. I was really bored and I asked my dad if I could take the van and go to the movies. He said it was ok and told me to be home by midnight. The van was a 1977 Chevy van, it was brown in color and had the moon windows cut into the side. It had the typical "Captain' s chairs" up front and in the back had what you'd expect from...Read On

Added: 28 Nov 2009 | Category: Crossdressing | Avg Score: 4.77 | Tags: | 7 Comments

Diane91020

Friday Night Maid - 1

On Friday nights she goes out with friends, He becomes the Maid for the night

Friday Night Maid - By: Diane Leonard I am a Friday night maid. After a week of hard work, I relax by dressing up in a sexy maids outfit and serving, pleasing and pleasuring my wife. While she is out dancing with her friends, I am dressed up as a Friday uniform waiting for my wife to return home. She doesn't like my fetish, but this agreement, once a week seems to work for us. But ...Read On

Added: 18 Aug 2008 | Category: Crossdressing | Avg Score: 4.53 | Tags: maid  romance   | 3 Comments

jimymac

Date with my wife

It started with my love of sexy lingerie. I planned a date with my wife. She was to come home from work and go up stairs to clean up. Once all cleaned up she was to put on the outfit I laid out. She had lots of questions that I wasn't answering. She wasn't to come into the rest of the house until she was dressed. Well my day started by going to the store shopping for dinner and an outfit....Read On

Added: 24 Jun 2012 | Category: Crossdressing | Avg Score: 4.86 | Tags: wife  role playing  crossdressing   | 8 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

cassandrababy

Confessions of a Sex Crazy Cross Dresser Part 2

Chapters 3 and 4

Chapter 3: New York with Linda I didn’t really get a lot of time to think about what I had just done with Carlos. I fell asleep shortly after he left due to all the drinks I put away during the night. I actually fell asleep on my couch, still full dressed except for my jacket and shoes. When I woke up, I had a headache and was starving; I never even had a piece of the pizza Carlos brought....Read On

Added: 26 May 2010 | Category: Crossdressing | Avg Score: 4.83 | Tags: anal  crossdressing  sex  prostitution   | 4 Comments

cassandrababy

Extended Vacation

The first chapter of my second novel

Hi Everyone...this is the first chapter of my second book. I will publish more chapters if you like this one. Extended Vacation Chapter 1 Hello my name is Cassandra. You can call me Cassie (or Sandy, but recently, I like Cassie). I have been cross dressing for many years. However, the last year, since I turned 40, I have been dressing more than I ever have in my entire life. I made a...Read On

Added: 07 Apr 2011 | Category: Crossdressing | Avg Score: 4.92 | Tags: cross dressing  oral  quickie   | 6 Comments

jools

Capri

My first driving lesson

Friend of the family -Bi Curious story This is my very first story, I hope you enjoy reading it and I hope it inspires you to contribute My name is Jools I grew up in the west country from the late 60’s until the present day My tale based on a true story happen in 1970. At the time I would be at the tender age of 16. When your young the time can't pass...Read On

Added: 05 Jul 2009 | Category: Crossdressing | Avg Score: 4.75 | Tags: bi curious  mind games  tights fetish  cock sucking   | 2 Comments

LisaLeeCD

Lisa Lee Xdressing Adventures

I just love crossdressing sex!

    I have been crossdressing since I was about 14 and by the time I was 18 or so I was meeting with guys I met online for sex and I loved it!   I got married to a hot and sexy lady when I was 23 and I thought that might take care of my tranny urges but in reality it only made it worse. I now have to go long periods between playing dress up and it’s often all I can think of so when I...Read On

Added: 20 Apr 2009 | Category: Crossdressing | Avg Score: 4.71 | Tags: | 11 Comments

summer1979

Airing Out the Laundry

sex at the laundry mat

Rick was so excited to be moving to the big city. He was 22, from a small town, and got a good factory job in the city a few hours from his home town. Rick would be far enough away from his parents that Renae would be able to roam free. Rick found a little 2 bedroom apartment on the ground floor of a building in a gay community, though he did not tell his parents it was. Rick's parents...Read On

Added: 24 May 2009 | Category: Crossdressing | Avg Score: 4.5 | Tags: anal  crossdressing  oral  firsttime   | 1 Comment

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

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