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CAPITALLETTERJ

Crossdressing

9
vote
sarahsully

Yes Captain

The crew gets a little closer than normal

It had been a while since Sarah had a lover. She was aching to slip into something sexy and get a man going. She had been to a few clubs but found nobody that could fix her needs. That was until she arrived at work on Monday. Sarah was a copilot for a major airline. She entered the cockpit and met the Captain John. He was a good looking man. Tall, blonde hair, and a smile that would melt...Read On

Added: 29 Oct 2012 | Category: Crossdressing | Avg Score: 3.89 | Tags: flight attendant  captain  stewardess  crossdressing  sarah   | 2 Comments

40
vote
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

94
vote
DeedraCd

Halloween Trick or Treat Surprise

Dan and Susie go to a Halloween costume party Susie has him dress as a women and changes him forever

Chapter 1 –Susan Charity Event To my surprise Susie my wife of 15 years comes home from one of her many business trips. She is all excited about a Halloween costume party fund raiser, for non profit that supports women studies. The invitation states, the best couple for this evening will receive a free weekend in Bermuda. She wants’ us to go as couple switching genders.  Let me...Read On

Added: 24 Oct 2012 | Category: Crossdressing | Avg Score: 4.97 | Tags: first time  panties  crossdressing  t-girl  anal  transformation     | 26 Comments

18
vote
biguy2play

My Lesbian Lover

My first adventure out as a woman ended in the arms of a woman!

My wife was trying to come to grips with the realization that I cross dressed, with marginal success. Part of her plan was for me to meet in the Twin Cities with other CDs so I could have a ‘safe’ place to dress up, away from our small town. To be safe, I was to drive up, change clothes there, meet with my friends and then change again for the drive home. A good plan … a safe plan … but not...Read On

Added: 22 Oct 2012 | Category: Crossdressing | Avg Score: 4.67 | Tags: oral  crossdressing  fucking   | 4 Comments

28
vote
CourtneyFux

The Pool Man

Sunbathing near the swimming pool, I turn on the handsome new pool man.

It was June and time for sunbathing by the pool in my backyard. To my pleasant surprise, I saw that the pool man the company sent this year was young and handsome with a muscular body and porn star mustache. I was instantly attracted to him the first time he came and we hit it off quickly. I was wearing a pair of cut-off shorts with a sexy black thong panty underneath. And I felt very sexy...Read On

Added: 21 Oct 2012 | Category: Crossdressing | Avg Score: 4.65 | Tags: crossdressing  exhibitionism  oral  anal   | 5 Comments

6
vote
CourtneyFux

Girlyboy Gone Wild - Part Seven

Fifi, the sexy French maid, gets to do 69 with her handsome boss.

After getting Rich big and hard with my sexy outfit, I was now ready to put on a show for him Whenever men see me in my panties, they want me like a girl. It follows that whoever wears sexy little panties also likes big hard cocks to suck on and play with. My sexy French maid outfit was especially good at making me feel like a slut for a man. Since so many men had fantasized about being with...Read On

Added: 20 Oct 2012 | Category: Crossdressing | Avg Score: 4.33 | Tags: crossdressing  oral sex  voyeur   | 3 Comments

9
vote
CourtneyFux

Beach Day

Wearing my sexy panties to the beach gets the men turned on for me.

Wearing my sexy panties to the gay beach always gets the men turned on for me. Being the only girlyboy there, I get hit on by lots of big studs. The attention they give me is flattering and leads to lots of sexual pleasure. Being topless, I get to show off my nice titties and the sexy panties I'm wearing let the men know I want some dick like a woman gets. It was a beautiful day for the...Read On

Added: 19 Oct 2012 | Category: Crossdressing | Avg Score: 4.56 | Tags: crossdressing  oral  lifeguard  exhibitionism  voyeurism  anal  foot fetish   | 2 Comments

4
vote
kalira

Derek and Amy: Derek's Turn

Derek takes control

As I walked into the hotel room hours in advance, my cock was rock hard with anticipation. The last time me, my lover Amy, and her husband Matt were all together, it was my dear love Amy's turn to be in charge. Amy had Matt and I dress like two Fifties sluts. The kind of girls uptight parents used to believe would cause the downfall of society. It was both Matt and I's first times with...Read On

Added: 18 Oct 2012 | Category: Crossdressing | Avg Score: 4.75 | Tags: crossdressing  bdsm  anal  threesome   | 1 Comment

4
vote
kalira

Derek and Amy: Matt makes three

Amy's husband Matt joins the fun

My lover and my husband are in separate rooms changing into the clothing I've laid out for them. When they're finished they'll come into the library where I'm sitting waiting for them. This will be the first time they've touched each other and I'm not going to miss a minute of it. I'm sitting in a big padded chair diagonal to the door. My husband, Matt, comes in first. He looks...Read On

Added: 17 Oct 2012 | Category: Crossdressing | Avg Score: 5 | Tags: crossdressing  bdsm  anal  threesome   | 4 Comments

5
vote
kalira

Derek and Amy

Derek and Amy enjoy some time alone.

We're holed up in a nice little hotel room in the middle of nowhere. No one around here knows us and no one will bother us. Tonight's all about us. Once we get settled in I send him off to take a shower. Now that I'm sure he's busy it's time to get to work. Digging out my bag I lay out the outfit I've had prepared for a long time. The panties are black silk, as soft as butter. There's a...Read On

Added: 16 Oct 2012 | Category: Crossdressing | Avg Score: 4.8 | Tags: crossdressing  bdsm   | 3 Comments

19
vote
irishfella

My day as a cheerleader

send to boarding school leads to abit of fun

Hi I'm 16 and this is my story about what happened in boardingschool. My mom and dad just got divorced and my mom send me to boarding school for a school year or at least they sort out my custody. I was packing my case with my mom as I was just about to leave my mom went to start the car but I had to pack one last thing my sexy G-String. I zipped up my case and headed to the car and just...Read On

Added: 15 Oct 2012 | Category: Crossdressing | Avg Score: 3.68 | Tags: crossdressing  anal  oralsex  cheerleader  boarding school   | 1 Comment

2
vote
Karrenfuchmee

Karren Gets Sucked and Fucked Part 2

It gets hotter for Karren, Nancy and Kevin

Karren followed Kevin to his home in her own car so if she had to leave she could do so at her leisure. Karren wondered what Kevin's wife looked like, would she like the idea of a man dressed like a woman making love to her? Would she like sharing Kevin's cock with another man dressed as a woman? She hoped everything would turn out for the best.  Her thoughts were arousing her cock; she...Read On

Added: 13 Oct 2012 | Category: Crossdressing | Avg Score: 5 | Tags: wife  crossdresser  sex  cum   | 2 Comments

2
vote
Karrenfuchmee

Karren Gets Fucked and Sucked

Sex is abundent in this story

Adventure in Nylon 3 Part 1 Karren gets Fucked and Sucked He was all dressed up in his finest outfit. Starting with the prettiest white lace panties he owned. A white lace teddy with attached garters, a built in under wire bra that was filled with breast shaped silicone pads to look and feel like the real thing. He covered these with a silky smooth full white nylon slip. His shaved legs...Read On

Added: 09 Oct 2012 | Category: Crossdressing | Avg Score: 5 | Tags: dressed  first time out  threesome   | 3 Comments

18
vote
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

33
vote
TaraNicole

Six Months

A girl's dreams cum true

After all those years of longing to be free, stuck in relationships with women that frowned upon my cross dressing, I was still very much relishing my freedom. I was dressing every moment I could, the minute I got home from work every single day; a mini dress, heels and stockings were what I craved so desperately. I had been living alone now for a couple of years and would have thought he...Read On

Added: 03 Oct 2012 | Category: Crossdressing | Avg Score: 4.87 | Tags: transvestite  crossdresser  stockings  anal  oral   | 9 Comments

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