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Crossdressing

5

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

4

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

6

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

18

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

4

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

4

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

23

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

34

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

57

Do you want to wear my skirt?

Katie caught me looking at her skirt and made me wear it.

As I sat in the meeting I couldn't take my eyes off her. She was young and so cute and she was wearing a short pleated wool skirt. The skirt was a pink and light blue plaid color. She would cross her legs and pull the skirt down being sure not to show too much. When we went on a break many of us went outside. It was a nice comfortable fall day. I watched as she came out and stood by herself....Read On

3

Girlyboy Gone Wild - Part Six

After being a sexy school girl, I become Fifi, a sexy French maid.

With both of my hands wrapped around Dan's big 11 inch cock, I felt just like a little girl in his classroom. I jerked him off with both hands while I sucked on the head of his cock, getting it ready for him to put in my tight little girly ass. I licked around the big head of his cock, smelling my sticky-wet, cum-soaked white cotton panties he was wearing. Oh, it was all so kinky and fun...Read On

4

Girlyboy Gone Wild - Part Five

After being a sexy school girl, I become a sexy Frenchmaid.

Having my clitty dick sucked by Dan really did make me feel pretty and sexy. He was really good and was able to swallow all seven inches. While he sucked me, I played with my titties while he looked up at me. I was looking down at his big 11 inch cock sticking out of my white cotton panties he was wearing. It was all so kinky, it thrillled me to be having so much fun at my all-weekend...Read On

4

Girlyboy Gone Wild - Part Four

At my panty party, I get to suck four big cocks in one night.

Being a slutty sorority girl having sex with my professor was really fun. I was sitting in his lap with my back to him with his big 11 inch cock between my freshly-shaved legs and rubbing it against my hard clitty dick. My little white cotton panties were soaking wet in front with pre-cum. My teacher was playing with my titties while I stroked his big one. "I'm going to take your bra off,...Read On

7

Girlyboy Gone Wild - Part Three

Playing dress up for men at my panty party is lots of fun.

With my little sexy blue plaid school girl skirt pulled up, I leaned over the desk for teacher Dan to spank me. Dan reached down and pulled down the back of my little white cotton panties revealing my very sexy ass. I saw how big his eyes got when he saw two of the sweetest cheeks he ever saw. He looked up at me. "You have a nice butt on you, Courtney." I smiled. "I hope I get to sit on...Read On

6

Girlyboy Gone Wild - Part Two

The panty party weekend brings new boyfriends into Courtney's life.

It was very flattering when Bill told me I have a hotter body than his ex-wife. Since it was his first time with a girlyboy, I knew he was being honest. A more experienced gentleman might have said it just to be nice. But Bill really meant it. In fact, he said his cock was already hard for me just from seeing my nice ass poking out of my turquoise thong. Bill was my 7:30 date, then I had Dan...Read On

13

Girlyboy Gone Wild - Part One

An all-weekend party in my panties leads to lots of sexy pleasure for the boys.

Wearing sexy lingerie for a man is my favorite way to feel like a girl. I've been doing it since I was 16 and have never been shy about it. Every few months, I get the urge to do it. So, this month I did it again. To find men to turn on with my sexy lingerie, I placed an ad on the local dating line: "Hi. I'm a hot girlyboy who likes older men. I'm having a party in my panties this weekend and...Read On