Crossdressing Friend Stories

142,454 results
Orientation
Length
Source
Infinite Scroll

Life Almost Imitating Art

by JTeazer on Aug 19, 2017
Exhibitionist & Voyeur

Mutual friend and clothing optional beach enthusiast, Andrew was coming over the house to help Hubby Jeffrey with a project. We'd met him at the shore and formed a friendship, likely made more interesting by the fact most of the time spent with each other was done in the buff. Three way conversations included life, politics, sports, weather, and sex. Talk b...

New Year's Kisses

by Jennings21 on Sep 14, 2017
Erotic Couplings

This is my first story I have ever written. Everything I have written is based on true events. Happy reading! ***** Seriously, it's not even midnight and I can already hear champagne bottles popping open. My roommates are practically alcoholics at this point in the game. 9pm and our party hasn't even started, in fact- nobody has shown up yet as I'm finishi...

Dark Desires

by VeryNaughtyGirl3535 on Sep 17, 2017
BDSM

When I got that call from the receptionist I was expecting that he didn't want this relationship to happen but to my surprise he did want this relationship to happen. To the meeting I wore my black pencil skirt, my black silky blouse, my ballet flats, my hair was straighten , and I had curled it just a little bit. On the way to Newton Industries I realize th...

Cousin Becky Ch. 5

by jacksgirl on Sep 12, 2017
Erotic Couplings

By the time they graduate from college, most people know what they’re going to do, or at the very least where they’re going. After our graduation, I suddenly realized I had no idea. I can’t go home. Well, ok, I don’t have a home to go to. My parents were killed when I was a kid and I certainly can’t go back to my aunt and uncle’s farm. I was sitting on the b...

Girls' Night Out

by Dixie_treasure on Sep 14, 2017
Erotic Couplings

My best friend Sandy and I have worked together for 2 years. We have taken trips together, gone out drinking, had some good times. She has recently divorced, while I am happily married. Last weekend, we decided to we needed a girls' night out. We decided to have a male friend of mine drop us off at the club for a night of drinks and pool. We were dressed for...

Two's Company, Three's A Party...

by pompeybloke81 on Sep 15, 2017
Group Sex

NOTE: This is based on an actual event, therefore names have been changed to protect the innocent! (well, obviously not innocent, because otherwise…) This story was written in co-operation with "Lydia". Well, what started as a fairly average night ended up as one hell of a party! I had arranged to meet one of my mates in the pub, as we always did on a Sunda...

The Hard Sell

by rachelstorm on Sep 17, 2017
BDSM

The stinging, hot, coffee tasted slightly bitter as Staci sat at the table. She felt tired, reaching for her cigarettes and pulling one out of the pack. She lit it and took a long drag, the smoke making her throat tingle as it worked it's way into her lungs. She exhaled and took a sip of the coffee sitting in front of her. It had been a long night at work a...

My Wife Wants to Read My Stories

by Dylan800B on Sep 13, 2017
Loving Wives

Heather asked me the other night. It was one of those times when I wasn't sure if I should keep my mouth shut or tell the truth. I figured, after all, she married me knowing my past. What would be the harm of answering honestly? She phrased her question in as non-threatening a manner as possible. If I didn't know better, I might have thought she just wante...

Effective Lingerie

by RockHardau on Sep 17, 2017
Loving Wives

Sarah was floating through the air with her friends in a wonderful life; an annoying alarm clock buzz filtering through the background. The morning arrived two hours too early for Sarah as the alarm clock brought her back to earth from her dreams. She lifted one eye to the red face of the clock and confirmed that another 6am day had arrived. She gave her l...

Our Friend Amber Ch. 01

by gmouser67 on Sep 1, 2017
Group Sex

My girlfriend, Susan is in my opinion the best of the best. She stands 5’2” tall, with blonde hair and hazel eyes, 38DD tits, 30 inch waist, and 34 inch hips (I love ‘em like that). My name is David and I stand 5’6” tall with brown hair, blue eyes, 32 inch waist, and a better than average length cock. Well anyway, back to the reason that I’m writing this dow...