Hookup Stories

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Camping Alone Has Huge Advantages

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

This is another true story, probably the last one (for now) worth writing about. I have been fucked while dressed 19 times to date. Not nearly as many times as I'd like (as I type this though, I have an ad posted on Craigslist again and hoping for another memorable story to relay to my readers), 9 of which were with a regular I had for a short time, and was...

Roxy's New Roommate

by Ben Rosewood on Nov 21, 2019
BDSM

Guess I shouldn't have been surprised it would come to this. Jack always insisted he was getting better, but sure enough, he was up to his old tricks: Stealing shit to fund his 'kicked' dope habit. Now I'm sitting on my front porch as Detective Pindick goes through my shit. He probably thinks I'm in on it. I'm sure to him that anyone with tattoos and a mohaw...

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My Loving Wife and the Masseur

by watchmywifey on Sep 12, 2017
Loving Wives

My wife and I have been married now for over 25 years. I call her my long-legged, blue-eyed, blonde-haired Nordic goddess. Before we got married we had flown from Southern California to San Francisco for Halloween. We visited my male cousin who had invited us to stay with him. I'll save the details of that visit for another story, but suffice it to say, we e...

Morgan's Lunch Break

by Ben Rosewood on Dec 5, 2018
MILF

The alarm assaults my ears so my hand returns the favor by smacking it. Time to get going. In the shower, I decide to have a quick play with myself and my vibrator. A little bit of me time before I have to get my son ready for school and go to work. Between spending time with my son Max and my job as a lawyer, I didn't have much time for dating, so I take wh...

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Gone Before Sunrise

by FelixFontaine on Sep 16, 2017
Transsexuals & Crossdressers

It was late, and Josh was bored with his late night graveyard shifts. He had taken this job a few months ago, thinking how easy it would be to work graveyards at a motel. It freed up his daytime, and the nights would be so slow that he could focus on some writing. Tonight was definitely slow, but he had writer's block and a semi-hard cock. He decided to brow...

Sissy Training

by kendra13 on Feb 13, 2018
Fetish

I am a blue collar manager type and live a pretty work a day life during the day, but at night, I have a rather interesting sideline. I am a sissy trainer. You see, many sissies are married and end up coming out to their wives. To most couples, this just creates a fun little fantasy for play during sex, but for some, it becomes more. For these couples, at so...

Craigslist CD Hookup

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

I have been crossdressing since I was a kid. I started out with a pair of my mother's pantyhose, as most other crossdressers start out the same way. Once you get bit by the bug, you're hooked. This is my first story, but I have so much to tell that this certainly won't be my last. All of what I tell you here will be 100% true. I will not dramatize or sensati...

Perfect Marriage

by Skippy47 on Jan 6, 2020
Loving Wives

AUTHOR'S NOTE: This is my contribution to the 750 word stories. Hope you enjoy. * I had the perfect wife. We loved each other with a passion sometimes that burned but always stayed well lit. All significant matters were discussed before decisions were made. Carolyn was an attractive woman who liked to look good more so I would be proud of her than to entic...

Hotel Hookup

by PandoraTolson on Sep 16, 2017
Romance

Amber walked past the lobby, ignoring the looks from the others, who smiled or nodded greeting. Today she was a woman on a mission. Amber found a toilet and ducked in. She lifted her skirt and pulled down her pantyhose and removed the little bit of lace that were panties. She ran a couple of fingers over the course hair and smiled to herself. She had to b...

Tish

by new2char on Sep 16, 2008
Cheating Spouses

I had just graduated from college and started my new job at a new consulting company, M2. It was a big company that hired hundreds of kids right out of college every year, and you tended to hang with your "class". I quickly clicked with a group of 10 - 12 men and women as we worked hard and socialized together after hours, so that we talked about e...

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