Girlfriend Roommate Stories

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I Became a Girl in College

by TammyPanty on Apr 4, 2018
Transsexuals & Crossdressers

I was almost 19 years old when I started my freshman year at college. I got into a very fine institution in the Mid-West that was two thousand miles away from my home on the West Coast. Having grown up an only child of a single mother I was much more used to feminine things than I was anything masculine. I absolutely loved wearing pretty lingerie much more...

Connie Goes to College Ch. 06

by cmorehead on Sep 25, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * My freshman year in college became quite a year for me in terms of defining my f...

FreshMan

by Domwoolf on Sep 2, 2017
First Time

My Dear Readers, Disclaimer: What I write is fiction/fantasy/fairy tales for adults. None of my characters are real, no one was injured during the production of my stories and just like on T.V., they all get up when the scene is over, have a beer, remove the makeup and go home, ready to return in the next chapter, all the boo boos healed. Votes and commen...

Lulu's Lockdown Diary

by lululuvsblack on Jul 6, 2020
Transgender & Crossdressers

Day 1 So, with this virus we've all been told to stay home and not have any physical contact with people outside, not get together in groups at all, and not even step out of the house if not completely essential. We're locked down. I guess it wasn't a great time to move in with a couple of guys I barely know, but there you go. There's nothing I can do about...

Waking Up with Brooke Ch. 01

by TheGuyInBlack on Sep 13, 2017
Transsexuals & Crossdressers

Tim was very proud to be a student at Penn State, but tonight he was in a sour mood. As a student, he was a die-hard Nittany Lions football fan, which made this moment particularly frustrating. The team had just lost a heartbreaker to Ohio State in double overtime after an incredible 4th quarter comeback by PSU. Sure, Ohio State was clearly the better team,...

Gay for Candy

by BuckyDuckman on Jun 19, 2018
Novels and Novellas

It was the darkest secret Ashton had ever kept and knew he had to tell his girlfriend. Candice deserved to know he was a poser and a liar. The couples only camping trip felt like a good time to him. They would be away from the regular world, lost in the woods and surrounded by their best friends. Ashton and Candice followed behind Jared and his girlfriend....

Young Gina, Old Grace

by Hornyman69WithU on Sep 17, 2017
Mature

When I was in my late 20s, I had a 22-year-old girlfriend, Gina, who soon after we met, started rooming with a much older woman, Grace, in her late 50s, maybe even 60 or beyond. It was just a coincidence that she was the mother of an old acquaintance of mine who'd long ago moved out of state, and I'd met her many years before, when he and I went to prep scho...

My Weekend of Firsts

by WFEATHER on Sep 12, 2017
Group Sex

After a long and powerful lovemaking session, my girlfriend and I relaxed together in a hot bath, the strawberry-scented bubbles combining with the few flickering candles to further enhance the romantic atmosphere as Holly leaned back against my chest. I lovingly balanced her breasts in my hands, enjoying the feel of her hands caressing my thighs. "I got a...

Getting Down at Brown

by ReedRichards on Sep 11, 2017
Romance

I had just gotten my pants back up when Jeff and his girlfriend, MaryEllen, walked into the dorm room Jeff and I shared. Jeff went straight in to the bathroom, when MaryEllen smirked at me and said, "If you're going to jack off in this room, maybe you at least ought to do it in the bathroom." I was busted. I didn't realize it for a second, but a deep breath...

My Angel on a Winter's Night

by JulianDelacourt on Sep 2, 2017
Erotic Couplings

I returned home from watching my roommate's band at a club one Saturday night to discover I had locked myself out of my house. My roommate in the band had gone home with a groupie and wouldn't be back for some time. With our other roommate gone home for the holidays, my prospects of getting into the house tonight was slimming fast. It was winter, ice and sno...