Girlfriend Trouble Stories

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Infinite Scroll

Hell Hath No Fury...Pt. 03

by DrewScott on Sep 14, 2020
Sci-Fi & Fantasy

Hello to all. This is Part 3 of my story and yes there will be a part 4, grrrr. It has no real relationship to the other items I have written. It's a continued commentary and idea formed around a common argument between a friend and I. While he is a Tech Guy, he has an absolute abhorrence to the idea of an AI companion. While I, being more in the Luddite and...

Monster Girl World Ch. 17

by Venus444 on Oct 8, 2019
NonHuman

Chapter 17-My Lovely Stalker Girlfriend Akira and Sayako had been dating for a month and a half now, and Akira was starting to get the hang of things. Despite Sayako being generally creepy and possessive, and having a mother who acted just like her but only scarier, and having three little sisters who acted more like actual centipedes than little monster gi...

Naked Hedo Sex Vacation Ch. 02

by TheNekkidUn on Mar 2, 2020
Exhibitionist & Voyeur

She's wiping the flood of cum from her face as we walk the pier back to our pool chairs. Naked, holding her hand, I'm just in awe of the moments prior. And feeling a little proud of the performance, my cock stays hard, pointing the way back to the pool. Lynn did the work, but I get the benefits I think as we round the corner and hit the decking. Hot under...

The Advert

by Professorredbottom on Jun 9, 2020
Illustrated

It happened almost two years ago, the kind of thing you don't forget. In fact, I can jack off just thinking about it. Yea, no kiddin, well, it happened like this.... I found an ad in the university, alternative, newspaper, stating that a Professor doing research, would pay men, ages eighteen to forty for semen samples, the more samples you can provide in a...

Knock Before Coming In

by Liver96 on Dec 2, 2019
Transgender & Crossdressers

Rough Lesson: Knock before coming in Short story about futa on male, if you are not used to it, feel free to skip it or read at your own risk. In a splendid house in the suburbs of Richmond, Virginia; an 18 year old boy lived with his parents, his name was Matt. Matt was a very disrespectful and unsociable boy, he did not talk to anyone and did not leave h...

My Two Girlfriends: How We Met

by Pissfan1234 on Dec 2, 2019
Group Sex

All straight guys dream of having a girlfriend at some point in their life. I've had three in total since I started dating. The stories of my second and third, however, are only one story. During my sophomore year in college, I had a falling out with my dorm mates over them dumping all the rent payments and laundry on me. I just snapped from all the stress a...

Meeting a Pro Football Player

by KissedMany on Oct 6, 2020
Group Sex

Hi, my name is Teena. Let me share the amazing adventure I had last weekend. First, a bit about myself. I'm nineteen and graduated from high school last year. Right now, I work at a family restaurant as a server but I have bigger ambitions. Men say I'm pretty and a fellow from a modeling agency even invited me in for a photo shoot. Nothing came of it, but I...

The UPS Guy

by dysfunctionaldreams on Sep 15, 2017
Transsexuals & Crossdressers

I was sitting alone in my apartment when there was a knock on my door. I got up quickly and raced over to the door. I unlocked the deadbolt lock and swung the door open. Standing there, to my happiness, was a UPS driver. I had been awaiting a package for some time. I had ordered my first breast forms online and was dying to try them out. I had also included...

Me, Tommy and His Girl Ch. 03

by CuckFantasy69 on Apr 23, 2019
Exhibitionist & Voyeur

I was woken up by Gianna sucking my morning glory. I rubbed my eyes still half asleep as I realised this horny slut did not even wait for her boyfriend to wake up beside us. But the sucking and slurping sounds woke him up eventually. Me: Good morning Tommy. Looks like your girl here has no manners, or maybe she's so hungry she wanted my sausage breakfast....

Karyn's Summer Vacation Ch. 05

by Missthefriz on Dec 18, 2018
Loving Wives

After a few days, a crew came to the house to do some work. When Karyn saw them, she was not thinking about any adventures that day. There were 6 of them, the 2 bosses, in their 40s, and 4 laborers, all in their mid 20s. Through the day, Karyn would take out cold drinks as it was hot. She learned the 4 laborers were all doing graduate work towards their engi...