Shy Girlfriend Stories

94,140 results
Orientation
Length
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Infinite Scroll

Tom, Helen and Kate Ch. 01

by sir_clackers on Sep 1, 2017
Group Sex

First of all let me set the scene a little. My girlfriend Helen is 23 years old and stunning. Slim but with all the right curves. An F cup chest and long long legs make me feel like the luckiest man alive. Her long blonde hair cascades over her shapely neck and shoulders making her look even sexier. Tonight she is having a girly night in with her best frie...

Marlyn Sheds Her Inhibitions

by asianudinpublic on Mar 26, 2019
Interracial Love

I wrote previously about my Filipina girlfriend named Marlyn. She's 5'2" tall, with very dark hair and nice big cheeks that swell when she smiled. She has amazing curvy legs, a very nice round ass and small and very sensitive breasts. She's thin --probably just a tad under 100lbs but still has nice curves. When I first met her, she was very conservative Ca...

The Fantasy Shelf

by HushHushCrush on Sep 13, 2017
Erotic Couplings

"Oh, what a cool little bookstore," Hannah said, "I didn't even know this place was here." The way she looked at the titles on the sci-fi/fantasy shelf told me everything I needed to know about her: Kid in a candy store. And a geek, too. She just had that look, like the thing right in front of her eyes was so exciting she wanted to take a bite out of it. "...

The Poker Party

by cockster21 on Sep 13, 2017
Fetish

Me and Kristen like to invite friends just go hang out on Friday nights. We usually rent some movies, drink beer or have a poker game. That night, Kristen had invited 5 friends over for our poker game: Dave, Catherine, Alex and Vanessa. Alex is a high-school friend of mine, a 6ft. tall man with short dark brown hair. Vanessa is Alex's girlfriend. She is...

Work Love Triangle Pt. 01

by egoBorder on Oct 15, 2018
Erotic Couplings

I've never been a player, really. Once I'm with a girl I don't go behind her back. Not out of any moral rectitude on my part, or because I don't find other women attractive. In fact the opposite is true: I find all sorts of women attractive, and I'm not shy about checking out women even in front of a date or girlfriend. But I guess in the end I'm satisfied w...

Neighbourhood Terror to Sissy Pt. 14

by Fibaro on Dec 2, 2019
Transgender & Crossdressers

Chapter 16 The two women enjoyed looking at Mark as he had to swallow all the white goo he had just squirted. Just as if the way he had achieved his orgasm wasn't bad enough yet? This only added insult to injury. It was Linda who suddenly broke the silence. "It is good you have come here to learn how to handle a sissy and it is my pleasure guiding you int...

Joe Surrenders

by phantome71 on Sep 16, 2017
Transsexuals & Crossdressers

My new partner is not really a girl's idea of a "ladies man." Nevertheless I have known Joe for a long time and when he asked me out I jumped at the chance. I had no illusions about Joe but one asset he does have is a decent bank account! His parents had died and left him with a nice house. He does have a regular job but I also knew that he was comfortably o...

The Camping Trip

by zildjian on Sep 13, 2017
Group Sex

He glanced across the stream he had just splashed through to see if Emma was having any trouble. Anger wrinkled his brow as he spotted the woman picking her way across. Some of her long red hair had come loose from her ponytail, and there was a smudge of earth across one perfectly sculpted cheek. Even with the distance separating them, Emma knew he was in a...

Prison Life Pt. 02: Meet The Gang

by Nude_Writer on May 29, 2018
Exhibitionist & Voyeur

The characters in this story are over the age of 18. This is my second ever story, and my first ever story that I hope to turn into a multi-part series. If you like it, let me know and I'll start uploading the rest. If you don't like it, let me know why and I'll try and re-work it so it's more acceptable. ... Zoe's cell, or rather, Zoe and Charlotte's cel...

Wimp Loses to Young Black Boss

by michaelwimphusband on Sep 19, 2017
Interracial Love

A True Story. At the age of 49, Myron felt that he had reached a certain degree of success in both his professional and personal life. He had worked diligently throughout his academic and business careers to be in the position he now was. He had put the failures of his past love life far behind him, and he was now going on his 14th year with this corporat...