Shy Girlfriend Stories

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Executive Relives Her College Days Pt. 02

by KissedMany on Feb 19, 2018
First Time

Last time I wrote about me erotic experiences, I mentioned my upcoming trip to Boston and its great university, Harvard. Well, I'm here in my Airbnb apartment just vibrating with excitement about the erotic adventures I'll be having later. Tonight, I'm going to a bar called the 'Pig and Blue Bull' close to the campus. Their website picture showed a young col...

I Wonder

by flutterbyspirit on Aug 18, 2017
First Time

Edited by Angel Love We meet, of course at Fanny's, local night club. My friends notice you watching me first as we dance and laugh. They dare me to go up to you, which of course I can't do, after all you're older than me and I'm way too shy to be so upfront (well back then I was). So I decide to go up to the bar for another drink. Hmmm, funny how I just...

Family Business & Sexual Adventures

by NerdySex on Mar 12, 2019
Erotic Couplings

"Baby, we getting together Saturday?" Jim asked his girlfriend Jan. "Sure. You got something in mind?" "Well, my brother has his eighteenth birthday. You know, he's kind of shy, not like me." "That's for sure. And ...?" "You like him don't you?" "Yeah, he's even better looking than you," she said with a smirk. "Of course, you're both studs. But he is ra...

Shy Wife Exposed To An Admirer

by ttlvr on Sep 26, 2017
Exhibitionist & Voyeur

Those of you that know my wife know that she is an interesting combination of beautiful and painfully shy. She is petite with a tight body, about 5'4" 110lbs. My wife is well known around town, active in local theater and our church. This fall, her volunteering and church led her to one of her most humiliating exposures. Jessica often volunteers to help wit...

With Best Friends Like This....

by bac512 on Sep 16, 2017
First Time

When I was 13, I was really shy. Bullied, pushed around, insulted. So I just assumed no one liked me (I did have a few friends, but, mostly I just stayed home and didn't talk to anyone, cause it was just safest that way) I did go out with my brother and his friends, I knew them pretty good from them coming over all the time. One day one of them brought his n...

Snapper Times Two

by twatstretcher on Sep 14, 2017
Erotic Couplings

This is a true story of something amazing and confusing that happened to me a long time ago between, myself, my girlfriend and her "church mouse" girlfriend/roommate. The names have been changed to protect the innocent. All of us were over 18 at the time. ***** I met my girlfriend Sharon when I was racing off road in District 37 in the southern California...

Nina Tells Our Friends I'm Her Cuck

by writemarksmith on Nov 26, 2019
Exhibitionist & Voyeur

"I think maybe...we don't need to keep it secret this weekend." Nina was feeling me out on the idea as we drove to her friend's cabin for the weekend. Her suggestion made me nervous but also excited. "I mean Monica obviously already knows, and you know I've fucked both Ben and Alex while we've been together." My girlfriend was proposing that we did not ha...

Is He the One?

by HSMan on Dec 11, 2018
Fetish

A very short account of a date from my kinky girlfriend. "What's the appeal?" My girlfriend asked. "Apart from the obvious, he's a very kinky and such a naughty boy." "Really, do tell me?" She replied. I'd had a few drinks, what the hell! "Ok let me tell you about my one our early dates... He met me at the station, he insisted on taking my bag. We wen...

Knowledge is Power Ch. 3

by Ridinghoodswolf on Sep 16, 2017
Anal

I looked through Andy’s program and chose my first…well, victim. She was about thirty, kind of shy and a little mousy, judging by her picture. She worked as a secretary in a government office. I had access to her emails from home, as well as a list of every link she visited and when. I used this information to study her habits. As she was my first, I ended...

Wild Sky

by CarmeloCremoso on Oct 15, 2017
BDSM

I wasn't looking for anything when I sacheted my way into Vinnys that night. It had been a long day on the road, and I had just finished playing a sold-out show at the PPG Paints arena. The exhaustion I felt was overwhelming. Needless to say, a bucket of Coke and Rum was calling my name. Sleep could wait. Taking a deep, steadying breath, I straightened my s...