Shy Girlfriend Stories

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Infinite Scroll

This Bikini is so Tiny at the Party

by KissedMany on Sep 21, 2020
Group Sex

This is the second installment of "This Bikini is so Tiny I Feel Nude" In the first one, Meagan, a freshman in college in Florida, went to the beach with her BFF and met Chad a handsome sophomore. Shy Meagan ended up the evening give Chad a blowjob in a beach cabana. It's a sexy story that you will enjoy. This instalment takes their budding romance a lot fur...

My First Time as Sara... Pt. 03

by Sexy_SaraCD on Sep 18, 2017
Transsexuals & Crossdressers

I've been with Steve for a couple of months and to say I've been happier than at any time in my life would be a gross understatement. Being with Steve has been an awakening. I'm no longer afraid of life. I was shy and timid as John. I didn't make decisions. I didn't take the lead in anything and was easily bullied. My ex fiancé was the worse bully. As Sara...

No More Shyness

by Barbarina on Sep 16, 2017
Interracial Love

She has always been a shy woman. At the age of 33, she was still a virgin, for various reasons. Some men told her that she had a beautiful face, a few men even fell in love with her, but she continued to be shy and never thought of herself as sexy. In her country, many men seemed not to notice her beauty. And with her full buttocks and plump thighs, she once...

Omnipotence

by PervertedKatharina on Mar 18, 2020
Fantasy

Character description: Larry (18): Our main character. He still goes to school and has always been kind of an unpopular kid. He recently got together with a girl though. He's somewhat of a nerd and will soon be granted with godlike powers. Madison (49): Larry's mother. She's a very caring woman who raised 5 children after her husband died a few years after L...

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Matrimonial Tryst

by diosdeguerra on Sep 14, 2017
Erotic Couplings

I love my girlfriend. I really do. But I'm still a guy. Which means that I can't help but harbor certain fantasies about my girlfriend and her twin sister. Or, for that matter, her older sister. But none of those fantasies are the subject of this tale. This little story is about something that actually happened. I was sitting at the bar during the reception...

Asia's Persuasion Pt. 01

by asiapersuasion on Sep 25, 2017
Interracial Love

You can call me Asia. I am a twenty-two year old college girl, and I have been up to quite a few adventures in the past couple of years. Some of which has gotten me into a lot of trouble and some have fulfilled my deepest and secret desires. The stories that I am about to tell you are true stories from my past and I have changed my name including the name of...

More Fun with Willow Pt. 01

by MisterUnusual on Sep 18, 2017
Exhibitionist & Voyeur

Author's note: Willow was originally created for a single story to enter in the Summer Loving story competition. That story, Shy Slutty Willow, still stands on its own, however, once I completed it I realized I had so many further ideas for her that I should write about her further adventures as a multi-part story arc. I toyed with telling the story from Wil...

Bimbette's Valentine Fashion Show

by Jackson Blacke on Sep 14, 2017
Group Sex

Bimbette decided it would be a good time to neaten the widow display at Samantha's Sexy Slut Salon. It was an hour before closing on Friday, February 13th, a doubly bad day for her. Friday the thirteenth is intimidating for most people, of course. But it was also the day before Valentine's Day, which was especially depressing for Bimbette. The reason was t...

No Suck, No Fuck

by Bluespark on Sep 12, 2017
Group Sex

It was back when I was in college. I majored in English but my roommate was a jock. We didn't get along well at first. I was really shy back then and he was loud and boisterous and really got on my nerves. Being a jock he was used to being around other men and would walk around our room completely naked when he was getting ready to go out or just hang out in...

Back-alley Sissy Boy

by Travel_by_day on Sep 12, 2017
Fetish

I saw you while I was walking through the grocery store. You were bent over, picking up something off the bottom shelf. At first, I thought you were a girl, because of your nicely shaped ass and the fact that your low rider jeans were riding down, exposing a lacy white thong. I was so turned on, my cock started to get rigid right away. If I had been wearin...