Shy Guy Stories

162,824 results
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Infinite Scroll

The Gang Bang Party

by AK_gals on May 15, 2019
Group Sex

This is a very true story. A few weeks ago my shy hotwife and I attended a fun LS party. It was originally planned as a Gang Bang of a 30-something newbie named Missy. Usually these GB parties are done with two experienced women. Despite being shy, my hotwife has lots of GB experience but wasn't yet on this party list. It had been a few months since she att...

Ellie

by BeMyPet on Sep 2, 2017
Erotic Couplings

Ellie and I became lovers when we were freshmen in college. She was this small, slight little goth girl, with waist-length straight black hair and flowing black dresses. Her smile was a Mona Lisa thing, fuzzy at the edges and hinting as something naughty. She rarely spoke but often stared, and it was this staring that originally caught my attention. We had a...

Party Night

by Latinababe on Sep 16, 2017
Anal

When I was 18 I thought I was pretty experienced with guys, but everything changed in one evening. Sure I'd gotten laid before in the middle of the woods a few months earlier. Though it hurt at first, he made me come; that's what I told him, at least, and there was a second guy who really turned me on, or so I thought. And others. So, I often had a lot of at...

Straight Laced Girl

by handstogether8 on Sep 13, 2017
Loving Wives

We entered our house and were greeted by the lovely sound of silence. The kids were gone. Our friends had taken them to the movies so that Jewel and I could be alone on our anniversary. We had used to opportunity to go out to dinner. It had been fun. Jewel had looked wonderful. She had worn the gold anklet I had given her that morning. It was one of those th...

Another Visit to Mon Chalet

by Atrampboy on Sep 1, 2017
Group Sex

The following is a true story, well, as true as memory allows...My Girlfriend Tes and I enjoy visiting a motel that has been converted for enjoyment of swingers, it's a small, 25 ish rooms, motel with all the rooms made over with mirrors, faux fireplaces, provisions for swings and most rooms have either a Jacuzzi or a 'love machine' chair. There is a large r...

Learning from Athena

by DarkestBrown on Sep 16, 2017
Interracial Love

Elisha rode the bus towards home, trying to peer through the glass at the dark world outside; instead she saw only the reflection of what was in her proximity - her face, the face of the guy that sat next to her, along with all the other nameless strangers. That guy had been causing her problems for at least twenty minutes. First he was standing with his ph...

Paula

by tirreno12 on Sep 13, 2017
Loving Wives

I am Italian, so if I say things differently than you say them, forgive me and enjoy the story anyway. This story was edited and co-authored by simaddict. ****** One night my young wife Paula and I were making love in our bedroom; she was being very coy and seemed more turned on than usual. She proposed a sort of riddle game, with a lot of 'what if?' ques...

Bosom Buddies

by BosomBuddies on Sep 26, 2017
Amateur

(This story was originally published as a single, continuous narrative -- but I figured people might have fun playing around with other outcomes for the characters. Please feel free to contribute, thanks!) ******** I turned eighteen a month into my senior year of high school. Skinny, shy, good at math; I was last pick for the basketball team and last pick fo...

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Wet Miranda's Coed Shower

by Wet Miranda on Sep 12, 2017
Exhibitionist & Voyeur

Back when I was a freshman in college, I met my good friend Sarah McKinley. She was always wilder than me, and always encouraging me to be more daring. She was always the girl at the party who would drink more shots of tequila than the guys, and the first girl at the party to flash her breasts. (Actually, she was usually the only girl at the party to flash h...

Fun at a Pioneer Camp

by russianguy30 on Sep 14, 2017
Group Sex

All characters are 18+ * My first sexual experience happened when I was a group leader at a pioneer camp. All group leaders were friendly and I had a relation with Olga from another group. This freshman was slim, long-legged with wavy hair to her slender shoulders. Although the girl was a real knockout, she was very shy. When we were at the white-sand...