Shy Girl Stories

210,411 results
Orientation
Length
Source
Infinite Scroll

Mrs. Henderson Plays Matchmaker

by skriblur on Sep 16, 2017
Transsexuals & Crossdressers

Episode Two: Mrs. Henderson Plays Matchmaker The story picks up from the end of "Mrs. Henderson Emasculates An Ex". ***** Mrs. Henderson cracks open the parlor door and peeps through. She says to herself: "I just KNEW those two would be friends!" ~~ It's about an hour earlier, and Kimmi's in the afterglow of a very satisfying orgasm. She's nestled in a...

My Lucky Roommate

by Crazylike on Jul 31, 2018
Group Sex

"Hey Christian... Got a random question for you..." My roommate paused, looking curious. He's a young guy, only 19, and rather socially awkward. "Ok, what is it?" He enquired as he continued his cooking. "Have you ever been with an older woman?" I asked it without looking at him, made it seem as casual as possible. I didn't want to spook him, as young and...

My Brown Eyed Girl

by browngrad on Sep 16, 2017
Interracial Love

"Hi, my name is Jack. I'm a rather shy, Hispanic, hard working machine parts sales representative. I'm also a classically good looking, tall, dark and handsome man. Like most men, I have a vivid sexual imagination but unlike most men, I have little courage to pursue the women I'm attracted to. Being unlucky in love and painfully shy leaves me to rely on my i...

Mo' and Mo' Mimi

by dongstar on Jan 15, 2019
Transgender & Crossdressers

"Oh no! Please don't let me miss this train!" Mimi prayed as she sprinted the last few yards toward the special traincar reserved for students of Hyper Academy. Her monstrously oversized cock bobbed comically back and forth, slapping her across the face with each step. The colossal member protruded a full eighteen inches from Mimi's cleavage and was nearly a...

Teach Me

by SilverMuse on Jul 6, 2020
Mature

Mia fidgeted with her cosmo in the crowded London bar. Tonight, she would meet him. Him. The older man she'd been texting for a week. The man who'd kept her awake at night and distracted during the day. The man with the roguish smile, the witty banter, and the dirty mind. Quickly, she opened the dating app on her phone and swiped to Aaron. His phot...

biggest fan

by tid3i3ringer on Feb 25, 2018
Fan Fiction

I heard about a contest called biggest fan in Hollywood. It was about the actress called emma smith She was very famous in Hollywood. I liked her very much had a crush on her as long as I can remember. I thought what the hell I should enter in this contest what is to lose so I did and to my surprise I won. I got a call from some company that I have won the c...

Open in Reader

Mercurial Ends Ch. 06

by TalyisBagley on Sep 16, 2017
NonHuman

*************************** Hello Readers, Again this chapter is a work-in-progress, its timely so I wanted to get it up asap. Once it has been edited I will resubmit it officially. In the meantime, please enjoy it as it is. I wrote this chapter actually 2 years ago -- but life that last few weeks has been hectic and I could get it to Arch Angel to edit b...

Wow Factor & Sandra is Initiated

by alexcarr on Sep 16, 2017
Exhibitionist & Voyeur

"Well of course women like oral sex, didn't you know that." Sandra paused to deliberate her reply for she knew if she said she didn't like it, she might be tho9ught of as square, and not with the modern trend. She went for it, aired her opinion be damned; "I just think it is not at all hygienic, Jasmine." "Well you have a fog don't you?" "What the hell h...

Megan & Jessie #01

by Jappio on Sep 12, 2017
Exhibitionist & Voyeur

**Trying something different with this story as far as organization goes. Title gets kind of huge otherwise.** #1: A walk in the Woods ---------- Part 1 ---------- "Jessie, hurry up and get your clothes back on. What if someone catches us?" Jessie ignored my pleas though. She only gave her care free smile as she peeked out from the bushes we were hiding...

Not So Shy After All

by DarlingNikki on Sep 16, 2017
Group Sex

“I never get to do anything exciting anymore,” I grumbled. “Between college and work, I never even go out. And my job is so incredibly boring. Sometimes when I’m sitting there waiting for the phone to ring, I just want to do something depraved – tear off the stupid, prissy clothes I have to wear and go running into the senior partner’s office screaming or so...