Shy Girlfriend Stories

94,140 results
Orientation
Length
Source
Infinite Scroll

Thank You Sarah

by unclehans on Sep 18, 2017
First Time

After I left university last summer (after gaining a BSc in computer science), I moved back to Sussex - still a bit of a geek and, I admit, still a virgin, I decided that this ridiculous situation had to change. My girlfriend at my public school was the daughter of a vicar and never allowed me to put my hands up her blouse in case her father found out. But s...

Shared by a Strange Couple

by cutemaid on Aug 30, 2017
Group Sex

CHAPTER 1 The Girl on the train Recently I was travelling on a train. I had a few days off and was on my way to visit my mama and papa. The carriage was empty at first and then this girl, about my age, got on and we started to chat. I always show a lot of cleavage and this girl kept staring at my titties. I cradled my titties in my hands as I licked my lips...

Dakota's Surprise Pt. 02

by mfan2112 on Oct 6, 2020
Transgender & Crossdressers

Dear Readers, I hope you find this story interesting. Unfortunately, there is not that much sex in this part, but there will be more in future parts. Please consider reading the first part if you have not done so already. Special thanks to my reviewers who helped identify many errors, but I am sure a few still exist. If you would like to be on my team of edi...

The Math Tutor

by Bettybod10 on Sep 12, 2017
Erotic Couplings

My Sophomore year in college started very dismal. I had moved into my own apartment and missed the chaos of the freshman dorm. The friend that was to be my room mate had a family crisis and she wouldn’t be returning to school this year. I was alone and had scheduled more than I could handle especially in the math department. I admit, I am math dumb but in or...

My Hot Cheating Girlfriend

by Namsbitch on Sep 17, 2017
BDSM

My first hot girlfriend made me a perverted cuck for life. This was my initiation into the power of female sexuality and the control that a dominant woman can have. The time was the early 1980s before AIDS, and we were both in high school. Her name was "M". She was a beautiful, sexy, 18 year old Italian girl with auburn hair and luscious, full breasts. She...

Window Shopping

by VinsanityOrElse on Sep 16, 2017
Toys & Masturbation

I had been having a bad day, my boss was being a bitch, and my girlfriend was fighting with me for no good reason. So I asked my best friend to meet me at the coffee shop so I could talk to her about it. My girlfriend would be pissed when she found out I was meeting Denise, but I didn't care at the moment. As I pulled up to the coffee shop it seemed pretty e...

Shy Girlfriend Fucked Hard

by mini420 on Feb 12, 2019
Erotic Couplings

It was 6pm on a Friday evening and I was just getting home from work. I unlocked the door and all the lights were off downstairs. I called to my girlfriend Mini and got no response. I went upstairs to check and found her asleep in bed. She works early so this wasn't unusual for her, but she was naked with no covers on her. I rarely get to see Mini naked li...

Mellissa's First Blowjob

by Sean Renaud on Sep 14, 2017
Erotic Couplings

"You know you really don't have to do this if you are uncomfortable with it. I won't hold it against you." Jake said trying his best to sound completely sincere. The fact was he was going to be very disappointed if he didn't get a blowjob that night but the last thing he wanted to do was pressure his girlfriend into something she was uncomfortable with. "I...

Window Slut

by SlutProblems on Dec 2, 2019
Exhibitionist & Voyeur

He could see through me, as if my skin was a windowpane, his eyes searching deeply into my troubled thoughts. I knew that I wasn't normal. I knew I wasn't like the other girls. They were so focused on the upcoming dance competition and spoke of little else. I never felt the way that they did. I danced because I had nothing better to do, but there was a longi...

Fun In Cabo

by cindy_4u on Sep 13, 2017
Erotic Couplings

These are my true stories. I am a 23 year old petite blonde. The sun, the beach, the pool and the ocean mixed with some drinks are just the perfect combination for a weekend of fun. Cabo, two years back, I took a trip with my girlfriend with only two objectives:- 1. Have lots of fun; 2. Fuck as many guys as we can. This story is about the best fuck of th...