Sissy Girlfriend Stories

60,576 results
Orientation
Length
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Infinite Scroll

Boy Plus Girl Equals Love

by Samuelx on Aug 18, 2017
First Time

Hello, there. My name is Stacy Jane Bourgeois. I've got a riddle for you. How does a chick who's fat, ugly in the face, has a huge plump ass and an aloof personality gets to become the most popular female on a college campus teeming with rich and sexy women? Who in hell would let her become so popular? Either it's an act of supernatural intervention or there...

Underneath The Dance Floor

by Keysersoeze on Sep 13, 2017
Exhibitionist & Voyeur

"So what's the surprise?" Jess was in the back of the cab, next to her boyfriend Erik. "Oh, I'm not sure - something someone told me. And if I told you, it wouldn't be a surprise." Jess wrapped her arm around Erik's shoulders. "You're such a tease, you and your surprises." Erik turned and kissed his girlfriend - then kissed her again, raising a hand...

A Friend in Need Ch. 01

by hubbylovesit on Sep 19, 2017
Group Sex

"Are you sure he'll be home?" Amber asked looking at me. "Yeah, I told him that we would be dropping by, I want to buy some cards off him." We were heading to my friend Tom's house that day to buy a few things but at the same time I had a few other things in mind. Tom was twenty-one, the same age as me and had been my best friend since the fourth grade. Be...

Greg and Shelby's New Sex Life

by yaowa on Sep 14, 2017
Erotic Couplings

My name is Greg and I have been dating my college sweetheart, Shelby, since freshman year of undergrad and now coming up on 25. We recently moved in together in a small but cozy 1 bedroom apartment close to the city. Shelby loved being in the city surrounded by people, while I enjoyed my solitude so we settled on the apartment not too far from the city but c...

Confession of a Panty Thief Ch. 02

by Cicero6 on Sep 13, 2017
Fetish

I lived in a Stockholm apartment for a year. The old five story building was narrow and had six units per floor - typical for the neighborhood on my street, BirgerJarlsgatan. I lived on the top floor and encountered all of the other tenants at some point during my stay. The building had its share of beauties, young and old. Most of the time I’d see them in t...

Get Away for the Month

by evilbread666 on Sep 15, 2017
Fetish

The sound of the car doors slamming shut signaled the welcome conclusion to our five hour drive. My girlfriend Samantha and I had been driving for what seemed like ages through forest and rivers on our journey to get to her aunt's house. It had taken an airplane ride, but we had reached a destination far different from home, and it started off quite refreshi...

Small Penis and Trip to the Doctor

by LittleChasteGuy on Sep 12, 2017
Exhibitionist & Voyeur

A few years ago, after several interviews, I finally got that good job I'd been seeking. The last step was to pass a pre-employment physical with the companies chosen doctor. The HR person gave me a sealed packet of forms to be completed and the name of the doctor to call. I was somewhat taken aback as the doctor's name was obviously female, and that meant s...

The Domestic Plumber

by Moondrift on Aug 17, 2017
First Time

Sixty years ago I was serving an apprenticeship with a plumbing firm. The plumber I was working with was called Sid. We must have made a funny looking pair because I was over six feet tall and Sid was about five feet one. At one time we got a job replacing old iron pipes with lead pipe. There were about two dozen rental houses that had been built on the che...

Girlfriend's Birthday

by masturbatingindc on Sep 16, 2017
Group Sex

This story is 100% fantasy based on actual people (whose names and personalities have been changed) Julia and I were lying in bed together one night, having just had some amazing sex. You know; the kind of sex that's romantic, lusty, raw, and compassionate all at the same time. The kind with the perfectly simultaneous orgasm. She had spent the last week o...

My First Girlfriend, My First Love

by George_McGuffen on Sep 17, 2017
First Time

All the names in this story are changed for the safety of those involved in the story... I never had any luck with girls when I was younger. Maybe it was because of my home situation or whatever. I had it hard the first 15 years of my life. I was beaten and molested which made it hard for me to be open with people and meet others because I was affraid of wh...