Sissy Boyfriend Stories

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Orientation
Length
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Infinite Scroll

Seth

by VictorianGirl on Sep 11, 2017
Erotic Couplings

He was cute enough, thought Ramsay as she studied what's-his-name's profile in the dim light of the hallway. He was a philosophy major, which meant that he was probably moody. He certainly didn't seem like the frat house party type, but here he was at a Phi Delta Theta party, and Ramsay was becoming rather fond of his dark, thick-rimmed glasses and the blond...

A Karmic Accident

by Seuler on Sep 14, 2017
Fetish

I was washing my hands when the door to the ladies' room burst open and a woman in her late teens or early twenties entered. She did not wait for the door to close behind her before hiking up her denim miniskirt, exposing white cotton, rose-print panties with pale pink elastic. She ran for the nearest cubicle, her shoes clicking on the tiles, the clicking ec...

My Best Friend's Father Ch. 05

by LolaScott on Sep 11, 2017
Mature

Based on my life: Names and places have been changed to protect privacy. Yes this stuff is all true, I cant imagine trying to make up crap like this! My first boyfriend had very fair skin. Where I could stay in the sun for hours and turn a dark brown, poor Ken despite the sunscreen would turn into Lobster Boy before my eyes. Twenty four hours into what was...

Total Domination

by Umakemewannadou on Sep 19, 2017
BDSM

The master/slave games began shortly after i found out that my boyfriend of 5 years was cheating on me. I was so afraid that he was going to leave me, that i would've promised anything, to get him to stay. Turned out, he only wanted one thing. Every so often, when the mood struck him, he wanted to be my master, and i, his slave. And if i didn't do exactl...

My Sexual Liberation Ch. 03

by sluttyflasher on Sep 11, 2017
Exhibitionist & Voyeur

It took a bit of convincing to get James go along with the photo shoot but after I long conversation he agreed. As I have told you previously he is not very open or experimental. I told a half lie and said I was doing the pictures for him. While I would definitely show him the results, I still would have done the shoot if I was single. I spent my Sunday ni...

Opening Night: Act 05

by Smother on Sep 17, 2017
Fetish

Michelle and I didn't venture too far from the seats where Erin had left us for a good portion of the evening. That being our first time at an After Party, we were content on people-watching -- and sometimes animal-watching, depending on the costume -- and having people come to us to socialize. If it weren't for all of the furry, fuzzy, and feathery outfits...

Hitchhiker's Guide to Women

by Goldeniangel on Sep 12, 2017
How To

The other day my boyfriend showed me an email he'd gotten called "Ten Common Mistakes Men Make With Women"... it was written by a man. Which was all well and good, and he got some of the mistakes right, but not WHY they were mistakes. Of course, he was just trying to sell his product - i.e. his book - but I got to thinking, why doesn't a woman write somethin...

Halloween Transformation Ch. 3

by girlboybootsie on Sep 12, 2017
Fetish

I need no urging, and I feel a thrill slipping into my sexy leather dress and feeling it mold to my jutting boobs as Barbie zips it up for me from behind. I then thrill to the feel of my long leather boots sliding up and hugging my smooth stocking clad legs. Barbie then asks me to help her slide on her own outfit, and it is a real turn on to help her slip i...

Being Neighborly Ch. 01

by fictionvixen on Sep 14, 2017
Erotic Couplings

As he parked his car in his driveway, he felt a little irritated. Returning at noon from a morning of running errands he realized it had been too long since he'd spent any time with female companionship. At forty five Dave was self employed, twice divorced, and had no kids to visit on the weekends, no girlfriend to distract him, and it had been at least six...

Adventures in Babysitting

by Clohi on Sep 11, 2017
Group Sex

When Mr. and Mrs. Black asked me to babysit for them Saturday night, I wasn't really that happy about it. I was supposed to go out with my boyfriend, Mike, that night. When I called Mike to break the date, he wasn't too happy about it either. I've been babysitting for the Blacks for a couple of years, since I was 16. Taking care of their kids is no problem....