Sissy Boyfriend Stories

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Dolly

by ofloveandlust on Sep 14, 2017
Anal

He was in a downward spiral. He understood that. It had started with his separation, an escalation in his depression, the loss of his job, and now a slow steady alcoholism fed by the proximity of his favorite dive bar to his new, cheaper, crappier apartment. The highlight of what had become his life was the short plump little bartender that served him his fi...

April Goes to Senior Week

by clarkoverns on Sep 12, 2017
Exhibitionist & Voyeur

I started dating my asshole boyfriend Brian at the beginning of our junior year in college, when I met him at a party thrown by my sorority and his fraternity. He's not the worst boyfriend I've had, but he thinking we're going to get married, so he's incredibly jealous. And for a college girl like me who just wants to have fun, he can be a real buzzkill and...

Playing Out Ch. 02

by cyanskye on Sep 16, 2017
Novels and Novellas

Chapter 2: Swing Set It has been a while since I have been in this part of town. The fall air feels refreshing as my friend and I walk into the patio of this funky little place. We find a table near the pond where the mannequin now sports a stylish scarf to ward off the chill. The red lights glow warmly in the branches of the trees. My friend Gina goes to t...

Ellie's Decision

by tickle23 on Aug 31, 2017
Fetish

"I... I can't. I'm sorry." Ellie gazed at Tom, apologetically. "I don't understand. We've been together for two years. Do you not trust..." "Of course I trust you. Trust has nothing to do with this." There was a long pause as Ellie shifted the weight of her five-foot-six frame on Tom's bed. "Then why won't you... do it, for me?" Tom replied while still em...

Contempt Prior to Investigation

by Gina_B_33 on Sep 25, 2017
Anal

"Fuck you! I never want to see you again!" I almost shouted at James, my boyfriend, without regard for who else could hear. And then I gathered up my books and stormed out of the diner. Later, back in my dorm room, I tried to explain to Beverly, my roommate what he'd done to piss me off so much. "Without warning, he just tried to jam it in me. The pain was...

After Dinner Delights Ch. 02

by greygotskills on Sep 14, 2017
Group Sex

The Morning After Good friends Tyrone, Dawn and Jenny all lay sprawled out in Dawn's Queen Size bed as naked as the day they were born in deep slumber after a raucous bout of drunken, frenzied three way sex the evening prior. Dawn was the first to awaken from a buzzing sound. It took her a moment to register what it was. It was coming from one of the mobile...

Grandma’s Crushing Scissor Lesson

by kandor on Sep 13, 2017
Fetish

Mrs. B., as Josh called Mrs. Borden, looked incredible. The successful businesswoman had just gotten home from work and was making dinner for her granddaughter Julia and Josh, Julia's boyfriend. They would often come to the older, divorced woman's house to keep her company. Julia and Mrs. B. were close, and similar in their athletic beauty. And try as he...

The Hymen Theory Ch. 01

by seriouswriter12 on Aug 18, 2017
First Time

Thanks coloryourworld for the edit... ===================== "Spaghetti with meatballs. Something is not right." Not bothering to look up and completely ignoring the comment, Samantha Morris continued grating cheese on her pasta. "Want some?" "Maybe later," her roommate replied, sitting on one of the four kitchen stools attached to the breakfast bar and e...

Her Wild Side

by cjpeaches on Sep 16, 2017
Group Sex

The bathroom was completely full of steam. Melissa could not see anything as she stepped out of the hot shower. She found the bathroom door and opened it to release some of the steam. The steam slowly cleared and Melissa took a deep sigh. She felt so much better for a hot shower and had soaked her muscles so that they relaxed. It had been a hard week at wor...

Study Group Sex

by gentlemom on Aug 31, 2017
Group Sex

PART ONE After my girlfriend Jenny and I broke up, my social and sex life seemed to go on hold for awhile. I found that I now had lots of time to perfect my masturbation skills. Jenny simply moved on to another boyfriend. I began to see myself as just one more entry in her diary, but that didn't keep me from bringing her sexy body to mind as I lay on my bed...