Sissy Boy Sex Stories Stories

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I Dream of Her

by MagnaCumLiterate on Sep 16, 2017
Letters & Transcripts

J, I've been thinking a lot about your question, the one about what I really want, and the answer has been writing itself in my head for weeks. It's time for me to put it into words for you. You asked: "What is it that you want — in your heart of hearts — that would make you really super happy? A rich woman to keep you and encourage you to pick up hot men?...

Dead Roses Bloom Blue Ch. 04

by AuroraErotica on Apr 20, 2020
Erotic Couplings

The Damaging Winds of Change "Babe, that's Natalie, from the restaurant last night, correct?" I asked Bianca, as she was driving the two of us home from Tamara and Pete's. "It is babe, isn't she just the sexiest thing ever?" Bianca was so excited. "Keep watching Daniel, she gets pretty full on." Bianca insisted. The video message was Natalie thanking Bia...

Sissy Boy Secretary Ch. 09

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine had enlisted the help of her neighbor's daughter, Tammy, to help in obtaining a big business edge for her company, now it was Tammy requesting her help. Tammy's mother was divorced from her husband after an unfortunate chain of events, some of which were Tammy's fault. It seems that Tammy's father was quite a jealous man when it came to her Mother, he...

Sissy Boy Secretary Ch. 04

by Hotenuf4u on Sep 19, 2017
Fetish

Arriving at the office 15 minutes early, walking past three of the other secretaries, noticing them smiling and giggling when they glanced my way. Elaine must have told them of my secret desire to wear panties. Today's choice was the white lace thong pair, which felt good as they rubbed against me as I walked. Feeling my face turning red, I walked faster to...

A Sissy and His Master's Hand

by keptsissy on Aug 8, 2018
Fetish

AUTHOR'S NOTE: No character in this story is under the legal age of consent. They are all 21 years of age or older. No sex act in this story takes place other than between two CONSENTING adults. No character in this story does anything against their will or is seriously hurt, permanently physically harmed, abused without prior consent, maimed or killed. Ever...

I Hit a Grand Slam in Seattle!

by TheBusinessMan on Aug 22, 2018
Erotic Couplings

This is an adult sex story; all the characters are of the age of consent or older. Please read my previous story "Why I Eat a Lot of Pussy" for background. Thanks for your views and votes. **** It was Friday night in Seattle. January. We had flown up the evening before from Los Angeles, first landing to drop off Catherine's daughters in Vancouver so t...

The Jewelers

by mollycactus on Sep 16, 2017
BDSM

Author's note: my BDSM stories are mainly D/s in nature – there is no Literotica category for these, so if you do not like D/s, you can skip this story. ***** Molly had taken on a new submissive male, who had what seemed to her to be, a strange need. Kneeling before her, Robyn explained his desires. "Please, Miss. Cage my cock so you'll be completely in c...

The Cock Clock Ch. 04

by HarveyMarcus on Sep 26, 2017
Erotic Couplings

WARNING: The following story is for the entertainment of ADULTS ONLY, and contains descriptions of explicit sex. If you are not an adult, or reading sex stories upset you, or you are offended by subjects of a sexual nature - do not read any further! This story is for entertainment only. It contains adult oriented material. This is a work of fiction. The a...

Made Over Ch. 03

by gbr2004 on Sep 15, 2017
Fetish

This story involves forced cross dressing, gay sex and bdsm scenes. Don't read if not into these scenes. * I had met a man in my apartment building and he had invited me to join him at a club he goes to in LA. I was a naive boy from Kansas attending USC and I had no idea what I was getting into. The club ended up being a gay leather bar and before the nigh...

Mistress Barbara Calls Ch. 05

by goamz86 on Sep 19, 2017
BDSM

Letter from the author: This chapter is more about control and domination. There is some sex, but not as much as there usually is in my stories. If you are looking for a stroke story, this is not your story. There are some bisexual/gay elements as well. If you are into the elements I listed, please read on. As always, constructive feedback both positive and...