Sissy Boy Stories

107,893 results
Orientation
Length
Source
Infinite Scroll

Fable 2

by neonie on Jan 22, 2009
Fan Fiction

Like the start of any great adventure you are born... Upon giving birth your farther yells to your mother: "Its a ...What's next? Its a boy! Its a girl! What's next? Its a boy! Its a girl!...

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Wrong on So Many Levels

by RubyRedLips07 on Sep 18, 2018
Toys & Masturbation

Every month some girls complain about horrible cramps, having to change their tampon, their bitchy attitudes, how insensitive their boyfriends are to their ridiculous qualms, etc. I'd like to see them handle my monthly courses. The week before my period comes, I get turned on. By practically anything. The smell of a boy within two feet of me, makes me a...

Golden Daze

by CarrieQ on Oct 3, 2018
Transsexuals & Crossdressers

I met Matt in a basement bar below a cheap hotel in Kensington. My first impression of him was that he was rather fat, my second was that he was a cheapskate. He asked if I was hungry, and when I said yes, he bought me a bag of crisps! Still, he also bought me three large Proseccos, and as it was a quiet Wednesday evening, I agreed to go back to his room wi...

Dani and Paulie Ch. 01

by dani247 on Oct 31, 2018
Transgender & Crossdressers

I only ever told my father one lie. That was about the boots. I was about to turn 18, jobless, directionless and pretty screwed up to be honest. There had been rows, fights, shouting matches and long frustrated silences about what I was doing with my life, but I had formulated a plan. Kind of. Two years prior I had finally admitted to myself, and no one else...

Rayne Ch. 08

by Undercoverwriter on Sep 19, 2017
Romance

The crew of the Eclipse gave their captain a wide berth. For Rayne was a man driven, he was exhausted, haggard and beside himself with worry. Maria wasn't in much better shape, as she too was out of her mind with worry. She prayed for a vision that would lead Rayne in the right direction, bringing them to Gabriella's side, but no visions came. She paced th...

My Domination Ch. 2

by sub-alan on Sep 15, 2017
BDSM

After being dominated that first night, i was surprised that i enjoyed it, so much so that my cock grew throbbing and aching for it's Mistress' touch. i eagerly awaited my Mistress' arrival from work, she had left a note containing very specific instructions as to what i was to do that day. Mistress had left out a pair of her red see through bikini panties,...

Hairy Pecker & the Sorcerer's Cock

by BigDonGStone on Sep 16, 2017
Novels and Novellas

I was discussing the popularity of a certain movie franchise with a friend, and how these movies have a tendency to show up in quickly thrown together porn send-ups. As we sat around discussing this phenomenon I started thinking about how well this particular franchise could translate to an erotic story line. What happens at the school? How do teachers educ...

The Ride

by Water Tiger on Sep 12, 2017
Fetish

After I've ridden your saddle, you tell me that you think I'm ready to be ridden for real. You remove me from the saddle and place a medium size plug in me, which is held securely in place by the harness that I have on. It's a leather jock type that allows my cock to be strapped to my stomach by two leather buckles. My hands are bound behind me to the strap...

A Fluttering Wildflower Ch. 04

by Rockwell on Sep 14, 2017
Erotic Couplings

Morning came and it was Gina who woke up first. Alfie was snuggled by her. She carefully lifted his arm that enfolded her and stepped out of the bed. She flung in his long sleeved white shirt and padded to the bathroom. A note was taped on the mirror that read: 27 Oct, 04 Hi G, Chris and I woke up ahead of you and took the liberty of taking some coffee an...

AAA Plumbing

by rufun2001 on Sep 14, 2017
Anal

The way I see it, all white women are whores only for black men. It never ceases to amaze me how easily we arouse them and how eager to please they are. I'm glad I'm not a white dude, going around all pussy whipped. "No! You're not getting any anal because it's dirty." She'll tell her white boy friend. The next day, I'll be there and I'll have her beg on...