Strapon Boy Stories

106,036 results
Orientation
Length
Source
Infinite Scroll

Amy Says Yes

by Serafina1210 on Sep 13, 2017
Fetish

This is an entry in the April Fools' Day contest, so expect a bit of goofiness. It's a hard story to categorize, having elements that might have put it in Group Sex, Erotic Couplings, or even Romance. It finally landed in Fetish because its heroine has certain, um, fixations - but it's mild as Fetish stories go. Length: about 14,600 words. Tags: Straight sex...

Ann Berrybush and the Elevator

by Cold_Eyes on Sep 14, 2017
Exhibitionist & Voyeur

Author's Note Ann Berrybush and the other characters in this story are not original. They originate from the Ann Berrybush stories posted on Yahoo Groups, of which there are now hundreds of stories by numerous authors. In most of the stories, the hapless, repressed schoolmarm Miss Berrybush is stripped in slapstick fashion, usually by her student nemeses, A...

Letters From Mrs. Claus

by Von Hauffen on Sep 2, 2017
Erotic Couplings

Me and my partner found these last year while searching a missing person's apartment for clues. Who knows what happened to the guy. All I know is this was the best lead we had and the NYPD sure as hell ain't flying up to the North Pole to investigate. Long story short: I made me some copies before turning them over to evidence. Believe what you will. But the...

The Greatest Liar Ch. 01: My Awkward Phase

by alexandrarios on Jul 3, 2019
Transgender & Crossdressers

Chapter 1 My Awkward Phase The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne in the Newspaper Office, our refuge at University High in Los Angeles. A g...

The Only Time is Forever

by GoneGray on Jul 9, 2019
First Time

The author reserves all rights, except for those ceded to Literotica, per the rules. ***** Bill jerked his hand back as the rose thorn punctured his thumb. Sucking on it, he looked at the row of bushes his wife had planted, many years ago. He never enjoyed all the care they took. But, he had kept them looking tidy & lovely, 22 years later, as they gave him...

M.E.L.S. 7YL

by gabthewriter on Sep 14, 2020
Romance

If you are happy with how MELS ended, do not read further. If you would like to see what would happen with a reunion with David, this is for you. This one is for an amazing fan who rocks!! 7 Years Later: I sat on the transport holding Ben's hand as he slept curled up in the seat next to me. He was a large boy, for 6 he was huge. Just like his father. I l...

Vivian Ch. 03

by scienceguy950 on Oct 5, 2020
Fetish

Vivian pegs and administers strong discipline to her subbie boy, who is learning to accept his role. Suggest you read Chapters one and two of this series first. Hope you enjoy it. The morning after our discussion and more at Vivian's, I was relaxed and looking forward to our rendezvous at the pool, reassured our activities were to be mutually agreed upon....

The Panty Club Ch. 05

by nikki_2021 on Sep 18, 2017
Fetish

Amber stood at Claire's door, hopping from foot to foot, hoping that she'd answer it soon. Amber had been drinking heaps of water during the course of the morning but had avoided going to the toilet, wanting to be ready to piss when she got to Claire's house. It was starting to seem that she might have had her timing a bit off though, because she could bare...

My Fantasy Weekend Ch. 07

by Pro_Ball_Player on Sep 14, 2017
Fetish

Message from author: I know it's been a long time since the last chapter of this series was posted, and I apologize for that. It was unavoidable. This story pushes the edges of many envelopes, especially in this chapter. If you haven't read the previous chapters, you might not understand some of things going on in this chapter. * I looked into Julie's eye...

Royal Affliction Ch. 08

by AutumnsBreath on Sep 15, 2017
NonHuman

Please note: There is a tiny bit of gore in this chapter. ***** Sybari felt her stomach drop. It felt like she her body was being stretched, though it didn't hurt. Inertia hit her as if she'd come to a sudden stop, and she found she was kneeling on a solid surface. Her fingers braced against dusty worn floorboards. Warm firelight shone from spots around he...