Shemale First Time Stories

351,086 results
Orientation
Length
Source
Infinite Scroll

Trudy Ch. 02: The Next Step

by Trudydoes on Sep 14, 2017
Erotic Couplings

After that night on the beach with Jack, Trudy was a different woman. Transformed. Alive, yes... but also more than that - confident, carefree... even glowing. Cliche I know. Most of all however she was hungry with desire for more... pandoras box had been opened and now the key was being thrown away; the beast had been freed and would not be going back. Sa...

Elizabeth's Confession Pt. 01

by georgekaplan on Oct 3, 2018
Mature

My Husband has asked me to write this. I suppose it's a kind of a confession, perhaps for us both. I owe him at least this. Though it is not an apology. It will tell many things about the last year of our marriage. (That's wrong, our marriage isn't over, yet.) It infers many things about the previous years in our relationship too. The events in the last year...

Strip Tease Ch. 01

by ladyellen on Sep 12, 2017
Exhibitionist & Voyeur

I looked up surprised as Tom, my husband, swore and brushed the papers he was working on onto the floor. "There's no way I can work this out." He sat back in his chair holding his head in his hands. I went over and put my arms around his shoulders. "Surely it's not as bad as all that." He shook his head. "I'm afraid it's very bad and it's going to get wors...

Slut for All Pt. 05

by Knightofround on Sep 26, 2017
BDSM

It's now been about 3 months since Vikki first sat on my face and had me eat Anthony's cum from her pussy. We have been having amazing sex almost every day since then. She learned about my friends Greg and Maggie's extremely open sex life that is full of threesomes, bisexual encounters and cum covered bondage orgies. Last week Vikki caught me jerking off whi...

Jessica's New Life Ch. 03

by crimfolk on Jan 14, 2019
Interracial Love

Taste and Try Jessica stretched her arms out above her head on the bed and left her whole naked body exposed to him. She kept her eyes closed and savoured his attentions. It had been much, much, too long. His skilled fingers were tracing patterns across her skin and teasing her with the anticipation of where they would land next. However, since she wasn'...

Wives of The Commander Ch. 03

by MTL17 on Nov 21, 2017
Celebrities & Fan Fiction

Disclaimer: I do not own The 100. I do not make any money from the writing of this story. ***** Octavia Blake whimpered in pleasure, partly because she still had her wife Clarke Griffin's tongue deep inside her ass, but also partly because her other wives had arrived. The joy of seeing them was momentarily replaced by embarrassment, her cheeks flushing as...

The Descending of Jessica Ch. 12

by Jessie92 on Sep 19, 2017
Novels and Novellas

Several months ago, I hinted at an epilogue to wrap everything up. Unfortunately, this has turned into not only another chapter but probably should have been two or three. Oh, well. If you haven't read the preceding chapters, you probably should or none of this will make any sense. If, on the other hand, you want to plow right in then have at it. I make no p...

Diary of a High Price Escort Ch. 05

by R_U_Romantic on Sep 19, 2017
Erotic Couplings

Our story continues.. Please read Ch. 4 before starting this conclusion. * Randy's cock remained as erect as before he deposited that wonderful sperm filled load of salty thick semen in my mouth. After licking every drop from my fingers and his cock I looked up into his lust filled eyes and asked. "Do you want to fuck me?" "Absolutely." Was his one word...

Warmth Pt. 02

by NRMathis on May 1, 2018
Non-Erotic

VII A little while later, we hit a snag that put a strain on our relationship. It wasn't sudden, it was gradual, so much so that I'd have a tough time pinning down when it even started, but if I had to hazard a guess I'd say it began around the first week of October. Pine started having subtle changes in his demeanor. He seemed to get a little less touchy-...

From Writing to Reality Ch. 01

by morris40 on Sep 12, 2017
Group Sex

Tom and Tina's imaginative stories on Literotica had invigorated our sexual fantasies, although they had never actually met my wife and me. They had even convinced us to meet them in Tahiti for a week of fun. While we had agreed in principal to swap partners for an evening, sex is never a sure thing with strangers, even after a year of planning. We justified...