Raising Tommy Stories

1,000 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com

Esther's Story

by Tara_Neale on Sep 19, 2017
Novels and Novellas

CHAPTER ONE "It's a tradition," Esther reminded herself as she pulled the box from the top shelf. For twenty-five years, since her son Tommy was just two, she had decorated their house from top to bottom with ghosts, vampires and ghouls of all shapes and sizes. She, herself, would dress as a gypsy and read the cards for children of all ages in the neighborh...

Bare Tommy Ch. 02

by jane marwood on Sep 25, 2017
Fetish

Tommy looked up, suddenly aware of a presence in front of him. He was still strapped to the slender punishment frame, although the young nurses had finished liberally applying unguents and liquids to his bottom and legs. Somehow, his tight confinement to the frame had seemed to give him comfort, some stability perhaps. He had seemed to be able to relax as...

Tommy and Betty

by licksit on Oct 11, 2017
First Time

This one is for you "J." I would never have finished it without your encouragement. Enjoy. * Tommy missed Amy; her sweet pussy, sexy ass, tasty thighs: all of her. He lay in bed at night trying to go to sleep; thoughts of Mrs. Harris, Agnes, and Amy running through his mind. He held his soft cock in his hand and sighed and then his flaccid member began to...

Tommy's Neighbourhood Ch. 06

by TheTitLover on Sep 25, 2017
Mature

Thanks to EndOfStory my forgiving and tireless editor. Feedback is always so important, so remember to comment or send me direct feedback, no matter how long the gap is between me posting the story and you reading it. Getting feedback often draws me into writing a bit more on one of these stories, so if you like it, make your contribution by dropping a bit...

Tommy Has a Babysitter

by Charles Petersunn on Sep 25, 2017
Mature

This is a story of a somewhat odd relationship. It might not be the cup of tea for everyone, but that is, of course, the nature of erotic fantasies. We all have quite different fantasies, and not all of them will I enjoy or expect you to enjoy. This story is classified in the May/December (mature) genre. It also has CFNM and submission themes. For those who...

Tommy's 18th Birthday Present Ch. 01

by leBonhomme on Sep 25, 2017
Group Sex

I have been trying to think of a present for my little brother's 60th birthday and suddenly remembered what I had given him for his 18th. I didn't really given it to him, but I was more involved than I expected. I am sure he couldn't have gotten that present these days, which says when it happened, long before internet and smart phones. My name is Jessica,...

Tommy's 18th Birthday Present Ch. 02

by leBonhomme on Sep 25, 2017
Group Sex

"Jess, show him what we like, need, like Sue is, but Tom can't see why," Ann insisted. Fuck! How did I get talked into this. Yeah, I wanted to rub my pussy - had been since I had spread my thighs and let him look at it - but I couldn't do that! Sue was, however, her fingertips hidden in her hair. She moaned and looked at me and murmured: "Forget he's your...

Tommy and Andy Watch Porn

by benimble on Sep 16, 2017
Novels and Novellas

I was sitting at the computer naked, watching lesbian porn and jacking off. Two teens and an older woman really had me going, and to tell the truth I was this close to losing a load when I heard Andy. "Hey, Tom, you awake?" "Yeah upstairs," I called back. "Grab me a Pepsi on your way up." A minute later he appeared. "Here you go dude" he said, placing t...

Tommy Awakens Ch. 01-04

by HotTommy777 on Sep 13, 2017
Erotic Couplings

Chapter One -- Priscilla awakens my sex life "Life is sweet," I was thinking to myself as we laid together, Sarah spooning from behind me, her carefully manicured bush rubbing against my right cheek. It would be just a matter of minutes before our love making moved from hugs and caresses to blissful, awesome sex. Once again I began to think of how I got to...

Tommy Awakens Ch. 09-11

by HotTommy777 on Aug 30, 2017
Group Sex

Author's note ... Sequence matters. Consider starting at the beginning. * Chapter Nine -- Life at Home Sarah and I were sitting out on the patio, still discussing last weekend's fantasies having turned to realities. "Well, at least my ass doesn't hurt anymore," I said. "Like mine didn't? You and Ralph got me pretty good. Reality isn't always as good as...