Raising Tommy Stories

46,993 results
Orientation
Length
Source
Infinite Scroll

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...

Moving Day

by TarnishedPenny on Oct 10, 2018
Romance

This is my entry for the Halloween contest. For those bothered by such, it contains a strong element of voyeurism. Have a spooky, scary and above all sexy Halloween! * * * "It would appear that the new tenants are moving in," Miranda said, looking out of the tall window at the street and sidewalk three floors below. "Seedy-looking customer," James remark...

Sinnndy Does Vegas Ch. 3

by sinnndy on Sep 16, 2017
Group Sex

True to his word, Billy let me sleep in. No wake up calls no sexual interruptions. He was even super quiet when he came back from the casino. He wanted to wake me up to tell me he had won 5 thousand, but knowing how beat I was, let me sleep. I woke up refreshed and ready. I looked over at Billy, he was also awake. "So, any big plans for me today? I inquired....

The Murdered Football Player Ch. 06

by WifeWatchman on Sep 18, 2017
Erotic Couplings

The Case of the Murdered Football Player, Ch. 06 by The WifeWatchman The order of my stories to read is: Todd & Melina series, Interludes 1-5, Sperm Wars series, Russian Roulette series, Case of the Murdered Lovers series, Case of the Murdered Chessplayer series, Case of the Executed Evangelist series, The Swap series, Interludes 6-10. The Murdered Footb...

Amateur Theatre

by JC3717834 on Aug 31, 2020
Erotic Couplings

There are any number of ailments that affect older adults. I have been pretty luck to make it to sixty and not have anything life-threatening. However, a gradual hearing loss finally got to the point where I knew I was going to have to dish out the money to get hearing aids. Google searches gave me a decent idea of the type of features I wanted. A friend re...

Valerie - A Deep and Dark December

by estragon on Sep 17, 2017
Celebrities & Fan Fiction

Note- The following is copyrighted. Legal notice appears at the end of the story. * A winter's day, "in a deep and dark December". Sally Thatcher shivered violently as she stepped out of the house she and Valerie Burbon had shared for five years. Sally wore the down-filled neck-to-ankle coat Valerie had given her, but no shoes and no other clothing. Master...

What If? Pt. 14

by wutmytvben on Dec 19, 2018
Loving Wives

Chapter 41 - Mix and Match In a society where the primary purpose of sex is to have children, it seems that monogamy rules. This may be necessary when one considers that right now in our society children are often home for 18 or more years before flying the coop. Monogamy seems to provide stability for this long-term task of rearing children to adulthood in...

The Speedo Doesn't Lie Ch. 05

by FifthEstate on Dec 23, 2019
Interracial Love

This story is posted on the Literotica website; the author does not give permission for it to be reposted or reprinted anywhere else without consent. This is the fifth chapter in a multi-chapter interracial cuckold story. If you haven't read the previous chapters, I encourage you to do so, but I'm confident you'll enjoy it as a standalone too. ***** April...

Shannon's Summer of Firsts

by Obiaha on Feb 6, 2018
First Time

Author's Note: This is the second story I have written involving these main characters. The first, "Caren With a C" is a prelude to this one written from Tommy's point of view, but you don't need to read it first. Be advised that this story is rather long. I tried to put enough action in along the way to hold the reader's attention but it takes a while to ge...

Micheline: An Older Woman

by Nikkiejanes on Nov 4, 2019
Romance

This story is set in late 1970s Quebec City Canada, and is based on the recollections of a dear friend, who was kind and brave enough to allow me to chronicle his cherished memories. ***** We had docked earlier that day and were due to be in Quebec City for about ten days as we had a large amount of cargo to discharge and then even more to load. For once w...