Lost Bet Blowjob Stories

194,727 results
Orientation
Length
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Infinite Scroll

My Friend Kay

by Classygloves on Sep 16, 2017
Transsexuals & Crossdressers

Although I started pleasuring myself with kid gloves and satin when I was 13 years old, I did not completely cross dress until I was in my late thirties. At that time I was living with the sexiest, horniest female that I have ever known. Her name was Kay and I met her when I was working as a car salesman. I had just sold her a new car and was telling her tha...

Gwen Shows Off

by statestreet on Sep 13, 2017
Exhibitionist & Voyeur

My lady Gwen and I had a new adventure you might enjoy. Some of you may recall our experience exhibitionist/voyeur experience in "Watching her watching us". Well, we think we've done that experience one better. It was Friday night. We were free from the cares of the office and had lots of pent up energy to release. Gwen and I decided to head downtown, have...

Bad Weather Leads to Good Sex

by male_man on Sep 1, 2017
Exhibitionist & Voyeur

Recently an old family friend, a woman in her mid-80s (whom I shall call "Miriam"), had to evacuate her building for a few days due to a storm warning (she lives near the water). By the way, don't worry, the story is not about having sex with her! She had nowhere to go and since I live nearby in another building, but not in the evacuation zone, I was asked b...

Laurie Dhue: Beach Bang

by Foxfan69 on Sep 17, 2017
Celebrities & Fan Fiction

I was walking on the beach early one summer morning. The surf splashed water on my legs as I waded knee deep in the cool ocean. The beach was empty of other people this morning; which seemed strange to me as it was a relatively hot and humid day. Off in the distance I spotted the lone figure of what appeared to be a very pretty blonde. She was lying face d...

The Ex watched

by Indianaboy6555 on Jan 20, 2020
Exhibitionist & Voyeur

My ex always had a fantasy about me, and sadly we never got to fulfill it while we were married. I probably wouldn't have thought about doing it afterwards, but one night as we sat at her place chatting, it came to mind. She'd just propositioned me; that wasn't unusual. I guess today you could call us fuck buddies. She was a bit surprised when I turned h...

Committee Work Ch. 04 - Confession

by monkeykinglives on May 13, 2020
BDSM

Submissive Barb's sins are told and penance begins. Barb returns for a Sunday lesson. She tells her dark fantasy, and is sent on her way with instructions, Tags: first communion, white dress, humiliation, whip, rough sex, blowjob, facial Committee Work Ch. 03 - Barb visits on Sunday morning to end things. Instead, she is baptized. Submissive, religion, h...

The Neighborhood Slut Ch. 01

by Aman671 on Apr 28, 2020
Transgender & Crossdressers

It was a cool Sunday morning here at Northwich, a small town known for its friendly occupants and its male stripper bars. The sun was just setting in as middle aged futa, Savannah Vega woke up and stretched her limbs. "Today's the day huh." Savannah said. Today was the day that she was going to meet her daughter's boyfriend. Her daughter, Angela was known...

Letter from Frog's Neck

by justincbenedict on Apr 22, 2020
BDSM

Dear Shoeblossom, I enjoy your letters, and greatly identify with many of your readers. Not a lot of kinky adventures happen in our little hamlet of Frog's Neck, but I can attest to some action here! My wife Eris is my dominant, and at first I think we tried to keep our tête-à-têtes between us, but Eris at some point decided she wanted to expand my horizon...

Kara and Arryn's Fun Ch. 03

by AlexGunther on Oct 6, 2020
Celebrities & Fan Fiction

Last time, Barbara was at home with Kara, on her knees sucking her off. Kara was wearing a collar, handcuffs, leash, and had a buttplug vibrator in her ass. Barbara didn't have to ask if Kara loved anal. After her experience she knew that it was enjoyable. Suddenly, her phone vibrated indicating that she got a text from someone. She looked at her phone. Th...

Sexy Mandy Wanks The Bag Boy

by BAD BOY BILL on Nov 2, 2020
Mature

"Stacking these fucking cans, all I do is stack these fucking cans." mumbled eighteen-year-old Billy Baxter placing another Hunts Tomato Sauce can on top of the wobbly pyramid of cans advertising the red sauce. Billy, eighteen and in his third month of employment at Piggly Wiggly, was frustrated as any teenage boy who was in the throes of puberty. He was ho...