Lost Bet Strapon Stories

183,182 results
Orientation
Length
Source
Infinite Scroll

Stephen's Ride to Heaven

by lovelyladyfaire on Sep 13, 2017
Mature

"Layla, what's taking you so long, you're dirty old man is waiting for you!" I was delighted with his insistence, Stephen was obviously rested and prepared to carry on. I had to admire his tenacity, his absolute willingness to please me with every ounce of strength he had. Admittedly, he very nearly drained me, in more ways than I could, or would, have ima...

Dumb Dare

by m_storyman_x on Sep 19, 2017
Erotic Couplings

On the dumbometer this rated at least a ten, maybe even higher. I pushed myself up from the table and took a deep breath before turning toward the table where she was sitting. It was a stupid bet, or dare, whichever you wanted to call it. In my fifty years on this earth you'd think I would have learned not to get baited like this. John and Eddie were like tw...

Just One Night, The Aftermath Ch. 02

by maxfly on Sep 14, 2017
Loving Wives

I woke early, as usual, and lay there thinking for a long time about everything that had happened the day before, our first in Cancun. On one hand, it had not been as bad as I thought it would be. I can honestly say I enjoyed having sex another woman for the first time in over ten years. The way it had all played out left me feeling confident and at peace wi...

The Payoff

by naughtygurl30 on Sep 16, 2017
Loving Wives

"It was supposed to be a sure thing," complained Susie's husband, Paul. His voice still echoed in her head. "I had specific information. It was easy money." Of course it wasn't easy money. Gilded Ribbon faded down the stretch, just like Paul's dreams of cashing in on a five thousand dollar bet. Five thousand dollars they didn't have. "Where'd you get the m...

Anita’s Phone Tease

by CanadianTease on Sep 12, 2017
Exhibitionist & Voyeur

"Ummmm – is it noon already?" Anita's hand found the alarm clock on the nightstand next to her bed and switched it off. She turned over and lay on her back, stretching luxuriously. Sunlight was streaming through the windows, brightly illuminating the white sheet that covered her nude body. Her blonde hair was spread out on the pillow around her pretty face,...

The New Boss Ch. 03

by Shadowforce1 on Jul 14, 2020
Interracial Love

I woke up to the sound of my phone going off. "Who in the hell?" I said as I reached for it. Looking at the screen, I saw the familiar name of my boss. "Rachelle?" I asked as I turned onto my back. "I want you in early," Rachelle said. "We have a lot to get done!" With that said, she hung up. What was so important that I needed to be in right away, I t...

New World, New Woman

by lilmisstrange69 on Sep 14, 2017
Transsexuals & Crossdressers

Author's Note: First, BIG Thanks to SurferJake for his amazing insight and editorial help! I know this story relies on science that only exists in fantasy, my interest was to look at what might happen if circumstances forced men to become women. I am also hoping this to be a jumping off point for other stories, so please let me know about more chapters. This...

Holly's Croupier Strip

by allaboutthetease on Sep 13, 2017
Exhibitionist & Voyeur

If you read my first entry "Holly's First striptease" it will give you an idea how I try to work stripping into different situations. The last time my lady friend Holly took her clothes off in public was as part of a private function evening at a local social club. Although it had been planned between her and my mate Rob, who was the compare for the eveni...

Blackmailed Bride Ch. 10

by Thors_Fist on Feb 12, 2019
Exhibitionist & Voyeur

The final part of Tanner and Brooke's honeymoon on St. Lucia. This contains scenes of exhibitionism, voyeurism, oral sex, public masturbation and sex, and lesbian kissing. If these things don't appeal to you, don't read further. Chapter 10 - Honeymoon Finale The next morning I was alone when I awoke. Tanner wasn't in bed nor even in the bungalow. I had no...

My Neighbours Wife Ch. 03

by tantricjim on Aug 30, 2017
Erotic Couplings

I have had a few affairs during my working life. I traveled a lot and was away from home for weeks on occasion. Nights alone in a hotel room or in a restaurant, can lead a person to seek temporary comfort. The affairs were seldom of the 'one-night' variety, but usually involved women with whom I became acquainted through my business. The encounters usually...