Gay Stirrups Enema Stories

490 results
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Blackmailed: Weekend with Bill Pt. 02

by hasnoalias on Apr 3, 2019
Gay Male

All characters in this story are over the age of 18. ***** Dinner that night was pretty simple. Bill grilled some chicken. I was kept naked the whole time and I was getting used to the free feeling of staying this way. I kept thinking about what the next day had in store for me. I knew Jeff would probably join, so counting Bill that brought the number of m...

Brent's Prep for the Prison Doc

by woofdaddy2 on Aug 18, 2017
Gay Male

After a few weeks of being used by first the prison ward and then rented by the prison to entertain local men, it was time for a full medical exam. The Warden did not want his rent boys spreading any diseases so they were tested every two weeks. The exams included tests of their mouth, penis, shit hole and blood. The exams were no too uncomfortable, it was t...

Old Man Discovers... Ch. 11

by tnwriter on Sep 14, 2017
Gay Male

last sentence of chapter 10...and try to keep from laughing.. Late the next afternoon the phone rings. "Hello." It's Fred. "Hey Mack.How's it hanging. Bet you laughed your ass off yesterday watching me walk home." " It was difficult not to at least chuckle", I said. "Well I spent the rest of the day and part of the night sitting in front of the computer...

Turning the Teacher Ch. 03

by Dave933 on Aug 18, 2017
Gay Male

Finally, we had everything I had been looking for, and 'Charlotte' and I loaded back into the car, and I drove us back to the home she owned as Charles Wild. It was mid-afternoon. "Okay Charlotte, I think you should wear one of your sexy new outfits this afternoon, but I'll let you pick. Tennis girl or Hawaiian beach babe?" "Um - I think tennis girl," she...

Team Physicals Ch. 01

by blondeallover_00 on Oct 15, 2017
Gay Male

Greetings to all my voyeuristic readers. My name is Trisha and like you, I have a special appreciation for the well formed male. Most of you, I am sure, also appreciate males who are physically excited by other males. I have come to share that appreciation even though I am female. Let me tell you how I and my bisexual husband arrange encounters with usua...

Death in Key West Ch. 10

by sr71plt on Sep 14, 2017
Gay Male

Conclusion I came to with pain at both ends. I was coming around because I was having my face slapped hard—and I couldn't seem to be able to reach out to ward off the blows. That was because my hands were tied together at the wrists and my arms were drawn over my head and attached to a hook behind me. The pain on the other end was because I was naked and Ja...

Jack & Walt Ch. 02

by lovebuns on Aug 18, 2017
Gay Male

[This is my second offering here at Literotica. I had several responses to my first story, and found that I loved hearing your thoughts, praise and criticisms...please let me know how you like this one!] It had been a little over three weeks since that surreal Friday evening that I lost my anal virginity to my roommate and best friend, Walt. We had both bee...

The Toy Boy

by highwayman2 on Sep 1, 2017
Gay Male

I met them at my regular gym. I had noticed them noticing me right from the day they first showed up. Both were in their late 40's, early 50's, good looking and still maintaining attractive physiques. Finally one Friday night, the taller of the pair, Bob, approached me and asked if I'd like to join them for a drink. There was a nice lounge right next door t...

Paying Rent Ch. 02

by JailBird Dreamer on Sep 16, 2017
Gay Male

A loud distorted voice came out of the metal speaker box in our cell that announced tier time was starting. I had only been asleep a couple of hours but I could still taste Jermane's cum in my mouth. I got up and headed out of our cell and went over to the deputy's station to get my special pink razor and head to the shower like I was told earlier. As I got...

A Prank Has Consequences

by pepperedpig on Apr 13, 2020
Gay Male

It all started with a break-up, a big blue dildo, and a prank. The break-up was with a girl I had been seeing for the past couple months, Rosie. I had tried to communicate with her that I did not want a serious girlfriend from the start, but as time went on she fell for me; the feelings unrequited. Of course I felt guilty, but it seemed no matter how many t...