Gay Prostate Exam Milking Stories

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Infinite Scroll

Siss the Bride Ch. 03

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Every marriage has its problems, even mine, which is a huge problem considering I'm a guy who gave up every semblance of a normal life to follow hidden fantasies on a spur of whimsy induced by my hot older brother. My life during my marriage to my brother has been built upon submission, only natural when you are a sissy crossdresser and when he has the perfe...

Naughty Paramedics

by Jayegdew on Aug 30, 2017
Erotic Couplings

I reported for my shift as a paramedic with anticipation since I would be working with a new female medic. I had seen her a few times during her training and she was good looking and had a pleasant personality. We did the usual things during the morning checking equipment and responding to various calls and then time for a quick lunch. We stopped at one of...

The Naughtiest Doctor

by n00bwriter on Dec 8, 2017
BDSM

If you are very lucky, you might meet someone at work that you really connect with. Someone who brightens your day. Someone you have more in common with than walking around on the same bit of carpet for 8-12 hours a day. For me that person was Dr Stephanie Benz. As the Hospital's lawyer, doctors were rarely happy to have me rattling around their hallways. H...

The Nurse Next Door Ch. 01

by brahmin on Sep 11, 2017
Mature

I was merely looking for a tranquil, quiet life in the suburbs. Just out of a short, though turbulent marriage, I decided against life in a singles ghetto. Instead, I opted for the distraction of a yard and a small house, while I regained my bearings. Some of my neighbors had other ideas. My usual morning workout routine was interrupted by the sound of the...

Danny's Education

by Greymead on Sep 19, 2017
Transsexuals & Crossdressers

"Damn it, Jem! I'm a doctor, not a sissy!" Jemima chuckled, recognizing my weak attempt at humor as I tried to avoid the question. She was still holding the brief, lavender panties out to me. "C'mon, honey. Just do it this once for me, please?" Her big eyes begged more eloquently than her voice, and, though I didn't care to let her know in case it made me...

Doctor Hardwick, Intern Phase 02

by MagicFingers on Sep 14, 2017
Erotic Couplings

"Wait here. I'll be right back," said Dr. Hardwick, wiping his cum off her face and chest while putting on only her lab coat over her bare breasts. She still had her snug white pants on her bottom half. "Here, let me cover up your little problem in case someone walks in." She said, covering up his still-hard penis with a towel, and gave him a reassuring smi...

Strawberry Milk Pt. 03

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

Now I was planning on going home for Christmas but given how I was changed and changing I'd need some sort of plan and to spend some thought on this. In the meantime I have a few things I wanted to do and that's well... Milking my titties and blending that milk into some of my body lotion and then going out for a walk, get some groceries and do some clothe...

Cruel FemDom Fitness Training Camp

by Dungeon_V on Sep 26, 2017
BDSM

PROLOGUE The lights in the dungeon were dim, but the acrylic cane She whipped through the air was black light reactive, creating a fearful streak of light through the air an instant before the inside of my right thigh seared with pain. The sound of my sudden gasp could not block out the snap from skilled administration of a punishment stroke. I felt I had b...

S-E-B Sexualized Education for Boys

by charmingcharles2896 on Oct 14, 2017
Toys & Masturbation

---------- ALL CHARACTERS ARE OVER THE AGE OF 18 ---------- Authors Note: Hello everyone, I'm back! I've been having trouble getting inspired enough to continue "My Trip to the Doctor" I'll be honest. I wrote this story months ago and just recently revised it to a point where I think it is of good enough quality to share with you. ***** Ms. Rubenkoch walk...

Aliens Use Sex to Invade Humans Ch. 05-07

by walterio on Sep 13, 2017
Sci-Fi & Fantasy

Author's note: I received an e-mail requesting that I write a story about aliens taking over humans and creating insatiable sexual desires. The person requesting this story had read another story on Literotica entitled Hosts. He was disappointed that the author of Hosts did not write any more chapters after the first submission, which is why he asked me to w...