Gay Prostate Exam Milking Stories

55,123 results
Orientation
Length
Source
Infinite Scroll

Another Visit to Nurse Rachel

by doctorwes on Jun 9, 2020
Fetish

There is a certain amount of medical play in this story, namely an enema before sex. If that isn't your cup of tea, then you might stop reading here. Otherwise, it's a fun little tale about a cute little tail. Please note that all characters are over the age of 18. This is a sequel to Taking Care of Mutual Needs. In previous stories Dave had met up with his...

Riding Cindy's Bicep

by thomstevens on Jul 15, 2020
Anal

This is the fourth in a series of stories of Cindy introducing her boyfriend to anal strapon play and fisting. Who could have imagined that it could have all began with a single finger. Cindy playfully stuck a finger up my ass and I moaned with pleasure. That was where it began. Soon we moved on to her fucking me with a strap-on, something I never imagine...

Lunch Break

by scienceguy1970 on Oct 6, 2020
Romance

Diana sat in her office frustrated by life's cruelty. Her husband was having prostate problems and thus had no sex drive while she was at the height of her sexual desire. Masturbation usually got her through the rough patches, but the toy she usually used had finally run down and had broken yesterday. It didn't help she had spent an hour before work shopping...

Becca is a Whore Ch. 02

by Prossie_Becca on Oct 19, 2020
Fetish

Before starting, let me explain a few thoughts. The experiences that I am sharing are real. At times I will change the names of people where it might expose who they are, but other than that, they are true. My sister is a sissy CD, her name is julie (Pretty_Sissy_Julie). It was her idea that I join Lit and she encouraged me to start writing. For that reason,...

Caught Out Again and Again Ch. 04

by grgy56 on Oct 5, 2020
Transgender & Crossdressers

Caught Out Again and Again Ch. 4 So here I am in the living room with my girlfriend Cheryl. Seems I never learn anything. When she said she wouldn't be back until late this evening, I thought I'd enjoy the day dressed "full girl". Unfortunately (?) she came back just after lunch to get some files she forgot and found me dolled up in the kitchen. She was t...

The New Lodger Ch. 02

by BmthAdmirer on Sep 16, 2017
Transsexuals & Crossdressers

For some weeks Marc and me constantly headed up the town on the pull for guys mostly but to my surprise Marc had been interested in my Trans partner and how we met and of course my other Trans friends that were always out and about in the pubs and clubs of our home town. It wasn't until late one night after a drinking session with friends and no sign of a s...

Hole in One Pt. 01

by barkirk on Sep 19, 2017
Loving Wives

Dan walked down the hall to the copy room and stopped hearing his boss call out his name. He turned to see the fit 50 year-old man behind him. "Mr. Hill?" "Dan, I was just coming down to see you. Bill said you play golf?" George Hill asked. He studied the young man who was recently hired on. He guessed, 25-30. 160 pounds, 5' 11". Athletic, at least he hoped...

Rob, Robin and Darin Ch. 03

by insatiablerob8 on Jul 31, 2018
Group Sex

The phone rings, "Hey Rob...how's it goin?" "Really good...how'bout you? I know its finals week...I'm sure your feeling some stress." "You got that right, but I got through most of them, already...one more and it's not till Friday morning. I'm really looking forward to our weekend together...but I...um...can't really wait." I suspected by the tone that so...

Soapland Ch. 02

by heavenlyKK on Sep 17, 2017
Exhibitionist & Voyeur

Yuunagi was a high-class call girl who catered to wealthy Japanese businessmen when they were in town. She was considered to be one of the top guns in the business, and getting her for the video was a coup...allegedly. She looked like she was high maintenance. Her price to appear in Soapland was excessive, as in two thousand dollars excessive, but Donkey wa...

Enough Bickering! Ch. 03

by SEVERUSMAX on Sep 19, 2017
BDSM

The next morning, Gavin woke Natasha and led her into the bathroom so both of them could shower and brush their teeth. "Thank you, Master. I'm glad that we fucked last night. I've been wanting you to screw me for a while now. I love you, Master," she declared. "I love you too, Natasha. You're a damn good slave. Now, together we need to plan for the party t...