Gay Shemale Mistress Stories

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Internet Holiday

by Sean943 on Jan 20, 2020
Gay Male

My current assignment in Den Haag was nearing completion, time to look for a new assignment; first, I would take a few weeks off. Where would I go, what would I do when I got there. Being a solo traveller has its restrictions. Checking out options on the web, I came across someone looking to share a cabin on a cruise ship. I sent him an email saying, I was p...

The School of Freedom and Love

by Jam18 on Aug 18, 2017
Gay Male

Oh, man, it can't be morning already. I rolled around on the bed and checked the time. "SHIT," I said out loud. It was 5:30 a.m. and I only had one hour left to say goodbye to my room, to my house, to my life. Ok, maybe I was being too dramatic, but being sent off to boarding school wasn't my idea of a great eighteenth birthday present. Yep, that's how I was...

Drunk at College

by johndovinski on Sep 19, 2017
Gay Male

*** Author's Warning: I've never written anything that's published anywhere before. I've read A LOT of Literotica stories and it took a lot of nerve to just write something on here. This story is a bit of an extended fantasy about what I wanted to happen at a very specific time in my life, but names and details have been changed to protect the innocent. Than...

Mind of Straight Married Cocksucker

by silkstockingslover on Sep 14, 2017
Gay Male

Summary: The 10-part philosophy of a straight cocksucker. DISCLAIMER: This story is based on a couple years of research and conversations with straight men who are curious or are cocksuckers. Although I am female, I find a man sucking cock hot, I suppose like most men find two women hot. Thus, I thought I would, based on my many conversations with straight...

Seduced by a Billionaire

by ret123 on Sep 14, 2017
Gay Male

I could not believe it. The woman behind the front desk told me again, "We are sorry sir, but we have no reservation for you and the hotel is completely booked for the whole week because of the meetings and retreat for a major financial institution." "I know!" I said. "I am supposed to attend those meetings and participate in the retreat! Please, help me ou...

Experiencing Oral

by Jjdoesit1 on Aug 18, 2017
Gay Male

This story is of my discovery and my first time with a dildo in my mouth and my first experience sucking a man's dick. Yes, this story is true and yes, the names have probably been changed (lol). All subjects are well over 18. Feedback is certainly welcomed, I will answer any questions as I see them. Enjoy, JJ. ***** The question has been asked "what wa...

Business Trip

by Diego99 on Jul 16, 2019
Gay Male

This is a true story of my 1st experience with another man while away on a business trip. Names only have been changed for privacy... *** I'm 32 years old married with kids and have been straight all my life - up to now. My curiosity about experiencing with other men started years ago because of watching porn. I was initially into lesbian porn, then threes...

Curiosity Brings a New Experience

by toddd0134 on Sep 15, 2017
Gay Male

This is the actual story of my first gay experience. The names have been changed, but everything else is as it happened. I hope you enjoy! ***** All my life, I'd always considered myself straight. Lots of girlfriends, lots of complements on my looks and plenty of opportunity to get naked with the "fairer" sex. Also, a healthy appetite for porn. It was pr...

Finding Out I Love Cock

by 54btmguy on Sep 14, 2017
Gay Male

This is my first story of how I learned I love cock and cum and how much of a slut I like being so although will be somewhat short but hope you enjoy it. ***** I was just out of the service and at 32 my divorce was finalized and I moved back to my hometown and enjoying my new freedom but even though I was out having a good time a couple nights a week I was...

Amazing

by Suavebollo on Jul 15, 2020
Gay Male

At 50, I was still lost as to who and what type of person I was. Being married most of my adult life, I was scared and hesitant to come out of the closet. No one and I mean no one would ever suspect me of being bi or gay, but here I was again, walking into Amazing Lingerie in Dallas. I used to visit bookstores to get my cock sucked, but sometime in my late...