Gay Shemale Surprise Stories

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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...

Finally My First Time

by bisibi on Nov 21, 2017
Gay Male

This is the story of my first time with a guy. My name is Simon and I'm 25, 5'10" 13st with a slightly athletic build. I had been bi curious for a long time, I watched a lot of gay and shemale porn and experimented with butt plugs and dildos while masturbating. I first became aware of my sexuality while watching straight porn and being slightly jealous of th...

Admitting My Secret Ch. 02

by HerLittlePiggy on Oct 22, 2019
Gay Male

Chapter 2: Gang Bang "Get on your fucking knees pig," the powerful Dom demanded. I was naked in Master Steven's basement dungeon. My wife Julie was fully dressed and sitting in a chair in the corner of the room watching me submit to a man. I was not gay, but I have always been very submissive and I had recently accepted my bisexuality. My eyes flashed at...

Playing Dressup Ch. 01

by mfs1390034 on Jan 21, 2020
Gay Male

"Sure. Why not?" I said and we went upstairs to his parents bedroom. My best friend and I had watched several YouTube videos about men who dressed up in women's clothing and, after helping ourselves to his parents liquor cabinet, we decided it would be fun to try on his mom's clothes. At first we tried on her wraps and coats and had fun drunkenly strutting...

Then and Now

by FredTR on Jun 4, 2019
Gay Male

I could feel my heart pumping as I drove. Butterflies fluttered in my stomach. It was hard not to speed but I couldn't risk a ticket. I pulled off the highway onto the local streets. Red lights and stop signs were the bane of my existence. And the 30mph speed limit! UGH!! I had found this place by almost by accident, a random comment about it on a chat foru...

A Naked Encounter

by Pissdrinker on Mar 6, 2018
Gay Male

Please note that although this is a true story, I have omitted that we used condoms, we always play safe. Despite whatever Lucy may tell you. ***************************************** Sometimes in winter, if we're not travelling, I go for long walks down the beach nearest to our house. Dave, my boyfriend, often stays at home but occasionally accompanies me...