Gay Age Regression Stories

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Finding a Perfect First Daddy Cock

by btmboi335 on Apr 3, 2019
Gay Male

This is the true story of the time I lost my virginity to Mike, an older man I met on the internet. I will always remember my times with Mike. His cock was one of those rare, perfect cocks that you can always recall in your mind in a second, so every time we fucked was memorable. I hope you enjoy our first time as much as I did. ***** For as long as I can...

David the Graduate Student Ch. 01

by WittePiet on Aug 18, 2017
Gay Male

[If you have not already read the two-part story 'David Begins Graduate Study,' you should read that first, as it introduces all the characters] Chapter 21 Jon The Camford Men's Fitness Trust Shortly after his return from seeing his senile Nazi-loving grandfather, it was David's birthday. Although up till then he had not used cosmetics or male fragrances...

Never Too Late

by kindanormalmwm on Aug 31, 2017
Gay Male

I had been getting closer and closer to taking the plunge into gay sex. Each day, I'd pursue Craigslist ads just to see what was happening in my area. After that, I'd read some Literotica stories about first times, getting harder by the minute, until I could not deny myself the pure pleasure of jerking off on cam with some random guy. I loved watching him st...

Hooked Online Ch. 01

by Warm to touch on Aug 18, 2017
Gay Male

This is a fictional work intended for consenting adults over the age of 21. If the first time and only time had not been so wonderful John probably wouldn't go through all the nervousness and anguish again. But that one time John met another professional business man in person and did all the things for him that they discussed in a chat room it was simply H...

One wish

by I.am.all on Sep 8, 2018
Gay

You are lying on your bed, scrolling through your phone, bored out of your mind. You're trying to decide what to do with your time when a letter flies through your window. You're left bewildered, considering the lack of wind, and pick up the mysterious note. ~•~ Hello, lucky holder! You have been gifted with a wish! But not just any wish. No, this is a wish…...

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A Trip Out of Town

by eljayb on May 23, 2018
Gay Male

I have just returned from a three week trip to another city. Before I left I had checked a dating site searching for like minded men in the city I was heading to. I am 77 years old and prefer men around my own age so I did not have any great expectations. I did find one guy who seemed to match my preferences and we exchanged a few messages and agreed that...

Young/Old Hotel Room Fun

by xxox69 on Aug 18, 2017
Gay Male

This is a true account of how I lost my anal virginity. It was one of my first gay experiences, and it happened just after I'd turned 18. More of my sexual adventures will be uploaded if this one is well recieved. A few weeks after my first gay experience, with a guy my own age, I was horny and wanted more. Since I've always found older men to be a huge tu...

A Quiet Understanding

by markindy on Sep 19, 2017
Gay Male

After years of being physically active, I suppose it was inevitable that I'd eventually screw something up. Now in my early forties, the decision to go head-to-head with a bunch of twenty-somethings on the basketball court may not have been the best decision. After straining the muscles and tendons in my left shoulder pretty badly, I spent several weeks with...

Close-Up

by KeithD on May 9, 2018
Gay Male

He wasn’t looking. He was talking to a woman sitting at a table across the pool from me, but he was looking sideways at her and giving me a full-frontal view, so I snapped off a few photos. I captured the whole effect of him, just out of the pool, body beautiful, with beads of water glistening off his body in the sun. Then a few close-ups. One of his male-m...

Military School Ch. 02

by hotchat on Sep 14, 2017
Gay Male

This is the story of a late bloomer.....a kid that never had much to do with anything sexual all the way into his late teens. I am sure there are a lot like me out there, but most of us are too embarrassed to admit how long it took for us to reach full sexual awareness. I guess it depends on your up bringing and where you grow up and who you happen to grow u...