Best Day Ever

Story Info
A 3 way day.
1.9k words
4.47
10.7k
3

Part 1 of the 3 part series

Updated 06/10/2023
Created 05/16/2020
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Doublelist CUMS THRU

I`m John and just turned 60 years old, just divorced, and just came out as gay. I`m what some would call your typical late-blooming gay man, who spent 3/4 of his life in denial, always carrying around an itch nothing I did seem to scratch.

I`m a 6 ft. tall guy weighing in at 190 lbs. give or take a few. Reasonably fit from an hour a day on the treadmill, with a few extra pounds on my gut that never seems to get any smaller no matter what I do. My cock is 6 inches uncut thanks to being born in Germany shortly after WW2 where circumcision wasn't normally performed. I have what my newly ex-wife called an "Indian butt", as in not even close to being a "bubble" butt.

Not really handsome or ugly, but just an average, decent looking guy; newly divorced from a marriage that was doomed from the start. We stayed together for 22 years, with the last 5 being one fight after another. Most every one of them was my fault since I felt myself drowning every day, with the surface and air getting further away. Two kids, a boy, and a girl, both grown now. I was surprised, relieved when they were both fine with me being gay. Both said all they wanted was for me to be happy.

So, OK, here I am free to be me. I found a nice 1 bedroom apartment and moved in. Now what? Seek out the nearest bathhouse? Go to an adult bookstore gay section? Cruise local park men`s rooms? Stand in my window naked, waving my cock at guys with a "how about it" look on my face? If that`s your thing, good for you. Be happy and enjoy it.

It`s not for me though. Maybe a holdover from all the years of being closeted, or shy, or scared, or I don`t know all of the reasons. I just knew none of them were anything that got my juices flowing and put a bulge in my shorts.

There were many gay porn videos and stories, lots of my hand working my cock as I put myself into the videos and stories as one of the characters.

In one of the stories, it mentioned how Craigslist used to be one way for gay men to find each other for sex. Off to Craigslist I went and noticed in the Missed Connections everything that caught my attention, when clicked on it would say "Flagged for removal". Then I came on a post saying a big fuck you to whoever was doing all the flagging but offered up a site called Doublelist.com as the new place for hooking up.

Being curious and horny I checked the site and it was categorized by sexual preference. I clicked on the "guys for guys" and in a flash there it was, post after post. Some with pictures, but it said you needed to join to see them; so I did and I looked, and looked, and looked. First I looked for someone in my area, the 33596 zip code. Then I checked what they wanted. Long story short, I responded to 5 postings and waited anxiously for a reply.

You old hands at this know what happened; a big, fat nothing. Occasionally I would get an email wanting pictures of my cock, or ass, or both. Back and forth emails going nowhere. But it was all I had so I kept looking.

Then one day I saw this posting and answered it without many expectations but it sounded so good I couldn`t just let it go without a try. It read:

"Gay couple looking for you to come and spend the day by our pool

Get an all-over tan.

Take a no suit needed swim.

Have a drink.

Enjoy a day full of naked man fun."

Well, it didn`t take but a few seconds for me to answer that ad with a message, consisting of some personal stats and an all caps "WHERE ARE YOU?"

Twenty minutes went by before a message popped up on my email.

"Hi Guy, I`m Sam and my husband is Bob. Before we invite you over to one of the best days in your life (big smiley face) we need two things from you, and both of them are pictures.

We want a face to waist picture and we want a picture of your cock, if hard even better.

We`ll be waiting."

Your wish is my command, Sam and Bob. Five pictures later, I picked the two best and put them in my email back saying, "I'm hoping I make the cut." It was kind of a joke since I`m uncircumcised.

To paraphrase Shawshank, it was the longest twenty minutes in my life waiting for their reply.

"Hi you uncut, handsome devil; this is Bob. Sam and I are looking forward to meeting you in the flesh." They also included their address.

I quickly went to Google maps. Not that far I thought. I printed out the directions and off I went.

It was far enough outside of Tampa so the homes weren`t right on top of each other which made my dick twitch in excitement. It doesn't get much better than privacy for some outside, in the sun naked man, with man, with man play.

Found their driveway, turned in, and pulled up to a modest Florida style home. I was ready for a day of firsts with not just 1 guy, but the fantasy of 2 at the same time.

This was my first time for a threesome, first time for some outside man sex, and the first time for some man sex in a pool. And maybe a chance for my ultimate fantasy, me fucking a guy while another guy is fucking me.

Being a bit nervous since I never asked for any pictures of either of them, I made my way to the door and rang the bell. There were a couple of nervous seconds of waiting then the door opened.

The man answering the door had a shaved head, bushy mustache, shaved body, and was fully nude. Welcome to the world of being a gay man looking for other gay men for sex. I thought I died and went to heaven.

"Hey, Buddy I'm Bob." He pulled me into a good, strong hug.

Bob was around 40-45 years old, 5 ft. 10, maybe 175 to 185 lbs. He had a little stomach paunch above a 6 in. cut cock. Not movie star or troll, just a decent looking guy confident in his skin.

"Come on in and get comfortable, Sam's out by the pool waiting for us," said Bob as I watched his eye travel from my face to my toes and back. His smile grew wider and his cock seemed to be growing stiffer.

Well Hell, if Sam is anything like you then what a day is ahead for me ran through my mind. Bob read my look and said I could leave my clothes on the couch in their living room.

He turned, showing me his smooth, round ass which twitched as he went to tell Sam I was here. I had a feeling he was probably telling him more as well.

I was dressed for the occasion, as minimal as possible. I slipped the thongs off my feet, the Polo shirt up over my head and off, shorts down and as I was straightening back up Bob and Sam came in. I looked up when they came in.

Sam was probably in his late 50's with grey, white hair. He had a clean-shaven pleasant face and a nice smile. He was taller than Bob by a few inches. Sam wasn't shaved head to toe like Bob. Just his cock and balls were hair-free. Sam`s cock was a bit longer than Bob's and a bit thicker. A pronounced head on that half-hard beauty that held all of my attention for I don't know how long since time seemed to stop for me.

They stood there with their arms around each other's waist and I could see Sam`s hand moving over Bob`s ass. Up and down over that ass; stopping for a squeeze now and then. Both were semi-hard and Bob reached down to hold Sam`s cock and waved it at me with a big grin on his face.

I couldn't take my eyes off the glorious cock; it was 7 inches with a pronounced head.

"It feels even better than it looks," Bob said.

I was fully hard by then and must have had a wanting look on my face because Bob let go of Sam`s cock and waved me over. "Come on over here and let`s get to know each other better," said Sam.

I was there in a flash and brought into a three-way hug and grope session that had my head spinning. All this man-flesh to feel, rub, squeeze, and get lost in. Cocks were rubbing against cocks. Hands running over each other`s ass. Then the kissing started.

OMG, the kissing was amazing. I`m couldn't believe that I was kissing another man and that 2 men were kissing each other. They are kissing me and we are all naked in a 3-way hug. I swear I thought I was going to cum, pass out, and shout all at the same time.

"We better relive his stress before he explodes," Sam said to Bob. They both stepped back and went to their knees.

"Bob loves the taste of cum," said Sam as he took hold of my cock and held it by the base. He took and rubbed my cock head against Bob`s cheek, moving it to his lips. His free hand was going up and down my leg, from ankle to ass. Bob`s lips parted and his tongue gave me a lick right on my slit. I shuddered as Bob took me into his mouth. Just the head, with lips holding the head as his tongue traveled around and around the head and giving some light suction.

Sam was stroking me from base to Bob`s lips with a good, perfect grip and back again. I was watching Bob and Sam looking up at me and back to each other. Bob's eyes were closed as his cheeks expanded and contracted while he sucked and ran his tongue over just the head of my throbbing cock. Sam`s hand came up and brushed my lips which parted by instinct. He pushed a finger in and I sucked and licked it for all I was worth. He pulled his finger out and it went right to my ass hole, rubbing, prodding, probing and pushing.

Everything I had wanted or wished for in years of denial. It was happening all at the same time. All for my first real live man with man sex. Mind you, Bob was still working on my cock head. Sam was squeezing and stroking my cock, and then he pushed his finger in me. I didn`t even have time to take it all in. How Sam`s finger in me felt. How Bob`s lips and tongue felt. How having my cock in another man`s mouth felt and how I`m standing here naked with 2 naked men on their knees in front of me.

Sam`s finger pushing into me was all it took and I shot a load of cum into Bob's mouth and stood there shivering in pure bliss. Bob sucked hard, getting all I had to give.

Sam sawed his finger in and out as I clenched hard on it. "Holy fuck you guys," was all I could say. Then the rest of my best day ever really started.

Stay tuned for part 2 of how Bob and Sam introduced me to every pleasure men can have with other men.


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3 Comments
Vincent21Vincent21almost 4 years ago
Well Written

You write clean, grammatical sentences. Your descriptions are economical and fairly precise. Your English education has not been wasted on you. Cheers. That being said, you had me touching my cock as I read. Looking forward to reading more from you.

jehu47jehu47almost 4 years ago
Glad to see someone writing about older men

As I said in the title, it is refreshing to see someone writing about older men coming out. Thanks. I will look forward to reading more!

PissdrinkerPissdrinkeralmost 4 years ago
My kind of sex

Love it, cum gulping, ass fingering and deep man on man mouth action (or mouth on mouth man action)! Thanks.

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