Some true and some fantasy you decide. My first post so hope you’re all kind.
I grew up in a VERY Christian family where marriage and kids was the only way to go.
For years I lived the “straight” lifestyle but the only fun I had was with my trusty right hand and porn mags as the internet was not around then. Every programme on tv that was gay orientated I’d tape and watch time and time again.
When I was nearly 30 I decided enough was enough and came out to my parents. They were actually fine about it and allowed me to be who I wanted to be.
The first night I went to a club was in St Helens. It was great all these guys and gals there kissing and dancing.
A few guys came over and said hello but then backed off. I didn’t know why what was I doing wrong? Then the barman told me it was because someone had told them I was with the police. Ok I was but did that matter? Yep all down to trust.
Weeks went by before they started to open up. There was a really cute twink couple that kept chatting me up but I was really looking for someone older.
Along came Steve he was about 30 too. A nicely build Blond haired blue eyed trolly dolly with British Airways. Woof was he nice and he pressed all my buttons. He flattered me so much I was putty in his hands and afterwards we went back to his place. We wasted no time and soon we were both naked and making out. He wanted to fuck me and I wanted him too. Condoms were not mentioned. The lube came out and after fingering me for a while, that drove me crazy as it was the culmination of my fantasies for years, he got me to rub it all over his cock. He was about 7 inches and not thick so when he slid it in it went in fairly easily. Was I happy oh yes. He started slowly and after about 10 mins started getting faster and harder. He hurt a bit being a bit rougher but I knew it must get better and it did. After about 30 mins he started grunting and moaning and then pulled out. “Thanks that was great he said and then I better go as he was up early on the New York flight!” What an anticlimax that was.
I drove home with a bit of a smile as I had finally taken a cock and it was raw.
After that he kept making excuses and I decided good riddance to him. I found out he did this to everyone and he had so many notches on his belt you couldn’t count them.
After that I made some good friends and off to Manchester we all went. The New Union on Canal Street did a stripper every Sunday and I was in for a treat I was told.
In we went a few drinks later this big black stripper came out and started his routine. He must have been about 25 and 180lbs at least of pure muscle. When he finally pulled his thong off I burst out laughing. It was SO SMALL! I nearly got kicked out.
Game Time: Prelude
Jake, Sean, and Owen were bored. The three friends were all in their early 30’s, and the usual hook-up apps and casual sex were no longer doing it for them. They were frustrated, and even with all the hot Chicago men at their disposal, they all were craving something new. Something more adventurous. Something that makes a good story.
The three friends couldn’t be more different from each other, both in physical description and sexual conquest. Up to this point, Owen was a serial monogamist. Throughout his adult life, he was always the friend in the long-term relationship, who had a partner, who had the tame vanilla stories to share. He was a medium height ginger, formerly a twink that has evolved into a lanky yet sexy nerd. Equipped with a medium girth, veiny 7.5” cock, Owen has been exclusively a top for the last decade. And Owen is on the rebound. After spending the bulk of the last decade in closed relationships and having his heart shattered by discovering his last boyfriend in bed with a passing-through pilot, he is itching to finally have a bit of a slut phase.
At the other end of the spectrum, Jake has never had a long-term relationship, and has no desire to change this. When he’s not working out at the gym, Jake likes to offer up his hole as a cum dump to anyone that might need a tight hole to unload. Anonymous dark rooms, adult bookstores, glory holes, bathhouses – these are all perfect playgrounds for Jake. With a bottle of poppers and a shot of lube always in his pocket, Jake is prepared at a moment’s notice and perpetually cum-hungry. Jake always has a story or ten for Sean and Owen that blows their minds and hardens their cocks. Fairly muscular, Jake is the type of guy that gets mistaken at first for having “top energy,” but he has no interest in topping whatsoever. A perfectly trimmed beard and impeccably coiffed hair top off his cut physique. That being said, even with taking multiple loads most days, Jake is still looking for a bigger thrill.
Then there is Sean. Sean is a 5’11” cub with scruffy and dark hair who is highly involved in the kink community. With a love for leather, Sean is a bottom verse when fucking, but loves to fist a nice hole. Sean has a prolific Instagram filled with thotty pics of him in jock straps, harnesses, pup hoods, and body suits (and surprisingly has only been reported twice!). That said, for all the gear and toys Sean has collected over the years, he has gotten into a rut with his scenes. Being a very picky person that meticulously plans, it takes a lot to get an invite into Sean’s playroom. This pickiness, however, has led Sean to be somewhat frustrated with his sex life. Despite all his followers online and his likes, he is jealous of Jake’s ability to just let go and enjoy sex wherever, whenever.
Based on their personalities, it is obvious why Sean and Jake were surprised one day when Owen made an interesting proposal over brunch at their favorite diner.
“I think we should play a game, kinda like a truth or dare, but only dares.” Owen blurted out to the other two. See, Owen was itching to let it all go and slut out, but his guilt complex needed someone else to pull the trigger for him. He dreamed of having a dominant man tell him what to do and how to be a cumpig, but he didn’t want to trust just anyone. So, who better than his best friends Sean and Jake to control the fate of his slutty coming of age?
“Oh? Like what? Daring you to dye your hair blue? Or actually show up late one time somewhere?” Jake asked, poking fun at Owen’s obsession for perfection.
“No, like, sexual dares. Like we set up scenes for each other, send time and location, maybe minimal instructions, and then we must carry out the dares from each other.”
Sean was so shocked at the suggestion he choked on his coffee. Jake, however, could see exactly what was happening. His dear tightly wound friend needed a release and was ready to let it all explode. A huge smirk spread across his face. His mind was already reeling at what trouble he could prescribe for his dear friends. He had plenty of favors to call in to give Owen exactly what he was craving.
“Wait, why?” Sean inquired.
“Well, it’s rare that all three of us are available at the same time, and what better way to celebrate the three of us being single than helping each other explore our kinks and expand our horizons. Plus, think of the stories we will have during brunch.”
“I’m in.” Jake interjected. He’s already hard under the table thinking about this. He never would have predicted Owen would make this suggestion, but he is happy he did.
“So, that is two of us. Sean, it’ll be fun… and you always say I need to be more adventurous and spontaneous.” Owen added.
“Fine, let’s see where this goes.” Sean gave in.
“Perfect, the first set of dares have to be executed in the next two weeks. We know each other’s schedules pretty well, so that will help. Let’s start clockwise. Jake, you make a dare for me. I will make a dare for Sean, and Sean dares Jake. At any time, we will text each other at minimum a place and time. Little more instruction if need, but not too much. And any extras we might need to bring. And if this works out, we go counterclockwise and dare some more. Sound good?” Owen said.
“You had this all planned out before even getting here today, didn’t you?” Sean responded.
“Of course, you know me.” Owen answered.
“Well boys, let’s have some fun with each other. No limits here, this is going to be good.” Jake added.
And with that, the game began. The boys continue their normal brunch conversation, but each of them starts planning what mischief they can get their friends into over the next few weeks.
To be continued…
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