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Pride Challenge 15 guys in 30 days!


Coolwave35

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This is my first pride month single in 14 years. I’m gunna try to hook up with 15 guys over the next 30 days to celebrate.  Guys here have expressed an interest in my escapades and I enjoy sharing them so my adventures will be over shared here. Lol 
 

I just enjoyed an afternoon delight with boy number 1, an unpaid hookup from grindr.  He is Pakistani, 24, and works for a super wealthy family that vacations in my home town for the summer as their driver. I met him 3 summers ago and he’s been a consistent source of physical pleasure during June and July. 
 

He texted me this morning and I almost immediately got hard thinking that he hadn’t forgotten about me. He’s into furry otter types. He’s a lean soccer player, 5’ 10ish with a perfect 5-6” dick. 
 

We met at my house and he was dressed in a suit and tie with the cutest little chauffeur vest and sunglasses.  He admired the renovations at my house, asked if I planned on having any pool orgies this summer and said this was the year he’d be participating.  He had been reluctant to engage in years past, but I could tell he has remained interested.  
 

I asked if he wanted to see videos of last years fun, and he said no, I wanna see that in person as he grabbed my junk.  

I went to start making out and he met me aggressively and passionately. I forgot how great a kisser he is.  
 

I undid his the buttons on his dress shirt as he unbuttoned my pants. We were groping each other like crazy and making out around ears neck and mouth. 
 

He went right for my butt and I went for his dick.  I sucked him off as he got harder. I asked if I could take him to the bedroom.  I laid him down on the bed, he still had his tie on and socks. It was super sexy. 
 

He started fingering my hole and I got on top of him.  He came inside me while I jerked off on his abs. 
 

Afterwards we took a shower together and made plans to meet up again. It always shocks me when guys that I think are a total smoke show are into average guys like me, but I’m grateful that he likes me. 

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51 minutes ago, Xavitv said:

lol I don’t think I can’t even get myself to socialize with 15 different people. I’d set my hookup goal to 5 for pride. 
 

btw are we giving a definition for hookup? All the way? Kiss and a handshake? Soup and sandwich? 

Lol. My definition for a hook up has always been at least one dude cumming. It never much mattered to me HOW that happen, just as long as someone left sticky. Lol 

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4 hours ago, Coolwave35 said:

Yes!   No repeats. Lol. That’s the challenge. My highest is 10 different guys in a month, and they were all paid. 

Don't rule out repeats - they just don't count towards the total!  The repeat might be part of a three-way with a first time in June guy!

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Guy number two was super early this morning. I got a message on Grindr. He had no photos posted. In my experience, guys with no photos in my town typically fall into two categories.  They are either an 8 or better, under 45, with a wife or girlfriend, and consider themselves “curious.”  They tend to be visiting and just looking to get off quick with minimal chit chat.   Or, they’re over 60 looking to suck dick anonymously.  I’m typically good with either of those so I agreed to meet.  He didn’t want to come to my house and insisted on car fun, which I hate. I was totally getting scenario 1 vibes so I decided to go for it.  We met at the opening to a nature trail near my house that never has anyone there.  I hopped into his truck and there he was,  about 65-70 years old and looking to suck a load out of me before his cardiologist appointment. 
 

I unzipped and dropped my cargo shorts to my ankles and he blew me for just shy of 10 minutes. I blew a huge load in his mouth and he swallowed every drop. He asked if he could kiss me and I said I’m grossed out by my own cum so I’d prefer not to.  He was very nice but I give the whole experience a c minus. 13 more men to hunt down. 
 

 

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So they can’t all be winners. :( 

guy number 3 hit me up on Grindr this morning looking to bottom. I woke up horny and was all about it. Getting him over was easy because he was nearby. All signs were pointing to fireworks. 
He came over and refused to make eye contact or small talk. He just wanted me to cum inside him. Fair. I like a man that knows what he wants. He led us to my playroom, as if he just instinctually knew where it was.  He got naked before I could get my pants down. He started going down on me and the head was top shelf. I was getting very excited.  He positioned himself on the bed and stuck his ass in the air. I mounted him and fucked him a bit. I pulled out to adjust positions and well, things went south.

He hadn’t adequately prepared. I immediately lost my boner, wiped my boy, and started to jerk him off. He kept saying things like “take your pussy”, “this is your ass today” and put it back in. I couldn’t muster an erection because of the site and smell. I asked him if he wanted to take a break and he said no. He wanted my load dripping out of him. I grabbed a towel, wiped things down and hoped for the best. I got hard again, railed him for a bit and the same thing happened. I told him I didn’t think I’d be able to cum and he asked if he could shoot on me. I said sure. He did, he left, I spent 15 minutes stripping the bed, and 25 minutes in the shower making sure my freckles were still just freckles. 

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Edited by Coolwave35
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On 6/1/2022 at 11:44 AM, Coolwave35 said:

...He’s into furry otter types...

Beware the monkeypox! 😉😄

 

US is hit by MONKEYPOX: Maryland patient tests positive for the rare virus  after a trip to Nigeria | Daily Mail Online

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Ok so guy number 4 takes the cake.  I needed to sleep before I could write. 

He’s a 5’11” masculine Asian pharmacist. He’s stunning. He has boy bander jet black, thick hair. His body is hairless except for some pubes. His dick is about 6.5” and stayed hard for the entire 80 minute play session. He is built like a twink with lean muscle and no definition so you can’t feel his bones. His ass is perfect. It isn’t too flabby or too muscly. It’s prominent and smooth. Smooooooooooth. I had gone on several dates with him last month but couldn’t close the deal because he was so beautiful and I got super insecure. Last night I decided to go for it. 

I saw him looking on Grindr and messaged him. I was super direct because I know he feels like I wasted his time by not putting out last month by our 5th date. 
 

When he got to my house, he said “I don’t know how to start.”  I said I’d like to kiss you. He nodded. He is another one of the most beautiful men I’ve ever been with that I didn’t pay. He had all the physical qualities that I’m super attracted to. What’s better, he was totally into my very opposite body. I’m round, squishy and hairy. He ate it up. I ate him up. It was nice. 
 

As we made out, I took off his jacket and unbuttoned his polo. He untied my yoga pants. We were both very hard. He had been to my house before so he went to my bedroom. I told him I’d rather play in the play space so we went there instead. I took off his shirt and literally tossed him on the bed. I positioned myself over him and I could tell he was really responding to the alpha energy. I slid his pants off and rubbed our dicks together.  We traded off blow jobs for a solid 15 minutes then I started to rim him. His ass was pure perfection. 
 

I went to make out again. I realized I was trembling and he asked if I was nervous. I told him that when I’m intimate with people I perceive to be way hotter than me I get nervous. He smiled and said he feels the same way, and he’s also feeling nervous. We decided to cuddle it out. Then he went down on me again. I face fucked him rather forcefully and I could tell he loved it. I flipped him over and lubed his ass up with my mouth. He was so tight that I just laid there inside him. He started pulsating his butt and it felt so amazing. 
 

We fucked. A lot.  No really. A lot. In different positions, different speeds, we shared control, though he liked when I’d pound him. Unfortunately that’s my least favorite way to fuck but I was a trooper. He came a few seconds after I did. He asked that it not be in him so we blew together on his beautiful body.
 

Then we took a shower together.  Making out and talking about how great it was but how nervous we were lol  it was sweet and had me second guessing this quest. I kinda just wanna have sex with him 11 more times and call it proud lol. 

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Edited by Coolwave35
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So that didn’t last long. Lol 

 

guy number 5 was a 6’1” stocky Brazilian father of 3, that was covered in tattoos.  He was supposed to just suck me off and leave. He wound up fixing my Lutron system too. I told him he didn’t have to and he said whatever keeps him out of the house til his wife puts his kids to bed lol. 
 

he asked if he could take a shower cuz he worked all day. Knowing he was pretty clean, I did wind up sucking him off too. He had a really large uncut cock that was fun to play with and stayed hard after he came. 

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Edited by Coolwave35
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57 minutes ago, Coolwave35 said:

So that didn’t last long. Lol 

 

guy number 5 was a 6’1” stocky Brazilian father of 3, that was covered in tattoos.  He was supposed to just suck me off and leave. He wound up fixing my Lutron system too. I told him he didn’t have to and he said whatever keeps him out of the house til his wife puts his kids to bed lol. 
 

he asked if he could take a shower cuz he worked all day. Knowing he was pretty clean, I did wind up sucking him off too. He had a really large uncut cock that was fun to play with and stayed hard after he came. 

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And less than half a mile away!

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Number 6 was supposed to be a super easy late night blow and go. Except I couldn’t cum and he wouldn’t go. He spent 45 minutes aggressively sucking my dick. He likes rough so I spanked him, choked him and pulled his hair. I face fucked him and he deep throated till he was teary. I hated all of it but he was in heaven. 

 

 

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Edited by Coolwave35
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