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The time I [M21] jacked off for a middle aged guy in his hotel room
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Similar to my last confession, this was 10 years ago when I was in college, living in a college town. I posted a NSA classified to Craigslist with a picture of my cock (which you can see on my profile) in search of someone to watch me jack off. At the time, I was really hoping to get a reply from a curious college girl... But instead, I got a reply from a middle aged man who was staying at a hotel in town. This town more or less revolves around the huge university there, so I assume he must be someone's father who came to visit. Can't think of many other reasons why someone would be staying there. In his email he offered me gas money, which made me feel weird I guess, but fact of the matter was my tank was on E so I said yeah that'd be great!

I roll over to the hotel, running on fumes, hurriedly walk past the front desk and find his room number, knock on the door. He answers and lets me in. We don't really talk much beyond "hey what's up". He brings his laptop over to me, sets it on the bed, and says to put on whatever I like. It's a pretty small laptop, I think we used to call them netbooks. Can't remember exactly what I picked, but I think it was a blonde girl giving a blowjob. I pull down my jeans and boxers and start stroking. He's watching me, rubbing himself over his jeans. I more or less ignore him and just focus on the video.

I am getting close, so I turn to him and ask, "Where should I cum?". He replies, "Wherever you want." I have to think about it for a second. Wherever I want? Not on a towel or into a napkin? Should I just blast all over the bed? It still has the covers on...

Uh oh, too late. Guess it's going all over the bed! I start shooting cum. It's not organized into thick ropes, but rather a spray, speckling all the way across the hotel bed's top cover. A drop of two might have hit the netbook.

Welp! I'm all done! I get dressed. See ya later dude. "Do you still want that gas money?" Sure, why not. I think it was a 15 bucks. I fill up at the gas station across the highway from the hotel and cruise on home. I didn't really enjoy this experience of jacking off for a stranger nearly as much as the other one I posted the other day, but I still think about it every once in a while.

Also, I would like to apologize to the hotel staff and future guests. But I'm sure mine was probably not the first jizz on that bed cover, and probably not the last.

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2 years ago