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  1. My last hall pass was two Saturdays ago, July 15th. I live in a close suburb outside Chicago, it’s basically in the city. As I usually do on my hall passes, I was planning on traveling around for the morning and then posting up at Steamworks or Banana Video in the afternoon. Maybe stopping by Te-Jay’s to get some gloryhole dick as a treat, who knows? I started planning things out on Sniffies and BBRT in advance. I weeded out the usual dozens of other guys who seemed like pic collectors, curious but flaky guys, or guys who were eager-but-way-too-far-out. By Friday night, I had 8 guys lined up in my area who had told me they were solid, all of whom confirmed “Saturday morning for sure” when I asked. Saturday morning rolls around and every single one of those guys flaked. 🤬 Oh well. I get back on Sniffies and start driving down to the Loop. I’m not ready to head to Steamworks yet—I want to get some variety before I make that investment. So I put my Sniffies location next to Te-Jay’s and figure if Sniffies is a bust I can at least stop in to the bookstore over lunchtime to fill up on penis and semen from the tourist crowd. *Ding* *Ding* Two guys message me right away. The first guy is closest to where I can find parking, so I tell him I’ll be to his apartment shortly. Black guy, nice looking thick cock, about average length. I walk in and drop my bag at the same time I drop to my knees. I immediately take his soft spongy head in my mouth, lapping at and massaging it with my tongue. This is the first cock I’ve had in months, and I waste no time getting him hard and pounding the back of my mouth. I take time to suck his balls into my mouth while I jerk his now rock hard cock on my face. I drop my shorts around my ankles and bend over his couch, and line the tip of his cock with my pre-lubed asshole. He’s eager as well, thrusting to the hilt and pumping four times before he starts shooting his hot load of cum deep in my hole. He pulls out, and I feel his seed drip out of my hole and run down my leg as I kneel back down and gently put his cock back in my mouth. We both stand up to pull up our pants, and I see that his cum has splattered all over the inside and outside of my shorts. I point it out and laugh, and he lets me clean up a bit with a dishrag. One load down. I message the other guy that I’m on my way. He’s in town for a conference, so I walk over to his hotel. I do the walk of shame past people brunching on patios that I walked by 15 minutes beforehand, when I didn’t have a giant wet spot on the front of my shorts (and probably another one in the back around my asshole). I finally get to the new guy’s hotel room after navigating the lobby elevator and dodging the concierge. He’s in bed stroking his super thick cock, with nothing but his hat and socks on. He lets me drop my bag and take my clothes off, asking me questions about the other guy who just fucked me—he’s gotta be careful because he has a girlfriend. That’s cool, I don’t judge. I grab my poppers and lube and crawl up his bed until I’m planted between his legs. I start licking his balls as I replace his hand with my own, stroking his meaty dick. I roll each of his balls around in my mouth before licking up his shaft and taking his cock past my lips. Savoring the flavor of his precum. I pause to hit my poppers, and he hits them as well while I go back to trying to fit him in my throat. It’s too big unfortunately. He gets up and brings me around to the couch at the foot of his bed, where I kneel and bend over. He starts rimming me. It feels fucking amazing, his tongue slobbering at my cummy hole. He reaches for my cock and I tell him that I usually have trouble getting hard with guys, so he gets the message. Eventually I need his cock inside me, so I reach back and grab for him to come up and fuck me. I lube his shaft and then take a hit of poppers as I feel his cockhead enter my cunt. He slowly presses inside, stretching me open. It’s the perfect cock for my hole. About 7.5 inches long, thick and tapering out to the base, about 2.25 inches in diameter, maybe 7.0 inches in circumference. I love being stretched out. Despite what I said earlier I start getting hard while he begins to move in and out of my loose pussy. He keeps pulling all the way out of my hole, the cool air a pleasant contrast to his throbbing cock. He says that he’s never felt a hole as hot and wet as mine, even his girlfriend’s, and he needs to slow down or he’s going to cum too soon. I tell him I don’t mind, and as he grabs my hips and thrusts back inside me I beg him to pump me full of his hot semen. He buries his cock balls deep in my hole, his whole body going into spasms on my back as he shoots cum into my guts. I’m flying high from poppers and the feeling that there is nothing I would rather be doing right at that moment than taking loads of sticky cum from random strangers. After his cock withdraws from my hole, I get back on my knees to clean him off, just like the last guy. I love going ass-to-mouth, tasting the penis that was just in my asshole and the semen that he just bred me with. He seems to be extremely sensitive, even my very gentle, very slow ministrations with my tongue seem to be too much for him. Either that or he gets a strong case of post-nut clarity, and appears to be in a hurry for me to leave. I take his cue and get dressed, making small talk before grabbing the rest of my things. I give him a fist bump before I walk out the door. I go down the stairwell this time so I don’t need to worry about the slow elevators. To my surprise I have good cell reception in the stairwell, so I post up there for a minute to figure out my next move. I send a message to the hotel guy to thank him for the great fuck and for giving me his load, then consider my options. It’s getting close to noon. I’m about a 30 minute walk from my car, and then probably 20 minutes to get up to Boystown. I had previously planned to meet up with another guy in Boystown around 1-2pm. This guy had said he could host at his apartment with his buddy who was visiting. He said they could spitroast me… umm, yes please! I check in with him again—we had chatted earlier that morning to confirm how many other guys I had lined up before them—and let him know that I was able to get a couple loads despite my earlier bad luck. I wait a few minutes but still don’t get any response. Another couple guys have messaged me around the Loop asking if I’d like to get fucked. After some back and forth I find that neither one of them can host either. They want to fuck me in a bathroom somewhere. Sounds a little too risky for my blood. I’m a cumdump, but I don’t want to be a cumdump with a rap sheet. I’m beginning to think it’s time to just head back to the car when Hotel Guy messages me back. “Dude I want a second round haha.” 🤔 I reply, “Right now…?” -to be continued-
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