[Teen Cumhole] Craigslist Hookup

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I spent the night at my boyfriend’s last night (we’ll call him Jeff). Anyone who has read my previous posts knows I’m a submissive boy and will do just about anything as long as it ends with my hole dripping sperm. I knew that Jeff didn’t have a problem with me taking loads from strangers, but if things are going to be serious between us I would prefer for him to be in control of who breeds me, when they breed me, etc.

So yesterday afternoon Jeff posted on Craigslist advertising my ass and made it very clear that I was looking for loads from experienced men. He got a ton of responses, a lot of them seemed fake and weird, but there were a few serious guys that seemed eager to fill me. Jeff made plans for two of them to come over within the hour (but he didn’t tell me which ones…not knowing which men were coming over made it a lot more exciting), but only one of the guys ended up showing up. More on that later.

To pass the time I sucked Jeff’s cock on the couch and he rimmed me. I never get tired of sucking dick or getting my hole tongued, so I could have done that all night, but eventually the first guy showed up. He was about 40-something, decent body, clean shaven and kinda shy. I’m not particularly attracted to the whole shy type, but this guy really came out of his shell once we got going.

Jeff lubed my hole with some Astroglide to start things off. Let me just say I love this stuff in gel form. It’s not too runny, not too thick, and it’s kind of sticky and makes everything feel silky smooth. Plus I only need a tiny bit of it for my hole to be ready for use. I sucked the other guy off for a while Jeff got me warmed up and then he flipped me on my back and pushed my legs up. He invited the other guy to come try out my hole, which he did, and then they started doing this thing where Jeff would push his dick in, then pull out and the other guy would put his in and pull out, and they kept taking turns dipping into my hole sort of. It was cool to feel how different their cocks were… Jeff’s is very thick to begin with, but the other top had a pretty big mushroom head on him. So the different sensations were interesting, and each of them stimulated my hole in different ways.

At one point our guest was grunting really deep and Jeff goes, “It’s nice isn’t it?” I don’t know why but I really liked that… It was like Jeff was letting another guy use me, showing him what a good cumhole I am. The guy randomly pulled out in the middle of fucking me though and kneeled in front of my face and, for lack of a better term, started choking me. He wrapped his hand around my neck and squeezed pretty firmly, then started tapping his dick on my lips as if to ask me to open up and suck it. This was impossible because 1) I could barely breathe and 2) his hand was in the way. After about 5 seconds Jeff told the guy to get off (thank god) and he went back to fucking me until he came. This guy had the most obnoxious orgasm ever…I’m pretty sure he woke up the neighbors with his grunting and moaning, but who am I to judge. From what I could feel it was an OK sized load. Didn’t make me feel super wet but still managed to drip a little from my hole. Then Jeff finished me off with his own load and I was a happy boy. Hopefully Jeff will do this with me on a pretty regular basis. I’m not opposed to getting fucked by other men, but at the same time I want to make sure it’s under Jeff’s approval and that he’s there with me.

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