Always Ask

Today I took a risk on a guy I didn't negotiate raw with before agreeing to meet up, mostly because he was really attractive to me-- 27, lithe looking body in his pix, sweet ass, very hipstery arty beardy face. I was kind of smitten and couldn't believe he was hitting me up and things were really progressing along to the point that I would very likely get to watch him sucking my dick within an hour if I kept mum about my desire to ejaculate inside his body. Often I do a weird calculation in my head: with some guys who are really clear about safe-only in their profiles, I will blurt out that I want to fuck them raw because they are (1) not all that cute but I would be happy getting off in them, so I give them the chance to say they want it; (2) totally out of my league so there's probably no point hitting on them but I have nothing to lose because some guys in that league have trouble finding guys who will cum in them; (3) because nothing else will do that day than skin on skin pleasure, no matter how cute the guy is. I've been having enough sex lately that I don't feel starved for the chance to get my bare dick in someone, and yet it's been long enough that if he insisted on a condom I was pent-up enough to probably actually enjoy fucking him wrapped with such full nuts. An odd number of people are hitting on me lately, very attractive people, so I feel kind of like I'm being smiled on by the gods and should not reject these gifts, so I gave him the address and waiting. But I'm reminded I should Always Ask. In the end it's better to know what you're getting into. I sort of feel like an ass now that the sex is over with this kid.

He showed up looking taller and lankier than his pictures, and his beard was well on the way to street person territory. His pictures look way dudely, but in person he was pretty flitty and gay. But we kissed and he kissed really, really nice, and even better, when my hand strayed to his chest he whimpered like a little girl. I have often found that dudes with sensitive chests are very easily led down the primrose path to an illicit fuck with my raw dick, so I felt sort of like I'd hit a jackpot. When he knelt down to suck my dick and I felt his VelvetElectric tongue, I felt golden. He had me hard as a rock and I predicted deep bare pleasure in ten.

The usual trifecta, though, is good head, sensitive nips, and an out-of-proportion love of being rimmed. And the latter, he was sort of missing. He arrayed his lanky but meaty thighs on the bed just so to perfectly show off his crack, the roundness of his cheeks, his hairy balls, his snakelike uncircumcised dick-- the cleanest uncut dick I've tasted in years; not even a whiff of skank under that foreskin-- but when I ate him out he seemed most sensitive on his balls, which made him gasp, but his hole was not responding, even with flicks to his nipple simultaneously; that snatch was nailed shut. It was unbelievably hot having my face in there, though, so I kept up the one-man-show, thinking of at least five other dudes who would be in orbit right now and begging me to do whatever I wanted to their bodies by this point. I tried to slip a finger into his small tight hole, which did feel awfully liquid and sweet inside, but he pulled my hand out; later he clearly stated fingers irritate him. Oh boy. I fooled around with my dick down there a lot, trying to gauge the situation-- could I slip in at all, would he open? Would he just absorb me into him raw without any further negotiation? When he wasn't sphinx like he was pulling away, which didn't bode well.

When I ground my body into his as he lay on his back, he had a strange way of pushing me off him. Maybe it had become clear what I wanted to do. But he also writhed when I pushed myself down on him even harder, and then purred "I want you inside me." I had him suck my dick some more to get as hard as possible to prepare for this, then aimed it down there, and actually popped in for a second. But he pushed me away again-- poor kid, I really am a monster-- and asked if I used condoms. I had actually stored my last SKYN condom next to the bed in case this happened, so I put it on, and as I rubbered up my dick rubbered up too, and I was trying to squeeze into him still very fat but not completely rigid, with all that extra rubbery friction. It wasn't working. "You are really tight," I said, in a bid for the No Shit Sherlock award. I slid off the condom and slicked up my dick with lube, and he reached down for me and held my cock tight. I fucked his hand while holding his hips-- it was incredibly erotic. He said "Yeah a lot of guys have trouble with the condom and everything." I decided not to give up but to keep valiantly trying. He turned onto his stomach again, with one leg hitched up to his side, and I just ate away down there, my mouth getting numb from the lube, but it was so beautiful. His skin was so taught, his flesh so warm and smooth in my hands, those ass cheeks were so inviting. I got very hard in my hand again, and put on a condom HE had brought-- a ridiculous red Lifestyles-- and we tried again. No dice. I got him on his back, and rubbed against him till I was very hard; he still kept pushing me away weirdly and now would no longer kiss me. I suspect he was very annoyed that I'd penetrated him raw at all, even if it was just my very dickhead. But looking at his body, that long dick which did not lie, it was hard and thick with excited blood, made me get hard again-- not as hard as I had been before I knew I had to wear latex, but respectable, and I pushed into him.

It felt mighty fine, and I fucked him hard. Condoms almost always put me in this state of being not very hard and extremely excitable at the same time. I only got maybe thirty seconds of stroking before I was cumming in him. He was stroking his long uncut schlong-- long and lax and velvety like the rest of his body-- and I was ejaculating in the condom and pounding my body against his; he seemed to have no clue I was having an orgasm. Feeling a little ridiculous at the whole thing, I decided to give him a bit more of a ride, and kept fucking as best I could; he got even tighter around me, if such a thing were possible, and now my dick was just accordioning in and out while my softening, gooey dickhead was trapped inside his viselike sphincter and the suffocating rubber. He told me to cum and I said I already had and he said Oh wow really and then he made himself cum while I sucked his nips. And then he reached down, very carefully, and pulled me and the condom out, making sure I didn't spill (and, I suspect, still wearing it).

He took a shower pretty quickly but was not actually all that weird afterward. We had a nice natural conversation while he dressed, and he admired our Christmas tree, which we are going to take down tonight. He had just moved here from Miami but was OK with the cold. He seemed like a good kid. I don't know exactly how he feels about my attempts to get in him bare, but I now wish I'd just headed it off with a simple question from the start. The head he gave me was so amazing that maybe it would have been better to just have stuck with that. But of course when a bottom wants to get fucked it's usually all he will accept, and if he's a stickler for safe, even my own high-skilled ministrations will not sway him. And honestly, good for him. It's his body. If I were the type to make resolutions, I'd resolve to always ask forever from now on, and then be like everyone else and break the resolution by Martin Luther King day...