web log analysis Confessions of a Promiscuous Top: Rookie

Tuesday, December 11, 2012


Today I had a rather unusual experience, for me... I hooked up with a guy a bit older than me who was almost completely inexperienced. I typically don't encourage this kind of thing; I'm pretty frequently hit up by guys who aren't sure of their oral prowess and want to be "trained" or whatever. But my dick ain't a good starter dick, and I like to be sucked off by a professional, so I usually shoo anyone who goes on about being a newbie away. This guy didn't mention his inexperience at all when he hit me up; just said he really was in the mood to suck and be submissive. But he said he doesn't do this often and had to be "ultra-discreet." He didn't even want to give me a face pic first, though when I said that was a deal breaker he eventually  relented as long as I super-promised to delete it instantly. He had a nice, somewhat Irish face and a very manly, hairy, muscular but not primped body. Mighty fine, I thought, I'll take it! But then would not give me a number to text my address to, which always freaks me out. In the end he agreed to meet on the corner near my place. Only then, when we talked about how much time he had, and I insisted, as I usually do, on serious head with stamina, did he reveal that he wasn't very experienced but would try his best. He said he only had a little while to spend, which made me think this wasn't going to happen, but when I pressed him on it, he said he meant "only" about 90 minutes! If he was not confident, at least he was eager to spend some time. I only had an hour myself. So I waited for him to come and met him on the corner, and while the typical shortcomings of a very inexperienced guy were evident, it was a really interesting experience.

He showed up looking great, very much dressed and composed like a straight guy, albeit with a sensitive face. He wasn't overly shy or shady, which was nice, and after I asked him if it was cool and he wanted to go through with it we walked back to my place and chatted amiably about the section of Brooklyn he lives in, which is also where I used to live. Once in my apartment he wanted a glass of water and a trip to the bathroom. And then I pointed him back to the bedroom. Up till now, everything was about as it ever is, really.

Once in the bedroom, he stood in front of me and looked down at the floor. His clothes were rumpled and ill-fitting but the shape of his body, with thick arms, powerful legs and a meaty ass, was evident under the bagginess. I sidled up to him and put my hands on his flanks, feeling the hardness of his body, and then ran my hands up and down, feeling his shape. His breathing was sharp and shaky, and his whole body began to tremble under my hands in a way I don't think I have ever felt in another man. I reached around to the very hard, round ass and grabbed into its substance. With the other hand I felt his nipple through the fabric of his shirt. He did not take his eyes from the floor, with his chin tucked into his neck a bit, keeping his mouth far from me. I figured, oh fuck, he's not gonna kiss, this is going to suck. But I was so intrigued by how out of control his trembling was, that I felt a little touched, and wanted to see how this would go. I leaned in even closer, pulled his body to me fairly forcefully, pulled his thighs to me from behind, and ran my beard slowly up and down his neck. It felt like he was going to have a heart attack. He turned his head even more sharply to the side. He actually seemed to be overwhelmed with shame. He said, "I almost didn't come." "Nerves?" I asked, and he nodded. I pulled him close to me again and stroked his body some more. His arms stayed rigid at his sides. "Just relax," I cooed into his ear. "Just relax." He did not seem to be relaxing, but he liked the touching, if the shaking was any indication.

I said, "Why don't you get on your knees and see what I've got for you in my pants." He barely reacted at all, and said absolutely nothing. So I stepped back, unzipped slowly, and pulled out my only partly swollen dick. He didn't move. So with two fingers I pushed gently down on his meaty shoulder. And he sank to his knees, but only gave my dick the tiniest of licks with a small, pointy tongue.

Normally at this point I'd be over it. But I was still very curious. So I held my dick up, pushed it into his lips, and felt it edge by degrees past his reluctant teeth. Once the whole head was in the wet warmth of his mouth, I cooed, "Good boy. Very nice in there." And he moved his tongue over the right spots, but with far, far too much tooth. But wanting to encourage rather than scold, I expressed pleasure at how he was using his tongue, and gave him more praise. "Good boy, good boy," I cooed every time he did something right. He got a little bolder with the sucking and it made my dick start to get hard in earnest, but he was apparently dizzy and losing his balance. He asked for more water, and I gave it to him. Then I pulled off my pants and hopped on the bed with my legs open.

He remained rooted to where he was, still kneeling, staring at the ground!

I asked from my recumbent, lax position on the bed, "Are you OK?" He nodded, still looking at the floor. "Come suck my dick some more," I coaxed, and he stood up, still looking down, and pulled off his pants, revealing small black briefs with a gooey wet spot on them, and extremely muscular legs, covered with wiry white hair. "Come get between my legs," I ordered, and he climbed in and placed himself there, extremely awkwardly, bent over on his knees rigidly, with his shoulders hunched in. I wondered exactly what was going through his head. He took my dick in his mouth slowly again, by degrees again, and I coaxed and praised every part of the way. But his position was ridiculous. "Lay flat on the bed, on your stomach," I commanded, and he complied rather mechanically, with over-quick, graceless movements. He hooked one hand up under my thigh and put as much of my dick in his mouth as he could. At this point my dick really did get very hard; his body looked amazing in this position, with that big ass filling out his briefs, and though it was still extremely toothy, it was also very slippery and warm. I thrust my hips to fuck his mouth a little, and hitched my free thigh up over his back with my foot resting on his ass.

And being wrapped around him like this set something off in him. The closeness of my body to his seemed to open up a deep inner greed. He changed completely from completely nervous to completely un-self-conscious. I stoked his massive, hairy back down to his small, tight waist and he shuddered and whimpered all around my dick. He gagged easily and seemed to choke on only a few inches. It seemed very difficult for him. But he kept going back for more. Then it seemed that the choking was more some kind of emotional cry more than a gag. He sat up and loudly sucked a bunch of drool into his mouth, with a face contorted with something that looked very much like pain, but also longing. He blindly clambered up my body from my groin and sucked on my chest. Then I pulled his face up to me and kissed him.

And he sobbed freely. He kissed horribly-- no lips, all darting pointed tongue-- but his emotion was naked when I put my face against his, and melted and quivered and yelped when I sucked his ear. It was very alarming, but he did not seem to be dissolving into some kind of meltdown... he just seemed absolutely overwhelmed. I pushed him on his back and lay on top of him and he wrapped himself around me, stroking my body in a slow frenzy, and cried out wordlessly many more times. It was unbelievably exciting to me, and completely unexpected. He hadn't told me at this point, but this is when I knew he had pretty much never really, truly been with a man before, maybe just a few dumb quick experiences.

His dick was not hard but was oozing serious precum. He seemed like a complete mess. We switched off a few more times of him sucking me and me grinding him. Once on top of his meaty, compact body again, I slid my dick down between his cheeks and fucked the dickhead against his hole. He began sobbing again, grabbing at my body, holding my hand, stroking my hard, hairy thigh. His inner bottom was clearly blossoming here.

Eventually he positioned himself with his head in my lap and his body on all fours off to the side, so I could reach up and slide my fingers up and down his ass crack, and circle one finger around his hole. I pushed a bit to see how far he'd be willing to go. He whimpered with my meat in his mouth and pressed back against my finger, but was far too tight to take me in. I looked at the clock. We'd been at this for 45 minutes, and I had to leave to volunteer in about 15 minutes. It was time to breach the last topic.

"Do you want to swallow me, or do you want me to cum on you?" I asked. The ad I placed had asked for a swallower, but somehow I thought he wasn't really going to do it. "I know you wanted a swallower," he said, "but maybe next time? You could just come on my face and on my, uh, mouth." I said OK, and asked him to kiss me and stroke my dick. He did, extremely roughly, cluelessly. Whenever I had told him to watch the teeth, while he was sucking me, he'd push me out, jump up, and cry in anguish, "I'm so sorry, I'm so sorry, I don't know how." And I would laugh gently and say "You don't have to apologize, just listen, it's fine." And now with my fat knob in his groping fingers, he said, "I'm so sorry I don't know how to do all this. This is only the third time I've been with a guy."

Bingo. I knew it.

I climbed back up on his body and ground my dick into his extremely wiry, white body hair. Then I sat up to look at his shape. I stroked his body all up and down, and he was just hunched there with his shoulders so defensively closed around him. "I've never been... intimate with a guy like this before," he said. I laid back full on top of him and devoured his lips. He wrapped himself around me again. I began to cum, so I jumped up as quickly as I could, got beside his head, and let loose all over his chin. I came a dozen hard jets, it felt like, and the meatiness of his body laid out before me made me want to just keep cumming. He strained up to take my dick in his mouth several times as I came, but the teeth and the groping was too much for my sensitive tip, so I kept pulling it out. He beat himself off hard. At the end of the pulsing, still pulling hard on my tool, I felt another crest rolling over my body, and let it go, and shot more small drops into his mouth. I looked down to see his own dick now hard and shooting feebly.

I rubbed my face and the room came back into focus. I looked down. He looked like the victim of a horrible Krispy Kreme factory accident-- it was absolutely disgusting the amount of goo amassed under his nose. I'd had a four day load in me, but this was ridiculous. He lay there stoically with his mouth closed. "Let me get you cleaned up, man, that's insane." I ran to the linen closet and couldn't find a hand towel, so I brought him a full size one. He wiped himself down.

"Well," he said, "that was several barriers torn down." I laughed and shrugged and said "I usually get what I want." "Yeah, but you check in from time to time, that's nice." He sat up and looked at me. "I've never been so..." again he hesitated. "Intimate with a guy before. The first time I just got my dick sucked, I didn't even know what I wanted. All that touching helped calm me down."

We talked a bit about how it could be that he'd be married to a woman so long, now divorced, and dating more women, and now in his late 40s, only just realizing in the past year that he is into men. I've heard this story before but am always mystified how this can be, as I was into other boys when I was 6 and always knew I was gay. "Everyone is different," I said in the end.

I gave him some more water and he complimented me on the apartment and the neighborhood I live in. On his way out he hugged me and pressed his face to mine again, and I patted his ass. I told him to take it easy, and he trotted out.

It was quite fascinating to be there to see him react so intensely. Compared to that I feel like an old French whore, used to everything and jaded beyond feeling. It was really something.

I had only a few minutes to clean up a bit, dress, and run to my volunteer stint. It was tough going and long. I had a dazed dinner after, feeling very tired from my athletic manhandling of the rookie's muscular body and hours on my feet afterward. Waiting for the subway to take me home, improbably, I ran into Ultra Meat! This big hot, grinning guy was striding towards me and it took me a minute to recognize him, upright and dressed. He seemed very happy to see me. We chatted a bit until the train came, then in the tunnel under the river there was an awkward silence. On the way out of the train, he reached for my hand to shake it before parting, and then he leaned in and said, "Let me know when you're free."  I shook it, and he raised his eyebrows and wiggled his fingers in my palm before dashing off.

I love sex. I love sex with boys. I love boys. What a life.


  1. Replies
    1. Thank you, Bruce. It was definitely fascinating. I hope I gave him an experience to remember. He says he's just started dating another woman.

  2. Replies
    1. If he had not been so completely carried away like that, Invisible, I would have put an end to it long before, I think. But I have just never been with someone who was so overwhelmed by sex like that. It actually turned me on to be doing something I know he'd never experienced, and wanted more than probably even he would admit.

  3. I love reading your blog! Total bottom here..new and visiting NYC until friday. I would love to discreetly play and be taught how to satisfy you. I am on manhunt. :)

    1. Glad you like it, Anonymous. If you find me online and hit me up, don't tell me you read the blog... I'm actually somewhat prejudiced against fucking dudes who read it, because I write about everything and I feel like it would make me too self-conscious in the moment to be with a reader, and I'm all about getting lost in the moment. But if you don't ever tell me I won't ever know, and then you can find out what it's really like to fuck you!

    2. I have only read a couple of posts not to worry. :) I will be on Manhunt but sadly i don't know your name on there. I will be staying in a hotel in Time Square.. :) i would love to get lost in a moment with you.

  4. What a great, hot post and it was awesome of you to be so patient with him. I have had similar experiences with guys who are new to the game and while not always the most sexually satisfying, often leave me feeling very contented. I'm just curious - would you see him again? Did he ask to see you again? Very cool post.

    1. Well thanks, Loki! Given how infrequently I do repeats even with guys who are really awesome in bed, I doubt I'd get with this guy again. He really did a number on my dick, with those teeth and that pelt of wiry body hair I was rubbing it through. His body was pretty great, though, so I don't feel like it was some kind of charity thing. It was a nice diversion.