On the bottom

I was poking around the .net on Friday night, after a chill dinner with friends, and saw that a guy I spoke with a few weeks earlier was online. He's a very good looking, beefed-up muscle stud who lives in Midtown. Hot enough to go into the category of "if he's up for fucking around, I'll travel." He was up for hooking, and DID want company, so in the cab I went.

His profile says "Top/Vers," so I thought there was a possibility of my fucking him (his pictures showed off a fantastic shelf bubble butt). The guy's profile said that he was looking for "Fun or more. Hook or LTR." I always like to see that on a hot guy, because then I think..."what if."

His place wasn't that great. Typical small Midtown, railroad one bedroom. He answered the door in only a towel, showing off his huge beefy pecs, and tight, ripped stomach. He was about my height (tall), and had very short hair. His head was shaved in his pics, which I don't particularly care for, so I was glad that he had some hair on his head.

He asked me to hang out while he took a quick shower. I thought it was cool that he trusted me to just hang out in his living room while he was showering. I certainly wouldn't trust a trick in my apartment while I was in the bathroom...probably because I had my digital camera stolen.


He came out, went into the bedroom, looked back at me standing in the living room, and jiggled his tight ass, indicating that play was to begin.

We started with deep kisses. Our tongues went as far down each others throats as they could. We got on the bed as one unit, keeping our lips locked. He pushed me down to his dick, and I gave him head like a champ. His cock was average at best. Even if I'm topping, I love having a nice slab of meet to play with. This wasn't that, but it certainly wasn't anything to laugh at either. His smooth nut sac matched his dick (although his dick didn't really match his body). He exchanged the favor, giving me a nice blow job, while slowly and gently trickling his fingers under by balls and around my hole. Then I realized that he was probably expecting to introduce my hole to more than his finger.

The dude came off my cock, picked up my legs, and stared eating me out. My legs ended up on his shoulders, and he was now kneeling up in front of me, rubbing his dick against my hole.

BANG. I was right. This guy actually thought he was going to fuck me. THE NERVE. Well...not like I stopped him. I said that I'd never been fucked before (honest-to-God truth), and that we could try it, but that he'd have to be cool and patient. He said he'd go slowly, and was clear about the fact that he wanted this to be enjoyable for me.

I understand that it takes a very talented top to break a guy in...a talent that frankly, I don't have. When I've tried breaking a guy in before, I've either been too aggressive, lost patience or couldn't stay hard. None of those applied to him. He was so cool about it all.

He put on a condom, and we tried it unsuccessfully in numerous positions: on my back, all fours, sitting on top, etc. It was not easy, nor enjoyable. There were a couple different times that I gave up. Once, as he was behind, doggy style, he began to put it in, and I literally had to bite the pillow. I felt like such a girl for doing so, and was getting very frustrated. We talked about how many people say that it's usually easiest to break into the world of bottoming by sitting on a dick at first, because then one senses that they're "in control." I didn't know what I was to be in control of, really. Yes, in control of getting that dong in my ass, at my own speed, as deep (or not) as I wanted, but what else? I didn't care about the active/passive "roles" as much as just being comfortable. Also, the attraction and interest I've always had in getting fucked was the opportunity to give myself over to someone. The opposite of being "in control."

On top of him I went. I tried to introduce my hole to his covered cock, but I just kept tensing up. I wouldn't let it in. The more I tried the more difficult it was, of course. I gave up, rolled the condom off his cock, and went back to making out and rolling around. I was so frustrated with myself that I became distracted by the fact that I wanted this to happen. So I asked to go at it again. I wanted one more shot.

Since the closes I came to getting it in was on top, I straddled him again, grabbed some lube, and slowly inched it in. It worked. I wasn't really sure if it was all the way up there, perhaps because it wasn't too long, but when I reached behind, I felt that it was indeed inside me. I wasn't at all interested in getting fucked raw, so I came off, put another condom on his dick and got back on. This time, I guess because he opened me up a little, I was able to get it in without as much effort.

I rode him for a couple minutes, which was fun, but there was no amazingly euphoric feeling going on. I was told that getting fucked, "makes your toes curl." This wasn't doing it. However, I don't think any size dick would've done it to me this go around. I was too focused on making sure that both my hole and I were relaxed, and getting used to this unique feeling. The idea of getting boned by this huge (I mean, he was really huge) muscle dude also helped me stay in the moment.

I wanted to try it on my back, so together we flipped over. He was now on top, banging me with my legs on his shoulders. I wish this felt great, but it didn't. Not at all. I couldn't stay relaxed and all of a sudden got self-conscious. My hole kept clamping down involuntarily every time he pumped, which was quite painful. After a short while I asked him to pull out, which he did.

That was it.

We messed around a little bit more and blew our loads (I blew a large load, and would've liked to do it while I was getting fucked, but a) couldn't take anymore banging and b) wasn't staying completely hard throughout). I hope as I get more and more used to it, these things work themselves out.


On the way back to my place, I felt like I wanted to see this guy again. Did I want to because I let him be my first, or because I was really interested? I felt vulnerable and a little sad. Nothing too serious, and it didn't stick with me, but still...

The next day, I thought about it a little bit more, but wasn't as down as I thought, or was the night before. My hole was a little sore, but nothing that interrupted my day.