Friday, June 19, 2009


The other day, I met up with a new guy from online. For purposes of this entry, we shall refer to him as Mr. Claus, due to his wealth of toys. I probably won't be talking about him again because I doubt I'll see him again. It wasn't particularly bad, but it didn't end up being my cup of tea either.

Mr. Claus and I discussed using toys, something I'm not too familiar with. We had already decided what we'd do and what we'd use.

I arrived at his apartment and was immediately instructed to strip. We moved to the bedroom where we proceeded to touch, kiss, etc. He eventually moved down to rim me, which was really nice. Then, we moved onto our first "event" that we had discussed previously: the enema. He really wanted to administer one, so I said I'd let him. It was a little odd at first, but I quickly got over it.

After that was done, he lubed up my hole and inserted a small butt plug. Admittedly, I had never used one before. I liked the way it gave me a consistent feeling of being full. We left it in for a while to get me nice and stretched open while we kissed some more.

After having the butt plug in for, probably, 15 to 20 minutes, he wanted to move on to the dildo. Now, I didn't know how serious this dildo was going to be. It was a double-sided dildo, but it was ridiculously thick; like, thicker than a soda can. I didn't think I'd be able to take it. But with a lot of lube, some poppers and some patience, I was able to take it about 5 inches in. It was a lot to handle girth-wise, but once I relaxed enough, it felt so incredible to have my hole stretched open that wide. He kept trying to push it in deeper, sometimes when I would specifically ask him not to, so that got on my nerves.

He worked my butt with the dildo for another 20+ minutes before putting the butt plug back in (which wouldn't even stay in anymore) and getting some anal beads. They were the kind on the plastic string, not a regular string. Those felt pretty hot popping in and out of me.

Basically, we kept playing with these toys for almost two hours, which was fun, but I learned that I'm definitely more into actual sex than toys. And Mr. Claus was nice, but I wasn't feeling it when he would try and push my limits without my consent. It really bothered me, so I probably won't be seeing him again. It was a good learning experience, though. I learned that I love getting my hole stretched to its limits (which I kind of already knew) and I learned that I must truly be a bottom because for the majority of the session with Mr. Claus, my cock was soft but I was completely sexually aroused, which has never happened before. I'm always hard, but this time, I started out hard and the more intense the anal play got, the softer my cock got... but my level of excitement or arousal never dwindled. Interesting to me, at least.

Sunday, June 14, 2009

fresh meat.

So, I've met a new daddy. We'll call him Mr. Moneybags because, judging from his apartment, he's loaded. It's in a prime location and it's pretty enormous.

I met Mr. Moneybags online and after some talking, we decided to jump in head first and meet up late that night, around 12:30am. Boy, am I glad I did. Mr. Moneybags has the biggest cock I've ever taken up my ass. I didn't measure, but I believe it's close to 9" and it's THICK. Luckily, I had sort of prepped myself before going over; I was "getting ready" and, in the process, loosened up my hole a bit. If I hadn't done that, I don't know if I would have been able to take him as well as I did.

We started out with a lot of kissing and touching. He loves making out and body contact just as much as I do. He grabbed a bottle of poppers, shared them with me, straddled my chest and fed me his giant cock, which I happily sucked. Then he laid down on his back and I went down and continued to suck him, taking notice of the staggering amount of pre-cum that was pouring out of his slit. I would squeeze just under the head of his cock and more would drip out, right on cue. I proceeded to lick up and savor every drop of his delicious pre-cum. Mr. Moneybags then lifted his legs up, giving me access to his hole, which I ate out for a long while. He was moaning and loving every second of it. Then, he flipped me on my back and got on top of me in a 69 position, allowing me to continue eating out his hole while he played with mine, stopping only to periodically feed me more pre-cum directly from his cock.

By now, we were both more than ready to fuck, but I was still a little afraid of its size. He got on top of me and put my legs on his shoulders. He asked me if I fuck raw or with a condom and I was honest and told him that it depends, so he asked what I wanted and I requested he wear a condom. (I love getting fucked raw, but I'm not at a point where I'm willing to give it up raw to just anyone.) He rubbered up, got us both good and lubed, and I got myself sky high on the poppers. My hole opened up nicely and he was able to slip right in without much problem. It hurt me a bit, but with a little patience and a little more poppers, I was able to take him to the hilt. As my hole was getting wrecked by this huge dick, I realized that the last time I got fucked by a large cock was probably almost two years ago by a daddy fuckbuddy back home. Since then, all the daddies I've had sex with have been of average (or below average) size. Mr. Moneybags was reaching places inside of me that I didn't know existed. My eyes were rolling in the back of my head. I was moaning gutturally, so much so that Mr. Moneybags asked me to be aware of my volume. Mr. Moneybags had me stretched wider and was in me deeper than anyone else had ever been.

Mr. Moneybags stroked in and out of my loose, slutty hole for a good while until he announced he was going to cum. I provoked him by talking dirty, asking him to fuck me deeper and harder (which he did) and I talked to him as if he were fucking me raw, asking him to breed my hole and spill his load deep into my hole. He fucking loved it and had a huge climax inside of me (and inside the condom). He continued to fuck me slowly while I jerked off and shot my load all over myself, experiencing one of the strongest, most intense orgasms I can recall.

My favorite part about getting plowed by Mr. Moneybags was feeling each inch of his cock slide out of my hole and then back into my hole. Most of the guys I've had sex with push their cock in all the way and kind of just keep thrusting deeper, you know, as opposed to sliding it out and back in. That's probably due to their size; once you're in all the way, if you pull back, it might come out completely. But Mr. Moneybags had about 9 inches of cock to saw back and forth, in and out of my ass. I could feel just how insanely hard he was and I LOVED feeling the ridge of his cockhead exit and enter my hole.

After having incredible sex with a cock like that, I'm not sure if I can ever be completely satisfied by a cock any smaller. Could this be me officially becoming a size queen? Am I going to keep wanting bigger, longer and thicker things inside me to reach my full pleasure potential?