Friday, June 19, 2009

experimentation.

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?

Friday, May 29, 2009

reconnecting.

Today, I met up with Prof. Daddy, who no longer lives in New York. He was visiting for a few days and wanted to get together with me. It's been over a year since I've seen him. We got together at his friend's apartment, where he was staying. It was just like old times: I came in, we sat and caught up on each other's lives, then migrated to the bedroom. We started with some intense kissing and touching, slowing taking off each other's clothes. He sucked on my nipples, remembering how much it drives me wild. We kissed some more while we grinded our cocks together. I started sucking on his nipples, knowing how much he loved it, before moving my way down to his cock, which I sucked for a while. He broke out some poppers that were his friend's, I believe, and we shared those. After a while, I was ready to feel him inside of me again, so I lubed up his cock and my hole, took a hit of poppers, and sat down right on it. It felt so good to have him back in me. I rode him for a good amount of time, all the while kissing and playing with each other's nipples and taking more hits of poppers. Pretty soon, he announced that he couldn't hold off any longer, so I started riding him harder until he exploded inside me. I kept his softening cock inside me while I jerked off and blew a huge load all over his chest and stomach.

We took a short rest and talked some more until I was ready for round two. This time, I laid on my stomach and he fucked me from behind. He knew he wouldn't be able to cum again so soon, but we both enjoyed fucking anyway. He plowed me until he was drained of energy, so I flipped over and had him finger me while I jerked off again. My hole was extra hungry today, I guess, because he eventually got four fingers inside me--DEEP--and I didn't even bat an eye. I finally asked him to slip his thumb in there, too, just for good measure. Needless to say, this prompted me to have another explosive orgasm.

While I was cleaning up, I noticed that his friend must be a big ol' bottom. Aside from the numerous gay porn calendars in the apartment, there was one of those douche things in the shower, as well as a Ziploc bag with four or five different bottles of poppers on the bedside table. I sort of wondered how I could get in contact with this friend...

Tuesday, May 12, 2009

whoa.

It has been far too long. Last time I wrote, I was 19. I'm 21 now.

I lost interest in keeping up this blog, but I've definitely had plenty of exploits since I stopped writing. There's obviously no way I can recap all of it, but you can rest assured that there has been plenty of fucking, getting fucked, load swapping, and more.

In the past few months, I've discovered one of those backrooms of video stores here in NYC that you can pay a small fee and fool around with guys in video booths and whatnot. I've been there maybe four or five times and it's pretty fun. I love the idea of finding a guy, shacking up in a tiny little video booth and fooling around without saying a word. I went last night and started hooking up with a short Latino guy that sucked me for a little and then wanted me to fuck him. I started fucking him raw for a while and then he suddenly lost interest. Oh, well. There was another guy, though, whose wanted me to jerk off and pretty much worship his nipples, which was a lot of fun. He made some reference to his wife, which turned up the heat. Basically, I sucked his nipples until he was ready to cum, which I promptly swallowed. Yum.

Today, I got fucked by Artsy, which if you'll go back, you can read about. He and I have been fucking every so often over these past two years. Honestly, I cannot believe it has been that long. The last time I wrote about him (which was the only time I wrote about him), I mentioned that we graduated to fucking raw, but he never came inside of me. Well, we have crossed that line, too. For the past year or so, we have been fucking raw only and he cums inside me every time. He's the only guy I let fuck me bare. And, of course I can't be certain, but I actually don't think he has sex with other guys; if so, it's not many. Not that anything's wrong with him, but I just think he's content with just me for right now.

Anyway, today's session with Artsy was hot. It had been over a month since we had last fucked, so we were ready for it. We started with kissing and stripping, which led to lots of nipple play in the bed, which led to me blowing him, which led to him plowing me. I bought poppers last night at the backroom place and I brought them to Artsy's today. He doesn't use them, but I LOVE poppers, so I kept them handy while he fucked me all different ways. I shot my load as I rode his dick and then we took a little break. He fucked me again with me on my stomach (still using the poppers) and I begged him to breed my ass, which he did. This was followed by another break, and then we just kissed and licked each other while I jerked off and came a second time as his load slowly leaked out of my hole and onto the bed. It was pretty fucking sweet.

I'm going to try and keep up with this better. Maybe words of encouragement and appreciation would help with that... :-P

Friday, February 15, 2008

stretched.

I got my hole stretched by Out-of-Town Daddy. I haven't seen him in months, but we regained contact and hooked up. After going to dinner, we went back to his hotel and were back at it like we never stopped seeing each other. He's still just as sexy as ever with his graying hair and his hairy chest and big biceps. There was a lot of kissing and sucking; he went down and ate my ass out for a good while.

Then, he broke out the big bottle of lube and started working a finger or two in me. Once he felt I was ready, he lubed up his cock and pushed it into me raw. He loves the dirty talk just as much as I do, so he kept telling me how much he loved fucking my tight ass, raping my hole, and fucking me like the dirty whore that I am. I fucking loved it. He plowed really hard as my legs were on his shoulders. He grabbed my ankles and spread my legs as far as they went and then turned me on my side and fucked me that way, too. I finally shot my load as he was fucking me and then he pulled out and laid down next to me. We relaxed for a bit until I was feeling randy again, so we started touching each other and whatnot, until I asked him to finger me some more. He put a finger in me and felt around until I asked him to put another in. I kept asking him to put another finger in me until he managed to get all five fingers in my ass. He wasn't fisting me, but he fit all of his fingers in me. Because we progressed slowly, it didn't really hurt, but I felt really full and it was an incredible feeling. After a little while, it got a tad bit uncomfortable, so he went down to four fingers and that was better. As he thrusted his fingers into me, I moaned and grunted and told him to finger-fuck me harder and deeper, which he did. I was quickly brought to a second orgasm.

As usual, he didn't cum that night; it takes him a very long time to cum and we usually get worn out before then. But we were both very satisfied and I was really excited to have gotten my hole stretched out as much as it did. Luckily, though, my hole soon returned to its usual tightness, but I will definitely have to try getting my hole loosened up like that again.

Friday, February 8, 2008

triple whammy.

No, the title of this entry doesn't refer to any sort of group activity. It's just three stories in one entry.

I've been seeing another Daddy. We've met up twice so far. He works for a bank, so we'll call him... Daddy Banks. (I don't have the energy right now to think of a clever name.) Daddy Banks and I met online and agreed to meet in person for dinner. I went over to his apartment and we decided where to go for dinner... and then we hooked up. I honestly didn't intend on hooking up with him so soon (especially before we even went for dinner), but I couldn't help myself.

It was really great. There was no fucking; it was all touching, rubbing, kissing, sucking, licking, etc. We got naked and kissed a lot, followed by him deep-throating me (which was incredible). He had poppers, which he said he doesn't use often, but we used them and it made everything even more amazing. He sucked me until I came all over myself and I proceeded to suck his uncut cock until he shot his load all over my face. After that, we went to dinner and had a wonderful evening. We got together again and had a repeat session; again, no fucking, but lots of kissing, sucking, ass-eating, and poppers. So hot.

I also met another Daddy, whom we shall call UWS Daddy, obviously because he lives on the Upper West Side. We also met online, except we had no plans for anything but sex. I went over to his place and after some talking, we began kissing and I straddled him on the couch. We moved to his home office which had a big futon in it. We got each other naked and just enjoyed each other bodies. One of the highlights was when he ate out my ass; that was truly mind-blowing. Before we met up, we had discussed how we both love cum, so I was looking forward to that. He ended up swallowing my load when I blew in his mouth. Actually, during my time with him, I had six orgasms. No lie. Every time I was about to be finished, I got hard again (or stayed hard) and decided to just keep going. He fucked my ass really well (protected) on that futon and I loved every second of it.

We took a shower together, which got me SO horny. I bent over in the shower and we tried to fuck again (bare), but he wasn't fully hard, so it didn't happen. I sat down in the shower with him standing above me, while I tried to cum my sixth time, begging him to spit on me (which he did) and piss on me (which he said he would have, if he could have). For some reason, in that shower, I became such a disgusting, submissive whore. It became hardcore daddy/son roleplay and he slapped me across the face a few times and yelled at me for trying to let him fuck me bareback. I found out later that he felt that way truly (not that he wanted to slap me, but he didn't want me fucking raw). I was slapped across the face once before by another guy while sucking him and I made it clear that I didn't like it, but I really liked when UWS Daddy did it; I don't know why. He eventually shot his load over my face and body while he stood over me in the shower.

Also, just the other night, I met up with Prof. Daddy again, who I hadn't seen in months. We talked a lot and caught up on each other's lives. Then, of course, we fucked. Now, we were both extremely horny and hadn't had sex in a while, so after we cuddled and kissed for a long time, I sucked him really well, then lubed up his cock and my hole with Vaseline and sat right on it. I rode his cock hard for a while until we both couldn't hold off any longer, so I shot my load all over his chest and he shot his inside me. I got off of him and fingered my ass a bit to feel his cum in me... ooh, I loved it. After that, we cuddled more and talked for a long time before I decided to go home.

I'm definitely meeting up with all three of them again soon.

Tuesday, January 8, 2008

new guy.

I need to apologize. I've been terrible at updating this blog. I just have been very busy lately. Life comes at you fast!

The other night, I got fucked by a new daddy I've been seeing lately. He's very sexy; he is in his late 50s and is very cultured and loves all sorts of art and music and whatnot... so we'll call him Artsy.

Artsy fucked me twice that night. (Both times, he fucked me with a condom.) We started in the living room on the couch with heavy kissing, touching, rubbing, grinding. Then we were tearing each other's clothes off, kissing harder, biting, scratching each other. It was so hot. Then, we migrated to the bedroom for some sucking and fucking. The fucking was really intense. I started being really loud and yelling at him to fuck me harder... which became screaming at him to plow me harder and faster... which became yelling and screaming at him to rape me and hurt me. I have this rape fantasy that I have yet to have fulfilled to the extent of what I imagine, but it involves being relentlessly pounded and forced and manhandled. Ooh, I start dripping just thinking about it...

So, yeah... He fucked me really good twice. The first time, he didn't cum, but I shot my load while he was fucking me with my legs on his shoulders. We relaxed for a bit, and then began fooling around again, which led to another round of terrific fucking. That time, he shot his load all over my chest. Then he laid down next to me and, at my request, fingered my hole while I jerked off. I was in the mood for some serious fingering, so I kept urging him to push his fingers into me deeper (and he got SOOO deep), then to add more fingers. By the end, he had four of his thick fingers in my hole as far as they would go. Holy shit. I never shot such a huge load. I was literally shaking during and after my orgasm.

The next morning, I awoke to him spooning me from behind, rubbing his cock on my ass and touching me all over. This led to a third round of fucking, but this time it was raw. (It wasn't the first time we fucked bareback; actually, every time we've fucked, it started with condoms and then later we would end up fucking bare. Oh, well. Never had him cum in me, though. Not yet...) I wanted him inside of me really badly, so I just lubed him up and threw my legs on his shoulders and he slipped it in. Oh, it was heaven. He flipped me over and pounded me from behind for a little while until he was tired (it was very early in the morning). We jerked off and touched each other until he shot his load on me and my load joined his all over me soon after. He got up while I went back to sleep, but before I left later that afternoon, we had one more jerk-off session. We were both naked and he touched me and played with my butt while I jerked myself to a fourth and final orgasm.

That may have been one of the most fantastic fuck-a-thons I've ever experienced in my 19 years.