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Below are the 20 most recent journal entries recorded in The Cubby Boy's LiveJournal:

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Monday, May 18th, 2009
1:01 am
Adventures in being a top. (Or, adventures in not being the pig bottom for once.)
So I was on Squirt this evening chatting with some neighborhood guys, neither of whom I had met before. One (Kevin) wanted to blow me and the other (Rick) wanted to as well. Luckily they knew each other. So Rick invites us over...

Kevin and I get there at the same time. He was cute and a bit boyish, with some stubble and nice pierced nipples. Rick was thin and hairy with a shaved head. We went up to his apartment and, after we were given beers, start to make out. Then I said, "I gotta piss like a racehorse."

They both got excited.

Rick puts a yellow bedsheet on his kitchen floor and they both get on their knees. They take turns sucking me and drinking my piss, which was having a hard time coming out because I kept getting hard. Rick starts pissing on Kevin, which was really hot to watch. After a while (and some poppers) Rick clamps down on my cock and gets it rock hard. I begin to blow my load, and after I finish off in his mouth he and Kevin make out. Rick is a big cum pig, and apparently so is Kevin. Then Kevin makes out with me, and gives me a taste of my own cum and piss.

After my cock goes soft I can feel the need to piss again. I told them, "I got more piss in ther for you guys." Kevin starts blowing Rick, and I piss on Kevin's face and Rick's cock, balls, and furry stomach. My urethra loosens up and the stream flows pretty hard. Kevin is moaning like a bitch in heat. The sheet under us is soaked, and Kevin is dripping with mine and Rick's piss. Rick began to shoot in Kevin's mouth, convulsing as he does.

He all three collapse on the sheet, chuckling and breathing hard. It was nice to play the role of the top for two enthusiastic cocksuckers like them. I hope we do it again.
Wednesday, December 5th, 2007
8:21 am
A New Friend, A New FB
So... I spent last night with the guy I mentioned in my last post.

He came over and we watched some DVD's. We ordered Chinese. We had fun.

After dinner, he also ate my ass for almost 30 minutes straight.

Here's what happenned:

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Monday, December 3rd, 2007
2:44 pm
New Trick?
Sunday night found me meeting up with a guy I met on Craigslist.

He's black, has a really sexy full beard and a shaved head. 29, 6'5", 350#.

I'm only 5'6", so he towered over me, which always makes me hot. He has tattoo sleeves on both arms. He's a hot, smart, fat, inked black bear--my favorite.

We only met for coffee. Believe me, I tried to get him to do more. He's newly out and didn't want to go back to a stranger's house, which makes sense.

He might call me tonight...
Sunday, November 25th, 2007
2:19 pm
Mall Sex
The really funny thing is, I wasn't actually looking for cock.

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Tuesday, November 20th, 2007
12:11 am
Found a new hookup!

High now, looking at pr0n and jacking off. No one here to fuck the hell out of me, but I can get out the butt plug and pretend...

Fantasy about my last trick:

He comes to the door
i open up naked
stand there hard and greased-up
he steps forward pinches a nipple
grabs my hard cock with a squeeze
pumps once
leans in to kiss me

i'm on the bed, legs in the air
getting eaten
his face fur wet with me
he stands up and kisses me
i long to taste my cum
in his beard
sticking us together with lust
Thursday, November 15th, 2007
10:28 pm
Sex Journal Hiatus

My last post was January 27th. It's been a while. That's because for the last nine and a half months, I had...

a boyfriend.

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Saturday, January 27th, 2007
1:29 pm
Black Bear again...
I got a text this moring from the same guy who fucked me earlier this week.


Um... yeah.

We arranged for him to stop over at my place at noon on his way to wherever he was going.

I opened the door in nothing but a yellow jockstrap and a plug in my ass. He didn't even bother to take off his pants. He just unzipped, pulled our his already half-hard dick, and stuck it in my face as I knelt in front of him. It took me five minutes to get him off, and I was rewarded with a loud grunt and a mouthfull of his seed.

He didn't say a word as he zipped up. He just walked out, confident that I'm addicted to his cock. I slowly swallowed down his thick load and ground the plug deeper inside me as I got myself off, thinking about how he promised me his piss if I earn it by sucking his dick enough.
Thursday, January 25th, 2007
9:20 pm
Black Bear
I haven't been getting much in a while, except for a hot bear who pissed on me a couple of weeks ago.

I got a message from a dude today while I was at work, saying he wanted to 'take care of some cub ass' tonight. He's a really hot black bear, about 6'2" and 300#, with a full beard and a nice thick cut dick. We met up at his place after work, and as soon as the door closed behind me, he pushed me down to his crotch and I sniffed his meaty package. In a couple of seconds I had his cock down my throat and my spit was dripping off his hairy balls.

"Yeah, take care of my cock you little slut. You know you like my dick in your throat."

I deep throated him as I groaned and lubed him up with my spit.

After a few more minutes he pulled me up and pushed me against the door, holding me by my neck.

"Damn boy, you got a nice bubble butt," he said as he squeezed it with his other hand. "I wanna get you ready to take my cock in that tight hole."

He led me to the bed where there were condoms, lube ad poppers on the bedside table.

"Take off your pants and get your ass in the air for me."

I did as I was told and instinctively began to pump my dripping cock. He slapped my hand away and gave me a stinging slap on my ass.

"Don't you get yourself off yet, you fucking slut! It's your job to do what I tell you. I didn't fucking tell you to jack off. Got it?"

"Yes SIR."

He began to probe my hole with his tongue, occasionally slapping my ass and commenting on the redness it produced. After a couple of seconds I was moaning and begging for it like the eager slut he kept saying I was.

"Please SIR I want to take your cock in my ass."

"How much do you want it?"

I told him. He got up and put on a condom (Magnum size) and drizzled his dick with lube. He opened up the poppers and took a hit, then put the bottle under my nostril while pressing the other one shit.


I began to feel light headed as his dickhead stretched open my hole. With one slow steady motion, he entered me balls-deep.

"Mmmm, baby, your hole is so warm." He began to fuck me, gently at first, but harder as he went on. I was jacking myself now despite not having been given permission. I needed it. He needed my hole around his dick. He grabbed my torso on either side ad he rode me doggy-style.

He lasted a long time. Fuck. Heh. I can still feel it. I needed to get fucked so that I felt it afterward.

I came while he was fucking me, and a few minutes later he had mercy on my hole and filled the condom with his semen. We collapsed, he on top of me, and once his dick went down he pulled out, leaving the used condom inside me. I pulled it out and ate his load. I can't let a thick load like that go to waste. It tasted very salty and sweet at the same time.

Now I might have to jerk off again remembering it.
Tuesday, December 12th, 2006
11:54 am
Interactive Porn!
Went to the Eagle on Sunday night... in short, it was a bust. I got cruised by a couple of guys who chickened out at the last minute. I hung out in the men's room. (What can I say, I'm a fucking pig?) Nada.

So, if I can't get laid for real, I might as well write about times when I could.

If you're at all interested, ask me a question. About anything. I will answer all sex questions publicly.

Let's make some interactive porn!
Sunday, December 10th, 2006
4:15 pm
Where all are the tops who will give me their piss and then fuck me senseless?

Well, they're not online. At least today.

I might have to make a trip to the Eagle tonight.
Thursday, November 30th, 2006
8:59 pm
Long-Overdue Update
It's almost been three months since I've posted. I can't believe it.

Apparently, I need more sex.

There have been some okay encounters in the past few months, but honestly, nothing much to write about. I gave a couple of blowjobs, got fucked once or twice by steady fuckbuddies, but that's pretty much it.

Until today!

I made an appointment to meet this guy at his apartment in D.C. He's black, mid-50's, goatee, well muscled with a nice belly and furry in all the right places. For some reason I haven't ever had great experiences with academics, so I wasn't prepared for the jackhammer pounding my ass gratefully received.

This man is literally a fuck-machine. He wasn't into much kissing or even talking, and he definitely wasn't interested in giving me his piss, but man could he fuck. His uncut, thick 8-incher got hard almost instantly when I sucked it into my mouth. He didn't want me to blow him for long, though; he was afraid of cumming too soon.

He had me get on my stomach and he started to finger me. Once my ass was relaxed he lubed up, put on the rubber, and entered me. It was gentle at first, but once I really opened up he PLOWED me.

This guy fucked me for two hours straight. Seriously. I'm a trooper, but it was hard to take. He tried several different positions, but the best one was me laying on my side with one leg pulled up to my stomach while he fucked me from behind. After ten minutes of that he gave me my first anal orgasm. It felt fucking incredible. He didn't stop pounding my tender ass for a second, and in another half hour my ass came again. I screamed so loud that the neighbors had to hear me.

After that, he started to slow down for the first time in two hours and let out a low groan. He blew his load while still buried inside me. I started to jack off with his cock inside my hole and shot the huge cumload that had been building up.

This dude is a keeper. The next time my ass is in need of some serious abuse and I need to be made some man's slut he's getting a call.
Friday, September 8th, 2006
10:54 am
The Married Guy shoved a buttplug up my ass this morning at about 7:30 after he finished fucking me. He didn't let me come while I sucked his dick or while he plowed my hole with his thick dick. The buttplug is still in my ass. I still haven't come, and I'm not going to for at least another half hour when this hot Bear couple is going to come over and piss on me. I hope they'll want to fuck my ass too.

Taking a day off just to be a slut is awesome.
Monday, August 28th, 2006
6:47 am
When it rains it pours.
Why is my sex life either overactive or non-existent? Anyway, it's strange, but I'm not complaining.

I had some HOT chat with a guy on here last night. He's a big, nasty fucker I've been lusting after for a long time. Too bad he lives in Canada--we'd have had great sex last night if we could. Thanks, man. You know who you are. ;-)

Literally while I was chatting with the Canadian stud, a trick text messages me. He's a married guy I haven't seen since last winter. Tricks keeping in touch? I guess this is what happens if I actually get to stay in one city for more than five days at a time. He e-mailed me earlier yesterday and said he wanted to piss in my ass. Of course I was into it.

He came over and we had a couple of beers on the couch while watching a piss porn. It got him really horny, and I was hoping he'd be able to piss through a hard-on and just shove it in me. I started sucking on his dick (nice thickness, and longer than I usually get to play with), and he gets to moaning and groaning. I don't want him to cum yet, so I stopped and took him into the bathroom. I lubed up me ass and stuck the funnel in. I got us naked and sat in front of him. I started to piss on myself and he began to piss on me. I fucking loved it. I was moaning like a whore. Before he pissed too much I got in my hands and knees so the funnel was in front of him, and he pissed in it.

Whenever I would flex my ass muscles, I could feel a gulp of his piss go inside me.

After he finished pissing inside me, I turned around and sucked on his dick some more. I loved the feeling of needing to hold in his piss while I blew him. He isn't really the dominant type, but he got into face fucking me, which was cool. I ended up cumming before him and caught it in my hand so I could eat it. Seeing me eat my own load got him off, and he blew in my mouth right away.

Getting filled with piss and cum is amazing. I just don't have words to describe how much it gets me off.

Married Guy left right after he came. I think he might get post-cum guilt. I haven't ever asked for sure if he's married or not, or if he has a partner. I just assume that the ring on his finger is a wedding ring.

I still haven't showered, and I'm not going to today.
Sunday, August 27th, 2006
3:22 pm
Friday, August 25th, 2006
9:37 am
Piss Fuck
I haven't gotten laid in about two months. The situation has gotten bad. Work's been kicking my ass, and taking me all over the country to places without any visible gay life, so I've been spending lots of quality time with porn and my left hand.

Until Tuesday night.
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Monday, June 19th, 2006
9:15 am
So I hooked up the the 6'6" hottie on Saturday morning. We'll call him S. S. is former military. The last time I saw him he was clean shaven, but he had a scratchy mustache this time. It felt good around my mouth and cock and balls and hole. He's a mountain of a man, and I loved climbing him. His cock is HUGE. It's slightly above average length, but thick as hell. It was like blowing a beer can. He didn't have any condoms left, so I didn't get fucked. Next time I'm getting fucked by it. I think it will be the thickest cock I've ever been fucked by.

It was a decent beginning for a friendship with benefits. We rolled around a lot and sucked each other off. He had no condoms, but he did have poppers, which was fun. He can eat ass with the best of him, and that huge cock is fucking amazing. His balls are huge, too.

Not any kink, really. I did like licking and sniffing his pits, but next time we'll have some piss fun maybe. He loved the fact that I shoot over my head. Heh.

I'll try to make some pics this week for y'alls viewing and wanking pleasure.
Thursday, June 15th, 2006
8:13 am
I have a hot trick planned for Saturday. He's 6'6". WOOF!
Saturday, June 3rd, 2006
9:14 pm
Solo Piss Sex
I had a date with a fuck bud for tonight, but he flaked out. He was going to piss all over me and force me to piss myself. I was all horned up for it. FUCK.

So I've been drinking beer and water all afternoon, and my bladder is almost painfully full. I've been edging myself almost to the point of cumming for two hours. Before I let myself cum, I'm going to take my 8" silicone vibrator and give my hole some attention. It will bash the fuck out of my prostate and my bladder, probably making me piss all over myself. I'll see if I can piss all the way to my mouth (and I always can), and drink as much of my salty piss as I can.

After I'm covered in piss, I'll switch to my black, 12" ass probe. It's thicker than the vibrator, and fills me up. After I pound myself some more, I'll shoot my load and eat it, thinking about that daddy bear who was going to force me to eat his.
Saturday, May 27th, 2006
8:08 am
Friday, May 26th, 2006
8:49 am
A new (long-overdue) fuck friend.
Last night I met up with a new fuck friend.

Rob is twenty years older than me. He's 47, 6'4", about 300#, balding, buzzed, goateed, inked, and has a great thick cut cock. Plus, his nipples are HUGE and perfect for chewing and sucking. The perfect Daddy fuck.

And he did fuck me. My ass is still a little sore. Heh. It's been a while since there's been anything in my ass except a dildo. We met up at his apartment, where we made out and traded blowjobs for a while. He's great at both. He started to feel up my hole and bent me over the arm of his couch so he could rim me. His tongue felt fucking incredible. He lubed me up, put on the condom, and pushed into my ass slowly. Once he was balls-deep, he started to plow me long and slow just like I needed. I was a complete whore, and was practically screaming for it. He started to fuck he harder and harder until he was slamming my ass. When I feel a guy's heavy ballsac slapping my ass it gets me HOT. At one point, he was pounding my hot ass and pinching my nipples, calling me dirty names. I was in piggy slut heaven.

He didn't last long and shot his load in my ass after about five minutes. Didn't matter to me, though. It felt fucking GREAT. After he pulled out I took the condom and ate his load. I needed to eat a man's load. He fingered me as I jacked my cock and I shot all over myself, all the way to my forehead. He licked it off and shared it with me.

After showers, we watched Battlestar Galactica.

It rocked.
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