Size Queen

My first gay sex experiences were all oral, meeting a guy, and sucking each other off. Most of the time, I and my partner would get naked, and make out for a while before getting down to business and sucking cocks. It was always fun, but I had an urge to go farther, and find out what it was like to take a cock in my ass. I had topped a couple of guys, at their request, and liked it, but I had a feeling I was more of a bottom. When I watched porn, I'd focus on the guy getting fucked, wondering if it felt as good as the actors made it seem. Scenes of big thick cocks pumping into a willing ass made me hard, and I also wondered if I could handle a cock that size. The idea to get a dildo came to me, and I watched a few video clips online of guys doing themselves. It looked like fun, so I did some browsing, and located one that seemed right. 6 inches long, moderate thickness, and a slender head 'to aid insertion'. I laughed at that line, and ordered it, and some lube. A few days later it arrived, in an innocuous box, just as the site had promised.

I immediately stripped, and went to the bathroom. It had a suction base, so I stuck it to the door, slicked it up with lube, and smeared it around my asshole. Then I got on hands and knees, and backed up to the door. I had to reposition the dildo, and tried again, this time it bumped against my puckered ring, in just the right spot. Taking a deep breath, I pushed back. At first, nothing happened. I could feel the head pressing against my hole, but it refused to open. Perplexed, I stood up, and applied some more lube, trying to poke some inside. My finger slipped in after a bit of pushing, it was an unusual sensation. Then I got back on the floor and tried again, making an effort to relax. Again, my hole stayed closed, but I kept pushing back, and it popped through. Immediately, my asshole felt like it was on fire, and I quickly moved forward to pull it out. The intense burning stopped, leaving just a dull ache. Wow, that wasn't fun. My hole felt weird, so I clenched my ass muscles a few times, and it felt better.

I wiped myself clean, and started browsing for any information. There was more than I expected, and I spent an hour reading. Two things were common, I found. One was to push out, like taking a dump. This would open up the hole some, and make it easier for the dildo, or a cock, to get in. The other was that pain was common at first, but would get better each time one's ass was penetrated. If pain was bad at first, then take it out, relax, and put it back in. Armed with knowledge, I was ready to try again. With dildo on the door, and it and my ass well-lubed, i got into position and pushed back. This time, I pushed out with my ass muscles as the head touched my ring, and it went in much easier. It was still painful, so I pulled it out, and rubbed my hole with a finger. Trying yet again, it slid in without any drama, and I was pleased that pain was indeed much less.

I experimented with it a lot, and found that each time was easier than the time before. My hole was getting stretched out, and I was able to enjoy the sensations. Either kneeling or squatting, I could work it in and out, just like getting fucked. I also discovered that jacking off with the dildo in me made orgasms more intense. By now, my desire to take a real cock was very strong, so I made the decision to go ahead, and try it. I was nervous, of course, it would be with a stranger, since my oral sex partners were either bottoms, or did oral only, so I would have to be as careful as I could. Browsing the hookup sites brought up a lot of profiles for tops, and right away I saw that many were very aggressive. I wanted no part of that. There a few that were more to my liking, and one in particular caught my eye. He lived in a nearby town, was close to my height and weight, and his profile had a friendly air to it. He also stated his cock length at seven and half inches. I sent a message, asking if he wanted to chat, and saying i liked his profile. Surprisingly, he answered right away.

We chatted, sending messages back and forth at first, then went to texting. he seemed to be a real nice guy. As he put it, sex was supposed to be fun. He didn't go for trying to dominate a guy, he said. Then he popped the question.

"Want to meet?" his text read. There it was, time to make a decision. I hesitated, then hurriedly replied that I did want to meet. Since he lived alone, and I had roommates, we agreed to meet at his place in an hour. I took a shower, taking extra care with my cock and asshole, even sticking a finger inside to make sure I was clean. Then I drove the twelve miles to the town where he lived, and followed the GPS to his apartment building. He opened the door to his ground floor apartment, let me in, and led me to the bedroom. One inside, we undressed and got in his bed, and started kissing and fondling. His cock got hard fast, and I could tell it was a little thicker than my dildo. That was followed by some 69 action, side by side, eagerly sucking on each other's hard cocks.

He stopped, and turned around so he was facing me again.

"Can I fuck you?" he asked in a soft voice, followed by a kiss. I was very turned on, and definitely ready to do this.

"Yes, how do you want me?" He thought for a second, then suggested he get behind me, and take me that way. I agreed, and lay still as he climbed over me, and got lube from the drawer. He spread the gel between my cheeks, and pushed some into my channel with his finger. Then He lay down behind me, and had me lift my leg. When I did, he wiggled closer, and I could feel his cock probing between my ass cheeks. Then he found my hole, and started to push. I relaxed, and pushed out, and felt his cockhead enter me. It was bigger than I was used to, and I felt a little burn, but bit my lip and let him keep going. He took his time, didn't shove it in all at once, just gave it to me a little at a time. When he bottomed out, I felt a sharp pain deep inside, which quickly subsided. He'd felt me jerk, and waited a few seconds, then started to fuck me with shallow strokes. It began to feel good, I liked how his body felt up against mine, his arm around my waist and his hand holding my cock.

Just as I was getting into it, I felt him tense up, and he gripped me tighter. He gave a soft sigh, and I realized he was cumming. After he'd finished, he pumped my cock with rapid strokes, and soon I was shooting my load onto his sheets. We lay there for a short time, until his cock slipped out of me, then he got up and went to the bathroom. He came back out, and said I should clean up too. I stood up, and felt something coming out of my asshole. Sure enough, when I wiped back there, the tissue had cum on it. He hadn't used a condom. We made small talk while I got dressed, he had to shower and go into work, he said. We hugged each other at the door, kissed, and I left. Driving home, I became uneasy, getting fucked bare hadn't been in our conversation. It hadn't been discussed at all, which was my fault. I sent him a text, telling him my concerns, and he replied that he was clean. He had been tested twice after breaking up with his boyfriend, and said I had been the first guy he'd been with since the last test.

The whole episode freaked me out, and I didn't contact him for a while. When I did, he said he was sorry, that he was getting back with his ex. He did reassure me that he was clean, and that I should not worry. Right after that, I got very busy at work, with a lot of overtime, so I had no time for anything except playing with my dildo once in a while. That finally slowed down, and I had time to think about finding a guy to have some fun with. The websites had a lot of the same guys, but there were some new profiles, and I was surprised to see one in the small town where I lived. He was a younger man, 33 to my 45. What caught my eye was a picture of his cock, eight inches with a big knob of a head on it. With nothing to lose, I sent him a message.

He responded that evening, and we exchanged several messages. He was bi, and married, but could get away for an hour or so. His answer to my question about safe sex was that he was recently out of the military, where he had been regularly tested. He hadn't been with a man since, had gotten married, but was feeling the urges again. When he asked what I waned to do, I played it safe, and replied that we could start off with making out and oral sex, and go from there. Sounds good, her replied, and waned to know if he could come to my place. My roommates were gone, it was dark, so I told him yes. A half hour later he was in my apartment. he was taller than I thought, at almost six feet, but slender. He had a kind face, and chatted in a friendly way as we undressed. Once we were naked, we looked at each other for a moment. He had soft light brown curls on his chest, with a trail leading down his belly. At his crotch, it spread out into a generous bush surrounding his semi hard cock.

We came together and embraced. Wow, he was a good kisser, no hurry at all, letting it stretch out as we held each other and let our tongues swirl around. When we came up for air, he motioned towards the bed, and we climbed in and started kissing again. His hand slid down the front of my body, and took hold of my cock, caressing it and squeezing the head. I grabbed his, and marveled at how thick the head was compared to his shaft. Unlike my first time, I was eager to have this guy in me. I knew what to do, and was excited about taking a bigger one. We got into a 69, and I got to see it close up. The rim on the head was very pronounced, and must have been very sensitive too, he jerked when I slid my tongue under the edge. It was a mouthful, too, but I took it in, and gave it a good and wet sucking. He was doing a good job on my cock too, good enough I could feel the familiar pleasant buzz inside me. He came up for air at the same time as me, and we looked at each other.

"You want to fuck me?" I asked, hopefully. He turned around, and knelt beside me on the bed.

"Sure. You have lube?" I pointed at the nightstand, at the white tube. He squirted some on his cock, and handed it to me, so I could do the same to my asshole. His cock looked amazing, standing straight up, shining from the coating of lube.

"How do you want it?" It struck me that he didn't have on a condom, but I was too worked up to stop now. I was already on my back, so I pulled my legs back and spread them wide. He moved around into position, levered his cock down to point the head at my hole, and leaned forward. When he did, the fat head pressed against my ring, and slowly forced its way past. It hurt, but I kept quiet, and when the head got past it felt better. Whew. He leaned forward and put his hands on either side of my chest, while I let go of my legs, and let my heels rest on his lower back. Tied together in that position, he pushed it the rest of the way. When he was most of the way in, I felt an odd tingle, and felt it again when he pulled back. I didn't know it, but the big head on his cock was giving my prostate a good rub on each pass.

It felt amazing, a sensation I'd never experienced before, but his longer cock and the girth of the head was making it happen. He kept up a steady pace, and pretty soon had me wriggling under him, arching my back with pleasure. My cock was pressed between our bodies, subjected to a lot of nice rubbing, rolling, and friction too, and the combination of that, and prostate stimulation, was too much. I felt the cum rising, then it was spurting out onto my belly, a big load, more than I'd ever shot before. My partner picked up his pace, and soon he was buried in me, shooting hot cum inside. Once he was emptied, he pulled out, wiped off his cock, and started to get dressed. He needed to go before his wife got suspicious. I asked when he could meet again, and he shrugged.

"Never know, man. Tonight it worked out. Keep in touch, we'll see." With that, he left.

Once again, I had let a guy take me without a condom. With some worry, I bought a couple of test kits, and tested myself a week later, and again after a month. Both were negative, a big relief, and I resolved to be more careful. I tried to set up another meeting with the last guy, but we couldn't meet at his place, and I was rarely home alone. After a while I gave up, and started looking elsewhere. I saw mention of a site called Craigslist, and took a look. This was when the Personals section was in full swing, and I was amazed at the number of posts. Most weren't too informative, so I made one of my own, stating I was looking for a top, and he had to have at least eight inches, and more was better. An hour later, I checked my mail, and it was full of responses. Unfortunately, most didn't make the cut, being fake, too small, too fat, etc. A few were promising, so after deleting the duds, I read through them more closely. Once guy, Brian, really caught my eye. He was a bit taller than me, but had a slender build, a real nice body that tapered from his shoulders down to his hips.

He wasn't bashful, his message said 'Hi, I'm a top, I'm hung, let me know what you think'. His pictures backed up his claim, the full body shot displayed a long and thick cock hanging down from his crotch. Another showed it fully erect, with a prominent vein on the top. The head wasn't a big dog knot like the other guy had, just nicely shaped, somewhat pointed, with a prominent rim. He lived a half hour away, so I decided to be bold, and send some pictures that not only showed my body, but also my face. I also asked him about safe sex, wanting to get that out there at the beginning. Shortly, I had a response, with more pictures. He was a good looking guy, kind face, short graying hair, and clean shaven. Another was a full body pose, including his face, and his cock fully erect. The caption read '8.5 Inches'. He said I was good looking too, and would like to meet me. Also, if I wanted him to use a condom, he would. He said he preferred to go bare, but only if he and his partner were exclusive. Reading further, he had been in a long term relationship with a man, living together for 10 years until his partner developed cancer, and died 6 months ago. He hadn't been with anyone else in that time.

All in all, it sounded very promising, and I sent back that I'd like to get together. He said he could host, and we made plans for me to come to his home the following evening. That night, I fantasized about how his cock would feel as he fucked me. The next day at work seemed to last forever, but quitting time finally arrived. I had a light meal and watched porn for a while, then took a shower, taking care to get myself clean as possible. When I arrive at his home, it was in a nice suburban neighborhood. He opened the door, dressed in a pair of plaid boxers, looking just like his pictures. Once inside, he offered me a drink, and we sat on his couch to get acquainted. Brian had a very calm personality that put me at ease right away, and we chatted about a variety of things for almost an hour. He was curious about how I came to be attracted to men, and we discovered our past experiences were very similar, with the notable exceptions that he was a top, and was had been out for many years. He understood my need to stay discrete, and didn't judge me.

Once our second round of drinks were finished, he took the glasses to the kitchen. I was leaning back on the couch when he returned, and I was pleasantly surprised that he had removed his shorts. He stood next to the couch, his cock slowly rising.

Sitting up, I leaned forward to put my hands on his hips, and pull him to me, taking the end of his cock in my mouth. Brian liked what I was doing for him, moaning softly as my head bobbed up and down on his shaft. It got harder, and thicker as I worked on him, and my own cock was straining uncomfortably inside my jeans. Reluctantly, I released his beautiful piece, and stood up to undress. When I was naked, I embraced Brian, and we kissed. I love kissing a man, especially one who is clean shaven. He was a great kisser, soft, yet manly and in control. Taking my hand, he led me to his bedroom. Like the rest of the house, it was simple but tasteful, with a king bed. We lay down, and resumed making out.

I was on my back, Brian stretched out next to me, playing with my nipples while slowly rolling his tongue around mine. I felt for his cock, finding it laying on my leg, and took hold of it. The girth was impressive, but I was confident I could take it, having bought a bigger dildo and gotten used to it. I ran my thumb across the pointed tip, making him groan into my mouth. He broke the kiss, and moved down to take my cock in his mouth, giving me a wonderful blow job. I was at the verge of cumming, and he stopped.

"Do you have a favorite position?" he asked.

"I've only done it on my side, and on my back." I replied. "On my back was fun." He reached over to the nightstand, and opened the drawer.

"Let's have you try something new, then we can finish with you on your back." As he said this, he brought out some lube, and a condom.

"You want me to use a condom, right?" He was sitting up on his knees, looking at me, his cock pointing at the ceiling.

"Mmm, I don't know. What do you think?" He shrugged, and smiled at me.

"Well, I'm clean, got tested after my boyfriend passed. But I'll put it on." I looked at his proud cock, and imagined it deep in me, filling me with cum. I wanted this to be good for him too, and made a decision.

"No, we're good, you can do me bare." He nodded, and tossed the condom back in the drawer.

"Okay, get up on your hands and knees." I did so, and felt him squirt the cool lube above my asshole, letting it run down. With a finger, he spread it around, squirted out some more, and this time worked it inside me. I could hear him putting it on his cock, then shuffle between my legs. With one hand on my back, he put the head against my ass ring, and gave a long slow shove. After a moment of resistance, it entered easily. He sat still, letting me adjust, then gave me more. As the thicker shaft pushed in, I had a bit of pain from being stretched, but I rode it out, knowing it would go away, and it did. He kept up the steady pressure, going deeper and deeper, until I felt his skin press against mine. When I'd watched enough porn, I had seen guys getting pounded in this position, a position of submission. But Brian wasn't that way, instead, he would draw almost the entire length out, then push it back in. He was touching my prostate, but in this position it wasn't as intense, more of a warm glow inside me, and very pleasant. I felt filled up, and wondered if Brian wold go ahead and finish in me this way. If he did, I wouldn't mind.

But, he stayed with his plan, and after a few minutes of long stroking me, he pulled out and had me get on my back, then had me move my ass to the edge of the bed. He got on the floor, and pulled my legs up against his chest, and pushed his cock back into me. Once in position, he started fucking me against, this time faster, but not rough at all. Now his cock was hitting my prostate harder as it went in, and the sensations ramped up immediately. My cock was bouncing up and down in time with his strokes, and I saw continuous string of precum drooling out onto my belly. Without any help from my hand, I felt an orgasm building, slowly but surely, and watched as cum began to roll out. It wasn't in powerful spurts like when I'd jack off, this was more of a flow, and the intense tingle didn't peak and subside, it hit a level and stayed. It was the most amazing orgasm I'd ever experienced.

Brian kept up his pace, and I could tell from is face he was getting close. Sweat was running down his face, and he gripped my legs tighter. I wanted to help him, but I was pinned to the bed, totally in his control. But soon, he hit his peak, and drove it in to the hilt, holding it in place as he bred me. When he pulled out, I could feel his cum dribbling out of my gaping ass. We cleaned up, and had another drink. When he offered to let me stay the night, I readily accepted, and we slept with our arms around each other. In the morning, he took me again, laying on me with arms around each other, entwined as he came in me again. We got together several more times over the next month, and the sex was always great. Brian was a skilled and considerate over, and I would have been happy to see him and no one else. But after a while, her became more insistent that I come out, and that issue came between us. He finally gave me an ultimatum, and that was the end.