Peoria, Illinois

Dildos were not something I was ever interested in. Or so I thought.

Last summer I hooked up with a guy online one Friday night. His profile was pretty vanilla like mine. I went to his place.

He was versatile and we took turns fucking each other. I get off on getting fucked by a guy I just fucked. It is something about that extra intimacy. Also, after I shoot I get soft. As soon as there is a dick up my ass I get hard and can cum again pretty quick. Much faster than if I fuck again.

Anyway, this guy was fun. Had a medium-sized dick that he knew how to use. Big dicks are not always the most fun for me. They hurt too much sometimes. Give me a nice 6-incher that can last and I am happy.

So, we were done fucking and just lying in his bed talking, playing with each other's balls and cocks.

“Glad you came over,” he said. “Want to do it again sometime?”

“Sure,” I said and meant it.

“Want to try something different?” he asked.

“Like what?”

“Ever play with toys?”

“No,” I answered, feeling a little turned off. It wasn't my thing. I don't care what others do, but it wasn't for me. “Never have.” I wasn't sure why I didn't want to go there, but I didn't.

“It'd be hot if you want to try,” he said pulling on my dick.

“I don't think so,” I said. “It is not my thing.”

“OK,” he said. “That is cool.”

He started making out with me, kissing my neck and face. It felt good and I started getting hard. He was lying on top of me rubbing his hard cock against mine. He rolled me over and I stuck my ass up in the air, legs spread, assuming the position with hands pressing against the bed.

Roger rubbed against me from behind, fingering my hole tenderly.

“Beautiful hole, beautiful ass, beautiful man,” he whispered in my ear. I ground back into him, anticipating his cock, eager to have it inside me. I closed my eyes.

“Hold on,” he said. “Let me get a rubber.”

He reached under the bed. His fingers were then applying some lube to my hole. He rotated his finger around, causing me to squirm. I wanted that cock.

I felt the head of it enter me. I tightened around it. It came in a bit more. Something felt odd. Not bad but odd. Different. I looked back and saw Roger's dick jutting up from his belly. It was then I realized he had put a dildo in me.

“What the fuck,” I grunted.

“What are you doing?”

“Relax,” he said while he kept the dildo in me. “Let me show you something new.” He moved it in further.

It did feel good, so I let him continue. I could feel the end of it – the balls that stopped it from going all the way in. He fucked me slowly all the while kissing my ears and neck.

“Roll over on your back,” he instructed. I did.

He kept one hand on the dildo to keep it in my ass and began sucking my cock. It felt good and I relaxed into it. Maybe toys were not so bad.

“Ready?” he asked looking into my eyes.

“For what?”

Suddenly there was a light humming noise and the entire inside of my ass was vibrating. Shivers ran all long from my tailbone to the top of my head. Roger kept sucking me harder and harder.

It was crazy. All the sensations – the vibrations, the in and out of the dildo, Roger's expert mouth on my dick. I came with a roar, causing him to choke and lose his grip on the dildo. It flew out of my ass like a buzzing rocket. We both laughed.

“OK,” I said, “I learned something new tonight.”

“Glad you liked it,” he said, rolling on his back and lifting his legs up. “Stick it in me.”

I picked it up and looked at it for a second or two before applying some more lube. Roger's asshole gladly opened up to receive it. I fucked him slowly while giving him head. He shot a warm load in my mouth. I ended staying the night and we went dildo shopping the next day. Sounds like a twisted Doris Day ending but it is what happened.

Clarence

Cleveland, Ohio

I was frightened. Arrested for just a gram of cocaine. I had never been to a jail. While sitting there waiting for I did not know what, I could hear strange noises and people crying and yelling obscenities from inside. The smell was really bad, like an old urinal or something. Around me were other scared looking faces and a couple that looked as if they had been through a war. My knees shook and I could not hide my fear of this horrible place.

After some paper work and a very unpleasant strip search I was placed in a cell with four other men. I could feel them staring at me as if I was fresh meat. Their eyes pierced my body like big sharp lawn darts. I had the sensation that I was in well over my head. The bad news was that I was going to be there for a while. As the cell door was locked behind me I just stood against one of the walls, trying not to be noticed.

My cellmates left me alone for the first 20 minutes and then two of the guys came up to me and finally spoke. After some small talk they asked me if I wanted to sit down. I sat and began to feel a little better with my new “roommates.” We all talked about why we were there and how hot it was in the cell. The four of them removed their shirts. I naturally followed suit and removed my own, not thinking anything of this. I used my shirt to wipe the perspiration off my face and upper body. The others were staring at me. I was aware of the sexual tension growing in the stale air of the cell. I was both excited and worried.

Three of us were sitting on the bench. My excitement won out over my worry. The guys weren't bad looking, just a bit hardened. Ben, the oldest and biggest of the bunch, reached over and just placed his massive hand on my cock. I was so startled, I pulled back quickly and my shoulders met with the bare back of one of the guys. I had an instant erection and my sex drive got the best of me. I was only 19 after all. I stood up and stripped my pants off. All four of them began placing their hands on me and roughly pulling on my flesh. My cock was so swollen and in need of relief I started stroking it through my underpants. They all watched with pleasure and began rubbing down their own meat. The self-masturbation continued for a few minutes in total silence.

My underpants were yanked down and the guys all stripped quickly. They began pulling and stroking each other wildly. I got on my back on the bench. They all took turns sucking on my cock. I squirted all over two of them and turned over. With my ass spread wide open they used my cum to lube me up and then all four took turns fucking me. Plunge after plunge, pump after pump, they filled my hole with cock and took turns cumming inside me.

That night our cell sex party continued with each one of us taking turns as the bottom. By morning I was so exhausted I slept half way through the day. The guards had to shake me awake when they came to take me to the judge.

Standing there in shackles before the judge, I couldn't stop shaking. I'm not sure if it was from the thought of being told I might have to stay in jail or if it was just from the exhaustion in my legs. Apparently the judge got his own ideas and took pity on me.

By the end of the afternoon I was back on the street.

The weirdest thing was I almost regretted getting out because my 24 hours in jail had been the hottest 24-hour sex party ever.

Steve

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