Enjoying Life's Guilty Pleasures

"I almost always play safe. Most of the guys that I have sex with wear condoms. I insist on staying clean and safe. But, I have let a few men cum inside me without a condom... all of whom I knew. They were older and married. I had a regular friend for about six months who would come to my place and I'd either suck him or he'd fuck me. He was in his late 40s, married and, except for the time he was with me, was straight. He used to tell his wife he was golfing or fishing, then he'd come over and we'd have some play time. He always told me I had a nicer ass than his wife. He was also very well endowed - about eight inches hard. He said his wife could never take him that way - that it hurt too much."

"Damn, Eight inches, huh? That's pretty big! I'm just curious, what's the biggest cock you've ever taken?"

"I'd have to say the biggest was about 10 inches. I met this guy on Craigslist one time. It was one of the first nights I'd ever posted an ad and I was horny as hell and I'd had a little too much to drink. My post said something like, "Smooth, bubble-butt virgin bottom looking for the right big cock to take my cherry," or something like that. I also posted a couple pics of my ass and one of my cock. The next thing I knew, I was getting about 5 or 6 responses a minute. I couldn't even keep up. There were a lot of guys who sent me dick pics, but one in particular caught my eye. He was kind of a short stocky guy, but he was hung like a horse. He said he was married and in town on business. I thought, shit, if I'm going to get fucked tonight, he's the one... so I emailed him my phone number. He called right away. We chatted for a couple of minutes and, then, before I knew it, he was at my front door. He had me on the floor my hands and knees in no time. He was huge! I sucked his cock until he got really hard, then he rolled on a condom. A few squirts of lube later, he was buried balls deep in my ass - and he wasn't very gentle about it either."

"Fuck," John said. "Sounds painful. So, what did you do?"

"You know, I remember trying to push him off, but that just made him go at me harder. He started calling me bitch and telling me to shut the fuck up - that I needed a hard dick in my ass and to enjoy it... you know shit like that. It must have been on his second or third thrust that I felt a terrible pain in my stomach - like someone had just shoved a telephone pole up my ass and it was about to come out my mouth. Later, I did some research. I'll spare you the gory details. Suffice to say, he ripped me a new one. To top it all off, he broke through the condom and finished inside me. I was scared to death. Thankfully he was clean. From then on, I vowed to not let anyone fuck me if there if they were bigger than 8 inches."

The entire time I was talking, I couldn't help but notice that John was getting hard again. "I can see all of this talking about fucking has made an impression," I said jokingly.

John looked down at his revived cock. "Yeah, I guess so," he said.

"I've got some condoms and lube if you're interested? Or I could suck you some more..."

John glanced at his watch. "Well, I really should be going, but ok."

"Ok what?" I asked.

"Why don't you suck me some more and we'll see," he said.

"That definitely works for me," I said as I slid back down in front of him dove face first onto his cock.

I must have been sucking him for a good five minutes or so when he tapped my on the back of the head. When I raised up, he motioned for me to get on the bed. I stood up, pulled my shorts off and reached into the nightstand drawer and pulled out a condom and the bottle of lube.

"Go ahead and put this on," I said as I crawled on top of the bed on my knees. I squirted some lube along my butt crack and into my ass. With my exposed ass and ankles hanging over the edge of the bed, John walked up behind me.

"Wow, you really do have a nice looking ass," he said. "Don't take this wrong, but you could have been a woman with that ass. No wonder guys like fucking you so much." The next thing I felt was the head of John's cock as he rubbed it up and down my crack. Using his left hand to get me adjusted to the right height, he held his cock in his right hand and began pushing into me. A split second later, he was balls deep inside me and grabbing my hips. I couldn't help but groan in ecstasy as he began fucking my upturned ass.

"Fuck you're tight," he said. "Damn that feels good." He picked up the tempo of his thrusts as he spoke. I reached down between my legs and began to stroke my cock.

As John picked up his pace, I began to stroke myself harder. After only a few minutes, I felt my orgasm build to that point of no return. At almost the same time I began spewing my seed onto the sheets, I felt John raise up on his tip-toes and push into me hard. His second orgasm had arrived. With his cock still firmly planted in my ass, he leaned over me. I could feel his heartbeat on my back through both of our shirts.

"Fuck," he said breathlessly. "That was fucking unbelievable!"

I reached back and felt his softening cock. I squeezed it gently, holding him at the base. He stood up and began to pull out of me. His slippery cock slid easily out of both me and the condom. Without saying a word, I turned around on my stomach and took him back into my mouth. He fucked my mouth for a couple of minutes and finally collapsed backward into the chair. I slowly pulled the load-filled condom out of my ass laid it on top of the bed beside me.

"Fuck, that was nice," I said, as I rolled around and placed my feet on the floor beside the bed.

"You're not kidding," he said. "I never in a million years would have thought I would have done something like that."

"And just think, you didn't even have to buy me dinner or take me to the movies," I laughed.

John stood and began to get dressed. "You know, I might not ever do anything like this again, but I can tell you that I'll never forget it."

"That's cool," I said. "I'm glad you enjoyed it."

"Do me one big favor, though. Whatever you do, don't tell anyone about what happened here tonight. That would get me fired and I'd probably be blackballed at every hotel and bar in this state if not the country," John said.

"No worries. I never say anything to anyone. I have a reputation to protect too. I'm always discrete. I will be here for the next week though, so I'm sure I'll see you around. Just give me a call if you change your mind and want to get together again."

"Ok, I'll keep that in mind," he said.

I really didn't expect to get together again with John - at least not on that trip. You can imagine my surprise, however, when he called me two days later for an encore. After all, he said, I shouldn't be the only one to enjoy a little guilty pleasure every now and then.