My Walk on The Wide Side

My name is James and I've been married to the same wonderful woman for the last 30 years. Usually when making love, we share our fantasies or tell each other little secrets about our sex lives before we met. Lately she's been wanting to know if I'd ever had sex with another guy. I've avoided telling her the truth so far, I just don't know how she'd take it. I did decide to try and put my experience on paper, maybe I'll let her read it.

Growing up I was considered a late bloomer; sexually. During High School while my friends were dating and petting; I was at home fantasizing and jerking off to pictures of scantily clad woman in bathing suits. I was painfully shy. By the time I moved into my college dorm the only women's bodies I'd seen were in magazines. And only a few of the magazines showed the woman's breasts and nothing else.

The first couple of weeks at the dorm were pretty boring; class hadn't started so there wasn't much to do. I started exploring the campus and discovered the student center had pool tables. I love to play pool, so I started hanging out there. After a couple of weeks I meet this guy named Ray. He was an excellent pool player and for some reason took me under his wing and started to teach me how to improve my game.

Ray was the a-typical Yankee, obnoxious to a fault, but still likable. He reminded me of a "Hells Angel" type: big frame, muscular, mean looking. We got to be friends, but he was definitely the alpha male. Over the next 4 weeks we played, talked a lot, got to be friends and ended up joining an 8 ball tournament together. The tournament was to last for 8 weeks and we played every Friday night. After the game, we got into the habit of ordering pizza at his place and drinking a few beers. One particular Friday night changed my life forever.

We were both BSing about the game, drinking beers and snacking on pizza. He said one of friends had sent him a porno flick and wanted to know if I'd be interested in seeing it. I said sure and helped him drag out the film projector. He retrieved the film and I feed it through the projector and started it up.

The film opened showing this good looking woman sitting at a desk in an office. The intercom comes on and her boss pages her into his office. As soon as she closes his office door behind her, she starts taking off all her clothes while walking around to the back of his desk. She had an incredible body, slim waist, nice round tits and full pouty lips. She walks over to her boss who had pushed himself out from his desk. He swings his legs out and toward her. She kneels and spreads his legs so she can get close to him. She then unzips his pants and pulls out a monster cock and starts stroking it. Then she starts licking and sucking all over his cock. I'm getting so turned on I'm about to cum in my own pants. I've never seen anything like it before. My dick was leaking pre cum and I was so hard it hurt to be trapped in my jeans.

I came out of my fog long enough to vaguely here Ray say something. I turned to asked him what he said and my jaw dropped. He had his pants unzipped and pulled down, he was playing with himself; jacking off. I couldn't say anything; I just stared as his hand pumped the biggest cock I'd ever seen. Outside of gym class in high school it was the only cock I'd ever seen.

Ray saw me staring and said, "What's the matter, you never saw a man jack off before."

"No," I told him sheepishly.

He looked over at me, and said, "Maybe you could use some relief too," as he pointed to the tent in my jeans. "So you know what a circle jerk is."

My mind was swimming at this point. Ray was sitting in his chair talking to me very nonchalantly as he continued to stroke his cock. All I could get out was, "What's a circle jerk."

Ray chuckled and said, "You really don't know anything, do you. I got some buddies back home; we'd get together about once a month and jack off. We'd sit around, drink beer and stroke our cock to a film like this; that's a circle jerk. Of course, there is one variation. We had this new guy move into the neighborhood. When he found out what we were doing, he wanted to join too. We let him, on one condition; he would have to jack us all off while we watched the movie and drank beer."

I was shocked, "One guy jacked off the whole group."

"Yep, he sure did and he was good. Go ahead and whip it out, do a little jackin it'll make you feel better."

I was a little nervous but said, "ok," and started to disrobe. Just as my underwear was down around my knees I heard Ray laughing and I looked at him.

He pointed at my dick with a chuckle and said, "What's that little thing." I turned 5 shades of red. He said, "No wonder you don't know much about sex, having a little thing like that. Now look at this, this is a man's dick, this is a real man's dick," as he pointed to his own. His cock was huge, he was 7.5 to 8 inches and thick; I could barely make 5.5 inches.

In a demanding voice he said, "Remember the story I told you about circle jerks, well I've decided you're the new guy, the pivot man. Now get over here and I'll let you see what it feels like to jack off a real man's cock." I've never been ashamed and so embarrassed in my life, but my cock was hard as a rock. I tugged my pants up and walked over to his chair, he spread his legs and pointed to the floor said, "Sit."

I sat down between his legs and stared at his huge cock for a long time. He said, "Come on what are you waiting for, grab it." I was in shock, I couldn't believe I was in this situation, but I reached out and took hold of his cock. It was slightly warm to the touch and velvety soft yet it was a hard as a rock. I was mesmerized by the way my hand slid up and down as I pumped his large cock.

I heard him say, "faster," and I increased the speed of my pumping. I remembered the secretary on the film had also been massaging the guy balls, so with my other hand I reached out and cradled his balls and gently rubbed them. "Stop, I've got to go take a leak. When I tell you to, finish getting undressed and get us couple of beers, understand." He stood up, squeezing between me and the chair, dragging his cock across my face. It was wet and left a sticky smear on my check. He said, "Ok, finish up and I'll be back in a minute."

I was so humiliated but so turned on that I had already cum once without touching myself and I was getting close to a second one. I just kept thinking about his large cock in my hand over and over. After a minute I decided I better do what he said so I finished getting undressed, cleaned up the mess from my orgasm and went and got two cold beers.

When I got back Ray was sitting in his chair, naked from the waist down and had brought a black bag with him. He said, "Come here." So I walked over and handed him a beer, I put mine on the table. He reached out and tweaked my penis, "Wow, it's so small it looks like a little girl's clit." God, I was so embarrassed, I wanted to hide. "I can tell your enjoying yourself aren't you?"

"I, I don't know," was all I could get out.

"Well your little clit tells me you are very turned on," he told me flatly. "Now sit," and he pointed to the floor between his legs again. I started to object, but he got angry so I sat between his legs again. "Stroke it," he instructed, so I began again. After a few minutes a small drop of liquid formed on the tip of his cock. I was studying it intently when I heard in a very sarcastic voice, "You like stroking my cock don't you, you like a real man's cock." Then he bent over and grabbed the back of my head with both his hands as he guided my face towards his cock.

I pulled back a little and said, "Wait, what do you want."

"I want you to suck my cock with those sweet pussy lips of yours." I was stunned. I looked at my hound pumping his cock, not really sure if I wanted to do this. Finally I decided it wouldn't hurt to try. I stopped pumping his cock for just a second, and moved it to my lips. I gave the tip of his swollen cock a quick lick and wiped away the pre cum with my tongue. The pre-cum tasted slightly salty and was a little slimy in my mouth but it wasn't as bad as I thought it would be.

Ray cleared his throat as to say, get the show on the road. I moved his cock back to my mouth and gently sucked on the tip. After a few minutes, I had my eyes closed and was gently working the head of his cock with my mouth. Suddenly, I saw a bright flash. I looked up; Ray was taking my picture again with a camera he had pulled out of the black bag. He said, "Just so you don't go spreading rumors about this, now finish sucking me," as he pointed to the two developing Polaroid's.

I went back to work his cock. The taste of his pre cum becoming stronger. With one hand I was jacking him and my mouth and tongue I was making love to his cock . I tried to remember everything the girl had done on the video. After a few minutes I felt his legs close on the back of my head. My head was pinned as he started to pump his cock in and out of my mouth. Finally he shoved his cock down my throat as far as he could get it; then I felt his cock swell even larger, then suddenly he spewed into my mouth. It shocked me a first but I recovered and swallowed as much as I could. It didn't taste too bad, a little slimy with a peppery after taste. I continued to suck his cock until it was limp and completely drained. I looked up a Ray and saw he was totally drained.

I got up and picked up my underwear and I heard Ray say, "Not yet, pussy boy come here." I thought now what, so I walked back over to him and he pointed to my dick and told me I hadn't finished yet.

"Stand there and play with your clit, pussy boy, I may want to see you cum." I was so embarrassed, yet here was this man telling me to do just that and what was crazier was I was going to do it. I stood there and jacked off in front of him while he made lewd, condescending remarks about my "little" dick and me being his "cum slut whore." After a few minutes. all the nasty talk finally had its effect and I could feel my orgasm building.

He was watching me closely, then said "You about to cum, pussy boy."

"Yes, I'm very close," I breathed.

"Good, stop what your doing," he said almost laughing.

I looked up in shock and said, "Stop, now?"

"Yes, stop now. Stop jacking off," he demanded. I took my hand off my throbbing dick. "Now get dressed and go home. And don't jerk off, if you do you'll be in trouble."

On my way home my mind was spinning with what had just gone on. I had seen my first porno flick, first on screen blow job, jacked and blew my first cock and ate my first cum. What a night, it was just too much to think about right then.

Ray and I got together at school over the next couple of days like we usually do. He didn't mention anything about Friday night and neither did I. I had thought about several times since, but still hadn't made up my mind about it. It was so nasty, yet it really turned me on.

Wednesday, Ray invited my over for a few beers after pool practice. I didn't have to study so I said OK. After class I hoofed it over to Rays, he let me in and told me to get a couple of beers. He said he was working on something in the bedroom. I got the beers out of the fridge and went back into his bedroom.

When I turned the corner, my jaw must have dropped a foot. He was sitting in his easy chair completely naked with a giant hard on. After I recovered, I walked in and set the beers on the night stand and took a seat on his bed. I said, "What's going on, you don't have any clothes on."

He said, "I know, and in a few minutes you are going to turn back into my little cum slut. You are going to do whatever I say, whenever I say it and if you don't, you know what's going to happen?"

I shook my head no.

He pulled out the two photo's he'd taken of me; one was a picture of me with my tongue licking the top of his cock and the other with me stroking his cock and face directly behind it. He said, "You'll notice that only your face appears in the photos and that could be anybodies cock. So if you don't do exactly as I tell you, I'll post these on the bulletin board in the student center. Would you like that?"

I looked at the floor and shook my head no again.

"Good, now before I tell you the rules you will have to obey, you will need to get into your new uniform. Whenever you enter my house you will strip naked at the door. As my personal cock slave you are to wear no clothes. So go take all your clothes off and leave them by the front door, then come back here." I was stunned and in shock, but I went to the front door and left all my clothes in a pile then returned to the bedroom. He handed me a small leather contraption, which had a leash attached to it. He said, "Put it on," in a demanding voice. I looked at it but couldn't figure it out, so he instructed me it fit on my dick and balls. After a few minutes of struggling I finally got it on and handed him the leash.

"Your not doing to bad," he leared. "This is your uniform while your in my house." He took the leash and gave it a tug. The tug caused the cage around my cock and balls to tighten and caused me discomfort and learhed forward towards him.

"Good, very good," he said. "Now here are the rules: First, you will always be in uniform in my house. Second, you are not to cum unless I tell you can. I will know if you have. Finally, you will always do as I tell you. If I bring home friends and tell you to service them, then you do whatever it takes to please them. Those are all the rules; they are simple but must be followed to the letter. Do you understand them and understand what will happen if you don't follow them."

I shook my head yes.

"Great, now get over hear and suck my cock." I hesitated for just a second and he gave the leash a hard tug. It hurt so I moved in between his legs and dropped to my knees. I grabbed his large cock with my hand and started to stroke it. I moved my mouth over his cock head and engulfed the head with my mouth. Then I heard, "Hey, Pussy boy, no hands."

I quickly took my hands off his shaft and continue to make love to his cock with my mouth. After 10 minutes his breathing turned ragged and I felt his cock swell and he shot his load into my waiting mouth. Ray said, "Not bad, pussy boy, but you do need some practice. For the next week I want you here every day after class learning to suck my cock."

Needless to say I was hooked. When I wasn't in class or asleep I was over at Ray's with his cock in my mouth. Ray stayed at school another 9 months but eventually had to return home. We kept in touch for a few years then finally lost touch all together. I still think of him on occasion and all the fun we had together.