The following is a true story about my first sexual experience with a man. It happened almost two years ago, but should have happened long before. The long before is about 10 years ago when we were both in our mid 20s and single.
Todd Took Me
I worked with Todd and we also spent a lot of time together socially with a large group at happy hours, parties, etc., the kind of things singles in their 20s do. And we became good friends. Although I was able to find girls to bed every now and then, I masturbated a lot more than I would have liked. Hell, I still masturbate a lot. Todd always seemed to be moving from one woman to another, and I would other try to figure out why he was able to get so many more women than I when we seemed to be so similar physically and in personality. Now I realize he was just more aggressive.
It wasn't until after he and I had both moved away, and I learned so much from the internet, that I began to wonder if some of the strange things Todd would do or say around me were actually passes being made at me. There were a couple of times when he had grabbed my crotch through my clothes and although I thought it was strange, it was always when we were horsing around and it did not seem that out of place as a way to surprise me. There were always other people around. Or the times when it was just he and I and he would complain that he needed to get laid. I usually replied with something about not feeling sorry for him, I was getting a lot less than he was at any point in time. Then he became engaged and had on occasion said he was going to live vicariously through my sex life. Good luck. One time that stands out most in my mind was an occasion when he stopped by my place the day after a particular late happy hour to see how things had gone. Well I had nothing to report because, as my record had been going, the girl with whom had been very responsive all night in the end "did not want to rush into anything". Bitch! Me talking about this led us to talk about other women in our pasts in a not so favorable light. Now although he always seemed to adjust himself more than most guys, I still vividly remember him lying on my sofa almost rubbing himself and cupping his balls through his shorts. Naive me just assumed he was not wearing underwear and was trying to keep it comfortable. Now there were several other ways Todd would act that I now know were more signs of his attempts to bed me. But it would have to wait several years.
This brings us to two years ago. By now we were both married and living in different states from each other and from where we had originally met. We had kept in touch Christmas cards and emails. Also by now, I had been surfing the internet and had seen a whole new world and had developed a curiosity about guys getting off with each other. I still had not necessarily put myself in the action mentally, but the curiosity was more toward watching guys. Well all of that kind of changed when through our emails, we realized we were going to be attending the same business conference in Kansas City the next month. Now I was 35 by now and he was 33, and both husbands and fathers with responsibilities, but I began to think back of those times I had wondered about Todd's actions. At any rate, we were still friends, and I did not want to jeopardize that by making wrong assumptions. Besides, he had offered to let me stay in his room at the conference since his company was picking up his tab and I had started my own business so would be paying my own way. I did not look at this offer as a move in any way. Boy was I wrong...
Todd had arrived at the conference ahead of me and had already checked in. I found him, put my things in our room and we proceeded to spend the day at the conference activities like any other attendees. We went to dinner and talked about old times, updating each other on others from our past, and talking about our families, the usual stuff for old friends getting together. After dinner, we stopped by a bar and spent several hours putting beers away, watching sports on TV, and the usually conversion. By the time we left we were both feeling the affects. We were walking by an adult bookstore about a block from the hotel when he grabbed me and pulled me toward the door. I never had the nerve to go in an adult bookstore back home, much less with someone I knew, so this seemed a little strange but exciting. We each looked around at magazines and videos for several minutes and I found him in the back looking at the selections for the private peeps.
"Come on, my treat", he said and headed down this all. As usual, this seemed a little strange, but I followed him into a booth. It was not very big, but we stood there, he put in a couple of dollars and he began to flip through the channels. Now I had watched porn with guys, but this was much different. That was always straight sex porn, and we were seeing all kinds of action on the screen. Todd stopped on about all of the channels to see the action, but seemed to pause a little longer on the guy/guy or guy/bi action. I had a boner by now from all of these images when Todd hit my arm and pointed down the wall at some fingers poking through the wall to a gloryhole. "I think someone wants to suck you off", he said as he grabbed my erection and squeezed. I did not know what to say at this point, but since I did not pull away, he broke the ice by adding that if I wanted it, he wanted to be the one to do it. Still I did not pull away at all so next he pressed his crotch up against my thigh so that I could feel his hard cock. He then began to rub my cock and cup my balls through my jeans. I reached up and put my hand on his crotch just as the time ran out.
"More money or the hotel?", Todd asked.
"The hotel", I said and we began to walk out of there the best we could, each sporting our hard pricks.
Once on the street, he said he had wanted this a long time ago, but did not think I was into it. So I told him I had never done anything with a guy so it would be all new to me. He must have heard the nervousness in my voice so he said he was going to go back and rent a movie and for me to go get some beer and meet him back in the room. So I went around the corner and bought a twelve pack and he met me waiting for the elevator. As we got on the elevator, he again grabbed my cock and rubbed it so slightly just enough to tease it back to attention.
As soon as we closed the door, Todd dropped to his knees and started tugging at my jeans and pulled them down along with my briefs freeing my seven inches to stare him in the face. I could not believe how hot I was to have this long time friend kneeling before me ready to blow me. It was just moments before he had most of my cock in his mouth and groping at my balls. About a minute of this was all I could take before I got weak in the knees, so we moved toward the bed, we shed my clothes, and I sat down on the bed. I watched Todd stripped down to his boxer briefs and saw that he and I were still very similar in build. I was just over 6' while he was just under 6', but we both had a slim but muscular build and bodies that would be considered smooth and toned. At this point, he moved toward me and stood in front of me with a nice outline of his hard cock trying to break free over the top of his waistband. Not needing prompting, I reached up and pulled his boxers down allowing his dick to spring free. Now this was the first time I have seen a hard cock, other than my own, in person and I just sat there staring at it not knowing what do next. So he pushed me over on the bed, stepped out of his boxers and proceeded to lay down on top of me and began grinding his cock into mine. This was an incredible feeling as I started to hump back in attempt to get my cock moving on anything at this point. Todd saw my need and began moving back down to my cock, stopping to each of my nipples on the way down just to drive me crazy. Finally he got back to the head of my cock and started the blowjob again that I needed so badly by now. With a couple of quick bobs on my manhood, I was soon being deep throated and began fucking his face in the best blowjob of my life. I swear it was only a minute before I gave the obligatory "I'm cumming", but he did seem to care but instead picked up his pace. I could not take it any longer and I shot my first load of man sex cum into his mouth. It felt like I was pumping stream after stream into a bottomless pit as he just kept sucking every drop of cum out of me until I collapsed. I had just had the best blowjob of my life and it was from a man. He even swallowed my load which none of the chicks in my life had ever done. What had I been missing?
He started laughing and rolled off me and said he had wanted to do that to me from the time he had met me but never thought it would happen. Small talk at this point brought out that he had quite a few bisexual experiences in high school and college but only a few the years right after college and he had not done anything with a guy since he met his wife. But knowing he was going to be around me brought up all the desires he once had around me before. We both lay there naked, I soft at this point, but he was still half hard because of the talk and the need to cum. He began stroking himself and asked if he was going to have to get himself off now or if I would like to help him out. After the blowjob of my life, how could I say no to him, so I said I would try. Again seeing my nervousness, he got up, put the movie he rented in the VCR, pushed play, popped open a couple of beers, and turned off the lights. I watched him move around the room and was admiring his body, knowing I could do this. The movie started and he had gotten a bi video, I knew this would not take long as I quickly had downed my beer before the first scene even started.
Soon the first scene was underway and it was a guy/girl scene. We were lying side by side on the bed at this point watching the girl giving a guy head. Todd's cock was hard and was pointing straight up his body. I was getting hard again watching the porn and looking at his erection. About this time on the video, the guy had switched to eating the girl out and another guy, his roommate, was walking in the front door of the place. He said something and quickly stripped his shorts and tank top and joined the action by giving the girl his limp dick to suck. She was getting him hard and the guy stopped licking her pussy and moved up to fuck it. Now it was the normal two guy fucking a girl scene of all porns, but here I was lying naked with another guy and we were now both slowly stroking our own cocks.
Then the scene changed. The guy doing the fucking got on his back and the girl moved on top to ride him. The third guy was now standing to the side stroking himself while the girl was beginning the fuck. Then the guy being fucked reached out and started stroking his roommates cock for him. Well, a queue is a queue, so I made my move and reached over for Todd's dick and wrapped my hand around it. I began pumping as if it were my own. This was a most intense feeling of stroking another guys cock. Now I said we were about the same size, but his cock was probably only 6 inches to my 7, but about the same thickness. The hardness and heat of his cock in my hand was amazingly different from the years of feeling my own. My fingers were getting wet from precum and I was wrapped up in stroking when Todd tapped me and pointed to the screen. Now the guy had moved in to let his roommate suck his cock while the chick was fucking him. It was now or never, so I moved into position and held his cock up with my face inches from his big purple head. I opened my mouth and put the head of his cock in my mouth. Giving my first blowjob came amazingly natural to me as what to do as I began sucking and licking up and down his shaft. I moved my tongue around the head and tasted his precum. I could not get him all the way in with my gag reflex, but by using my hand and sucking, I felt I was doing alright and it sounded like he was enjoying it too because he was starting to talk dirty. He was calling me a cocksucker and telling me to suck his big hard cock. I was paying no attention to the TV by now but only focusing on sucking cock. At some point, he had reached out and was holding and stroking my cock as we moved closer to a 69 position. I moved from suck his cock to licking down the shaft, to licking and sucking his balls, and back up to suck his cock. By now I was really getting into it and Todd had began playing with my ass and trying to finger my hole. As soon as he got a finger in my ass, I lost my concentration on his cock, but he just kept fingering my hole and it was feeling good. Then he worked another finger in and although it hurt, it felt good at the same time as I pushed my ass harder into his hand. That is when he then pulled them out, jumped up, went over to his bag and pulled out a box of condoms and a bottle of lube.
"I was hoping I could finally fuck that hot ass of yours.", he said refering to the fact he already had the supplied needed.
He had me get up on all fours on the bed. Then he squirted some of the lube in the crack of my ass and began working his fingers back in my hole using the lube. The lube made it much easier for him to finger fuck my ass and soon he had worked his three middle fingers into my ass and was stretching my hole.
He was standing next to the bed as he pulled his fingers out and reached for a condom. I took the opportunity to reach over and play with his balls as he opened the condom, put it on the head of his cock, and rolled it down his shaft. Seeing that hard cock wrapped in a condom brought back memories of wrapping my own cock in a condom back when I lost my virginity to the neighborhood slut when I was 16. That was exciting first time sex and now I was about to loose my anal virginity to the cock that was about to be shoved up my ass. Then he climbed up on the bed behind me, squirted more lube in my crack, and laid his cock between my cheeks and started fucking motions to work the lube onto his cock. There is nothing in the world like exploring new sexual activities, including having a guy run his hard cock up and down your ass. Then I felt him back off and place the head of his cock at my hole and I knew he was going for home.
He slowly pushed the head of his cock into my ass and began pushing his way deeper. I felt a burning as he worked in a couple of inches and stopped to let me adjust to him. Then as I pushed my ass back, he began slowly fucking my ass and working his way in. Pain turned to pleasure as he worked more of his cock deeper into my ass. I could tell he was all the way in when he gave the last little push and his hips were grounding against my ass as he held himself there for a moment for both of us to enjoy the moment and allow me to adjust to his now buried member.
He began fucking my ass and I grabbed a couple of pillows and buried my chest in them so I could maintain a solid position as he increased his pace and stroke. This is when I found out how vocal he was during sex as he began saying how fucking tight and hot my ass was, telling me to take his cock like a man, that he was going to fuck my brains out, and a lot more, and this just made me hotter. I could feel his balls slapping against me as he thrust in and out of my ass with long hard strokes. He ordered me to play with my cock so I reached around and grabbed my own dick and gave it a squeeze. I knew I would cum if I did too much, so I just squeezed my cock and tried to concentrate on saving it. Soon he was really ride me hard and nearing his own climax as he was breathing hard and making moves I recognized as nearing the point of going over the top. I could actually feel his cock getting harder when said he was cumming and he rammed it hard into me two last times and buried it as far as he could into my ass. I felt his cock twitching as he filled the condom with his hot cum. I just squeezed my own cock as I was about to cum from the feeling in my ass when he reach around, grabbed my cock, and only tugged a few times before I unloaded another round of cum on the sheets with his cock still buried in my ass. He pushed forward and we collapsed on the bed. He then said he had forgotten how hot and raw man sex could be and that he hoped I had enjoyed it as much as he did. NO QUESTION, I DID!
Before the night was done, I blew Todd to his second climax of the night and pumped his cum out all over his chest and stomach. And as we were showering to cleanup, I could not help but to get hard again so I ended up blowing my third load all over him in the shower after he jacked me off. It had been years since I came three times in one night. I was spent.
We spent the next four days exploring my new bisexuality. We paid a late charge on the video as we kept it the whole time and acted out many of the scenes, minus the chicks of course. We took turns filling condoms in each others ass, but mostly, we enjoyed oral pleasures and I did learn to deep throat and to swallow loads of cum too. He is the only man I have been with so far and we have managed to arrange two conferences since our first one for more suck and fuck sessions. I only wish he had pushed the issue years before when we lived in the same city and were younger. chipa2000@hotmail.com