Some 40 years ago when I was 12, Till took my anal cherry, and for about 4 days my butt hole was sore and tender. Once my butt hole was back to normal and the tenderness was gone, I had been on my way to Tom's for some sex when I walked back into Till again. As I tried to push past him he put his arms around me and gave my cock a squeeze and said he needed some more work done again, would I like to come over? Before my cock could respond I pulled away and said I would think about and let him know, and took off as fast as could for Tom's apartment.
Once into Tom's apartment I felt safe again. But I couldn't stop thinking about that little squeeze from Till which made me hard. This was ok though because me and Tom were going to have sex. Tom was sitting on his bed watching TV waiting for me to come over, and once I walked in he invited me to sit on his bed with him to watch TV.
I jumped up on his bed and relaxed against the wall and started watching TV wondering when Tom would be ready to start. After sitting there for about 20 minutes watching TV, Tom had not started anything. I decide to get things going myself. So I reached over and started tracing Tom's dick through his pants. Tom's dick got hard and after a couple of minutes of this I felt his arm go around me and he started squeezeing my butt.
Tom finally told me to close the curtains, which was his signal that he was ready to start. I practically ran around his apartment closing curtains, and then jumped back up on his bed. Tom was waiting for me and when I jumped up on his bed he started making out with me. Making out with Tom never did much for me, but it sure revved his engine, and before too long he was fondling my cock through my pants.
When I reached down to his cock it was still rock hard and ready. So I started undoing his belt and pants so I could get to his cock. One of the things I liked to do when I would get his cock out, I would pull the skin back and watch the head as it would disappear back into the folds of skin. Tom was uncut and about 6.5 inches long, but about 3 inches wide and 2 inches thick. This was the biggest cock I had ever seen, considering I had only seen 3 hard cocks in my life and one of them was mine. So that leaves Tom and Till.
Tom then helped me to get my pants off and started playing with my little cock and fondling my ass at the same time. This put me to where I was leaning over his cock so he could use both hands on me. I think Tom did this for his own reasons because usually once I was in this position I would start to suck his dick. And I'm pretty sure he liked that because he was always asking for me to suck his dick. And sure enough, after he had rubbed my butt hole for few minutes his cock just seemed to call to me and next thing I know I'm swallowing his cock whole.
We did this for a few minutes and then Tom lifted me up and on to him for a 69. This was what I was hoping for, because I knew it wouldn't be long before he would stick his finger in my butt hole. And once he would do that it wouldn't be long before I would orgasm. And sure enough he found my butt hole and started massaging it and trying to stick his finger in to the first knuckle.
Tom stopped long enough to reach over and get some Vaseline, which allowed him to work his finger into my butt hole. This got me fantasying that it was Till's dick in me again. So I really started sucking Tom's dick good hoping he would cum in my mouth. Tom cumming in my mouth had been a secret wish of mine ever since we had started having sex. I must have been doing a good job because just as I was getting ready for my orgasm, Tom yanked me off of him and grabbed a rag and put it over his dick and shot his load.
I hadn't reached my orgasm yet so I was disappointed in that, but even more was the fact he didn't cum in my mouth. As I watched him cum into the rag I noticed the rag get really wet. He must have really shot a lot that time. I think it was because this was first time he had come so close to cumming in my mouth. I knew I had done a good job when I saw how wet the rag got.
After that Tom got up and started getting dressed, which was a hint to me to do the same and that sex was finished for tonight. So we went back to watching TV and all I could think of was I needed to orgasm. Then I remembered Till's offer. I waited a little longer and then told Tom that Till had said he needed me to do some more work at his place and I was going over there. He said ok and would see me when I was done.
I headed back to Till's wondering if he would be home and ready. I was sure hoping so. I knocked on his door and a couple of seconds later I was greeted by Till's smiling face. He invited me in and closed and locked the door behind us.
Not knowing how to get this going, and not for sure of what he wanted, I asked him what work he had for me. He smiled and said he needed me in the bedroom. We went into his bedroom and once we were in there his hands were all over me. I just stood there and let him feel me up and turn me on. He kept rubbing my dick through my pants getting me hard. Finally he undid my pants and let them drop.
With one hand he was playing with my dick and the other one was doing some nasty things to my bottom. This was really heaven when all of a sudden his finger went up my butt hole. I think that surprised him to find me already greased up and he asked me if had prepared before coming over to his place.
I had forgot Tom had greased me up earlier, I didn't want Till to know about me and Tom so I lied and said I did it because my hole was still tender from our last time. At the time I didn't know that Till did know about Tom and me. Which was why he had even started all this with me. He just smiled and asked me if I wanted him to stop and I said no it was feeling good. So he kept going.
I turned around so I was facing Till and started undoing his pants. I pulled his pants down and his dick practically poked me in the eye when it came out of his underwear. It was sticking straight out from his body and slightly upward. I had to marvel at how different his dick was from Tom's. So much longer but thinner. I couldn't believe it had once been all the way up my butt. I started to jack him off and feel how long it was, and admire the look of the head as I pulled the skin back.
The next I knew I had my lips wrapped around it. Till really liked this and started to moan. I kept at this for a bit while Till steadily worked his finger in and out of my butt hole. Till then pulled his dick back and said he didn't want to cum yet. I asked if he would like to rub his dick between my butt cheeks and cum on my back. He got real excited by that and said he would like that.
We finished taking our clothes off and I got on the bed. Till pulled out his ties and began to tie me up. I asked what he was doing, he said he liked this game and wanted to tie me up again. I was reluctant considering what happened the last time we did this. I made him promise me he would not put his dick in me, so I agreed and let him tie me up.
He soon had my ankles tied to the foot board and all the while he had been fingering my butt hole, I was secretly hoping he would fuck me again. But I remembered how much it hurt last time and didn't want him to fuck me. My body was a mass of confusion by these conflicting emotions. He would push is finger in and I would think, no I can't take his dick in there it would hurt me again. And then he would pull his finger out and I would think of how nice it would be to have his cum dripping down my legs again after he fucked me. Wow, was I out of control.
Anyway Till made the decision for me. He got on the bed after tying me up and just like last time he started rubbing the head of his cock on my butt hole. This got me really turned on such that I started to hump my dick against his bed. Till mistook this action as something else and instead of continuing to tease my butt hole with his dick head, he pushed forward.
Till's dick head popped in and I jumped trying to dislodge him. He would have nothing to do with that ideal though. I told him he promised me he wouldn't and he said he would just put the head in. We stayed that way for a few seconds as I felt Till jacking his cock while the head of his cock was in my tight little butt hole. The pain went away and then I felt Till start to move his dick in and out in short little strokes and it started to hurt again. I begged him to stop but he just laughed a little and said he would go slow and I would start to like it.
Till would pull it out for a second and then put the head back in and hold it there while he would stroke his cock with his hand. After a few minutes of this treatment Till was right and it quit hurting and started to feel good. Till kept this going for about 10 minutes and then he started pushing a little deeper on each stroke till I would complain and then he would just hold it there stroking it with his hand.
After a few more strokes I noticed he wasn't taking it out anymore, just pulling back till just the head was in and then he would push back in a little deeper. As this went on I was getting use to the feel and was now getting more turned on. So when he would push in I would push back instead of jumping and trying to dislodge his man meat. Then Till laid down on me and was no longer stroking his dick with his hand and was only working his dick in and out of me without pulling out. Till was fucking me and I was starting to like it.
Till was only about half way in and I was in pure heaven feeling him fuck me. Then he announced he was getting ready to cum. He started going faster now and the strokes were getting deeper. Then he pushed real hard and went all the way in. I couldn't take this and started jumping around trying to get him out, but again his tying me down worked to his advantage and all I could do was beg him to stop. So he did, but with his entire cock all the way in me. He wouldn't pull back and just held it there and told me to get used to it. I continued to beg him to pull out but he wouldn't and so I relaxed and finally it stopped hurting so much.
Once I stopped moving around and begging Till to pull out I think Till knew it was time to take me to the next level and so he started to do a slow hump. But every time he would start to move I would complain of the pain and for him to hold still. And he would hold still but only after pushing as deep as he could and then holding it there. We must have laid this way for about 20 minutes, with Till starting to move inside me and then holding still when I would whimper about the pain.
After this 20 minutes though Till started to hump and told me to relax because he was all the way in and I should be proud of myself. I think he must have been close at this time too, because now he wouldn't take no for an answer, and kept a slow steady hump going. Eventually the pain pretty much was gone and the most intense feeling began to take over my body. Oh my, I was getting ready to orgasm, and Till must have realized something was happening because now he went into overdrive. I thought he was going to go right through my stomach he was driving so hard. Which finally put me over and I started to quiver and spasm on the end of this big dick driving relentless into my body. As this happened Till grunted and told me he was going to cum a gallon into my butt.
I think this orgasm went on for about 5 minutes, it was the most intense orgasm I had ever had. I was exhausted and so was Till who was now resting his entire weight on me. I could feel his dick jerking in my butt as his cum was still unloading in me. Finally he held still and we stayed that way for about 10 minutes before his dick went soft.
When Till got off me he told me to hold still and he would clean me up, just like the first time. As I was laying there I felt his cum begin to leak from my butt and run down over my nuts. Then I noticed a different feeling, it felt like his cum was pooling under my belly? How could that happen? So I lifted my belly to see, and what I saw amazed me even more. I had shot cum! For the first time in my life, my little dick had shot cum out of it. It was all over the bed and on my belly. As Till was humping me he was driving my dick into the bed which brought me to my climax. But I didn't just orgasm, I had shot cum too!
I told Till to come quick and see what I had done. I showed him and smiling proudly told him he had helped me to achieve my first load. Till smiled back at me and told me thank you for giving him the chance to do this. Then he started to clean me up and untie me. This time when I tried to sit up and get dressed my butt hole only tingled. As I reached down for my underwear a glob of cum came out of my butt hole and ran down my leg. I looked at it and told Till that this time it was good because there was no blood.
Till told me I was now a big boy and each time would even more enjoyable. He then gave me $20.00 and told me to go have a good time at the store. I returned to Tom's apartment and watched a little TV with him before I headed home. The whole time I could feel Till's cum running out of my butt hole.
As I got up to leave and was walking to the door I looked back at Tom and he was looking at my butt and asked if I was ok. I said yes and left wondering what he was looking at. When I got home and went to take a bath I figured out what he was looking at. The seat of my pants were soaked all the way down to my knees.
I hoped he didn't figure out what caused it, and the next day when I was at his apartment nothing was said so I figured he didn't suspect anything. But when we were having sex this time, I insisted we 69. Tom got a surprise this time he wasn't too happy with, but that's another story isn't it?
If you like this story series let me know at mugrb8030@yahoo.com