This story happened some 40 years ago when I was about 12 years old. I had been with Tom for about a year by this time, and we were having sex on a regular bases. Tom was an older man whom I worked for cleaning the local bar, and we would hang out together as well.
Sex with Tom mostly consisted of me jacking him off while he would play with my dick and feel up my ass. Sometimes we would 69 until he was ready to cum and then Tom would pull off and catch the cum in a rag. I enjoyed this the most because when Tom would be sucking me he would put his finger in my ass, which would usually bring me to orgasm real quick, I could orgasm but I didn't shoot anything at this time. But never would he give me his fluids, which was becoming a drag. Anyway that's another story I'll have get into some other time, for now this story was how I lost my anal cherry to someone else other than Tom.
Till was Tom's landlord and the caretaker of the apartment building Tom lived in. This apartment building housed only men and tenets were not allowed to have woman over. Till was given his own place that was separate from the apartment building but was located in back of the building. One day Tom and I were cleaning one of the other apartments for Till and I remember we were in the closet moving stuff around and seeing what was in there. Tom was bent over picking stuff up and I was standing in back of him looking over his shoulder and Till was behind me telling Tom where to put this and that as he picked things up.
At some point I felt Till press up behind me like he was trying to see what Tom was picking up. I then felt Till wrap his arms around me and just hold me like he was trying to see over both me and Tom. After about a minute of this Till slid his hands down and now he had one hand on my stomach and the other hand on my crotch.
I thought "What's going on?", but figured he was just trying to move me over so he could see better. But his hands had started moving all over the places he was touching. Which was weird, because it was making my little cock hard? Then as Tom started to get up, I felt Till pull back real quick and let go of me.
Once Tom was back to work on another part of the closet, Till and I were back to looking over his shoulder again and I felt Till put his arms around me again. After a minute I felt him rubbing my crotch again. He then started to squeeze my cock, which was really getting me hard now. This went on for a couple of minutes until Tom finished and started to get up. We all left the closet and that was the end of that. Or so I thought.
The next day I when I came over and I was heading to Tom's apartment I ran into Till. Till asked me if would like to do some work for him in his apartment and said he would pay me. I said sure let me know when he wanted me over. Till then did something I didn't expect and took me by surprise. Till reached out and squeezed my cock and said he would come looking for me later. He then let go of my cock, which was a good thing because I was instantly hard, and he turned and walked off. A little while later Till came by Tom's apartment and asked me if I was ready to come over and do some work for him. I said sure and waved so long to Tom and followed Till to his place out back of the apartment building.
Once we were in his place, I asked what he needed done and he said he need help in his bedroom. So I followed him in and he asked me pick up the clothes on the floor. While I was doing this Till pulled the curtains closed on the windows. While I was picking up some shoes Till came up behind me and put his arms around me. He immediately started rubbing my stomach and crotch, which started my little cock growing to a hard on. I liked this so much I kept acting like I was stacking some shoes up and let him continue feeling me up.
After what felt like minutes, I stood up, but Till didn't let me go and continued his ministrations of my body. Then he asked me if I would like to make $20.00. Being only 12, $20.00 was a lot of money to me so I said hell yeah, what do I have to do. He said "I think you know" and then undid my pants and reached in and just started jacking my cock. This was heaven and I really liked it. Tom had done similar things in the past but I think the strangeness of someone else I didn't know added to the excitement. So let Till continue.
Till continued to jack my cock and pushed my pants down so he could also feel my little butt. Every once in a while I would feel a finger slide over my butt hole. While Till was playing with my cock with one hand he removed his other hand from my butt and started undoing his pants. When he dropped his pants I turned to see what he was doing and saw his cock.
Wow, for an old man he sure had a long cock. It was 7 ½ inches long, uncut and skinny like the diameter of a cooked ball park frank. Till turned me back around and while playing with my cock he started to rub his cock on my back. While this went on Till would take his cock and slide it between my butt cheeks. This was a real turn on for me as I felt his cock head slide over my butt hole. Till then moved us over to his bed and we sat down and I started to jack his cock now. Till let me do this for a while and then told me to stop so he wouldn't shoot too soon. So I did. He then asked if he could rub his cock between my butt cheeks and shoot his cum on my back. I was so excited by this thought I pulled the rest of my clothes off and jumped on his bed naked, and laid down on my stomach in answer. Till then reached over and started to rub my back and my butt. He would pull my cheeks apart and rub a finger over my hole and drive me nuts. This went on till I thought I would cum and asked him to stop and get on me and rub is cock over my butt. Secretly I wanted it to rub on my butt hole. Till stood up and took off his clothes and before he got on the bed he asked if he could tie me down. He said this would be a fun game and I would like it. In my hormone enraged mind I was so excited by this it never occurred to me to say no, and almost yelled yes.
He then got out some old ties he had and started by tying my hands to the head board frame. All the while he would slide a hand down to my butt from time to time and rub my butt and slide a finger over my butt hole. He then started tying my ankles to the foot board. This whole time I would secretly look over at his cock and watch it bounce up and down as he moved around. Finally he had me tied down and was ready to get on top of me. When he did, he did it very slowly. Once he was over me, and supporting himself on one hand, he started by rubbing his cock head up and down between my butt cheeks. Most of his emphases was on my butt hole. Finally he lowered himself on to me and began to rub his cock between by butt cheeks. After a few strokes he said this was not comfortable because I was dry, and asked if he could put some lube on me. I said yes, since I was already in heaven and couldn't think about anything except that long dick sliding over my butt hole. Till reached over to the bed stand and pulled out some Vaseline. Now in hind sight, I should have been scared, I was 12 years old, I was tied down, a man with a big cock was on top of me, and he was now applying Vaseline to my clinching butt hole and my butt cheeks. But I was young and dumb and in pure heaven, so I just laid there and enjoyed the sensations.
Once I was lubed up Till began to slide his big wonderful cock up and down between my butt cheeks. This felt fantastic, especially when the head of his cock would catch on the lips of my hole and then slip out again. This went on for several minutes until I heard him start to breath heavily and start to move faster and make longer strokes.
That's when things started to get out of hand so to speak. On one of Till's long strokes I felt the head of his cock poke right into my butt hole. I jumped at this and it slipped out and continued up between my butt cheeks. Till was starting to get really going now and was humping faster. A few strokes later the head again started to enter my butt hole, but a quick jump again dislodged this intruder from its warm berth in my tight virgin butt hole. But on the next stroke Till's cock would not be denied again and on his forward hump the head entered my butt hole.
Till stopped just in time before he went too far. He didn't pull out though and just stopped dead in his tracks and laid there. I begged him to pull out because this was causing me a lot of pain. Till slowly withdrew his manhood from my hole and let me recover before he started humping again. As he slowly started his humping motion I got back into the feeling his cock rubbing over my now really sensitive butt hole. This was causing me some real intense feelings.
After a few minutes Till began to speed up again. He was moving fast and breathing hard and finally announced he was almost ready to shoot. A few strokes later he said he was ready and took one long, I mean really long back stroke. And then it happened, he arched forward with all he had and in one quick stroke my cherry was busted. The head of his cock hit the entrance to my butt hole and continued right past where his cock head had earlier opened me up. His cock was embedded so deep in that one stroke I thought I felt it go into my stomach.
Till knew what he had done, and didn't quit. He took another 3 or 4 more fast strokes and then held fast and I heard him grunt as he shot my bowels full of his cum. By this time I was in a lot of pain and squirming to get out from under him. But the ties held me in place as Till emptied what must have been a gallon of cum into my battered innards.
Till then started those final slow short strokes that every man takes as his nuts are finally almost completely emptied. Those are the strokes we take when we just want to get those last drops into a warm and loving place.
After about 5 minutes Till finally held still with his cock fully hard and inside me as far as it could go. As I laid there and started to softly cry from the pain I noticed the feel of his nuts. They were right up against my nuts. That meant he had all 7 ½ inches inside me. While proud of myself for this, I was really in a lot of pain and begged Till to take it out. Unfortunately, Till was completely exhausted and couldn't or wouldn't move so he just lay on top of me until his cock began to soften. Once he was soft he began to move around to withdraw from me. He did the sissy push up and looked down at our union and said "thanks that was great." He then asked if I was alright. Even with his dick soft it still hurt a lot and I begged him to take it out. He said ok and slowly, ever so slowly, he began to slide his cock out of me. This seemed to take forever, but finally the head plopped out and I felt something warm running down my balls from my ass.
Till got up and told me he would clean me up first before he untied me. The then got a warm cloth and started to wipe me up. This was feeling good until he got to my hole, I jumped at the pain this caused and asked him not to wipe there. He then worked all around my butt hole and then just laid the warm rag on my butt hole. While I laid there he began to untie me. Once I was untied I tried to roll over and sit up, but this caused some considerable pain, so I just laid there. Once I was able to sit up I reached to the floor to pick up my underwear and noticed the cum mixed with blood running down my leg. This kind of freaked me out but Till set me to rest and said I would be alright, all I needed to do was take a warm bath and everything would go back to normal. We then got dressed and as I was leaving Till gave $30.00 and said that was for the extra mile, Hee Hee. Instead of going back to Tom's apartment I walked home. At home I got lucky nobody noticed me walking in with a funny bow legged walk. I just went right to the bathroom and took a bath. Till was right though, a warm bath did get everything to go back to normal. All though I had to change the water twice I did finally stop bleeding from my butt hole. I avoided Tom's apartment for a couple of days because I didn't want Tom to notice how sore my butt hole was. After a couple of days though I did start going back to Tom's apartment, where we finally had our brand of sex. But I didn't let him touch my hole for another 2 days.
After that two days I was back to normal and the pain was now gone. I was walking in the front door of the apartment building to go to Tom's apartment when out of nowhere Till appeared. He asked how I was doing and if everything had gone back to normal. I looked around to make sure we were alone and said yes. 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?
Do you want to know the answer to that? Then email me at mugrb8030@yahoo.com.