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His last shift
Tom walked into the office and turned in his uniforms and name badge, as Tom was leaving town for school and would be moving.
I thanked Tom for his hard work and told him that if there was anything I could do such as job recommendation or anything else, just let me know. Tom said there is one thing that you could do before I leave, but he didn't think I'd be up to it. I told him to ask and he shut the door.
Tom told me that he had heard that I was either bi or gay and had played with a few guys and wondered what it was like to play with a guy. I sat back at my desk and told him that while it's true, I'm bi and have played with guys, that for the most part I'm pretty much what you might call a top. He asked what I meant and I told him that I don't suck or get fucked as I prefer to be the one being sucked and fucking the guy's ass. Tom said he understood and wanted to try. I asked him what he wanted to try and he said as much as he could. I told him to come to this address, which I wrote on a piece of paper at 7pm and we would see about his request. He shook my hand and said he'd be there.
Well 7pm came around and no Tom. I started go to my office at home and do some work when the doorbell rang. It was Tom, he said that he got caught on a train. I showed him in and to the couch. I asked him why he wanted to try being with a guy and he said that when he went to college, there would be many different type of people and he wanted to experience things. I said ok, lets play then. I stood up and started to take my pants off and Tom did the same. I reached for his cock and started to stroke it and Tom did the same thing to me. Now Tom was about 6-7" long but not very thick. While I'm about the same length as he was but much thicker. I told him first to go to his knees and take my cock and put it into his mouth. Get a taste of it by rolling his tongue around the shaft. For a guy that claimed never to have done this, Tom was a good cock sucker.
I had gotten hard while my cock was in his mouth and he pulled off because he was gagging. He asked me if I wanted him to make me cum or if I'd teach him more. Now this was too good to be true, Tom was willing to either suck me off or let me fuck his virgin ass...of course I wanted to fuck him. I told Tom that maybe we needed to go to my room. I led him to the bed and had him lie down on it. I got a bottle of lube that I don't normally use as it's really slick and some guys don't like me to use it. I started to rub it on his asshole as he lifted his legs up and apart. I put him into postion to pretty much watch me play with him, even having a mirror close that he could see me working his ass. Besides HE FELT me fingering him and putting the lube on him. After a few minutes, I put a rubber onto my cock and told him that at any time he wanted me to stop, I would. He agreed and I lubed the rubber more and got between his legs. Put my cock to his hole and told him to take a deep breath and let it out slowly. As he did, I pushed my cock in. I had him do this a few more times till he got about 2-3" of my cock into him. Tom was hurting I could tell it and told him that maybe we should stop. Tom told me to go ahead...he was ok. I lubed him more and push in deeper. Tom's breathing was heavy as he struggled to take me. Finally I was all in his virgin tight ass. I slowly pulled out then back in several times, adding more and more lube to my cock. Finally I was able to go in and out making Tom moan loudly. I asked him again if he wanted me to stop and he said HELL NO! I asked him again cause now I was going to fuck him not slow stroke him. He nodded his approval and I started to lunge into him, faster and harder. Tom started moaning louder and louder, before he said that he couldn't take it any more...he shot his load all over both of us. I pulled out and stood in front of him. Watching him lower his legs and set up. When he did, Tom noticed that I didn't have any cum in my rubber. Tom was upset that I hadn't cum and he had and asked me why. I told him first that the rubber had some extra numbing agent in it and second I normally fuck a guy harder and in a different position. Tom asked what position do I like and told him that I love it when a guy is bent over or doggy style. Plus the numbing stuff isn't normally in my rubber. He told me to try it my way...meaning to take my rubber off and put a fresh one on. I wiped my cock off and he got into all 4's. I put fresh lube on him and the outside of my rubber and pushed it towards his hole. Tom was still very tight despite me fucking him moments earlier, but I got into him and started to fuck him. Slow at first to make sure he understood that I was about to fuck him hard. I picked up the pace and started riding him...I was about to cum and Tom asked if he could taste it. I took the rubber off and with just a few hand strokes...filled his mouth.
We rested a bit and talked about his first experience and he said it was different but he not only got off with me fucking him,but got hard again. Tasted his first taste of cum as well. I told him that this don't make him gay or bi, just because he tried this as only WE would know and I didn't make it a practice to telling folks about others.
I started to get up when I noticed Tom had gotten semi hard again. I thought to myself...I could handle him if he did what I told him.....