The Tables Unexpectedly Turn

by Tristan I should give you a little background. My fuck bud lives in a little town about 1-1/2 hours away from me. I live in the big city, and he often comes for professional or personal business. Sometimes he stays overnight, which means we can have a motel room for privacy. Other times... well, we do the best we can (see my other story, "Sex in the Woods," in the Solo and All Male section). We are both married with grown or nearly-grown children. We've been seeing each other for over two years, whenever we could manage it. Anyway, for as long as we have been screwing around together, it has always been that I was the bottom. I don't really know how it turned out that way, but I don't object because I love to get fucked, and he is a great lover. He has expressed an interest in me fucking him, and on a couple of occasions we tried it, but I never felt like he was emotionally or physically ready to take it up the ass. It was really painful for him (no, I am not bragging! My dick is not nearly as big as his!). I was more concerned with hurting him than with fucking him. Because of my reluctance, it was hard to stay hard. It just never happened. Yesterday, though, was different, and totally unexpected. He was in town overnight for a professional meeting. As usual, when he had checked in to his motel room and called me at my office to let me know where, I left work early to meet him there, arriving about 3:00. We wasted very little time undressing each other between sloppy kisses. We were soon rolling around on the bed, kissing, sucking, fondling, poking, rimming, 69ing. It had been a long time since we last saw each other, and we were hornier than a herd of satyrs. I had just bought a brand new bottle of AstroGlide, which was something that we'd never used before. I was anxious to try it while he was fucking me since I had heard lots of good stories about the stuff. We had always used K-Y gel before now. He brought a bottle of baby oil, because we sometimes like to give one another a deep sensual massage. This is one of my favorite things, to be straddling his backside with my dick nestled in his ass crack ("hot dog on a bun") and pouring on a lot of oil and rubbing it into his back and shoulders and neck. It also affords me the opportunity to play with his ass, which I love to do! So we're making love there in the motel room, and I saw the baby oil and suggested that he let me give him a back rub. He quickly agreed and turned to lie on his stomach. I poured on the oil and firmly rubbed it in all over his back, neck shoulders, sides, arms, and thighs. He was issuing groans of approval, so I kept it up for a while longer. I moved ever-so-slowly toward his ass and poured some oil onto his cheeks and into his crack and then rubbed it in, massaging his cheeks and thighs, inside and out. My fingers soon wandered down his ass crack and pushed gently against his pretty pink hole. He spread his legs apart a little more and lifted his pelvis a little away from the bed. To me this was a signal that he was offering his ass to me for my enjoyment -- and his. It also gave me access to his cock, so I reached in between his legs and pulled his dick and nuts out from under him. I once downloaded a video clip of a great ass massage, with closeups of the guy's asshole while his lover fingered and poked, with the oil glistening off the skin around his pucker. So I did my best to duplicate what I saw in that movie, and if I say so myself, I did a pretty good job. I added my own special touches, which included my mouth and my tongue. I mixed generous amounts of my saliva with the baby oil, and I gently kissed and licked his sweet ass. I ran my tongue all around his hole, then up and down his crack. His balls and his cock were still sticking down between his thighs under his body, and I included them in my routine, kissing and sucking. I do love to bury my face in that man's ass and crotch! As I was fingering his asshole, I got a little more aggressive and began pressing a little harder with my middle finger. I pushed in just a little, waited for his reaction, and then pulled out. There was no reason to hurry, so I took my time penetrating. At first he flinched a little, so I backed off and took it more slowly. I reached for the AstroGlide and added just a couple of drops to my finger, and tried some more to enter him with my finger. The lube made a lot of difference, and I could tell that he was more comfortable with it. So I inserted my finger into his virgin asshole just a little more, then out, then more, then out again. When I got to the second knuckle he flinched again, so I eased off some. Then I tried it a little slower, all the time softly telling him to just relax, and I could feel his sphincter muscles loosen up a bit. So I pressed gently forward, and in no time I had my entire finger in his ass. He was becoming much more comfortable with this, and I could hear groans that I recognized as pleasure. So I felt around inside his ass, and massaged his prostate a little, and that's when he really reacted! I thought for a minute he was going to cum, judging from the sounds he was making. He didn't cum, but he was definitely enjoying this new sensation. After a while of this, I decided to try to use both fingers, and at first he was uncomfortable, though he didn't say so, but I could tell. So I again took it all very slowly and with more AstroGlide, and soon he was nicely stretched and relaxed with both my fingers in his ass. And I pushed and twisted and felt around in there, all while he was whimpering his approval. We spent a few more minutes like this, and I could tell he was really enjoying this. After a while I stopped and gently pulled my fingers out, and moved to lie on top of him so I could kiss the back of his head and neck. Then I started to pull away again, and he wordlessly reached for my hard cock and pulled it back toward his ass. I wasn't sure what he was trying to say, so I lay back down on him for some more kissing, again nestling my cock in his crack, and in a few minutes I again rose. Once again, he reached for my cock and pulled it toward his ass, and I realized it was a silent but unmistakable gesture for me to fuck him. Well, with the combination of baby oil, AstroGlide and lots of saliva, he was already well lubed up, so all I needed to do was quickly roll on a condom and slip right in.... MAN! What a fantastic feeling! I took it slowly and gently, since his is ... uh, well, was ... a virgin asshole, but I was surprised at how easily I went in, and how calmly he was able to take it. Once in all the way, I realized what a nice warm place it was to park my dick. I started pumping, slowly at first, and speeding up as we both became more accustomed to it. It didn't take me too long, and I urgently whispered, "I'm cumming! I'm cumming!" And I must have ballooned that condom! I pumped out squirt after squirt of my hot jizz into the condom in his ass, and I'm not sure, but I think that I may have passed out for an instant, or at least gotten very light-headed with ecstacy. My hips were plowing away at his ass as if we'd been doing it for years! My balls were slapping against his perineum while I lay between his legs and fucked him, fucked, him, man, I mean I really FUCKED him! Even as I write this I can't believe it happened! But it did, my friends! After I had squirted my last, I started to pull out, but he stopped me and quietly asked me to please lie there for a while longer, with my cock still in his ass. So I did, and I would slowly and slightly move out and in, out and in (that's what he does when he has fucked me, and it is a great feeling!). I lay there for several minutes, still inside him, lovingly kissing his neck and shoulders, and I see the most serene and satisfied look on his face. I know the feeling! And then, while I am still very sensitive, he starts to contract his sphincter, making his asshole "grab" my cock... man, it sent me into paroxysms! Every time he did that I jumped, because it was excruciatingly sensual! Pretty soon I decided that it was time to get off of him (I'm no featherweight), so I slowly pulled my cock out of his ass, which was also a new and different sensation. He just lay there exhausted as if HE had been the one who orgasmed. I went to the restroom to dispose of the rubber and to get a warm washcloth to clean us up. I cleaned the mixture of juices out of his crack, and then cleaned the jizz off of my cock. Then we lay there together cuddling and just enjoying the moment. What a day! By the way, in case you're wondering... no, he didn't fuck me, but I did suck him off. He really loves that, and I love doing it for him! Please let me know if you enjoyed this story!