This is a true story (although I did change the names, just to be slightly discreet), and while I've been fortunate enough to have some really fun adventures over the years, this latest one came out of left field.
My partner and I decided to go for a "sensual" massage at a place in Manhattan. The reviews for this guy were very positive, and while none said so explicitly, it seemed clear that "happy endings" probably could be part of the bargain, even though his prices were no different than a normal massage.
I called Jim to set up an appointment, and he sounded nice. I explained that I was half of a long-term gay couple. He was clear that he's straight, but he's dabbled with guys on occasion over the years (so maybe he really was bi?) and had no problem with working on a gay couple.
When the day of our appointment arrived, we were looking forward to it, but it was just one part of a fun day we had planned, doing some shopping, getting massages and then heading out to dinner with a friend. I won't spend too much time on that first appointment, since that's not where things really got good. Let's just say that the first day's massages did, in fact, include happy endings. Actually, we wound up doing some mild, mutual fooling around, with cocks getting sucked and then Jim finishing me off with a handjob that had him impressed by the huge load I shot. Matt was similarly satisfied, and we said we'd be back.
During that first visit, Jim did mention that he'd actually bottomed in the past, but he said it had been a long time since that had happened. He commented that, "if we did something like that, you guys would have to spend a lot of time getting me ready." Okay, so he may usually fuck girls, but "bi" definitely seemed like the term for Jim.
Since our play that first day did involve some rimming of Jim's hole and slipping in a finger, we knew that he was extremely tight, and we had no doubt that he was right. Lots of foreplay and loosening of that tight hole would be required.
I just realized, before I go on, that I haven't described any of us at all. Matt and I are in our forties. We're not in the shape we once were in, but we're good enough that there still are hot guys who like having fun with us. We've been together since I was in my twenties, and we're really very happy together. We are very much in love, and we have great sex together. In fact, when it's just us, we fuck bareback, and there's nothing that feels as amazing as that, whether it's my bare cock in that hot, tight ass of his, or him sinking into mine until I feel his load filling my hole! But sometimes it adds a bit of fun to grab some condoms and have another guy join us in bed. Going back to our unexpectedly enthusiastic masseur, Jim is in his 30s, nicely built, with beautiful blond hair, a handsome face and an amazingly hot ass! His face has gotten him some acting work in New York (he's another of NY's many frustrated actors doing something else to make ends meet), and we learned that ass comes from lots of running to stay in shape.
At the end of our first visit, Jim said he hoped we'd be back very soon. He was very anxious to see us again, and it seemed clear after the extra fun that he wanted more than for us to be repeat massage clients. We told him we'd do our best, but in the end it took several weeks for our schedules to let it happen again.
This time, as the day approached, Jim and I exchanged text messages, staying in touch way more than I would for any normal masseur. Normally, we'd set a date and that would be that. By the morning of our appointment, Jim was sharing how horny he was. Okay, so clearly we'd be having some extra fun, but I guess that wasn't so surprising. Then as the hours passed, he mentioned that he'd fucked a hot Asian girl last weekend but what he really wanted was to get fucked himself. So we definitely were going there, assuming we could get him ready! Then he added that he'd never had a couple tag-team him, and he thought it would be hot to have us take him there. His last text message before we headed to his place was to say he might just have himself on the massage table, naked with his ass in the air by the time we got there. I responded that we didn't have to rush things, but I liked his attitude!
When we got there, he was in his underwear and a button- down shirt, like Tom Cruise in "Risky Business" and he looked really good! We chatted for a bit, and then he asked what we wanted to do. I mentioned that I actually could use a little massage work on my shoulder, as I'd pulled it, so he got down to his real business, working out the kinks.
He got the knots worked out and slowly proceeded to lean more and more into my back, as his strong chest was pressed into my back and his hands wandered more and more. From my position, face-down on the massage table, I could reach one hand back to roam his great, muscular thighs and reach up to enjoy that nice, round, beautiful butt of his! I couldn't see anything at that point, but Jim suddenly let out a moan and I had a good idea that Matt must have done something to make that happen. Sure enough, when I picked up my head and looked over my shoulder, I saw that my husband had pulled down Jim's underwear and had his face buried in that amazing ass, clearly licking and probing his hole.
I just watched the rimming go on for a minute or two. There was something very hot about Jim writhing on top of me as he got his hole licked! But then I had to get involved, so I turned a little to a position where I could reach more. I soon had Jim's hardening cock in my hand and was stroking him. He soon was pouring out lots of precum, and I used it to make his cock nice and slick, really getting a good stroke going.
A few minutes later, and Matt took a break from eating Jim's ass. We decided that we'd do better if we moved to the bed, and that's what we did. Matt and I quickly pushed Jim back, and Matt started licking along the length of Jim's cock, as I licked his balls. Jim said, "not too hard on my balls!" So I was gentler, but Matt kept sucking hard, as Jim then complimented the combination of Matt's sucking and my licking. Jim was moaning a lot. After a few minutes, he made us stop. He said he was getting too close to cumming, and he wanted to be fucked!
So we flipped him over and went back to licking that hole. Well, actually, Jim got on his knees, Matt went back at his hole, and I licked along the length of his cock, as it kept drooling precum. What a hot sight I had from under there, but the best was yet to come!
Matt is nicely hung, but my cock is very thick, so we thought it was clear that Matt needed to go first, so Jim could get accustomed to the feeling of getting fucked before I sank into that tight ass! As I kept making Jim moan with my work underneath him, and he kept sucking me (did I mention we'd gotten into a 69 with me underneath?), Matt grabbed some lube and a condom, slicking up his cock, rolling on the condom and then getting plenty of lube on the condom and fingering a bunch into Jim's hole. I stopped most of what I was doing, just stroking Jim's hard, slick cock, so I could watch what was about to happen. As I watched, Matt lined his cock up on that tight hole and slowly pressed forward. Jim gasped, moaned and panted as he felt Matt pushing into his ass. Slowly, I watched Matt push in, until finally I saw his balls press into Jim's ass. Jim was about to lose it, so I stopped doing anything to him for fear of getting him off before I got a shot at that ass!
Matt pulled slowly back, and I reached up to feel where his hard cock met that hole. That was an amazing thing to feel, my man's rod stretching open the mostly-straight boy's hole! As Matt thrust back in, I felt the ridges of his cock pushing past with my fingertips. It was so hot, as was that continuing stream of precum Jim was pouring onto his sheets right next to my head.
The thrusting picked up in pace, and I had the best view in the world, inches away from that gorgeous cock and my man's balls slapping an amazing, tight blond man's ass! I knew the feel of that cock in me and those balls slapping my ass, so I knew Jim was getting a great fuck!
Not long into the fuck, Jim lost most of the focus on my cock and was lost in the feelings coming from his ass. (Later, he'd worry aloud that his enjoyment of both of us might have gotten his neighbor upset from all the noise!) After several minutes, I commented that I'd like a turn. So we all switched positions, I put on a Trojan Magnum condom (did I mention how thick my cock is?) and put on lots of lube, pushing a bit more of the lube into Jim's ass with my fingers.
I was very hard and anxious to slide into that ass, but Jim hadn't been fucked in quite a long time and I didn't want to hurt him. (Measuring my cock at its base, it's 6 inches around... about 2 inches wide. I've never been with another man who had a thicker cock than mine, so I knew to be careful with Jim.) I started rubbing the head of my cock on Jim's hole. He moaned as he felt that, as he and Matt worked on each other's cocks. I slowly pushed forward, and Jim's head came up as he moaned loudly. The head of my cock pushed in, and Jim gasped. "Wait, wait!" So I did, as he adjusted. "Oh my God, that's big!" He seemed to be adjusting, so I made tiny little back-and-forth motions, to try to loosen him up. His gasps of discomfort started to sound like gasps of pleasure, so I pushed a little more in. He sounded like he could cum right then, so I kept going. It was a stop-start approach, as Jim gave me feedback on when he needed to wait and adjust. After a couple of minutes, we'd done it. My balls were pressed into his ass, and I held it there. He was panting and telling me how full he felt and how much he loved it. He told me I was pressing hard on his prostate, and it was driving him nuts. So then I started sliding slowly back out and then in, back and forth until I got a good fuck going. He couldn't even stay still, and he started pushing back with each thrust in. I'd been grabbing his hips, then his back. Now I reached forward and grabbed his muscular shoulders, pulling our bodies together hard with each thrust. It was turning into a good, hard fuck, and he was loving it!
After a few more minutes, we moved around, so I was on my back and Jim could ride me while Matt leaned in to suck him. He rode for a minute, but it got to be too uncomfortable for him, so we changed positions again, and I put him on his side. I straddled one of his legs, as I pulled his other up. I added more lube and slid deep into him. Jim was going wild as he took me deep inside him. By now, Matt had taken a break and was just watching as he smiled at me, enjoying the view of his man making this stud writhe on the end of my cock!
A few minutes more, and Jim said, "fuck me on the table!" He moved to his massage table and got on his back. I moved right up to his ass and slid right into him. I thought he was used to my size by then, but I guess it wasn't quite that simple. He gasped, his face registering part pain and part pleasure. "It's huge. You know it's huge, right?" I just smiled back at him. At that point, I figured I just had to thrust some more and everything would be fine. Sure enough, as I pounded that amazing ass, the look on Jim's face turned to pure pleasure. He was grabbing me with his runner's legs and squeezing me inside his ass, trying to send me over the edge, but I wasn't ready quite yet. I was enjoying the fucking way too much to lose it just yet, and all the years of barebacking Matt made holding off while wearing a condom a piece of cake!
By then, Matt was ready for another turn, so I pulled very slowly out, that alone making Jim moan in pleasure. Then Matt quickly lined up and sank back in. He found it easy, since I'd stretched out Jim quite a bit, but Jim still got enough of a grip on Matt's cock to make it good! That became clear from the sounds they both were making, and I really can't complain too much, since I was really enjoying the sight of Matt's cock sliding in and out of Jim's ass, as well as watching Matt's pretty ass clench with each thrust! At that point, we'd been fucking that hot man for almost half an hour total, and I can't say I was surprised when he announced that he couldn't hold it anymore and was going to cum! Moments later, he started shooting a thick load of cum onto his abs, and Matt kept thrusting, helping to drive that load out of him. Less than a minute later, it was clear that Matt was cumming. He gave several very hard thrusts--so hard I was worried the massage table might collapse--and then he was cumming inside Jim's ass! He held it in there as he shot. After Matt's orgasm had subsided and he pulled out, I could see the condom hanging off his still-hard cock, filled with a huge load.
That left me with a very hard cock, while both of them seemed quite nicely satisfied. Fortunately, Jim seemed to appreciate what we'd done for him. He smiled and pushed me back onto his bed. With that, he got between my legs and started stroking my already well-lubed cock, as he licked my balls. After all we'd done, it didn't take long and I was approaching orgasm. When it hit, it was big. I felt the orgasm from head to toe, and my cock shot cum straight up in the air. "Holy shit" is all I heard, as my semen covered Jim's hand, my groin, my stomach and I don't know where else! As my orgasm subsided, Jim grabbed a towel and went to work cleaning me up.
After relaxing for a few minutes, I got up, kissed Matt and went to wash up, seeing that Jim had grabbed a blanket and was curled up on his massage table. He looked up, smiled and told us "that was incredible, but you guys wore me out. I can't even move!"
We told him that was fine, he should just stay there. He seemed fine with that plan! He really seemed wiped out, and he reiterated that he'd had an amazing time, even telling me later by text that it was great. By the time we had to head out to meet a friend for dinner, Jim told us he was okay but still wiped out and hadn't moved from where he was lying! Needless to say, we all had a good time! Will it happen again with Jim? It might. Time will tell!
I hope you enjoyed this story (feel free to tell me if you did: nygayguy@gmail.com). I could think of ways of spicing it up, but then it would be a work of fiction, while every word of what you just read happened. In fact, as I type this, it's just yesterday that it happened, which may be part of why my dick is throbbing as I recall it. That was a fun afternoon!