Conner and I weren't quite boyfriends but also were not just friends either. We had a very sexual relationship and had sex with others on our own and together. He also had his semi-closeted social life. The summer after his senior year he stayed in town to work in a lab. I had the luck of renting out a summer share in Provincetown aka as Ptown with 2 friends. I mainly went on weekends but managed to have 2 full weeks in August for vacation. I invited Conner for his first visit to Ptown. If you don't know about this place, think cute seaside town that is taken over by gays every summer. It has some similarities to Fire Island but a more casual atmosphere. The beaches are full of hot men in speedos or less and town was always packed with vacationers, drag queens and other summer travelers.
Conner and I took the ferry on a Thursday so that we could have an extra long stretch of time. The first night was going to be a sports gear party at a small place called Purgatory. We planned on going in wrestling singlets that I brought. We wore them under regular clothes and checked our clothes upon arrival. It was quiet so we went upstairs for a drink on the porch. There were a few others guys in soccer kit, football jerseys and a few others in singlets. After a little liquid courage, we were relaxed enough to want to go dancing downstairs. It had picked up a lot and it was a very sexy crowd. We danced closely with our bulges rubbing against each other. It was the kind of place where guys got warm and sweaty and lots happened on the dance floor. We were both hard in our singlets and made out often.
We took a break to get some water and settled in an area overlooking the dance floor. I embraced Conner from behind and was super horny rubbing my hands all over his body, especially his bulge. We were standing next to a group of guys in singlets who were all chatting. One of them kept making eye contact with us and eventually came over to talk with us. His name was Keith and was brown haired with an amazing bubble butt and appreciable bulge. We bonded over Ptown beach days and singlets. I mentioned I have a collection at home so confessed how awesome it was to be out in one. Keith introduced us to the rest of his friends, a mix of guys from Boston, DC and San Francisco. We were standing in a tight circle and everyone was super friendly. There was lots of arms around shoulders and it was clear that 2 guys were a couple.
We ended up dancing as a group which led to lots of grinding against each other and kissing. Conner and I were having the time of our lives. All of us were hard and our spandex bulges stained with precum for the whole club to see. The night continued on and we continued to bond with the other guys. The club closed and we headed out to the street. We were congregated on a side street by the club and deciding what to do next. It was clear that we were not ready for bed. Some of the guys were talking about grabbing pizza while others were openly interested in going to someone's place. They were all staying at different places without space for a large group to hangout. I went over to Conner and asked if he would be interested in having some people over. I also whispered in his ear that this would likely turn into something sexual as Ptown house parties are notorious. He said a very enthusiastic yes and then we invited the group. There were 9 of us. We started to walk to our place wearing only our singlets and carrying our regular clothes. We were getting all sorts of looks and playful comments from others on the street. We also were not shy with affection as we paraded down Commercial Street and past the pizza place where people congregate after the clubs close.
We made our way to the house and headed upstairs. I had the master suite with a king size bed so there was plenty of space for everyone. As soon as we got in the room guys were taking off shoes and making out. Conner was kissing Keith while I was embracing the couple, Tyler and Sam. They were dreamy California guys with big hard cocks stretching their singlets. I got on my knees and sucked their cocks through the material while they kissed. Tyler pulled his straps down and I pulled his cock out and started to suck him while rubbing Sam's cock. I then reached up to pull at Sam's strap and he took the hint to strip down. I was taking turns sucking each of them off. Meanwhile, Conner was sucking off Keith who was laying across the foot of the bed. Ross and Aiden were 69ing at the head of the bed while Mark was on his knees sucking off Daniel. It was so hot to look over and see all these hot guys getting each other off. I was focused on the two cocks in front of me but would make sure to enjoy the view around me. Tyler grabbed my arm gently and pulled me up. He and Sam both grabbed a shoulder strap and pulled down my singlet. It slid down to my ankles and I stepped out of it. They did the same. Sam pushed me on to the bed and they both started to tongue my cock. If you have never experienced being serviced by two tongues, it is an intense pleasure. Pretty soon Conner leaned over the bed next to me as Keith started rimming his ass. Conner started to kiss me and massage my nipples. I looked up and watched Keith stand up and slide his cock between Conner's ass cheeks knowing that Conner was going to get pounded pretty soon. I pointed to the bedside drawer and Keith got the hint. He grabbed the lube and poppers from the drawer. He gave the poppers to Conner and lubed up Conner's hole. He then coated his cock with lube and started to enter Conner's hole. I sat up and massaged the heads of Tyler and Sam's. By this time Sam was sucking my ball sack and taint while Tyler sucked my cock. I moaned loudly to let them know how aroused I was especially when being rimmed.
Tyler stood up and said that he gets to fuck Sam any day so now it was my turn. I stood up as did Sam. My hole was wet with Sam's saliva but I would need to lube up in order to take Tyler's 8" uncut cock. Sam got on the bed, laid on his back, lifted his legs up and spit lubed his hole. It was clear he wanted me to fuck him. I lubed up my cock and got between his legs. As I entered him, Tyler started to finger my hole and lube me inside and out. Sam was a loose bottom and I was in him easily. I pulled Sam to the edge of the bed so that Tyler could start to fuck me. I felt the head of his cock enter me. I grabbed the poppers and took a big hit. I offered them to Sam who leaned up to take a snort. Tyler took the bottle from my hand and took a hit himself. He slid into my ass slowly and in a few minutes I was loose enough to take his entire cock inside me. It felt amazing being between these two studs. By this time everyone was fucking. I had no idea we could all squeeze on the bed so well. Hands were everywhere and it was clear we were all having a great time. A few minutes later after riding my ass, Tyler swapped places with Keith. Keith had a thicker but shorter cock so it took a little adjustment. Conner welcomed the change with a moan. A few minutes later Sam started screaming as he started to cum all over my hand and his chest. I came a minute later unloading inside Sam and Keith let loose a load in my ass. So hot to be seeded with his cum. A steady stream of orgasms could be heard across the bed.
We all collapsed on the bed and took a breather. Some of us migrated to the kitchen for a drink while others rinsed off in the shower. Not long after we started to get frisky again and another round began. I started to kiss Daniel while Conner was cuddling with Aiden. Ross and Sam paired off and things started up again with everyone back on the bed. I could taste the cum from his first load on Daniel's cock as I started to suck him off. He had a beautiful cut cock that I was throughly enjoying. I teased his hole with my finger and he moaned in appreciation. I flipped him over and lubed up his hole as well as my cock. I slid in easily and could feel someone else' load inside of him as I fucked his sloppy hole. I leaned over to kiss him as I continued to fuck him. I then felt a tongue on my ass and looked back to see Conner bent over rimming my hole with Aiden behind him doing the same thing. Conner then lubed my hole up and slid inside me. Aiden started to fuck Conner while I tried my best to keep a good rhythm fucking Daniel.
Clearly Conner was at ease with the group situation but I loved how he was eager to still be with me despite all the manhood surrounding us. Daniel was a talented bottom and would clench his hole to tighten up for me. It felt amazing and I was more than turned on by the sensations I was feeling and watching the passion of everyone around us. Conner was the first to cum inside me and I could feel the two loads in my hole. I came next, filling up Daniel with another big load. I stayed inside of him as I could tell he was close to cumming and soon he spewed a huge load despite being his second of the evening. Aiden and Daniel came at the same time. The others were still going at it as we watched the remaining guys reach climax. At that point we went into the shower in pairs and rinsed off. My bed linens were covered with cum and lube, thankful for laundry service!
I was sitting on the bed talking with Ross and wished I could have paired off with him earlier. He commented how he liked my singlet and I loved how he filled out his too. I told him we could hang out anytime in something tight. He has a husband back in Boston (who was arriving tomorrow) but the husband wasn't that into gear so he would certainly be up for some gear fun in the future. Slowly the guys started to get ready to leave until it was Ross, Conner and myself. We pulled off the very sticky comforter, started to spoon together and fell asleep quickly.
In the morning I woke up with Ross' hard cock pressed against my ass and Conner spread out in front of me sound asleep. I sneaked out to piss and brush my teeth but slid back into the bed. Conner stirred and wrapped himself around me while Ross reached over me to caress Conner's body. A little while later we all were wide awake and reminiscing about the previous night. We also started talking about spending the day on boy beach in speedos. Ross smirked and asked what we were going to wear. Before I had a chance to speak, Conner jumped out of bed and was digging out suits. "I could use a hand choosing what to wear" he said. He slipped on a black Aronik suit first. I got up and went to my drawer of speedos. I grabbed a Japanese style blue Arena suit and pulled it on. I pulled Ross out of the bed to look at the others we had. He grabbed a striped N2N suit to start. After he put it on he went to the mirror to check out the fit.
We all congregated in front of the mirror and started to feel each other's bulges and asses underneath the tight material. I kissed Ross and Conner slid in to kiss my neck before moving onto Ross' nipples. Ross pulled Conner in for a kiss and I got on my knees between them. I started to rub both of their hard cocks in their speedos. I slid Ross' cock out of his suit, sucked on the head and then put it back in his suit so I could work on Conner. Conner was wearing one of my older suits that was threadbare and I could see his cock through the material.
We moved to the bed where Ross pulled Conner's suit down and had him on all fours. He started to work Conner's hole with his tongue. I went around to the other side and kissed Conner. He grabbed me by the speedo and indicated that he wanted to suck my cock. I moved closer to him and he started to stroke me through the suit. He then undid the strings and grabbed my cock from the top of the suit. I pulled the suit down to my knees and let him suck me off. I massaged his back as I watched Ross rim his ass and reach for the lube. Ross lubed up his cock and then mixed in the lube with his spit already coating Conner's hole. He slipped a finger inside Conner and worked in another finger to loosen up Conner. Soon after, Ross pushed his cock into Conner and Conner let out an enthusiastic moan. Ross was very thick and was going to stretch Conner out real good. He took it like a champ.
I pulled my cock out of Conner's mouth, slipped out of my suit and slid underneath him into a 69 position so I could work on his cock for a bit. He took the hint and resumed sucking me off. I reached between Ross' legs and massaged his upper legs and ass. I even fingered his hole a little. Conner then asked Ross to lay on the bed. Conner got up and sat on Ross' cock. He sat all the way down and rode Ross for a little while. Conner told me to get the poppers as he wanted to DP. I handed him the poppers and he took a big hit. He then directed me to enter him. It wasn't all that surprising but I figured last night was enough for his hole, apparently not. I got in close and coated my dick with lube. I slipped the head of my cock into his hole and very slowly started to enter him. I have done this before and Conner has also (see previous chapter). I know it is physically challenging to get started with DP. Conner took more poppers and said "More!". I slid into him as much as I could. Now both of our cocks were pressed against each other inside of Conner. We continued to pound his hole until I could feel Ross' cock pulsate and bathe Conner's hole with cum. The feeling of warm cum on my cock set me off and I came inside him. Conner shot his juicy load all over both of us. Cum was leaking out of Conner's hole a little so I pulled out. Conner laid down between us and we massaged his body all over knowing he just had a workout. We took a shower together and Keith texted Ross to tell him to get moving as it was a beach day. Ross headed home in just his singlet. We joked that it would clearly be a walk of shame. The plan was to reconvene at the beach. Ross ended up fucking me in the dunes that afternoon as Conner was fucked by Keith. Ross' cock was the thickest I took in a while so was slow to get started. We had a few observers watch and jerk off while watching us. After Ross flooded my insides with his cum, we retreated to the ocean to rinse off. My hole needed a day off the next day. It turned out to be a fulfilling trip in many ways and one that none of us would forget anytime soon. For Conner, it was an amazing introduction to a wonderful place.
P.S. This singlet orgy actually happened to me on a Thursday night in August 2015. My other housemates showed up the next evening and asked what I had been up to. At first I said "not much" but after a couple drinks confessed the whole thing to them. One of them still will joke with me on occasion and say "Nine guys?!".
Hello there reader and hopefully fellow speedo lover, thank you for reading my story and I hope you found it "stimulating". I have enjoyed Nifty for many years. Please remember that Nifty needs donations to keep things up and running. Please make a contribution of any amount, https://donate.nifty.org/