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This is my 20th Chapter! It is hard to believe. Thanks to all of those who have given me feedback on previous chapters. Here is a holiday themed one to end the year.
You may have read previous chapters where I mention Conner. In real life he is a friend with benefits with a similar love for sports gear. He and I had some amazing times in the past so here is another adventure.
He went off to grad school and I haven't seen him in a few months. He messaged me to make plans and had a great idea. My city hosts one of the original Santa Speedo Runs every December and Conner wanted to organize a team. We came up with a list of guys we both knew and tried to drum up enthusiasm for a day in speedos, albeit a chilly one.
If you haven't heard of the race, it is a low key race raising funds for a kids organization. All the participants dress in speedos or swimsuits for the women regardless of outdoor temps and go all out with Christmas themed outfits. The day starts and finishes at a pub which means folks are drinking even before the 1 mile run. At that race distance, almost anyone can do it and since there is no official race clock only traffic cops boot you off the course for being too slow once they reopen the roads. The teams are mostly straight but there a few gay teams each year. Every year there are always plenty of hot guys on display. Conner's plan was to pull together a team of hotties from our past adventures and perhaps some newbies for a fun day with some after-race adventures. There are those who just wear speedos, those who admire a guy wearing them and those who get off wearing them or seeing hot men in a pair. Conner and I are in the last category and so the team would be made up of guys in all 3 categories.
After a few weeks of wrangling together a team, we had a good mix of guys we knew might be up for the adventure and a few of Conner's former teammates who were still in the area. It wasn't easy getting enough people but eventually we filled the roster. We all worked on the fundraising to make sure we met the minimum amount and coordinated on speedo colors and the plan for the day. We also booked a hotel room nearby the race to use after the race.
Conner is about 5'10", brown hair, brown eyes, nice bulge in a speedo and one of my types. He has a lean, muscular build and minimal body hair which drew my attention when I first crossed paths with him at the university pool. At first, I had seen him around the pool a few times and then we ended up in a 4-some and continued to hang out. We were lovers for a while but not in love and we had some amazing adventures together and with others. Since then he has been enjoying life down south and he fills me in on his wild times while we are apart.
Conner flew in a few days ahead of the race to stay with me and it was like he never left. He was living in Miami and had a nice speedo tan despite it being December. I have to admit I was jealous of his extended beach season. Conner bulked up a little this past year as he was doing more weights and less swimming. We fucked a lot since his arrival but this chapter is about the post-race activities we experienced so I will be brief. It was great waking up with him in my bed but the trick was to not get distracted by him and still manage to make it to work on time. We even made it to the pool for a couple of workouts.
The day of the run was chilly and very sunny. We got our outfits ready and headed to the pub around 11 am. Conner checked in with registration and found a spot for our team to congregate. The other participants were meandering in and getting in the spirit. Conner and I stripped down to our speedos as soon as we could but you could see others hesitating because of shyness or the cold outdoor temperature. It was 28 degrees F(-2 C) (yikes!). That is fine when dressed appropriately but a bit much when your only protection was a Santa hat, mittens and a skimpy speedo.
As more people showed up at the pub, the alcohol started flowing and with it the confidence for strangers to strip down into their speedos. Our team members trickled in and I was glad I knew a few of them. It was a reunion of sorts but half of the team was new to me, some were straight former team mates of Conner's. For those I knew, one had to not be too handsy in public while the others you had to feel out their comfort being in a speedo with guys they didn't know well. Conner and I managed to pull together a hot group of guys and seeing the team in person was quite stimulating. Since it would be a day full of seeing hot guys up close in speedos, I expected to be leaking precum most of the time. If the stain looked obvious I could just say I spilled my drink.
Our team decided on festive red speedos. We let everyone get whatever brand they wanted but a few of us who had hooked up in the past coordinated to get Sporti suits with a skimpier Euro cut and removed the liners to show off the goods as much as possible. No sense in being shy! I was especially excited to see one of Conner's former team mates, Adam, was wearing a nice Arena suit. He was another guy I crossed paths with at the pool and fantasized about. He was 6'2" with a lean muscular swimmer's build, dark brown hair and usually had a buzzcut. He was very handsome but with a midwestern upbringing, seemed as straight as they come with his baggy clothes and care free attitude.
After a couple of hours of pre-race festivities, it was race time and the organizers were drumming up the crowd. Everyone heads out on to the street and does jumping jacks, pushups or pretty much anything to keep warm. The race takes place in a well known shopping area which is pretty full of holiday shoppers. The event always draws an enthusiastic crowd and some bystanders are caught by surprise. The first time I witnessed it was a treat to see a steady stream of studs running by so it was great to be taking part this time.
The race started and we made our way down the broad street. We all had a few drinks by this point so were boisterous and eager to get back indoors. Our team kept together and hammed it up for the spectators. It was hot seeing these studs all around me. It was difficult to focus on putting one foot in front of the other when firm asses and big bulges were everywhere. The light mood of everyone and the comraderie of wearing speedos in the cold meant you were high fiving other runners and spectators. I even had someone tweak my nipple which was unexpected.
After we finished the run, we all ended back at the pub. No one puts regular clothes on but instead continue to drink in speedos. As you can imagine, people are tipsy and frisky by this point, gay men who have had sex in the past...even more so. Our team was clustered together and constantly rubbing up against each other. Sometimes it was purely an accident but sometimes it was intentional. At one point I was standing with Conner and a few others in a circle. I looked down and took in the view of 4 tight speedo bulges and varying degrees of arousal. I caught Conner's eye and he just licked his lips in admiration. The bar was fairly packed so going to the bar for drinks meant sliding past others with just the thinnest material between you and some other guy. After a guy rubbed up against Conner's ass and commented on his bubble butt we knew there were some other gays present. Conner managed to start talking to him and some other guys not from our team who might be good additions for later.
Conner and I had figured we would hang at the pub for a few hours after the race and then migrate to the hotel to continue the festivities and transition things later on to anything goes. Nate who was a part of our previous adventures would check in periodically to see when was time to head to the hotel. I loved his eagerness but some of us enjoyed being in public and flirting with some of the guys on other teams.
Conner and I had already told our team about the post-race plans but not everyone may be up for all the activities. We managed to get others to grab food and drinks on their way to the hotel while we went ahead to set up things.
The room was good sized with a living room area. In my bag were all sorts of things for later. I can only imagine what the hotel thought of a steady stream of guys in speedos heading up to our room. We lost a couple of teammates but about 8 made it to the after party. I turned up the thermostat so everyone would be comfy. By the time everyone arrived, guys were relaxing on the couch and chatting away. As the guys were hanging out, another few showed up who we met at the pub.
Conner came up to me and put his arm around my waist. We scanned the room and admired the scene. Guys were immersed in conversations and a few were openly flirting. We decided to turn things up a notch by kissing. We had a few quick kisses and then observed the room for a response. At first no one noticed so we kissed longer and more passionately. That was enough to see two others who were standing embrace each other. Nate was on the couch sitting with a guy named Jamie and had his hand slowly rubbing his upper thigh. Pretty soon the guy to other side was playing with Jamie's nipple.
Adam looked pretty nervous and he was off to the side of the room eating some snacks. I asked Conner more about Adam. He wasn't that close to him but knew he was well respected as team captain and always up for a good time. He was pretty shy when it came to dating so no one had any idea of his sexual interests. I mean he knew some of the guys here were gay and seemed comfortable with joining us up to this point. I walked over to him, introduced myself and make sure he was doing okay.
Adam's cheeks were rosy from a combination of the drinking and perhaps a little from seeing the guys all around him. I decided to feel things out with him through conversation. He realized that we crossed paths at the pool but had no idea I knew Conner. I responded by telling him that Conner and I dated for a bit. If he didn't realize I was gay yet, I wanted to make sure it was crystal clear. Adam had an amazing body and no visible body hair. He was much taller than me and so I had to look up in order to see his face. I kept getting distracted by his body and the way he filled out his speedo. He not only had a nice bulge but he also had an amazing ass which was a joy to see throughout the day, including when he was running ahead of me.
As we continued to talk, I noticed a few more guys with arms around shoulders and one couple were lounging on the bed alongside each other. The mood of the room was slowly turning but mostly it was a group of guys who were comfortable being up close and touching while in speedos. Adam didn't seem bothered by any of this nor in a hurry to leave. At one point in the conversation he put his hand on my shoulder and gently held me for a second. I looked up at him and made prolonged eye contact.
"Are you okay with all of this?" I asked while pointing around the room.
"I think so, I figure I'll hang out and then decide what to do" Adam responded.
At that point, Conner came over to us. He casually put his arm across my lower back and asked what we were talking about.
"Adam is deciding what he wants to do" I said.
Conner reached out to Adam and rubbed his hand down Adam's arm. Adam flinched a little and then smiled.
"Oh I am sorry, forgive me" Conner said.
"You're fine, your hand was cold, that's all" Adam responded.
Conner laughed and rubbed his hands together to warm them up. He then ran his hand down Adam's side stopping at the top of his speedo. He kept his hand resting on Adam's hip.
"How's that?" Conner asked.
Adam responded by stepping towards us and kissing Conner lightly on the lips.
"You know when I asked you to join this team, I had no idea you would be interested in anything more than the run!" Conner said.
Adam replied, "I am still figuring things out but always saw you with other guys and on Grindr, just never took any chances with those around me". It turns out he was one of the many faceless profiles on Grindr.
I looked at Adam's bulge and noticed his cock was hard in his speedo. It was laying horizontally and stretching the material. I could make out the head of his cock. I took this as a cue to get a little more intimate. I ran my hand down the length of his arm as he leaned in to kiss Conner again. Conner returned the favor by reaching out for Adam's speedo wrapped cock and massaged his bulge with one hand. I pulled the three of us in close and rubbed my bulge against Adam's leg while I massaged Conner's ass. I took turns tonguing Conner and then Adam's nipples. I got on my knees and was now face to face with two stretched out speedos. I ran my hand over Adam's cock while I took Conner's bulge into my mouth. I turned towards Adam's cock and put my mouth over his cock and moved back and forth over the tip and the length of it. I tongued the speedo around the head of his cock and could taste precum. Adam put his hand on the back of my head and massaged my hair.
Conner suggested we move to the bed because Adam's height was a challenge for Conner and I. I looked over and their was only 1 couple on one of the beds. The rest of the room had progressed to the point of everyone kissing or sucked off. Truly, mission accomplished!
Adam laid on the bed while Conner and I came up along each side of him. I focused on Adam's cock and Conner continued to kiss him. I freed Adam's monster cock from his suit, he was now fully erect and had a thick cock. I grabbed Conner's cock through his speedo and stroked him while he continued to kiss Adam. Then Adam pulled Conner forward, pulled down his speedo and started to suck Conner's cock. I worked Adam's cock. I spit into my hand, slid my hand into Conner's speedo to lube his ass and tease his hole. It was great to hear Conner moan with pleasure.
I felt someone's hand grab my shin from behind. I turned to see Nate at the edge of the bed with Jamie. They both had on the Sporti euro cut suits so assumed things were going to pick up a notch or two .
I turned to Adam and said "You should fuck Conner with that kielbasa, I hope I get a turn later". I then turned towards Nate and Jamie. I moved closer and grabbed both of their speedo covered cocks at the same time. I stroked them enjoying the way the material felt and the feel of their warm cocks underneath. Nate was kissing Jamie and so I leaned down to tongue Nate's cock through the material while I rubbed Jamie's cock. I slipped my hand into Jamie's suit through the leg hole and continued to jerk his cock. With Nate, I pulled his cock out his speedo and slid his cock into my mouth.
I was on my belly laying across the bed. I looked back to see that Adam and Conner had removed their speedos and Conner was sliding Adam's cock between his ass cheeks while moving up and down. The other couple on the bed were in a 69 and I was so glad the room had two king beds. The other bed was filling up as a few guys were entangled while others were scattered across the room. I told everyone that there were condoms, poppers and lube in the bedside tables. I made sure to bring plenty just in case this actually happened the way I envisioned.
Nate stopped kissing Jamie and leaned forward. He ran his hands over my shoulders and along my back towards my speedo. He ran his hands across my ass and then between my bare skin and the speedo. He slid his finger across my hole and I moaned to let him know I loved it. I leaned towards Jamie and pulled his suit down past his knees. I grabbed his cock and swallowed him whole. Nate moved onto the bed and removed my speedo. He pulled me around so my legs were off of the bed and my ass was exposed. I shifted so that I could still be sucking Jamie's cock. Nate spread my legs and began to rim my hole. I pushed my ass out to make it easier for him. Nate probed deeper with his tongue and worked me hole good. He stopped which made me look to see what was happening. He had grabbed a bottle of lube that was next to Adam. Adam's cock was fully inside Conner and Conner was slowly riding the length of Adam's cock as he began to adjust to the girth of Adam's cock. The look on Adam's face was pure joy.
That is when I felt Nate's cock begin to slide into me. Jamie slipped out of his speedo and moved on to the bed so I could continue to suck him. Nate's cock felt so good in me. He slid in and out while I reached back and rubbed the side of his hip. Nate picked up the pace so that he was sliding the full length of his cock in and out of my ass. Once I was loosened up, I pushed my ass back against Nate to get him as deep as possible. After a little while, Jamie said it was his turn and they switched places. Jamie lubed up and slid his cock all the way into me. They had similar sized cocks so it wasn't a challenge. Nate moved around front and shoved his cock down my throat.
I heard Conner moan "Cum inside me" and looked over to see Adam pushing upward at a rapid pace going balls deep with each thrust. He grunted and shot his load into Conner's ass. Conner collapsed onto him while Adam's cock slipped out along with cum dripping from Conner.
Jamie said he was going to cum and proceded to flood my hole. Nate followed with a load down my throat. I laid there recovering a bit when Conner said he still needed to cum. He got up off of Adam and plunged his cock into me. My hole was already slick from lube and cum so he just started fucking me. He didn't need much time to climax and added his cum to Jamie's previous load. Others in the room were heard climaxing.
After that initial wave of orgasms, everyone was relaxing on the beds and couchs. Guys were embracing each other while others were hydrating. A few slipped on their speedos while most stayed naked. Adam sat up on the bed so I slid up along him to chat. He sat their and occasionally would stroke his cock with a few fingers. I ran my hand up and down his upper thigh which made his cock swell. Once I saw his cock was hard again, I leaned over and took the head of his cock in my mouth. I tongued the head for awhile and then started to take more of his cock into my mouth. I nestled his balls while rubbing my other hand up and down his inner thigh. He was quite the mouthful so I resorted to using both hands to stroke the base of his cock while I swallowed the top half.
"Will you fuck me?" I asked Adam.
"Hell yeah but I want to do it differently this time" was his response.
He got up off of the bed and directed me to slide to the edge of the bed while on my back. He lifted my legs in the air and pulled me closer. I grabbed the lube and greased up his cock. I guided the head of his cock to my hole and he started to enter me. The girth of his cock took some adjusting but after being fucked twice it didn't take much time. I felt very full and absolutely overjoyed that he was into fucking me. He leaned over and kissed me while continuing to fuck me.
There were a few others getting back into action while others just watched, some fondling each other while observing. Conner was over on the other bed sucking one of the new guys while he was on his knees, ass up. It was clear he was waiting for someone to take the hint. A little while later, someone slid up from behind Conner and rubbed the head of their cock against Conner's hole. He turned around and smiled which led to him getting lubed up for another round.
Adam was much taller than me as I mentioned and he was pretty strong so I was in his control the whole time. He continued to fuck me and then started breathing harder. A second later he came inside me. I felt his cock spasm with every spurt of hot cum. That set me off and I spurted my load all over my hand and stomach. Adam stayed inside me for a few minutes and then slowly slid out of my ass. A stream of cum followed and I knew it was a good time to take a break. I freshened up in the shower and then slipped into my speedo or rather one that was the same size and may have been someone else's.
After that second round of sex guys started to head out while a few lingered. Conner and I cuddled on the bed with Adam. I told him he should stay if he didn't have plans. The three of us cleaned up, went out for dinner and made the most of the king sized bed after. Conner flew out a couple days later with the promise of making plans for me to go down soon. Adam now says hi to me at the pool with a giant smile. We have hooked up a few times but soon he too will move away. I'll work on meeting some other speedo hotties as my thirst is constant.