First Time Anal with my Teammate

Being on a varsity team had its perks. In some of my classes, I would get a sort of free pass to just attend class and get a passing grade even if I didn't do well enough on my tests. There would also be some students who would try to get on your good side to make themselves seem cooler for hanging out with the jocks, and for some there would even be girls fawning over them. That would be the case for me as well but I was in a school that was for boys only.

I had spent a few years already on the varsity team and I was in my junior year when it happened. It wasn't really a secret on the team that some of the members would sometimes have fun with each other after training in the showers and we didn't really mind as long as our training and our game didn't get affected by it.

I for one didn't mind because I was also part of some of those after training sessions and if it didn't improve our team chemistry, it at least helped with relieving stress after training. I'm not really sure to what extent my other teammates did it like if they did anal but I just stuck to receiving blowjobs from time to time.

During one of our training sessions one of my teammates, Ray, came up to me and told me about how he and one of my close friends on the team actually just had sex yesterday and was asking if I was interested in doing it with him as well. He told me he's had his eye on me for a while now but he didn't really know if I would be down but after doing it with my close friend he figured that I would be more willing now since my friend did it too.

To be honest I kind of got excited by the thought of it but knowing how this game works I needed to make it seem like I wasn't as excited as I was about it.

I scoffed and said to him, "I'll think about it."

The next few days of training went by and Ray would ask me again and again after each training about having sex with him and I would just wave him off. At this point I just wanted to get it over with but I didn't really want to do it in the showers like everybody's done by now so I went over to my close friend and asked him if I could do it at his place in exchange for some favors in the future.

He didn't even mind about the favors and just said, "Just don't make too much of a mess at my place when you do it."

With my friend's permission, I told Ray that we could do it after our next game. He got really excited and told me to make sure to buy some condoms and lube to make sure everything goes smoothly.

Game day came and went by with us winning the game which put the team on a high for the rest of the day.

Me and Ray were celebrating with the team when he sent me a text saying, "Fuck me already."

I looked over and saw Ray with the most slutty look to his eyes and I took that as a good enough sign that we should head over to my friend's place already. We each made our own way out of the group and met up somewhere outside and then we made our way towards my friend's place.

Once inside the room, it was sort of awkward since we didn't really know where to begin. Luckily I brought a joint over and after we smoked a couple of hits from it, we were lying down next to each other when Ray started rubbing my chest and told me to take of my shirt.

We both sat up and he took my shirt off of me and started kissing me. It started off with a few shy pecks which turned into a full on make out session with our tongues dancing with each other.

He started going lower towards my neck with one of his hands caressing my nipple and the other rubbing my crotch. I was already losing myself to the sheer ecstasy of the moment when he suddenly started sucking my nipples, going from one to the other and I could've cum right then and there but Ray had other plans for me.

He went between my legs and he took of my shorts and underwear in one go exposing my now erect 7 inch penis. Ray opened his mouth and stuck out his tongue as he smacked his face with my dick, some of the precum flinging out and sticking to his face. After moaning on my dick for a while, he didn't need any instruction and started taking my cock in his mouth.

He first started slowly bobbing up and down towards a little lower than the head. What he did after was something that I hadn't really experience a whole lot which was a deepthroat. He really took it all the way down to the base in one swift motion and I could feel his throat adjusting to my dickhead poking into it, it almost felt like a massage coiling around my dick.

He would do this and slowly bring my dick back out before slamming himself onto my pubic hair again and again with his slop all over the place. Once he stopped, he showed me my dick covered in his saliva and his face red with tears running down his cheeks. I thought he was going to ask me for a breather but instead while panting and with his saliva drooling down his chest, "Please. Let me ride your big dick."

I tried to reposition myself by lying down and scooching over but Ray took that as a go ahead from me and started taking off his clothes altogether and straddled me right after. He had a cute little penis about 3 inches at most and he was a bit shy about it but said I didn't really mind.

He got one of the condoms I brought which slipped on pretty easily with all the saliva he left on my dick and he opened up a packet of lube which he rubbed all over my dick and some of the leftover on his ass.

He sat down while facing me and put my dick between his ass cheeks then he started grinding on me, I was moaning from the pressure in between the two globes of an ass Ray had and it seemed I wasn't the only enjoying this since Ray was also moaning pretty loudly.

I hadn't really noticed what he was doing but he was actually raising himself up higher and higher while grinding on me until the point my dick was pointing straight into his hole and I felt the pressure from the tightness of his ass slowly enveloping my dick.

"Oh fuck!" I couldn't help myself saying when he sat all the way down on me, which made Ray grunt and say, "Fuck, you're bigger than your friend was."

This got us laughing for a while but soon after our laughs were exchanged with moans between each other as Ray rode my dick, going up and almost slamming himself down on me and he started to pick up his pace. I almost came into the condom but it seemed that Ray sensed this and slowed down before getting of my dick with an audible pop as my dick flopped on my stomach. He told me to stand when he took my dick in hand and slowly started peeling the condom off of me.

I didn't really know what was going on but I just went with it and he started sucking me off again saying, "I felt you were throbbing in me a while ago and I figured you might be going soft after I just cockblocked you from cumming a while ago."

This guy definitely knows how to give a good fuck.

He took my dick all the way down to the base again and making my dick sloppy once again, but this time instead of putting on a condom he stood up as well and said, "I want you to fuck me doggystyle. And I want you to fuck me raw this time."

Before I could say anything he gave me a good kiss with both of our saliva mixing together with a bit of the taste of my dick and turned around while going on all fours, pointing his pussy straight up to me. I rubbed my dick on his asshole and started grinding like how he did with me earlier, slapping his ass every once in a while making him squirm and moan at the same time.

I lined up my dick towards his hole and started slowly poking but not really inserting my dick and said, "You want me to put my raw dick into your hole?"

Ray moaned into the sheets and started pushing against my pokes which made more of my cock to go inside his hole and said, "Pleaseee just fuck me already, I want to feel you raw inside me."

With him pushing back at me, the head slowly popped in and it felt so different than having a condom on. We both had our movement synchronized and inch by inch my cock slowly made its way all the way into his ass, burying myself with our balls touching.

We both let out soft moans and I started kissing his neck all the way down his back which made him arch his back even more and making a vice grip on my dick. I started to pull out and almost like he was chasing my penis back into his hole, Ray was also trying to push it back in.

I picked up my pace and with it how powerful I was smacking into his ass. The room was filled with sounds of bodies slapping against each other met with our moans each time we bottom out.

After a while I was almost at my limit so I asked Ray, "Where do you want my cum?"

Ray went silent for a minute and decided, "I want you to cum in my mouth, I want to taste you and swallow your bid load."

The dirty talk almost sent me over the edge so I pulled and practically dragged Ray off the bed sitting him on the floor with his head lying on the edge of the bed. He opened his mouth as I jacked off in front of him, from time to time putting the head of my penis on his tongue where he would lick the underside while moaning.

Soon, spurt after spurt of cum came out of me and slowly started filling his mouth with my white gooey sperm. Before he swallowed, he showed me just how much cum I filled his mouth with and with a smile he gulped down on the cum in one go and showed me clean mouth with a few streaks of white hanging off his teeth.

He gave my dick a few more strokes and cleaned up the remaining cum. We cleaned up the room and took a nice steamy shower after where we made out and I got to taste my own sweet but slightly salty cum which made my dick hard again. He offered to suck me off again since I got hard which I didn't decline. I ended up cumming on his face again after that and after freshening up again, we said our goodbyes and headed home.

Thanks for reading this story, this was a true story that happened when I was younger and I just wanted to share this hot experience with everyone. I'll be writing more of my experiences soon, not only with gays but with transsexuals too.