Jay and I went to breakfast as though nothing had occurred earlier this morning. While we were eating, two other guys approached and sat down at our table and began talking with Jay as though they were old friends. Jay introduced them to me as Mark and Tim, and that they were old friends in which they used to play on the same team. I didn’t think anything about it as they all chatted and were talking about it being half time Mark then commented to Jay, almost asking “double or nothing?” Jay looked down at his meal and then raised his head looking at Mark saying nope. “Okay then, we’ll see you guys later” Mark said giggling as he and Tim got up walked away.
Puzzled, I asked Jay what that was about, in which he replied that it’s just a game that they used to play. Jay suddenly stood up, said he had to get to class, and walked away. I thought it was a bit odd, but figured he must have something going on in one of his classes and just spaced it off.
I finished my classes at the end of the afternoon with everyone else, and headed to my area to clean. I hated it when people hung around and felt a bit embarrassed when others would see me cleaning, but I guess it made me money, so you just put it in the back of your mind. I started with the sweeping the classrooms as I hated cleaning the restroom. Finally, all the classrooms were done and I headed to the restrooms. I did the girls first as it seemed like they weren’t as bad. Once they were finished, I went to the mens and as usual, somebody always seems to plug up one of the toilets, and nobody seems to be able to keep from peeing on the floor around the urinals.
As I got to the last stall, I heard somebody walk in the restroom. I payed no attention and just tried to finish without being noticed. As I was bent over cleaning around the back of the toilet, I felt as though somebody was behind me. I looked over my shoulder and saw Jay standing behind me smiling. “Cute butt” Jay said as he was obviously staring at my butt. I wiggled it and laughed, and continued with my cleaning.
I then felt a hand on my lower back pushing me down further as his other hand began to rub the side of my butt. I wiggled my ass again teasing jay, but then he began to rub the outside of my ass through my jeans. Jay then pressed the front of his pants against my butt. I could feel his hard cock pushing up between the cheeks of my ass and found myself grinding my ass harder into his cock. Jay then reached around tot he front of my jeans and undid my belt, then the snap, and finally lowered the my zipper.
Jay then grabbed the sides of pants and boxers and pulled them down to my ankles. Bent over saw far, I could now fell the cool air now hitting my exposed asshole, as I knew my cheeks must have separated being bent over so far. Jay then reached for my hard cock and began to slowly stroke it, while his other hand grabbed my balls. After a short time, he let go of my balls and began to run his finger over my asshole while he slowly pumped my hard cock. I reached back with my hand and managed to get his pants undone and pulled his cock out. I found myself only able to reach it with one hand, but as soon as I got a hold of it, I began to pump it as though their was no tomorrow.
Jay then let go of my cock and grabbed my hand stopping me telling me to slow down. He then pushed the end of his cock against my tight asshole which concerned me as I had never had sex anally. Yet, at his time, I felt that if it was going to happen, and felt I could trust Jay with deflowering my ass and doing it without hurting me. I then heard the slurp that I assumed was a squeeze bottle of lubricant and felt the coolness of it being applied to my asshole. Jay then put his cock to my virgin hole and began to push. “Slowly please.” I commented as Jay pushed. I felt the pain of my little hole refusing to open as Jay just kept pressure on my tight little hole. Jay then pulled his cock back and gently pushed a finger in my ass. I worked then in and out which actually felt good. He then pushed in another finger adding more lube and pushing it into my ass. Jay then put his cock to my asshole again, and began to push.
Suddenly, I hear the sounds of footsteps coming in the restroom causing me to stand up straight. Jay mutters “dammit” as I turn around facing him smiling. Jay looks disappointed as I placed my fingers to my lips to keep us from saying anything. We hear the person take a stall near the other of the room in which you can hear him set down and begin to make the sounds of him relieving himself. I pull up my pants and squeeze between Jay and the wall exiting the stall.
I look back at Jay who is still standing there with his cock now hanging limp and waive him to come along. As we exit the restroom, I’m laughing yet Jay looks frustrated. Looking back, I joking tell Jay that I guess I’m keeping my anal virginity for another day. But I’m sure I can make it to him. As we walk down the hall, I feel the lube still in on my asshole and butt which makes my cock harden in the sensation.
Jay and I then go to the cafeteria to get dinner. I talked quite a bit, but Jay seemed to have his mind elsewhere as he just fumbled with his food and didn’t tell his normal stories of conquest. After dinner, we went back to our dorm room which we both flopped on to our own beds. “Look, I need to tell you something.” Jay said. I looked over at him in which he had a serious look on his face. At this same time, the sound of someone knocking at our door interrupts our discussion.
I open the door and am met by Mark and Tim. “You mind if we come in?” Mark asked. “No problem” I reply in which they walk by me entering our room and go to where Jay is lying on his bed. “So?” Tim asked. Jay looks at the ground and says ‘I lost”. Tim then pulls out his cell phone and turns on the video camera. Once it’s on, he hands it to me and tells me to record this. I look at Jay confused as he just shakes his heads yes.
Jay gets off his bed and then removes his shirt, kicks off his shoes, and slowly removes his socks. I’m standing there not sure what is going on when Mark reminds me to keep the camera on Jay. I aim the camera at Jay as he unfastens his jeans and allows them to fall to the ground and then finally, he drops his boxers. I keep the camera focused on Jay who looks nervous as he is no longer smiling and even his cock that normally hangs from his body seems to be hiding as well. As he stands in front of us, his limp cock is hidden by his foreskin, yet it’s glistening from the lube earlier and has a little string of precum hanging off the end.
At this time, Mark pulls out a quarter from his pocket and flips it in the air. It falls to the ground tails up. Tim then reaches over and picks up the quarter and again flips it in the air and this time, it lands heads side up. “Cool!” Tim says. Jay then walks to where Tim is standing and unfastens Tims pants. He grabs the side of his pants and underwear and pull them down as one leaving Tim exposed. Tim’s cock and balls were shaved, and he was semi rigid as he stood there. It wasn’t much bigger than ours and was circumcised. Jay bent over and took Tim’s cock in his mouth and began to slide his cock in and out of his mouth.
Meanwhile, Mark had slid his pants and underwear down and was now standing behind Jay with his cock in his hand sliding lube on it. His cock was hard, probably seven inches in length, and the width of a pop can. Mark reaches towards Jay’s ass and begins to spread lube in and around it. “You’re going to want all of this” Mark says. I get closer to where Mark was standing, in which Mark grabbed my hand holding the camera and put it near Jay’s asshole. Mark then put his cock at his ass against his little hole, making me shudder wondering if he really thought that it would go in such a tight hole.
“Push yourself on it” Mark says. Jay then began to push back onto Marks cock. As he pushed, I could see the muscles clinching at first, but slowly, the tip began to push his little hole open. Jay began to say something, but Tim just pushed his cock further into his mouth stopping anything except the sound of his cock fucking his throat. Jay continued to push back keeping his hands on his knees as he rocked back and forth from Tim’s fucking, each time, sliding a little bit further onto Marks huge cock. Suddenly, Jay slid all the way back taking Marks cock fully in. As I look at the ring of Jays’ ring, it looked like it would tear if anything any bigger was in it. Mark and Tim then began to piston back and forth with Jay sliding in the middle.
Knock knock I hear again. “Let them In” Mark says. I look at Jay who makes eye contact in which he gives me a thumbs up. I go to the door and open it just a bit not exposing what is going on behind me. “Hi Chris” the first one says as he walks past me pushing the door wide open. He is followed by a black friend who smiles me saying “Looks like we’re just in time”.
“Keep recording” Mark says sternly in which I now see that Jay is just a piece of meat between two lions, each pulling Jay harder and harder onto their cocks. Mark then tells me to stroke Jay’s cock with my free hand. I grab it in which he is now hard and still lubed from earlier. I begin to stroke it in time with Mark’s fucking. “I’m cumming” Mark loudly says. In which I kept the camera on Jay’s ass as Mark’s cock slammed in one last time impaling Jay with no mercy. Jay’s cock suddenly spasms spurting string after string of cum. At this same time, Tim pushed against Jay’s mouth holding Jay spit roasted between the two. Seeing this, I know Tim is loading his cum into Jay’s mouth. Mark pulls his cock out of Jay’s ass with a cum and lube string hanging between. I move the camera to where it is looking up into his hole that remained open. Cum began to leak out and down across the underside of his balls.
Tim pulled out, in which Jay stood up, wiping his mouth with his arm. “Not a drop spilled” Jay said as he smiled at me. As Jay stood, he had his legs spread just a bit in which you could still see more cum and lube leaking out of his ass onto the floor.
“Let’s get this done” Jay said looking at the other two. The first one flipped the coin in which it lands tails again, and the black friend, flipped the coin, with it landing on heads. Jay walked up between the two and began to unfasten his pants. “Glad Tyrone didn’t get tails!” Jay said as he pulled out Tyrone’s cock. I’m sure my jaw dropped as I had never seen anything this big before. Jay began to work his cock into his mouth as Mark introduces AJ. AJ then drops his pants and underwear, lubes up his cock and quickly, without warning, slams his cock into Jay’s upturn ass. Jay lets out a grunt as AJ pounds Jay’s butt hole. AJ didn’t last just a couple of minutes when he burst out that he was cumming and with that, he pulled out and shot cum all over Jay’s ass. Tyrone, on the other hand, just kept working Jay’s mouth trying to push more and more of his mammoth cock down his throat. Tyrone then comment s that he is cumming as well, and with a final push, he unloads his cum straight into Jay’s stomach.
With everyone finished, I shut off the camera and looked at Jay as he stood naked in front of us. His eyes were bloodshot and watery in which you could see that at some point, he must have had tears gong down his face. His legs are slightly spread with his a cum lube mixture still falling from his gaping ass. “You gonna explain this to him?” Mark asks. Jay then looks at me and says “It’s all part of the game. Sometimes you win, sometimes you lose.”