When what I thought couldn't happen did Part II

Posted in: Ass Play

I am so proud of myself for using the disclaimer as requested by the host because it is the respectful thing to do.

Part I left off with the kid leaving my work with out telling me. I am closing up shop, hard and horny to the max and looking forward to a multiple jerk off session with myself.

I get home and I realize how tired I am. I decide to not only strip and jerk off but to take a nap so I will be rested for the partying to come that Saturday night. I end up in my bed, I get lazy and roll over and shoot on the sheets so I don’t have to clean myself up. I love the smell of cum and I lay there looking at the pool of it on the sheets. I keep a hold on my cock and close my eyes remembering what I think I saw with the kid at work today. I get off as I imagine him shooting deep in my mouth. I fantasize that after he gets off he asks me to not stop, tells me he loved it so much he wants to cum again. As I am stroking thinking I’ll shoot a third time, I drift off to sleep.

I wake up around 8 p.m. and am sort of unsure about the day, if it was real or a dream. I yank the covers off and smell the cum and then see the sheet loaded with my dry cum. All I know then is that whatever my day was like, real or fantasy, that it has me hot to the max. I shower and start to wake up. I realize we are going to party at my friends house tonight and I get all happy and hope his neighbor boy is able to sneak over to say hello. I’ll call the boy Jimmy but that is not his real name.

I get to my friends and I make sure I am heavy on the gas so the side pipes of the Vette roar loud. I want Jimmy to know I am there thinking if what I think happened at work was real, he’d find a way to say hello to me. I bounce out of the car and over to the picnic tables, I am later than the rest of the guys, they already have a buzz on. The get on my case for making so much noise and say I should have just called the neighbors and told them that we were smoking herb and drinking. I tell them to shut up and if they want a real care like I have they should go get one.

I look for the kid but don’t see him, I right away feel down for even thinking the whole thing is real. I toke up, grab a cold brew and settle back to get myself numb. Before I know it Jimmy is saying hello to my friend and some of the other guys. I act cool but am hoping he doesn’t ignore me. Eventually he gets to me and says hello and hopes I am not still mad at him for bugging me at work earlier that day.

I say I was never mad at him, I was just hung over and mad at myself for how I acted the night before. He says he is so happy to hear that and flashes me that smile of his. I ask what made him decide to visit me at work and asked how he got there. He said he was working out and just thought he’d bike over to see what kind of mechanic work I was doing.

I said that was cool and then asked why he left and didn’t say he was leaving. He said, well, I figured you were mad at me for being there, and well, I just figured I should leave and hoped you didn’t notice. I laughed and told him that I would think he would want me to notice him leave since he left cause he thought I was mad. So he says it was something beside him leaving he hoped I wouldn’t notice, then he smiles and looks right at me.

Soon after he said his good byes and went back to his house.

The day ends, the week passes, and Saturday I am working the garage again. As I was secretly hoping for Jimmy shows up and repeats the show like the Saturday before. This time I just take it in and I make it a point to adjust my stuff in my crotch when I see him looking. We say nothing about being horny or being curious or wanting sex. That night I go to pick up my friend, he was older than me and was going to buy some booze at the liquor store for us to drink a little and cruise around. Just as he gets to my car the kid Jimmy comes bounding over from his house. He says he wished three people could fit in the car. Then he says my friends doesn’t have as big as a console as mine and maybe he could sit in the middle. My friend says it would be really uncomfortable and Jimmy says he doesn’t care he just wants to go for a ride.

I lock my car up and we end up sqeezing into my friends car. Jimmy is in the middle with his legs swung over on my side. We are sitting so near each other that I can feel the heat from his body. After we are on are way for a few minutes I notice him shifting his weight around and his legs are getting closer and closer to mine. I have no doubt since we were so close to begin with, then the next bump we hit has Jimmy moving and landing with his right leg full against my left leg. I don’t move at all and neither does he, we both just look straight ahead. Then he ask if he can put his arm behind my seat cause he is cramped and I say for sure. So he does and says that is much better. Then I feel his arm brushing against my upper back and then he rests it there. Neither of us is moving away or acting uncomfortable at all. Then I feel his hand touching my back until he is running it up and down my spine. I scoot a little forward and he knows I am not pulling away but that I am making it possible for him to put his hand lower, like to the waist band of my briefs. And he does and leaves his hand there. I decide to shift around and put my arm behind him. He notices and leans back into my hand. I move my hand down his back directly to his waist line and I fiddle with the waist line of his jeans until he pushes harder against my leg with his leg. Then I take the plunge and put my hand down his pants and rest it as low on his ass as I can. I see that I was right about the kid wearing no briefs and I am excited about what we are doing. Never a word spoken but there we were, each of knowing what we wanted, and my hand is on his ass and his low on my back inside my pants, and we are in the car with my friend driving. We get to the liquor store and my friend says we need to wait in the car since we are underage to buy booze. We say that is fine, of course we think it is fine. When my friend goes in the store I want to move my hand from the kids ass to his crotch and feel if his cock is as big and hard as I pictured it was. But I didn’t. The kid moved his hand around on my back and I moved my hand on his ass. That’s how we drove back to my friends house too.

We decided to hang out under the trees in his back yard and drink a little. Jimmy stayed with us so I asked him if he would get in trouble for hanging out with us. He said he was free cause his parents went to a party so he could stay out. As we passed the bottle around Jimmy got between us grabbed the bottle and took a drink. We included him in the pass of the bottle after that and he drank as much as we did. We were all pretty tipsy and my friend said he was going to call it night and went in leaving Jimmy and me alone outside. I was trying to figure out the best next move to get his cock out of his pants when he asked me if I knew a place we could go. He said he could stay out but felt weird just standing in my friends back yard.

My parents were out of town like they usually were so I said we could go to my house if he wanted to. He asked if we’d be alone and I said yes so he said that he wanted to go there. We drove to my place but didn’t touch each other or say anything. When we got inside I sat in the living room but Jimmy said he was sort of drunk and asked if we could go to my bedroom so he could lay down, if it was okay with me for him to lay on my bed. I said I was fine with that as long as he wasn’t going to puke. He laughed and said he just wanted to lay down so we went to my room and he got right on the bed.

I stood there not sure of what to do but then he asked if I had any Playboy magazines so I got one of my Dad’s and gave it to him. He propped himself up on his side and paged through the Playboy and like squirmed his crotch and ass around like he was trying to shift his cock around. I looked over his shoulder and said I didn
‘t know about him but the Playboy had me hard and that
I really got turned on sitting next to him in the car. He said he was hard too and in the car he wished we were alone because it turned him on too.

He rolled onto his back and pointed to his crotch and said he was so hard it kind of hurt cause he had no underwear on so his hard on was against the rough jeans. I said he could take his pants off and be more comfortable if he wanted to. Then I showed him the tent in my pants and we laughed. He got up and stripped and I could see how big and hard his cock was. I was smiling inside thinking about the great suck I would be giving him real soon. He got back on the bed on his side and was facing away from me.

I was about to scramble onto the bed and take his cock in my mouth when he rolled more on his stomach with his ass right in front of me. I had never fucked or been fucked, never even touched an asshole before. I froze not knowing what to do and just looked at his ass. He spread his legs then reached behind his back with both hands and spread his ass cheeks exposing his smooth pink hole. He pushed his ass up towards me and whispered to me that he wanted me to fuck him. I asked if he was sure and he said yes, I stripped completely and moved my cock towards his ass.

Once I was in a good position I held my cock in my hand and pressed my wet cock head against is asshole. As soon as I did he pushed back and wrapped his asshole around my cock. The sight of it was so hot, and it was my first time with my cock up a guys ass and that excited me. He moved in rythm with my in and out strokes and fucked like he knew how to. He moaned and groaned and lifted off the bed more and more until his cock was in plain sight. Seeing his cock dripping with pre cum had me thinking about how great he would be to suck after I shot in his ass. I came and pumped and pumped as he squeezed his asshole tighter around my cock.

I still prefer sucking to fucking, and I have yet to get my ass fucked, but I am glad that my first time fucking a guy happened the way it did. I was sure nothing could happen but more than I ever imagined ended up happening for real. After that when a guy around Jimmy’s age seemed to be coming on to me, I believed it and took what life was offering.

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