My first time bottoming is kind of similar to a few stories I've seen here. I was a teenager and it was with a friend. We used to just jackoff together. It progressed to me jacking him and him jacking me. Then we eventually both started producing cum. We'd both seen porn so eventually he asks me to put it in my mouth. I give it a try and hes loving it and doesn't last long before he blows his load. I tell him i get to go next. He sucks me off and I think I blew quicker than he did. Eventually he tells me he wants to try fucking. I ask who's gonna go first. He says let me fuck you first. We get the Vaseline from the bathroom and before I know it I'm laying face down and spreading my cheeks for him. He starts to slide it in and finally has all 6 inches in me. He says is it OK. To me this felt amazing. I tell him it feels really good. I get just a few pumps and I hear him groaning. I said what happened? He says I'm cumming. He laid on top of me for a bit and slowly pulls out. I'm just staring wondering how he came so fast. A while later I tell him its my turn. He says ok. He gets in the same position and I slide inside him. I slowly push it all the way in. I'm roughly the same size as him but my cock is a little thicker. He starts whimpering that it hurts. I said now you know how I felt as I start to pump his tight little ass. He's squealing its too much. I said I let you cum, I get to cum too. He says can you slow down it hurts. I slow down for a while and finally feel myself getting ready to cum. I push as deep as I can and start grinding his ass hard. I empty my balls inside him and whisper in his ear, thats mine now. He gives me a bit of a look of confusion and I pull out of him. We fall asleep and continued our little fun just about every time we'd stay at each other's houses. One day his mom walked in on us while I was balls deep inside him. She turned around and shut the door. I finished and we went to face her. We got a long lecture about what we were doing and being safe. She asked if we were a couple. We both laughed and said we were just having fun. After that conversation the next time we had sex I asked if we should be a couple since we do it only with each other. He laughed and said we haven't kissed or anything. I asked him if he wanted to. He said I've wanted to ever since I fucked you the first time. Here we were, teenage boys, making out and getting each other off frequently. What a fun time.
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