Sleepover with My Best Friend

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1 likes 9121 views Category: Male-Male Tags: friend, first time, stroke, blowjob, Stepmom kitchen, truth or dare


This happened when I was 13. One night my best friend Jake, and some of my other friends had a sleepover. During that day before the sleepover Jake showed up early before anyone else and so we spent the whole day swimming in my pool, after a while Jake went to get out of the pool and the weight of the water pulled down his swim trunks, revealing to me, which actually was, his really cute butt. Now I'm not gay or anything and I would never think of doing anything like that with other boys, but his butt actually got me REALLY hard, I would never tell that to him and risk our friendship, so I just said "Nice butt, Jake" to which he replied, "Shutup you", then he pulled up his trunks and went in the house.

Later that night when all my other friends arrived and the sleepover was under way while we were all watching a movie and eating pizza in the living room, Jake whispered to me that he wanted to talk in private, so I brought him to my room upstairs and locked the door. He started to talk and he just straight out said, "I've been reading all over the internet about masturbation and really want to try it, but I'm scared", I then said "Jake don't worry about that, I've been doing that for over two years now, if you want to do it, then do it, I promise nothing bad will happen to you, I'm sure you'll actually enjoy it." But Jake said he wanted me to help him out so I promised that we could meet in the bathroom at about 12:30 in the morning when everyone else was asleep and I'd show him how to jack off.

It was 12:30 and I was waiting in the bathroom for Jake to come, after about 5 minutes of waiting the doorknob turned and in came Jake, and he said "I'm ready," I said "Ok Jake the first thing you have to do is get naked," Jake then said "I'm too nervous to take my clothes off, will you do it for me?". I said "Of course I will Jake", then I went over to him and gave him a big best friend hug and started to pull his shirt off. After that I told him to lay down on the floor and I started to slowly rub his tummy, I could see that there was a huge bulge growing in his pants, so I asked him if he liked that and he said "Yes, very much", next I started to slowly undo his belt and pull his pants down leaving him in his little tiny tighty whities with his HUGE bulge sticking out of them, Jake looked down at it and asked me what thing was, I said "That's your erection Jake, pretty soon I'm going to start playing with it and it will make you feel very good", he just smiled after that, and by that point I was fully erect myself and I stripped myself down to my underwear, then I went to lay on top of Jake and I started grasping his butt and tummy and erection, and he started to moan in ecstasy, that put me over the edge and so I just pulled his underwear down and grabbed his penis and told him he was going to love this.

I started to stroke him and he started almost crying in pleasure, so I then massaged his nipples and even fingered his butt hole to stimulate his prostate and then he started breathing really heavy and I knew he was about to blow. So I stopped completely and told him "I want to make this extra special for you Jake", so I inserted his penis into my mouth and finished him off and swallowed his load, and he literally started to cry, so I started hugging him and kissing him and I told him that I loved him so much, and after a while he was ok. Once he was calmed down I asked him if he would do it to me and he said sure, so he stripped down and laid me on the floor and started making out with me, then he started to stroke me and massage my nipples and finger my butthole, and then when I was about to cum he gave me a blowjob and swallowed my load just like I did to him.

We then fell asleep in each other's arms in the bathroom and woke up in the morning and started saying how much we loved each other, then we both agreed that we have to have more fun times like this in the future, and we have, many times. Well that is my story, and please note that I am NOT gay, that was just being with my best friend and helping him uncover the wonderful world of masturbation, I have a girlfriend that I regularly do "stuff" with, so please know that I'm not gay. Thank you.



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