My Neighbor

Growing up there was a boy Nextdoor about my age. We were in the 2nd grade. Where we lived there was a crack and a wooded area across the street. He and I played there every day.
We built this fort out of old lumber and tree limbs and we hung out there every day working on it and just playing in the woods.
One day we were in our fort and I asked him if he ever played with his self. Because sure then I asked if he wanted to do it with me. At first he didn’t want to but once my pants and underwear were down and I was playing with my dick he did the same. We were sitting next to each other leaned up against the wall of our fort watching each other and I put my hand on his dick. He moved his hand and he let me stroke his dick.
I liked doing it and was stroking mine at the same time. Next thing I did was lean over and lick the end of his dick. He let out a gasp and flexed his hips and his dick was in my mouth. I put it in and took it out several times then left it in my mouth and was sucking on it man did he enjoy it and he kept pushing my head down moaning out loud. He said he liked it a few times then he shook all over and got real stiff. He was too young to cum but it felt good anyway.
After about an hour of running thru the woods he asked me if I would do it again. We were in a good spot in the woods where no one could see us so I told him to take down his pants and I got to my knees and sucked his dick again. This time felt much better as I had my hands on his bare ass and he was holding my head
Every day after that we went to our fort so I could suck his dick. He started sucking mine after a couple of weeks and we would go to our fort and 69 after school.
He and I played around sucking each other off and he liked to play with my must and asshole. In the 5th grade I let him put his dick up my ass. He fucked me and came in my ass twice that day.
The next day I asked him to do it to me again so after school at his house with no one there but us he and I took off all our clothes and I bent over the side of his bed and he fucked me from behind and came in my ass. We had lots of time so we went into their living room and with me on my hands and knees he fucked me again and came up my asshole.
Everyday after school he fucked me in the ass at least once if not two or three times. In the 8th grade we had two other boys join us and we had sex with them too. Eventually all 3 of them fucked me and once that started it went on for years even after we were out of high school.
I remember everything that we did back then and I still like to jack off thinking about it and I am
Married now but think it would be nice to get my ass fucked again someday.

Comments

Anonymous

by Anonymous on Jul 3, 2024 at 8:55 AM

I started hanging out and played with an older really sissy boy when I was in 3rd grade. I emulated him and his girlie looks and enjoyed wearing my two sisters panties under my shorts not realizing that they showed and attracted attention. Even though he was very feminine he took on a masculine role teaching me how cuddle and suck. He was a bottom for a guy in his mid twenties and popped my cherry when I was in 4th grade. It became quite fun for me and him making it with me with both of us in various degrees of dressing as girls. Both of us were quite cute and nobody questioned that we weren't girls.

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Anonymous

by Anonymous on Jul 3, 2024 at 3:31 PM

You can ask your wife to peg you.

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Anonymous

by Anonymous on Jul 11, 2024 at 5:39 PM

We dont own a proper pegging toy but I surely get dildoed often enough … not everytime because of kids but my wife is good enough to carry some toys when we go out so that I can get penetrated too. I probably would be willing to have a bisexual threesome but she probably not… but she knows I do like dick, specially a friend of us who is well endowed… getting that fantasy to reality would be great, I have come so many times with it :)

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Anonymous

by Anonymous on Jun 19, 2025 at 5:09 PM

I am divorced and by and can tell you there are lots and lots of guys that are in exactly the same position as you. There are a lot of apps and sites where you can find guys that are just looking to hook up. I found one guy that was offering massages for people in shape with no strings attached. I thought it was scammy but whenever anyway. He gave me a great massage and we ended up hooking up. I've been seeing him every few weeks for about 5 years now and we always have a great time. He's married

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