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- When I Was A Kid -
Bi-Sexual Male / 56

A Pencil And Vaseline

I started being very sexually curious when I was maybe 5 or so. By “sexually” curious I mean playing with myself both anally and genitally. I had no concept of sex or sexuality, and I wasn’t ejaculating of course, I just knew those waves of pleasure felt good.

When I was seven I discovered that putting a dab of vaseline on the eraser end of a pencil and sliding it in my ass felt amazing. I did it often. I started introducing friends (boys and girls) to my anal pleasure secrets aling with mutual body exploration. Some liked it, some didn’t.

By the time I was 9 I had experimented with a variety of objects up my ass and my awareness of sexuality had greatly increased. I was probaby 13 when I first thought of and wanted a boy’s cock up my ass. But it would be another 13 years before that would happen with 40 year old Jack when I was 26.

My wife knows all about that history and my still strong desire for anal pleasure. She knows I’m bi and genuinely enjoy sex with her and occasionally with men. When I am with a man (or with my wife using a strapon) I am 100% submissive. She actually suggested I may have been anally m****ted at a vey young age and that triggered my curiosity and experimentation with others. I have no recollection of any m****tation and have no negative feelings around sex or anal play. I just think for whatever reason I’ve always enjoyed and wanted anal penetration. I still enjoy taking something up my ass, except now it’s a hard pounding ejaculating cock rather than a pencil with vaseline.

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# 81296 - by Kendrick / August 8, 2025
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Comments

Anonymous

by Anonymous on Aug 8, 2025 at 7:06 AM

Eraser up your ass. You trying to erase your hemeroids. Keep on a running.

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Anonymous

by Anonymous on Aug 9, 2025 at 2:27 PM

What’s with all the sexually frustrated weirdos on here who hate on everyone. I mean it’s a sex confession website for gods sake. And that is why we are here confessing and they are here reading this stuff…they get off on it. But then they act all critical and superior.

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Anonymous

by Anonymous on Aug 11, 2025 at 6:20 AM

As a young boy I experienced the very same things as you did. I still don’t know why but when I was 6 or 7 I discovered anal pleasures myself. First it was my finger in my ass in the shower while I played with my hard little cock.
After awhile the finger wasn’t enough so I would take different things into the shower and put them in my ass then leave them in while I showered. One day I discovered the bathroom plunger handle. I stuck it to the shower floor spread my ass cheeks lowered my ass lined the end of the handle up to my young tight asshole and slowly lowered myself down until it went in then I slowly went down until it was way up inside of me. I was going crazy with this feeling of having something so far up inside of me. I started pulling on my cock and working my ass up and down and I was fucking myself and it felt great.
I started going down in the woods to a couple of places I knew where it was very private and I could take off my clothes and play with my ass and not get caught. I figured out that cooking oil was really good to use to make my hot little hole nice and slick to insert things up my ass.
I looked for anything I could find to stick in my ass and I would spend a lot of time in the woods with things stuck up my ass. After the longest time of playing with my ass and learning how to fuck myself I just had to find out if other boys were doing this same thing so one day when my best friend was at my house we went down to the woods just to run around and hang out like always. I slowly started to hint around about playing with myself and once he figured out it was Ok to talk about it with me we started to have a conversation and when I asked him if he ever tried to stick anything in his butt. He said no and he never thought about it. I told him I liked doing it and I do it every day if I can. He didn’t believe me at first but once he knew I was telling the truth he asked me if I would show him what I was doing. I really didn’t want to let him see me doing it at first but he kept asking me until I told him OK but he could never tell anyone if I did it in front of him. It took me awhile to talk myself into letting him watch but once I was naked from the waist down it got easier as I let him watch me put some cooking oil on my fingers then stick them in my ass. I noticed him reaching for his crotch as he watched me finger my hole then when I took out the fat magic marker that I used often he was right behind me and watched as it went in my ass and I pushed it up inside of me until just the cap was sticking out of my ass.
He started to breath heavier and when I looked over my shoulder he had his hand down in his pants rubbing his cock. I asked him if he was OK and he said sure and he liked watching me. I started to work the long fat marker in and out of my asshole and he got excited and I told him if you want to drop you pants go ahead. In a few minutes he also was naked from the waist down and was jacking off watching me fuck myself.
I guess he got excited and I felt him touching his dick to my ass cheeks and he was rubbing his dick all over my ass then pushed my hand away and now he was fucking my ass with the marker. Now we were both jacking off and neither of us could shoot and cum yet but the sensation was there and once we both had a dry cum he never took his hand off the marker in my ass.
After we both calmed down he asked if I really liked having that market up my add and I told him it felt great. He smiled at me and then asked me if he could try doing it to me with his dick. I told him yes very quickly and as soon as he was hard again he took the marker out and easily slipped his dick up my ass. We both liked the way it felt and he started to work it in and out and then he grabbed my hips and started to fuck my ass and it felt great. Later both of us had that mind blowing sensation with his dick stuck up my ass. We stayed there long enough for him to put it up my ass again and he fucked me until we both got off again.
From that day on almost every day he and I met some where so he could put his dick in me. Months passed and then one day he had an older cousin come stay a couple of weeks with him for the summer and he wanted his cousin to have fun with us in the woods. I agreed to letting his cousin join us and once we were in the woods and had our clothes off I was amazed at the size of his cousins dick. He was three years older than us and his dick was very large.
I never really considered sucking a dick but while he stood by watching his cousin fuck me he put that big dick in my mouth. I started to suck on it and as soon as his cousin pulled out of my ass he hurried around behind me and started to put his big dick up my ass. I had never taken anything that big up my ass and by the time he had it all the way up inside of me I wanted to scream out loud. He knew what to do and by the time he was fucking me really hard I was on my belly in the grass with him on top of me and he never tried to pull out and he shot my ass full of warm cum and from that minute on I was hooked on his big dick and wanted him to cum in me numerous times a day and for two weeks he fucked me as much as he could and then he went back home and I thought about his dick every day.
All thru my school years online different boys fuck me and some only once and others came back many times. Now in my 60’s I still enjoy a big hard cock up my ass but it doesn’t happen often. All these years anal penetration and a good fuck up the ass still feels good. My wife doesn’t know but over the years we have played around with toys and even bought a couple of strap on cocks for her because she said it was her fantasy to try strap on sex with a man. We don’t do that very often now days but when she is in the mood to fuck my ass I never say no.

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Anonymous

by Anonymous on Aug 11, 2025 at 1:26 PM

It started like that for me and after using several different things in my ass I just had to ask my best friend if he did the same thing. After we talked a while he convinced me that he never stick anything up his ass but then he offered to help
Me out and said he wanted to put his dick in me. He looked shocked when I agreed to let him try it We were only 12 at the time and at his house alone so he got me to step out of my pants and take down my underwear then bend over the side of his bed and he got his dick in my ass and once we both got used to it he fucked me and shot his tiny load in my ass
We had plenty of time so we both got naked and this time I was face down on the carpet and he was on top of me and he fucked me really good and came in my ass again. I didn’t want him to take his dick out of me and every day when we could I let him fuck me and that went on for years and I met other boys fuck me back then and more than once I had several boys taking turns on my ass down in the woods. I had a lot of fun growing up.

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