My parents got divorced when I was in the fourth grade, which was the first grade of the boarding school. I was sent to a boys boarding school. The room I slept in had one other boy. All the boys on the floor used a bathroom/shower room at the end of the hall.

On our floor there were boys from the fourth grade to the eighth grade. The boy who slept next to me was in the seventh grade and he liked to masturbate. He took me over and I had to make his bed and clean his area of the room. In the shower he had me dry his penis. To dry his penis he had a special towel. He would masturbate behind the education building and I would go with him while he whacked off. He would whack me off too, getting me to have an erection and when I was good and hard he would bend over and suck my penis. One day he had me suck his penis.


One night after lights out he came over to my bed and put his hand under me and held my penis while I dry humped the bed. I slept on my cum that night. Other nights he would work his penis into an erection and he called me over to suck him. I loved sucking him, I liked the way his penis felt in my mouth. A couple of times he came and he caught me by surprise. I liked the taste of his cum, but I didn't know to keep his penis in my mouth when he came.

One night, he was sucking me on my bed when the assistant headmaster opened the door. He saw us and pulled he door closed and stood outside and watched us. He would come by and stand with our door a little open and watch. We knew he was there and my roommate told me that he liked boys so if he ever asked me to suck him to go ahead.

The following year I got another roommate and he was not willing to let me suck him. On this one night, it was long after lights out and the assistant headmaster came into the room. My new roommate was asleep and he sat on the side of my bed and put his hand under the covers and rubbed my butt. His middle finger slipped inside my butt crack and he fingered my hole through my underwear.

The next day he told me that he needed help with some work and if I would help him. He had me come to his office and stand beside his desk and he played with my penis while I stood leaning on the desk with my legs a little open. When he told me I could leave he rubbed my butt and poked me with his finger. When he wanted to feel me he would ask me to come to his office.

One afternoon I was in the boys' restroom during class and he walked in and stood beside me and pulled out his penis and peed. He held his penis for me, showing me, he asked me if I wanted to touch him. His penis was warm and it felt good in my hand. The next day in his office he opened his pants and let me reach down and play with his penis.

Our visits lasted all year. On the day I was going home for the summer break he came to my room to help me pack. My roommate was already gone and he sucked my penis and he asked me if I wanted to suck his penis. He wasn't at all like my roommate from my first year. His penis was bigger and I would put my mouth all over the top of it but I couldn't get much of it into my mouth. He didn't care, he wasn't there for that. The door was locked, and he told me he wanted to make sure I thought about him during vacation.

He lowered my pants and I too them off and he asked me to lie on the bed and he got on my back. He used some Vaseline and rubbed it on me and then he began to insert his penis in me. It didn't hurt, it felt good and he slowly pushed it in. After he was done and had pulled his penis out he sent me to the bathroom to wipe myself clean. My butt hole felt tender but touching it felt good.

I didn't return to boarding school for the sixth grade, I went back to normal school. It wasn't until I went to boot camp that I slept with other boys again, and I was caught staring at a guy's penis. I got beat up, but I also got fucked and getting fucked was worth it. Somehow I was deployed to Germany and I was there for three years. During my term in Germany I fucked with this corporal that worked as a clerk in the personnel section.

When I left the army I went to college and spent my career as an accountant working for various companies. I am retired now and I have a friend I met at the club. Like me he is a lifelong queer, we are both really more passive than active queers, but together we find it acceptable to take on the dominant role from time to time.

Comments

Anonymous

by Anonymous on Oct 6, 2017 at 10:29 AM

I went to boarding school too. Only in my case I was in the 7th grade when upper class men started using my ass for their pleasure. At first I hated it but I got used to it.

The first time it kinda took me by surprise. I heard stories but didn't know if it was true. I was sleeping one night when the door open. Me and my roommate at the time looked at two of the older guys that came in. Of course we were just sleeping in just our briefs. They said don't worry, every guy does this it's tradition. They had each both of us stand up and lay over our beds. They pulled our underwear down, put Vaseline on our holes and in their dicks went into our asses. My roommate gave quite a loud moan when the guy went in his ass. After they were done we got cleaned up and boy were our asses sore! A few nights later the guys returned and once again we got our asses fucked. By the third week of this we got used to it. Some nights it'd just be either him or me getting fucked so one of us would just sleep while the other took a guys load in our ass.

Upon returning to school after summer break, I was in the 8th grade now, had a different roommate and he asked me first if I got fucked last year too. Well the first night their here comes two guys in so we both got fucked that night.

I got fucked until I was a senior, I never got fucked that school year. By that time I couldn't tell you how many dicks or loads I took up my ass. It was a lot. I do know my 9th grade year there was this one guy I heard two others my age talk about. They said everyone is praying they don't have him walk in their room at night. Well just my luck he came to my room that night. I found out why they didn't want him. He took his pants off and his cockmust had been 9” and thick! I about shit and thought well there goes my tight asshole. Up until that point I had it easy I guess but boy was his hard to take. I guess I was unlucky because he only fucked me that school year. I'm surprised my asshole still functioned normal after him fucking my ass almost nightly.

I'm in my 40s now and don't really think about boarding school. I got my ass fucked, oh well. My wife has no idea what happened there so currently our two teen sons are at that school since my wife wanted them to have a good education. I've e never asked either of them if they had anal experiences yet

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Anonymous

by Anonymous on Oct 6, 2017 at 1:52 PM

holy fuck. lol #1 "surprised my asshole still functioned normal after him fucking my ass almost nightly" laughed so hard. I seen many thick nine inch cocks but I will not let them fuck me... to big. some dudes love them though.

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Anonymous

by Anonymous on Oct 7, 2017 at 9:07 AM

Fourth grade was special for me also. It was in fourth grade that a fifteen year old boy popped my cute little cherry ass. Looking back it was pretty funny, he'd wait for me after school, knock off a quickie where ever we could get a little seclusion. I was also lucky because his teenage penis was small enough not to hurt or do any damage.
By the time I entered fifth grade him and a few of his friends were entering me at any opportunity. It did change me a bit, I became sissyish and took a liking to wearing girls, mainly my sister's panties in secret.
By the end of fifth grade teenage boys would trade panties for my boy's ass, I became a real panty addict, lol. I look really good in them too!

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Anonymous

by Anonymous on Oct 7, 2017 at 9:49 AM

Yeah I post the #1 comment. And yes I was surprised that guys big dick didn't leave my asshole stretched. When he got it in my tight little asshole I though there was no way I'd be the same again! That huge uncut cock coming to me nightly for sex, my roommate saw his cock and asked how the hell do you take that! Thank god I wore white briefs, my ass would be leaking cum after sex.

I guess I'm one of those lucky straight guys that can say I took a thick nine inch one up my ass while in school! Hopefully neither of my sons get one that big is sex still happens there.

I can't tell you how many dicks I had in my ass over the years, must be around 50. The worse part was getting your cherry popped. Once that happens you kinda just got used to it, became a normal thing. I'm not and was never a fan of receiving anal but you gotta do what you gotta do.

Tonight when I talk to my sons over FaceTime I'm gonna ask them if they need to talk about anything to see

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Anonymous

by Anonymous on Oct 14, 2017 at 8:54 AM

Ya, I can't tell you how many times my tighty-whitie underpants went home full of other boys cum. Had my first mancock at twelve and was really surprised that he could get it in me. I tightened back up amazingly fast too.

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Anonymous

by Anonymous on Oct 27, 2017 at 8:41 AM

#5. Thank god for tighty whities! No wonder our moms made us wear them growing up! Caught all that cum!

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Anonymous

by Anonymous on Jul 18, 2018 at 2:39 PM

Total BS comments.

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Anonymous

by Anonymous on Dec 28, 2018 at 1:45 PM

#5 at least is BS - Mr Tighty-Whitie mancock boypussy again. He's lost his virginity about 500 different ways on here.

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