Loosing it in High School

My First Time

Picture it Georgia 1991.  It was my senior year in high school.  I had known for many years now that I was attracted to boys and not girls.  Things were way different in that time frame especially in the south.  I had messed around with my neighbor many times over the years when I was younger, just fondling one another but nothing else.  I was always picked on in school for being a little husky as well as being gay.  I think the kids knew it I was called the usual names fag, cock sucker you name it.  I had begun masturbating at a very young age after as a small child my brother who was 5 years older than me masturbated in front of me in the den one day after school.  I was in awe of how large his penis was now mind you I was only probably 8 or 9 at the time so I had not gone through puberty yet.  I will never forget it he was sitting there in the black leather recliner completely naked jacking off till he shot his load all over the chair.  The first time I jacked off I had an orgasm but didn’t have sperm yet so nothing came out.  I would throughout the years jack off thinking about the times my neighbor and I had played around with each other in our younger days. So now fast forward to my senior year of High School.  I had already turned 18 the previous fall before all this happened.  Jamal was much younger then I because he was an under classmen.

Jamal started coming up to me in the Library just out of the blue during lunch time.  He would sit down at the table I was at striking up a conversation.  Eventually our talks turned to sexual stuff which I loved because I was a horny teenager.  I would have talks about sex previously with other guys I was friends with over the years but that was all that would happen was talking.  So finally one day Jamal looks at me saying that he wanted to bend me over the table and fuck my brains out.  Like I stated earlier times were different in those days I was scared to say anything other than dude you are barking up the wrong tree.  See I wasn’t sure if he was being serious or if he was trying to out me so that others would beat me up.  The more we would talk over the months the more comfortable I became with him to the point where I felt like I could trust him.  One thing that always bothered me was that up till that time the only two cocks I had seen had been my brothers and my neighbors.  When we were like 14 and 15 my neighbor had come down to my house one day and dared me to jack off in front of him.  I dared him to walk around the inside of my house without any clothes on.This afforded me the opportunity to see his cock 3 different times it was bigger than mine and pointed straight up in the air it was so beautiful.  See I always felt small compared to them and felt something was wrong because mine had a slight curve to the left. 

Well finally one day that early winter Jamal came into the library sitting down at my table and we began to talk.  Now let me step back for a minute I was raised in an area that had been transitioning for a couple of years.  I was in the minority in my school.  I was Caucasian and Jamal was African American.   So this day I had found a book there that talked about sex and it had a drawing of penis in it to explain an erection.  I showed him the book saying don’t take this the wrong way but I have always wondered what an African American’s penis looked like.  He didn’t really say anything.  A few days later again we met up in the library had a little bit of a conversation and then he said hey I need to go to the rest room do you want to go.  I was like no I am fine not even thinking that he was trying to get me there for a reason.  I thought about it for a moment and decided that I would go.  I went into the first restroom he wasn’t there so I ran back around to the other restroom as there were multiple ones in the school.  I walked in and he was standing at the urinal.  What should I do I panicked not knowing what would happen if I went to the urinal next to him which had no dividers around them.  I chickened out and ended up going into one of the stalls to urinate.  When I came back out much to my surprise he was taking his time washing his hands.  Then all of a sudden he said hey I want to ask you something.  He peered around the corner looking to see if anyone was coming.  Jamal turned around walked up to me and reached down between my legs and grabbed my cock and started feeling me up.  He proceeded to ask me what you would do if a guy came up to you and started doing this.  I was in shock I didn’t know what to say.  I couldn’t get words to come out of my mouth it felt so wonderful to have another person touch my cock through my pants.  Finally the bell rang and all I could say was stop it.  He then said okay you would say stop it.  I tried to reach at that point to touch his dick but couldn’t feel anything.  Come to find out later he had on his boxers, gym shorts, and dress pants so I couldn’t grasp him the way he did me.  I then said when do you go to lunch.  After he told me I said I have class that time frame I go before but look I am going to get out of class and I will meet you in the library. Now this was when the fun started.

So I had access to a locked storage room in the back of the library.  I went into the office retrieved the keys unlocked the door then left it cracked.  As soon as he got there I explained to him that I was going to go into the back room then he could wait a few moments making sure no one saw him and follow me in there.  Then I waited the door cracked open and Jamal stepped in closing the door behind him.  I said now what is it you were asking me.  He said touching me again I just wanted to know what you would do if a guy started doing this.  I let him touch me for a while then again to no avail I tried to do the same for him.  We stopped then started just pacing around the room asking each other various questions.  What would you do if guys said suck my dick? What would you do if this or that?  I finally picked up the nerve and asked Jamal what would you do if a guy walked up to you in the restroom saying he let me see your dick? His answer was well it would depend on who it was.  I said well what if it was me.  He said you oh of course you could see it.  I immediately without blinking an eye said okay let me see it.  Jamal stood a little ways away from me started to unbutton his dress pants then unzip them.  He reached inside his gym shorts and boxers pulling them slightly down to reveal to me one of the largest cock’s I had ever laid my eyes on.  I was in awe with not only how big but also how beautiful the mushroom head was he was semi hard and it was all of 9 inches and thick as all get out.  He shook it a couple of times and then put it away.  Next he grabbed me unbuttoning my pants to release my cock so he could see it.  Jamal reached down grasping it with his hands slowly masturbating me and I won’t lie it felt so well. I got everything put back together and we continued to ask each other questions about first one thing and another.  I then asked him could I see his cock again.  He proceeded to pull it out letting it dangle right in front of me.  I then asked may I touch it.  He said yes you can touch it I reached down so enamored with this huge dark penis I wanted to put my lips around it even though I had never done it before and had no idea what to do.  I was sitting down in a chair while he was standing in front of me.  I looked up into his beautiful face straight into his eyes asking can I put it in my mouth.  He explained yes go ahead.  I started slowly pushing my lips across this huge cock taking it slowly into my mouth.  I went up and down on it a time or two it felt so good to have a cock in mouth.   This was something I had dreamed of doing for years.  I stopped sucking sat back and Jamal put his cock away.  It was nearing the end of lunch so we concluded for that day. I went home and so overly excited about what happened. That was the day I jacked off about 7 or 8 times thinking about me actually getting to suck a cock that day.  The last time very little to no cum shot out and my cock was getting raw so I quit.

It was a few days letter that Jamal came into the Library early one morning before school started.  He looked at me saying meet me in the restroom on hall so and so.  I walked in the restroom not seeing him at first then he stepped out of the last stall.  The thing about our school back then was there were tile walls separating the toilets but now doors for privacy.  I went in he pulled out that beautiful cock and I began to suck it.  He stopped me so that I could stand up and then he turned me around.  He began to pull my pants and underwear down around my ankles.  Jamal then stated get up against the wall I want to stick my cock as he called it by your butt hole.  I had never been fucked before so there was no way he was going to be able to enter me.  He would basically hump me till he climaxed shooting his load on the floor.  We did this multiple times usually in the morning; however one afternoon we went into the bathroom locking the door behind us he was almost about to push deep inside me when there came a knock on the door.  It was the custodian she was there to clean.  She was mad why you got this door locked.  I explained to her that I had been jumped before in the bathroom so I would lock myself in so no one could cum in there while I was using the restroom.  I left Jamal in there and he waited a few moments to come out.  It had become to risqué to do this anymore so I explained that I had my house to myself in the afternoons he could cum over there.

I finally got the chance for Jamal to come over to my house.  I watched as he crossed the main street that I lived on then jumped up to open the door before he reached it.  We made small talk and I led him into my bedroom. He disrobed all but his shirt which he wouldn’t take off, later he said that was in case he had to make a quick getaway.  I laid on my back in my bed while Jamal climbed up pushing my legs in the air to reach my anus.  He put the head of his cock at my sphincter and started to push inside.  It was met with some resistance however he finally pushed in as pain went through my body.  He continued till all 9 inches was up inside of me.  I was in pure ecstasy.  He began to pull out and push in as the pain started to subside.  He continued pumping in and out of my anus until he said I am about to cum he pulled out removed the condom shooting his hot load of creamy juice all over my stomach.  We would meet up many times over 2 or 3 years him always fucking me sometimes with a condom sometimes not but he would always pull out to shoot his load on me. 

Jamal came over early one morning and we got in the shower together it was so magical to be able to soap up his body.  I explained to him that I would love to lick his ass which he permitted me to do.  I was always fucked by him he never allowed me to fuck him as he was a total top.  He then proceeded to tell me stories of all the guys at the school he had sex with or had let suck his dick.  I was shocked to find out how many of the kids in my school were actually fooling around with each other but none ever included me.  The more we connected the more I fell in love with Jamal however the feelings were not mutual.  To him I was just a side piece.

Then at the end of that 3 year period the next to last time I saw Jamal he had moved into his own apartment.  He called me that day asking could we meet up I said sure he explained I want you to cum to my place.  I got ready headed down the road arrived at the apartment complex got out and knocked on the door.  Jamal opened the door to my surprise he was wearing a bath towel.  He explained I am taking a bath come on in.  As soon as I closed the door he removed the towel exposing his beautiful young tight body.  I followed him to a back bedroom that had a bath attached to it.  There were 2 red velvet couches and a bed in the corner.  I sat down on the couch while he proceeded to go back get into the tub of water to continue bathing himself.  He got out drying off and wrapped himself in a towel.  He entered into the room sitting on the opposite couch with the towel just slightly opened so that I could see his beautiful cock.  I went over to him removed the towel taking his large cock in my hand then proceeded to go down on him.  He stopped me for a moment laid me on my back pushing my legs up into the air.  He then grabbed a jar of Vaseline putting a few fingers in to get some lubing up his large 9 inch penis.  He then slid his fingers into my sweet little honey hole opening it up a bit.  Jamal grabbed his penis opening up my ass crack to push inside me he continued to do so until he was deep inside.  It always felt so wonderful to be fucked by this handsome and sexy man.  Jamal started to moaning then pulled out of me jacking his cock until he shot load after load onto my stomach.

A few years went by we lost touch with one another then he appeared at the store I was working at one day.  I was like hey how are you, we talked for a moment I gave him my phone number as at that time we had moved.  The next morning to my surprise he called me wanting to cum over to see me.    That day is etched into my memory for ever as I was still in love with him.  My heart raced as I waited for him to drive up.  I went to the door allowing him to enter in.  We talked for a few minutes he was wearing some short tight running shorts and a matching tank top that was emerald green with white trim.  After chatting for a moment he asked are you wearing underwear to which I replied yes.  I asked him the same and he said no he wasn’t.  I reached up the leg of his shorts and felt what was actually a lining like a swimsuit was.  I exclaimed yes you are I feel them.  That was when he said no I’m not so I pulled back the waist band exposing his beautiful cock being held by the lining of his shorts.   He said know you have done it you made me hard.  I said well we can take care of that.  I reached down grabbing his cock and led him back to my bedroom.  We got completely undressed.  I sat down on the bed taking his big cock in my hand leaning in to lick it then put my lips around it and suck on it for a moment.  Jamal laid me back grabbed some lotion then proceeded to put his cock at the crack of my ass.  He started to push inside of me bareback without anything but the lube.  As soon as he had me opened up he continued to pound my ass moaning and enjoying every minute of it.  He pulled out his cock grabbing it as he shot streams of sweet baby juice all over my stomach.  That was the last time I saw Jamal.  I would give anything to run into him again as he is the only man I have truly been in love with even though the feeling wasn’t mutual.