Every guy has his first time whether it is with a man or a woman. For a guy losing your anal virginity is a big deal. It's one thing when you are sucking another guy's cock, licking his ass or even fucking him. It's quite another when you submit your hole to a dick.
At a certain point a teenage boy, when he realizes that he is queer, will seek out someone to take his cherry. For me, that happened when I was 15.
As a teenager, I certainly would not be described as a young Greek god. I was pudgy, bookish and shy. At school I mostly stayed to myself. I was an only child living in the country. My choice of friends was limited. Luckily a boy about the same age lived down the street. His name was Larry and throughout our childhood and teenage years we formed on-again-off-again friendships. When I was 13, I started fantasizing about having sex with boys at school. By the time that I was 14 I wanted to try the real thing. I craved more than just sneak peaks of dicks in the locker room or watching the sweat run down the chests of the jocks as they played "shirts vs. skins" basketball.
I decided that I needed to acquire a good friend. I needed someone to seduce. Finding a boy from school was next to impossible. Gay teenagers of that era hid deep in the closet. Plus my school was strict. I remember that one boy was caught jerking off into a bathroom sink by a teacher and he was expelled. I could only imagine what would happen if the teacher would have caught me with my mouth around that boy's dick.
That left my neighborhood. Although Larry and I had gone our separate ways since we were around 12, he did live close by and was basically stuck in the same isolated situation as me. He had an older sister and two younger brothers but, like any teenager, I am sure he tired of being around his family. Larry's only drawback was that by 15 he had a lot of dark body hair. In fact, he already had started shaving. My jack-off fantasies always involved a smooth blond boy from school named Jamie Dodd. However, beggars can't be choosers. At some point, I guess I decided that Larry was to be the one.
I can remember how we rekindled our friendship. Larry liked tennis so I got a racket, took lessons and learned to play. I wasn't great but I had a decent serve and I could keep up a volley. At some point we must have been taking our rackets to school, when we started talking tennis and decided to play matches. We got closer and really started to enjoy each other's company outside of the court. We went to concerts together and rode our bikes to the store. When winter came the tennis stopped and we started playing card and board games in the basement of my parent's house.
I don't recall when we first decided to play penny poker. That became our favorite game. Each of us had a glass jar full of pennies and we'd play for hours. "I'll raise you 10 cents," meant that you had a real good hand.
Of course, like most teenagers we'd joke about sex. It's was always in a obtuse manner. I know at several points one of us brought up the subject of strip poker. My dick would always stir in my pants.
One day we were playing our usual poker game in the basement. My parents were not home so it must have been a school holiday. Exchanging pennies had grown stale and we were both restless. The strip poker reference came up again and I remember telling Larry that we should try it. He protested saying that you only play strip poker if girls are present. After some taunts of "Chicken" he relented to try it. However, he said that we just play until we get to our underwear.
I know that I didn't try very hard to win so I quickly wound up in my undershorts. I think that Larry only lost his shoes and socks. Needless to say, my underwear was tented due to my boner. Larry saw my protruding shorts but didn't say anything. I know he wanted to end the game at that point since obviously we were rapidly going way past the line of friendship. I told him that I wanted just one more hand. If I won the hand, then I won the game. If I lost, I'd strip.
Of course, I lost. I stood up and pulled down my underpants. My hard cock stood straight out. Larry made some comment that everything was getting just a little too weird. Then he asked me why I had a boner. I told him that I was really horny. I started to pull on my dick. He said that I was being gross but he kept watching me jack off. I told him I would shoot my load in front of him if he went upstairs and got me a paper cup. For some reason I thought it would be neat to let him look at my cum in the cup after I shot my load. Larry agreed. He ran upstairs to the kitchen and returned with a cup. He gave it to me making sure to stay away from my throbbing dick. He then sat down in the chair.
I started to pull on my cock. I guess Larry was a little freaked out so he asked me to turn away from him so he did not have to look at my dick. I turned around and kept jacking. Being a teenager it didn't take me very long to shoot my load. I had to wipe my cock head against the side of the cup several times to remove the cum from the tip.
After shooting my load, I felt very embarrassed. I set the cup on the table and quickly put on my clothes. Larry told me that he had to go because it was getting close to dinner time. Larry said that he would throw away the cup. He took it off the table and carried it upstairs. I heard him put on his jacket at the top of the stairs and leave.
For several days afterward we avoided each other. Somehow I got the courage to call him and we talked as if nothing had happened. I convinced him to come over again. We resumed our penny poker games. Our platonic friendship continued.
Since I had no outlet for my pent-up sexual desires I was reduced to finding a mechanical means of satisfying the need for my anus to be filled. In shop class I fashioned a 2 inch diameter dowel rod into a dildo. I rounded the ends and put several coats of varnish on it to make it smooth. After I brought the dildo home I began slathering it with Vaseline and shoving it up my ass on a regular basis. I would then frantically jack off. I learned to pull out the dildo just before I came. Otherwise it really hurt to extract the dildo from my hole.
Spring arrived and we started our tennis games again. However, on rainy days we returned to poker in the basement. Larry was now aware that I was a fag and used it to his advantage. During the poker games he would sometimes joke that I should suck his cock if I lost the hand. After several of those taunts I finally got up the nerve to call him on his bet. He acted reluctant but agreed. We both knew that I would lose but we went through the motions of dealing the cards and playing the hand.
After some nervous joking, his assurance that I could forgo paying off my debt and my insistence that I was a man of my word, Larry agreed to let me suck his cock. He stood up from the table and walked toward me. I kneeled in front of him. He unbuckled his belt, opened his jeans and pulled down his pants to his knees. He then slid his underwear down. He had a forest of black hair around his dick and balls. Although Larry's cock was soft, my dick was straining in my pants. I remember he said, "Suck it bitch". That pissed me off. I might be a cocksucker but I was not his bitch. He pushed his crotch toward my face and I felt the tip of his dick rub against my nose. I lifted my head slightly, parted my lips and put his cock into my mouth. I moved my head back and forth. His cock hardened. I was surprised that his boner could not have been more than four inches long compared with my six inch cock. The size didn't matter. I just wanted a dick. Being a teenager getting his first blow job, Larry lasted less than a couple of minutes until I felt his cum spurt into my mouth. I had licked my own cum after my jack off sessions so I was familiar with the taste.
After Larry came, he pulled back from me. He made a comment about me being gross because I drank his pud. Larry pulled up his pants, bounded up the stairs and out the door. I pulled down my pants, sat in chair and jacked off. I knew that we had gone past the line of friendship.
Larry and I avoided each other for months after I sucked his cock. I returned to my dildo and my jack off fantasies about high school jock Jamie Dodd. Near the end of the school year, Larry and I saw each other at the school tennis court. He came over and we talked briefly about tennis. During our conversation Larry started rubbing his crotch. He wasn't blatant. There were other students around us. His hand would just glide over his tennis shorts and I could tell that he had a boner. My cock got hard too. He asked me if I would like to walk home after school instead of riding the bus. I agreed and said that we should meet out front after the final school bell rang.
We met after school and began the walk home. Since we lived in a rural area, only the first portion of the walk was along a road. The rest was through grass fields and a forest. It was hot but we made good time. I remember when we reached the shady forest we sat down on a log. We talked about general crap at school.
Then I noticed that Larry was once again rubbing his crotch. Since no one was around, he started massaging his cock through his pants. I asked him if he wanted to fool around with me. He stood up, opened his pants, unzipped his fly and pulled out his dick. I am sure that he was expecting another blow job. I wanted more.
I told Larry to follow me a short distance down the trail to a clearing where sometimes the teenagers had bonfires. Of course, legendary stories were told about how so-and-so fucked some girl in this clearing. I wanted to add my story to that legend. As we walked, Larry left his hard dick hanging out of his pants, bouncing in front of him. He was too horny to put it away. I'm sure if I would have touched his prick Larry would have shot his load.
The clearing had large rocks and junked cars that blocked the view from the trail. We went behind one of the cars. Larry yanked down his pants to his knees and began jerking off. I knew that he was close. I sat on the ground and took off my shoes and my shirt. Larry looked at me strangely. I know that he wasn't interested in seeing my body. He just wanted his cock in my mouth. I stood up, opened my belt, unsnapped my pants and pulled off both my pants and underwear. I was naked except for my socks. I turned away from Larry and got down on my knees, Then I leaned forward resting on my forearms. Larry now had a clear view of my ass.
It only took a few moments before Larry realized which orifice I was offering him. He kneeled behind me and scooted between my legs. I heard him spit in his hand. I turned my head and watched him rub the spit on his cock. I then felt him rub some of the spit on my asshole. He moved forward and started probing my bottom with his dick. His cock found my back door. He pushed inside of me. I thought that the dildo would have made me ready for his cock but his spit covered prick hurt when it entered me. Larry only delayed a few seconds before he began humping me. Neither of us said anything. Larry fucked me for about five minutes before he came. After he pulled out I frantically beat off and shot my cum on the ground.
We were both dazed after our impromptu fuck session. Larry pulled up his pants. I put on my clothes. We continued our walk home in complete silence. We only exchanged parting nods when he we got to his house. He walked up to his door and went inside. I continued up the hill to my parents' house.
When I got home I went into the bathroom and shitted out his juice. Besides a few "hello's" in the halls at school we never spoke again.