Warning! This story is sexually explicit, so, if you are not of legal age or are offended by this type of writing do not read any further. This story contains almost 3k words. To contact the author click on the blue link to E-mail: firstname.lastname@example.org Subject line: The First Time.
The First Time I Was Finger Fucked
I was a freshman in high school the first time I was finger fucked in the ass by another guy. I had been curious for a couple of years before that time as to whether I would enjoy having my asshole diddled by a skillful digit. I had played with my asshole a few times when I was younger. I would wet my middle finger with saliva or baby oil and play around rubbing the entrance to my pucker of a night while I lay in bed jacking off. Also, when I took a bath or shower I would soap up my ass and play with my asshole. A few times I actually inserted my finger in my rectal cavity, but when I withdrew it there was fecal matter attached and there was nasty stink of shit to my finger. So, by the time I was a freshman in high school I knew my asshole was super sensitive to touch.
I had heard that some guys found anything penetrating their assholes to be repulsive; however, others found anal sex play to be very sensual. I would cry out in ecstasy when getting fingered fucked or corn holed. I was one of those who found finger fucking and cornholing to be very sensuous; furthermore, for me to be finger fucked while receiving a blowjob was pure bliss. At recess in Junior High School I'd heard stories from the older boys about them finger fucking their girl friends. Of course, they always wanted to pass the digit under our noses for everyone to smell the scent of the freshly fingered friend. I also heard stories about guy's cornholing each other.
I, in fact, had been cornholed by my best friend the summer between fifth and sixth grades. So I knew a little something about anal sex, but not much about the sensual pleasure of it. I remember the night I was cornholed vividly. Dad had set up a tent in our backyard for my friend and me to spend the night together. The tent was square a four man tent made of dark green canvas and had that canvas musty odor to it. The tent was one used by Dad and his friends for fishing and hunting. My friend and me had previously shown each other and compared our pathetic little peckers in that tent on an earlier campout; however, that night we would get serious about sex, and go all the way.
We had planned on sucking each other off. Bobby had also told me that he wanted to experiment cornholing that night, something we had been planning for weeks prior. I had heard stories, but wasn't experienced in anal sex so I was a little anxious. Hell, I had just learned about mutual masturbation and oral sex with Bobby. We waited until all the lights were out in the house and we were sure the parents were asleep before attempting anything. Once we felt it was safe we took off our underwear and begin playing with each other's stiff little dicks. Back then when we were hard we weren't much bigger than a hot dog. Bobby was about a half inch longer, and both of us were circumcised. Neither one of us could cum yet, but playing with our penises felt good at that age.
As we lay there in the moonlit tent I asked Bobby where he learned about cornholing. He told me that his uncle who would be in the eight grade in the fall taught him. He said that he had learned everything about sex form his uncle, and he and his uncle had been playing around sexually for a few months. Bobby told me that his uncle's dick was bigger than ours, he had hair around his dick, and white stuff came out of its head. Bobby said that when they sucked each other off the hair around his uncle's dick tickled his nose. He told me that his uncle had shot the white stuff in his mouth and up his ass on a few occasions, and on other occasions he would pull it out before squirting, jacking off till the white stuff came out. So, Bobby knew more than I did about cornholing, but he never told me it would hurt.
After we discussed what we were going to do Bobby told me that we would have to position ourselves so one was lying on his back while the other was up on all fours on top facing the opposite direction. So, Bobby assumed the down position and I straddled him so my dick was over his face and I was facing his dick. We began sucking each other's dicks until we felt that funny feeling we would experience after a few minutes of sucking. After that feeling we could no longer keep sucking each other because we were too sensitive and our peckers would go limp. We lay back on our sleeping bags talking about what was next so our dicks could get rested and hard again. Bobby told me that cornholing was like when two dogs humped each other. So, one of us would get down on all fours and the other would mount the down dog. He also told me that he had brought along some baby oil to help.
Bobby told me that he and his uncle had discovered that baby oil was the best lube to use; otherwise, penetration really hurt. He told me if it hurt when he pushed his pecker inside me to just tell him to stop and he'd wait a few seconds till I got used to it. He told me that when he and his uncle cornholed the first time they used Crisco to lube up Bobby's asshole. Bobby said that for a week after his uncle packed his ass with Crisco and cornholed him he shit biscuits and gravy for a week, and then he laughed. I thought at the time how gross, Crisco. Bobby told me to get on all fours and get ready.
I did as instructed and Bobby put some of the baby oil on my ass; it felt so good as he rubbed it in, and then he put some on his dick. He told me to get ready because he was going to mount me. He pushed his pecker into my ass kind of fast and it hurt like hell. I found myself with tears in my eyes from the burning I felt in my asshole and was whimpering with pain. Bobby asked if I was okay and I told him it hurt a little when in actuality it hurt a lot, but I didn't want to disappoint my best friend. He told me that it would only hurt for a few seconds. Again, I knew nothing about butt fucking back then, so when he was all the way in I folded forward as he lay on top of me with his dick in my ass.
After a few minutes the burning subsided and it began to feel kind of pleasurable. We lay there for a few more minutes and then he began moving back and forth and I could feel his dick sliding in and out of my asshole. Finally, he collapsed on top of me breathing hard. He was exhausted and his withering dick came out of my ass. He continued to lie on top of me for a few minutes and then rolled off onto his back. After a few minutes he asked me if I was ready to do it to him. We changed positions and repeated the process. Of course, Bobby had done it before so it wasn't that bad for him. He didn't fold forward and lay down; instead, he pushed his butt back against me and told me to push my dick in and out of his ass slowly. The first few times I completely withdrew my dick from his asshole. He scolded me telling me to keep it inside him, and to just slide it back and forth. Before long I was sliding back and forth in his ass like a rabbit mating sweating like a hog. Finally, I had to withdraw, and then the smell of shit filled my nostrils.
I pulled out that last time and it smelled terrible, and then I discovered that there were a couple of big particles of brown shit on the head of my dick and behind the coronal ridge. I wanted to wash it off as quickly as possible, so I got out to the tent picking up the garden hose I began washing my dick off. I wanted to get all that shit and oil off my dick and out of my ass. Bobby joined me and washed himself. When we were back in the tent we were quiet for a while, and then Bobby wanted to know if I wanted to suck him off again. I wasn't to keen on sucking a dick again that night that had been in my ass, even though he had washed it off. That was the first and last time we had a chance to do anything sexual together. The following week my dad announced that we were moving as he had accepted a job in another state. We moved and I missed Bobby and our sports activities as we called them.
I missed sports activities with Bobby when we moved to the new state where I began the sixth grade. I tried to find another sexual partner to engage in sexual activities, but no luck. However, when I got to high school I found someone with whom to engage in sports activities again. Jack who was a neighbor and a year ahead of me in high school was having trouble with algebra; in fact, he had flunked algebra his freshman year, therefore he was in my class to take the course over again. I was a whiz at math so I volunteered to tutor Jack three days a week after school.
Jack desperately needed tutoring to stay eligible to play basketball on the Junior Varsity high school team. Jack and I were the last two on the bus at the last bus stop on the way home from school. The first few times tutoring Jack nothing happened except algebra, and then when finished tutoring I'd walk the half mile on little two lane road home horny as Hell. Within a few short weeks Jack was caught up with the class and doing okay in algebra, so there was no real need to tutor him any longer. However, I continued to go to his house after school. I had fast become enamored with Jack and had already been fantasizing of a night while I jerked off about sexual possibilities between us.
After a few more weeks hanging out together Jack and I had become close friends; then one day as we got off the bus and were walking to his house he invited me to stay overnight. I had no problem getting an okay from my parents to stay with my new best friend. As we lay in his bed that Saturday about he asked if I was awake. I responded in the affirmative; we both remained silent for a while longer, and then without warning Jack reached over touching my dick. A dick that was already hard with anticipation. He then rolled over close to me whispering in my ear asking me if I wanted to jack off together.
I immediately agreed, but then he whispered that it would have to be a secret, no one could ever find out about what we were about to do. We swore a secret oath, and then began stroking each others hard cocks. I had never seen Jack's cock fully erect before, but I could tell by the feel of it that it was a whopper. I figured it to be two fistfuls, whereas mine was a single fistful at that age. We continued stroking each other and before we knew it we both blew our loads all over each other. That was the beginning of a great friendship that lasted throughout our high school years, and in the weeks ahead we would become what is now referred to as fuck buddies.
Back in the day a fuck buddy was a girl friend or boy friend with whom you could engage in sexual relations, but there was no romantic bond. Just a partner to have sex with occasionally; a relationship completely devoid of all the bullshit such as dating, dinners, and other romantic dating rituals, someone you didn't have to spend all your money on, and then after spending a fortune may or may not get some sex. Most of the time the person was another trusted boyfriend who would not fink you out and you had many sessions of sex with throughout those teenage years.
I was in dire need of a buddy like Jack because I hadn't had any human sexual contact since we moved and I was split up from Bobby. I was a horny teenager and so was Jack, we both needed each other. After a few sessions of mutual masturbation we moved on to oral sex play. Of course, the sixty-nine position was the favored position for young school boys because neither could back out after blowing the other. After a few sixty-nine sessions Jack asked me if we could try something new. He explained how the sixty-nine plus one worked and told me he would do it first to give me an idea of how and what to do. He told me if it hurt or I didn't want to proceed any further to slap him on the buttock and he would stop. I was eager to try something new, so we got into position facing opposite each other on the bed. Jack coated his fingers with a goodly amount of Vaseline, and then we assumed the sixty-nine position where we began to fellate each other.
After a few seconds Jack pushed my legs apart and ever so gently began rubbing the Vaseline into my rectal area. His middle finger was pressing firmly against my awaiting asshole but ever so delicately. He began to push past the point of pain penetrating my sphincter fully. Once he had cleared the threshold of pain and was deep inside my rectal cavity with his long middle finger he found the magical button and began massaging it. Oh God, I wanted to cum, scream, and shit all at the same time; it felt so fucking good as he rubbed my prostate. When I blew my load I almost suffocated Jack with the powerful amount of spooge I blew down his throat. He started gagging and had pull of me to spit some of it out before returning to me. From that time on we refined the sixty-nine plus one finger fucking and cock sucking exercise where it became a permanent part of our sexual repertoire.
Jack and I were sexual partners until he graduated from high school and then went into the military. When he came home on leave from basic we spent as much time as possible together pleasuring each other. Jack never took me anally, but enjoyed me cornholing him. I think Jack figured because of his size he might hurt me. He was a big boy. We measured it one time and the damn thing measured out at almost nine inches long and six inches of girth. His dick never stood straight out when it was hard; it kind of hung down towards the ground when it was erect, whereas mine always stood up at a forty-five degree angle and was hard as steel. I saw him in the shower and he must of have hung at least six inches long flaccid. We used to joke that he needed a holster for his weapon.
I was away on Christmas break my senior year of high school
when Jack came home for those two weeks of leave before he went to