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NineTails
04-03-2014, 05:59 PM
Please let me know if this is in the wrong section..



It was 1982 the summer of my freshman year in high school and I was still trying to figure out all the things I could about girls, I was lucky enough to have lost my virginity to a girl behind a local convenient store last year on a dare but other than that I was still a drooling unexperienced boy. I was not a big kid, maybe 5’7 and skin and bone, athletic but not muscular.

I can still remember the first time we met it was at a local county fair and I was sitting there alone watching the tracker pulls and loving the loud engines and the cheering going on, off to my right a saw an older man and a group of boys my age and they were having fun and laughing loud. After a little while a couple of them started talking to me and we ended up having a time but as the event ended my mother showed up and I knew it was time to go.

The next day when I got to the fair I happened to run into that same man and one of the boys from the night before and we started talking and hanging out again but this time the older guy joined into the conversations and he turned out to be a very nice man that just enjoyed hanging out with younger kids and he seemed innocent enough plus he kept buying us food and ride tickets so I ended up spending most of the day with them. We ran into my mother as the evening came around and the older guy spent some time talking to her while we continued to ride more ride and I thought it was cool that maybe mom might be getting hit on and maybe she would get to go on a date or something, but as we got off the ride it turned out she knew him through her work and said it was ok if I wanted to stay longer and he would drop me home after the fair closed which I was very happy about.

The rest of the evening and night we just hung out and had fun talking about all the cute girls that were around he even ended up buying us some beer and we all just chilled watching all the events and laughing because we were getting drunk for the first time, but like promised he dropped me at the house as soon as the fair closed and since that was the last night of the fair I figured that it was the last time I would see them and just want on enjoying the summer.

It wasn’t until two weeks later that my mom came home from work and told me that he had asked about me and wanted to know if I was interested in going to the lake with him and some friends that weekend and she told me that he is a very well-known person in the city with a high title and she thought it would be good for me to have a male influence in my life so I agreed to go, secretly hoping that he would buy more beer and I would be able to get drunk again.

He picked me up early Saturday morning and with one other boy we headed out with his boat in tow and to my great surprise as soon as we turned the corner from my house the other boy handed me a beer and the fun began, he pulled us around on and inner tube and we even tried to ski for a while but as the day went on our buzzes were too much for the skiing and we ended up just relaxing and watching the girls in bikinis for most of the day, when it was time to go home he asked me if I wanted to just crash at his house for the night and then we could come back to the lake in the morning, I quickly agreed and we pulled over to a payphone and call my mom for approval before heading to him house.

Needless to say I was trashed by the time we were ready for bed and the other boy headed home since he only lived a couple houses away leaving the two of us alone and as he helped me up the stairs into his bedroom he told me we could just crash here together which at the time didn’t seem odd to me for some reason considering when I stayed at other friends house we always crashed in the same bed.

I don’t remember falling asleep but when I did start to wake up I was surprised feel a hand sliding under me softly stroking my morning wood and as I realized it was him touching me a began to panic and rolled over onto my stomach acting like I was still asleep, but that didn’t stop him as soon as I relaxed the hand slide under me trying to reach my cock again, but this time I freaked and just sat up turning toward the other side of the bed and stood up real quick pulling my pants up and as I walked around the bed I heard him as me if everything was alright for which I nodded yes and just told him I was hungry and headed downstairs.

I sat in the kitchen trying to figure out if maybe he was asleep and not realizing what he was doing or if he was really trying to grab my dick, and as he entered the kitchen dressed fresh out of the shower I passed it off as he was asleep and didn’t mention anything.

We had another good day at the lake and as he dropped me off at home we made plans with my mom for him to pick me back up in a couple days and I was going to help him up at his farm outside of town and he would pay me for my time and I would be back on Sunday night again.

The thought of making money sounded good and I was sure the touching was just a mistake so I was excited as he picked me up and we headed out of town, his farm was really nice and I helped him get things cleaned up for a couple hours before we headed inside due to darkness and proceeded to get a nice buzz on with the help of some beer and this time we also smoked a couple joints to add to the fun But when it was time to go to sleep I opted to stay on the couch for the night not wanting to have another accident. He brought me a pillow and blanket and I crashed.

I woke up in the morning laying on my stomach like normal but once again felt that hand under me trying to reach my morning wood and started to get nervous again because there was no way he was sleep walking all the way downstairs, I didn’t really know what to do because I didn’t want to make him mad and cause a scene and this guy had some serious cash which living like we did scraping by we really could use the extra money helping him around here, so I just laid still and let him get his feel hoping that was all he wanted.

I am not sure how long I laid there but my dick was getting uncomfortable smashed against the cushions like I was laying so I acted like I was still asleep and stretched and kind of rolled onto my side away from him, but sure enough his hand snaked under the blanket again and across my body this time though he slipped it into my underwear and took a full grip on my extremely hard cock and began to stroke it.

I was lost as what I should do because yes my dick was hard as hell and it kind of felt good to hand someone stroking it but I was in no way gay and never even thought about another guy before, girls were way to cute and sexy for me to be thinking about guys but as I felt his other hand grab my shoulder and roll me onto my back I just allowed it to happen but I kept my face turned towards the back of the couch not wanting to see him. He continued to stroke for a little bit and it did feel good but also weird and as he started to slip my tighty whities down my heart really started beating fast but the real shocker was when I felt him lean over my body and then as my dick slid into his mouth and he started moving up and down my shaft the feeling was incredible, here I was getting my first ever blowjob and it was from a 45 year old man.
My mind was having such a hard time with the fact that a man was sucking my dick that it was hard for me to enjoy or get off but as he continued to suck up and down his other hand reached down and started massaging my balls while his tongue ran the length of my shaft. When I did finally start to feel my cum rising I began to panic again not wanting to say anything or even look at his I just tensed up and exploded into his mouth and the feeling of him continuing to suck on me while I was Cumming was intense.

Once I started to go soft in his mouth he pulled away and I felt him pat me on the chest and as he got up and just walked away, It was kind of weird at first but we just didn’t talk about it and as the day went on things got back to normal, a couple of other guys my age came over and we partied for the rest of the night until we all passed out around the house. It was a perfect setting for a group of boys my age, no parents and as much weed and beer as we wanted.

I woke up the next morning with the same feeling on my hard-on only this time I was already laying on my back on the couch, “shhh or they might hear us” is all he said as I once again turned my head to the side not wanting to look at him as he slid my underwear down again and took me into his mouth. I was scared to death that one of the other boys would wake up and see him doing this but as he continued to slide up and down my shaft flicking his tongue across the underside I felt the Cum rising and when he shocked me by sliding his finger into my ass I exploded deep into his mouth, only to have him once again pat my chest as he walked away.

That day after everybody had gotten up and headed home leaving us alone in the house he walked passed me and dropped a $100 bill down on the table in front of me and as I looked up at him he just smiled and told me it was for all the work I had already done and that there was more of that to come.

I was shocked considering I was only expecting to make $100 for the whole time I was going to be here helping and could not believe that I actually might be able to make more so I quickly jumped up and headed out to start cleaning up more around the farm not even thinking that it might be payment for the “other” thing he had done twice now with me.

That night a couple of older guys stopped by and I found out one of them was the local sheriff and that kind of freaked me out since we were all sitting around smoke weed with him but he seemed just like us smoking away and after a little while I calmed down and even went with him to get more beer which was cool riding in his undercover car with the radio and hidden lights.

They all left about 1am and in the morning as I woke up his hand was already stroking me and this time I just rolled over having started getting used to getting a blowjob each morning but instead of leaving me laying down he scooted me around so that I was sitting up and he was on his knees between my legs.

To keep my not looking at him going I just raised my head and stared at the ceiling imaging it was the cute girl from school sucking my dick and not this old man, he really took his time this morning though making sure to slid his tongue from base to tip over and over and he even took my balls into his mouth which was a new experience for me and soon his finger found my ass again and as he slid it in I grunted in pain because I had never had anything in there before but he just started gently pumping it in and out as he throated my cock and it did not take long before I was filling his mouth once again with cum and as I was coming down off my little high his patted me again before walking out of the room.

Now some might wonder why I kept letting him do this but in the mind of a boy my age at the time I figured it wasn’t hurting anything because hell I was getting blowjobs and it wasn’t like I was going anything other than just sitting there so all was good in my mind.

The days at the farm went by fast that week with all the partying and on Saturday I was already bitching about not wanting to go back home the next day and he just smiled and picked up the phone and called my mom explaining that I was being such a good helper around there and he was still on vacation and asked if I could stay the rest of the summer down there which to my surprise she agreed right away not thinking anything was wrong because he was such a bug guy in the city who would ever question him.

When he hung up the phone he just smiled and we smoked another joint sitting there on the couch watching TV and as we finished the joint he switched the channel to one of those pay-site channels which I had never in my life seen and as the porno started playing I was mesmerized watching the girls getting fucked and before I knew it he had his hand in my lap stroking me through my jeans.

I was kind of embarrassed even though he had sucked my dick so many time this was different we were both already awake and sitting up unlike before were I would always play asleep and look away, but as he undid my jeans and began pushing them down I did not stop him, instead I ignored what he was doing and just stared at the screen losing myself in the action there and as he knelt between my legs again it felt good watching a porno while getting my dick sucked by what my imagination told me was the girl on the screen and not this old man. I let him move my legs around while he seemed to be getting comfortable and even let him take my pants all the way off while he sucked my dick, it felt weird went he spread my legs out wide but as I felt his tongue on my balls I figured he just wanted easier access to me ball and just relaxed and went with it even letting him pull my shirt off leaving me naked in front of this grown man as he sucked my dick in and out of his mouth making sure to stop at just the right times so that I did not cum to quickly and in a way driving me crazy,

I felt him fumbling around for something and did not give it any though because I did not want to look down at him but as he slipped his finger into my ass I figured out he has put some Vaseline on his finger this time and he started fucking me with his finger deeper and deeper while sucking me with the same speed and timing with felt weird but stated to feel good also, he readjusted himself again this time scooting closer and resting my legs up on his shoulder while pumping his finger in and out of my ass and I felt uncomfortable beginning spread open like this but exploded into his mouth and he moved away again with my little pat before I could say anything.
That night we went out to a local diner to get some dinner and while we were eating he handed me another $40 dollars and thanked me for earlier which I thought was weird because even if it was for the blowjob he had given me I didn’t understand why he was paying me since he was the one doing all the work because I had no intention of doing anything like that on him but I just smiled and eat my dinner happy to have more cash in my pocket.

On the way back to the farm after dinner he asked if I liked making that much money and I quickly said “hell yes it is easy money” and we both laughed and then he asked me if I wanted to keep making that kind of money which I just shook my head yes as I puffed on my cigarette thinking this is going to be a great summer full of cash in my pocket and free blowjobs. “Good, then when we get back home we can do some more before we go to bed tonight.” I just smiled.

Once again he had me naked on the couch with my legs on his shoulders sucking my dick with his finger in my ass and I was enjoying the porno playing on the TV, “I love the taste of your cum” he said for which I just smiled and never looked away from the TV screen, “I think we will have a lot of fun together with you making some nice extra money, don’t you think” again I just smiled wanting him to just be quiet and suck so that I could watch the TV but as I felt him shift again this time raising up higher between my legs I had to move my head sideways to be able to see around him but as his finger began to press into my ass it felt a whole lot bigger and I grunted in pain and brought my hands to his chest to push him away and it was then that I actually realized how much bigger he was than my little body and he didn’t even budge and as his finger started to go deeper I turned my head towards him and started to tell him it hurt but found his face right next to mine and knew right then that it was not his finger in my ass but instead it was his cock and as he shoved forward I yelled out. “Fuck, no…no… dude I don’t want to do this… Please…” but it was useless because he was so much bigger than me and with my legs on his shoulders there was no way I could get enough leverage to push him off and he started pounding into my ass.

Each thrust brought more tears to my eyes as I continued to push against him as the pain in my ass was only surpassed by the cramping in my gut as it felt like he was stabbing me and punching me all at the same time, within a few strokes he was fully into me and slamming his cock hard inside of me and I could feel his balls slap against me with each stroke and after a little while all I could do was lay there with my head turned staring off across the room while this old man fucked my virgin ass like it was a well-worn pussy or something. I felt him reach between us and start stroking by dick as he fucked my ass causing me to grunt in pain with each stroke and was surprised when I exploded all over my stomach right before he filled my ass with his cum. He laid there on top of me for a few minutes afterwards while I felt him getting soft inside of me and as he pulled out my ass seemed to keep spamming and the pain did not want to go away and as he leaned down and licked my cum off my stomach all I could do was keep staring away not wanting him to see me crying like I was but soon I felt the familiar pat on my chest and he was gone leaving me to stager to the bathroom and sit there crying while his cum leaked out of my ass.

I am here all summer? Is all I thought as I fell asleep trying to ignore that pain my ass was feeling and really wanting to go home….


Comment would be very welcome either about the story or writing style, Would also like to know if you would like me to continue the story.

Thanks