If a sexual scene involving male-to-male relationships offends you, then you should not read this story. Additionally, if you are under 18 years of age, in most state and countries, you are not allowed to read this story, by law. Check with your local laws regarding such.
Chapter 1
My Best Friend Brian
This story takes place over 10 years ago when I was first around 18 years old. My name is Brian and ironically my best friend's name is Brian as well. My friend Brian was around 14 years old at the time. We first met when I was around 14 years old so that made him around 10 or so. We are still very good friends to this day, I'm always dreaming about our sexual relationship we shared together for so long. This story is true and I will try my best to recollect the events.
It was a hot summer weekend in Kentucky and we were driving down to Louisville to see a mustang car show and drag strip show. Wait first let me back up to this weekend and tell you how we started our sexual relationship.
Our first sexual encounter when I was around 16 years old and he was around 12 or so. Now before this weekend we have had a number of sexual encounters, it all first started when I used to cut his hair. When I was cutting his hair for some reason it always made me hard as a rock, I would rub my hands through his hair and get so turned on. He was about 5 foot 6 and skinny as a toothpick, he wasn't too far into puberty yet so he had a small cock then. He had the most perfect brown straight short hair; he would always let me cut it because the barber would always fuck it up. So I remember one night he was sleeping over at my parent's house and I just finished cutting his hair really short. I would love running the clippers up the back and sides of his head, god that turned me on! I would dream about him sucking my cock while he was sitting in the chair with the barber cape on, but unfortunately I would find him sucking my cock that way would never happen. It was a late night so we decided to turn in, I had a queen size bed so he always slept with me in my bed when he stayed the night. As we were laying in bed, we started talking about some girls that we both thought were very hot at the time. He asked me "Have you ever had sex?" I actually have before at the time so I said yes. He then wanted to know what it was like, so I continued to tell him it felt like the best thing in the world.
For some reason I started to feel him up in my bed, I don't know what brought it on but I just did. I started to rub on his then small cock and gently rubbed on his balls, he would start to moan like crazy, I could tell that he was really enjoying me jacking him off. I then reached around and started to caress his nice ass, wow did he have a great ass. I started to get naked myself and took his hand to my 6 inch cock and let him jack me off for a couple minutes. While he was jacking me off I started to insert a finger in his tight ass, he was taken aback by that but he let me continue. After a few more minutes I had two fingers in his hot tight ass and I was then cumming in his hand and all over my bed. I asked him if he wanted to know what it's like getting fucked, he of course said yes.
I removed my two fingers from his hot ass and told him to get on the bed on all fours, so I now have his hot tight ass looking straight at me. I pointed my now hard cock to his waiting cherry and started to penetrate his hot asshole, god it felt great. Once I was able to get my entire cock into his ass I started to move in and out, he was moaning like crazy "Oh fucccckkkk god that hurts, but feels so good." After going slow for a while, I picked up the pace and I started to drive my cock deep into his ass...damn it felt so good. All he kept doing was oooooooooooooohhhhhhhhhhhhh, fuck me harder! His wish was my command I pounded on his ass like a jack hammer, and felt like I was going 50 mph in his ass. All you could hear was me slapping against his ass with my cock and him moaning like crazy, after about 10 minutes of fucking him hard I pulled my cock out and cummed all over his butt and back.
That was the first time that I have ever had sex with another guy and the first time my friend Brian was fucked by another man. We then collapsed on top of each other and he told me "that was the best thing I have ever felt, is that what it feels like when a girl gets fucked?" I said "pretty much, some day I will let you fuck me just like how I rammed your ass."
Now from that one weekend a few months have gone by and we really never had another sexual relationship again. Every time he would stay the night I would try to fool around with him, but he would never have part of it. I started to wonder if he didn't like what we did a few months ago that one special night. After a while I would get more and hornier and every time I would hang around Brian I always wanted to strap him to my bed and just fuck the day lights out of him. I finally asked him one night while staying at my place if we could continue doing what we did a few months ago, to my surprise he said no. I don't know what happened, it was like I just heard my heart fall to the ground...I was so confused.
Now since I was a lot older than him I was able to have a job, even though I only made minimum wage I still had a good amount of money. So I did what I thought I would never do, and that is pay for sex. So I told Brian that I would pay him for sex, I knew he didn't have any money and I knew he was too young to get a job. He asked me how much I would pay him and I said $100, he said "forget it no way". So then I told him I would pay him $200, I seemed to have his attention. He asked me "how long are you going to fuck me?" I said "as long as it takes for me to cum", he said "ok fine but I want the money first." So I paid him the $200 I promised him and told him to take all of his clothes off. I watched as he stripped his clothes off except for his shirt, for some reason he would never take off his shirt I never understood why. I always told him to take his shirt off but he said no I could get to him with it on; well I wasn't going to argue. At the time we were in my room and my parents were gone for the day, so I knew we could be as loud as we wanted. I told him to grab the desk with his hands and bend over; I caressed his nice soft ass and put a condom on my cock. I asked him if he was ready and he said go. I then entered his ass once again for a second time now; I put my hands on his hips for leverage and gave him a great pounding in his asshole. He started to moan really loud, I told him to be quiet just in case someone came home, but he kept moaning really loud. I knew he liked to be fucked, I just don't think he would ever admit it and since he wouldn't admit being gay.
So this kind of payment for sex went on for about 2 years, sometimes it was more than $200 it just all depended on how bad I wanted it and how much money he needed. We would have sex just about everywhere; I lost count on how many times we had sex in my room at my parent's house. We also had sex a lot at his house as well; we even had to pay for hotel rooms a couple times. I think if I ever kept track of how much money I paid him for sex it would probably total over $3000 over a 2 year period, yes that is how horny I was. Every time we would have sex, it was always the best time of my life. I just wish he would admit he was gay and we could still have sex today, but you will find out later in the story that just wouldn't happen. The extent of our sexual relationship had always been me fucking him, we never kissed or anything. I jacked him off once the very first night we made love, but that was it until the best weekend we had in Kentucky.
So everything above is how our sexual relationship started, so let me get to the best weekend we ever had now. Like I said we were driving down to Louisville for a mustang car show, one of the deals we made for me driving him down there was I would get to fuck him both nights we were down there. The entire drive down to Kentucky all I could think about was how bad I just wanted to fuck my friend really hard. While in the car I started talking about what we were going to do that weekend and I finally got to the subject of me making passionate love to him. I asked him if he enjoyed me fucking him, and he said "of course not, I just want the money" but in my heart I knew he had to enjoy the sex. I started telling him that I was going to fuck him nice and easy at first and then I was really going to pound my cock into his ass and make it hurt. For some reason I always enjoyed just plowing the hell out of him and trying to make it hurt as much as I could, I'm not really sure why. I mean usually when you're making love to another person you want it to be fun and relaxing for both people, but I think because I was paying him for sex that I wanted him to always remember each fuck session we did.
While still driving all of a sudden he made a comment to me "hey why don't we switch places this weekend?" I was floored on what I just heard; I could hardly believe what he just said. Just to make sure I said "what" he responded and said "you heard me let's change places." I said "ok if that is what you want to do, I would be glad to change places but I'm still going to plow your ass myself." After the 4 hour drive we finally got to the hotel, it was a Friday night and kind of late.
We stayed up for a while and watched TV, I then started to get really horny and my cock was hungry for his tight ass. So I went up to him and told him to start getting undressed while I use the restroom, by the time I come out I want you naked. What he didn't know was that I was going into the restroom to jack off really quick so then I could last longer when I was pounding his ass. After a few minutes of jacking off in the bathroom I came out and he was stark naked, he even had his shirt off for once. I figured if he had his shirt off then he was really wanting it, so I thought this would be an excellent time to try new things with my friend. I got undressed quickly and stood before him and grabbed onto his 7 inch cock, yes it was now a couple years later so he has developed a very nice cock and very hairy balls I might add. He started to get hard with my hand on his cock; I said "wow Brian you're really getting hard with me touching your cock." I then reached around and moved my fingers up the crack of his nice ass, oh and what a beautiful ass he had.
I then asked him "have you ever had a blowjob?" He said "no but I have always wanted one" well I said "today is your lucky day, I'm going to suck your cock like a popsicle." With that I made him sit on the bed while I kneeled down and took his rock hard 7 inch cock in my mouth, now this was the first time I have ever gave a guy a blowjob so I definitely had some trouble taking his entire cock in my mouth. While I sucked on his cock, he put his hand on top of my head and pushed me down to take more...I must have sucked on his cock for a good 10 minutes until he finally blew his load in my mouth. I think he was in a totally different world after he blew his load; he was just lying back on the bed and looking at the ceiling like he just died and went to heaven.
I got on the bed and turned him over so I could give him a nice back rub, like I always did before we made love. He would always insist that I give him a back rub before I would start fucking him, I think it just made him more comfortable and calmed his nerves as well. After giving him a back rub for about 20 minutes and fondling his ass I got up off the bed and went to go smoke a cigarette. This was pretty much our ritual that I would give him a back rub for a while, I then had a cigarette and I mentally prepared for how I was going to fuck the daylights out of my friend.
The rest of the story will come in Chapter 2. Happy reading. If you enjoyed the story so far please email me at bribchlr25@hotmail.com