Winston was my best friend's sister's boyfriend. It was very unexpected that we would have sex on the first night we meet. It was totally unexpected all the way around. Winston stood about 5'11" medium brown complexion, boxer built, nice shoulders, arms and not an ounce of flab anywhere that I could see. He had light brown eyes that you could get lost in (those bed room eyes), short light brown hair with a natural curl to it, that he kept short in a box cut, trimmed on the sides but not too short. Hands like a boxer with the sweetest lips that were made for kissing. I too stood 5' 11" brown complexion, slender built all the way around, black hair, brown eyes and a killer smile (just one of me greatest assets, at that time). I was 17 and he was 20 and I had just finish high school, getting ready for college.
This happened one summer night in June, a few weeks after graduation, at my house, in the backyard. It was a clear summer nights that had this warm breeze to it. When the wind blew, you could smell the aroma of the flowers and grass that had been cut earlier that day and the smell of the water that was sprayed on it that evening. Like there was rain in the air, fresh and clean. We meet at my best friend's house one Sunday evening and as the night went on, I decided to leave and go home. Winston had decided to leave also and said that he would walk with me. We said our good nights and off we went walking and talking about nothing really. As we walked, we talked about things in general like how long I had lived in the neighborhood, but didn't seen him around and that I did not know that he was seeing my best friend's sister. While talking, Winston told me about how long he had known my friend and his family and that he is dating the sister. Since this was my first time seeing him, he went on to tell me why he was around much. He told me that he had spent some time in Juvenal Hall and once he turned 18, he was sent to jail (prison) to finish out his time. I wanted to ask him what did he do to get sent there, but I thought better of it. He was released just a few weeks ago and came to by see his girlfriend. Now, I understand why I haven't seen him around the neighborhood much. As we continue to talk, I felt this strange but yet comfortable feeling being around him. So, I went on and told him that I was about to embark onto college and how much I was looking forward to it, since this would be my first time away from home. Not seeing him before that night or him seeing me and not knowing much about him, I guess he thought I had an interest in his girlfriend.
Now even though I knew that I was gay and had known a very early age, I kept a very low profile about my sexuality even around best friend's, his family and everyone else for that matter or so I thought. For all they knew I was just another straight guy living in the neighborhood hanging out with my friend, even though I was doing my own thing with a few of the guys from school and a few that lived in your neighborhood (smile). So, I told Winston that I had no interest in my best friend's sister and that we just were good friends. Winston asked me about girls and if I liked them. I told him that girls' were O.K., and I had a girlfriend while I was in high school, but we stopped see each other right before graduation, Winston just smiled. He asked me why did we stop seeing one another. I told him that it just did not feel right, so I talked to her about it and she agreed. As it turned out, she had already started to see (date) someone else. So, he asked me how did I feel about that? I told Winston, that it did not bother me and it took some of the pressure off of me "having to like her" or "pretend to like her", or giving her any hope that it would go any further.
So, with that, I thought I had put his mind at ease. But little I did not know, Winston had peeped my "hole" card and read exactly what was on my mind. Then all of a sudden, the conversation went in another direction, he "flip the script" on me. He started asking me questions, about my best friend and if we had something going on. I looked at him as if he had two heads with my head cocked to one side with an eyebrow raised, (I could feel my face getting flustered) and told him that we are friends, best friends, that's when Winston smiled and said, "It O.K. I know that you are gay and I just want to know if you and your "best friend" are doing something?" Well, if you could have seen the look on my face (I tried to keep my sex life a secret and under control thinking that it would be hard for someone to guess or even wonder if I was gay), you could have knocked my over with a feather. With my mouth slightly open, Winston reached over and gently pushed my chin up to close my mouth, and continued to ask questions, like if I am not having sex with my best friend, then who?
By that time we were at my house, new I was a little dazed and confused, we sat on the front steps and continued our conversation, by now it was about 11:00 p.m. Sunday night. I was shocked and surprise! Here's this fine, stocky, sexy man, talking to me about who I am doing? What the heck is going on? How could he tell? Maybe it was the fact that he had been in jail and knew the "signs" to look for or was it that I was so excited that this guy is talking to me and knew I was attracted to him by the way my tongue was hanging out of my mouth (drip, drip). I don't know? But, Winston just looked at me and smiled every time he asked a question. When I realized that I was busted, the smile got bigger and he would look me straight in the eyes. I was sooo lost in those eyes of his and then I felt my dick coming to life in my shorts and not knowing what to do. I couldn't just say good night and get up right into the house, but damm! He would see this bulge in my shorts and I would die from embarrassment, then again, if he continues with this conversation and it heads in the right direction, my harden cock would no longer matter, cause he would have one too and I would be happy, no thrilled to take care of his right away.
We would have to move this conversation somewhere else and in a hurry.
So, here we were sitting on the steps of my front porch and the conversation started to get little steamy. Winston moved in for the kill by getting closer and telling me how intriguing I am and saying all the things he wanted to do to me. I was floored, as he went on, he said, "I had to find out what you were about and to see if you felt the same about me!" Well, while he was talking, all I could do was look into those sexy, light brown "bedroom eyes" of his and breathe hard. My cock was getting harder and dripping pre-cum all into my shorts (damm!!!). If he had reached out and touch me right at that moment, I would have exploded in my white "FTL" jockeys right then and there. I just wanted to reach over and plant a kiss on those lips and slide my hands down in his khaki and grab hold of what I was about to receive.
A nice breeze came along with the sweet smell of the honeysuckle, roses and carnations in my mother's front garden filled the air. The heat that was coming from our body just intensified the aroma that was around us. Sweat started to form on our faces, chest and backs. I was so lost in those eyes and getting hotter by the second, knowing I was about to go on a ride of my life, with my best friend's sister's boyfriend. Then my brain stopped and said, "What the hell are you doing"? I could not answer. I snapped back to reality and all I could see again was his eyes. I spoke by saying I was as interested in him as he was in me. I told him that I hope this would not come get back to his girlfriend. Winston said, "She would never know." "I want tell", unless you tell her brother"? With this smile on his face (again, damm!!)
As we stood up, I could see the imprint of his cock in his khaki pants and it looked like he was packing a monster of a cock in there and he too was dripping pre-cum. I could see the wet spot that had formed on the front of his khaki, as we stepped down the stairs from the front porch and started to walk into the backyard where there were chairs and a picnic table, and I said to myself, "Damm, he is hottttt!" We started walking up the driveway into the backyard, Winston grabbing my hand and squeezed it lightly as we proceeded towards table and chairs. And that's when it all happened, Winston spun me around to face him and started kissing me on the lips, to which I had no problem returning the jester. He walked me backwards to the wall of the house where he pressed me against it and kissed me long and hard. It was such a great feeling having my lips pressed up against those sweet sexy lips and our mouths opened and our tongues did their dance. They did that Indian thumb wrestle and his tongue won hands down. Winston stuck his tongue into my mouth and it seemed like he was trying to tickle my uvula (that little piece of flesh that hangs in the back of our throat) and I went with the flow, taking in deep breaths as he laid those lips on me. I saw stars and was so thrilled that this was happening.
I started to felt bad being with him at first, cause I knew his girlfriend and besides, her brother was my best friend. But as he deep throat me with his tongue, the thought soon went away. It felt soooo good; I did not want to stop. Winston moved his hands up and down my back, I thought to myself, if this how he kisses his girlfriend, "she is one luck ass!" Again, the thought of her came into my mind and her brother too. I was getting so turned on from him kissing me, Winston pulled me away from the wall and pulled me in even closer as we stood there. If he had pulled me any closer, he would have been standing on the other side of me. I could really feel his now rock hard cock pressing up against my leg and I know he could feel my now raging cock pressing up against him. I could tell that they (our cocks) wanted some very much attention and they wanted to be free of their confinement. The heat from our bodies did not make things any better. Winston moved his hands slowly down my back to my ass and started to squeeze gently. The next thing that came to mind was that commercial for Charmin's toilet tissue, about "please don't squeeze the Charmin's", but it was hard to resist. With my arms wrapped around his neck and holding him, every time he would squeeze my cheeks, I would tighten my grip around his neck. We kissed and he groped for what seemed like hours, but time was moving very slowly for us that night. Cause I knew that there was more to come and I would have one of the best nights of my life and was very sure that there were more to come.
He let me come up for air, while still squeezing my ass and then moved those kissable lips of his lips on my neck and the felling was so great. The heat from his mouth on my neck just got me hotter and I started to moan with delight. I let go of his neck and started playing music up and down his back to which set him off to moaning and grinding his cock in to my leg. I could feel my cock twitching aching to get free and I hope his wanted the same. So, I moved one hand between us so, I could get a feel and rub that hot pre-cum dripping cock. When I touch it, he moaned louder and said, "Fuck!" I was ready to take that bad boy into my hungry and waiting mouth and do a job on it. We stepped back from one another and I went for the gold, by unzipping his khaki and letting his cock free. He grabbed the bottom my polo shirt and pulled it over my head and started sucking my right nipple and I fell to the ground. "Fuck", he said I think he just messed me up when he did that, which he did. Winston helped me off the ground and asked if I was all right, I said yea, and he smiled at me and kissed me on the lips. I had to rush to get his cock out of his pants, before he suck on my nipple again. I looked down and his cock was waiting for me to take it into my hungry mouth. I went down with my mouth open to suck it right in. He had to be about 9 inches, uncut, thick and with a basket of light brown hair. I reached for it and it twitched with pre-cum dripping from the covered head. I took the skin that covered the head of his cock and slid it back slowly, Winston moaned again. I sucked the head of his cock and tasted his pre-cum for the first time and it had that bittersweet taste to it.
As I took more of his cock into my mouth, Winston grabbed my head and started to fuck my mouth. Slowly at first, but each time he would move his hips forward so I could get more of his cock into my mouth he would moan again and pick up speed. Winston was fucking my mouth and I loved every minute of it. I would deep throat his cock and that just made him hotter and moan louder. He was saying things like "Oh shit, oh shit", Suck that dick, suck it". While he was saying all of that, I had my cock in my hand pumping for dear life. I would come up for air every now and then, but I want to feel Winston's cock exploded in my mouth and drink every ounce of cum he was able to produce. I felt myself about to climax and tried to hold it back and wait for him so we would cum together. I let go of my cock and grabbed hold of his ass and pulled him in as close as possible to where my face and nose was all in his hot, sweaty pubic hair and the aroma just got to me. It was all up in my nose and I could not help but to breathe it in. Then with out touching my own rod, I shot my load right there between his legs on the ground. I was spent, I was done for, but I keep sucking away and holding on for dear life. His cock started to swell in my mouth and I knew he was about to let me drink the juices that he was storing for me. Winston brought my head in as close as possible, I got another whiff of his now even hotter and sweaty pubic area and he then said, "I'm cumming, I'm cumming". And oh boy did he cum. The force of his load hit the back of my throat, that I started to gag, but my reflexes kick in and I bagged off of his cock just enough it would shoot down my throat. I drank him, like you would drink an ice-cold beer on one of those hot summer days. After his cock started to go soft, I suck on it to get the very last drop. He gently pushed my head back, smiled and asked if I was trying to suck up his balls dry. I let it slip out of my mouth smiled. Winston smiled back and said, "Next time". But the next time we get together, I wanted him to fuck me with the 9 inch, thick dick of his.
He helped me up form the ground as I was tucking everything way of mine (smile) and told him that I would look forward to the next time. We continued dressing and he kissed me on the lips, tasting his own sweet juices and hugged me real tight. We walked from the backyard and returned to the steps of the front porch. We talked a little more and then he kissed me good night. As he walked away, he turned smiled and said, "Until next time!"
To be continued:
If you like my stories, please let me know. I would appreciate your feedback. Kenny