"...are you gay/bi or not? it's been 6 years my god!..."
I had a funny experience last friday, but first let me give you some background information about the guy...
When I went to Italy, my best friend started dating a random guy here which I met when I came back, I met him and his young brother and ever since I first saw him ( the young brother ) I've had a thing for him. He was 15-16 and I was 20 at the time, they spent a lot of time in my place so we became pretty good friends, playing in the computer, talking, etc while my best friend and his brother were making out in somewhere in my house. Here's the thing, he's "straight" and I've even met some of his gf's along the years, he knows that I want to have sex with him cause I'm pretty straight forward about such things, he's known ever since we met.
One time 5 or so years ago, we had a "momment", I mean he was a hormone-driven guy like every other teenager and somewhat evil so he liked to tease me. We used to wrestle or play around in my bed but that was about it, until one day he decides to dare me. So he goes and says "what do you want to bet that I can get you hard by just whispering in your ear?" to which I reply something along the lines of: "rolando, I'm gay and I like you, of course I'm gonna get hard, now the question is what do YOU wanna bet that I can get you hard by doing the same thing?" ( I mean, I was playing those games even before he was born, lol ) to which he replies "I highly doubt it, but ok, what do you want me to bet?" so I tell him that if I can get him hard, I was going to stroke his hard cock for as long as I wanted. And he says deal.
I tell him to lay down in my bed, turn off the lights and I proceed to start whispering and moaning softly on his ear. Which quickly became me kissing his neck, his ears and then removing his shirt slowly to which he had no objections. I worked my way several times from his neck to his belly button, back and forth with my tongue or kisses, then I turned him around and worked his back, and then I turned him again and started caressing his tummy and nipples. After 5 or so minutes I say "now let's see if you're hard" and I move my hand down to his cock, he was of course, very, and we both become completely silent for a few seconds.
My hand still resting on his cock...no words were spoken but the momment was obvious, I had won the bet so I was able to stroke him for as long as I wanted. And I started to do so, every inch of my body filled with desire...I wanted so bad to undress him and finish the job...and I knew he wanted me to do so when he did nothing about me undoing the first button on his jean. He was laying on my bed, without his shirt on, with such a hardon. Enjoying it as much as I did.
*Knock* *Knock*
His brother and my best friend were knocking on my door. Our momment abruptly ended. He put his shirt on, we turned on the lights and pretended we were doing shit on the pc. His brother gaves us a weird look, and a couple of days later he called me asking me "did you have sex with my brother that day antonio?" - "I wish" was my reply and we both laughed. Nothing happened between us after that. Kuma'shy ( my ex ) was in the picture now, and since his brother was kuma's ex boyfriend at the time, we stopped hanging out for a couple of years. After kuma and I broke up, I got in touch with him again and we've been hanging out every now and then ever since.
Fast forward 6 years and here we are. My friends came over to play poker last friday ( sometimes my friends and I meet at my house for what's usually a wallet-devastating poker night for me ) and I called him up and he joined us, it got really late so I told him to spend the night, I could've easily drive him at 5 am in the morning since he lives nearby, but the thought of him in boxers sleeping next to me was too much to resist. He's not the same guy of course, aside from being older, he's had his fair share of sexual experiences now, he's matured, has changed physically and even though he's not as cute as he was when he was 15, he's still cute and has something that can lit up my sex-drive like a christmas tree instantly ( maybe not the best analogy but you get the picture )
So he did and changed into one of my sexy boxers which I carefully picked before handing them to him. They were very tight on him which made his bulge even more obvious ( shame on me, I know! ) - We go to bed and smoke a couple of cigarrettes talking about random stuff ( I wasn't paying attention really, all I was thinking was "ask me to suck you, ask me to suck you" like a broken record in my mind ) until we finally decided to call it a night and went to sleep.
Here's the thing though - I'm a heavy sleeper but if there's one thing that wakes me up very quickly is someone hugging/on top of me. I mean I'm very used to sleeping alone...so having someone there...their body heat mostly...it just wakes me up. So I did around 10 am or so. He was facing me, his right arm on my stomach and his leg on top of me or rather my cock. I was hard ( duh! ) and his leg was not helping since it was pressing against it. I moved an inch and he switched positions. So I pretended to be asleep aswell and rested my leg on top of his, and dropped my hand casually near his cock. Couple of minutes later I moved it again, this time a bit further down reaching his cock, he was also hard.
So I remove my hand but keep my leg resting on his. 10 or 15 minutes go by, I'm there trying to hold myself from not undressing him and sucking him off and suddenly he moves his left hand and rests it on my inner thigh, still for a minute or two, and then he starts caressing my inner thigh up and down going very close to my cock for a few seconds, then still again. Couple of minutes go by and he moves his hand up and rests it on my hard cock then strokes it for a couple of seconds. Then completely turns around facing my closet with his back towards me.
I laid there thinking "what the fuck was that all about?". A week later, I'm still wondering...I mean...do people do that on their sleep? Cause the times someone has stroked my cock in bed I'm either sleeping and wake up to find myself being sucked momments later by a gay friend or a boyfriend, or i'm awake and I stroke their cock back and we end up having sex. People don't stroke your inner thighs and cock and then play dead.
I was too stupid to do anything about it at the time. I guess I was waiting for him to make the first move after the stroking, but he just turned around!!! Or maybe he tried to but then got scared and that's why he turned around. Or maybe he was just really sleeping and he likes to stroke shit while he does.
I don't know yet, but I'm certainly gonna find out within the next weeks. I'm gonna invite him over and have him spend the night here. I mean it's been 6 years since our first momment. I'm tired of the chase, as exciting as they can be, I just want him to drop those pants, pull it out, so I can suck it off and we can both get it over with.
Which reminds me of his famous words after that encounter we had 6 years ago. "If I ever experiment with a guy, my first time will definetly by with antonio" ( he said that to my boyfriend at the time one day in the living room of my house )
When I went to Italy, my best friend started dating a random guy here which I met when I came back, I met him and his young brother and ever since I first saw him ( the young brother ) I've had a thing for him. He was 15-16 and I was 20 at the time, they spent a lot of time in my place so we became pretty good friends, playing in the computer, talking, etc while my best friend and his brother were making out in somewhere in my house. Here's the thing, he's "straight" and I've even met some of his gf's along the years, he knows that I want to have sex with him cause I'm pretty straight forward about such things, he's known ever since we met.
One time 5 or so years ago, we had a "momment", I mean he was a hormone-driven guy like every other teenager and somewhat evil so he liked to tease me. We used to wrestle or play around in my bed but that was about it, until one day he decides to dare me. So he goes and says "what do you want to bet that I can get you hard by just whispering in your ear?" to which I reply something along the lines of: "rolando, I'm gay and I like you, of course I'm gonna get hard, now the question is what do YOU wanna bet that I can get you hard by doing the same thing?" ( I mean, I was playing those games even before he was born, lol ) to which he replies "I highly doubt it, but ok, what do you want me to bet?" so I tell him that if I can get him hard, I was going to stroke his hard cock for as long as I wanted. And he says deal.
I tell him to lay down in my bed, turn off the lights and I proceed to start whispering and moaning softly on his ear. Which quickly became me kissing his neck, his ears and then removing his shirt slowly to which he had no objections. I worked my way several times from his neck to his belly button, back and forth with my tongue or kisses, then I turned him around and worked his back, and then I turned him again and started caressing his tummy and nipples. After 5 or so minutes I say "now let's see if you're hard" and I move my hand down to his cock, he was of course, very, and we both become completely silent for a few seconds.
My hand still resting on his cock...no words were spoken but the momment was obvious, I had won the bet so I was able to stroke him for as long as I wanted. And I started to do so, every inch of my body filled with desire...I wanted so bad to undress him and finish the job...and I knew he wanted me to do so when he did nothing about me undoing the first button on his jean. He was laying on my bed, without his shirt on, with such a hardon. Enjoying it as much as I did.
*Knock* *Knock*
His brother and my best friend were knocking on my door. Our momment abruptly ended. He put his shirt on, we turned on the lights and pretended we were doing shit on the pc. His brother gaves us a weird look, and a couple of days later he called me asking me "did you have sex with my brother that day antonio?" - "I wish" was my reply and we both laughed. Nothing happened between us after that. Kuma'shy ( my ex ) was in the picture now, and since his brother was kuma's ex boyfriend at the time, we stopped hanging out for a couple of years. After kuma and I broke up, I got in touch with him again and we've been hanging out every now and then ever since.
Fast forward 6 years and here we are. My friends came over to play poker last friday ( sometimes my friends and I meet at my house for what's usually a wallet-devastating poker night for me ) and I called him up and he joined us, it got really late so I told him to spend the night, I could've easily drive him at 5 am in the morning since he lives nearby, but the thought of him in boxers sleeping next to me was too much to resist. He's not the same guy of course, aside from being older, he's had his fair share of sexual experiences now, he's matured, has changed physically and even though he's not as cute as he was when he was 15, he's still cute and has something that can lit up my sex-drive like a christmas tree instantly ( maybe not the best analogy but you get the picture )
So he did and changed into one of my sexy boxers which I carefully picked before handing them to him. They were very tight on him which made his bulge even more obvious ( shame on me, I know! ) - We go to bed and smoke a couple of cigarrettes talking about random stuff ( I wasn't paying attention really, all I was thinking was "ask me to suck you, ask me to suck you" like a broken record in my mind ) until we finally decided to call it a night and went to sleep.
Here's the thing though - I'm a heavy sleeper but if there's one thing that wakes me up very quickly is someone hugging/on top of me. I mean I'm very used to sleeping alone...so having someone there...their body heat mostly...it just wakes me up. So I did around 10 am or so. He was facing me, his right arm on my stomach and his leg on top of me or rather my cock. I was hard ( duh! ) and his leg was not helping since it was pressing against it. I moved an inch and he switched positions. So I pretended to be asleep aswell and rested my leg on top of his, and dropped my hand casually near his cock. Couple of minutes later I moved it again, this time a bit further down reaching his cock, he was also hard.
So I remove my hand but keep my leg resting on his. 10 or 15 minutes go by, I'm there trying to hold myself from not undressing him and sucking him off and suddenly he moves his left hand and rests it on my inner thigh, still for a minute or two, and then he starts caressing my inner thigh up and down going very close to my cock for a few seconds, then still again. Couple of minutes go by and he moves his hand up and rests it on my hard cock then strokes it for a couple of seconds. Then completely turns around facing my closet with his back towards me.
I laid there thinking "what the fuck was that all about?". A week later, I'm still wondering...I mean...do people do that on their sleep? Cause the times someone has stroked my cock in bed I'm either sleeping and wake up to find myself being sucked momments later by a gay friend or a boyfriend, or i'm awake and I stroke their cock back and we end up having sex. People don't stroke your inner thighs and cock and then play dead.
I was too stupid to do anything about it at the time. I guess I was waiting for him to make the first move after the stroking, but he just turned around!!! Or maybe he tried to but then got scared and that's why he turned around. Or maybe he was just really sleeping and he likes to stroke shit while he does.
I don't know yet, but I'm certainly gonna find out within the next weeks. I'm gonna invite him over and have him spend the night here. I mean it's been 6 years since our first momment. I'm tired of the chase, as exciting as they can be, I just want him to drop those pants, pull it out, so I can suck it off and we can both get it over with.
Which reminds me of his famous words after that encounter we had 6 years ago. "If I ever experiment with a guy, my first time will definetly by with antonio" ( he said that to my boyfriend at the time one day in the living room of my house )