OsirisRider019
On the Prowl
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- Jul 22, 2007
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So I’ve always led a very straight life. Have had plenty of girlfriends over the years. Actually haven’t had much single time at all since entering high school. I consider myself pretty lucky, and blessed to be a good looking guy. Ever since my body really filled out, around my sophomore year in HS, I was practically fighting off the ladies, and in some occasions, the boys.
I remember during my senior year summer, I was still dating this girl I had been with since the junior prom. Things were going real well but I felt I needed something else... something was missing in my sex life. Had always fantasized about being with another man, but that stuff didn’t fly with my friends/family. I decided telling my girlfriend was the best route in getting some of these feelings out. I danced around the issue a little bit before telling her but when I finally did, it felt really good. I'm not sure exactly what I said but it was something along the lines of I was comfortable calling another man hot, or being completely attracted to him... just in a sexual kind of way.
She was a little put off by all this at first (probably because she knows all my friends and she wouldn’t suspect me to feel like that) but then she really warmed up to the idea of me being with another guy. She, being a recent HS grad had of course, had a few homosexual experiences with her friends... but no one thinks twice about a few girls getting naughty together haha. So she began opening up to me a little more, now that we were spilling our deepest secrets. She told me that it really turned her on either having bisexual group sex with another couple, or just straight up watching me with another guy. We started throwing some names around of people who may be interested in such a gathering, but no one we knew directly really came to mind. So we put the idea aside for a bit until we could figure out how to go about it.
A few days later I was with her and the topic came up again, this time while we were with a small group of her friends. I was slightly uncomfortable with her blurting some of this stuff out in front of these people that I didn’t know very well, but it turned out to be the right move. She had talked with a couple of her friends she could trust, and we were put on to this kid Keith who I actually knew. Apparently he was pretty much out of the closet bi already, and since we both already knew him we figured it couldn’t hurt to at least ask him. I knew this guy from years before when we were on the same lacrosse team. From what I remembered about him he had a great body and was really in shape. Very cute features, long hair... almost a surfer boy look...
So me and Kim (my gf) stuck around with that group for the day, knowing that Keith would eventually be showing up to the party we were at. Sure enough after a couple hours of just hanging out and drinking, he showed up. By this time the party was in full gear, about 45 people from my grad. class roaming around and trashing this house. Kim wasted no time in seeking him out and bringing him aside once he had a few in him. I tried to be as casual as possible; trying to act like my gf wasn’t asking this guy if he wanted to get naked with us ha-ha. After a few minutes of them talking outside, they came back in and Kim signalled to me like she was ready to leave. I went back outside to where I was parked and Keith was already out at my car with a shy grin on his face. Kim came out and yelled back to everyone that we were going to go smoke a joint along the beach road.
Once we got in the car, Kim was practically out of control... pretty wasted and incredibly horny. Keith seemed a little quiet but definitely down for the cause. We went back to Kim's where there was no one home and plenty of space
We made a few drinks once we got there, then Kim broke the awkward silence with "so, when are you guys gonna fuck for me?" Keith and I started laughing and blushing a bit, but then it was like... yeah, when are we gonna do this lol...
So Kim brought us up to the 3rd floor where her room was and immediately stripped down to her bra and panties. Sat down in the chair across from her bed and said something like "now it’s your turn" as she signalled towards the bed. Keith, at this point knowing he was beyond the point of return I guess turned from shy soccer boy, to amateur porn star lol. He started getting undressed in front of me slowly so I figured I should do the same. As I was getting just my pants off, I looked up and he was already ass naked, cock rock hard! I was like, wow, that was fast... I thought we were gonna get down to our boxars first lol. So I took the hint and did the same. Meanwhile Kim has shed any jitters that she may have had, and had her panties pushed aside as she fingered herself. So she was having her fun, it was time now for us.
I pushed Keith down to the bed and grabbed his huge throbbing cock. I'd have to say it was about 8in, just a tad bit bigger than mine I think. Being really inexperienced with guys at the time, I remember thinking... now what?? I wasn’t totally sure what to do, but when I grabbed it, I could see in Keith's face that just I touching his cock was driving him wild. So I jerked him off a bit, stopping to slow down and spit on his cock to lube it up in my hand, letting him stare down at me and he practically begged for head. So I knew it was time to let him have it. I wrapped my mouth around his cock and his whole body jerked a little bit... he almost choked me with his huge dick! After just a couple of minutes of sucking him off he pulled his cock out of my mouth and said he was about to cum. He didn’t wanna cum yet, and neither did I... so he took a breather then told me to get on the bed and spred my legs...
Here it was... I was about to get railed by a guy with a beautiful rock hard prick, and just the thought of it got me so hard it almost hurt! So I got on my back and he got right on top of me. I felt the head of his cock trying to break into my tight little ass, but it just wasn’t having it. I knew we needed lube or something to help us out. So right as I was about to ask Kim to get the lube from her nightstand, she was already there handing it to Keith. He wasted no time lobbing up his cock and going right back at it. Once he did that there was no problems... he slid right in as I gasped... it hurt for like 2 seconds, then that pain turned to euphoria. I saw how good it felt to him as the thrusts started getting faster and faster. I let him fuck me like that for about 5 or 6 min until I wanted to change positions.
I had him pull out of me, I switched around to my hands and knees and he knew exactly what I wanted. I presented my nice tight ass to him and he plowed right into me with a vengeance! It felt so good; I just wanted to feel him blast his load all inside me. I felt the condom had busted, and he was now sliding in and out a lot easier. We stopped for a sec so he could get the condom off, and he assured me he was clean. So being in the heat of the moment, I told him to finish fucking me bareback. It felt even better with just his unwrapped cock plunging into me, it was so hot and he was hitting my hole so deep. Kim burst out a couple times with some orgasmic screams, as she was having the best night of her life watching her boyfriend get fucked. I didn’t see it but she swears that she squirt all over the place when she saw Keith cumming in me. He grabbed a hold of my shoulders really tight and yelling I’m cumming!! I pressed my ass back at him as hard as I could, sending him as deep as he'd been in me as he blew his load. He must have cum a gallon because I felt it immediately. Just a hot burst of cum, then another, and another. He finally pulled out, and as he did I felt some cum drip out and down my leg. He almost looked a bit ashamed for a moment and I giggled. Kim was still hard at work on herself when he realized I hadn’t cum yet. I was surprised that he did it but he went right down on me without saying a word. Sucked my cock for a few minutes, then Kim came over and helped out with the job. This was maybe 15-20 min after Keith cumming in me; I blew my load in Kim’s mouth while he jerked off next to us. Blowing his second load right about when we were finished.
We all ended up going back to where we were earlier and acted like nothing ever happened Since then me and Keith have hooked up a few times randomly... But I will always remember that first time so vividly
I remember during my senior year summer, I was still dating this girl I had been with since the junior prom. Things were going real well but I felt I needed something else... something was missing in my sex life. Had always fantasized about being with another man, but that stuff didn’t fly with my friends/family. I decided telling my girlfriend was the best route in getting some of these feelings out. I danced around the issue a little bit before telling her but when I finally did, it felt really good. I'm not sure exactly what I said but it was something along the lines of I was comfortable calling another man hot, or being completely attracted to him... just in a sexual kind of way.
She was a little put off by all this at first (probably because she knows all my friends and she wouldn’t suspect me to feel like that) but then she really warmed up to the idea of me being with another guy. She, being a recent HS grad had of course, had a few homosexual experiences with her friends... but no one thinks twice about a few girls getting naughty together haha. So she began opening up to me a little more, now that we were spilling our deepest secrets. She told me that it really turned her on either having bisexual group sex with another couple, or just straight up watching me with another guy. We started throwing some names around of people who may be interested in such a gathering, but no one we knew directly really came to mind. So we put the idea aside for a bit until we could figure out how to go about it.
A few days later I was with her and the topic came up again, this time while we were with a small group of her friends. I was slightly uncomfortable with her blurting some of this stuff out in front of these people that I didn’t know very well, but it turned out to be the right move. She had talked with a couple of her friends she could trust, and we were put on to this kid Keith who I actually knew. Apparently he was pretty much out of the closet bi already, and since we both already knew him we figured it couldn’t hurt to at least ask him. I knew this guy from years before when we were on the same lacrosse team. From what I remembered about him he had a great body and was really in shape. Very cute features, long hair... almost a surfer boy look...
So me and Kim (my gf) stuck around with that group for the day, knowing that Keith would eventually be showing up to the party we were at. Sure enough after a couple hours of just hanging out and drinking, he showed up. By this time the party was in full gear, about 45 people from my grad. class roaming around and trashing this house. Kim wasted no time in seeking him out and bringing him aside once he had a few in him. I tried to be as casual as possible; trying to act like my gf wasn’t asking this guy if he wanted to get naked with us ha-ha. After a few minutes of them talking outside, they came back in and Kim signalled to me like she was ready to leave. I went back outside to where I was parked and Keith was already out at my car with a shy grin on his face. Kim came out and yelled back to everyone that we were going to go smoke a joint along the beach road.
Once we got in the car, Kim was practically out of control... pretty wasted and incredibly horny. Keith seemed a little quiet but definitely down for the cause. We went back to Kim's where there was no one home and plenty of space
We made a few drinks once we got there, then Kim broke the awkward silence with "so, when are you guys gonna fuck for me?" Keith and I started laughing and blushing a bit, but then it was like... yeah, when are we gonna do this lol...So Kim brought us up to the 3rd floor where her room was and immediately stripped down to her bra and panties. Sat down in the chair across from her bed and said something like "now it’s your turn" as she signalled towards the bed. Keith, at this point knowing he was beyond the point of return I guess turned from shy soccer boy, to amateur porn star lol. He started getting undressed in front of me slowly so I figured I should do the same. As I was getting just my pants off, I looked up and he was already ass naked, cock rock hard! I was like, wow, that was fast... I thought we were gonna get down to our boxars first lol. So I took the hint and did the same. Meanwhile Kim has shed any jitters that she may have had, and had her panties pushed aside as she fingered herself. So she was having her fun, it was time now for us.
I pushed Keith down to the bed and grabbed his huge throbbing cock. I'd have to say it was about 8in, just a tad bit bigger than mine I think. Being really inexperienced with guys at the time, I remember thinking... now what?? I wasn’t totally sure what to do, but when I grabbed it, I could see in Keith's face that just I touching his cock was driving him wild. So I jerked him off a bit, stopping to slow down and spit on his cock to lube it up in my hand, letting him stare down at me and he practically begged for head. So I knew it was time to let him have it. I wrapped my mouth around his cock and his whole body jerked a little bit... he almost choked me with his huge dick! After just a couple of minutes of sucking him off he pulled his cock out of my mouth and said he was about to cum. He didn’t wanna cum yet, and neither did I... so he took a breather then told me to get on the bed and spred my legs...
Here it was... I was about to get railed by a guy with a beautiful rock hard prick, and just the thought of it got me so hard it almost hurt! So I got on my back and he got right on top of me. I felt the head of his cock trying to break into my tight little ass, but it just wasn’t having it. I knew we needed lube or something to help us out. So right as I was about to ask Kim to get the lube from her nightstand, she was already there handing it to Keith. He wasted no time lobbing up his cock and going right back at it. Once he did that there was no problems... he slid right in as I gasped... it hurt for like 2 seconds, then that pain turned to euphoria. I saw how good it felt to him as the thrusts started getting faster and faster. I let him fuck me like that for about 5 or 6 min until I wanted to change positions.
I had him pull out of me, I switched around to my hands and knees and he knew exactly what I wanted. I presented my nice tight ass to him and he plowed right into me with a vengeance! It felt so good; I just wanted to feel him blast his load all inside me. I felt the condom had busted, and he was now sliding in and out a lot easier. We stopped for a sec so he could get the condom off, and he assured me he was clean. So being in the heat of the moment, I told him to finish fucking me bareback. It felt even better with just his unwrapped cock plunging into me, it was so hot and he was hitting my hole so deep. Kim burst out a couple times with some orgasmic screams, as she was having the best night of her life watching her boyfriend get fucked. I didn’t see it but she swears that she squirt all over the place when she saw Keith cumming in me. He grabbed a hold of my shoulders really tight and yelling I’m cumming!! I pressed my ass back at him as hard as I could, sending him as deep as he'd been in me as he blew his load. He must have cum a gallon because I felt it immediately. Just a hot burst of cum, then another, and another. He finally pulled out, and as he did I felt some cum drip out and down my leg. He almost looked a bit ashamed for a moment and I giggled. Kim was still hard at work on herself when he realized I hadn’t cum yet. I was surprised that he did it but he went right down on me without saying a word. Sucked my cock for a few minutes, then Kim came over and helped out with the job. This was maybe 15-20 min after Keith cumming in me; I blew my load in Kim’s mouth while he jerked off next to us. Blowing his second load right about when we were finished.
We all ended up going back to where we were earlier and acted like nothing ever happened
Since then me and Keith have hooked up a few times randomly... But I will always remember that first time so vividly 
