TheRebel-JimmyDean
Slut
- Joined
- Oct 31, 2012
- Posts
- 150
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Hey guys,
Don't really have any gay friends in my life right now I can talk to about this so hopefully some of you on here can help me out. LONG POST but worth it!
Quick background. I am a 24 year old virgin. Before a few weeks ago I had never done ANYTHING (kissing included) with a man before even though I came out when I was 15. Who knows why really, a number of reasons: I'm a late bloomer, I am typically only attracted to straight guys (not into feminine acting men, at least not as someone I could look at sexually.) , always been a romantic at heart and hoped that (as cliche as this sounds) that my first time would be with someone special, Etc. So I thought, new year, new age, new me, I want to start taking action by essentially...getting some action. LOL.
So I've met up with 3 guys on Craigslist over the past month. First guy was 21, Bi, and new to men. We made out a lot (first time for me), I gave him a handjob/blowjob and he gave me a handjob. Some naked rolling around including but that was it. Second guy was a couple weeks later, he was 22, gay, (a lot cuter then the first guy). Got a little further with him. Again, lot's of making out, rolling around naked, I blew him and gave him a handjob, he blew me, fingered me and rimmed me (first time for all of those for me.) He wanted to have sex but I didn't so we skipped it. Both of these experiences I left feeling good and that they were concluded, I knew it was a one time thing and that was fine. I needed to experiment/fool around to get some practice, etc.
Going to be flagging things in BOLD that to me sounded like this next guy wanted more then a massage.
Which brings me to the point of my post (hopefully you are still reading!). Last night I answered an ad on Craigslist that a 22 year old guy posted. The title was "Massage Swap- Tonight". He said in the ad he had started working out again and had hurt his back and needed a man to massage it for free since he had gone to professional massage therapists but they were very expensive. He said he wanted a "Massage Buddy" (with the parentheses included). He said however that it would be strictly platonic because he is straight. As I was cruising Craigslist I noticed he had posted this same ad in 3 different sections on Craiglist. "Casual Encounters, Strictly Platonic and Men Seeking Men." Now I'm new to Craigslist but even I could tell you that 99% of the posts on there (especially in Men Seeking Men) are looking for sex or some kind of sex play. So we emailed back and forth for a bit, I asked him specifically what exactly he was expecting. He said only a massage, as he was straight. He then asked me if I was straight. I am pretty straightforward (no pun intended) and didn't want to lie to him or deceive him so I said I was gay and that if he only wanted a massage then that was fine with me. I also mentioned to him that he wasn't likely going to find other straight men in "Men Seeing Men" who would want to massage him for free...He said it was ok and that he still wanted to meet up. So I get his address and head over to his place...I smoke a quick bowl in the parking lot to loosing me up and relax me a bit.
He invites me in (very cute guy by the way) and we go into his spare room. He turns off the lights (it's pretty much pitch black) and gets naked and lays on the floor on his stomach. He then asks me to get naked because he said it made him feel more comfortable not being the only one naked and because he didn't like hearing things rustle around in pants pockets. Ok, I thought, whatever makes him comfortable. I strip down to my underwear and then tell him I am going to keep them on because I was likely going to get hard while massaging him and didn't want to "poke him" or make him feel awkward. He said he didn't care either way... Still I decided to keep them on anyway. He tells me that he usually falls asleep while being massaged and is a very heavy sleeper so that I need to shake him a lot to wake him up. I put on lotion and ask him where specifically I can massage him. He said full body was fine. I repeat "FULL body", with emphasis on "FULL" to make sure I heard him right. He said yes so I start massaging him, all over. It feels really nice. I get wood pretty quickly. I start rubbing his back, his legs, his ass cheeks. Do this for about 10 minutes or so til I realize he sure enough had fallen asleep. I wake him up and try to turn him over. He said he was cold and wanted to move to his bedroom. We get up and go to his room, but he said he needs it to be pitch black in order to relax so he wants me to massage him in his walk in closet with the door closed. It was a tight fit but I agreed. We go in, close the door, I literally can't see anything. He again, lays on his stomach.
Again, I massage his back, his ass, his legs for several minutes. He again falls asleep. I wake him up two more times, and each time he says he wants a little bit longer on his back and his glutes. So I keep massaging his ass (no complaints from me). I rub my fingers in and out of his crack, play around with his ass-hole, cup/massage his balls. Spread his ass a bit and smelled it (smelled clean and delicious!). I finally wake him up (again!) and he turns over. I ask him specifically what he wants me to massage, he said lower body. I asked specifically again just legs or entire lower body...he hesitates for a second, stutters, starts to say "everything", then just says "legs." I began massaging his legs for a while until I eventually start reaching close to his groin. I start to again cup/massage his balls and play around with his penis. I start slowly stroking it and naturally a few minutes later he starts to get hard. I stop stroking him and try for about 5 minutes to wake him up. I am shaking him, calling out his name, trying to flip him over, grab his arms to lift him, accidentally drop him back down. Nothing. I crack open the door to the closet to get some light in, I start flashing the light on and off in the closet. I was secretly hoping of course he'd wake up, see he had wood and ask me to finish him off.
Before I know it, I am leaning over him trying to find his head so I can try to wake him up by lifting his head. Suddenly, he grabs my arms and pulls me down on top of him. Confused, I lie there for a second before I start to push myself off of him. He then grabs my arms and pulls me down on top of him again. I start calling his name, asking him if he's awake, asking him what it is he wants from he. I thought maybe he was confused and was half asleep and thought I was his GF or something. I ask him "Do you know who I am?" No reply... I try to pull off again and Again, he pulls he down on top of him.
So at this point I'm thinking what the hell, just go for it. So I start kissing his neck and chest and eventually make my way down to his cock, which is still hard. I blow him for a bit while jacking him off. His hands start grabbing at his dick and jerking it off himself. He then pulls me up top again and lays me down on top of him. I kiss his neck, chest, etc. I do down again and lift his legs up and start rimming him. His hole was surprisingly very clean for a straight man not wanting anything more then a massage. It smells like soap and lotion and tastes yummy and cleaned out. I am maneuvering him a lot by twisting his legs around, lifting them up higher to get a better angle, etc.
I go back to sucking his dick when suddenly HE GRABS THE WAISTBAND OF MY UNDERWEAR AND PULLS IT DOWN. HE THEN STARTS JERKING ME OFF PRETTY HARD. HE SEEMS LIKE HE IS WELL AWARE OF WHAT HE IS DOING AND SHORTLY AFTERWARDS I BLOW MY LOAD ALL OVER HIS HAND/CHEST. I go back down to his cock in hopes of finishing him off. I start to suck and jack him off while playing a little bit with his hole. No penetration, just rubbing it. This goes on for a minute or two when suddenly he turns his body over to the side, making it difficult for me to suck him. Here comes the weird/confusing part of the story that I need help understanding:
I ask him "Did you finish?" He then speaks for the first time in like 15 minutes: "Finish what?" Confused, I kind of giggle and say "Nothing." He says "No, did I do something, what do you mean by finish?" So I grab his still hard dick and say "Finish this!"
Before I know it, he starts getting all flustered. "Oh no, what happened?" He grabs his phone and shines a light on himself, see's he is hard and that he has cum all over his chest. He then starts apologizing to me, saying he must had gotten hard during the massage and accidentally came all over...He said that has never happened to him before and looks really embarrassed and continues to apologize. At this point I'm thinking, HUH?! WTF?! So I just play along and I'm like "It's ok..." I then go to his bathroom to clean myself up, sporting the Cameron Diaz look with a chunk of cum in my hair (nice!). I come out, get dressed, he said his brother was on his way over so we finished just in time. He walks me to the door, thanks me, apologizes again, gives me a hug and implies we should do it again sometime. I leave, still horny but mostly just confused. Did I just like, molest this guy while he was passed out? Is he having typical straight man denial by pretending everything that just happened didn't happen? I know you can walk in your sleep. I know you can eat in your sleep. I have even heard of sleep texting. But as far as I know, most straight men don't jack off other men in their sleep and have them cum all over their chest and hand...
So long story over, hope you guys are still reading. Please, what the hell just happened? I would hate to think I took advantage of someone but part of me feels like I was the one taken advantage of (not in a bad way because I certainly had a good time and would be down to meet up with him again.)
So, what are your guys thoughts here? Did I do something wrong?
Don't really have any gay friends in my life right now I can talk to about this so hopefully some of you on here can help me out. LONG POST but worth it!
Quick background. I am a 24 year old virgin. Before a few weeks ago I had never done ANYTHING (kissing included) with a man before even though I came out when I was 15. Who knows why really, a number of reasons: I'm a late bloomer, I am typically only attracted to straight guys (not into feminine acting men, at least not as someone I could look at sexually.) , always been a romantic at heart and hoped that (as cliche as this sounds) that my first time would be with someone special, Etc. So I thought, new year, new age, new me, I want to start taking action by essentially...getting some action. LOL.
So I've met up with 3 guys on Craigslist over the past month. First guy was 21, Bi, and new to men. We made out a lot (first time for me), I gave him a handjob/blowjob and he gave me a handjob. Some naked rolling around including but that was it. Second guy was a couple weeks later, he was 22, gay, (a lot cuter then the first guy). Got a little further with him. Again, lot's of making out, rolling around naked, I blew him and gave him a handjob, he blew me, fingered me and rimmed me (first time for all of those for me.) He wanted to have sex but I didn't so we skipped it. Both of these experiences I left feeling good and that they were concluded, I knew it was a one time thing and that was fine. I needed to experiment/fool around to get some practice, etc.
Going to be flagging things in BOLD that to me sounded like this next guy wanted more then a massage.
Which brings me to the point of my post (hopefully you are still reading!). Last night I answered an ad on Craigslist that a 22 year old guy posted. The title was "Massage Swap- Tonight". He said in the ad he had started working out again and had hurt his back and needed a man to massage it for free since he had gone to professional massage therapists but they were very expensive. He said he wanted a "Massage Buddy" (with the parentheses included). He said however that it would be strictly platonic because he is straight. As I was cruising Craigslist I noticed he had posted this same ad in 3 different sections on Craiglist. "Casual Encounters, Strictly Platonic and Men Seeking Men." Now I'm new to Craigslist but even I could tell you that 99% of the posts on there (especially in Men Seeking Men) are looking for sex or some kind of sex play. So we emailed back and forth for a bit, I asked him specifically what exactly he was expecting. He said only a massage, as he was straight. He then asked me if I was straight. I am pretty straightforward (no pun intended) and didn't want to lie to him or deceive him so I said I was gay and that if he only wanted a massage then that was fine with me. I also mentioned to him that he wasn't likely going to find other straight men in "Men Seeing Men" who would want to massage him for free...He said it was ok and that he still wanted to meet up. So I get his address and head over to his place...I smoke a quick bowl in the parking lot to loosing me up and relax me a bit.
He invites me in (very cute guy by the way) and we go into his spare room. He turns off the lights (it's pretty much pitch black) and gets naked and lays on the floor on his stomach. He then asks me to get naked because he said it made him feel more comfortable not being the only one naked and because he didn't like hearing things rustle around in pants pockets. Ok, I thought, whatever makes him comfortable. I strip down to my underwear and then tell him I am going to keep them on because I was likely going to get hard while massaging him and didn't want to "poke him" or make him feel awkward. He said he didn't care either way... Still I decided to keep them on anyway. He tells me that he usually falls asleep while being massaged and is a very heavy sleeper so that I need to shake him a lot to wake him up. I put on lotion and ask him where specifically I can massage him. He said full body was fine. I repeat "FULL body", with emphasis on "FULL" to make sure I heard him right. He said yes so I start massaging him, all over. It feels really nice. I get wood pretty quickly. I start rubbing his back, his legs, his ass cheeks. Do this for about 10 minutes or so til I realize he sure enough had fallen asleep. I wake him up and try to turn him over. He said he was cold and wanted to move to his bedroom. We get up and go to his room, but he said he needs it to be pitch black in order to relax so he wants me to massage him in his walk in closet with the door closed. It was a tight fit but I agreed. We go in, close the door, I literally can't see anything. He again, lays on his stomach.
Again, I massage his back, his ass, his legs for several minutes. He again falls asleep. I wake him up two more times, and each time he says he wants a little bit longer on his back and his glutes. So I keep massaging his ass (no complaints from me). I rub my fingers in and out of his crack, play around with his ass-hole, cup/massage his balls. Spread his ass a bit and smelled it (smelled clean and delicious!). I finally wake him up (again!) and he turns over. I ask him specifically what he wants me to massage, he said lower body. I asked specifically again just legs or entire lower body...he hesitates for a second, stutters, starts to say "everything", then just says "legs." I began massaging his legs for a while until I eventually start reaching close to his groin. I start to again cup/massage his balls and play around with his penis. I start slowly stroking it and naturally a few minutes later he starts to get hard. I stop stroking him and try for about 5 minutes to wake him up. I am shaking him, calling out his name, trying to flip him over, grab his arms to lift him, accidentally drop him back down. Nothing. I crack open the door to the closet to get some light in, I start flashing the light on and off in the closet. I was secretly hoping of course he'd wake up, see he had wood and ask me to finish him off.
Before I know it, I am leaning over him trying to find his head so I can try to wake him up by lifting his head. Suddenly, he grabs my arms and pulls me down on top of him. Confused, I lie there for a second before I start to push myself off of him. He then grabs my arms and pulls me down on top of him again. I start calling his name, asking him if he's awake, asking him what it is he wants from he. I thought maybe he was confused and was half asleep and thought I was his GF or something. I ask him "Do you know who I am?" No reply... I try to pull off again and Again, he pulls he down on top of him.
So at this point I'm thinking what the hell, just go for it. So I start kissing his neck and chest and eventually make my way down to his cock, which is still hard. I blow him for a bit while jacking him off. His hands start grabbing at his dick and jerking it off himself. He then pulls me up top again and lays me down on top of him. I kiss his neck, chest, etc. I do down again and lift his legs up and start rimming him. His hole was surprisingly very clean for a straight man not wanting anything more then a massage. It smells like soap and lotion and tastes yummy and cleaned out. I am maneuvering him a lot by twisting his legs around, lifting them up higher to get a better angle, etc.
I go back to sucking his dick when suddenly HE GRABS THE WAISTBAND OF MY UNDERWEAR AND PULLS IT DOWN. HE THEN STARTS JERKING ME OFF PRETTY HARD. HE SEEMS LIKE HE IS WELL AWARE OF WHAT HE IS DOING AND SHORTLY AFTERWARDS I BLOW MY LOAD ALL OVER HIS HAND/CHEST. I go back down to his cock in hopes of finishing him off. I start to suck and jack him off while playing a little bit with his hole. No penetration, just rubbing it. This goes on for a minute or two when suddenly he turns his body over to the side, making it difficult for me to suck him. Here comes the weird/confusing part of the story that I need help understanding:
I ask him "Did you finish?" He then speaks for the first time in like 15 minutes: "Finish what?" Confused, I kind of giggle and say "Nothing." He says "No, did I do something, what do you mean by finish?" So I grab his still hard dick and say "Finish this!"
Before I know it, he starts getting all flustered. "Oh no, what happened?" He grabs his phone and shines a light on himself, see's he is hard and that he has cum all over his chest. He then starts apologizing to me, saying he must had gotten hard during the massage and accidentally came all over...He said that has never happened to him before and looks really embarrassed and continues to apologize. At this point I'm thinking, HUH?! WTF?! So I just play along and I'm like "It's ok..." I then go to his bathroom to clean myself up, sporting the Cameron Diaz look with a chunk of cum in my hair (nice!). I come out, get dressed, he said his brother was on his way over so we finished just in time. He walks me to the door, thanks me, apologizes again, gives me a hug and implies we should do it again sometime. I leave, still horny but mostly just confused. Did I just like, molest this guy while he was passed out? Is he having typical straight man denial by pretending everything that just happened didn't happen? I know you can walk in your sleep. I know you can eat in your sleep. I have even heard of sleep texting. But as far as I know, most straight men don't jack off other men in their sleep and have them cum all over their chest and hand...
So long story over, hope you guys are still reading. Please, what the hell just happened? I would hate to think I took advantage of someone but part of me feels like I was the one taken advantage of (not in a bad way because I certainly had a good time and would be down to meet up with him again.)
So, what are your guys thoughts here? Did I do something wrong?
if for some reason he still pretends he's asleep then after you make him cum, clean him up and throw the condom away or collapse together and sleep with him till morning. 
I wanted to do a good job at it.'
