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Gay Stories
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Bi-Sexual Male / 62
My Gay Awakening
I was 26 and Jack was 40 and retired early. He was best friends with my boss Joe, and we were all in the FL Keys for some R&R. Joe brought all of us (his employees) except Jack who had brought his houseboat to Duck Key. There were 8 guys as I recall and we were out to dinner that night. I was not driving and drank a lot.
After dinner we headed back to Jack’s boat to drop him off. I don’t recall exactly how, but Jack convinced me to stay on his boat that night. Even drunk, I knew where this was headed. I had been letting my boss Joe blow me weekly for about a year. But I had convinced myself I was just a straight guy enjoying some head. I had never really been with a man before, not fully, not doing all the things I secretly wanted to do since I was very young. Who knew that my curious self anal exploration as a 6 year old, using the eraser end of a pencil and some vaseline, would turn into a desire for cock. Once on his boat, Jack turned seduction into an art form. He plied me with drinks and convinced me I was tense and needed a massage….after a hot shower. Before I knew it Jack had me laying face down on his bed wearing only a white towel. I was excited for whatever was going to happen.
The massage started innocently enough, shoulders, back, legs. But soon enough, Jack’s firm hands strayed up my legs and before long the towel was off and this man was squeezing my ass with his strong hands. I couldn’t help moving my hips and lifting my ass to let him know it was his. Although he already knew. At one point my excitement overwhelmed me and I turned to look up at Jack. Before I knew what I was doing I leaned in and kissed him. His rough beard stubble was so different than the smooth warm skin of women I’d kissed. But something stirred in me at that moment, especially as my hand also wandered to his stiff cock. What had always been a fantasy desire was unfolding in real time. I was excited beyond words.
After some passionate kissing I went down on Jack’s hard cock. I paused with his cock a few inches from my mouth and said “I’ve never had a cock in my mouth”. He didn’t say a word but put a hand on my head and gently pushed me down. I opened up wide and took this man’s cock in my mouth. I had never been so sexually turned on. Pleasing a man in bed felt like a quest I’d only been imagining from the safety of my closet. But now, at least with this man anyway, I was out and wanted to play. I started sucking his cock like a starving whore and although I had no idea what I was doing he seemed to enjoy it. I rotated between sucking Jack’s cock, kissing him, and having him suck me. The only way to describe this feeling is that I found and liberated a long repressed part of me. It felt so good and so right.
At one point Jack told me he was going to fuck me (it wasn’t a question and I liked that) and grabbed a bottle of vaseline lotion and lubed my horny little asshole and his cock. I had never done this so didn’t know what to do, but went head down, ass up as i had always imagined. But Jack said no, he wanted me on my back, legs on his shoulders. I complied and almost immediately felt the tip of Jack’s steel rod against my slippery asshole. He was patient, but I wanted him. As he gently pressed in, I thrust my ass up to try and take is cock and to let him know I wanted it. Finally I just said “Go for it Jack….fuck me, oh my god please fuck me, I’ve wanted this for so long”. He needed no further encouragement and drove his cock down hard into me, burying it deep in my asshole as I let out a groan that signaled 20% pain and 80% pleasure. “Oh my god Jack” I breathlessly whispered “”I’ve needed this my whole life…..oh fuck this is so right”. Jack proceeded to pound my ass like a pile driver and I was in heaven. He switched positions a number of times and fucked me doggie style, spooning position, and then me riding him. When he was ready to shoot, Jack put me on my back again and held my legs apart and drove deep into me. His final thrusts were primal, as was his groaning growl as he said “Fuck I’m gonna cum”. I was breathing fast and raising my hips to make each thrust deeper and more powerful. Suddenly he pushed hard and held it in as I felt his big cum load pump into me over and over. “Oh fuck Jack” I said “that’s it, cum in me….cum in my ass”. When he was done I lay there, still drunk, feeling like for the first time in my life, I knew who I was. I still loved and needed pussy…a lot, but now I knew I loved and needed cock too. Jack wanted me to fuck him and cum in his ass but I was simply too drunk and I couldn’t.
The next morning Jack woke me to a pounding headache and gave me head til I came in his mouth. Wow! I still visit the Keys occasionally. When I do I always stop at Duck Key, grab a coffee, sit on a bench in front of the slip Jack’s boat was in, and remember.
After dinner we headed back to Jack’s boat to drop him off. I don’t recall exactly how, but Jack convinced me to stay on his boat that night. Even drunk, I knew where this was headed. I had been letting my boss Joe blow me weekly for about a year. But I had convinced myself I was just a straight guy enjoying some head. I had never really been with a man before, not fully, not doing all the things I secretly wanted to do since I was very young. Who knew that my curious self anal exploration as a 6 year old, using the eraser end of a pencil and some vaseline, would turn into a desire for cock. Once on his boat, Jack turned seduction into an art form. He plied me with drinks and convinced me I was tense and needed a massage….after a hot shower. Before I knew it Jack had me laying face down on his bed wearing only a white towel. I was excited for whatever was going to happen.
The massage started innocently enough, shoulders, back, legs. But soon enough, Jack’s firm hands strayed up my legs and before long the towel was off and this man was squeezing my ass with his strong hands. I couldn’t help moving my hips and lifting my ass to let him know it was his. Although he already knew. At one point my excitement overwhelmed me and I turned to look up at Jack. Before I knew what I was doing I leaned in and kissed him. His rough beard stubble was so different than the smooth warm skin of women I’d kissed. But something stirred in me at that moment, especially as my hand also wandered to his stiff cock. What had always been a fantasy desire was unfolding in real time. I was excited beyond words.
After some passionate kissing I went down on Jack’s hard cock. I paused with his cock a few inches from my mouth and said “I’ve never had a cock in my mouth”. He didn’t say a word but put a hand on my head and gently pushed me down. I opened up wide and took this man’s cock in my mouth. I had never been so sexually turned on. Pleasing a man in bed felt like a quest I’d only been imagining from the safety of my closet. But now, at least with this man anyway, I was out and wanted to play. I started sucking his cock like a starving whore and although I had no idea what I was doing he seemed to enjoy it. I rotated between sucking Jack’s cock, kissing him, and having him suck me. The only way to describe this feeling is that I found and liberated a long repressed part of me. It felt so good and so right.
At one point Jack told me he was going to fuck me (it wasn’t a question and I liked that) and grabbed a bottle of vaseline lotion and lubed my horny little asshole and his cock. I had never done this so didn’t know what to do, but went head down, ass up as i had always imagined. But Jack said no, he wanted me on my back, legs on his shoulders. I complied and almost immediately felt the tip of Jack’s steel rod against my slippery asshole. He was patient, but I wanted him. As he gently pressed in, I thrust my ass up to try and take is cock and to let him know I wanted it. Finally I just said “Go for it Jack….fuck me, oh my god please fuck me, I’ve wanted this for so long”. He needed no further encouragement and drove his cock down hard into me, burying it deep in my asshole as I let out a groan that signaled 20% pain and 80% pleasure. “Oh my god Jack” I breathlessly whispered “”I’ve needed this my whole life…..oh fuck this is so right”. Jack proceeded to pound my ass like a pile driver and I was in heaven. He switched positions a number of times and fucked me doggie style, spooning position, and then me riding him. When he was ready to shoot, Jack put me on my back again and held my legs apart and drove deep into me. His final thrusts were primal, as was his groaning growl as he said “Fuck I’m gonna cum”. I was breathing fast and raising my hips to make each thrust deeper and more powerful. Suddenly he pushed hard and held it in as I felt his big cum load pump into me over and over. “Oh fuck Jack” I said “that’s it, cum in me….cum in my ass”. When he was done I lay there, still drunk, feeling like for the first time in my life, I knew who I was. I still loved and needed pussy…a lot, but now I knew I loved and needed cock too. Jack wanted me to fuck him and cum in his ass but I was simply too drunk and I couldn’t.
The next morning Jack woke me to a pounding headache and gave me head til I came in his mouth. Wow! I still visit the Keys occasionally. When I do I always stop at Duck Key, grab a coffee, sit on a bench in front of the slip Jack’s boat was in, and remember.
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