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My first time (true story)

Hammy75

Virgin
Joined
Jun 14, 2017
Posts
39
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Location
Saint Louis
This story takes place a little over ten years ago. I was recently divorced and moving into a nice apartment complex to try and pick up the pieces of my newly shattered life. Who knows? Maybe I was vulnerable at the time and easily coerced into this, but I have no regrets about what transpired or my life since.

It was moving day. I had a couple of friends to help me with the bigger things, but they all couldn't stay long. I was left to handle the rest on my own. Enter Jim, one of my new neighbors. He was an older gentleman, I would've guessed at least 10 years my senior. He happened to be coming home from somewhere and saw me unloading the truck solo. "Do you need some help?" he said as he walked by. I'm not one to accept help from strangers, but I was wearing down and there was still a lot to unload. I accepted his help. He turned out to be a huge help, he stayed until the truck was completely empty. I offered him dinner as a thank you, but he declined, saying that he already had dinner plans.

During the next few weeks I saw Jim periodically at the pool, which was situated right off my back patio. We would greet each other warmly every time we crossed paths, engaging in longer conversations with each meeting. To the point of us hanging out at the pool often. One conversation in particular led to my knowledge of him being gay. It didn't shock me at all, nor did I really care. He was just a really nice guy in my mind. Throughout the summer, I got to know more of my neighbors, but Jim and I became close friends. He would even tell me about who he had relations and who he wanted to have relations with.

One sunny afternoon at the pool, Jim told me about the Memorial Day pool party that was being planned. He told me that it was an annual event and the biggest pool party of the summer. There would be plenty of food, drinks and fun to go around. Very cliche, but very fun nonetheless. The party was all day, from about 11am until the last person went home. It was a blast! I met all kinds of cool people (some were not so cool) and had an overall great time. As the party winded down, Jim and I were poolside just talking. Our inhibitions were definitely lowered with all the alcohol, so our conversation got pretty heavy. He confessed that he was extremely attracted to me and fantasized about us constantly. I was a bit stunned, but very flattered. Being in straight relationships my entire life, I never thought that I would be the subject of another mans sexual fantasy. It actually started to turn me on a little. Now, I had always had a mild curiosity about being with another man, but I had never expressed it to anyone. That was one of the great things about Jim, I could easily talk about anything with him. So I told him about my curiosity.

That's where the conversation turned sexual. I started asking him question after question about being with men and he told me about a few of his sexual encounters. I didn't notice at first, but we started moving closer to each other as the conversation went on until we were practically nose to nose. The tension was clear at that point and he suggested that we go indoors. My apartment was closer so we went inside. I made us a couple of drinks, we sat on the sofa and continued our conversation. We didn't get very into it when he asked "Can I kiss you?". As nervous as I was, it didn't take me long to say yes. He put his drink down and slowly moved in, giving me a nice sensual kiss on the lips. It lasted all of 5 seconds, but it was nice. The second kiss was a little longer and a little harder than the first. The next thing I know, we're in a passionate embrace making out. I had never been kissed like that before. Normally I was the one in control of things like that with women. Jim however, was in complete control of me. I liked it.

Before long we were horizontal with Jim on top and in various stages of undress. I had succumbed to his will and was at his mercy. The pressure of his body on mine was intensely erotic, especially while grinding into each other. I could tell that my first experience was going to be memorable and defining. We then switched it up to where I was on top. This way he could reach my ass with ease. As we continued our passionate melee, his hands were kneading my ass. I even felt a finger breech my hole a few times. God was it hot, I almost couldn't control myself. He continues to work my hole and ended up 2 knuckles deep. It was bit uncomfortable at first, but soon subsided. This went on for a long time before he said "Let's go to the bedroom." I hopped of of him, led us to my room and then the real fun began.

He sat down at the edge of the bed and told me to lay down next to him. That's when I got a good look at his cock. I was mesmerized by it. At least 8 inches, somewhat thick and standing straight up. It gave me pleasure to know that I'm the reason for his erection. I laid down next to him so I was face to face with his hard cock. Before he could even finish saying "Put it your mouth", I engulfed it. Being that it was my first time sucking dick, I fumbled around a bit, but soon got the hang of it. I was working his dick when i felt a wet finger enter my hole and start sliding in and out. I almost couldn't believe what was happening. I was sucking a huge cock with a finger in my ass. Soon one finger turned into two fingers fucking me. I instinctively arched may back to allow him better access. I moaned as he worked my ass over. Initially he was a bit rougher than I'd have liked, but I settled into it fairly quickly. Then he asked "Do you want me to fuck you?". With his cock still in my mouth, all I could do was moan a "mm mm". He got up, moved behind me, spread my cheeks and gave me a feeling that was out of this world. His tongue was like magic. So much so that I thought I was going to cum right there. I got so into it that I was pushing back on his face. Finally he spit on it a couple of times, rubbed it in and did the same to his cock. "This may hurt a little at first, but you'll end up begging for it" he said as he positioned himself behind me.

An intense burning sensation fell upon me which turned into a sharp pain as he stretched my tight hole. He continually told me to relax and breathe as he very slowly entered me. Once he was all the way in, he paused for a long time and reassured me once again. He was right, the pain subsided as I relaxed and got accustomed to an 8 inch cock inside me. I think he could tell that I was now comfortable by my breathing, because he began to pump and thrust his his entire length deep into me. Slowly at first and gradually getting faster and faster. With each impact of his pelvis to my ass, I let out a tiny whimper. "Do you like that?" he asked. I could barely speak, but eventually got out the words "Dear god yes". And with that, he started to give me the fuck of my life. He flipped me on my back, held my legs out and pounded me furiously. All I could do was throw my head back and moan in ecstasy. I didn't care if anyone could hear me, all I wanted was Jim and his cock. Jim ended up being right, I was begging for it. "Fuck me!" I said over and over again. "You love this cock, don't you" he replied. I'm not sure how many times I said "YES!". but it was a lot. We ended up on our sides spooning while he impaled me and we kissed as his cock started to spasm and shoot what seemed like gallons of cum inside me. The warm feeling in my bowels felt incredible, so much so that I came shortly after.

There we were, two exhausted sweaty lumps on my bed, thoroughly satisfied. We fell asleep and continued our sexual adventure through the next week. Still turns me on to this day when I think about it.

Thanks for reading, let me know what you think.
 
This story takes place a little over ten years ago. I was recently divorced and moving into a nice apartment complex to try and pick up the pieces of my newly shattered life. Who knows? Maybe I was vulnerable at the time and easily coerced into this, but I have no regrets about what transpired or my life since.

It was moving day. I had a couple of friends to help me with the bigger things, but they all couldn't stay long. I was left to handle the rest on my own. Enter Jim, one of my new neighbors. He was an older gentleman, I would've guessed at least 10 years my senior. He happened to be coming home from somewhere and saw me unloading the truck solo. "Do you need some help?" he said as he walked by. I'm not one to accept help from strangers, but I was wearing down and there was still a lot to unload. I accepted his help. He turned out to be a huge help, he stayed until the truck was completely empty. I offered him dinner as a thank you, but he declined, saying that he already had dinner plans.

During the next few weeks I saw Jim periodically at the pool, which was situated right off my back patio. We would greet each other warmly every time we crossed paths, engaging in longer conversations with each meeting. To the point of us hanging out at the pool often. One conversation in particular led to my knowledge of him being gay. It didn't shock me at all, nor did I really care. He was just a really nice guy in my mind. Throughout the summer, I got to know more of my neighbors, but Jim and I became close friends. He would even tell me about who he had relations and who he wanted to have relations with.

One sunny afternoon at the pool, Jim told me about the Memorial Day pool party that was being planned. He told me that it was an annual event and the biggest pool party of the summer. There would be plenty of food, drinks and fun to go around. Very cliche, but very fun nonetheless. The party was all day, from about 11am until the last person went home. It was a blast! I met all kinds of cool people (some were not so cool) and had an overall great time. As the party winded down, Jim and I were poolside just talking. Our inhibitions were definitely lowered with all the alcohol, so our conversation got pretty heavy. He confessed that he was extremely attracted to me and fantasized about us constantly. I was a bit stunned, but very flattered. Being in straight relationships my entire life, I never thought that I would be the subject of another mans sexual fantasy. It actually started to turn me on a little. Now, I had always had a mild curiosity about being with another man, but I had never expressed it to anyone. That was one of the great things about Jim, I could easily talk about anything with him. So I told him about my curiosity.

That's where the conversation turned sexual. I started asking him question after question about being with men and he told me about a few of his sexual encounters. I didn't notice at first, but we started moving closer to each other as the conversation went on until we were practically nose to nose. The tension was clear at that point and he suggested that we go indoors. My apartment was closer so we went inside. I made us a couple of drinks, we sat on the sofa and continued our conversation. We didn't get very into it when he asked "Can I kiss you?". As nervous as I was, it didn't take me long to say yes. He put his drink down and slowly moved in, giving me a nice sensual kiss on the lips. It lasted all of 5 seconds, but it was nice. The second kiss was a little longer and a little harder than the first. The next thing I know, we're in a passionate embrace making out. I had never been kissed like that before. Normally I was the one in control of things like that with women. Jim however, was in complete control of me. I liked it.

Before long we were horizontal with Jim on top and in various stages of undress. I had succumbed to his will and was at his mercy. The pressure of his body on mine was intensely erotic, especially while grinding into each other. I could tell that my first experience was going to be memorable and defining. We then switched it up to where I was on top. This way he could reach my ass with ease. As we continued our passionate melee, his hands were kneading my ass. I even felt a finger breech my hole a few times. God was it hot, I almost couldn't control myself. He continues to work my hole and ended up 2 knuckles deep. It was bit uncomfortable at first, but soon subsided. This went on for a long time before he said "Let's go to the bedroom." I hopped of of him, led us to my room and then the real fun began.

He sat down at the edge of the bed and told me to lay down next to him. That's when I got a good look at his cock. I was mesmerized by it. At least 8 inches, somewhat thick and standing straight up. It gave me pleasure to know that I'm the reason for his erection. I laid down next to him so I was face to face with his hard cock. Before he could even finish saying "Put it your mouth", I engulfed it. Being that it was my first time sucking dick, I fumbled around a bit, but soon got the hang of it. I was working his dick when i felt a wet finger enter my hole and start sliding in and out. I almost couldn't believe what was happening. I was sucking a huge cock with a finger in my ass. Soon one finger turned into two fingers fucking me. I instinctively arched may back to allow him better access. I moaned as he worked my ass over. Initially he was a bit rougher than I'd have liked, but I settled into it fairly quickly. Then he asked "Do you want me to fuck you?". With his cock still in my mouth, all I could do was moan a "mm mm". He got up, moved behind me, spread my cheeks and gave me a feeling that was out of this world. His tongue was like magic. So much so that I thought I was going to cum right there. I got so into it that I was pushing back on his face. Finally he spit on it a couple of times, rubbed it in and did the same to his cock. "This may hurt a little at first, but you'll end up begging for it" he said as he positioned himself behind me.

An intense burning sensation fell upon me which turned into a sharp pain as he stretched my tight hole. He continually told me to relax and breathe as he very slowly entered me. Once he was all the way in, he paused for a long time and reassured me once again. He was right, the pain subsided as I relaxed and got accustomed to an 8 inch cock inside me. I think he could tell that I was now comfortable by my breathing, because he began to pump and thrust his his entire length deep into me. Slowly at first and gradually getting faster and faster. With each impact of his pelvis to my ass, I let out a tiny whimper. "Do you like that?" he asked. I could barely speak, but eventually got out the words "Dear god yes". And with that, he started to give me the fuck of my life. He flipped me on my back, held my legs out and pounded me furiously. All I could do was throw my head back and moan in ecstasy. I didn't care if anyone could hear me, all I wanted was Jim and his cock. Jim ended up being right, I was begging for it. "Fuck me!" I said over and over again. "You love this cock, don't you" he replied. I'm not sure how many times I said "YES!". but it was a lot. We ended up on our sides spooning while he impaled me and we kissed as his cock started to spasm and shoot what seemed like gallons of cum inside me. The warm feeling in my bowels felt incredible, so much so that I came shortly after.

There we were, two exhausted sweaty lumps on my bed, thoroughly satisfied. We fell asleep and continued our sexual adventure through the next week. Still turns me on to this day when I think about it.

Thanks for reading, let me know what you think.

SO HOT...... Was he Hot? How many guys have you been with?
 
Thank you! I thought he was very hot. He was about 6'2", in great shape and had salt and pepper hair cut short. I dated Jim for about 5 years. I dated a few guys after, but everyone since has been strictly casual. I'm seeing a younger guy now (my neighbor). He's 20, dark hair, muscular and a beast in bed. I've known him since I moved in my house, but saw him on a gay chat app about 6 months ago. He's been fucking me ever since. It's a super discreet thing, but I let him sneak over whenever he's in need. He can pound me with his throbbing cock for hours on end. He just left in fact 🍆
 
Thank you! I thought he was very hot. He was about 6'2", in great shape and had salt and pepper hair cut short. I dated Jim for about 5 years. I dated a few guys after, but everyone since has been strictly casual. I'm seeing a younger guy now (my neighbor). He's 20, dark hair, muscular and a beast in bed. I've known him since I moved in my house, but saw him on a gay chat app about 6 months ago. He's been fucking me ever since. It's a super discreet thing, but I let him sneak over whenever he's in need. He can pound me with his throbbing cock for hours on end. He just left in fact ��

How old were you guys when you first met?
 
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