The Winsome Widow Part 2
- 2 years ago
- 38
- 0
I Took Some Convincing… free porn video
I had been thinking about having sex with a man for many years. I came close multiple times. I had always come to a point where I had to choose whether or not I was going to go through with it. I had always chickened out. This time was different.
I was traveling for work. Being alone in a hotel room gives a married guy too much temptation. I jumped on Squirt and surfed around looking for some attention. That's when Jonathan instant messaged me. Jonathan was older than I was. He was in his mid 50s while I was 46. We chatted for nearly an hour. I was getting really horny as I asked him what his first experience with another guy was like. Finally, he told me that he would give me as much detail as I wanted in person if I only gave him my room number.
This was a huge step for me. I wasn't sure I could actually go through with it. But I convinced myself that if he came over to my hotel room, we would only talk about his experiences. I knew it would likely lead to something more but I thought 'more' meant that we would simply jerk off in front of one another. I had jerked off in front of other guys a few times before and it never graduated to touching or anything else. So I thought I would be safe.
I gave in and told him that I was staying at the Marriott in room 332. Jonathan didn't live very far away from the hotel. He showed up in 20 minutes. I was actually kind of shocked. I didn't think he would actually show up. After the knock at the door, my heart sank. I debated with myself on whether or not I should pretend I wasn't even in the room. I also didn't want to be rude. I did in fact invite him over after all. I finally said to myself "fuck it" and I opened the door.
Jonathan was very much as he described himself to be. Little bit taller than I was at 6'2", about 210 pounds. Little streaks of gray in his goatee and in his hair. We shook hands and he entered my room. After some small talk, we started to watch some porn together. It was lesbian porn… My favorite. We started talking about sex, about what his first time was like. The emotions he felt, the sensations he encountered. Jonathan described everything about what it felt like to have someone's dick in his mouth. He even described what it tasted like.
By this time I was pretty revved up. He took things so slow with me. He asked me if I was ever going to surrender to my desires and finally go through with it. I was still unsure. What would that make me if I did that? Would I be gay? It sounds like a very silly question but at the time it was central to how I self identified. I didn't want how I identified myself to change and yet it felt like it was about to.
He kept saying "at some point you're simply going to have to just try it." He was right, but I still needed more convincing.
He asked me if it was okay if he touched himself. I was a little caught off guard. Considering the situation I placed myself in, I don't know why I was surprised. But I was. Was this really happening? Did I have the guts to go through with it?
Jonathan sat in the chair across the room and pulled his pants down. He was much larger than I thought he would be. He actually looked huge and he wasn't even close to being hard. I just sat there like an idiot watching him. It was like he was putting on his own little personal show just for me. The more he touched himself, the larger he became. He asked me if I liked what I saw. I told him that he was pretty impressive. Then he asked me if I wanted to touch it. I did. But rather than give in, I told him that I wasn't ready for that.
That is where things took a slightly different turn. I half expected him to leave at that point. But he didn't. He didn't get angry or seem even a little frustrated. He simply smiled and said "that's okay, you need to do what feels comfortable for you". As I sat there and watched him, I started to get hard. I started adjusting myself a little. He was perceptive and picked up on that. "It's okay if you touch yourself too" Jonathan said. "You know you want to". He was right, I did want to. "I promise not to tell anyone" Jonathan assured me. I rolled my eyes and smiled. "Relax. We're not doing anything wrong". He was so reassuring. I was so horny and I finally gave in, stood up and slipped my pants down while sitting on the bed.
Jonathan continued his seduction, "you see? That wasn't so hard was it?". I am much smaller than Jonathan . At best I am 6 inches long when fully hard. He was solid 8 inches. "You have a really nice looking cock". That caught me off guard. I simply mumbled "thanks".
Jonathan got up from the chair and slid completely out of his pants. Then he sat on the bed next to me while still stroking his hard dick. "It's okay" he said. "You see? It's not that bad." I had been close to giving into my desires in the past but I never put myself in a position where I was sitting on a bed next to a guy who I just met, both with our cocks exposed and jerking off. This was starting to get out of control. He was taking these baby steps with me. Not being overly aggressive, but advancing slowly, deliberately all the while assuring me that we would only go as far as I wanted and I'll farther.
It started to become clear that one of us was in control and it wasn't me.
"Can I touch it?" Jonathan's words went right through me. "I don't think I'm ready" I replied. "I promise to touch it really quick. I just want to feel it a little". Then Jonathan reached over. I didn't try to stop him by pushing his arm away. He put his hand over the top of my hand while I was touching myself. I moved my hand away and he gripped me around my shaft.
He put his hand over the top of my hand while I was touching myself. I moved my hand away. This was the first time I was EVER touched by another man. And Jonathan lied. He didn't touch it just quickly. He held on and stroked me and it felt amazing. He sat there for about a solid minute or so slowly stroking me. I thought I was going to cum right there. Every time he sensed that I was close he pulled back and let me recover.
Jonathan knew that he had me. There was no turning back now. He asked me if I wanted to touch him. I did. I reached over and grabbed his dick. I started fondling his balls and stroking him. It was so strange. Jonathan was rock hard and yet soft at the same time.
We sat there for a few minutes jerking each other off. "Do you like it?" He asked me. I don't think I actually responded I simply nodded yes. Jonathan asked me if he could kiss my dick. I think his actual words were, "can I kiss it?" I meekly said "yes ". He took his hands off of me and repositioned himself. He leaned over and kissed the tip of my cock. He didn't stop there however. He allowed it to go into his mouth, inch by inch. And he started sucking on it. Bobbing his head over and over. Just like when he was jerking me off, when he sensed I was close he stopped. This guy really knew what he was doing.
Jonathan asked me at that point, "do you want to kiss mine?" The part of me that did not want to surrender told him no. I said "I'm just not ready to do that". Jonathan then put the full court press on me. "You were jerking me off, and you let me go down and blow you. You have come this far. Just come a little farther. No one's going to know. It'll be our secret." Jonathan stared directly into my eyes for what felt like forever. "We're just two boys exploring", He smiled again reassuring me that if I said no it would be okay. Except I said "ok".
"I've never done this before. I'm not sure I know what I'm doing". Jonathan suggested that I get on my knees off of the bed. I did so. He sat on the edge of the bed with his legs spread. His dick was only 10 inches from my face. I could smell his musty scent. It was intoxicating. "You're going to do fine" he said. "Just do what feels natural".
I came in a little closer and placed my hands and arms over the top of his legs touching the side of his hips. I moved in closer. I was only a couple of inches from the tip. I moved in closer and grabbed it with my right hand. My lips were only two inches from his dick. His scent was penetrating my nostrils. My heart was pounding. I moved in just a little closer and allowed his dick to brush the side of my cheek. I kissed the base of his cock. And then begin to slowly kiss the underside of the shaft.
For all of my initial hesitation and worry about this very act happening and what it would mean, I couldn't get out of the situation if I wanted to and getting out of it was the last thing I wanted. I opened my mouth and let my tongue touch the base of his shaft. I continue to work my way, inch by glorious inch to the head of his dick. It was so wide I wasn't sure I could fit it in my mouth but I open wide and took him in. I sucked on him slowly.
I continued to bob my head up and down his dick. He told me to look at him, and I looked up and made eye contact with him while I was sucking him off. It was truly an a moment I will never forget. It was a moment I never wanted to end.
I sucked him off for about five minutes and then he asked me if I wanted him to shoot it down my throat. As drunk as I was off of this experience, I wasn't ready for that and he blew it all over my neck and chest instead. I thought I was going to explode. One drop of cum landed on my upper lip. I licked it and tasted him. Now it was my turn.
Jonathan switch places with me. He laid me back on the bed. And he took me in his mouth and started sucking very deep. His fingers made their way to my ass. And while he was blowing me, he was fingering me with two fingers. I didn't have any resistance anymore. Feeling between having my dick in the mouth of another guy, while he was fingering me sent me over the edge. I told him that I was about to cum. He didn't slow down at all and I started to lose control, convulsing into his mouth. After I was done we both got cleaned up. Still naked, he grabbed me by the deck pulled me close and kissed me on the mouth. He told me next time, we were going to take it to the next level. "My fingers were just the start". I couldn't until wait till next time.
To be continued…
I was traveling for work. Being alone in a hotel room gives a married guy too much temptation. I jumped on Squirt and surfed around looking for some attention. That's when Jonathan instant messaged me. Jonathan was older than I was. He was in his mid 50s while I was 46. We chatted for nearly an hour. I was getting really horny as I asked him what his first experience with another guy was like. Finally, he told me that he would give me as much detail as I wanted in person if I only gave him my room number.
This was a huge step for me. I wasn't sure I could actually go through with it. But I convinced myself that if he came over to my hotel room, we would only talk about his experiences. I knew it would likely lead to something more but I thought 'more' meant that we would simply jerk off in front of one another. I had jerked off in front of other guys a few times before and it never graduated to touching or anything else. So I thought I would be safe.
I gave in and told him that I was staying at the Marriott in room 332. Jonathan didn't live very far away from the hotel. He showed up in 20 minutes. I was actually kind of shocked. I didn't think he would actually show up. After the knock at the door, my heart sank. I debated with myself on whether or not I should pretend I wasn't even in the room. I also didn't want to be rude. I did in fact invite him over after all. I finally said to myself "fuck it" and I opened the door.
Jonathan was very much as he described himself to be. Little bit taller than I was at 6'2", about 210 pounds. Little streaks of gray in his goatee and in his hair. We shook hands and he entered my room. After some small talk, we started to watch some porn together. It was lesbian porn… My favorite. We started talking about sex, about what his first time was like. The emotions he felt, the sensations he encountered. Jonathan described everything about what it felt like to have someone's dick in his mouth. He even described what it tasted like.
By this time I was pretty revved up. He took things so slow with me. He asked me if I was ever going to surrender to my desires and finally go through with it. I was still unsure. What would that make me if I did that? Would I be gay? It sounds like a very silly question but at the time it was central to how I self identified. I didn't want how I identified myself to change and yet it felt like it was about to.
He kept saying "at some point you're simply going to have to just try it." He was right, but I still needed more convincing.
He asked me if it was okay if he touched himself. I was a little caught off guard. Considering the situation I placed myself in, I don't know why I was surprised. But I was. Was this really happening? Did I have the guts to go through with it?
Jonathan sat in the chair across the room and pulled his pants down. He was much larger than I thought he would be. He actually looked huge and he wasn't even close to being hard. I just sat there like an idiot watching him. It was like he was putting on his own little personal show just for me. The more he touched himself, the larger he became. He asked me if I liked what I saw. I told him that he was pretty impressive. Then he asked me if I wanted to touch it. I did. But rather than give in, I told him that I wasn't ready for that.
That is where things took a slightly different turn. I half expected him to leave at that point. But he didn't. He didn't get angry or seem even a little frustrated. He simply smiled and said "that's okay, you need to do what feels comfortable for you". As I sat there and watched him, I started to get hard. I started adjusting myself a little. He was perceptive and picked up on that. "It's okay if you touch yourself too" Jonathan said. "You know you want to". He was right, I did want to. "I promise not to tell anyone" Jonathan assured me. I rolled my eyes and smiled. "Relax. We're not doing anything wrong". He was so reassuring. I was so horny and I finally gave in, stood up and slipped my pants down while sitting on the bed.
Jonathan continued his seduction, "you see? That wasn't so hard was it?". I am much smaller than Jonathan . At best I am 6 inches long when fully hard. He was solid 8 inches. "You have a really nice looking cock". That caught me off guard. I simply mumbled "thanks".
Jonathan got up from the chair and slid completely out of his pants. Then he sat on the bed next to me while still stroking his hard dick. "It's okay" he said. "You see? It's not that bad." I had been close to giving into my desires in the past but I never put myself in a position where I was sitting on a bed next to a guy who I just met, both with our cocks exposed and jerking off. This was starting to get out of control. He was taking these baby steps with me. Not being overly aggressive, but advancing slowly, deliberately all the while assuring me that we would only go as far as I wanted and I'll farther.
It started to become clear that one of us was in control and it wasn't me.
"Can I touch it?" Jonathan's words went right through me. "I don't think I'm ready" I replied. "I promise to touch it really quick. I just want to feel it a little". Then Jonathan reached over. I didn't try to stop him by pushing his arm away. He put his hand over the top of my hand while I was touching myself. I moved my hand away and he gripped me around my shaft.
He put his hand over the top of my hand while I was touching myself. I moved my hand away. This was the first time I was EVER touched by another man. And Jonathan lied. He didn't touch it just quickly. He held on and stroked me and it felt amazing. He sat there for about a solid minute or so slowly stroking me. I thought I was going to cum right there. Every time he sensed that I was close he pulled back and let me recover.
Jonathan knew that he had me. There was no turning back now. He asked me if I wanted to touch him. I did. I reached over and grabbed his dick. I started fondling his balls and stroking him. It was so strange. Jonathan was rock hard and yet soft at the same time.
We sat there for a few minutes jerking each other off. "Do you like it?" He asked me. I don't think I actually responded I simply nodded yes. Jonathan asked me if he could kiss my dick. I think his actual words were, "can I kiss it?" I meekly said "yes ". He took his hands off of me and repositioned himself. He leaned over and kissed the tip of my cock. He didn't stop there however. He allowed it to go into his mouth, inch by inch. And he started sucking on it. Bobbing his head over and over. Just like when he was jerking me off, when he sensed I was close he stopped. This guy really knew what he was doing.
Jonathan asked me at that point, "do you want to kiss mine?" The part of me that did not want to surrender told him no. I said "I'm just not ready to do that". Jonathan then put the full court press on me. "You were jerking me off, and you let me go down and blow you. You have come this far. Just come a little farther. No one's going to know. It'll be our secret." Jonathan stared directly into my eyes for what felt like forever. "We're just two boys exploring", He smiled again reassuring me that if I said no it would be okay. Except I said "ok".
"I've never done this before. I'm not sure I know what I'm doing". Jonathan suggested that I get on my knees off of the bed. I did so. He sat on the edge of the bed with his legs spread. His dick was only 10 inches from my face. I could smell his musty scent. It was intoxicating. "You're going to do fine" he said. "Just do what feels natural".
I came in a little closer and placed my hands and arms over the top of his legs touching the side of his hips. I moved in closer. I was only a couple of inches from the tip. I moved in closer and grabbed it with my right hand. My lips were only two inches from his dick. His scent was penetrating my nostrils. My heart was pounding. I moved in just a little closer and allowed his dick to brush the side of my cheek. I kissed the base of his cock. And then begin to slowly kiss the underside of the shaft.
For all of my initial hesitation and worry about this very act happening and what it would mean, I couldn't get out of the situation if I wanted to and getting out of it was the last thing I wanted. I opened my mouth and let my tongue touch the base of his shaft. I continue to work my way, inch by glorious inch to the head of his dick. It was so wide I wasn't sure I could fit it in my mouth but I open wide and took him in. I sucked on him slowly.
I continued to bob my head up and down his dick. He told me to look at him, and I looked up and made eye contact with him while I was sucking him off. It was truly an a moment I will never forget. It was a moment I never wanted to end.
I sucked him off for about five minutes and then he asked me if I wanted him to shoot it down my throat. As drunk as I was off of this experience, I wasn't ready for that and he blew it all over my neck and chest instead. I thought I was going to explode. One drop of cum landed on my upper lip. I licked it and tasted him. Now it was my turn.
Jonathan switch places with me. He laid me back on the bed. And he took me in his mouth and started sucking very deep. His fingers made their way to my ass. And while he was blowing me, he was fingering me with two fingers. I didn't have any resistance anymore. Feeling between having my dick in the mouth of another guy, while he was fingering me sent me over the edge. I told him that I was about to cum. He didn't slow down at all and I started to lose control, convulsing into his mouth. After I was done we both got cleaned up. Still naked, he grabbed me by the deck pulled me close and kissed me on the mouth. He told me next time, we were going to take it to the next level. "My fingers were just the start". I couldn't until wait till next time.
To be continued…
Alma
- 19.04.2020
- 22
- 0
