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Gay Stories
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Gay Male / 51
The One Night Stand In NY City
The Seduction. I was out of town on a business trip meeting with lawyers due to a tax complication. The lawyer assigned to me was a sixty year old guy, with lots of experience. I was at that time a 40 year old tax lawyer with limited experience, primarily to the company I worked for. We met in his office and the more we talked the deeper it got. Surely we couldn't be in that deep? But he went on, a lot of it was that the sales group had set up the transaction, without getting legal opinion.
When it go late, granted I had arrived around four that afternoon, he suggested we get some Italian. We walked to a restaurant a few blocks from the office. I swear the owner was gay, and the help was gay. No girls, nothing but gay boys working the floor. Tight pants and tight shirts and 'oh honey' and 'dear' and 'my what big hands you have'. But my host took it all in stride convincing me that we were there for the food, not the floor show. But the boys kept coming on, and here and there my host would 'swat' a rump and get a 'now dear, no touchy touchy, just for looking'.
When the tip time came he told the waiter, no kiss no tip. And he wanted a big boy kiss for the tip. It was a kiss, on the lips. We left the restaurant and he suggested a drink and a floor show and we went into a gay bar. Men dancing, men kissing, men in short shorts, men in tank tops. These were the boys and the men? Well they were in suits and had their arm around the shoulder of another suit. As my eyes got accustomed, the men dancing were dancing cheek to cheek, some outright kissing. In the booths there was handholding and hands up high on thighs. We sat down at a booth, a small booth, too small to really allow you to get comfortable. We ordered from the one of the boys in a tank top, 'hi Frank, who's the boyfriend'. He answered that I was 'Tom from Dallas and I was visiting so he was taking me around and showing me a good time'.
Frank asked me to get comfortable, and if i wanted to dance we could have a go at it. Frank ordered, he never asked what I wanted. Frank got hot from the liquor and said he wanted to dance, and he stood up and grabbed my hand and I had to follow. Frank is a big man, not heavy, just big and his arm around my neck sucked me in. He kissed my neck before kissing me on the lips. 'When I was your age we couldn't do this'.
He said that he had locked the office so we could just go back in the morning. He wanted to get some fresh air and work off the buzz from the liquor. We walked again to a building and he let himself in with a code at the door. In his apartment he took off his coat and offered to take mine for me. There he kissed me, this time a long wet kiss and he told me he was looking forward to getting to know me. Down to his boxers, he had a hairy back and legs and a big enough beer belly. He got me down to my boxers and he peeked into the fly to see what I was licensed to carry.
On the bed, he now had me where he wanted me, the kissing and caressing behind us, he was working his action. I could see his big ass in the mirror on the wall, which I guessed was put there on purpose. His ass tightened and released as he drove his point home. My hands on his arms, I felt him jerk and he said it was coming. He finished and fell off, his wet dick half full, looked menacing.
The next day was all business, suits and a formal lunch with another partner. He was experienced, not only in tax matters, and he did resolve a strategy. No matter that in the end the mistakes made by the sales team was going to cost money, at least we had identified the problem and we would avoid penalties and interest later. The fees, they were pretty big, considering the number of hours, and New York rates aren't cheap.
I sit here and think about Frank, that was before Covid, over ten years ago. I'm fifty now, and that one night stand is one of my finest memories.
When it go late, granted I had arrived around four that afternoon, he suggested we get some Italian. We walked to a restaurant a few blocks from the office. I swear the owner was gay, and the help was gay. No girls, nothing but gay boys working the floor. Tight pants and tight shirts and 'oh honey' and 'dear' and 'my what big hands you have'. But my host took it all in stride convincing me that we were there for the food, not the floor show. But the boys kept coming on, and here and there my host would 'swat' a rump and get a 'now dear, no touchy touchy, just for looking'.
When the tip time came he told the waiter, no kiss no tip. And he wanted a big boy kiss for the tip. It was a kiss, on the lips. We left the restaurant and he suggested a drink and a floor show and we went into a gay bar. Men dancing, men kissing, men in short shorts, men in tank tops. These were the boys and the men? Well they were in suits and had their arm around the shoulder of another suit. As my eyes got accustomed, the men dancing were dancing cheek to cheek, some outright kissing. In the booths there was handholding and hands up high on thighs. We sat down at a booth, a small booth, too small to really allow you to get comfortable. We ordered from the one of the boys in a tank top, 'hi Frank, who's the boyfriend'. He answered that I was 'Tom from Dallas and I was visiting so he was taking me around and showing me a good time'.
Frank asked me to get comfortable, and if i wanted to dance we could have a go at it. Frank ordered, he never asked what I wanted. Frank got hot from the liquor and said he wanted to dance, and he stood up and grabbed my hand and I had to follow. Frank is a big man, not heavy, just big and his arm around my neck sucked me in. He kissed my neck before kissing me on the lips. 'When I was your age we couldn't do this'.
He said that he had locked the office so we could just go back in the morning. He wanted to get some fresh air and work off the buzz from the liquor. We walked again to a building and he let himself in with a code at the door. In his apartment he took off his coat and offered to take mine for me. There he kissed me, this time a long wet kiss and he told me he was looking forward to getting to know me. Down to his boxers, he had a hairy back and legs and a big enough beer belly. He got me down to my boxers and he peeked into the fly to see what I was licensed to carry.
On the bed, he now had me where he wanted me, the kissing and caressing behind us, he was working his action. I could see his big ass in the mirror on the wall, which I guessed was put there on purpose. His ass tightened and released as he drove his point home. My hands on his arms, I felt him jerk and he said it was coming. He finished and fell off, his wet dick half full, looked menacing.
The next day was all business, suits and a formal lunch with another partner. He was experienced, not only in tax matters, and he did resolve a strategy. No matter that in the end the mistakes made by the sales team was going to cost money, at least we had identified the problem and we would avoid penalties and interest later. The fees, they were pretty big, considering the number of hours, and New York rates aren't cheap.
I sit here and think about Frank, that was before Covid, over ten years ago. I'm fifty now, and that one night stand is one of my finest memories.
