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I used to work as a financial planner and early in my career I had to cold call for appointments. It was hell but it worked. One method I used was called a ‘meet and greet.’ I’d call a couple hundred people from the phone book and ask them if I could send them a brochure. If they said yes, I’d send them one and follow up with a phone call and see if I could come by to discuss my services and hopefully convince them to come to my office for an appointment. That’s how I met Jim. He was my first.
I was about 30 at the time I met Jim and while I’d gone through several bouts of gay sex fantasies I was married and had never acted out on them. I’d never even really had the opportunity. I’d found a couple of guys attractive over the years but was too scared to do anything and honestly was mostly attracted to women.
I arrived at Jim’s house for the ‘meet and greet’ and he met me at the door. He was about 5’11“ and had short dark hair and a short beard. He was athletic looking and attractive but I wasn’t really thinking about him ‘that’ way. We sat in his living room and made some small talk and then began talking about my services. Things were going well and he looked like a good candidate for my work eventually but he wasn’t quite ready I decided. I wasn’t in a hurry to get back to the office so we just kept talking for a while and he got us some iced tea. While he was in the kitchen I was glancing around the living room and noticed a stack of gay porn by the large screen TV. I was curious and wanted to go through the stack but didn’t want him to catch me and have both of us embarrassed. We chatted for a while more but time was pressuring me and I made my exit.
I went back to the office but couldn’t get the porn stack of my mind. In my line of work I couldn’t exactly walk into the one porn shop in town and buy gay porn without someone finding out. This was also before high-speed internet access so downloading wasn’t quick or easy. Jim had made me feel so comfortable I decided to call him and ask if I could borrow some. I figured if he let a total stranger walk into his house and see it, he would be that embarrassed if I asked. So I did. I told him I was curious and asked if he’d let me borrow one. So he did. He said he’d pick one out that had some variety in it. I stopped by and was a little embarrassed again but again he made me feel comfortable and told me to keep it as long as I wanted.
Needless to say I spent quite a few hours with that tape. Some of it I liked, some I didn’t. There was one scene I really enjoyed with this big blond guy really giving another guy a going over but it wasn’t the rude degrading kind. It was obviously pleasurable for both. That I liked. So much porn these days is about degrading one of the players. Anyway, after about a week I called Jim and told him I wanted to bring it back and found a time that he’d be home.
I stopped by about 2pm on a Saturday and was really hoping he’d let me borrow another tape as I had the afternoon free. He welcomed me in and I stammered through a few stupid sentences, hoping he had another one picked out to give me. He offered me a seat and a beer at the same time and I accepted both because I needed the beer to calm me down and a seat because I felt queasy weird. Anyway, he gave me the beer and we started chatting about work and other inane stuff. After a while he asked me how I liked the tape and I told him what I thought. He told me he had another tape with the same blond guy in it. He got up and I thought he was going to get it for me but instead he put it in the VCR after he picked it up. He fast-forwarded to the scene and after a few minutes I was watching gay porn with a guy I just met. A little weird for me to say the least. I had a queasy feeling in my stomach but I wasn’t freaked out. It was kind of like watching any other porn with people you’re not intimate with. You watch but try to pretend it’s nothing and pray you don’t get a hard on. Needless to say, I drained the beer quickly and was offered another.
While we were watching he asked me about my experience and I told him that I had none. I opened up some and told him I’d fantasized about it over the years but never had any chances to try it. I was too chicken to try any of the riskier places like video arcades and the like so just never had a chance. We talked about what we were into and what we weren’t. We were pretty compatible actually. He was a top and I thought I was a bottom; I was only turned on by the vanilla type stuff on the tapes. I was getting a slight buzz and starting to feel my groin stirring as I watched the porn and talked about gay sex with a man. When we were through our second beer Jim got up to get another and I noticed that he had a substantial bulge in his shorts. This caught me off guard as I had only been thinking about getting another tape but realized he might be interested in me. I got hard instantly. I wasn’t expecting that either.
He came back in the room with the beers but I was just staring at his groin. He wasn’t trying to hide anything. As he came closer with my beer I surprised myself and reached out and put my hand on his thigh. He didn’t pull away but moved closer and handed me the beer. I took it in my free hand and slid my hand up his outer thigh and pulled him closer. He was standing directly in front of me while I sat on the edge of the couch. I looked up at him and he smiled down at me. That was all I needed.
I slid my hand up inside the leg of his shorts and brushed it across the front of his boxers. His cock jerked as I brushed the head. As I rubbed up and down his cock I was just dumbfounded. I had never touched a guy like this before and I just ached for more.
I put down the beer and pulled my hand out of his shorts. I opened the button at the top, pulled the zipper down and his shorts just fell to the floor. His cocked pressed at the fabric of his boxers but didn’t come through the hole. I reached out and rubbed it through the fabric. I could feel the heat of it through the fabric. All I could think was that I wanted to see it, so I reached through the hole with my fingers and pulled it through. There it was pointing straight up in front of me. It was bigger than mine with a large head and thick shaft and it was amazing. I looked at it for a while then I looked up at Jim. He just watched me with a smile on his face. As I stared at it, I ran a hand around and touched his ass, just caresses. I also slipped my hand up under his shirt across his muscled chest brushing the nipples with my palms. His cock was just inches from my face and I knew that I was going to get my first taste of one. I grabbed the shaft and slowly started to jerk him off. Very slow, up and down. It was magical to me. I couldn’t believe I was doing it. I had fantasized about something like this so many times.
I pulled it down towards me and slowly slipped the head through my lips. Jim groaned at that and I swear I could’ve cum right then. Here was an attractive guy groaning at what I was doing to him. I moved my tongue around the head and began sucking him. I used every trick I had had done to me or seen. I fondled his balls, jerked him while I was going down on him, tongue bathed …
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