I've always had a high sex drive and a need to cum multiple times a day, so even on days I had sex, I'd often still masterbate. To help with my sex drive, I took to chat rooms. Getting in a good conversation would keep me sexually stimulated and I jerked off all the time during chats so this became my release for the next few years. Most of the people in the chat rooms are men and I soon realized I didn't like talking to men my age or younger (I was 30). Those guys just wanted a quick chat to get them off and then they were gone. However, I found that with older retired men the conversations were much longer, which provided me a lot of personal foreplay before I came.
One of those guys was Bill, he was a 58 year old local man who had been divorced for 5 years. He and his wife had been swingers and during our chats he would tell me about those experiences. After several months of chatting Bill invited me to his place to watch porn. He said that he lived alone so his place was very private and he told me how much more intense it would be having these discussions in person while we watched porn and jerked off. I wasn't ready for that but I told him I'd think about it. Each time we chatted he'd politely bring it up and tell me it'd be cool and we could just hang out over a few drinks. He'd even have the TV already on to avoid any awkward silence when I got there. He also said that I could leave at any point that I felt uncomfortable and he would understand. I could tell from chatting with him that he was a respectful and educated man and he even sent me his picture so I could see he was a normal guy. He was clean cut and had no facial hair and I thought he looked like the type of guy that wore a suite to work.
I finally worked up the courage and agreed to come over when my girlfriend was out of town for a few weeks on a work assignment. As I drove up to Bill's house I was very impressed. He lived in a nice large house in a nice upscale neighborhood. I rang the doorbell and he answered with my drink already in his hand.
"Great to meet you" Bill said as he shook my hand and handed me a glass of whiskey "come in and have a seat."
I followed him as he turned and walked towards a media room. When he opened the doors to the media room I saw some softcore porn playing on a huge TV. He told me to take a seat in one of the chairs and he sat in another several feet away. Bill's chair was a recliner and mine was just a regular chair with armrests. We exchanged small talk for a while and I felt a bit strange being the house of someone I'd never met watching porn. I'm not a whisky drinker, I was actually expecting beer when he mentioned drinks, but due to my nervousness I finished my drink within 5 minutes. As I finished it he said he was glad to see I was whisky drinker and he grabbed my glass and came back with another that was filled twice as full as the first. I was beginning to relax as each minute passed so my second drink lasted longer than the first but I still finished it relatively fast as I was still a bit nervous. He grabbed my glass again to refill it but this time chuckled and said "It helps nerves, but you don't need to be nervous around me" and with that he went off to the kitchen to refill it.
Being alone in the room made me more relaxed so I began rubbing myself through my jeans. I didn't hear him when he come back with my drink but when he set the glass down on the table he said "that's more like it, feel free to take it out and play with it, that's what I'm going to do."
When he got to his chair he unzipped and stepped out of his pants and then sat down, reclined the chair, and began playing with himself. Our chairs were several feet apart but angled towards the TV so I had a view of his cock and even though I wasn't trying to look, I couldn't help notice that his dick was much bigger than mine. He wasn't looking at me but he was saying how hot it is watching porn with a buddy. The movie was hot and I wanted to take out my cock and stroke myself but I was still too embarrassed and couldn't work up the courage to do it. After a while he looked over and said "It's just you and me, you'll feel better if you take it out." That was all the prompting I needed and I unzipped and started playing with myself to which he added "Good boy, that's more like it."
I'm not sure if it was the buzz from the drinks, the porn, or both but stroking myself in the same room with another man was the most taboo thing I'd ever done and I was rock hard. I'd just finished my third drink and was getting to the point where I wanted to cum, when I realized we hadn't discussed that. There were no towels or tissues and I didn't even know where the bathroom was. He must have noticed my dilemma because he spoke up and said "If you're done, the bathroom's the first door on the right but if you hold out, it'll be much better."
I wasn't sure what he meant so I asked him to explain. He grabbed the remote and started a different movie and said he'd tell me after he refilled our drinks. He then got up, grabbed both glasses, and headed back to the kitchen to refill our drinks again.
The new video that started playing was of an attractive couple in their late 30's with a younger guy in his early 20's. It was much more erotic than what we'd been watching so I slid my pants down to my knees making it easier for me to stroke myself. Bill came back with my drink but I was so caught up in the moment that I didn't even stop touching myself. I'm not sure if it was intentional or not but as he set my glass down, he was much closer to me than before and his naked cock was sticking straight up just a few feet from me. When he sat down he showed me a $100 bill and said "Here's what I mean, if you can go the next 15 minutes without touching yourself it's yours."
I was really ready to cum but I'm also a fairly competitive person and this seemed like an easy hundred so I said "If you're serious you're on."
"I'm very serious, your clock just started" he replied.
Not being able to touch myself was bad enough but Bill was making it worse. He was sitting in his chair stroking himself and being very vocal about how good his big dick felt. In the video, the younger man was on his back and the woman was straddling his face. She motioned to her husband and pointed at the young mans cock and he grabbed hold of it and began stroking it. Bill looked at me and asked me if I'd ever been touched by a man and when I said no he said "we can change that."