So sorry for the delay in posting the events of this past weekend. I had a business trip out of town and this is the first time I have had to record the events of the weekend.
We got into town late Friday evening and checked in to the hotel. Then headed out to dinner since we were both starving. Great meal and conversation, and at one point during the meal he mentioned about how cute the waitress was and wondered aloud if she would be interested in DP. (We both have a fantasy about DP and want to experience it together). We head back to the hotel. I make drinks and we make our way out to the balcony. After several drinks, I hooked up the DVD player and laid out all of the porn I brought and told him, "you choose this time". He studied all the covers and settled on a DVD that featured a scene with two girls, one a red-head (he loves reds) and one guy. He said "before we watch, lets smoke that blunt". Out on the balcony, enjoying the cool night air and smoking, he said "How did you learn to beat off?". I told him I just kind of discovered it in the shower one day, which is true. He offered, without me asking him, that he was 11 and a kid he knew in his neighborhood who was 13, had showed him how. He said he remembered the guy being able to beat off and cum within several minutes. He, however, could beat and beat until his dick was bright red with no results. He said eventually he got it, but it took a while.
Back in the room after smoking, I popped in the DVD and cued up the scene he wanted. I then stripped completely and he went to the bathroom to grab some toilet paper. In the times we have beaten off together, I always just blow all over my stomach. He beats with his right hand and holds the paper in his left. Just when he's about to blow, he covers the head of his dick with the paper and catches all his cum. He also doesn't make a sound. He flinches just a little as he's cumming, but doesn't make any noise. I'm kinda vocal!
We're a good ways into the scene and I'm feeling good and can tell he is really into the scene as well. I say "Don't you want to switch hands". He looked at me confused and said "What do you mean?". I said "I'll beat you and you can beat me". He said "Nah, I'm good". I said "Are you sure?". And he repeated "I'm good". I said "Have you ever tried it?" and he repeated "I'm good. I don't want to do that". First I was crushed and hugely disappointed, but then I quickly remembered that the first time I ever beat off in front of him, I asked him if he wanted to join me and he said "I'm good". The next time we were together, he asked me to get him paper and he whipped it out. So, I'm anxious to see if the next time we get together, if he will ask to switch.
We clean up and have a few more drinks and then off to bed. The next morning he's up first and wakes me up moving around the room. We slept in a king sized bed and during the night I remembered waking up to his leg brushing against mine. We're laying in bed, both of us on our phones checking messages and playing games and he mentions that he's gonna have to get a shower soon so we can head out to catch our tee time. I said "I'm gonna rub one out before I shower." He heads into the bathroom to take a dump and I pop in a DVD. I picked the one that we had been watching and picked up on the scene where we had left off.
He's in there a long time, so I figure he's jacking off in private this time. I'm edging watching the porn. After probably 15-20 minutes he comes out and I'm rock hard, laid out on the bed, and milking my dick with a left handed reverse stroke. He stands at the end of the bed watching the scene (the TV is to the right of the bed if you are laying on it) and I can tell he's getting hard because his shorts are starting to tent in the front. After several minutes of watching the scene, he heads back into the bathroom, I assume to beat off in private, but returns with paper and heads to the couch. He whips his hard dick out and starts beating in rhythm to the scene. This is the first time he has ever beaten off with me, completely sober and not high. I purposely do not instigate anything or offer to help. I feel at this point I am going to have to let him make the next move. We are both getting close and I move into a position where I am on my knees, kneeling in bed and now beating with my right hand. Just as I can tell he's cumming, I rapidly pick up my stroke and blow all over the towel I have laid out on the bed. He comments "That was a good one. Wish she was here so I could bang her instead of my hand". I agree and tell him I'm going to head off to the shower, so we can get going.
We have a good round of golf and a long ride back home. We, of course, talk every day this past week and talk about what a good trip it was and he said he hopes we can go again soon. Just yesterday, he calls me to mention that his wife is going out of town for an overnight trip, and that we can get in a round on Thursday afternoon and then hang out that night. That implies that he wants me to spend the night, and bring the porn!
At this point, I so want us to engage in some sort of sexual activity together, but don't want to cross a boundary that cannot be undone if it's not welcome. I feel that this is progressing and he eventually will want to do something together, but I think we're both at the point where neither wants to make that bold move that initiates the encounter. I know and trust that he has and will keep everything we do together in the utmost confidence. I'll just have to wait and see if he wants to "swap hands" in our next encounter. Hopefully he will and more.
