Just got back from the trip. We had a great time but not the great time I was hoping for.
On Friday night we got there really late, about 2am. Got settled in and started drinking. Drank for a couple of hours all the time talking about our favorite subject, sex! Then we did a shot of Jaeger. That sent him over the edge. He passed out. So no contact the first night.
Played golf all day Saturday, then back to the room to shower. After cleaning up, we headed out to dinner and then to a bar across from the hotel. Tried to hook up with several chicks but no luck. Our intention was to bring them back so we could try double penetration. On Friday night before he passed out, he said he had always wanted to try DP and I said I had as well. I asked him if he would have any problem doing DP where we were both in the pussy with our dicks rubbing against each other. He said "No, that wouldn't bother me" Well, no luck. Several scenarios where one chick would seem interested but her friend would talk her out of it.
After the bar shut down, we headed back to the room. As we were walking and rehashing the night, I said "Guess we'll just have to go back and rub one out to porn" and he said "Guess so, and then order pizza!". I said "Deal".
Once in the room we find an all night pizza place in the phone book that delivers. While he places the order I put in the porn DVD. I had brought some from home. Just so happens that I had a DVD that had DP in it. I asked if he wanted to see that scene and he agreed. We are both sitting on the couch next to each other, he still fully dressed and me down to my boxer briefs. I'm already bulging but purposely do not touch. I'm waiting to see what he'll do first. I notice that he starts rubbing himself through his jeans. This goes of for several minutes when he asks me if I'm going to go get a towel or tissue. I said "Sure, I'll get it." When I get back his pants and underwear are down to his knees and he has raised his shirt to expose his chest. I immediately notice his erect dick! It's much larger than I expected. At this point I had only seen him flaccid and he was on the small side. I immediately commented "Wow man, look at that dick. You're a grower not a shower" as I sat down on the couch and reached over and gave it a quick tug. He said, "Yeah, but I'm still not as big as you". To be honest it looked like we were the same girth, but I am a little longer. He had a nice shaped head that at this point was fully engorged. His erect dick stood up on it's own at about 10 o'clock, with no curve. I have a strong curve that stands completely up at 12 o'clock.
We continued to watch the porn and I dropped my boxer briefs completely and sat as close to him as I could on the couch, putting my feet up on the coffee table so I could spread my knees far apart and rest one on his leg. I'm dripping precum but have also brought back a bottle of lube. I ask him if he wants any lube and he declines, saying he prefers the friction.
I try to jack slowly so I can see how this will play out. My intention was to wait until he was almost ready to blow and ask if we could swap hands and rub each other. Just a gut feeling that I had that I wasn't going to be able to ask if I could blow him so I just put it out of my mind. The scene is getting very hot and he starts to moan a little. Just as I am about to suggest swapping, he blows his load. I quickly jerk on my dick to catch up and blow my load about a minute later. We both clean up and head into the bathroom to piss. As we both stand over the toilet, I comment again on his size. "I'm shocked your dick is so big, I never had any idea". He said "It gets the job done".
About this time the pizza guys knocks on the door and we scarf down the food quickly. It's about 3 am now and we go to bed.
The next morning I'm up first. I hang out in the room quietly as he sleeps and wait for him to wake up. After he gets up, we start talking about what we'll do for lunch before we go play. I start up the porn again and say I'm going to rub one out before I shower. I strip completely down and sit on the couch. He say's he's going to shower. He goes towards the bathroom and comes back after he started the water standing in his underwear right in front of the TV. His underwear is below his ass cheeks and halfway down his crotch. The man really does have a perfect bubble ass. I notice that as he stands in front of the TV his crotch is growing. His underwear is sticking straight out. He puts his hand inside his underwear and I'm excited thinking I am going to see a repeat performance. But no...he turns and head to the shower, I assume to jack off in private this time. I finish up and head to the bathroom as he is coming out of the shower. I try not to miss any opportunity to see him when he's naked. Wish I could have gotten a picture of him for my spank bank and to post here but not an option.
That's all I have to report this time. We won't have another chance to take a golf trip alone probably until the fall and worst case scenario until next spring. There might be some occasions when he'll come over to my house late after he gets off work and before he goes home, so we can hit the pipe. On some of those occasions I have had porn on when he got to my house but he never joined. Since we have both jerked off in front of each other now, maybe next time will be different. I promise to report any details.