Try not. Do… or do not. There is no try.

Thanks Yoda! Ok, so I am by far not a huge Star Wars fan, but couldn’t resist using that quote because it so perfectly embodied my evening last Thursday.

The wife and I both had separate evenings out with separate partners of our bi couple friend J&R. Just like the guys night out R and I had on Friday, my wife and J had a girls night out. It was much tamer, but was a good start. They have other plans in mind to explore for a future date. But while that’s great they are doing it, and I’m all about encouraging them to do it again, that’s not the point of today’s blog.

Since the girl’s were going out R and I decided we should hang and have a night in.
[Pause for readers’ minds to drift into the gutter. Good to go there now since that’s where we’re going poeple]
After work I took the quick subway right out to their place. R is taking a break from work (works independently so he can) so he was very relaxed. Seems like he spent most of his day on craigslist arranging a weekend of debauchery. Well, the plan was for a little evening of debauchery ourselves.

On our guys night out we talked about the fact that while it has been fun exploring with others often times things don’t lead to me getting fucked or even my ass played with. When we meet with single bi guys it makes sense that the focus is gonna be on my wife even if there is some mutual cock sucking going on. When it’s another couple… well, there is just to much other fun stuff to do. R decided that we would need a night alone at their place sometime for him to take me on a tour of their private toy collection.

So that was the goal of the evening, but I will admit that I was hoping the toys would lead to a good old fashion fucking

Ok, I’ll fast-forward through the highlights of the early part of the evening. Had a drink; Hung out and talked; Checked out an Undergear catalog together; Smoked some pot; Went out to dinner for food; Got back to the apartment.

R wanted to take a shower. I didn’t see a reason, but hey whatever because it led to me finding out about their extensive collection of erotica. Apparently R prefers his porn written (though there are videos as well). He gave me a well used edition of Penthouse Letters with his favorite story for me to read and said that if I lost some clothes he wouldn’t mind. I was surprised because it was a bi story. I knew Penthouse could be out there sometimes, but didn’t expect them to go there. It was a perfect way to pass the time while he showered. It was a long read, but was well paced and got me going. I finished just as he got out of the shower.

I have taken my shirt and shoes off and had undone my jeans. We moved into the bedroom and were just two guys in our underwear in bed. Though as a general rule any combination of people in bed in underwear is very good by me (yeah, I have an underwear thing — wouldn’t call it a fetish exactly, but…).

We started out with some light making out. I was certainly taking the passive role here, which was fine with me. I was laying on my back with R on top of me, which is a sensatin I love feeling. I love having someone on top of me, feeling their body pressed against mine. The feeling is certainly different if is a woman or a man, but I don’t have a preference of either.

R then worked my cock and probably gave me one of the best hand jobs ever. He could have spent the rest of the night stroking my cock for me and I would have been happy — well, mostly. That’s when he decided to try and move things along and fuck me. I thought I was getting a tour of the toys, but if he wanted to jump to fucking me — OK!!

Alas, though it’s been over a year since I had been fucked and despite my own “work” my ass was gonna put up a fight. That’s when he moved on to the toy box.

He made me close my eyes while he selected his toy of choice. With some proper lubing he pressed it up against my ass. I wasn’t about to let him tease me so I just pushed right into it. If I had to have guessed at that moment what it was I would have said beads. I felt a lot of pressure and then it seemed to pop in. This was repeated a few times as I pushed further on to it. Once he got a good amount of it in my I was feeling pretty incredibly. The sensation of having your ass played with is incredible. It’s so completely different than the more tradition sex acts guys engage in.

R was very much enjoying working the toy in me, and I think he was getting worked up by it because he decided to pull out and try to fuck me again. (Oh and by the way… it wasn’t beads, but rather a plastic dildo that was ribbed). However, despite being worked a little my ass wouldn’t cooperate.

I think he was truly disappointed because after trying (and not being able to stay hard — common problem with guys who have tried to tap me) he laid down next to me. However, I hadn’t gotten what I wanted.

So I decided he needed a nice blowjob to really get him hard. R probably has the greatest cock I’ve seen so far. It’s a great modest length (he says 7″), but it’s thick. In fact in holding it I would say it’s got a great “heft” to it. It’s also the best cock I’ve sucked. I can really work his cock with my mouth and tongue and I can deep-throat him almost completely (though not completely which only means something to look forward to in future sessions). What was great was that I really felt like I was able to turn him around. He seem defeated and ready to give up on the night, but I was taking control and getting him back in it through skill alone.

Since I had decided to take the active role and I had him pretty hard I figured I’d contine taking the dominant position and try to take him myself. I figured if I was able to have more control over taking his cock my ass would cooperate. Though it appeared like strike 3.

However, R wasn’t finished yet. Guess I had reinspired him. He had me get on my hands and knees and take me quite classicly — doggy-style.

If there is anything I learned from Thursday night it’s that I should always start on my hands and knees. The angle seemed to be exaclty what I needed. Maybe it was the constant trying, but once we shifted to that position it was smooth sailing… in as much as him fucking me. The other side of not getting fucked often is that while I know he just wanted to let loose on my ass and fuck me deep and hard there was only so much I could take. That’s not to say he didn’t try and I didn’t take a lot of it. After a good 15 minutes of him having me moaning in pure pleasure and near delirium we stopped. I would have liked to know that fucking me got him off, but not that night.

We knew the girls would be finished with their night soon. So we hopped in the shower together (again a favorite). It was a very nice way to finish the evening. The funny part was that J came back from her night out with my wife just as we were getting dressed. It was a little funny, but was perfect timing.

As R walked me to the door I thanked him for another great night and said “Good beginning.”

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