Me For Two

Since I had my first couple of experiences with same sex hookups, I had been searching hookup sites, looking for my next experience. My first encounter was magical. I was full of excitement, nervousness, and the sex was fantastic.

My second encounter was with a cross dresser. I thought this would be highly erotic. Being feminine, and looking feminine need to go hand in hand for me. His photo looked sexy enough. He was in the construction industry. I give him an "A" for effort.

When I see a photo of a man dressed as a woman and really looking like a women, that's fucking hot as hell. This was not the case. I'm thankful I had the experience, but the situation was not ideal, an air mattress in the back of a maintenance van does not suit me.

Back to searching for an ideal hookup. This next encounter took three months to materialize. There was a post in the hookup site a like to browse about two weeks ago. A male couple lost their (hookup) due to relocation, and were looking for a new semi- steady third person in bed. They were close to my age, slightly thinner and taller, but not too much different. Oh yeah, and they host, this is huge for me.

I sent them a reply to their post, saying I thought I might be a good match, that I live close enough by, and that we had similar shapes and sizes, and desires.

I sent the reply, and moved on. I think I sent a couple of emails that day to different posts. A couple days later I remembered that I might have a reply. I have two gmail accounts, one up front, and the other down low. My down low one does not get notifications, and I swiped on it.

To my surprise I had a reply from the male couple, wanting to meet me, they were going away this weekend, but would be available on 12/17.

After their weekend away, they emailed me, making sure things were still going as planned. They are available at night and we planned for 9:30pm. We sent emails back and forth.

Jerry and Tom had mentioned in one post that both like anal/oral giving and receiving, and were into a little kink. Okay, now I'm curious. My next reply, I let them know I was curious about their kink.

They informed me that with their previous partner they would cum in his ass then clean him up orally. Okay, not too kinky, but yeah. They asked if I had any fantasies. Yeah, I do, a whole bucket full. Some fantasies should just stay in the mind, and not be fulfilled. If you play out all your fantasies, then what?

I informed them I would like to be restrained and fucked, maybe with some role play. That sounds hot to me.

The following week seemed like it took forever for Friday to reach. My car was having some intermittent electrical problems, keeping my fingers crossed that it wouldn't act up. My car held up thankfully. I arrived promptly at 9:30pm.

Jerry answered the door, looking me up and down. I shook his hand across the threshold, he invited me into their layer. Beautiful house these two had. Jerry offered me a drink. I chose diet coke. To open up the conversation. Jerry told me he and Tom were upstairs pumping, (penis pumping) which they said they did, as did I.

Tom was coming downstairs, and heard him say, "Stuart, is that you?" I could tell he was pleased that I showed up. We shook hands, and I gave him a hug, just to kinda break the ice. We made small talk, I talked about my drive, it had been snowing a little, but the roads were clear.

Jerry asked if we should go upstairs, Tom and I agreed. Tom headed up first, followed by me, and then Jerry. I did a little hip swaying in front of Jerry to be a little flirtatious, it may have turned me on more.

We entered their room, there was a gay porn video on pause as a guy was riding another in a reverse cowboy position. Tom offered me a towel and the restroom.

I relieved my bladder, I hadn't eaten anything except a Slim Jim and an energy drink, and a bottle of water to wash down a Viagra. I gave myself a double enema that morning to be squeaky clean, not knowing where the night would lead.

I slipped my clothes off quickly and wrapped the towel around me and exited the bathroom area to the bedroom. Jerry and Tom were standing around the corner naked, with cock rings on. I pulled the towel off, saying I guess I won't need this, and tossed it back to the bathroom. I reentered the bedroom, the porn video was now on.

I stood between them and grabbed both their swollen cocks, Tom grabbed my cock and started stroking it then rubbed my cock against Jerry's cock. Tom asked if I wanted a cock ring. He put one on me that separated my cock from my balls, and another stretched over my entire package.

Tom then went down on me, and Jerry and I embraced in a deep long french kiss. We then moved to the bed. They have a king size bed, so there was plenty of room. We were in a triangle position all with cock in our mouths.

There was some repositioning, I ended up on my knees bobbing up and down on Jerry's cock while Tom was lubing my ass. I felt a finger slip into my ass. I let out an accepting moan and rocked my hips while taking all of Jerry's cock in my mouth.

Jerry was really enjoying my work, then I felt something bigger and longer penetrating my inner ass. I love that feeling, wondering if there were bigger things to come. Tom pulled out the long thin dildo, then cleaned me up. I then stood on the floor with my legs spread and leaning over still working on Jerry's cock.

Tom was on his knees jacking my cock and stretching my ball sack. He then started swinging my cock, making my balls slap my ass. This must have really turned him on, it was different for me, something new and I enjoyed that. Tom stood up quickly and apologized to Jerry because he couldn't hold it and came.

Tom then climbed onto the other side of the bed and laid back next to Jerry rubbing himself, exhausted from climaxing. I got on my knees on the bed, grabbed Jerry's head and guided my cock into his very willing mouth.

It wasn't long before he had me on the edge of dumping my load, so I stopped and went back down on him, stroking him while swirling my tongue around his swollen head. He started bucking wildly, I tried to keep his cock in my mouth, but he was bucking too fast.

I kept stroking him as he let out a groan and climaxed. I kept licking the tip of his cock tasting his warm jism which tasted like mine (don't ask me how I know that!)

I pivoted back to his mouth. This time I was ready to cum. I haven't ejaculated in about three weeks. I grabbed the back of Jerry's head again and was thrusting my cock in his mouth in a frenzy, without any thought to Jerry. I let out a loud groan and shot a huge load into Jerry's mouth and throat. I thought it was going to come out of his mouth, but he took it all with pleasure and commented what a large load it was.

We all were done, and just laid on the bed catching our breaths. The porn video was still playing, with moaning and groaning.

I mentioned that they were still going at it. "Must be nice to be young" I say, and they agreed.

There was silence, that awkward silence that you sometimes hear about. Thinking to myself "are we done," yes we were I figured. We chatted for a bit, laying on the bed. We discussed that maybe this is a good match, and they asked when I could come back. This delighted me. I got up and said I needed to clean up. We all got up. I cleaned up and got dressed, then we went downstairs. I finished my soda, and put my shoes on. We said our goodbyes, I gave them both a hug and a kiss.

I drove down the road a bit, stopped at a gas station and parked, got out and had a smoke. Then I drove home. Today was a good day.

A couple hours after I got home I reached down and grabbed my cock (as guys sometimes do) and discovered I still had the cock ring over my entire package. It's one of those really soft and stretchy silicone rings. Good thing my wife wasn't in the mood!!

I'm excited to see them again. We have covered the basics. I want to urge them to take things further. I would still like to be be restrained and fucked.

As of yet, I have not felt a hot cock in my ass, which I strongly desire. Someday I want to have a safe word to use!! I am a bottom and want to be treated as such. I also need to learn some top skills as well to be more versatile. This couple may help me.

I also need to get back to my first encounter, hopefully soon. I want him to slow down and stretch me properly :).

Today was a good day.