In my stretch of time being single between when my marriage ended and when I met Sarah, I wasn’t overly interested in sexual things. To be honest, other than I few random hook-ups, I mostly kept to myself and was content with masturbation. But one of the things I missed from my marriage was discipline, and occasionally I’d find myself searching the internet for some type of dominatrix.
There are a lot of them out there, but I wasn’t looking for a situation where I paid someone for her services. I wanted just to meet up with a dominant woman for a little bit of play that we’d both enjoy, not something professional. It was hard to find that.
Then I ran into an ad on craiglist from a local guy. I don’t hide or deny my bisexuality, but I don’t have much experience with men and I immediately think of women when I’m searching for partners. But the idea of having a man discipline me sounded immediately appealing, and I contacted him.
He was nice and polite and not overly dominating in our conversations. We talked back and forth for weeks. I told him what I was interested in and he told me what he enjoyed doing. We negotiated a few things. He was willing to just punish me, but also said he’d certainly enjoy it if there was sex involved too. I was hesitant at first, but warmed up to the idea.
Before I ever went to see him, we established an entire scene we would roleplay, down to some specific details. I liked that I knew exactly what to expect.
This was the scene: I drove to his place and he met me at the door as if we were longtime boyfriends. We kissed and touched each other, and then went to his couch and made out. The next step in our scene was for me to go down on him, and I remember I was nervous about this so I delayed it for a while by making out with him for a really long time. I enjoyed the affection and touching as I hadn’t had that in my life in a while.
Eventually I pulled his jeans off and sucked him. It wasn’t my first time, but I had very little experience with giving blowjobs and I found that I really enjoyed it. Our agreement was that I would suck him for about a half hour and then “complain” that it was taking him too long to cum. I did exactly that.
He roleplayed being angry with me for saying that, and pulled me up over his knee. It was a gentle fun spanking at first, but I’d told him I wanted him to be severe. After a few minutes, he directed me into his bedroom where he laid me on his bed and used a paddle on me. He was quite forceful with the paddle, and it definitely hurt, but it still wasn’t quite the beating I was hoping for. But he didn’t disappoint me. After about 10 minutes with the paddle, he grabbed a leather strap with a handle on it. My wife had something similar, and I knew it was good for a painful spanking.
He gave me a few strong swats with it, and I enjoyed it. Then he changed positions and started spanking me with the strap in the most forceful way I’d ever experienced. He was swinging it from over his shoulder with all his strength. I was startled by it at first, I’d never quite been spanked like this. He continued with the same strength, ignoring my reaction. I had a safeword but I wasn’t even close to wanting to use it. I yelped and screamed and had tears on my face and he just kept spanking me.
When he finally stopped, he rubbed my sore ass and started kissing it. This lead to a nice rimjob that I really enjoyed after such a beating. I knew the next step in our scene was that he would fuck me, and I was apprehensive about it. I’ve had even less experience with gay anal sex than I had with giving blowjobs. He put on a condom, used a bunch of lube, and slid inside of me.
It was a combination of pleasure and discomfort, but the pleasure was definitely winning. He was stroking me while he fucked me, and he managed to give me an orgasm simultaneously while he had one in my ass. Not accustomed to gay sex, I felt super-aroused even after the orgasm, and yet exhausted at the same time. We cuddled and kissed me and I wanted to fall asleep.
I could easily see how that would have become an experienced I’d want to repeat over and over again, but I never saw him another time after that.
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