Serena – a night of fucking

Who knew we would have a night of fucking?

Serena and I were scheduled to meet at 8 in the bar of a hotel that I used a lot back in the bad old days but don’t think I’ve been to since then. I arrived a bit early, checked in, got an extra key, and went up to the room. I had with me a bodysuit which I had previously given to Serena and then taken away from her. I hadn’t told you that – I don’t tell you everything! I also had a little rope. And a sushi dinner.

Because we were meeting at 8, because I was exhausted, I didn’t want to waste time out in the world. Yes, Serena and I have been talking about going to a shitty nearby strip club together, about going to a sex club together, and the day before I had thought this might be a night on which we went to a strip club together. But as the day progressed, I realized I was just too exhausted. I barely had enough energy in me to show up for this date. It was only my excitement at seeing Serena, at seeing her tiny, lithe body, and at connecting in the ways that we do so well, that enabled me to overcome my exhaustion.

As I entered the room, a flood of memories washed over me. Suddenly, I remembered just about every date I had had in this hotel, all at once. Every one of them, best I can remember, was paid, all dates in the darkest days of the before times. Nonetheless, some of my fondest memories (or at least, least un-fond memories) from that period took place in this hotel. Multiple dates with the Porcelain Doll, a number with the Secretary, a number with the Party Planner, with Willow, and with various friends of Willow and the Party Planner, who themselves were friends. Now that I think of it, I think Willow and the Porcelain Doll might even have been friends.

I had a memory of the Porcelain Doll getting herself off with an electric toothbrush, and of my spanking her ass so hard that she cried, and her thanking me for it (a first for me).

I had a memory of the Party Planner’s ankles pinned behind her ears as I plowed into her from above – a rare fucking in those days.

I had a memory of Willow’s soft mouth.

And coursing through all those memories was another, jarring memory. The memory of the sounds and sights of the construction taking place immediately below the hotel on the site of Ground Zero. Debris being removed, trucks coming and going. It wasn’t a romantic or a sexy scene by any stretch.

So, with all these memories coursing through me, I set up the room, washed my hands, and went downstairs to the bar.


I arrived at the bar twenty minutes before our appointed time. Serena had some difficulty extricating herself from work, where she has a difficult, demanding, and somewhat crazy boss. She didn’t make it to me until 8.30, by which time I had had two scotches and, tragically, devoured my half of the sushi.

I haven’t written much about my struggles with my weight, but after I lost fifty pounds, I have managed to keep it off, but only by starving myself, or at least so it feels. If my body takes in more than 1,600 or 1,700 calories in a day, even a day on which I spend twenty, thirty, or forty minutes on an elliptical – which is actually almost every day – if I eat more than my allotted calories, I gain weight. At the moment, I’m about seven pounds above the lowest level I reached, which was 156. I’ve had a loose goal of someday touching 150, and a somewhat more serious one of living my life under 160, but honestly, I haven’t been under 160 in over a year, and I’ve bumped up over 170 more than once. The way I manage (or fail to manage) this, for the most part, is by starving myself a fair amount prior to dinner. On this particular day, I had had oatmeal with raisins and cranberries and a taste of peanut butter for breakfast, a deeply unsatisfying salad with no protein for lunch, and two snacks throughout the day – a hard-boiled egg and a banana. For a growing boy like me, by the time 8:00 rolled around, I was ravenous… and, sufficiently uncertain about Serena’s eventual arrival that I couldn’t didn’t any longer resist my hunger.

Add to that, it had been a week since my last cigarette, and anyone who has quit smoking knows what quitting smoking does to the appetite. So much as I would have liked to preserve the opportunity for a semi-romantic meal, or even just the experience of eating together, by the time Serena showed up at 8:30, the lovely platter for two that I had bought was missing half its original contents.

Ten minutes before she arrived, Serena texted, “I’ll be there in 5 minutes. Order me something with cucumber in it.”

I scanned the menu and found nothing. I sent her a copy of the cocktail menu and said, “Nothing with cucumber.”

She replied with the name of the drink on the menu that clearly had cucumber.

“Whoops!” I wrote, “I don’t read so good.”

I returned to the bar from the room where I had just been devouring the sushi. Positioned myself at one end of it and ordered us our drinks. A couple of moments later, Serena entered in jeans and a soft ribbed tank top with a broad, genuine smile – she was happy to see me, in a way that matched my pleasure at seeing her.

“Holy shit, isn’t her body cute?” I thought, but don’t think I said. The nipples of her A-cup breasts were eagerly making their presence known through the ribbed, black, taut fabric. The jeans were loose, but not so loose as to obscure her tiny but pronounced curves. As she sat down, we pawed each other eagerly. “I like how your body feels,” I told her, and I do.

“I like how your hands feel on my body,” she said, and she does.

Usually, I’m the first to issue a bona fide compliment. On this evening, I’m not sure why, but she beat me to it: “to me, “You look so hot!” she said.

A nice feature of Serena’s and my relationship is that we both struggle to contain our ardor and enjoyment of one another. So as we drank and pawed, we caught up. It had been a while since we’d seen each other, because her family had been in town for an extended visit. She had a second drink. I nursed my third. Finally, I said, with some desperation, “Can we go upstairs, please?”


My plan had been to get Serena back in the aforementioned black bodysuit. And to have her sit in the bodysuit eating her dinner while I periodically interrupted her progress with her magic wand. That had been my plan. In the event, that wasn’t exactly how things proceeded.

For the first ten or fifteen minutes we just rolled around on the bed – the king-size bed onto which I had tossed her moments after we entered the room. I could feel that my cock was behaving a little bit different than it has in some time. I could feel that, as with my surprise with Milica just recently, this night was going to be another night of a fucking surprise. I didn’t, thought, understand that it would be, at least for me, a night of fucking.

I don’t remember the progression of events. I never do. Roughly speaking though, it began with teasing. My teasing her for a long time. I really like teasing in general. And I really like teasing Serena in particular. I like to imagine I’m unusual in her life. In the attention I pay to her pleasure. In the extent to which I put her pleasure in the foreground of our time together. This isn’t an act of generosity on my part. There is genuinely nothing hotter to me than harvesting the power I wield to deliver pleasure.

And so, after much teasing, and – I think before any eating – I announced, “I want my cock inside you.”

Serena smiled, and said with some encouragement, “Don’t think too much about it!” and reached for a condom.

I said something like, “Shut up, don’t worry about it, I’m good.”

I don’t know how I knew that this was true, but I did.

For so long it’s been so unusual for me to feel confident that the simple act of fucking will be uncomplicated for me. I had that confidence in this moment, and I was right.

Serena expertly applied a condom, and lowered herself gently onto my cock.

As familiar as I am with female anatomy, as practiced as I am at interacting with it, the positioning of genitals for the act of intercourse is just not an act that I have as much practice at as many others. And so, at least on this evening, every time my cock entered her, my cock entered her, Serena was the one who navigated the transition from outside of her to inside of her.

Prior to dinner, she rode me. She rode me for some time, coming several times, expelling me once, with a squirt, before I flipped us over into missionary, and continued.

Missionary is not my favorite position. Somehow, it doesn’t give me the friction and stimulation I crave. (And even less so does doggy-style.) I didn’t lose my erection, but I could feel that this just wasn’t the right position for us to be in for too long. And so I rolled us back over, put her back on top of me, and we continued.

I’ve recently been thinking about sex, about how long people take to have it, about how long it takes people to have it, about my preference for sexual interactions’ duration to be measured in hours, not in minutes. When the day had begun, I had imagined I might not have the stamina to last very long. It had been an uncharacteristically long period since my last orgasm. I was feeling deprived, hungry, a little needy. In fact, though, my stamina was all that it ever is. And Serena and I fucked for what I would guess was fifteen or twenty minutes – and more orgasms than I can remember – before I pushed her off of me, saying, “Put on your bodysuit. Eat your sushi.”

She did as instructed. (She always does as instructed when we’re together. She almost never does when we’re apart.)

The next stretch of time consisted of conversation, idle chatter, continued connection, but at a six or eight foot distance as I lay on the bed, touching myself. Soon, she too was touching herself.

We had discussed how hard it is for her, how surprisingly hard it is for her to share her private orgasms with me. She shares her orgasms with me when she’s with me, but she can’t when she’s alone. She knows she’s supposed to – at least those that are produced with the wand I bought her. But somehow she’s been unable to do it.

I haven’t introduced into our relationship the magnitude of discipline that her disobedience would seem to require to be removed. To be honest, I haven’t experienced her disobedience so much as disobedience as an honest attempt – and failure – at obedience, at compliance. And punishment seems somehow the wrong response.

This is why at the end of the evening she left with both the bodysuit and the wand, both of which, at times, I contemplated confiscating from her.

She finished her dinner and we had a reunion at the edge of the bed where I had her kneel before me and suck my cock for some time before moving us once more to the bed….

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