I Play Hard to Get. You Know, Sort Of.

At the door to his apartment, Dean kissed me firmly. I panted as he mashed his mouth against mine – it was hot and I’d just climbed five flights of stairs.

Since I’d last seen him the cuts on his face has healed somewhat. He was unshaven, and I was astonished at how good he looked—usually I prefer my men clean shaven. But disheveled and bruised was a look I found appealing on Dean. Perhaps because it mitigated his otherwise hardcore preppiness?

For the first time I got a good look at Dean’s apartment – on our first date I’d been too drunk, not to mention distracted by the sight of the blood pouring off his face, to notice. But now I looked around. We were standing on a lovely oak floor. Next to me was a kitchen, about eight feet wide and five feet deep, tucked into the wall. It held a small stove, a half fridge and a marble countertop. The foyer and kitchen were divided from the living room by a low rail and few steps. The living room had a fireplace – a gas one or something, since the chimney was blocked. Boxes were piled up everywhere.

“When did you move in?” I asked.

“February.”

“Ah.” I followed Dean up the lovely oak staircase to his bedroom. The room was dominated by an unmade bed pushed to the center of one wall, and against the far wall was a row of closets lined with mirrors. The wall opposite the bed was a glass door, leading out onto his deck.

“I’m just going to send an email,” Dean said. “Go on up, and I’ll be there in a minute.” I opened the sliding glass door and stood on his deck, looking at the roofs of the buildings opposite. Then I climbed up a flight of wooden stairs to the roof, which had a number of potted plants and the hammock we’d gotten comfy in the other night. I maneuvered myself into the hammock and read a little Harry Potter, enjoying the warm, mild evening. After a few minutes Dean joined me, and we arranged ourselves with him on his back with an arm around me; me on my right side curled up against his chest.

We had tentative plans to join some friends of his who were watching a movie, but really what I wanted was a replay of the other night (though without the brain trauma): a long, boozy meal and lots of fooling around.

We were debating our options and I mentioned something about my apartment when Dean asked me how much I paid in rent.

I told him, though I couldn’t quite believe he’d asked. “That’s a bit less than I pay on my mortgage,” he said, looking at me from the corner of his eye.

And suddenly it occurred to me that Dean was rich. I mean, richer than I’d guessed, and I’d guessed he was pretty rich already. Some of the things he’d said on our first date made it clear that both of his parents, at least, had an awful lot of money, but I hadn’t thought much about it. I mean, my parents have some money, but it doesn’t affect me – it’s the result of forty years of two incomes and rising home prices in New York City and is earmarked for their threatened retirement to Florida, where they plan to spend their days power walking at the Aventura Mall and watching every film released in Broward County.

So I hadn’t paid that much attention. I assumed that Dean had some money socked away from his days as a television writer or perhaps a parent had loaned or given him some cash for a down payment. But as I stared at the dimming sky it hit me that no bank I knew of would loan money to an aspiring poker player. Not for this apartment, anyway.

I didn’t say anything. Because while I had no qualms about my poverty, I felt really, really funny about saying to him: “Dean, are you rich? Like, really rich?” for fear it would reveal me as a shallow gold digger. Rather than a shallow sex fiend. Oh, so that was why he’d dismissed my offer of a contribution to dinner the other night with a casual “No, I have way too much money.” He had just been being truthful. Ah.

We were running late, but when we went back inside Dean sat on the edge of his bed and tugged me close to him. We were eye to eye. We kissed. “I want to spank you,” he said.

I caught my breath. I was in the apartment of a man I’d known for a total of three days, and no one knew where I was, and he was seven years older than me and…

His bed frame had built-in drawers, and he opened one now, and took out a thong of suede-like fabric. Dean indicated the sand-colored, cushioned wall inlay behind the bed: “This is from when I had that done,” he explained.

“Chamois,” I choked.

“Chamois,” he agreed. He sat on the edge of the bed and looked at me: “Now you’ve got an older man who knows how to discipline you,” he said mildly.

Oh, my God. I was so excited I forgot to be scared.

He pulled my hands behind my back and tied them with the chamois. I stared at him, wide-eyed, docile, and then he pulled me across his knee, so I was facing down.

I stared at his sheets: “Um, maybe you want to move your socks. And possibly The New York Times.” How was I going to get into the right frame of mind when I was distracted by tube socks and other evidence of Dean’s normal, non-threatening guy-ness?

“Oh, right, yeah, that might help.” He swept some of the junk off the bed. If I have men over, I at least make my bed. Jeez. He must have had months’ worth of Sunday magazines here.

At last the stage was set, and Dean smacked my ass – still clothed – with a quick, brisk hand.

“Start really soft,” I said, and was dismayed to notice that I was hardly being submissive here, what with the giving of orders and stuff. But he obliged. He hit me, and I started getting really excited, but we were supposed to meet his friends so it was brief.

We stopped by to see his friends but ended up going to dinner by ourselves. By the time we made it to an Italian restaurant the sky was dark. It was warm and we sat at a table on the sidewalk, our knees touching under the table. Dean rubbed his hand along my leg and squeezed my ankle.

We split a bottle of wine and ate bread and olive oil and I struggled over the menu, trying to decide on an entree. When the waiter came I was still debating. “We’ll share the steak salad for an appetizer.”

“How do you like the steak?”

“Medium rare?” I was leaning toward the homemade pasta and not really paying attention. “Sweetie?” said Dean. “Is medium rare OK?”

“What? Oh, That’s fine.”

We had a nice boozy meal, as I’d hoped, and it occurred to me that this would be a nice way to spend my life, eating at the sidewalk tables of Italian restaurants on summer nights, drinking Pinot Grigio with a cute guy who called me sweetie.

Afterwards we walked back to his place, and in his room he tied my hands behind my back with the chamois again, and put me over his knee, as I’d known he would. It was dark in his bedroom, and I whispered, “Tell me why you’re hitting me,” and there was a note of longing and thrilled anticipation in my voice.

Dean slapped my ass: “This is for making me get an AIDS test,” he announced, and then he hit me again. I breathed rapidly. “And for not calling me ‘Sir,’” he added thoughtfully, bringing his hand down on my ass. I swallowed. “Because you’re a whore and a cum slut and you need to be disciplined,” he went on. His words washed over me, a flood of all the dirty things I whisper to myself when I masturbate, and I was gasping and he was hitting me while I squirmed against his hand in the dark. His hand was nowhere near my clit, but I was amazed to discover I was totally wet. I rubbed myself against his jean-clad thigh, shuddering and moaning.

After a while his hand subsided and he wrapped his arm around my back. I lay with my face buried in his chest. I felt very, very strange, sort of hollowed out and almost ashamed and what we’d done, or of how I’d enjoyed it.

“If you get tired, you should stay over,” Dean offered.

“OK,” I said.

After a minute I rolled away onto my back. My hands were still tied together, but the lack of movement didn’t bother me. Dean slid on top of me and kissed me. “I want you to stay over,” he said.

I wrapped my bound wrists over his head and around his neck. I kissed him back. “OK,” I said again.

He put the movie Secretary on, perhaps so I could get an idea of what was in store for me, but we didn’t pay much attention since he had his hand on my clit and we were kissing and rolling around. I was surprised at how funny the movie was, though; I’d never watched it before.

When it was over we lay in the dark. “You know what I want?”

“Hmm?” I nuzzled his neck.

“Ah, Lily, I want to wrap myself in latex and slip inside you,” he whispered.

I considered this: “No, I’ve made such a fuss about it.” Best to start as you mean to go on. “I’ve got to see it through. We’ll do it on Monday, when we’ve both been tested.” That was my plan: after we'd both been tested (on the following Monday, provisionally), we'd make a beeline for his place and get naked. This is my idea of playing hard to get.

“Listen, you’re going to stay over three nights a week.” I didn’t respond; I didn’t know what to say, though the idea appealed. And I thought: Dean lied to me: he is interested in a serious relationship. Maybe not with me, that wasn’t entirely clear to me — perhaps it was just that I was in the line of fire, and all his good manners and affection and boredom were spilling onto the first available girl. But he’d been so attentive, and asked me to do social, non-sex stuff -- did I want to meet his friends? Should we see a movie? – it was clear that he wanted someone to socialize with. But. He was so nice and smart and funny and kept seeking my company so I thought: Don’t be surprised if he disappears in two weeks. Dean came on strong, and my recent experience with men who showed this much interest in me (like Evan, for instance) hadn't proved very positive. Perhaps Dean was a hit-and-run kind of guy: I had no idea.

But I wasn’t going anywhere tonight. When Dean turned off the light he snuggled up against me. I wasn't expecting that, I wouldn't have taken him for a cuddler. I’m a restless sleeper and couldn’t have his limbs on top of mine. But whenever I tossed and turned he would tug me back to his chest, and I fell asleep with the sensation of his arm clutching me close.