I Put Out. So, No Big Surprise.

Dean greeted me at the door. Again, he was unshaven, which, again, I found pretty damn attractive. We kissed.

“Hi.”

“Hi.” We looked at one another: this was it. After eight days of fooling around, we were going to have sex: it was our third date, after all.

“Oh, wait,” Dean shuffled through some papers, and handed me one: “Here.” It was his test results from the Callen-Lorde Community Health Center where he, and I, had both been tested for HIV. Negative, it read.

“I have one too!” I’d forgotten. I rummaged in my bag until I found it, and handed it to him. “Hey, was your counselor Samuel? Wasn’t he nice?”

After the finger prick blood test I’d been counseled by Samuel, a very kind African American man maybe ten years my junior. He’d asked me about my sexual habits, and congratulated me on the fact that I use condoms religiously, even with “primary partners” … I don’t actually have a primary partner, though. Then he’d told me my test was negative, he’d give me a call in a few weeks to check in, and have a nice day. I’d left, jubilant, and phoned Dean. “Guess what? Samuel congratulated me on my practices!” I’d meant my safer sex habits.

“I’ll bet he did,” Dean’d said. Ho ho.

“That’s totally inappropriate,” I’d said. But I was laughing.

“Yeah, he was a nice guy,” Dean agreed now. Then I dumped my bag on his floor and went upstairs to his room.

His bed was still a mess: “I see you’ve been setting the mood.” I climbed onto his bed and sat with my back to the wall.

Dean stood next to the bed. We looked at one another. “Are you hungry?”

“Not yet.” Here was the moment, after all. The third date. It was time for sex. “Are you?”

He shook his head. “I was thinking you could give me a blow job,” he said.

“Oh, you were?” This got my back up a bit. We were supposed to be having sex, but all he wanted was for me to go down on him? I mean, all things being equal, I was more than happy to blow him, I just didn’t like the idea that this was his first and best idea, like I owed him or something.

“Yeah. Well, I went down on you…”

So he had. Twice. “OK,” I said. Slowly I took the hair band from my wrist and wrapped my hair in a ponytail. Dean sat on the bed and leaned back, until his head was in my lap.

“Let me warm up,” I said. I wanted to be in the right frame of mind. I wanted to fool around a bit before diving at his dick. We kissed, and I studied his angular face, his expression.

“Should I shower?”

“No, you’re fine.”

Dean stood up and stripped down to his underwear, so I lifted my shirt over my head, and wriggled out of my skirt, tossing my clothes onto the floor. He stood in his boxers, and I reached over to stroke his dick through the thin cotton. There were splotches of pre-cum on the front. I rubbed my hand up and down the opening. Then I slid the boxers off and wrapped my mouth around his cock.

He moaned. I moved my mouth back and forth, tonguing him.

“Wait,” he said. “I want to sixty-nine you.”

He sat on the bed and then slid underneath me. I shifted on top of him until we were mouth-to-genitals, and he pulled down my underwear. As an afterthought, I unhooked my bra. His tongue flicked at my clit and I stiffened with excitement. I took him all the way in my mouth, fighting my gag reflex. He moaned again, and my legs shook as he slid his tongue up and down my pussy, really fast. I let out a little gasp.

I threaded my fingers through the coarse, curly hair around his balls, then slipped one into my mouth. My legs twitched again as I pushed my pelvis towards his mouth. I went back to his dick, more eager than ever. “Come here,” I whispered; him going down on me was distracting me from making him come.

He tugged himself away from my cunt and stood with his dick dangling in my face. I looked up at him under my lashes, then rubbed him against my breasts. “I’m going to make you come,” I explained. I went back to sucking and licking; I couldn’t get enough of his cock, and I wanted him to come all over me.

He came quickly, with a grimace. I looked up at him again as I slowly rubbed his come into my breasts, playing with my nipples in the hopes he would find this hot.

Dean slumped beside me and for a moment we looked at one another in silence. Then I smirked at him, and he gripped my hand.

Dean’d drawn the curtains, but there was a faint late afternoon light through the windows. We were cool and cozy in his bed. I leaned against his arm. We talked in a desultory manner for a few minutes, and then Dean mentioned that he was planning to go to Atlantic City to play in a tournament. He hoped to win a place in the game.

“But if I don’t place I’m committed to buying into this tournament anyway,” he explained. Then he told me how much it cost to buy into this game. It occurred to me that this was a man who, so far, I had not seen with anything amounting to a steady job.

“Um, Dean? Can I ask you something?”

“No.” But he smiled.

“Are you …” I paused, completely at a loss as to how I might phrase this: “… independently wealthy or something?”

He smiled wryly. “What gave it away? Was it cause I have a deck, in addition to the rooftop?” He pointed over his shoulder, towards his very nice deck, which boasts a grill and matching lawn furniture.

“Yeah, that, and maybe the fact that you had a live in nanny. And grew up in a house in Manhattan.” This he had revealed on our first date. I gazed at him covertly. This was what an independently wealthy person looked like. Naked. Well. It was time to change the subject: perhaps my discomfort with talking about money is a middle class habit? “Well, you’re buying dinner then.” I kissed him.

“Do you want to go to this party?” That had been the original plan: go to a party at a Brooklyn bar, then return to his and consummate our relationship, such as it was.

“Fuck it, let’s go get dinner and get drunk,” I said. So we did.

**
When we got back from dinner we stretched out on his bed. He slid between my legs and examined my underwear: black nylon mesh bikinis. “I’m going to rip these off,” he announced.

“What? That’s my underwear!”

“They’re already kind of worn.” So they were; rubbed thin at the crotch.

I sighed. “Oh, go ahead.” A couple of other guys have ripped off my underwear, they all seem to get a kick out of it. I suppose it’s quite a macho gesture.

Once I was knicker-free, Dean slipped his tongue right against my clit. I swallowed as he swirled his tongue around my lips, tapping against my skin. My legs shook.

After a moment Dean stood up, and reached into one of the drawers built into his bed frame. He took out a condom.

“Kimonos?” I’d never slept with a man who used those.

“They’re very thin.” He fiddled with it until it was snug on his dick. He lay down on top of me. We looked at one another. With a grimace, he struggled to fit himself inside of me.

“I want to get on top,” I said. ’Cause usually I’m on top first, I come, and then the guy I’m fucking is free to do what he likes. Well, within reason.

“Sweetie,” Dean grunted, “You’re going to have to wait.”

Eh? Why was that? Dean pumped himself against me. His eyes were on a spot somewhere behind me.

I pushed my pelvis up against him and let my voice go slack and breathy. “You like that? Tell me.”

“You’re a slut,” he said obligingly. “A tight little slut, with your warm, wet pussy…”

That was good. I shoved myself up against him more. “Yeah. Come on, Dean. Give it to me.”

“Lily.”

“Mmmm.”

“What’s today’s date?” he panted. “August first.”

“Mmmm.” I pushed my mouth towards his.

“Lily. On December first.” Dean kissed me, “If we’re still fucking, then we’re going to both get tested again and I’m going to start fucking you without a condom.”

“Ummm. Can we have this conversation later?” I gasped. “When we’re not having sex?” I mean, what was that about? I’m not having sex without a condom unless I’m in an exclusive relationship, which I was sure was not what he was aiming at, but, really, did I need to explain this to Dean while he was inside me? For God’s sake. Dean shuddered. “Say my name,” I demanded.

“Lily. Lily. Lillian Vereker.”

Lillian Vereker feels like I’m in school. “Just Lily is fine,” I said breathlessly. I wrapped my legs around his hips, and he lifted them higher around his torso, until it my legs felt the strain.

When he came I held my hands against my back, as if to keep him inside me, cause I liked the pressure and weight of his body, his cock, against me. When he rolled off I made him turn on the air conditioner. He feel asleep easily, one arm around me. He began to snore: “Veerup!” I cocked my head at the man next to me. It was the noisiest snore I had ever heard. Each snore was accompanied by a long, quiet wheeze, and just as I got used to the wheezing he would snore again. It was from deep in his chest. I stared at him, nonplussed and unable to sleep. He sounded, I decided finally, (and poetically) like the death rattle of a baby frog: “Veerup!” I put my head under a pillow and waited for the snoring to become background noise.

**

I woke up with a bad hangover and very horny. I wrapped myself around Dean, who, luckily, was amenable to being cajoled out of his sleep in order to service me, as it were. He rolled on top of me. “I want to get on top,” I said, determined to have my way at last.

“Wait,” he said.

He put on a condom and with a sigh I opened my legs and he struggled inside me. After a minute he nodded and he slid out. I crouched on my knees as he lay down, and then clambered on top of him. He fiddled with his dick and then, stretching forward, I started to ride him.

This is the position I like best, it’s the easiest way for me to come. I just rock back and forth and, if the guy stays still (I know, not very sexy), I get myself so worked up that I come very quickly, especially if my partner engages in a little dirty talk. Most men, of course, feel obliged to participate in the act, and Dean was no exception. “Stay still!” I grunted. This was not too successful. “Hold my hips,” I tried again. “No, lower.” I bounced a little on his dick, anxious just to ride him hard and come. “There. There. No, wait.”

Hmm. “Tell me to stop,” Dean said.

I looked at him. “Stop,” I said, experimentally. Huh. “Stop, stop,” I made my voice exaggeratedly whispery. “Stop.” I laughed at how coy I sounded: “Stop.” I didn’t want him to stop at all, but I wanted to keep saying it; it was turning me on. Good lord. I opened my eyes wide, half pouted, and heard myself beg: “Please stop.”

Despite this and my fevered rocking, I did not come, not even when Dean began slapping my ass lightly, as per my directions. So eventually, both of us sweaty and stuck together, he rolled back on top of me and fucked me. “Come on,” I said, my voice almost a whine: “Come on, Dean.” He obliged.

When we at last made it out of bed and into the shower, I realized I was too hungover to stand up and sprawled in the tub, clutching my forehead theatrically while Dean scrubbed his back. “Are you OK?”

“Uhh,” I moaned. Eventually I managed to get upright and washed, and after I’d tugged on yesterday’s clothes we went out to breakfast. We sat at a sidewalk café and collaborated on the crossword before all the carbs I digested made it necessary for me to go back to sleep.

We made it back to his place where I flopped on the bed. He lay on top of me and we smirked at one another, sated and smug. I closed my eyes and drifted off, enjoying my midweek idyll. And I considered that being an unemployed slut has its compensations.

Decisions, Decisions.

Oh my gosh. Alejandro emailed me!

I hadn't heard from him since last fall. We originally met in the Spring of 2006, during my original foray into the world of casual sex (not chronicled here). Alejandro is Brazilian, handsome in a clean-cut way, earnest and a few years younger than I. I’d broken it off when I decided to see Roger exclusively. This turned out to be a bad idea, so back in October I wrote to Alejandro and asked if he wanted to get together. He initially agreed, but later cancelled because he wanted to (and I quote) “make love on a spiritual level.” I couldn't fault him for that, though I'm afraid this did make me snicker, so I wished him well and that was that.

But hmmm, he just emailed me, and asked if I was available. I'm undecided. Our sex, as I recall, was nothing special. I was really taken with his looks, and he’s a nice guy, certainly, but it wasn’t particularly passionate, or sweaty (i.e. no oral sex for either of us). But I’m all in favor of quantity, not quality, so maybe this isn’t a bad idea. I’ve got to think about this some more.

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.