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I Succumb to Jefferson's Dastardly Lesbian Plot!

It was summertime. The sun was shining, and I was going to Atlantic City with Dean.

I thought we were going to stay in a seedy seaside motel, and Dean would relieve elderly daytrippers of their money at the poker table while I wandered the boardwalk and sampled the saltwater taffy.

Instead, we stayed at a perfectly respectable, even luxurious, hotel and ate lots of rich food. I was bemused by the miasma of cigarette smoke and the constant musical roar of slot machines in the lobbies, but seediness was in short supply. I did buy a $4 cappuccino, however.

But my Atlantic City experience was destined to be short, since I had other plans. Or rather Jefferson had other plans for me: “The clock is ticking on your girlginity,” he informed me. “What time are you coming over?”

Oh, right.

**

It had started like this: Back in December, Jefferson had suggested I might want to get it on with a carefully selected woman. I had shrugged. In Jefferson’s orbit, being straight is a bit of a novelty and I wanted to hold onto whatever distinction I might have. Nonetheless, it occurred to me that if I was trying to Live Somewhat Dangerously, perhaps I ought to put my money where my mouth was, or rather, put my mouth where …

The thing was, although Jefferson knows tons of attractive bi and lesbian women, when you’re approaching your first lesbian encounter as a kind of adult-ed experience, it’s not like choosing a hot boy to fuck. I could agree that a woman was comely, but there was no connection between my brain and my groin, so it had no context. And I don’t like to fool around without context.

Also, I realized that there were certain other barriers to me getting it on with a woman. Like, I did not want to hook up with someone I was friends with. I can do that with men, but with a woman it just seemed too overwhelming, too much opportunity for sidelong glances, misunderstandings, etc. I wanted it to be with someone I didn’t see on a regular basis.

She would have to be more experienced, and amenable to the fact that I was a girl virgin and awkward in the extreme, I decided.

So what I wanted was someone I could be attracted to, did not know very well, was experienced, and furthermore did not threaten my fragile ego in any way. With these demands in place I felt confident that I’d outmaneuvered Jefferson and would not come face-to-pussy with my fears in the near future.

**

When I first met Jessica my only thought was that she and her boyfriend should definitely attend Jefferson’s orgies. She was pretty, brunette, and friendly, with long hair and a nice giggle. The word vivacious would have been appropriate.

Actually she was kind of like me, though I am not always vivacious. She and Sean stopped by Jefferson’s one afternoon. I was on my way out, but I stuck around long enough to echo Jefferson’s assertions that they would definitely have a good time if they turned up at a party.

Eventually, they turned up. This was at the May orgy. Jessica, stripped to her bra, made out with Jed while I watched. The next day I emailed Jefferson, “You know, if I were going to hook up with a girl, Jessica’s the kind of girl I would do it with.”

Jefferson interpreted this as a green light and took it upon himself to arrange the great lesbian experience. He sent me an email later that day saying we were all set: Jessica and Sean were game. It would be, Jefferson informed me, what was known as a “soft swap”: While she and I would hook up, Jessica would not have sex with Jefferson, nor would I fuck Sean.

I was mortified. Not only had Jefferson organized My First Lesbian Event, he’d done it in a way that made me look like a third grader. He’d probably passed Jessica a note in language arts: Do you want to have sex with Lily? Check Yes ___ or No ___.

It turned out that Jessica was likewise inexperienced with women, which I hadn’t realized. From the conversation we’d had when we’d met I’d had the impression she’d slept with several women.

So now I was committed to sex with another straight-identified woman. One who’d probably felt obliged to say yes. Gah.

**

Of course, I hadn’t actually protested when Jefferson told me we were getting nekkid. Jefferson gets me to do things I wouldn’t ordinarily do, because he arranges them and then informs me of the fact, so I never have to take any responsibility. Passive aggressive on my part, but he’s never complained. I considered this as I made my way to Jefferson’s apartment one hot Saturday afternoon. When I reached his door, I gave myself no time to consider what I was in for, and rang the bell before I could start worrying.

Jefferson peeked around the door at me: “Hiiiiii,” he smirked. I stepped inside.

Jessica and Sean were seated on the couch. “Hi!” I tried for insouciant cheeriness. They waved.

I made my way to them and, in a bold move, sat next to Jessica on the sofa rather than in the armchair opposite. I swallowed.

“Can I get you something to drink?” Jefferson twinkled at me. He knows I find alcohol invaluable in these situations.

“Can I have a gin and tonic?” I glanced at Jessica, and then at Sean.

Jessica leaned over and looked up at me from under her lashes: “We went to brunch and had six mimosas,” she confessed. Apparently I wasn’t the only one who’d needed Dutch courage. I grinned at her, and she grinned back.

Jefferson brought me a large g and t, with a wedge of lime, and soon enough Jessica and I were talking a blue streak, about how alcohol combated nerves, how she and Sean had started dating, about Buffy the Vampire Slayer.

In fact, Jessica was awesome: engaging, friendly, good natured. Her boyfriend was lovely, too: quiet, with dark hair and sort of boy scout good looks. He watched Jessica with pride. OK, he was totally hot.

Eventually, when I’d downed my second very large g and t, Jefferson indicated it was time for us to get moving. Marcus was coming over later, and, as Jefferson had told me, if he turned up while Sean and Jessica were around, all hell would break loose.

“He’d insist on an orgy on the spot,” he’d emailed me. “That might spook Jessica and Sean, so we have to finish up early.”

Jessica and I looked at one another. I raised my eyebrows. “OK?” She nodded, so we headed off down the hall.

Jefferson and Sean left us alone, as per intro lesbian etiquette, I guess. Jessica and I sprawled on Jefferson’s bed, topless, drunk, game.

“Listen,” I slurred, giggling, “I didn’t realize that you had never hooked up with a woman—I didn’t want you to think—” What I guess I didn’t want her to think was that she was, you know, obliged to hook up with me, even if we were both half naked and entirely drunk. Or maybe I was still embarrassed at how the whole thing had been arranged. I dunno.

“That’s OK,” she sniggered.

We whispered for a while, gingerly touching one another: “Your skin’s really soft!” Jessica exclaimed.

I stroked her arm: “So’s yours!” I lowered my voice, though no one else was in the room: “Can I touch your tits?” Her breasts were at least a D, with large reddish brown nipples.

“Uh huh.”

“Hey, what’s going on in there?”

We looked up. Jefferson and Sean stood in the doorway, beaming at us.

“Go away,” I mumbled.

Tentatively I licked a nipple. Jessica nodded her encouragement. “You can come back in,” I called.

The boys trooped in, and Jefferson supervised the rest of the undressing; I was too far gone to be of much use. Naked, Jessica was smooth and curvy all over, with pale skin that glowed in the darkened bedroom. The room spun, and I wondered if I should have had quite so much to drink.

I looked up at Jefferson: “Now what?”

“Now you go down on her,” he said.

“OK.” My eyes met Jessica’s. “You’ll have to direct me,” I said. She nodded.

I scooted onto my knees. Jessica’s pussy was completely bare except for a tiny thatch of hair just above her clit. Cautiously I slipped my finger against the hood of her clit. “It’s like a button!” I exclaimed. I had never seen anyone’s clit – other than my own – before.

Jefferson and Sean watched in polite silence while I studied Jessica’s pussy. Then, after a moment, I put my mouth to her clit and licked.

Hmmm.

I licked again, and then put my tongue up close to her and pressed it against her skin. In all the dirty stories (I mean, erotica) I read, women have a smell -- like pepper, or orchids, or spices or whatever. I couldn’t smell or taste anything from Jessica, though. I licked her again.

“Higher,” she said. “Steady pressure on my clit.”

I obeyed, and lifted my mouth to slide my fingers against her skin. After a minute I slid my index inside her; she was wet.

“How’s that?”

She nodded. “You can put another finger in,” she said. I obliged. “Yeah, I just get very wet,” she explained, smiling, while I slid a finger in and out. Indeed. I concentrated on her clit for a while, and then Jessica slid down on the mattress and slipped between my legs. I hoped I tasted OK.

After a bit Jessica moved away, and out of the corner of my eye I noticed Jefferson move towards her. They kissed. Then Sean leaned over from his side of the bed and kissed her, too. I was on my haunches, watching them. When Sean lay back on the bed next to me, I leaned over and whispered to Jessica: “Can I go down on your boyfriend?”

She smiled: “Sure.” Generous girl! His dick was standing straight up, full and hard. I bent over and wrapped my mouth around him, I’d never felt quite so compelled to suck someone off. It was a relief to blow him, he felt great in my mouth. A dick, that’s my natural habitat.

I could have gone like this for some time, but alcohol made things blurry and I don’t remember much else. We parted with great cordiality and later on, when I asked Jefferson if he’d seen me and Jessica kiss, he said he couldn’t remember.

Did I manage to have sex with a woman without kissing her? Worse, did I kiss her and not remember it?

**

After Sean and Jessica disappeared, I lay on the couch in an alcoholic daze. Then I perked up: “Where’s Marcus?”

Jefferson had promised I could meet his boyfriend, who was supposed to turn up with his boyfriend. So I stuck around, and soon enough, Marcus showed up with Seamus. Marcus was, just as promised, tall and handsome in the Ben Stiller vein – dark haired, lanky, gregarious. Seamus was mild mannered, built. He sort of reminded me of Grant Mitchell of Eastenders, only without the ruddiness. I generally don’t go for bald, stocky (or, you know, gay) men, but I took a shine to Seamus.

We ordered Chinese and sat around while I tried to remember whether or not Jessica and I had kissed. Marcus regaled us with stories of his life as a whore, and I tried not to look gobsmacked. Then Jefferson leaned over and whispered: “Don’t hook up with Marcus.”

I shook my head – I’m very skittish about sex workers; and anyway, I prefer my men a little less alpha. I like shy, angst-ridden boys who look like they could use a good meal or might like to educate me about some band I’ve never heard of, not hottie motormouths who have sex for a living.

Marcus was telling us about one of his clients, whom he had accused of not trusting him. “So anyway,” Marcus went on, “I had my foot up his ass and…”

He had his foot up some guy’s ass. I cast a covert glance at Marcus’s feet, currently shod. He had a big foot. Wouldn’t this be unhygienic? Not to mention exceptionally painful? Did Marcus wash his feet before shoving them up a man’s ass? Or were there foot condoms out there to prevent athlete’s…

Eventually Marcus and Seamus wandered out to the deck, and I turned to Jefferson: “He is getting nowhere near me.” I found Marcus fascinating and attractive but, also, you know, gah!

But all my gins and tonics were taking their toll, so when Jefferson suggested I stay over, I gratefully acquiesced. I took a quick shower (it was still very hot) and then put myself to bed in Jefferson’s room, wrapped in a bath towel. Some time later I felt Jefferson slip off my towel and curl up next to me.

We must have been asleep, because I woke up to the sound of Jefferson’s shrieks: “Stop it!” he cried. I opened an eye. Marcus and Seamus loomed above us, and Marcus was smacking Jefferson lightly with a DVD – Lost, season 1. What the--?

Then Marcus grabbed my arm. “Hey!” I squeaked. He wrapped one of Jefferson’s neckties around my wrist and started tying me to Jefferson. “What are you doing?!”

Hooting happily, Marcus and Seamus rained blows on Jefferson, who protested, but not very strongly. I think, in fact, that if I hadn’t been there, he would have been quite happy to have been assaulted with DVDs.

Marcus laced me to Jefferson and started swatting at me. “Cut it out!” I cried, really annoyed. I was naked, in front of two men I’d just met. When that happens, it’s because it’s my choice, not because someone has woken me up and pelted me with video discs. I glared at Marcus. “Stop it.”

“Stop!” Jefferson laughed, but Marcus and Seamus kept it up.

I leaned over and reached for my bra. This was ridiculous. “OK, that’s it,” I said.

“Yeah, stop,” said Jefferson again, pushing Marcus away. Chastened, Marcus and Seamus swept from the room, chuckling. Jefferson began to untie himself.

I sat there, wide awake, my bra halfway up my arms. Jefferson tossed the necktie to the armchair and rolled his eyes. “Ow,” he said, rubbing his arm, where Marcus had scored a direct hit.

My fists were clenched. Jefferson gave my arm a squeeze, then rolled onto his side. Within minutes, he was snoring.

I sat on the bed, staring straight ahead. My bra still hung on my arms. I could hear the low laughter of Marcus and Seamus as they got ready for bed. My hands were shaking; I was furious.

I looked again at Jefferson, nestling quietly at my side. “Jefferson,” I whispered, “Jefferson?” I tapped him on the shoulder, but he just snored.

I got out of bed and got dressed. I hunted for a pen and piece of paper and stared at it for a minute. Jefferson, I wrote at last, I tried to wake you but you were dead to the world. Talk to you soon – Lily.

I turned off the light as I left the room. As I made my way to the door I could hear the steady squeak of the futon from the second bedroom.

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.

Dirty and Clean

It was still early, and everyone was dressed. But when the phone rang our host wasn’t in the room. “Hey!” I called. “Your phone.”

“Incoming call,” trilled the automated voice: oh, that was my phone. I picked up. “Hello?”

“Hello, Lily? This is Jed Jones.” Gosh, his voice was really deep.

“Hey! How’re you?”

“I’m OK. Listen, are you going to Jefferson’s party tonight?”

I smiled at nothing in particular: “Jed,” I said, “I’m already here.”

**

But meanwhile I wanted to spend some time with Alex. He had brought his friend Amy, but she was in the midst of a conversation with a dreadlocked guy on the sofa, and they appeared to be getting cozy. Alex is so smart and easy to get along with – just nice to be around. He is shy, and I wanted him to have a good time, even though it wouldn’t be with me: it hadn’t been three weeks since we’d last fooled around, so, as per the rules of his open relationship with Katie, he was off limits tonight.

When Emma and Adam showed up I introduced Alex to them and we all stood around talking with Donny. As time wore on, Donny casually unbuttoned his shirt – a proactive kind of guy. He had a really impressive six pack, and he's super-cute, but not my type, sadly.

Meanwhile, on the sofa Amy and the dreadlocked guy were making out. I nudged Alex: “I guess that’s going well!” He nodded at me owlishly from behind his specs. Amy had told me she was an attorney, and did not appear to me at all like the type to be entwined with a stranger within 20 minutes of meeting him, but what do I know?

Cody turned up; I wanted Alex to meet her. They were both shy, sweet and good-looking, and I felt this kind of symmetry shouldn’t be ignored. However, they were in different conversational orbits, so instead I made Jefferson show me photos of his daughter Rachel’s wedding.

When Jed arrived I was chatting with Adam and Emma et al and as he leaned down to kiss me I gave him my most demure-but-sly smile. I would have gone with him into the back bedroom right then, frankly, but after a moment he drifted off to talk to Cody. I kept my eye on him, determined not to have a repeat of last month’s sex-free fiasco. Because I wanted to look nonchalant rather than desperate to get it on, it took me a while, but eventually I sidled up to Cody. She told me she had just been to meet Hanson at a record store and told me about her encounters with them (Zak is her favorite).

God, she is a sweetheart. Hanson.

Then Jed slipped behind me and put his arms around my shoulders. I tried to continue my conversation with Cody but I’m afraid I was totally distracted. Jed and I kissed and smirked at one another in a no doubt annoying manner before ambling down the hall to the back bedroom. I wanted the single bed – that’s about as much privacy you can get at Jefferson’s, unless you’re going to draw the curtain and fuck in the shower. But when we got there Amy and her new friend were sitting there, watching the foursome on the futon opposite.

The only person I could see (it was dark and, well, their faces weren’t really apparent) was Calico, the beautiful model. Her hair was in two schoolgirl’s braids and her pale body shone in the dark. It was a mash of people and as we watched, Amy walked over to the futon to get a closer look.

Jed and I settled onto the single bed next to the dreadlocked guy (I was hoping he’d take the hint and leave us the bed) while Amy edged her way towards Calico, who was facedown on top of someone or someones. Amy clambered onto the futon and bent her head down over Calico.

Calico’s head popped up: “Who’s there?”

Amy introduced herself.

“Oh, it’s OK,” Calico said, “You know, I just want to know who’s…”

I would personally have been kind of freaked out if someone put their mouth on my naked body without having let me know they were there, but Calico is apparently a laid back kind of person in that way.

I turned to Jed and we started to kiss, and at last the dreadlocked guy gave up the bed and we were free to stretch out.

We were slipping out of our clothes when others – I’m not sure who, but definitely Adam and Emma and maybe Carlotta, too, I think — tumbled into the room, laughing and chatting. Jed was lying on top of me, and I wanted him to cover me up completely: I felt really exposed. So I closed my eyes, like children do, the idea being, I can’t see you, so you can’t see me.

After some rather violent kissing Jed slid inside me and he was sweating ferociously and I tried to enjoy fucking him, but I was conscious of the others in the room, even though they were all otherwise occupied.

“Can I fuck your ass?”

“Uh huh.” Now I was a veteran! I knew that this was what Jed really liked.

This time, despite the application of much BabeLube, I was a bit tight, mostly ’cause I just couldn’t entirely relax, but again, it wasn’t painful. Of course, “it wasn’t painful” is not an overwhelmingly positive review. But I was too busy concentrating on not noticing the others, and couldn’t enjoy Jed’s grunts as he thrust at me with his long cock. Damn!

After he came I stroked his hair as he lay with his head on my chest, breathing heavily. I wanted to say, “Stay,” to hide me here beneath him until the room had cleared out. But I didn’t, because I didn’t want to have to ask him and I resented that I would have to ask him and anyway I knew he wouldn’t. He would want to be on Jefferson’s terrace, smoking cigarettes and flirting. When Jed excused himself I got dressed quickly, leaving the foursome on the futon and the group in the middle of the room, feeling worked up from all the fucking without orgasm.

I needed a break and when I went back to the living room I halted by the stereo: “Jefferson, are we listening to the Buzzcocks’s Singles Going Steady?”

“Why, yes we are!” Jefferson smiled.

Jacob, sitting on the sofa with some others, grinned at me. I had known that would get his attention. Though The Buzzcocks don’t really strike me as orgy music.

I slumped onto the couch next to Jacob and helped myself to a Double Stuf Oreo. “Hey!” I said. “How’s it going with that girl?”

“Ah,” he grimaced. “We’re just friends.”

This is an interesting story: at the last orgy Jacob told me he had just met a girl. They’d eyed one another at the supermarket near his apartment and then he’d nearly run into her on the street a few minutes later but for some reason had been unable to make contact. So he went home and posted an ad on Craig’s List’s Missed Connections! And, as he had told me, not 15 minutes later she had responded, and they had been on several dates and had not yet slept together and she was hotter than anyone here at the orgy now (I’m quoting).

But apparently it had come to naught, because, as Jacob explained, “I just don’t have the time to get involved with someone I’m not comfortable with.”

This struck me as sad – he’d been so enthusiastic. I expressed my sympathies and, after I’d eaten a suitable number of Oreos, got up to check out the action. “Don’t be a stranger,” Jacob urged.

I drifted back down the hall to Jefferson’s bedroom. The room was packed. And I was astonished and turned on to find Alex, in his underwear, wrapped around Mmmark in a hot clinch.

Ho boy. I swallowed. As usual, Mmmark seemed to be enjoying himself immensely. Alex’s face was hidden from view, but he, too, appeared pretty satisfied with this turn of events. Everyone else was likewise engaged. I slunk back against the wall for a minute, watching the couples writhe in the dark in happy abandon.

Part of me wanted to be in on the action, giggling and slurping and burying my mouth against someone’s skin. But I was also feeling just unwilling to be so exposed. Which is not the kind of attitude that serves one well at an orgy. OK. It’s time for me to go, I determined. I went to the bathroom and decided to make my goodbyes to Jefferson, and to Alex, whom I didn’t want to abandon. I found him in the back bedroom, sitting on Lillie’s bed. He was alone.

“Hey! You and Mmmark!” I said by way of greeting.

Alex nodded fervently.

“That was hot!”

Alex nodded fervently, again. I felt like I’d sent my protege out into the sex world for the first time, and he’d scored big. “Did you…?” What I wanted to know was had they done more than kissing? What had I missed?

Finally I abandoned all delicacy and, taking a seat next to him I whispered: “Did you go down on him?”

Once more, Alex gave me a nod. I high-fived him. “Well done! Doesn’t Mmmark have a nice dick?” Another nod from Alex while we both considered Mmmark’s anatomy. When I’d recovered I remembered my point: “Listen, I think I’m going to go.”

“OK.” Alex has the habit of looking as if he’s paying close attention when you talk to him, as if what you have to say is really important. I like that.

We hugged, and I sloped out of the room, only to run right into Jed. “Oh, hey. I’m about to take off.”

“What? You’re leaving?” I was gratified to see he appeared to be disappointed.

“Yeah, it’s late…”

“Oh,” He leaned down to me: “I was hoping you’d fuck me…”

Aha, the old ‘I was hoping you’d fuck me’ gambit! “Well, I… Oh, what the hell. Sure.”

So we tripped back into the back room, where we’d fucked earlier and where I’d last seen Alex perched on Lillie’s single bed. It was empty now. “I’ll go wash my hands,” I offered.

“People usually do that afterwards.”

“Well, I’ve got Oreo crumbs on me.” Not so sexy, Oreo crumbs.

When I returned Jed had stretched out on the bed. He was naked and the short, wide dildo I’d first encountered at his place a few weeks ago was beside him. I perched next to him, and then leaned over. We kissed. “Take off your shirt,” Jed said. I obeyed, keeping my eyes on him.

The room was empty but for the two of us, and I was relieved. As usual, I waited for Jed’s instructions. I like taking orders from him. Ahem.

He gestured to the bottle of lube, and I slid some all over my fingers. “Put a finger inside me,” Jed said after a minute.

I complied. I liked the slick, soft feeling of his innermost skin against my fingertips. Jed sighed, and I half smiled at his expression. Nothing else seems to get Jed as worked up as this. And even though I like it when he’s in control (over me), I like it when he’s out of control, too.

“Put another finger in,” Jed breathed. I fit my middle finger inside him, along with my index. He opened right up with no resistance at all. I liked that; how easily his body responded, how eager he was. I bent lower over him, stroking his ass with my skin.

“Put another one in,” he muttered, so I slipped my ring finger in this time. I went in slowly, so as to not stretch or hurt him, but it didn’t matter: he was wide open. His body was begging for it, just as women are supposed to be begging for it in the fantasy of fraternity brother speak. My breathing was getting a little shallow.

“More,” said Jed, so I fit my pinkie inside him, too. Sliding my hand in and out, I gazed at my fingers, astonished at what I was doing, and at the fact that the puckered dot of Jed’s anus could open up to fit all my fingers. Christ. I swallowed, and shifted a bit on the bed. I was getting wet.

“Put your whole hand in,” he urged. I looked at my wet hand doubtfully, but, after a moment, I slid my hand underneath him again and slowly inched my entire fist up his ass.

Holy smokes!

“Ahhhh!” groaned Jed.

My whole hand! I was fisting him! This was anal fisting! “Jesus Christ,” I gasped. “I’ve got my entire hand inside you.”

“Your hands are … really … tiny,” Jed breathed as he strained against me, arching and bucking. “Now the dildo.” I had almost forgotten about that in all the excitement. I slowly tugged my hand out, gazing at my sloppy wet fingers for a minute in wonder. It had been inside someone’s ass! But onwards: I squirted lube over Jed’s dildo, and then carefully turned it to face up, like he’d directed me the other week. As he squirmed on the bed, I fitted the dildo right inside him.

“Aaahh,” he said again. I crouched low over Jed’s torso, pushing the dildo up his ass, swinging my hand. “Oh, Lily…”

“Oh,” I murmured. “Oh, Jed, you’re doing great.” I slid the dildo back and forth, pushing it up Jed’s ass while he grunted. “You’re taking it like a champ,” I crooned. I have always, always wanted a chance to say this; to me it just sounds incredibly dirty and sexy. “Oh, you’re taking it really well, baby.” I slung my hips back and forth as I swung the dildo up his ass, slipping it out just a bit to hear him moan. Jed tugged on his dick. “Oh, Lily,” he said. “Fuck me, Lily. Fuck me.”

How I loved hearing him say my name. I bent lower, pushing my breasts towards him and rubbing the dildo more fiercely. “Oh, you’re doing so well,” I murmured. “That’s real nice.”

“Lily. Oh, Lily!” I watched smugly as with a shudder Jed came, a stream of semen spurting out onto his stomach. For a moment he lay still, his chest heaving.

Then I stood up and went into the bathroom, where I scrubbed my hands with Jefferson’s Vanilla Bean Noel hand soap from Bath & Body Works. When I got back to the bedroom, Jed was gone.

I pulled my shirt on, and back out in the hall I looked at my hands: I just had unprotected sex, didn’t I? Unprotected hand sex. Well, fisting. Ah: there was Jed.

“Heeeey,” he said, looking totally unconcerned, as usual.

I glanced down at my hands. “I should have worn gloves for that, right?” I don’t know why I was even asking, only he’d had experience with fisting (anal fisting! Wow) and I hadn’t.

Jed looked at me: “Give me your hands.” I placed my paws in his, and he held them up to the light.

“You’re fine,” he said after a minute. “You don’t have any scratches or anything, besides, I’m totally clean.”

I think he mean that he was free of disease; I already knew he was entirely clean, ass-wise. As Wendy had once asked me, “Do you think he spends all that time in the bathroom using an enema? That boy is immaculate.” (My guess: yes).

“OK,” I said, looking at my pink little hands, now smelling faintly of soap. “But if we do this again, we’re using gloves.”

And I trooped back to the living room, too tired to be worried about my bout of Unprotected Hand Sex. Alex had disappeared, as had Jefferson, and I really wanted to get moving before Jed suggested anything else I was likely to agree to. Though I’d fulfilled my directive to live somewhat dangerously and I felt smug, the apartment was hot and I was tired and hadn’t come and I was going home.

Another Virginity Gone! Or, Mermaids and The Theory of Jed

I got a text from Jefferson: “Want to see the mermaids?”

I’d forgotten: it was the day of the Mermaid Parade at Coney Island. I had never been. In fact, I don’t think I had been to Coney Island since I was three years old. Since I had between planning to spend the day stalking Jeremy I deemed this to be a healthier option. I said sure.

I got to Coney Island late, but Jefferson and company were later. I wandered for a bit, eating a lemon ice, then stationed myself outside of the Surf Ave. exit of the subway station, where people were streaming out.

It was hot and I hadn’t brought any sunscreen. I was moving back into the shade, right by the exit, when I saw someone: Jed.

What were the odds? It was so improbable and yet as I’d been thinking about him, I wasn’t as surprised as I ought to have been, statistically speaking. I started towards him: this was too good an opportunity to miss. Jed was talking to someone, a girl. For a second, I veered away, uncertain. Then I thought: Don’t be ridiculous. So I went up to him and tapped his arm.

A grin spread across his face: “What are you doing here?” I gave him an awkward kiss. He wore a camera around his neck and was carrying a silver board, I guess for lighting.

“Jefferson invited me … didn’t you…?”

We stared at one another for a moment.

Then he said, “I’m actually supposed to be meeting some friends but I missed them…”

I squinted up at him; he was a good head taller than me. Would he hang out with us, then? “Can you see?” Jed asked, gesturing at the mermaids.

I shook my head.

“Get on my back.”

I clambered up onto him and rode piggyback, feeling a little weird. After another phone we finally met up with Jefferson and the others: “Look who I found!” I glinted triumphantly at Jefferson.

I had recently proposed my theory of Jed to Jefferson. The previous week, I had lamented my inability to get quality time with Jed, and Jefferson had, sensibly, suggested that I go all out and actually contact Jed myself!

So throwing caution to the wind, I had sent Jed a brief email. It read: “Jefferson says that in order to get some time alone with you I should be blunt. I should say (his exact words) ‘Get me a drink and fuck me good.’”

Then I went on to say that while I felt this was a little forward, my sentiments were the same and, in fact, a drink wouldn’t be necessary – did he want to get together?

Jed never responded, which could be chalked up to his total flakiness, but also endorses my theory that Jed is interested in women who don’t approach him. I felt that Jefferson’s instincts had led me wrong and that I had made a tactical error by pursuing Jed. Hmmph. So now I was resolved not to approach Jed, which had gone out the window as soon as I saw him.

But here he was, flitting around with his camera and just being there in the corner of my awareness, all hot and no doubt conscious of the effect he was having on me.

Jefferson was accompanied by Callie, Jake, Cody, Viviane and a tall redhead whose name I didn’t know. He was wearing a blue tee shirt emblazoned with the words DADDY LIKES in raised felt letters, sort of old school looking. “I like your shirt,” I said, tapping him on the chest. Jefferson smirked.

Wendy caught up to us along the parade route – I’d thought she was with Jefferson and hadn’t grabbed her when Jed and I found Jefferson. So we all busied ourselves getting cups and digging Double stuff Oreos out of plastic bags. Cody was wearing a short sleeve shirt and I saw long thin weals along her left arm. That girl. When I first met her, in February, her naked torso was scratched with scars, which I had thought were evidence of a sexual masochism. But Cody’s self inflicted scars designate a more personal and less exuberant message. I hadn’t recognized them for what they were because I’d never seen the results of taking glass to the skin in an effort to overcome emotional pain with physical mutilation. Seeing her pale arms all scraped up made me want to shake her. She smiled at Jake and stood leaning into Jefferson and I thought, “You’re such a pretty girl. You don’t need all that makeup.” Her face was covered in foundation, and I’d like to see her bangs thinned out a bit, too. She’s so pretty, and they hide her face.

**

“Do you want to see?” Jefferson motioned me up to the front, and introduced me to the redhead, a.k.a. Meg, teacher and slut. I stationed myself right by the barrier, where I could see mermaids in all their weird glory: the Seapranos, the guys dressed as Vikings selling “Mermaid meat,” synchronized swimmers performing their routines on the ground. I hadn’t realized that these costumes were more than just mermaid outfits. I stared, open-mouthed as Jefferson took photos of the “Lady Marmalade” sex mermaids.

Jed strayed into the parade itself to take photos and when the parade ended he had disappeared. Wendy told me that he was planning to meet up with us later. Huh. I figured we had seen the last of him. So much for my plans for bedding him.

We all trekked to the beach, finding an empty spot far to the left of the Cyclone. There we settled ourselves with plastic plates full of Wendy’s macaroni salad and strawberries, drinking bottled water and red wine and gins and tonics from a big thermos.

We sat and gossiped and some adventurous folk even dipped their toes in the water. At 7:00 my phone rang: it was Jed. “Where are you?” he asked.

“We’re to the left of the Astroland sign,” I said helplessly. He said he’d find us but had to call back as my directions were so vague. I stood up. “I’ll come meet you,” I announced.

“Do you see the kites?”

I studied the sky: “No!”

But eventually I spied a fluttering red ribbon, just over the water. “Oh, right!”

“Meet me by the kite flyers.”

The kites bobbed above the water, and there I made a right and followed the strings, like that guy looking for Ariadne in the labyrinth, only without the nobility of purpose. At last I spied Jed, concentrating on the kite string he was tugging. He was standing next to two girls, both of whom appeared pretty impressed by their luck.

I greeted them all, and one of the women offered me her spool. I’d never flown a kite, and gingerly took the spool in my hand, and gave the thread a few tugs.

“You don’t have to raise you arms like that,” one of the girls counseled. “Just gently move your wrist.” She was, I noticed, wearing a black stretch bandage around her wrist. God, had kite flying given her carpal tunnel syndrome? Yikes. I adjusted my movements. Next to me, Jed swung his arm over his head wildly, enjoying himself, I would guess.

But the others were waiting for us. After a few minutes I returned the kite to the girl and Jed and I stumbled over the sand back towards the others. My sense of direction is not the best.

I gestured to the camera around his neck: “Did you get lots of good shots?”

“Yeah, great. Listen, do you want to come over later?”

Score! “Sure,” I said.

“Do you want to go on the roller coaster, maybe?”

I glanced at the Cyclone: “OK. I’ve never been on a roller coaster, you know.”

“What, really?”

“Yeah. Except for a kiddie one. But, you know, this is my year of living somewhat dangerously, so I should take the plunge.”

“Lily,” there was a laugh in his voice: “Am I just part of your experiment?”

I clutched his arm: “Oh, Jed,” I vamped, “You are so much more than that.”

**

When we reached the others everyone was starting to clear up. I helped pack up and then we made our goodbyes and headed towards the Cyclone.

At the line for the roller coaster, Jed went off to get something to eat. He came back carrying a corn dog, and offered it to me.

“I’ve never eaten a corn dog,” I offered, taking a bite. It was salty and boiled rather than grilled, and the cornmeal (?) was sweet and thick.

“Really? Well, this isn’t the best representation,” Jed allowed.

I took one more bite and gave it back to him. “I’m nervous about going on the Cyclone,” I said. Absolutely true. I had realized what I’d let myself in for: a ride on an elderly wooden roller coaster. “You’d better finish that.”

Jed wanted to sit in the front car but I, terrified, convinced him that it was enough for me to ride on the roller coaster, I needn’t have a heart attack as well. We checked our things and settled into the third car, locking ourselves into the seats. Jed put his arm around me and clamped his arm onto my hand. “Just hold on,” he advised. No worries there: my arm was glued to the metal rung.

We started with a slow rise, and it was beautiful, sunset over Coney Island. The sky was streaked pink and the lights from other rides were winking along the boardwalk. “Whoooo!” Jed screamed in happy anticipation. Then the car jerked and swerved, and we went over, swooping sharply down along the tracks. “Aaaaahhhh!” I, and everyone else, shrieked. “Keep your eyes open,” Jed counseled. Too late: I had shut my eyes just before we’d swung down, and I didn’t dare open them: “Ahhhhhhh!!” I screamed. With each movement I was lifted out of my seat a bit, and I was terrified that somehow I would be thrown from the car and hurtled to a gory death below. A girl flew off a roller coaster in the Midwest a few years ago; it’s happened.

We swooped up and down, and I dared open my eyes during our slow climb, but otherwise contented myself with gripping the armrest and shrieking. But it was over very soon, and we shambled to a halt under the grid of the coaster. My heart was pounding, and my limbs were weak with relief as I climbed out of the car. “I have to tell you,” I admitted, “I kept my eyes shut for most of that.”

Jed looked disappointed.

Safely on the ground he lit a cigarette. “Can I have a drag? I just rode a roller coaster, so I think I’m entitled.” I clutched his arm. “You know,” I said, “In my first ad…”

“What ad?”

“My Craig’s List ad. The one I published a year ago. Well, on it I said I wanted to do some of the things I’d never done, like have casual sex, ride a roller coaster, and eat a habanero pepper. Now I’ve done two of those things!”

“Let’s get you a jalapeno!” He tugged my arm. Luckily we did not find one, but instead threw softballs towards a basket in the hopes of winning some stuffed animals, with poor results, and shot up bad guys at an arcade. Finally I bought us both bottles of beer and we agreed to split a cab back to his place. We stood on the corner outside Nathan’s Famous. Jed, still clutching his silver board, was being jostled. He drew me aside and we stood in the dark, the people pushing past us, drunk and merry.

We kissed, and then he placed his hand where my neck and jaw meet, and that seemed to me a kind of possession, and I liked it. I swallowed, and trailed my fingers along the gap between his top and his jeans. “I like that,” he said.

We stood there for a moment. “Come on, let’s get a cab,” I said finally.

Eventually we found ourselves in the backseat of a Lincoln heading back towards his neighborhood, trading stories about our youth. I could picture him as a cocky adolescent, stalking around in his cowboy boots, declaiming on philosophy while eager girls hung on his every word. He had not lost the habit of declaiming, for he managed to turn every anecdote or sentence into a moral lesson or to explain how it had affected him. He appeared interested in my stories, but not as interested as he was in his own. Which I suppose is the case with all of us, only some of us know how to hide this disinterest better, perhaps.

**

Back at his place we dumped our stuff on the couch. His roommate was nowhere to be seen. Then Jed took my hand and I followed him into his room.

I took off all but my underwear – hell, I hadn’t shaved my legs, and I was wearing really old bikini underpants. That’ll learn me. I climbed up the ladder, and sat on his loft bed, the roof low over my head. After a minute Jed joined me.

We looked at one another. “Turn over,” he said, “I want to hit you.”

With a sigh I obeyed: “Start slow,” I warned him.

So he did, just how I like it – the first tentative brush, then the light slap and then the thwack. I clenched my ass against the onslaught. I was shaking. Wow. Wow. Wow. I heard myself whimper.

He entered me from behind. Although I find being on all fours rather exhausting and hard on the knees, I like lying on my stomach and being fucked. I don’t come that way, at least I never have, but it really feels good. “Are you OK?” Jed asked as he pumped away.

“Uh huh. You?” I am nothing if not polite. I turned my head to face him, looming over my shoulder.

Jed smiled: “Unless you’re penetrating me, you can assume I’m OK.”

Oh, right.

Soon I climbed on top. of him and started swinging back and forth, not taking my eyes off him. As expected, he slid a finger into my ass.

Jed’s hair spread out against the pillow. God, he was sexy. I thrust my hips forward and rode him back and forth. “I have been thinking about you all week,” I breathed. True: he turns me on so much, I’d been fantasizing about fucking him, off an on since I’d last seen him.

Jed didn’t say anything. Was this the wrong thing to say? Oh well. I came.

Afterwards we switched positions, with Jed on top of me. “Can I fuck your ass?”

He had asked me that before, and I’d said OK, but in the end he hadn’t done it. Later, I’d asked him why, and he said he could see it wasn’t that into it. He was right, I wasn’t, and I wouldn’t pretend otherwise.

“I had two fingers in there,” Jed went on. Meaning he thought it wouldn’t be painful.

“OK,” I said. He had the BabeLube and was prepared to use it, I knew, and would go as slow as I needed. I didn’t like the idea that it might be painful, but what the hell: Live Somewhat Dangerously.

So. He slicked up his dick and slid his finger up in my ass again, and then another. And then, after a bit more lube and fingering, he put his cock in my ass and slid his body on top of mine.

Hmm. I lay there, breathless, as Jed pushed himself inside me. I was astonished to discover that it did not hurt. Hallelujah.

“OK?” panted Jed. I nodded.

It felt strange, I was being fucked – I felt like I was being fucked—but at the same time there was this empty space in my cunt where cock usually fills me up.

“You like getting your ass pounded?” Jed muttered.

“Uh huh,” I said, in wonder. I kind of did.

“You like being destroyed?” He thrust at me.

I exhaled loudly: “Uhh…” then he turned me over and slipped back inside my cunt before he came. Ahh.

Well. So. I’d been butt fucked. Another virginity gone. And it hadn’t even hurt. I felt perfectly fine, not at all raw or sore. I stared at the ceiling, considering this. Then Jed and I clambered down his ladder and got dressed. At the door of his room we faced one another, smiling. “I dig you,” I said, looping a finger through his waistband.

We settled on the couch in his living room. After a moment Jed turned to me and said, “Lily, I have to talk to you about something; it’s really important.”

I drew back and raised my brows in mock alarm. “OK.” I looked up at him.

“No, really,” Jed nodded emphatically: “I’m serious.” I nodded again. “I want you to know that I really like you, but I don’t see myself falling in love with you. I just don’t see it.” He shook his lovely golden head and waved his hand to indicate no: “I don’t see it at all,” he added, in case I had missed what he was saying.

I stared at him, openmouthed.

“I mean, I just want to make sure everything’s clear. I just didn’t want you to think … I know that we’ve hung out together a few times…”

Like, what, when we went to the movies? Huh! Had I been auditioning for the role of girlfriend without being realizing it?

Here’s what I was thinking:

1. You twit! Of course you’re not going to fall in love with me, nor I with you. I am 11 years older than you.

2. What, do you think I’m falling for you? You conceited little… You’re not all that! I lust after you, but I should hope that at my advanced age I know the difference between chemically induced infatuation and romantic longing.

3. Huh! What, I’m not good enough for you to fall in love with? I’m hot! I’m smart! I’m kind! I listen to you! How dare you not want to fall in love with me!

4. Do I seem needy? Oh, please, not that.

5. Oh, grow up, Lily. You’re being a baby.

6. Am not.

7. Are too.

But I forbore to say any of these things. Because, as I’ve noted, I am 11 years older than Jed and even if he is tactless, I am not.

“Uh,” I said at last, smiling faintly: “I … don’t expect that from you…” I shook my head.

“Really?” Jed looked relieved. “I met this girl, and I don’t know her as well as I know you, but…”

But I didn’t have time for this: “Do I seem nee—”

“No, no,” Jed promised. “I don’t think you’re needy, or clingy, or anything. I want everything with us to stay exactly as it is now. I like talking to you, and I like listening to you…”

At least I wasn’t needy. And then I wondered if he’d deliberately waited until after we’d had anal sex to inform me. I mean, my vanity was wounded more than anything else, but if Jed had really thought I was falling for him, surely he had been selfish…

And Jed went on about this girl he was interested in, a Danish woman he had met briefly and “spent a few hours fucking,” as he put it. It occurred to me, and not for the first time, that Jed likes girls who aren’t really available. I watched him covertly (at this point I was mortified to think he thought I was falling for him, and didn’t want to stare), and I felt kind of sad for him. I don’t know why, exactly. So we sat on the sofa and Jed checked his email while I tried to decide how I felt about this conversation. There was a party going on at some warehouse and Jed wanted to go, but first we were going to stop at a different party on his roof.

“Hmmm,” I said. “Do I smell like sex? Maybe I should take a shower.”

“You smell like fresh girl,” he said. Which was nice.

So we went to the roof, but it was empty so we headed out onto the street. Jed had a yelled conversation with a guy looking out the window of the building opposite. I could not believe how much I was reminded of college, despite the urban setting. Then we headed over to the party.

It was held in an old factory about a ten minute walk from Jed’s apartment. We got our hands stamped and Jed bought a burger with onion jam and I had a gin and tonic. We sat at a picnic table and I tried to ignore the fact that I was older than everyone else here. And the fact that, thanks to our illuminating and ego-bruising conversation, I no longer felt comfortable with Jed.

Soon we got up and started to dance. I talked to some girls, and Jed disappeared. And even though we’d had our conversation and I had no intention of falling in love with Jed anyway, I still had my eye out for him and wondered if he found this or that girl attractive.

After about a half an hour of this Jed reappeared. We danced together for a bit, but by now it was pretty late and I was tired.

I said as much to Jed. “I’m torn,” said Jed. “I mean, it’s not even about other girls. I just want to dance. How about I walk you home and then I’ll come back?”

Oh, for fuck’s sake. I laughed: “OK.”

But first we climbed up the fire escape and checked out the rest of the party. There was a room where people were waiting their turn to play Centipede (Centipede! I mean it’s retro to the party guests who are in their 20’s but to me it’s an actual game I remember from arcade machines and on friends’ Ataris…) on a screen projected onto the wall. We wandered for a bit, then left.

Back at his place Jed disappeared into the bathroom while I slouched on the sofa. His room was so hot and dark, I wanted to relax here for a bit.

At last Jed came out. He walked over to me and, leaning over, said, “Remember how I fucked you earlier?”

I wasn’t likely to forget it.

He went on, “How would you feel about turning the tables on me, and you fucking my ass?”

Oho!

“OK,” I said. “Sure.”

“Really?” He shook his head. “You are something else.”

I went into the bedroom and after a minute I heard Air’s Masculin/Feminin start: this was kind of sexy. Then Jed appeared, carrying a messenger bag. He climbed up to the bed and took out a cloth-wrapped package. It was two dildos: one short and wide, the other long and thinner.

Jed lay on his back and I sat between his legs, examining the dildos; I’d never held a one before.

“OK,” I said, glancing up between Jed’s legs. “You’re going to have to direct me.”

He nodded. “Lube up,” he instructed and I, accompanied by the trusty BabeLube, obeyed, squirting the liquid all over my fingers. “Now put you finger inside me.”

I slid my hand beneath him, and between his butt cheeks; he yielded easily to me. OK, so far so good.

“Now take it out. Now put it in.”

I followed along.

“Now two fingers.” Jed was looking not quite at my face, but at somewhere behind me. I applied more lube, and slid two fingers inside him.

It felt tight and wet and strangely familiar, much like my cunt feels like when I’ve put a finger inside. I pushed my fingers inside his yielding, juicy flesh.

“Watch your nails...!”

“Sorry!”

“Take your fingers out. Now put them back in.”

This went on for a bit and then Jed said, “OK, take the shorter one—” he meant the dildo – “Put some lube on it, and, yeah, turn it so it’s facing up. Is it facing up?”

“Uh huh.” I held the dildo in my hand gingerly, with the head curving towards me. I hoped I was doing this right.

“OK. Slowly put it in.” I pressed my hand against the dildo, and it slid right up Jed’s ass. It fitted like a plug. I smiled.

“Now take it out,” Jed said. His voice took on a new urgency.

I pulled, and the dildo came out with a slight pop.

“Slowly, take it out slowly,” Jed advised, breathing steadily. “OK, now put it back in, and out. Put it in. Take it out.”

I obeyed, my hand thrusting and tugging as I watched Jed’s expression. He took a bottle of poppers and swiped it under his nose – hey, why hadn’t he offered me any? – while I concentrated on fucking him.

“Now the other one,” Jed breathed. I rubbed lube all over the second, longer dildo, and making sure it was facing upward, slowly slid it up Jed’s ass.

“Yeah,” said Jed, as he tugged on his cock. “Oh, yeah. Take it out. Now put it in.” I was getting wet, seeing how aroused he was. “Oh Lily, yeah, fuck me,” he said as I bent over him, sweating, determined to fuck him good and proper. “Fuck me, Lily!”

He’d never said my name before during sex; I liked it. I squirmed a little, my panties were wet.

“Oh, oh, yeah! Yeah!” And then with a sigh Jed slumped, his hand still wrapped around his dick. I held the dildo in place as he came, semen spurting onto his stomach. “Ahhh,” Jed sighed.

Well.

We looked at one another.

“That was hot,” said Jed.

I nodded. My knickers were still damp. “I’m just going to wash my hands,” I said. I climbed down the ladder again and in the bathroom carefully scrubbed my hands, all the way up the forearm, hands dependent, like I’d been taught when I volunteered at a hospital. I looked at myself in the mirror. My hair was frizzy with heat and waved out everywhere. I had just been fucked in the ass, and had fucked someone else’s ass. I looked for evidence to this effect in my face; I looked the same as ever, if slightly overheated. I looked around, at the bathroom of the 23 year old boy I was fucking, and I felt a long way from home.

When I went back to the bedroom Jed was dressed in jeans and a striped t-shirt. He was going back to the party, and I was going to sleep. “I’ll be back in a couple of hours,” he informed me.

He gave me a kiss, and as I climbed back up to his loft I heard the front door slam shut.