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?”
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.
“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.
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.
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.