Jefferson Plays Matchmaker, With NC-17 Results

I
On my way to Tilda’s, I considered whether this was a second date, and, if so, did it count as sleeping with someone on the second date if said date took place at an orgy?

See, in order to get over Dean, I had to start dating. Ashley had told me that she’d grasped the nettle and told all her friends she was interested in being set up, so I thought I’d do the same. I asked Jefferson if he knew of anyone suitable. It did strike me as funny that I thought the self-described pervert who’d orchestrated the majority of my risqué activities since 2006 would know anyone “suitable,” but I trust Jefferson.

Jefferson came up with the goods fast. He emailed me, “I traded notes with your new boyfriend and he’s glad to hear I recommend you to one another. So let me tell you a little about him. Byron is a 30-something Brit with a good job. He’s a lovely, personable, entertaining fellow and he's one of my favorite drinking buddies of late (Cabernet). …. Here’s a pic. Cute, right?” He added that Byron would be at the party Tilda was hosting on Friday. As would I.

Byron and I corresponded and agreed to meet for a drink the day before the party. Then I approached Jefferson with a sensitive question: “Is he bald?” I asked. “I'm wondering, cause he’s wearing a hat in the photo. Also, how tall do you think he is? Just curious....” (for just curious read: I hope he’s tall).

Jefferson was quick to assure me that Byron did have a full head of hair. He went on, “And he’s taller than me — I guess six foot? I don’t meant to make him sound perfect, so let me come up with a flaw . . . oh, he cares too much.”

II
When I met Byron on the Thursday night, I was relieved to recognize him at once—he looked just like his photo (I have a hard time recognizing people. For instance in December I went to Marc’s office’s Christmas party and, according to Marc, I “totally blanked” Will. I hadn’t recognized him at all, and we’d been fairly familiar with one another not so long ago. On the other hand, I always remember people’s middle names.)

Byron and I sat at a table near the window, and I ordered a ginger ale. I’d felt mildly nauseated all day. I’d been afraid I was coming down with a stomach flu, but eventually I twigged—I was nervous. Duh.

Byron had sandy hair, blue eyes, and a large, broad nose. He was my age, and from the north of England. I liked his voice a lot; I think a Northern accent is sort of rounder than a Southern one. I sipped my ginger ale. We talked about our common friend, and his blog, and then Byron asked, “Do you have a blog?”

“Hnnnnnnnnugh,” I said. “Well, I do,” I admitted finally. “But I’d rather not give you the address.” Dean had always had access to my blog, and I’d (mostly) censored what I wrote about him because of it. I didn’t want to do that anymore. I wanted at least the possibility of normal dating, whereby one person’s most intimate (and hopefully amusingly written) thoughts and feelings are not available online. I never would have been able to say what I did about Sweetheart Daniel if he had known about my blog, for instance.

“That’s OK!” Byron said. He smiled. He had a wide, sweet smile, and I relaxed a little.

“Do you have a blog?” I asked. Yes, he did. “I won’t ask you for the address.”

“I think that’s kind of nice, actually, you not wanting me to see your blog.” He did? Well, OK.

I eventually had a few glasses of wine, and when we parted outside the restaurant we kissed. It was open-mouthed, with a hint of tongue, but not quite a full-on make-out session.

And now, less than 24 hours later, we would be meeting again, only this time we’d be at a party held expressly for the purpose of having sex.

III
At Tilda’s I was met by a man I took to be Tilda’s boyfriend, but who I later discovered was the servant boy for the night. It was his job to fetch us drinks and attend to our needs, as it were.

In her apartment I was greeted by Tilda, wearing a fifties-style dress (very cute), and Jefferson, resplendent in shiny black pants: “PVC,” he explained. “Where else does a respectable father of four get to wear such togs?”

It was early and there weren’t many people here. I saw Marla, who figuratively and literally sparkled (she was wearing lots of shiny things) with her new boyfriend. I met Miss Molly Ren. I was suddenly starving and scarfed a lot of cheese and crackers. While I was stuffing my face, Byron arrived.

We greeted one another and drifted off into a group of people standing near the refrigerator. I was introduced to Toby and Lisa. Lisa was a little taller than me and looked distinctly underwhelmed by this gathering, while Toby looked like he’d just smoked a lot of weed. I (stealthily) positioned myself near Byron. Once I switched from Diet Coke to alcohol, I felt a little bolder. A tall fellow all in white wandered in, and it took me a minute to realize it was Jed (his short hair still surprised me). He came to greet me and we hugged. “Do you want to go into the other room?” he asked, sotto voce, as I poured myself a glass of wine.

“I’m kind of showing Byron around,” I explained, euphemistically.

Then the lights dimmed, and people started undressing. I remembered how, when Jefferson hosted orgies, on Mmmark’s arrival he’d say, “Oh look, Mmmark’s here! He’s the catalyst for the orgy, because he’s so hot.” Then he would add, “Or because he’s late.” But Mmmark wasn’t here tonight. Byron and I were leaning against the refrigerator, and I wondered if he was ever going to kiss me. I looked at him from under my lashes (the flirtiest thing I consciously do), giving him my best come hither glance.

Byron noticed: “You have very expressive eyes,” he said.

Yeah, and they’re saying kiss me. But eventually he did, so I could stop being nervous and anticipatory and start being relaxed and anticipatory. By this time people were in various states of undress—I spied Jefferson in the other room, naked (natch). Byron and I made out, my back against the refrigerator. He slipped his hand beneath my shirt and, after several attempts, managed to unhook my bra. I liked his awkwardness. “Ah,” said Toby, who, I realized, had been standing nearby with several other observers, “At last. We were taking bets on when you would get that off.”

I folded my arms across my breasts. Partially because I was embarrassed, and partially because I felt that being modest at an orgy is my shtick, my way of differentiating myself. Not that it’s not real; I am uncomfortable flashing my tits at a roomful of people who I’ve just met. And so when Toby asked to see my breasts, I demurred. I wondered: Is this modesty or marketing?

Byron and I kissed for a while, and then we made our way to the next room, where Toby and Jed were whipping Lisa’s ass (literally). She was bent over, her face to the corner, naked but for striped boy shorts. “Now put your legs together,” Jed commanded in a pleasant, paternal voice. He raised the whip. I swallowed hard.

But very shortly thereafter Jed ambled over and I wound up on the sofa with both Byron and Jed. Why hadn’t I thought of that? It was if the three of us synchronized our watches or exchanged sonic Yeses. Because without really looking at one another, I kissed Jed, and my jeans came off (I had finally uncovered my breasts). Then Byron slid his mouth down my belly. He looked up at me briefly before dipping his tongue against my clit. I couldn’t help it: I moaned.

It was agreed that we could “stretch out” (or, you know, have a threesome) in the back room, so we trooped across the apartment and settled on a futon, with Byron on my right and Jed on my left. Jefferson was on the bed next to us, with someone’s bare limbs wrapped around his back. I was fizzy with drink and enjoying myself immensely, with Byron’s tongue gently probing my clit and labia. My hips swayed towards his mouth, while I sucked Jed’s dick enthusiastically. I was dimly aware that other people were in the room, but I concentrated on Jed, while he murmured all the dirty words I love to hear. He came all over my tits, and I lay there dazed as he stroked a cloth over my chest, cleaning me up. I curled up against Byron, peaceful as a cat.

When it was time to get up I realized that there were six other people in the room, of whom at least three had been watching us with some interest. I found myself back in naïf mode, and I blinked and said, “Christ.” I ran my hands through my sweat-stung hair. “Ah.”

Now it was late and, as I’d successfully hooked up, my mission was officially complete. I could go home and go to sleep. However, I wanted to go home with Byron, but I couldn’t bring myself to say, “So, um, I was wondering, um, if…” Luckily Byron just called a car and took my arm, and he and Jed and I got into a cab together! But that was only because Jed and Byron live near one another. The cab dropped Jed off first.

When we got to Byron’s he opened the front door, “Oh my God, it’s so messy,” he said, sounding sincerely mortified. It didn’t look messy to me, though admittedly I would hardly know if it was; my housekeeping is casual at best. We went into his bedroom.

Alone, I could concentrate on his body. I hadn’t seen much of him, since I’d been occupied with Jed during our recent futon engagement. Byron had a warm, soapy smell, long limbs, and a lovely splay of freckles across his shoulders and back. He was uncircumcised, like most European men. I lay down on the flannel sheets, and when he pulled out Trojan Magnums I rejoiced.

He felt good inside me though I was too tired to get on top or indeed do anything the least bit strenuous. Byron, on the other hand, seemed prepared to keep going for some time. After a while he pulled out, and stroked my arm and kissed my nipples. I listened to his lovely (he pronounced it luvflee) northern voice. Did I want a glass of water? Something to eat? Was it too warm?

Then he got inside me again and broke out in a sweat all over—even his scalp was damp as I clutched his head close when he came.

IV
In the morning we moved from the bed to the sofa, where I did climb on top to fuck him. I like this position very much—I have control, but there’s so much more upper body contact. I came quickly, my legs shaking furiously. I thought it was clear I had come, but Byron asked, “Are you cold?”

“No one’s cold like that!”

We went back to his bed where we fucked some more, then into his lavish bathroom where we soaked in the hot tub-sized tub. He leaned back and I slumped next to him, my hair curling damply from the hot water. I lay there placidly, as if I usually spent my Saturday mornings lounging in a stranger’s oversized bathtub. I recognized this feeling: It was identical to a carbohydrate coma, a very pleasant state.

Then we went to brunch and when he drove me home the conversation wandered around the subject of relationships. “And what are you looking for?” He asked as we neared my apartment building.

“Well,” I said. What I wanted was not really the kind of thing you’re supposed to talk about on the first (or second) date, even if that date did involve sex and brunch. But fuck it, I wasn’t ashamed: “I’m ready for a serious relationship,” I said. “I’m 35, and I want to be committed to someone. I’m monogamous by nature.” True, though there’s not much evidence of that in this blog. I thought, briefly, of Dean: “I’d like to get married, and I want to have children, too, though not for a few years. Three or four years,” I concluded. Awkwardly.

“That makes sense,” he said, mildly, and pulled onto my street. We kissed goodbye several times, smiling at one another like sex-drugged accomplices. Then I trudged up the stairs to my apartment, where I took off all my clothes and climbed into bed. The last 18 hours had been eventful, and I needed to get some rest.

Younger Men and Black Framed Glasses: My Weaknesses. Apparently.

Jefferson had set me up with a 25-year old he’d been fooling around with. He’d emailed me the link to a story featuring Aaron in Time Out New York. I read the article. “Has he been rehabilitated?” I asked Jefferson, then told him he could give Aaron my email address.

Aaron sent me an amusing email and his spelling was fine, so I was inclined to meet him, even though I hadn’t seen his photo. When Jefferson suggests something I generally do it — he’s my excuse to do kinda reckless things that often turn out surprisingly well. And, until I was waiting for him at the bar where we’d agreed to meet, I didn’t even feel nervous. Am I becoming blasé? I think the fact that he was 25 and clearly able to construct a joke reassured me.

The thing is, he lives in Dean’s neighborhood. The bar we met in was two blocks from Dean’s apartment. In fact, I’d had dinner here with Dean not too long ago (we meet for dinner. We make out. He tries to feel me up; I tell him to cut it out. You get the idea. More on this another time). My sense of place is very strong — one thing I never do in this blog is identify neighborhoods. I think I once indicated that Jeremy lived on the East Side, but that’s not even true. I feel like your NYC neighborhood is a very important clue to your identity. For instance, before I met Jefferson I guessed where he lived without much effort. I even narrowed down his former neighborhood with his ex and kids. Anyway, I was on Dean’s turf, a turf I’d been familiar with for most of my life, and one I thought was particularly suited to the life I wanted to live, and thought I might live, with Dean. That is: a settled, married life with a couple of kids and a co-op. I was half afraid I’d run into Dean, though we’d never been to this bar together.

Aaron was almost on time and just a little bit taller than I am. He wore jeans and a boiled wool blazer and the hipster style black-framed rectangular specs I find so irresistible. I thought Aaron was pretty cute, even without the specs.

And smart and nice. And, as it turned out, a native New Yorker (always a plus). I asked him where he went to high school, he told me, and, without thinking I said, “Oh, do you know Eric Martin?” Since my friend Polly’s brother went to the same high shool and is about his age.

Aaron frowned. “I think he was in my class. How do you know him?”

Oh God: “I used to baby sit him.”

We both sniggered, me a little self-consciously. Note to self: do not say the first thing that occurs to you. Polly’s brother was a bright, talkative kid. I saw him last year at Polly’s wedding. He’s married now, like almost everyone I seem to come across these days. He grew up nice.

We finished our drinks. “Would you like to come over?” He asked. Where was my sense of fear, of self-preservation? Nowhere to be found: “OK,” I said gamely. I was completely at ease in Aaron’s presence. We bought a bottle of wine and headed to his place. I’d walked past his building many times on my way from Dean’s place to the subway.

Aaron had a nice apartment — the building and neighborhood would have suggested he was an older, more financially established professional. His largish studio overlooked a park across the street. There were no shades on the windows. He put on some music and settled on the couch. There was a pile of Time Out New Yorks on the sofa. “Oh that one’s old,” Aaron said, a little self consciously. “I kept it cause I’m in it.”

I didn’t want to tell him I’d read all about the coming without warning and the mood music fiasco. “Really?” I said. “Wow.”

On the sofa we sat near each other, and I went so far as to slip off my shoes (mules anyway), but I wasn’t going to make the first move. My boldness apparently extends to going home with guys I’ve just met but no further. Taking the initiative on the first kiss? Never! Eventually Aaron leaned in and we sat there, making out. Nice.

It helped that it was a studio with a big bed in the center so it wasn’t an awkward trip to the bed. I excused myself to pee and when I came back his kiss had a mouthwash-y taste. He’d used Binaca! So cute. Also unnecessary. I hate the metallic alcohol tang.
He lay on top of me and as we kissed I peeled off most of my clothes; he followed. As his tongue slipped towards my nipple I lifted my head from the pillow: “I don’t sleep with guys on the first date.” I mean, I have, but in general I don’t. Not at the moment, anyway.

“That’s OK,” he said, and turned his head back to my body. His tongue slid rapidly down. I wriggled out of my underwear, as did he. Then he levered himself between my thighs and put his face close to my pussy, like he was inhaling me, which I guess he was. Then his tongue began to slowly circle my clit, starting with my outer lips and then moving to the fleshy plateau (I can’t write mons pubis in a sex blog) above. His tongue dripped inward. I swallowed, my pussy pulsing. Aaron looked up at me and grinned. When his tongue reached my clit I sighed aloud, straining my hips towards his soft mouth. I felt like I was sinking into the mattress.

While he ate me, he shook his head back and forth, pressing his face to either side of my cunt, like a dog shaking water from his coat. Like he couldn’t get enough. I stroked his hair.

This went on for a while. I thought he might feel compelled to make me come, which I knew was unlikely. “Hey,” I said at last. He looked up sleepily from my thighs. “Don’t feel obligated to keep going,” I said awkwardly. “I never come from oral sex.” Anyway, I wanted to go down on him.

“I like this,” Aaron said, his voice muffled. He went back to eating my pussy. Well, who was I to argue?

SIDEBAR
I think I’ve come from oral sex once. This is funny. In mid 2003, prior my career as a slut, I went on a date with this guy Marco. He was Brazilian. We met for coffee, and then agreed to dinner. I went to his apartment kind of wondering at myself – I was going to a strange man’s apartment! I don’t even like him that much! What was I doing?

Marco was staying in a small apartment with the sort of modular blond wood-and-fiberboard matching furniture you see in your better college dorms. We ate dinner, started to watch a movie on his laptop, then started fooling around on his extra long twin bed.

Anyway. He went down on me and his tongue was so light and fast. I have no idea what he did, maybe some secret Brazilian tongue trick, but I came, to my great surprise. Then I got him off and we tried to sleep in the narrow bed. When I left in the morning I knew I would never see him again, and I was relieved. But to this day whenever a guy goes down on me, I usually murmur “Um, faster… lighter…” at some point during the proceedings.

SIDEBAR ENDS

Eventually Aaron got on his back and I straddled him. “You could sit on my face,” he suggested. I’d never really thought about it but sit on my face definitely had a dirty, euphemistic quality that I really liked. I mean, got me hot. I pictured myself literally sitting on his face, grinding myself against his eager mouth. But wait: “I want to get you off,” I announced.

So it was my turn to slide my tongue down the landscape of his body, making pit stops to lick the mountain of his nipples, kiss the valley of his bellybutton. Then I scooted down between his legs and moved my tongue across the scoop between the veins in his inner thigh. I licked him.

He had a nice dick. I trailed my fingers up and down, then moved my mouth around the head. Aaron stretched closer. I did as I’ve been instructed by various guys: a firm hand at the base, tongue on the sensitive bit under the head, rapid up-and-down strokes with my hand and mouth. To no avail. He wasn’t hard. “Is there anything I can do?” I asked at last.

“Um,” said Aaron politely. “You could hold my dick a little tighter. You know, squeeze it.”

I obliged and his dick stiffened right away. I grinned and sucked on his cock some more, my mouth and hand pulling at his cock, now properly engorged. Very soon Aaron gasped, “I’m going to come,” (I guess that Time Out New York lesson had taken). Then his come spurted out at me while I leaned over him, enjoying his expression. Our eyes met, and I brushed my breasts against his cock, and stomach, then rubbed it on my tits. I licked a drop off his dick.

“Do you want me to lick that off you?” he asked.

Taken aback, I spoke without thinking: “Oh, that’s OK.” But I liked his eagerness, and the implicit salaciousness. Then we settled back against the pillows and made out some more. I turned onto my stomach and he lay against me, bucking slightly. He slid a finger inside me and he moved his hips back and forth so I could feel his dick against my thighs. His dick felt stiff, the skin silky. I felt my pussy start to pulse again, and I reflected that maybe having sex on the first date wasn’t such a bad idea.

But instead we stayed like that, me feeling hot and liquidy. Then we relaxed into not-fooling-around mode and Aaron got a bowl of chocolate ice cream, which I polished off quick. I got the impression he felt chocolate ice cream was the proper food to serve following sexual activity. But I was starving, so we ventured out to a café. We sat at a marble-topped table, and I ate all my granita and most of his chocolate cake. When we left he walked me to the corner, where I hailed a cab.

“I don’t have any more money,” Aaron said. He’d bought the drinks, the wine, and the desserts. I wouldn’t have taken cab fare from him, did he think I expected it? I’m 10 years older, perhaps I should’ve paid for him. Or not. “That’s OK,” I said, nonplussed. We kissed next to the taxi. I got in and as we pulled away I saw him cross the street, his figure illuminated by the streetlamps.

I leaned back against the leather seats of the cab. I was looking forward to fucking him.

Drinking and Dating: Dangerous Yet Fun!

I met Dean for drinks at a bar on the West Side. This was the culmination of the sudden blast from the past – getting an email from Tim (who then promptly disappeared) and then one from the man I was about to meet: Dean. He had contacted me last spring via the personals, only to bail on our date the day of, due to (he claimed) having met someone. Whether he’d met someone or just changed his mind it was clear he was not entirely truthful, since after he cancelled on me he was still online all the time. But alas.

So we arranged to meet at 5:00 pm, which I thought was a neutral non-date kind of time, and would allow me to be out of there by 7:30, 8:00 at the latest.

When I arrived, the bar was empty (one of the benefits of meeting someone at 5:00 pm on a Sunday evening), so when a tall man in jeans and sneakers stood up, I had no problem identifying him as my date.

“Hi,” we shook hands. “I’m Lily.”

“I’m Dean. Do you want to sit outside? They have a back yard…”

I trailed Dean the length of the bar and into the back yard. There we settled ourselves at a table and ordered: a Flirtini (me) and a glass of Pinot Grigio (him).

I studied his profile: he was really cute! He had a thin, angular face with high cheekbones and blue eyes. Unfortunately, he was wearing high-waisted jeans and sneakers, a look I abhor. If only he had worn low rise jeans and a t that wasn't tucked in! Alas. Also, there was something awkward about him, maybe it was his height? (he is very tall). I would have thought that someone so handsome would be more at ease, but there was an hesitancy and awkwardness about him.

We got to talking. To my surprise and delight, Dean is a native New Yorker. He actually knows someone I’ve known all my life. And he lived in a neighborhood I know well.

“Oh, hey,” I said, “My friend Jessie lives on your block, in the apartment building on the Southeast corner.”

“I live on the street itself, not on the corner.”

I know my New York City streets. I don’t know that there are any apartment buildings on that block. That could mean only one thing: “Do you live in a brownstone?” I asked.

“Uh huh,” he said, unaware of the effect his revelation was having on me.

Wow: a brownstone. I ordered another drink.

When my Flirtini came I offered him a sip, and when he reached for my drink his hand shook. Again, it seemed at odds with his relaxed slouch and easy conversation. “I’m not looking for a serious relationship,” he offered as we sipped our drinks in the late afternoon sun. I gazed up at the sky. “I just got out of a serious relationship and…”

I nodded. Was this his usual spiel to ward off potential girlfriends or was this a response to me? I couldn’t tell. Did I look like a person who wanted a boyfriend?

“What do you do?” I asked, not really anxious to talk about relationships.

“I’m a poker player.”

“No kidding!” I was pretty sure that on his personals profile his occupation had read “writer.”

He nodded.

“Wow.” I really didn’t know what to say to this. Probably “So, you’re a professional gambler, are you?” wouldn’t go over well, ditto “Oh, did you get caught up in that late 90’s Vince Vaughan – retro – Rat Pack trend? I thought it ended in 2002.” So I settled for, “How long have you been doing that?”

“Not very long.” And with this, Dean edged his chair closer to mine, and slid his hand on top of mine.

Oh! Startled, I took another gulp of my Flirtini. He was bold. Well, sort of: I noticed that his hand was still shaking. I looked up at him.

He leaned over and kissed me.

I mean, I wasn’t complaining, but I’d known him less than an hour.

“Was that too forward?” Dean asked.

Again, I wasn’t really sure what to say. I didn’t mind being assaulted by a cute guy, but we’d skipped the preliminaries, which I so enjoy. To wit: the hand brushing, the shy glances, the admitted embarrassment, all of which I find a prerequisite to an hour or so of drunken making out. I feel that clumsy foreplay adds a certain frisson to the proceedings.

“Well, um… I guess not,” I dithered. “I mean,” I added, anxious not to be rude, “It wasn’t unwelcome, but I barely know you. Did you get the idea that I’m easy?” I asked (I was a little squiffy at this point.) “Cause I am, you know, but…”

Dean laughed, and I looked at my lap and sniggered. Then he kissed me again. He smashed his lips against mine, holding my chin in his hand. What the hell: it was a Sunday afternoon in the summertime. I kissed him back.

“Let’s go to Central Park for a bit and then maybe catch a movie,” Dean suggested after we’d each had another drink and split a quesadilla.

“Well, I don’t know if I can make the movie…” this date was already going longer than I’d planned. Of course, I had nothing else to do but read the new Harry Potter, and I was trying to savor that one, anyway. So I found myself walking to Central Park with Dean. He took my hand. Oh, this was awkward: I came up to about his chest. I’d get a crick in my neck if I looked at him.

We traded memories of our respective New York pasts – oh, how I love meeting native New Yorkers, it makes the feeling of inborn superiority that much sweeter – and eventually ended up on a patch of green in the Sheep’s Meadow. I was feeling pretty drunk, so I sprawled on my back, as did Dean. Was this loose behavior, lying prone in public with a total stranger? Yes, I decided hazily, it sure was.

“I forget if you put ‘Don’t use drugs’ or ‘Prefer not to answer,’ on your personals profile,” Dean said.

“Um, well, I don’t remember,” I said. I had no idea. I don’t really use any recreational drugs (the poppers incident aside), but I didn’t want to eliminate cute boys who happened to smoke weed from my pool of potential boyfriends.

“Ahhh.”

“So, do you…” I mean, did he smoke weed or was he talking about something more exotic?

He was talking about weed. Marijuana had been invaluable to him, he informed me, especially in getting him to appreciate certain aspects of sex that otherwise he had been unable to enjoy.

I gaped at him. “Are you trying to tell me that you couldn’t go down on a woman before you started getting high?” This didn’t impress me. Is overcoming an aversion to oral sex so commendable? I feel men should enjoy going down on women. I enjoy giving head, after all.

“No, I mean...” Dean backtracked. “Before I started smoking, I couldn’t enjoy going down on a woman for itself … I mean, now…”

I snorted. “So now you can enjoy the experience?”

“Yeah.” Dean looked embarrassed. He’d only meant to let me know that sex with him meant lots of eager tongue action.

“Oh,” I sniggered again. “I don’t really get off on oral sex, anyway.”

After a moment Dean rolled on top of me. We lay sandwiched together on the grass. Is this totally inappropriate? I wondered, looking at the people around us. I must be pretty drunk. He kissed me, hard, and then pressed his index fingers along the line of my eyebrows.

“I’m submissive,” I said, apropos of nothing.

“Are you? I like that.”

“I thought you would.” Clearly, I had decided to sleep with this fellow. Well, that’s alcohol for you. Or attraction. Whatever.

A man carrying a plastic garbage bag was hawking beer. Dean hailed him. “Want to have a drink then we can see a movie?”

“Well… OK.”

“I’ve got mojitos!” offered the guy with the black plastic bag.

Mojitos it was. We watched in amazement as instead of presenting us with two bottles, the man proceeded to break out a flask, and then mixed two drinks in plastic cups.

It was getting late; the sun was fading in the July sky. “Come on,” said Dean, “Let’s see a movie.”

**

When we got out of the theatre it was dark at last. “Let’s get dinner,” said my date.

Drinking usually kills my appetite, but what the hell, it was a nice night, and we could sit outside and drink some more and flirt: “OK.”

We walked a few feet to a crowded restaurant and were seated at a table outside. “Put your foot in my lap,” said Dean. I obeyed, and he rubbed my ankle and the top of my foot. Drink made me voluble, and when Dean asked me if I was seeing anyone else, I gave him an edited resume.

“So how many men are you sleeping with?”

“Um…” I counted off: Jefferson, Jed, Jim. three. “No, wait, four.” And Alex. Christ, I must sound like a complete whore. “How many women are you seeing?”

“Well, two, but one of them I don’t see very often. The other one…” I sipped my white wine and nodded my encouragement. “I met her on Craig’s List.” Well, that’s how everyone meets, isn’t it? “And, it’s kind of a situation where I help her with her bills.”

“Oh,” I gulped some more wine. Oh my God! He pays a woman to have sex with him! Actually, I didn’t understand this. Dean was cute and polite and smart, surely he didn’t have to pay to get laid?

“Well,” I said slowly, aware that I was drunk and wanting to choose my words carefully: “I really appreciate you telling me that.”

“We get along well, I mean, I mean, I don’t think she’s faking anything…at one point I said to her, ‘You know I don’t feel that comfortable—“

“Well I’m sure she needs the money!” I said, scandalized. Did he object to paying her? I poured myself some more wine. “Look,” I said when I had fortified myself with yet more alcohol, “I really appreciate you being honest with me about this. But you’re involved with a sex worker. If you want to sleep with me, you’re having an HIV test.”

“Really, I think I’m the only one—”

I nodded vigorously. Maybe he was right. Perhaps I slept with more men than Dean’s part time girl. Maybe I was a worse bet. But. I was drunk and feeling forceful.

Just then our food arrived. For a few moments we ate our pasta in silence, while I digested all this information. This was certainly an informative date. And a long one: it was practically my bedtime.

I pushed my naked foot at Dean’s groin and smirked at him.

“God, you’re sexy,” he said. I looked at my lap, embarrassed and pleased. “And I might have to take you over my knee and spank you for telling me I have to get an AIDS test,” he whispered. “Not that I mind about that at all,” he added in an entirely different voice.

I loved that he had said that: that he had told me he was going to spank me and then in the same breath went on to reassure me that I could demand this of him. I beamed at him. I didn’t know that I wanted him to spank me until he’d said he was going to, but I did, I really did.

When we finished our dinner, Dean suggested we get another drink.

“But it’s late!” It was about midnight. “I have to go home!” He kept talking me into stuff, and I kept enjoying it. Was a taste of our future interactions? Hmmm.

“Listen, I will take you for one drink, and then I will put you in a cab and give you cab fare to get home.”

I chose the path of least resistance, and more cocktails: “OK then. Let’s get a drink.”

We proceeded to another bar where we drank and fooled around until the bar closed. But we were talking a blue streak and I found I had no interest in this date ending anytime soon. We ended up sitting on the stoop of a nearby brownstone, explaining ourselves in an earnest manner. “I don’t fuck around,” I slurred at one point, in between some heated making out. “I mean, I’m honest and I don’t play games.” I’m not sure why it was important for me to stress that. Oh yes, I know why: cause I’d just told him I had a sex blog and given him this address! D’oh!

But finally it was time for me to go. We stood up but when we began to descend the stairs, he or I tripped and we both went flying. I landed next to him on the pavement, having scraped my shoulder but otherwise unharmed. God, how embarrassing. Then I got a look at Dean: “Oh, my God! Are you OK?”

Blood was pouring down his face. Under the amber glow of the streetlamp, I could see that his face was cut in several places. “I’m fine,” he said.

“No, you’re not!” It looked really bad. “Do you have antiseptic, and bandages at your place? Are you sure you’re OK?”

At my insistence we trooped off to a drugstore, and then went back to his place, where I dabbed at his wounds with cotton balls soaked in Bactine. “Are you sure you’re OK? You might be concussed.”

“Really, I’m fine. Come on, let’s sit in the hammock.”

We were on Dean’s deck. He lived in a duplex, and his bedroom opened up onto a terrace. And he had access to the roof above, too. Talk about an embarrassment of riches.

There didn’t seem to be any point in putting up anymore resistance, especially as I didn’t want to, so I followed him up a steep ladder to the roof, where we carefully lowered ourselves into his hammock.

The night was mild and cloudy and when we weren’t kissing I stared at the sky. “Oh sweetie,” Dean whispered, “It’s going to be so good.”

"Mmm," I murmured, kissing the man I'd met nine hours previously. He had several fingers inside me at the time, and I was inclined to agree.

One Giant Step for Jim

I had a date with someone named Jim. He’d emailed me via the personals. He had an awful photo, making him look like Mr. Spock had an affair with one of his fans. But his email was articulate and correctly spelled, so why not, I figured. Plus, Jim was 25, so there was no way of me being intimidated.

We met at The Dove, which Citysearch promised was quiet and romantic. It was heaving. I snagged a table near the window. A bit after 8:00 p.m. I noticed a man pacing on the sidewalk outside. I knew it was him, and when I went outside, our eyes met and we introduced ourselves.

Dear me. Jim was skinny and awkward, with acne and acne scars, and he was wearing chinos or something equally unattractive. And he ordered a Coke.

But since he looked so unprepossessing, I felt sorry for him, and worked hard at conversation. As it turns out, Jim is quite well read and, after he warmed up a bit, a decent conversationalist. So the effort was well rewarded, even though he still seemed uncomfortable. But I ordered another drink and so my increasing confidence made up for his lack.

We stayed about two hours. I found myself thinking along these lines: “He’s a nice lad,” and “Maybe with a better haircut…” and “I wouldn’t mind seeing him again…” hardly indicators of flaming chemistry, but still.

Jim decided to take the same train as me partway home. While we were waiting on the platform he took off his glasses. Suddenly I noticed that he was standing close to me, and looking at me, and despite the fact that he was a young whippersnapper of incredible dorkiness, I felt a bit of a frisson, as they say. And then he pointed out that he had two different colored eyes: one blue, one brown. I looked into his eyes. “Wow,” I said.

He was so much better looking without his glasses! It’s strange, because often I think men look better with glasses than without. But without his specs, Jim looked both stronger and more boyish; his smile seemed brighter; I don’t know.

The train came. We sat on a bench next to one another, our shoulders touching.

“You have really small hands!” He exclaimed, putting his palm to mine to compare. The hand comparison is almost always a prelude to lacing fingers and clutching palms, itself a prelude to the goodnight kiss. We laced fingers, and somewhere around 23rd Street, Jim moved his face towards mine and kissed me.

I had thought he’d need a bit more encouragement. But I wasn’t complaining, and I liked that after all my work at drawing him out, he was taking the lead. He was a nice kisser – firm lips and not too sloppy and, thank God, he smelled right. I breathed him in with relief.

We kissed without stopping. I mean, there was none of the breaks to press foreheads and smile, or to exchange the smaller, more delicate kisses. This was just high school making out. “Get a room!” a teenager shouted.

If we kept going he was going to miss his stop. And I thought, Why shouldn’t he come home with me? Why not? And when I calculated we had passed his stop we broke apart and I breathed, “You missed your stop.”

Then we started kissing again.

The train was running express, and soon enough it would be my stop. As it came up, I tugged his arm. “This is my stop,” I stood up. “I guess you’re coming home with me,” I smirked.

Jim didn’t object, but instead gazed at me moonily as we waited for the local. When we got off at my stop, he took my hand and clutched it as we walked to my place. He’s so young, I thought, and felt a little embarrassed, as if afraid someone I know might see us.

At my place I offered him something to drink, like an ordinary hostess, then led him to my bedroom. We lay on my bed, kissing, and I could see he had a nice, straining erection. We got naked pretty quickly – he had trouble with my bra -- and he lay on top of me, kissing me everywhere. It was obvious he had very little experience. He wasn’t slobbering all over me, as inexperienced men are supposed to do, but he seemed so thrilled, so eager, so amazed, that I ended up feeling a bit detached. He bent over my stomach: “You have… the most… perfect belly button,” he murmured, kissing my belly. Aw. Juvenile excitement has its compensations.

Jim had a nice sized dick; one of the bigger I’ve seen. I stroked it approvingly. I was on my back with my legs spread, and he was on top of me. He started to push his cock into me.

Was he kidding? “Hey,” I tried to make my voice sound gentle rather than panicked or outraged, “I don’t do anything without a condom.”

“Oh, right. Right,” said Jim.

We paused, and I lay back against the pillows. “Look,” I said. “Are you sure you…?” I started again: “I just think … You seem … vulnerable, and I don’t want to hurt you or anything.” Oh, well, might as well: “Can I ask you a few questions?”

Jim nodded.

By now I can recite them all from memory. “Have you ever injected any drugs?”

“No.”

“Have you had sex with a man?”

“No.”

So far so good. “How many women have you slept with in the past year?”

He circled his thumb and index finger: “Zero,” Jim said, scrunching up his face in embarrassment.

Not a surprise. “And how many women have you had sex with ever?” I was betting one, two tops.

He held up the thumb and index finger again: “Zero,” he blushed.

Oh, my God.

“Oh, my God,” I said genuinely shocked. A 25-year-old virgin. Here! “Really?”

He nodded.

Oh, Christ! “Are you sure you want to do this?” Which was a dumb question. He was a 25-year-old virgin. With an erection. In my bed. “It’s just that I’ve never had sex with a virgin before,” I explained worriedly. “I feel a certain responsibility. I want it to be good for you.” This would undoubtedly be something he would remember. Could I bear the onus of being responsible for an indelible memory? What if it sucked?

Well, at least Jim’s erection showed no sign of buckling under the strain. I leaned over and reached into by bedside table for the Trojans. I put it on him carefully, and lay on my back.

He pushed his way inside me. We looked at each other. “How’s that?” I asked.

“Good…”

I figured he would come right away, and wasn’t expecting much. To my surprise, there was no gasp and collapse, just the rigid certainty of his dick inside me. I had nothing to console him about yet; that was good.

What the hell. “Can I get on top?” I asked, my most common question to the men I fuck, I expect. I started to ride him, and though I didn’t come I was glad to note that Jim had stamina, and seemed determined to please.

We fucked for quite a while, and he didn’t come at all, which I diagnosed as the result of about 15 years’ worth of masturbation techniques polished to a high degree of specificity. So he pulled off the condom, and started yanking on his cock with some violence. I watched him, and tried my hand at it (literally).

“Harder,” he said. Then, “Ouch!”

“Sorry!” I grimaced. I tried, but could not find the particular rhythm or pressure he seemed to require, so eventually I gave up and watched him manipulate himself.

“Before I come I have to switch hands,” he explained, as he switched from his right hand to his left. “And, oh God, this is so embarrassing – I have to make out with my arm, too, when I’m getting ready to come.”

“What?” I tried not to laugh, but just could not refrain. This made me picture Jim as a scrawny, gawky thirteen year old, jerking off to soft core magazines in a furnished basement with his parents upstairs. Aw. I leaned over and kissed him as he tugged on his dick, looking away politely as he exchanged passionate kisses with his upper arm.

**

Afterwards I noticed something awful: “Jim,” I asked, “Have you been wearing socks this whole time?”

He nodded. “Take them off,” I insisted, and waved a finger at him: “Never, ever wear socks during sex. It is the most unsexy thing you can do.” I was getting into this woman of the world thing, thinking how I could use my influence for good, and make his future lovers grateful for my gentle training, etc. “And always use a condom,” I added conscientiously.

In the morning we had sex again. He fucked me vigorously. Neither of us came. At last I lay on my stomach and had him enter me from behind. “Do you like that?” I breathed.

The proper answer to that is “Oh, yeah, baby.” (Like I said, I like the soft-core porn murmurings.)

“I like it if you like it,” was the lukewarm response.

I shook my head and smiled despite myself. “That means you don’t like it,” I said into the pillow. “That’s not much of an endorsement.” I slipped off of his dick, and turned around.

“Oh, sorry, you’re right.”

Jim was annoyed that he hadn’t come, but seriously, I thought he had acquitted himself pretty well for a first timer: no premature ejaculation, no nerves-inspired loss of erection, much attention to me and my wants. I wasn’t really inclined to console him at this point. After all, I hadn’t come, either.

We lolled around for a bit. “You know," I said, "You have a big dick.”

“Really?” Jim said. “I do? I always thought it was just average.”

“No, it’s a good size,” I said. I had suspected he’d be surprised at this bit of news.

“Awesome,” he grinned. “You just made my day.”

“Jim,” I said, “I just went down on you. I deflowered you, and that made your day?”

“But the compliment will last a lifetime,” he said happily.

**

Eventually we repaired to a diner near the train station. I sat there, feeling progressively more uncomfortable, while Jim stared into space.

“Is something wrong?” Generally I do not ask men this question – it is really only one step away from “What are you thinking?” and really – well, my guess is, if the guy wants to tell me something, he will. But maybe I had a special obligation (a geas!) to Jim, since I’d deflowered him after a scant three hours’ acquaintance? I dunno.

“What? No…” Jim flashed what might have passed for a smile.

“You’re just looking a bit grim.”

“No,” he said. “I was just staring at you.”

**

Finally I walked him to the train station. We kissed and kissed. Then we stared at one another awkwardly and I made some comment about how I hoped it had been a good experience for him, and he made some comment about how it had been a wonderful experience. Then we kissed again, and he ran down the steps. I walked home, feeling like I’d just lit a roman candle, and now I had to wait for it to explode.

Mmm, Mmmark

On Monday night I had a date with Hot!Mark. I mean, Mmmark. After my classic exit line (“I enjoyed going down on you both!”) he’d sent me a nice email, asking if I wanted to meet for a drink. As the Brits say, "Ding dong!" Which is untranslateable, really, but you say it in a campy, theatrical voice and it means, "You lucky minx! What a hunk of man!"

We met near a bar on Sixth Avenue, and it was freezing. When he turned up, I was, again, taken aback by how good looking he was. I felt tongue tied, especially when Mmmark mentioned that he was going skiing next month. I’m not sure why his talking about sports made me feel so awkward. Possibly because I am so unathletic? In his wool sweater and red cheeks Mmmark looked really healthy and cool -- like someone who views sex as good exercise. In my quilted down coat I felt like a feeble urban wimp. Quite correctly, as a matter of fact.

We went to a nearly empty bar – it was early— and settled in with our glasses of Marker’s Marks (him) and Pinot Noirs (me). The music was almost entirely early ’80’s pop—obviously geared for old geezers such as myself: “Johnny Are you Queer?” came on, and this made us giggle, since it started just as we were talking about Jefferson and his parties.

I had assumed that Mmmark was older than I am, but when I discovered he was almost three years younger I felt a bit more relaxed. When I know that I’m older than someone, often the traits that seem intimidating become endearing instead. And Mmmark, instead of being this totally alien hot guy, was still hot, but more approachable. Not the stud I’d encountered in Jefferson’s blog, nor even the really hot stranger from an orgy, but instead a nice Midwestern guy in a wool sweater.

We talked and drank and drank and talked and I noticed he resembled not Chris O’Donnell, as I’d previously decided, but Patrick Dempsey. We agreed that it was only a matter of time before New York Sports Clubs starts offering sex fitness (“Participants must bring a towel …. No, it’s three thrusts and then a deep breath!”) and discussed the neighborhoods we’d lived in. Mmmark used to live very near Jeremy, which gave me a pang. He’s been to some of the same restaurants Jeremy and I ate at. It occurred to me that although I’d forgotten to bring my list of questions and that I was opposed to sleeping with someone I’d met at an orgy, I would nobly forgo these scruples if Mmmark was interested. Then Mmmark said he had to be home at 9:00 for 24. Dissed! Don’t you want to have sex with me? I thought, forlornly, as I emptied my second glass of wine. Then I went to the bathroom and lectured myself on the futility of assumptions. It did not cross my mind that perhaps Mmmark was likewise wary of having sex with someone he’d met at an orgy outside of said orgy. Though he did say I was the first person he’d ever had a date with from one of Jefferson’s parties. Flattery will get you everywhere, baby, I thought, and gave him a big smile.

But we ended up with our hands clasped, and my fingers stroked his palm casually. Though I didn’t feel casual, I mean, each time I touched his fingers I wondered if he liked it or what. But apparently he did, because eventually we started kissing and he asked if I wanted to come over to his place.

“I can’t stay long,” I warned, because in addition to feeling uncertain about the wisdom of sleeping with a man I’d met at an orgy—or perhaps, more importantly—I was wearing jeans and hadn’t brought a change of clothes for work in the morning.

“That’s OK,” said Mmmark. “We can just cuddle on the couch.” A man after my own heart. Obviously, he was skilled in appealing to scaredy-cat girls. He glanced at his watch: “It’s already after 9:00,” he said. “You made me lose track of time.” I smiled.

We took a cab back to his place and there we settled on the couch in front of the TV. Mmmark tried to explain some of the intricacies of 24’s plot to me, but I was more interested in the fact that both Chad Lowe and Peter McNichol were on the show as bad guys. Wimpy bad guys! This segued into an argument about Peter McNichol’s television credits. I have a distinct memory of Peter McNichol as a series regular very early in the run of Law and Order. Mmmark disabused me: “I have seen every episode of Law and Order,” he declared, “And Peter McNichol was never an Assistant D.A.” A Law and Order fan! Big points on the Geek-o-Meter! Hot. I launched myself at him.

We made out like kids: fully clothed, me lying on top of him on the sofa. He smelled delicious and it was just dreamy. By dreamy I mean thinking about it now, I feel literally sort of blurry and swoony. It was super nice and look at my vocabulary! Super nice! Lust and romantic good will have turned my brain to mush. I must say, it’s a pleasant feeling.

A Picture Tells a Thousand Words, Most of Them Wrong

The night following my jaw trauma revelation, I met Chris.

He’d emailed me via the personals, and his photo was very cute. From his vague profile, it looked as though he was in a relationship. When I asked him if this was the case, he said it was, and that he and his girlfriend had an open relationship.

I wrote back to say that if by an open relationship, he meant that his girlfriend was actively OK with him sleeping around, then that was fine with me. Then I recounted my story about Jon, who claimed to be in an open relationship but who, in fact, just slept around while his girlfriend tolerated it. Chris said that, yes, really, it was an open relationship, and his girlfriend saw other men, too. So we agreed to meet.

I don’t know why, but I wasn’t thinking there’d be much spark. And I was right! We were due to meet at a bar on Ninth Avenue, and it was heaving, which always annoys me. When we met I thought, You look nothing like your photo! He must have been at least 30 pounds heavier than he had appeared online! I thought the camera added ten pounds, but not in his case.

All the tables were taken, so we edged up to the bar, where Chris insisted on paying for my mojito, which came with a real stick of sugar cane, yum! He said that he insists on paying, he likes to be polite. Etc. After my discussion with Jeremy, I must say this was a nice respite.

We talked a lot, about our jobs and families and stuff like that. I had a second drink. He kept holding my eyes for a bit longer than necessary, so finally, to ease the tension, I said, “Are you going to kiss me?”

He broke into a grin and started to kiss me. That was a dumb move on my part, cause I’d been thinking that although Chris was perfectly pleasant and smart, I wasn’t interested. But there we were, making out.

There was a couple next to us at the bar, and the woman was pretty drunk. She started kissing the guy, and then I felt her arm snake through mine. She thought my arm was his! Giggling, I pointed this out to her. She was mortified.

“Oh my God, I’m so sorry,” she gasped.

“That’s totally OK,” I insisted. “It’s nice to have someone stroke your arm.” Well, it is.

But she bought us a round of drinks .. gah! I was feeling very drunk.

Eventually Chris and I left, and said we’d get together again. But I wasn’t sure. On one hand, I wasn’t really attracted to him. On the other hand, I had just spent the last hour and a half making out with him, and he had bought all my drinks. That seemed to argue in favor of a second date. Though agreeing to a second date with a guy just because he insisted on paying for my mojitos seemed counter-productive, and if we had a second date I might feel obliged to sleep with him, as a matter of politeness ... But one can't fuck a guy solely to seem well mannered.

Then I reminded myself that my goal here was quantity, and and Chris would be another notch on my bedpost, should I ever happen to have one. And just cause you’re not attracted to someone doesn’t mean the sex can’t be good, right? Until I began Living Somewhat Dangerously last Spring, I’d operated on the principle of never getting it on with someone I wasn't very, very attracted to. Even when I’d been too drunk to exercise judgment, I’d never hooked up with someone I didn’t think I really liked. But kissing guys I've been lukewarm about, like Eddie (prior to this blog), and, come to think of it, Jeremy, who at first didn't hold any great attraction for me -- well, the experience has been extremely enjoyable and enlightening. So maybe getting it on with Chris would be fun. Just how attracted do you have to find a person in order to sleep with him and enjoy it? Of course, if that person is really good in bed, you might start finding them attractive during the act…

The next day Chris emailed me, saying he found me “ridiculously attractive.” Very flattering, and though I couldn’t say the same I wrote back to say that I was going out of town for a bit, and would be in touch soon. That ought to give me some time to mull it over, I figured.

Going Dutch: a Discussion (with Kissing!)

I had a date with Jeremy. He suggested we meet at a place near where he works, off Avenue A. It was one of the first really cold nights of the year (one of the very few, so far) and walking to the bar in the darkness I was a bit frightened. I don’t care how yuppiefied Alphabet City is, it still evokes that terror and admiration that it commanded when it really was the worst neighborhood in Manhattan, not so very long ago at all.

Anyway, it was a nice bar with an exposed brick wall and dim lighting. We sat and drank and talked. Jeremy was personable and intelligent but as he talked I thought, “He reminds me of someone…who?” Then I thought: Amy! I went to college with her. Maybe it was the nose, or the shape of his lips, which were a dark red, like he bit them. But it was hard to feel attracted to someone who reminded me of a girl. I mean, he wasn’t effeminate. And thinking of that, then I noticed who else he reminded me of: Grandpa from The Addams Family! That was definitely the nose. Or do I mean The Munsters? Anyway, gah! I mean, a very youthful looking Grandpa.

But Jeremy really was very easy to talk to and I ended up telling him about temping, and my search for a job with a steady paycheck.

When he asked for the bill he said, “I don’t believe in paying for dates, but I’d like to treat you tonight…”

“Okaaay,” I said. He doesn’t believe in paying for dates? What’s up with that? “You don’t believe in paying for dates?” I asked.

“Well…” he said, and then he went on to say that the last time he had been on a date and offered to pay the woman (I was going to write girl but no, she must be a woman) said, “Why would you want to do that?” which put paid to his offer.

“I would never not let someone pay for me,” I said rather emphatically. “I’m broke.” True. “But also, I don’t know, it’s a date. When you go out on a date you should be prepared to say, ‘This is a date. It’s important, I’m making an effort. I think rituals like paying reinforce the sense that it’s an occasion. It should be.”

I recounted this conversation later to my roommate Jenny, who pointed out that this was a bit self-serving on my part. So it is. Does being a feminist mean I can’t let a guy pay for me? I certainly do appreciate the gesture (and, let’s face it, the savings), and like the sense of formality and solicitousness it suggests. According to Miss Manners, the person who does the asking does the paying. But I don’t really ask guys out, so I never expect to pay. I think a guy should pay on the first date. That being said, I generally offer to contribute my share.

The upshot was that Jeremy paid for me, and then walked me to the corner. He was going to go in for a peck, I think, but I launched myself at him, and there we stood, making out on the corner of Avenue A and 6th Street. I didn’t know if I found him particularly attractive, but it seemed like a good idea. Also, it was freezing and he provided some body heat.Then we said goodbye and I made my way to the train, bemused, with the memory of his lips against my throat.

Jefferson, Part I

NB: This was a week or two ago. I didn't post it right away, for a number of reasons. But now...

The other evening I had a date with Jefferson.

Jefferson emailed me a few weeks ago, after he came across my Craig’s List ad. He sent me a brief note with a link to his blog. I checked out his blog and was completely floored: it was about the dirtiest thing I’d ever seen. He’s a divorced father of four, in his early forties, and apparently all he does is have sex with multiple partners and take care of his kids, though not at the same time. He’s a good writer. All the sex was erotic, the orgy conversations were funny and I was astounded.

I wrote back to say “!” – I thought his writing was great, but I found his depth of experience and number of partners intimidating. I didn’t expect to hear back from him, but he did respond, enclosing a photo. He also used the word “gosh,” which put me at ease. An insightful guy – he could see I am a sucker for what Michael Chabon terms a “dainty lexicon.” His photo showed him to be lanky and blond.

I was so flattered to be the subject of his pursuit. Though of course that doesn’t really make sense, since it appears that Jefferson is not averse to pursuing a fair number of men, women and some transsexuals in the five boroughs. I am a little ashamed to say I was thrilled that a celebrity was interested in me.

I thought I’d like to meet Jefferson – I wanted to see what someone who has huge amounts of group sex looked like in the flesh, as it were – but decided I wouldn’t sleep with him, since he didn’t sound like a safe bet. I noticed that in all of his entries he made a point of mentioning wearing a condom, but it was clear he had sex with a number of men, which I think is dangerous, and is on my list of stuff to be wary of.

Anyway, we wrote back and forth, flirty but not at all explicit emails, which is just how I prefer things to be. Eventually we agreed to meet for a drink on Saturday evening.

When he turned up I was, again, totally surprised. Cute, definitely, but I never ever would have would have picked him out of a line-up as the Man Most Likely to Host Orgies. Come to think, who would I pick out of a line up for that? Hmmm, Jonathan Rhys Meyers, circa Velvet Goldmine, I expect. Anyway. Jefferson was nice, and smart, and older than the men I usually hook up wih. But I loved the idea of being named in his blog! Apparently I want to be a star fucker.

We talked for a few hours, about things like whether or not I might consent to go to bed with him, the nature of submission, and how, when he was a child, he was told that being gay meant you masturbated over a bowl of cornflakes.

“Submissives really have all the power,” Jefferson explained as I gulped down my gin and tonic. “They hold the safeword, and the dominant does all the work.”

“Yes ... Have you ever read Anna Karenina?”

“Yes…”

“Well, you know how Levin proposes to Kitty? And she turns him down at first? There’s this whole discussion about it. Basically, all Kitty can do is say yes or no, but by saying yes or no, she wields a lot of power over Levin. She holds all the cards. She can’t do much with the cards,” I admitted, “But Levin can’t do anything without her say so, either.”

We considered that. Later, I thought, being dominant is like playing the queen in chess: you have all the powerful moves, but your status isn’t actually that important. Only the king, whose movements are totally circumscribed, is of import in the outcome of the game. Being submissive is like playing the king.

By the end of the date I was pretty keen to sleep with Jefferson. He’s cute, very easy to talk to, nice, complimentary. There’s something to be said for older men. It’s so easy to feel comfortable with someone when he makes it clear he thinks you’re hot. Or takes pains to let you think so, at any rate.

After several gins and tonics, I was comfortable enough to tell him a bit about my experiences (including my big experiment with Jordan), and we talked frankly about what I might like, how his sex life sounds high risk to me, and how terrified I am of contracting HIV. But the more we talked, the more I felt like these objections could be overcome. Perhaps it was the alcohol. He was so funny and friendly and picked up on my physical standoffishness. He didn’t even brush my hand. It was late in the evening when he briefly touched my cheek. At that point I was pretty lightheaded. “See, thanks!” I slurred. “I mean, I appreciate that you waited until I’d had three drinks before you touched me.” I wasn’t being sarcastic: when he finally did get around to making contact, I was comfortable.

He had plans for later, but he leaned over and whispered in his soft Southern accent, “I’m trying to decide whether or not I have time to take you home and fuck you before dinner,” he said. I burst out laughing. It turned out that Jefferson had to meet with one of his girlfriends for dinner later. “I don’t want to keep you,” I said. Also, I wouldn’t like to think that he would be watching the clock the whole time we were together. Reading his blog, it’s clear he is on a really tight schedule.

“Let me look at my schedule,” he promised. “Is it OK if it can’t be this week?

“No, take you time,” I said, flattered. “I’m sort of amazed you might be able to fit me in at all.”

“Well, I want to see you soon,” he said. “So maybe next week.”

“OK.” We got up to leave.

At the corner we faced one another purposefully. “Well, it was so nice to meet you,” I said.

“I’m going to kiss you now,” he warned.

“Yeah, yeah!” I said, in a “Of course, go ahead,” voice. So he did. It was funny. His kiss was very light, his lips soft. We made out. I nipped at his lip just a little. Then we bid one anther goodbye, and headed our separate ways.

Later, I got a very nice note from him. That’s Southern manners for you. Then he offered to have an HIV test. Which was even nicer.

So we’re fixed up for Tuesday, though we’ve agreed that this time we’re not going to have sex since, as I put it,

"I like the thought of getting all worked up, and of being denied (this one time, anyway) -- that's actually quite pervy, isn't it?"

And he agreed.

Another First Date That Won't Result in Sex

The other night I met Jon. He emailed me on the Nerve personals. In his profile, he said that he had a girlfriend but that theirs was an open relationship. This made me think of Tim and Amanda. His photo, from what I could see of it, was cute. It would be a new experience for me, so I responded to his wink.

After much back and forth, including his invitation for me to meet him at his apartment (No, no, no) it was agreed that I’d stop by the bar he works in on Tuesday night. I thought this wasn’t a great idea, since I figured it would be crowded, he’d be distracted, and I’d feel surplus to requirements. Nonetheless, what the hell.

I went to the bar, which was not at all crowded when I got there just before 8:00. He’d told me he was a bartender, and he’d be the only one there, but when I arrived I thought perhaps someone else was working instead of him. The bartender didn’t really resemble Jon’s picture at all, at least what I’d seen of it. He was short and stocky, with close-clipped dark hair and several silver rings on his fingers. I sat at the bar. “Hi, Lily,” he said.

“Hi Jon,” I said.

“You want a Cosmo?”

I nodded.

He was all right. He had a moderate Philadelphia accent and a huge chip on his shoulder: he’s a not very successful actor, poor man. Within twenty minutes of meeting, he’d managed to let it drop that he’d had three callbacks for this musical, that he was really artistic, and that, while his girlfriend tolerated his non-monogamy, she actually hated it. “But we’ve talked about it a lot,” her said, “And she knows that the only way for me not to feel trapped is to be able to have sex with other women. But she doesn’t want to hear about it.”

“Oh,” I said, thinking, I’m sure his girlfriend can do better. If she doesn’t like him sleeping with other women, why doesn’t she dump him? I don’t think I could be happy knowing that someone I was committed to was regularly bedding other women, or trying to. At this point, there was no way in hell I’d ever want to sleep with him, especially after he made a joke about “seeing if we’re going to bang.” Now that’s class. “I’m just kidding,” he added, anxiously. “You know I’m kidding cause I said ‘bang,’” I nodded, smiling politely. No way, pal, was my thought.

I felt sorry for him. He’s not particularly young, a bit burnt out from constant auditioning, and working as a bartender at a not very nice place. He seemed frustrated. I would be too, if I was a thirtysomething bartender struggling to get a break. Still. I’m not going to bang him, thank you.

Ron and the Theory of Lateness

Well. I had a busy, but not dirty, weekend.

On Friday night I had a date (courtesy of Craig’s List) with Ron. We had originally planned to meet on Saturday night, but on Friday morning I got an email from him asking what I was up to. I thought (erroneously) that he meant What are you up to tonight? I said I could probably meet up. After some back and forth, it was agreed we’d meet at 11:00, at a bar near Marc’s place in Hell’s Kitchen. It’s a pub I used to go to all the time with Marc and his old roommate—very congenial, nice wait staff, comfortable chairs, etc. I checked in with Marc to see if I could crash at his. Luckily, he was fine with it.

A note on Ron. He’s 27, and from his emails I had decided he was sort of passive aggressive. Like, he asked where I wanted to meet, then said he liked dive bars. I, of course, prefer swanky, quiet lounges. I said a dive bar would be fine, as long as it wasn’t too loud. Did he know of one? No, he said, where would I like to go?

I said How about Bar X, on the West Side?

The West Side? He said, Eek. (I quote). But I guess it would be OK.

Well, I volleyed, is there any place you’d like to go?

No, no … Any dive bar would be good.

So suggest one, I thought but did not say. Here, I said, I did a search on Citysearch, and both of these places came up under “dive”. He made no comment whatsoever on either of these places, neither of which were on the (eek!) West Side.

Eventually we agreed on Bar X.

Then, he texted me that evening: So, Bar X is a good place?

Me: Well, I like it. Unless there’s somewhere else you want to go. (That last part was not actually written in italics.)

Him: No, no, unless you want to come to Neighborhood Y.

NB: Neighborhood Y is in Brooklyn. I do not live in Brooklyn. Neighborhood Y is not, you know, just over the border in Brooklyn. It is a fair ways on the subway.

I was immediately irritated, and thought: how rude! Why would he suggest someplace so inconvenient? Unless, of course, he thinks I’m going to sleep with him tonight. How dare he?! Um, nevermind that I’ve made it clear I’m up for casual sex… It had occurred to me that I might want to sleep with him that night, but I’d found our whole email exchange so tedious I’d dismissed the thought and was hoping our in person meeting would make him a bit more attractive. But did he expect me to sleep with him? The nerve! Et cetera. Listen, I thought, giving free reign to my bitch goddess alter ego, the one who lives entirely in my offended brain, If I want to sleep with you, I’ll let you know. I’m not going to Neighborhood Y on the off chance that I find you appealing enough to bed you tonight.

I didn’t say this, of course, just said Neighborhood Y was a bit inconvenient for me, and so at last Bar X was confirmed. Jesus!

I arrived at the bar at 11:00, only to see a text from Ron, saying he’d be here closer to 11:15. I took a seat and ordered a drink, feeling awkward. Like there was a sign on my forehead: STOOD UP.

By 11:20 I was very annoyed indeed. It’s funny, but before I started my whole casual sex campaign, I was never really bothered by lateness. In fact, I was often the late party. Here’s what I think it is: I think that because I’m presenting myself as not looking for a serious relationship, I am afraid boys won’t respect me. This, of course, begs the question: Why should I care if boys don’t respect me? This isn’t the tenth grade. It doesn’t matter. However, it stands: I am now very protective of my dignity. I figure that if I’m not going to behave within the accepted parameters of traditional courtship, I’m going to have to go that extra mile to make it clear I expect the benefits of traditional courtship: that is, the appearance, if not the actual presence, of the deference usually accorded a woman on a date. In this case, that translates into me being really irked if a guy is late. I never used to care. But, for example, last week, when Daniel was over half an hour late, I was livid. It seemed to me that he wouldn’t have been late for someone he didn’t think was easy. This whole argument is silly on so many levels, yet I feel compelled to demand at least the appearance of respect that being on time would suggest.

At 11:30 I asked for the check. At last Ron showed up, and apologized. I said it was fine cause, really, if I didn't think it was fine, I could leave. I wasn't going anywhere at this point. When the check arrived, he apologized even more, betraying a flattering degree of alarm. As it turns out, Ron is a music promoter, and he’d actually been working that night. When he’d said earlier that he was going to a show, I didn’t realize it was part of his actual job. After that, I relented internally, and let it drop.

We chatted. He talked nineteen to the dozen, and took a call on his mobile in the midst of our conversation. Again, I thought this was pretty rude, but my indignation subsided when he explained that it was his mother, calling about the Cardinals’ World Series win (he’s from St. Louis). A call from one’s mother is acceptable, I feel.

Anyway, he was cute, but, eh. I wasn’t really interested. A bit effeminate, lots of self justifying talk. He was nice, but I just didn’t find him attractive. We bid farewell around 1:00 and I considered a polite way to blow him off.

Score!

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