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.

Half-Naked Thursday, and Kink For All

Like everyone, I had a fab, fab, fab time at Kink For All NYC on Sunday. Originally, I was hesitant to attend, since I am not really kinky. But I did go, and really enjoyed myself. Plus I ate delicious toffee-covered Saltines.

Kink for All was “unorganized” by SaraEileen and MayMay, and I went to presentations by them, Sascha, a Kinky Jew, Boymeat (who spoke very thoughtfully about leather stuff), Sinclair Sexsmith, Barbara Carrellas, Tilda (graphic genius--her slide show, and MayMay's nerdy gender tech talk were probably my favorites), and lots more. Plus I saw Calico, Viviane, Lolita, Axe, and several people I was too shy to approach. But my favorite moment was during Nickel Dakota's fetish filmmaking presentation when he explained, “I think, for the female armpit fetish films, I'm going to have to switch to HD.” Indeed. Then I pulled, but that, as they say, is another story.

Anyway, you may have noticed a few changes to my blog. Namely, you can now see me half-naked. It's all part of my subtle plan for Total Blog Domination Via Tasteful Nudes, and I hope you like them. The pictures are of me, and were taken by My Friend Jake (not to be confused with Jacob or Big Jake). Thanks, Jake!

In Which The New Year Suddenly Doesn't Look So Bad

When Jed turned up I was feeling low. It was a bitter Tuesday night, and I’d finally kicked Dean to the curb. Worse, he hadn’t even protested.

On New Year’s Eve I’d decided on the following resolutions:

• Maintain weight loss
• Write for one hour (or at least one page) every day
• Pitch and write at least two freelance articles
• Meet man I will love, make happy, and eventually marry (and vice versa)
• Continue good work on the gym-going and money-saving front

Number four was the big one, obviously. Shortly after Dean and I had broken up back in July, I’d decided it was time for me to settle down, and I thought that officially committing to meeting someone — and believing I could commit to meet someone as I’d committed to losing 15 pounds — ought to work. But this plan to meet someone else was currently stalled, since I was spending valuable dating time making out with my ex boyfriend.

“Um, I don’t know if you want to hear this,” Ashley had said a few weeks back, when I’d told her about my impending Christmas visit with Dean and his family. “But I don’t think things are really finished between you two.”

I smiled sheepishly. But in fact I was pleased: If we weren’t finished, then there was more to come.

But January had turned my head around: Dean didn’t want to get back together; for that matter, neither did I. I wanted to get married, and Dean had made it clear he didn’t, at least not to me. And I saw that the more I hung around with him, sitting in restaurants with our knees pressed together under the table and splitting a bottle of wine, the less time I would have to meet an employed, non-pothead adult male who might want to fuck me silly and have kids.

So one night early in the New Year I told Dean this: “Look,” I gulped my wine. “I’m going to have to cut you loose,” I said, after he had once again mentioned the possibility of us returning to Mohonk for a romantic President’s Day weekend.

He raised his eyebrows; I touched his arm. “Dean,” I began. “I couldn’t love you more,” I said at last. True. “It’s not that. It’s just that I don’t think it’s a good idea for us to spend time together. I want to find someone, and the time I spend with you is time that I really should be looking for someone else.”

He didn’t even blink: “I totally understand,” he said, squeezing my shoulder. “I want you to be happy, you know.”

I mean, he didn’t even have any regrets!

This was all very informative for me, since, as I later told Ashley, I’d sort of been hoping he’d say, “Oh, Lily, I don’t want to give you up, let me think about this…” Since July, I thought we’d both been responsible adults who’d been forging a new friendship. Instead apparently I’d hoped I had an ace up my sleeve. And why? I didn’t want to marry someone with Dean’s sense of entitlement and disinclination to grow up, did I?

Anyway, the point is, I went back onto the personals site on which I’d met Dean, and reactivated my profile. So had he, I discovered—and he’d managed to shave nine years off his age! Now he was younger than I!

“That’s appalling!” Ashley exploded when I told her of this development the following day at work. “I mean, that’s just gross. What kind of a Peter Pan thing does this Dean have going on, anyway?”

In Laurie Colwin’s A Big Storm Knocked it Over, the main character’s best friend, Edie, has a really unpleasant family. Sometimes, the heroine, Jane Louise, will insult them on Edie’s behalf. And Edie says, “Thank you for hating my family for me.”

I said now, “Thank you for hating my ex for me.” Then I went back to work, my righteous indignation providing a little warming flame in the arctic wasteland of my romantic prospects.

**
So the next night, while I was glad to see Jed, I was still smarting a bit. But I feel casual sex is generally good for taking one’s mind off of serious romantic problems.

When Jed arrived, I couldn’t help feeling better—it’s a real pleasure to see someone as enthusiastic and as interested in the world as he is. “You look great,” he said, which I always like to hear. “It’s good to see you again.” Jed’s compliments always make me feel a little bashful, even if they’re as innocuous as these—there’s just such an energetic sincerity there, it’s very flattering.

“You, too.” Jed settled himself in a chair and pulled it across from me, sitting on my bed. He hooked his legs around mine and smiled at me. “You cut your hair!” I said at last.

He grinned, and ran his hands through his short ’do. What had been blond curls was now shorn close to his head, a blondish brown. “I tried to dread my hair, but it didn’t work,” he explained.

“I like it!”

He looked more grown up with short hair. We sat there, our legs linked, smiling. I was glad to see him—he made Dean seem far away. We were both quiet for a minute. Then Jed said, “I’ve forgotten: Do you like being dominated?”

“You’ve forgotten?” I’m afraid I smirked. “Yeah, I like it.” He smiled at me, and leaned forward.

**
He pushed me gently back against my mattress. I stared up and him, waiting. “Take that off,” he said, pointing to my sweater. I obeyed. I felt … smug, satisfied, like he was doing what I wanted when he told me what to do.

He lay on top of me and I could feel his erection through his jeans (more smugness on my part). Jed started to undress, and when he had dragged off his jeans and was just in his underwear, he leaned over me to kiss my belly, my thighs. I was thinking that this was sort of an unusual move on his part—in fact he’s never gone down on me (though I’ve never asked, either) and mostly we sort of devour one another’s mouths before I just impale myself on his cock. I was thinking that when he slipped a finger across my clit. I was (satisfyingly) wet. Then he sat up on his knees and thrust his dick at me: “Suck my cock.”

I sighed with pleasure and stroked my mouth along his silky skin. “Suck that cock, Lily,” he said again. I think I got a little wetter just hearing my name. “Good girl.” At that I felt the walls of my pussy start to clench in excitement, and I slipped my mouth around as much of him as I could manage and sucked it long and slow. “You’re such a slut!” Jed sounded pleased. I smiled into his thighs.

“I’m going to ram my cock into you,” he went on thoughtfully. I thrust my whole upper body forward, licking the underside of his dick with a staccato rhythm. I was wet and almost frantic. I wanted Jed to leave my apartment thinking, “Oh my God, Lily gives the best blow jobs ever!” When he shifted slightly I got onto all fours in front of him, wagging my tits as I sucked him. “Oh, God, Lily!” Jed said again. “Get a condom.” I obeyed (again, smugly).

“You like that? You like that?” he muttered as he drove his cock into me. He’s such a good fit, big but not too thick (like Big Jake). Jed’s dick seemed to push me open in all the right ways.

“Yeah,” I mumbled.

“You like fucking me?” Jed pushed my hands to the side of my head and held my wrists. I groaned a little. We stayed like that for a while. My eyes never left his face, while the rest of our bodies jerked and twisted across my bed. “You want to get on top?” I nodded.

I levered myself against him, stretched my legs out, and then I pushed myself against his cock, the tight thick tension bubbling inside me. “You’re my cum dump,” Jed whispered. “Just a little hole for me to use. How do you like your little body being used by me? Do you like being used by me?”

“Uh, I do!”

“I’m just going to pump my cum into you,” Jed went on. “You want me to come all over you?”

“Yes,” I gasped. “Come all over my face!” I don’t think anyone’s ever done that, come to think of it. But I would like it if Jed did. I rocked back and forth, so close to orgasm. My legs were shaking and I was sweating. But it was draining, this pleasure, and I didn’t know if I could sustain the muscle spasms that are both necessary and a sort of internal signal for me to come. “I wish I could have you in my mouth and my pussy at the same time.”

“I bet you’d like to fuck two guys at once.”

“Yeah. I could suck one guy while you fucked me.” The idea made me shake violently: I saw myself on all fours, blindly sucking a stranger’s cock while Jed rammed himself inside me. “Yeah,” Jed went on. “Two guys using you as a cum dump. I’ll call up one of my friends and say, ‘Come on, let’s fuck Lily.’” That’s when I came really hard.

“Anytime you want a threesome, just let me know,” Jed offered after I’d recovered my breath. I squirmed a little, a little aftereffect of orgasm.

After a glass of water I slid down to nuzzle his dick. I stroked my fingers, then my tongue, across his balls. At last I slid my index finger back and gave his ass a tentative poke. Jed shifted to give me more access; I knew this was his favorite. Soon I had worked two fingers up his ass and Jed was breathing heavily: “Oh, Lily.”

“Do you want me to fuck your ass?”

In reply he took out a thick, red-orange dildo. Jesus, it was big! “Pass me the lube,” he said. (Jed always brings his own Babelube when he visits. I ought to invest in some myself. I probably have it to thank for the pain-free and generally incredibly hot sex we have. After all, nobody else has fucked my ass. Anyway.) I doused the dildo in lube. It really looked too big to fit into Jed’s hole, though I assumed this was the equipment I’d fucked him with before.

“OK,” I said, “You direct me.” I was afraid I’d shove it in too fast.

“Just push it in slowly.” I pushed and met a solid wall of resistance. “Up,” he said, so I adjusted the dildo. I was able to push it in a bit. “More lube,” Jed croaked. He splashed lube all over it and lay back down, lifting his ass up for me.

“Look at you,” I murmured. “Just look at that ass.” It was getting wider.

After a few more stalled starts the dildo slid in and, at Jed’s command, I pulled it all the way out, slowly. Now I could see his asshole stretched wide open—this puckered hole. Christ. Then I pushed it back in, and started pumping it back and forth.
“Oh God, that feels good!”

I smirked. “You like that? You like being fucked?” I was using almost the same words he’d said to me. I was on my haunches on an old beach towel, ramming an enormous dildo up Jed’s ass. “God, look at you,” I was a little wet.

“Yeah, I like having you fuck me,” Jed said breathlessly. “That’s really good.” He tugged at his cock. “Ah….” And then: “I’m going to come.”

“You’re going to come for me?” I squeezed the walls of my pussy, watching him struggle. “I want you to come.”

“Oh, Lily,” he cried, and came, splashing his stomach with come. I smiled at him, and then I did something I rarely do. I bent over and licked a drop, while Jed watched me under lazy lids. It tasted sort of sweet, actually.