Tuesday, February 24, 2009

In Which Various Verbs Happen to Me

Hey, can I booty call you?

This instant message had appeared on my computer screen the previous Saturday night, and it was from Big Jake. We’d had sex a few weeks previously at a party at which I got so unbelievably drunk — Suffice it to say I had sex with Jake, and I was sorry I was not sober enough to enjoy it (or, who knows, not enjoy it). This was just before Christmas, and of late we’d been in touch.

On Saturday night I was tired and already in my pajamas, so I declined. But when he emailed me Monday and asked what I was doing on Tuesday night, I told him to consider himself booked.

We met at this Mexican place right near me. I had walked past it literally dozens of times and had never noticed it! Anyway, we had dinner and gossiped. On the way back to my place we stopped off to buy condoms, because though I had some, Jake needed Magnums!

Back at my place we settled on my bed. We were both dressed. We talked about nothing in particular, and slowly his hand slid towards my arm, and my foot nestled against his leg. I couldn’t—or wouldn’t—kiss him, I wanted to be the one kissed. Jake appeared to have no problem just sitting around chatting, though his hands did stray towards my thigh. When I managed to finally lean my torso against his, I explained, “This is about as bold as I get.”

We started to kiss and, still fully clothed, we strained towards one another… oh, who am I kidding? We were dry humping. Rubbing ourselves against one another, my corduroy against his jeans. My rayon blend against his cotton. I was really turned on (by the humping, not the fabrics).

Our shirts came off and I dove into his skin, trying to decipher and claim his smell. “Be sure to tell me what you like,” I murmured as I trailed my mouth across his chest.

“You can bite my nipples,” he volunteered. I obliged. “Harder.” I bit so hard I was afraid I’d break the skin, but he just moaned. I liked that. I smiled into his skin and latched my teeth to his nipples, again.

Eventually we were naked and Jake went right for my pussy, his tongue slipping across my clit. How can I say this? It was Big Oral Sex. I can’t describe it, except to say his tongue seemed to cover all of my pussy at once, it was like being washed. I came, and when I’d caught my breath Jake bent over me once again and, with a finger slick inside me, made me orgasm a second time.

I felt completely drained, and he hadn’t even penetrated me. I didn’t think I could manage another orgasm. I decided to go down on him.

Big Jake is, of course, Big. His dick is as long as Daniel’s but thicker, and when we’d fucked that night some weeks back, it had hurt a bit, having him inside me (not to mention that he’s a really pounding kind of fucker—a relentless, solid thrumming). Afterwards, I’d been very sore. Not to mention that my lower lip was actually swollen and bruised from sucking him so much. Yes. All in all, not my finest hour.

I just stared at his dick for a bit, then attempted to suck him. I couldn’t get much of him into my mouth, and my tongue and the insides of my cheeks were dry; he hadn’t produced any pre cum.

But soon enough he put me on my back and opened my legs. “Go slow!” I ordered, the memory of being sort of bludgeoned by his cock still fresh in my mind.

“Don’t worry,” said Big Jake—I guess he’s heard that before. And then he very slowly slid inside me, and I relaxed my pussy as much as I could, my legs stretched around his back. It still felt pretty big. Once he was in me he started thrusting. It was a kind of painful pleasure, feeling him sliiiiiiiiide in and out. And as he was fucking I thought, He’s attentive and polite, but I can’t imagine cuddling. I wasn’t at ease.

This surprised me, because previously I’d always found Jake very engaging. He’s sort of wholesome looking, with close-cropped hair and a good-natured face, and a big, solid body. He looks like someone who’d be glad to help you move your heavy furniture. Anyway, prior to fucking him some weeks previously, he’d always been friendly when we’d run into each other. But in my bed, that warmth was absent. I wondered about this. Callie speaks highly of Jake, and makes him sound like a total sweetheart. But I wasn't getting that vibe from him tonight.

He put my legs close together so that I could feel his cock rub against my thighs while he fucked me shallowly. He held my hands above my head, which I would have loved if the pummeling his dick was giving me wasn’t quite so athletic.

“Do you want to get on top?” he asked. I nodded. He pulled out, and I clambered up. I breathed deeply, and slowly sat down on his dick. I started riding him and he (like every other guy I’ve fucked) immediately started rocking beneath me. “Let me do the work,” I croaked. This sort of worked, but for some reason I was incapable telling him the rest of the things that make me come: Talk dirty. Lick my nipples.

But he sucked my nipples, and made an effort not to buck beneath me. “I love being inside you,” he rasped. My legs were trembling, and I realized that they’d been trembling for what seemed like ages. I was close to orgasm, but I didn’t think my muscles had it in me to come again. And then I had to stop, I was just worn out.

Jake put me on all fours (a position that’s usually uncomfortable for me) but he was thrusting faster and faster and I could tell he was about to come, so I didn’t mind—I wanted to see (and feel) him come. He pulled my hair. “Ow! Not my hair!” Seriously, that’s painful.


I like the idea of being on all fours more than I like the mechanics. I love the thought of being in such a submissive, animal-like position, but (again, I think this is because of my tipped uterus), it just doesn’t feel comfortable. Jake breathed in my ear.

I turned my head: “You going to come?”


“Yeah, I want you to come inside me,” I gasped between thrusts. “Come for me, Jake.” He gripped my shoulders tight and his body jerked against mine. I felt satisfied, like I’d achieved something.

Afterwards we lay next to one another, and he stroked my hair. I wondered if it felt strange to him, because it felt strange to me. I mean, I like having my hair stroked, but it feels intimate, and tender, and that was one thing Jake was not. At least not tonight. We chatted in a desultory manner for a few minutes, then he said, “Want to sit on my face?” Sort of casually, like, Want a Coke?

“I don’t think I can take it,” I admitted. But shortly thereafter I went down on him again. I bent over and licked the length of him, bringing my eyes up to meet his “Oh,” said Jake, “I like to see you like this.” Ooooh, that’s the kind of thing I like to hear. I went at him more eagerly, and I think he called me a “good slut” (always welcome) then he sat up, “I want to fuck you again.”


Jake fit on another condom and briskly pushed inside me. He wrapped my ankles around his neck, and kissed my ankle. I liked the ankle kissing (how come Dean never did that?) but with his dick, I just could not have him that deep inside. “Ow!” I gulped. “That’s not—” So I slid my legs down to Jake’s waist. He kept pounding me with his cock. The pain was close to pleasure, but alas, not as close as I would have liked. My head banged against the headboard, and I hoped my neighbor wasn’t home.

I whipped my head back and forth, like I was struggling to get away, and then Jake pinned my arms down, which soothed me a bit. I could feel my face twist into a strange grimace. “Oh, you’re so hot,” said Jake. Then, “I’m going to come.”

“Yeah,” I breathed, “Yeah.” Jake’s face was screwed up and it was the only time I’d seen him out of control. I felt warmly towards him then, and when he came hard in my arms I stroked his back and murmured his name.

Tuesday, February 17, 2009

I Fall Off the Wagon

After being dumped by two men in the space of five days, I began to reflect. Well, first I felt sorry for myself, but eventually I began to reflect. And what I reflected was that I missed Dean.

Which was really only natural—I had been dallying with Aaron, and Jed, and Daniel—lovely boys, all—to keep myself from thinking about Dean, whom I missed, and loved. Because I hadn’t cried much, and thought I had come to terms with the fact that we had no future together, I’d thought I’d put him behind me.

Since our breakup, we’d gotten together sporadically for dinner, and after the first, awkward meal, our dinners had been punctuated by lots of kissing and cuddling. I had, however, refused to sleep with him. My feeling was, if we didn’t have sex, there was no emotional danger. My feeling was, also, why should I have sex with him? If he wanted to fuck me so badly, let him attempt to get me back. Shallow, but true. So we hung out, and held hands, and he gently tried to cajole me into bed, which put me in the comfortable position of denying him and feeling superior—for either denying him or for not wanting to have sex with him, I didn’t know which.

But I hadn’t seen him in a few weeks. Dean had cancelled on me on election night—we were supposed to watch the returns together, but instead he stayed in Atlantic City to play poker, and I’d been angry, unwilling to express my anger, and frustrated and lonely. When we finally did see one another, it was almost Christmas. This time last year, we’d been an official couple, planning to spend the holiday together.

“I didn’t realize that not wanting to get back together with him didn’t mean that I don’t miss him,” I announced to Ashley, the recipient of all my Dean-related musings.

“You haven’t really mourned him,” she pointed out obligingly.

So when we met to see a film, I was anxious. We had some time, so stopped for a drink at a sushi place first. I sat there sulking, wondering if Dean was seeing anybody else.

We discussed our Christmas plans. As usual, Dean was spending the holiday with his mother and one of his sisters, something he viewed more as penance than a cause for celebration. On the other hand, he was going to the resort where his family had spent the last umpteen Christmases, a place I’d visited with him last year. It was a wood and stone nineteenth century hotel about two hours from New York City. They had a spa, and the night we’d arrived, we’d sat in the outdoor hot tub overlooking the mountains, sleet melting on our warm faces. The hotel was still owned by members of the same family who’d founded it over a hundred years ago, and they ran it like a very lavish summer camp, with group activities and assigned dinner hours. We’d stayed in a room with a four poster bed and a wood-burning fireplace. Christmas had been like a Victorian dream, complete with tree-trimming parties and ice skating, and I’d loved the hotel so much I hadn’t wanted to leave.

“Well, on Christmas Day, I’ll probably go to the movies and out to dinner with my parents.” This is, of course, the traditional New York Jew Christmas.

“Do you want to come to the hotel?”

He’d asked me before, and I’d demurred – I’d loved being asked, but thought it a terrible idea. But now, I really wanted to go. “Do you want me to come?” I asked, like a passive-aggressive teenager.

Dean gave me a look. “Yes, of course.”

So probably he wasn’t seeing else. At least no one he expected to be sleeping with over Christmas. “OK,” I said sullenly, and tentatively stretched my hand towards him.

He clasped my palm and smiled.


I went up the day after Christmas, and Dean met me in the hotel’s lobby. He was wearing the same sweatshirt and jeans he always wore, and when he hugged me it felt like nothing had changed. He took my hand and we traipsed up the oak staircase to the room we would be sharing.

This room also had a fireplace, and the thin wooden shutters on the narrow windows were open to show an expanse of snowy lawn. “I have presents for you,” said Dean. He gave me a copy of Holidays on Ice, and a Scrabble travel edition. We started a game, and he ate some of the cookies I’d made him. But this was mostly a prelude to the energetic wrestling the queen-sized bed seemed to invite. We rolled around for a bit in the late-afternoon semi-dusk, nipping and kissing like a pair of kittens.

“I have an idea,” Dean whispered. He was lying on top of me.


“The winner—” he gestured to the abandoned Scrabble game nearby, “Gets to decide if he or she wants to sleep with the loser.”


“Did you say ‘why’?”

“What? I didn’t say why! I said ‘OK.’”

“Oh,” he kissed my neck.

“Really, Dean,” I gazed at the ceiling. “Of course I’m going to sleep with you.” I sniggered. “How churlish would it have been to accept your invitation and not have sex with you?!”

“Oh, so you’re going to have sex with me to be polite?” Dean looked skeptical.

“I wanted to come up here. If I had to sleep with you to do it, so be it,” I said virtuously. I buried my mouth in his neck.


Later we joined the rest of the party: his mother, sister, family friends—just like old times, I thought, half horrified, half delighted. At dinner, with his hands tugging my hair, and exchanging kisses and jokes like any happy couple, I wondered if the others knew or care that we were not actually dating, because we sure were acting like it. After dinner we all went for a walk in the moonlight, our feet crunching over the snow. Dean and I held hands in peaceful silence.

He was so familiar. But back in the room, making out, unbuttoning my cotton jersey and wrapping his mouth around my breasts, I felt detached, and I wondered if that was the price I was going to pay for having sex with Dean: I was going to be aware of just how stupid an idea it was not just after but while we were fucking.

But meanwhile his skin felt good against mine. He turned out the light, and started to go down on me. Then I froze: I was willing to fuck him but apparently oral sex was a bridge too far. “Stop,” I croaked.

“You don’t want me to—”


“But you’re so yummy.” I shook my head. Dean licked his fingers, and rubbed his index finger across my clit. Suddenly, I was annoyed: he should know better. “Lighter,” I hissed.

And then it was all too familiar, the way he fitted his dick into me, the way he lay ¾ on his side, the way we pressed against one another. “Oh, sweetie,” he said, his voice hoarse. I waited.

“Oh, Lily,” he said. I clutched his shoulders. “Do you want to get on top?”

“No, it’s OK,” I said, but he insisted. I had no interest in coming: I wanted to stay uninvolved, which is probably something I should have realized before we started fucking. I rode him a bit but, even though he knows how, in order to come, I need my partner to stay as still as possible, moving only to lick my nipples or, you know, moan my name in a sexy manner—but despite all that, Dean clutched my breasts clumsily and jerked beneath me. Perversely, I was pleased. “It’s OK,” I said at last. “You come.”

We rolled back so that he was on top of me again. “I love you, Lily,” he said. This was what I’d been waiting for, and I forgave him everything, everything. “I love you, too,” I whispered.


Thus our weekend. The following night we sat in the hotel bar – a dimly lit place with plush seating and plum-colored cocktails, and Dean said, “Well, now that we’re having sex again—”

“Dean,” I said, taking his arm. “This is a one-off. I mean, this is wonderful, but.” We looked at one another. “This isn’t daily life.” I mean, again, if we weren’t dating, why should I have sex with him? Why should he have all the benefits of a relationship without any of the attendant requirements, like seeing the person on a regular basis?

“So we could come up on President’s Day weekend and have sex then?”

I admit, I was tempted: “We’ll see.”

And instead of articulating I miss you, this is hard, I just told him that I’d been having a rough time. Until recently, I hadn’t really had the chance to miss him—we’d been seeing one another. If I had called him and said I must see you, please come over, he would have done it. And I didn’t want to get back together with him but he smelled so good, and was so funny and kind and he loved me and I’d been happy with him.

That night again I wouldn’t let him go down on me, and when I rode him and he pushed up against me, interrupting my rhythm, I said, “Dean, you know how I like it,” in a distracted, irritable way. Then I ground myself against his cock until orgasm.

“I love you, Lily,” he said, jerking against me. I felt a wave of love and despair.

"Oh baby,” I said sadly, “I love you, too.”

Sunday, February 08, 2009

Is the Universe Telling Me Something? And If So, Why Is It Being So Blunt?

NB: I am still catching up on old entries. This is (ahem) quite an old one.

I had a pre-Thanksgiving dinner. I invited
Ned and Olivia, and Sweetheart Daniel. We sat at my foldaway wood table from Target and ate roast turkey, baked sweet potatoes, cranberry applesauce, salad with pecans and goat cheese, string beans with shaved almonds and gingerbread. Not an exhaustive menu, but a reasonably expansive one for a Tuesday night dinner party of four. We watched A Charlie Brown Thanksgiving and Dancing With the Stars (my new favorite TV show). After Ned and Olivia left, I settled into my new wooden bed next to Daniel.

Was he wearing cologne? Ever since we started hooking up again I’ve been puzzled by his scent. Because I remember being almost intoxicated with the sweet, musty smell of his neck, but now, while I still like how he smells, it unfamiliar. I sniffed him: “Are you wearing cologne?”

“No.” I think Daniel’s a little bemused by the amount of attention I pay to the hollow of his throat. It just seems important to me.

I curled up next to him and rested my head against his chest. Although I wanted to have sex, I felt sort of distracted—like maybe we could just go to sleep and fuck in the morning. I was tired. I kissed the side of his mouth, and then his mouth, keeping my mouth closed.

“I’ve been thinking,” said Daniel. I gave him an encouraging nod. “It’s not you or anything—” he squeezed my shoulder. “But I think I should take a break from casual sex.”

Well, that was unexpected. “You should?”

He grimaced. “Well.” He paused. “I’m trying to kind of get things in order, and maybe look for a serious relationship.”

“Oh,” I said. “OK.”

I mean, I was OK with it. Though I don’t think that having casual sex with someone precludes you from looking for a serious relationship with someone else. (My fellow blogger Badman has been discussing this here.) But if that’s how Daniel sees it, then that’s reasonable.

We settled back against my headboard, in talking rather than making out mode. “Are you seeing anyone?” he asked.

I sighed. Besides Daniel, and Aaron and, one occasion, Jed, “I see Dean,” I admitted. “And it’s sort of hard.”

And it is hard, but not cause it’s a constant battle to keep from tearing his clothes off or anything. It’s hard, I explained, “Because he gets my jokes and we get along and he’s smart and nice and we’re comfortable,” I said glumly. I know there’s no future and since we’re not sleeping together—despite his persistent, not very strenuous efforts to get me naked, which I find flattering if uncompelling; we make out and he tries to feel me up—I feel then opportunity for inflicting emotional damage is limited. On the other hand, seeing him is distressing. Again, not because I miss him (which I do) but because, frankly, I think he’s throwing his life away and it’s heartbreaking to see an intelligent, talented, good natured guy squander his talents due to pique at not being as successful as his brother. He’s sacrificed a career to his ego. Which makes me want to hit him. Last time I saw him I told him he was going to end up bitter, which he took with good grace and every semblance of having heard me. But really I doubt it’ll have an effect. But, as my co-worker Ashley says, this is no longer my problem.

I said some of this to Daniel and he squeezed my shoulder again and told me I’d meet someone else soon. Well, yeah, probably. I don’t need that kind of reassurance, I want some other kind, I thought fretfully. Or maybe I just want sympathy. Or, you know, dick.

“Well Daniel,” I said. “I am sort of surprised that you waited until now to tell me.” I meant his decision regarding casual sex with me. All that time making conversation with Ned and Olivia! All the time he’d helped me glaze the gingerbread and watch The Simpsons. He’d known all along but hadn’t said anything. That felt weird, and I felt strangely embarrassed. As if I should have been embarrassed for not knowing.

“Well…” said Daniel. “It just didn’t seem like a good time.”

We sat there quietly for a bit longer, and then Daniel said he had to leave. I wasn’t sorry. When he left I curled up alone under my thin quilt, waiting to fall asleep. I didn’t feel like I had the right to be angry with Daniel, or the right to feel anything in particular.

On Sunday night my other twentysomething boyfriend, Aaron, came over. I hadn’t seen him in a few weeks and I felt a little shy when he showed up at my door, his skin cold from the wind. He kissed me lightly on the mouth, and I was pleasantly flustered.

But over dinner we each had a drink and by the time we’d finished I was relaxed and looking forward to getting at his mouth—smelling his neck, sucking him off—all the tings I like to do to boys I find attractive. We ambled back to my apartment and sat on my bed, and then Aaron said, “Are you seeing a lot of people?”

Dean had gone AWOL recently, which was just as well, and Daniel had cut me loose; I’d been on one date with a guy I’d met online. We’d met at a bar and he’d left his belt hang loose around his pudgy waist after a trip to the bathroom. This man had recently sent me an unsigned text message on my phone, and I’d had to thumb through my date book to find out who it was.

“Um, sort of,” I said finally. “Never mind. Are you?”

“Well,” said Aaron, “I’ve been seeing about four people…” He went on to talk about having all these sexual experiences (with Jefferson and others). I nodded emphatically, but it took me a good three or four minutes to realize what he was getting at: he was dumping me! I was being dumped again!

“Listen,” I said at last in my most mature, woman-of-the-world voice, “We don’t have to hook up.”

He smiled, looking mighty relieved. “See, one of the people I’ve been seeing … she never said she wanted me to stop seeing other people, but now I feel guilty … and you know, even if you only see someone once a week…”

I tried to look like I was listening hard, but I was thinking, “I’m not going to get laid again?!” And frankly, part of me though he could have done this via email. By traipsing out to my apartment, he’d gotten my hopes up for sex and a fun evening, even though the visit showed he was trying to do the right thing by breaking things off in person. And of course if he had just disappeared, or dumped me via email, that would have been really disrespectful and I’d have been offended. But here we both were, all awkward, and me sexually frustrated to boot. So we hugged and when he left I stared at my face in the mirror, having been dumped by two younger men in the space of five days. If I keep this up, I’m going to start to think I’m undesirable. I grinned at myself hideously.

I told my co-worker Ashley about this. Ashley is a genius. She is extremely pretty, with long, fine blond hair, deep blue eyes and perfect, poreless skin, with what Fitzgerald would have called “a lovely high color” (pink cheeks). When I first met her, she was so well-groomed I pegged her as a former Delta Gamma pledge chair, but in fact she is not very sorority-like, though she does play beer pong and occasionally says “Dude!” in all seriousness. Anyway, mostly we chat about our boyfriends and our diets. She’s awesome.

I relayed to her the demoralizing dumping by two younger men. She gave me a you should know better look: “The universe is telling you to date someone age-appropriate,” she said.

“I don’t want to date,” I said, horrified. I want to meet someone, fall in love, plan my low-key, semi-formal afternoon wedding and have a few kids (one boy, one girl)—not make small talk and worry that I’ve got something orange in my teeth. Then I sighed: “You’re probably right.”

If my interlude of casual sex with amiable younger men was over, it was time to get serious. It was time to go after what I claimed to want. It was time to go back online, to cut Dean loose, to polish my manners and shoes. “Urfh,” I told Ashley.

She looked up and gave me a crooked smile: “I know,” she said.

Tuesday, February 03, 2009

I Dismiss The Cosmo Kama Sutra

Sunday night doesn’t feel like a night for assignations. So I felt weirdly sneaky as I waited for Aaron in his lobby. After several minutes the elevator door opened and there he stood, wrapped in a white terry cloth bathrobe. “Sorry,” he said. “I was in the shower.” We kissed hello.

I mean, he could have just buzzed me up.

At his floor, we walked down the hallway, and luckily no neighbors saw a guy in a bathrobe ambling around. Then, in his apartment, we sat at his kitchen table, which was located (conveniently) next to his bed. “Do you want to go out?” he asked. Our previous meetings had all involved me eating a meal or three.

But I’d already had dinner: “I was thinking we could fool around.”

“Oh, OK.” Aaron’s smile lit up his face. “You had me there.” He leaned in to kiss me and we shuffled back onto his bed.

He went down on me almost immediately, sort of dove in, and frankly it’s great to be with a guy who so enamored of the … hmmm…. scent/flavor that I am sure I must emit. I lay back on his soft mattress, my eyes half closed.

But I had other things on my mind, and after a bit I indicated he should get on his back. “It’s my turn now,” I explained.

I went down on him, nuzzling his balls and lightly sucking the loose skin there. I rested my head against his thigh, fresh from the shower and smelling of soap. His dick stood stiffly in my fist. I gave him in what I hoped was a wanton, alluring gaze.

“I’d really like you inside me,” I hinted not very subtly.

“Well… sometimes…it’s not the desire…” and after some hemming and hawing he said that sometimes he had trouble getting an erection.

“Oh, OK,” I said. That’s nothing unusual, I could deal with that. As I’ve said before, I don’t feel like it’s sex unless there’s penetration (how old school), and I really did want to fuck him.

I kept on sucking him until he was hard, which he was pretty quickly. I worried that he would be pipped at the post, so to speak, but the condom didn’t cause any problems. I dabbed a little lube across my pussy and he entered me.

I was on my back and he was kind of straddling me. For some reason, we were lying with our heads at the foot of the bed. His face went slack, like he’d just put down a heavy package. I liked that. Then he bent forward and started rocking against me.

After a bit we switched so I could get on top. I twisted and sank on to him with a sigh. I assumed my usual position: legs flexed against Aaron’s, arms on the mattress supporting my upper body. I like it when a guy holds my hips, doesn’t move much (it helps me control the pace), and talks dirty. Aaron didn’t talk dirty, but I came pretty quickly anyway.

While I was recovering, and we’d sorted ourselves out so that our heads were on the pillows, Aaron said, “I never did it that way. I’ve done reverse cowgirl, but you didn’t straddle me… where did you learn that?”

I dunno. It’s my default for orgasm. Dean and I made some efforts with the Cosmo Kama Sutra… With Dean I was keen to try everything out, even thought I knew that any number of the positions would be uncomfortable (why would I want to have sex while touching my toes?) or sexually unrewarding, but when I’m with someone new I want the security of a familiar position with a high chance of orgasm. And it occurred to me that I felt comfortable in this soft bed, next to this sweet-smelling boy ten years my junior, wrapped in his terry cloth robe and smiling sleepily. Sunday night seemed like a comfortable time for an assignation, all of a sudden.

“I dunno,” I said. “It’s just the position my body wants to be in.”

He looked at me with a new respect, like I was this woman of the world. I suppose that compared to him I was. I smiled, closed mouthed, and motioned him towards me.

“You want to fuck me?” I asked, like it was a casual question, like I didn’t care.

He leaned into me, and I breathed in his warm, sweet scent. “Yeah,” he said. I angled my hips towards him and then he swam back inside me, smiling all the while.