Awkward, a Love Story Ch. 02

A shrug.

"She kept a diary."

"Okay."

"And she wrote like an Anais Nin, apparently, though without the sex, imagination, or literary ambition."

My doctor nodded imperceptibly, if at all.

"And she'd been keeping those diaries since she was 11. But when she was about to get married, she had a dilemma. Keep them in her house, or burn them. She was uncomfortable having her husband read her stuff."

"Fair enough."

"So, she handed them to her older sister for safe keeping."

"Okay, though I'm getting a little confused."

"Back to age 18. Maybe 19 by now. I've got my San Diego thing. I'm dating Kristen, but most of the dates are with Caroline as a three-way hang-out at the beach or a pizza place, and Kristen and I don't do much besides kiss. So, I visit at Christmas and Spring Break, and I arrange the summer job in San Diego. I get to live with Caroline's family, which affords outrageous opportunities, since I'm working minimal hours, but her parents and brother have full-time jobs. To be honest, I had a little cash from an inheritance and didn't even get a summer job. It was just a complete fraud which allowed me to make up my so-called work hours that just happened to fit nicely with when Caroline might be home alone. Anyway, I think I mentioned that Caroline has a long history of shifting sexual interests? Well, that was the time we started exploring them in more detail."

Nod.

"That was also the summer in which she became Miss Teen San Diego, though I prefer to call it the Summer of Anal."

"C'mon David."

"I don't think I've ever gotten friendly with anyone who was so fascinated by anal. It started off simply as our birth control method, but she really got into it. She was a transgression machine, in her way."

"Okay, where are we going?"

"I don't know about you, but I'm getting to a point."

"Go ahead."

"So it's that summer before sophomore year, and several things developed that led directly to getting the recent opportunity to tweak Gemma into cumming until she cried."

An eye roll, which seemed outside her usual method, but I do agree that I was going off on a tangent.

"You asked if anybody noticed anything."

Nod.

"Quick story. One night, that summer, I was hanging at Kristen's house in the evening, and was planning my escape so that I could head back to Caroline, who was eager because her parents and younger brother were out of town for some youth sporting event. Did I mention that her brother was an excellent athlete? I used to tell Caroline that everyone in her family had a freakish skill. Her dad was able to watch about 16 hours of sports every weekend, which I felt was somewhat unique, and her mom could find it in herself to like the man, though those characteristics aren't really skills. But her brother was genuinely a great baseball player--ended up getting a scholarship to college and played some minor league ball until he realized he'd never make it to the majors and was--in the meantime--barely making enough money to survive."

"And you told her that her skill was the beauty pageants?"

"You know, you can be a little snobbish sometime. Since you're kind of an intellectual, summarizing Caroline as a beauty contest winner is a bit patronizing."

"Didn't mean to be negative about her. I don't know her."

"And probably best that you don't meet, but I do think you're a little judgy sometimes."

"Judgy, because I'm an intellectual?"

"Well, no, I said 'judgy' because you can be judgmental."

Pause.

"And I didn't say you were an intellectual. I said you were 'kind-of' an intellectual. I mean, you're obviously smart, but you sit around listening to people like me all day. A dyed-in-the-wool intellectual would rather shoot herself in the head than spend her days trying to improve the lives of people such as myself."

Head tilt. She seemed to be thinking.

"So, David, what is her greatest skill?"

"During that period of time, I'd say anal, but I'm a romantic, so lately it's the bleary voice after she's blown me."

"C'mon."

"So, as I'm walking out the door of Kristen's house, literally as I was walking out the door and into a sudden rainstorm, Kristen's older sister asked if I could drop her off. Ordinarily, she'd walk since it was just half a mile, but it was just pouring down rain. One of those huge summer rains that even San Diego gets sometimes. No big deal, and it was a favor that would have been quickly forgotten if she hadn't asked me to come in for a minute. I said I was really tired, and suggested we take a rain check, because--to be honest--the date with Kristen had made me really excited to grab hold of Miss Teen San Diego."

"What happened?"

"Well, I followed her into her house. Uhm, did I mention what she looked like?"

"Does it matter?"

"Oddly enough, it does. She was smaller than Kristen, thinner, more angular. And a bit older, like 7 years older. Different moms, but that doesn't really matter."

"Okay."

"So I came in, and got rained on, and we sat on her couch. She asked how I felt about her sister, and I said I liked her. She nodded, and then she asked me what church I went to in L.A. and how much I liked my cousin's fundamentalist church in San Diego. As you know, I try to be honest, so I shrugged off her questions about religion. I think I emphasized how busy I was. She excused herself, saying she'd been in the same clothes all day and had gotten rained on and needed to get into something more comfortable. Well, when she returned, she was wearing one of those satiny night gown robe things that went down, maybe, to mid-thigh, and her legs were bare. Thin legs, like sticks. She scrunched on the sofa. I couldn't help but notice that the robe parted, and that plenty of breast flesh was exposed."

"Breast flesh?"

"Yeah, lots of flesh, and it was breasty, and her nipples seemed erect under the robe. I'd never been alone with a woman who wore such a robe, and I'd never been alone with someone who was 7 or 8 years older than me. At least with so much breast flesh."

"What did you do?"

"I suggested that I should leave."

Pause.

"And she suggested that I should stay, that she had a question for me."

Head tilt.

"And while curling herself so that I began to wonder whether an actual nipple would slide out into the open, she asked me the difficult question. Did I mention that she was fairly tiny? Like, much smaller than Caroline, who was and is a tall, skinny Amazonian, or Kristen, who's average. Anyway, she wanted to know why I wasn't making the moves on her little sister."

Head tilt.

"I said that it seemed to me that maybe that was between Kristen and me, but then she went through her logic. She said that it didn't seem that I was religious, so it wasn't that I was against premarital sex, and she said that it didn't seem like I was gay."

"How'd she know that?"

"Doc, I continue to be amazed. I asked exactly that same question."

"And she said?"

"Well, she said that she'd noticed my big erection since we'd sat down on the couch, which kinda indicated to her that I wasn't homosexual."

"Uh huh."

"Or at least I like to remember that she said it was a big erection, but memory fogs, and it was almost 20 years ago. And maybe I was just thinking about when you said I had a big erection."

"I didn't exactly say that."

"Uh huh."

"And then what happened?"

"Well, as I've said, I'd been distracted by all that breast flesh, and also by just how small she was, and all that, but I do remember, exactly, her next question."

"Which was?"

"She asked when I'd started sleeping with Caroline."

"Really?"

"Well, she prefaced that question with her thought process. If I like her sister, and her sister's attractive, which she was and is. I mean, not freakishly attractive like Caroline, but certainly attractive. And if I'm not religious or gay, then I must have had some rationale to be spending so much time away from home, and so she decided I must be sleeping with my cousin."

Head tilt.

"Should we just move to the diary?"

"Maybe wrap up the evening with the sister. She has a name?"

"Yes, she does. Unlike my sunglasses."

"Uh huh."

"And I came clean with her."

"Oh?"

"I admitted that I did have a bit of a crush on Caroline, who wouldn't? And I then completely denied having any sort of sexual thing with Caroline, that it would be wrong, and neither of us would dream of such a thing. Plus, Caroline had a boyfriend who she loved and intended to marry."

"She had a boyfriend?"

"Oh, yes. Military guy. He'd been assigned to a nearby base, which is how they met. He'd soon been sent off to some other base. Sorry, I'm weak on lingo. I can say more, but that's going to take us afield."

"What happened that night?"

"After I'd proclaimed my innocence, Kristen's sister said she didn't believe me. She'd watched Caroline and me, and she could see the chemistry. She said she'd watched us when we thought we were alone, and she'd seen us brush hands and exchange looks. She said she knew what she knew."

"And?"

"And then she asked what I was doing."

Head nod.

"And I said that I was feeling her right nipple."

Pause.

"She said she could figure that out and added that she had not said it was okay to do so, and that she was married, and I should desist."

"Hmm."

"Okay, she wouldn't have used the word 'desist.' I don't think I've ever heard anyone use it, aside from maybe in an ironic way every decade or so. And that might have been one such instance, but I think the word comes up in the military, as in 'cease and desist' and maybe in a romance novel when some long-haired Adonis is pressing himself against a heaving bosom, and the woman flutters her eyes and moans in a southern accent, 'oh, sir, you must desist." Otherwise, that would just be a weird word choice. So, I don't know what she actually said, but she specifically didn't say 'cut it out' or 'fuck off,' and she didn't move away or slap my hand. She just sat there and implied I desist."

"What were you thinking?"

"Well, I've mulled over that question over the years and come up with two answers. The first is that I wasn't thinking, that I had been horny since getting ready to leave Kristen for the warm arms of Caroline, and the breastflesh was finally just too much. And this was 20 years ago. No one asked for permission to have sex. No one signed pre-intercourse contracts like they do now. Basically, as you know since you presumably dated during that era, the guy was expected to go for it until the girl said no with enough persuasiveness to mean business. Those were the days, filled with subtlety and miscommunication."

"The other answer?"

"What other answer?"

"Why else did you decide to feel her up?"

"Feel her up is also a phrase from back then. Do guys still feel up girls? Or has that been subsumed into 'hooking up'? I just don't know."

I looked at my psychiatrist, as if expecting an answer.

"Anyway, reason number two was much more important. I needed her to be quiet about Caroline. I thought she might not say anything to protect her sister's friend, but--then again--her sister was getting cheated on by that friend, and by her boyfriend, who'd only dated Kristen to gain access to her cousin. I could imagine this going in a couple of ways, but I had a bad feeling about it."

"So, what'd you do?"

"Well, I tugged harder on the nipple. I wasn't all that experienced, so I didn't know exactly what to do, but Grace's eyes narrowed when I squeezed her nipple, and so I twisted it and watched her face, watched her eyes shut, and her breathing change. All of which made me think our secret would be safe."

"How would you know that?"

"Some of this may have gotten added on later, but I do recall thinking, later that same night, as I was fucking her from behind, that it was a different kind of transgressive to be fucking..."

"David, language."

"...to be having sexual congress with an older, married woman. Now, of course, I'd laugh at myself for thinking of her as 'older.' She was all of 27. But as we had the intercourse thing going, and I was slamming away, I felt somewhat liberated. Partly because I didn't think of her as a fragile flower like I did Caroline."

"I don't think that you've described Caroline as a fragile flower, and I thought you said this other woman was tiny."

"Well, Caroline's tough in all sorts of ways, but I still thought of her as a kid, even if she was in the midst of what I used to call Caroline's anal period, kinda like Picasso's blue period. And in contrast to her current period of, I'm sorry for the language, uhm, the vigorously enthusiastic oral sex period."

"Uh huh."

"And I'll get to Grace, but to be clear, as I was wailing away, I was thinking, uhm... quick aside, did I mention she had such a narrow butt that I'd wondered whether her vagina would be big enough?"

"Are we getting somewhere?"

"Yes. We're getting, eventually, to the diary, which is where the action is. In the meantime, I was thinking about my strategy. Maybe it's tactics. I get them confused. Strategy/tactics, they're confusing."

"Doesn't matter. What were you thinking?"

"I was thinking that I was being ridiculous, that she'd been married a couple of years, and so of course she was big enough. Just another example of my misperceptions about women."

"I meant about the situation."

"Oh. Well, I'm wailing away. I'm sorry, is there a technical term for 'doggy style'?"

"It doesn't matter."

"Just trying to be polite. So I'm sliding in and out..."

"David, stop."

Pause.

"David, where'd you go?"

"Well, I went back to that night, into the details, but only in my head, because you asked me to stop, and in the me-too era, I try to follow requests."

She waved me on, like someone waving a car into a tight parking space.

"Brass tacks? I was thinking that if you have a Big Secret, and a 3d person finds out about the secret, then it's important that the secret be at least as important to the 3rd person as it is to the initial two. You need that 3rd person to really want to keep it secret, to NEED it to be secret. It can't just be out of politeness or the desire to protect someone else. Those things can change."

Eye squint.

"What I needed, and I think I knew as soon as I reached under her robe... did I mention it was this very satiny robe thing? That I could see the outline of her nipples, so I knew she wasn't wearing a bra? It was kinda like from one of those black and white movies from the '40's, and I felt a bit like Joel McCrae or somebody, except no one back then seems to have had sex. I mean, they must have since they had children, but it was more veiled in mystery and romance. I also had the thought that she'd put on her little outfit just for me, which was flattering."

"Uh huh."

"Though she later told me that it was for diagnostic purposes, that she put on that robe to see if I got an erection, to see if I was gay."

"Okay."

"I think I mentioned that she was married, and I knew that her husband had moved out temporarily, that he'd moved away for several months. He was setting up a business in Korea, an import-export business that (spoiler alert) has never thrived, but setting up the business allowed him to move temporarily to Seoul to think about their differences."

"Which were?"

"He didn't want kids. She wanted kids. It's one of those big stumbling blocks in marriages. Like money, or an odd number of people being gay."

"An odd number?"

"Yeah. You want either zero or two to be gay. You just don't want one. I don't know about thruples and all the other combos. Too complicated. I'm a simple man with simple tastes."

Clearing of throat.

"So just before I reached over to tweak a nipple, I thought about risk/benefit. Absolute worst case, she shrugs me off, but she's not going to scream or be terribly offended or report me. She's the one with all the breast flesh, and she invited me over, and I'm just a kid."

It's hard to read psychiatrists, but she looked at me with maternal affection, or so I'd like to think.

"But if she gave me any glint of a green light, then I figured we'd have sex, which seemed cool, because, a) I had--to quote her and my psychiatrist--a big erection, and it was needing to go somewhere, and she seemed like the kind of girl, I mean woman, who could talk and talk and talk about relationships for hours, and I was already talked out, and I had a sense that if I was direct, she'd respond. Worst case, she shrugs me off, and kicks me out of her house, and I get to go back to Caroline, and at least I'd get laid."

"So..."

"So, I tweaked the nipple, and it felt excellent, and I could tell--somehow--that she liked pain. I mean, Caroline was in her anal period, and I don't really like to imagine what that must feel like, but she doesn't seem to be in pain. Did I mention that even back then, she could reliably cum while getting vigorously..."

Hand raised.

"Did I mention that Caroline could reach orgasm, even as a teenager, while being on the receiving end of anal sex?"

I couldn't tell if that was eye rolling or a blink.

"Hmmm. I should move on, but it's fair to say that one of us was almost always rubbing Caroline's clitoris, off and on, and sometimes we'd also slide a dildo into her, uhm, vagina, mostly for her since I always felt it to be a little weird to bump against a disembodied, rock hard cock that was just on the other side of a beleaguered mucous membrane."

"Where's this going?"

"Quick question. You went to medical school, right?"

She nodded, appearing wary.

"If I say Caroline has been able to reliably reach orgasm during anal sex, but add the caveat that she also needs to have her clitoris rubbed, is it fair to shorthand that I'm able to fuck, I'm sorry, penetrate her into orgasm just with my big erection? Or is it more fair to say that she reached orgasm after what was usually quite a long period of tomfoolery, and that the orgasm was the natural result of her genitalia getting a lot of attention, and that the big penis in her rear was more of a prop that she put up with?"

A pale, impassive face looked back at me, and, being impassive, waited.

"I mean, how do you know? It's not like I'd go around bragging about it. Who am I going to tell, aside from my trained professional?"

"Why are you asking?"

"I ask, because she's generally on a bed when she has an orgasm, but I don't give the bed any credit whatsoever. I always chalk it down to my astonishing sexual technique."

Head tilt.

"Kidding."

"I think we've gone astray."

"Well, I know I have."

"Since you're now sleeping with her, maybe you could supply a name?"

"We didn't actually fall asleep together for another few weeks."

Clearing of throat.

"Grace. It's Grace. Anyway, so I'm squeezing a nipple... actually, I started off with just a modest pincer action. I wasn't really going for sexual response in the beginning. I was just trying to get a fingerhold, as it were, before sizing up next moves. For some reason, I felt confident about going straight to second base, which is a transgression in itself, right? But I was confident she'd have shot me down if I'd tried to kiss her, or if I'd gone south. I just had this sense that, while she might be surprised or at least act surprised, she'd let me grab hold of a nipple without objecting. And then moments later, when I squeezed, I just knew she liked some pain."

"Really, David, does this get back to this week?"

"Doc, you are amazing. I'm almost there, but I got sidetracked. So I have this sense that Grace likes pain. Not Spanish Inquisition pain, but brief, sharp pain, so I twist, and she moans. It's different with Caroline, who puts up with shenanigans from me that would probably send me to a psychiatric hospital--no offense. Kind of like when she gags herself on me. I think I'd find it mortifying to blow some dude, not to mention that I wouldn't want to look up and see some leering, sweaty, hairy guy looking at me, or feel his Neanderthal fingers gripping my head. Seriously not my thing. It would be traumatizing."