Lifeguard at the Reflecting Pool

At the end of my junior year I felt I had to take a personal inventory. It went: Looks -- average. Actually, who knows; it's hard to be objective. Athletics -- average, definitely. Brains -- much better than average, as long as you count only nerd smarts. Assets -- well, no debt (my parents were both successful professionals), and I had a cool old British sports car, which cost less to buy than maintain.

Personality -- Maybe non-existent.

Actually, that was too harsh. On the one hand, I liked me. I was self-aware and I thought I was even pretty funny. I could get along well with most people, at least for a while.

But on the other hand, I had some deficits, and they were big ones. I had always been introverted. I had all the symptoms. I could handle small talk one-on-one for about ten minutes and a party for maybe an hour. And so I was low in social confidence. Deservedly so, since there's nothing more embarrassing than that silence when you run out of things to say. In particular I had a tough time with extroverts. Well, I liked extroverts individually, because after all, what do two introverts talk about? But with more than a few, they start blabbing and pretty soon it's a dance party.

That explained my current dry spell between girlfriends. Keeping them interested was hard enough. Meeting them was almost impossible. I decided I had better do something about it before I ended up a monk in a cave.

I didn't really know what to do about a trait that seemed to be inborn, but phobias are treated by de-sensitization through gradual exposure. So instead of interning at an investment bank, I took a summer job as a lifeguard at a private club. I'd meet lots of people and have lots of time to talk.

****

The club was in a famous old coastal resort town. It was a place where people didn't have second homes so much as second mansions. Most had been built in the 1890's, when everyone had servants. My guess was that nine-figure portfolios were common.

The wealthy families would come for the whole summer. The spouses and younger kids stayed for months, but the plutocrats and their young adults would drop by only briefly, while they weren't working at a hedge fund or whatever. So since I don't date thirteen year olds, I was faced with a rotating cast of entitled young women in $300 bikinis who would be around for a week at the most. They seemed like tough targets.

Other potential opportunities were the au pairs who were brought along to watch the younger kids. And the junior lifeguard, of course.

The junior lifeguard, Jenny, was, unfortunately, a tall, slender, and unapproachably beautiful blond who didn't strike me as having much personality anyway. Think Baywatch but with smaller boobs and longer legs. We always opened and closed the pool together and we got along well as a working team, but at other times she was disinterested and aloof. Anyway, she was constantly surrounded by a phalanx of wealthy young suitors.

The au pairs, on the other hand, had potential. They were here all summer, they were mostly young and earnest, and they were looking for friends in this strange land. The question was how to approach them. The answer, frequently, was swimming and diving lessons for their charges.

I was fine with them while we had their kids' swimming as a project, but then I would have to find a way to extend the conversation. I'd ask them all about themselves, their employers, their kids. That would work for a while, but then it got creepy.

Eventually I found one who seemed happy to do most of the talking. She was not overly beautiful, but she was shapely, chatty, and clearly not wealthy, which was a relief. We had a nice conversation one day, after the lessons. She did the talking, of course. I mostly kept stealing glances at the substantial bulges under her tee shirt. She may have noticed. When she had to take the kids back home, I said how nice it had been talking to her and asked when she would be back. Bold! But the kids were squalling and all she could spare was a harried wave goodbye. Still, I went home on a kind of optimistic high.

The next day I pathetically wore my coolest tee shirt. She didn't show up.

Nor the next day. I spent both days admiring the scenery around the pool. Some of those rich girls were really hot. Too bad there was a dress code.

She finally showed up the afternoon of the third day, kids in tow. She came right over, pulled up a chair and sat down next to me! Her name was Sheila. She watched the shallow end with me, but probably only because her kids were there.

And she talked. I marveled at how she never ran out of things to say. Apparently some peoples' brains just spout conversation like a lawn sprinkler. I envied the ability and resented not having it. Unfortunately, after the first few minutes her chatter was less interesting than my own thoughts. Staying out of my own head became effortful and, eventually, stressful. I worried I wouldn't be able to keep track of her ramblings. But at one point she reached over and put her fingertips on my thigh to emphasize a point, and concentrating got easier.

Jenny was meant to be watching the deep end, but she was surrounded by the usual wall of studly young fellows. They were showing off their best funny dives for her. Being the only one really watching, I couldn't leave the pool. Sheila offered to get me lunch from the snack bar. She returned with a sandwich and asked me for $10.16, returning nine cents change from my quarter.

She seemed more businesslike than empathic or romantic. But she did seem bold and confident. She had short, close cropped hair which, I thought, was strangely sexy with her big boobs. It said that she didn't need long hair to advertise her femininity.

****

The next day she showed up alone, later in the afternoon, and again came straight over to talk. She cross-examined me about my parents, our house, our hobbies, my college and my career interests. I felt like I was filling out a résumé. She seemed impressed by my academics. She stayed until closing.

Promptly at closing time, while Sheila and I were still chatting (or listening), Jenny came over. Silhouetted against the late afternoon sun, her tangled blond mane looked like a halo. Really, it was better when you couldn't see her face, because once you did it was impossible to look away. She asked, in her usual soft voice, whether I would close up for her; she had to leave. So logically I said of course. I'm a doormat, and girls like Jenny were made to walk on me. She was led off by a beautifully coiffed young man with a movie star profile, as was often the case.

When I had finally managed to get all the kids out of the water, Sheila said she wanted to take one quick dip. She took off her shirt and dropped her shorts.

I was in charge of dress code enforcement. Her bikini didn't meet the standard. For one thing, it was a thong. For another, the top was microscopic and precarious. She had huge boobs but it seemed to rely on just her nipples to stay located. She quickly dove in, flashing her ass at me. She repositioned her top as she resurfaced, but not before I could see her boobs floating free underwater. She smiled at me with an inside-joke grin.

I wasn't in enforcement mode, apparently, because I did nothing but get slightly stiff.

She hauled herself out right in front of me, giving me a long look at her big, shiny wet boobs expanded by gravity. Then she grabbed a towel, stood slightly inside my personal space, and shook her whole body while she vigorously toweled off her hair.

I was stunned. This was a good sign, probably. She might be signaling me, but I couldn't believe it. Me? And even if she was, what then? I didn't want to make a mistake and embarrass myself. I wouldn't sleep for days and I'd be cringing for weeks.

So she asked me what day I was off. I said Monday, and she said, "Let's do something!" We exchanged phone numbers.

It seems so easy when other people do it.

****

I spent a lot of time planning some options for Monday. A cruise in the hills in my cool car. A hike. A picnic. Drinks by the ocean. Conversation topics, of course.

She texted to say she couldn't get the day off. Her employers were firm that she was off Sundays and they had planned their summer accordingly. But she said she got off work at 8, when the kids went to bed.

Thank god for texting. I had time to think. I asked whether she wanted to go for a twilight picnic in my old car. She did. I arranged to pick her up at 8:15 the next night.

Jenny helped me close the pool, and in fact, she started without me and did most of the work. She was polite but reserved, as usual. Between the two of us there was never much conversation, which used to make me tense before I got used to it. She obviously didn't have much to discuss with me beyond pool maintenance, and I really didn't expect to pique her interest.

****

It was a warm summer evening with a late sunset. I rolled up to Sheila's mansion with the top down. She jumped in wearing a sleeveless top and tight jeans.

She asked about the car. I said it was great if you didn't mind expensive repairs and a total lack of safety gear. She asked lots of questions about the cost of parts, service and insurance and then asked why I didn't get something newer. She said modern Porches were faster.

Since it was so late I had brought some take-out and wine. We drove to a scenic view area with picnic tables and had dinner. The sun was already setting as we arrived, but the following golden hour was spectacular. She buzzed away about this and that, things I can't possibly remember now. I finally relaxed about filling awkward silences. There was none.

It got cool, and we returned to the car. I put the top up. She said that the picnic had been really nice and she'd had a great time. And then, after looking meaningfully into my eyes, she leaned across the transmission tunnel with her eyes closed, lips leading the way.

This was ideal. She was taking the risk, which in my case was zero. I kissed her. She responded by opening her lips. I put a hand on her waist and held it gently. She put a hand high on my thigh. Aided by half a bottle of wine, I started to move my hand upward. There was no resistance and, in fact, the kissing intensified. Finally I ran my fingertips along the large underside of her boob.

This was nice, but the transmission tunnel would keep us from going any further. I thought. Then she said, "Your place or mine?" and my adrenaline redlined.

We both roomed in the disused servants' quarters of a mansion. My room was a pigsty, though, so we went to her place. To be discreet she had me park my car a hundred yards down the road. Then she led me quickly up the dark, winding driveway and through the separate servants' entrance.

This was going head-spinningly fast. I wondered whether we were going to fall through the door and fuck on the floor. But no. We entered a miniature living room with a kitchenette, and a very self-possessed Sheila matter-of-factly locked the outside door and the door to the main house, pulled a bottle of wine from the mini-fridge, and filled two wine glasses that were already standing on the counter. She gave me one and plunked herself down on the love seat, which I hoped was aptly named.

I sat and put one arm behind her, on the back of the couch. She put a hand on my thigh again and took a sip of wine. "This place looks nice but it's terrible," she said after minimal preliminaries. "My employers are remote and the kids are entitled, and they're all snooty. I'm an appliance here."

"You're a beautiful appliance though," I said. It was the wine talking.

"I may not look like your buddy Jenny," she said grimly, "but I do have some redeeming features." She twisted toward me and smashed one redeeming feature against my arm. "And I'm probably a better fuck than she is."

"I have nothing going with Jenny," I protested. "Never have, never will. We barely speak. You're the one for me." Wow, was I getting carried away.

She regarded me suspiciously. "Really? You're just her type, you know? She's really smart."

"Honestly," I said. "There's nothing there. How can I convince you?"

"You can convince me by being a little more into me," she said slightly harshly. She leaned forward and began to take off her sandals. Suddenly this seemed like it was going to be some sort of competition. I pulled her back into the couch, leaned in and kissed her hard. She still seemed lukewarm.

"I have to get the kids up early tomorrow for riding lessons," she said. "Why don't we take off these clothes?" She stood and commenced to strip.

I was torn between being attracted (my lower half) and repelled (my upper half). The chemistry was fading but the physical attraction accelerated fast as her large boobs bounced out of her lacy bra. She started tugging down her thong. I figured I'd better sort out the fine points later.

I was still shuffling with my pants around my ankles as she led me to her bedroom. She turned toward me and closed. It was hard to say whether the first point of contact was her tits or my cock, which was now straight out, but soon both were squashed in an asphyxiating full-body suck-face. I advanced one thigh and she straddled and humped it while I palmed a boob. We both semi-fell on the bed and I finally managed to kick off my pants. She wiggled her way underneath me and reached down for my cock. I was still hot for her boobs, so I was rigid and she had no problem sliding me into her and pulling me up so that I was out of kissing range but in a good place to fuck her. Which I did, for lack of alternative, keeping one hand on a tremendous boob. She began to make little noises.

We were both deprived and horny, so it didn't take long for the squishy sounds to start. The antique bed was squeaking and banging against the wall, and Sheila started moaning "fuck, fuck, fuck...." I felt the familiar tidal wave building. I groaned, "Incoming!" She redoubled her humping, and I came deep inside her.

I continued humping lightly and stroking the side of her ribs, but she seemed to feel the evening was over. She reached up for a perfunctory kiss and rolled me off. She said with a smile, "Thanks, I needed that. You're a good lifeguard."

I was glad she was happy, in her way. But now I felt like an appliance.

****

She had me leave quietly so that her employers wouldn't think she was "running a cathouse." I snuck down the driveway and drove home as silently as my car would allow. I was thrilled and depressed that I had fucked her on our first date and it had cost me only three hours and some fast food.

****

At least it was easy to be on time for work the next morning. To my surprise Jenny was already unfurling umbrellas. I said "hi" as usual and she gave me a "hi" back in her usual diffident way. I asked how her evening had been and she said "OK," as usual, but this time I detected a little annoyance. I ventured, "Your guy looked pretty hot yesterday."

She kept working, but I thought I could feel a silent eye-roll.

"Didn't work out?" I felt like hearing someone else had relationship problems.

She finally stopped long enough to sit on the edge of a chaise and stare at me angrily. She was pissed. "These people here. They think they are so desirable because they are rich. And smart. And good looking."

Sounded logical. I said, "But...?"

"They don't realize that even though I'm not working a desk, I'm not culturally deprived. I didn't grow up in poverty. None of them goes go to a better college than me. And they still think I'll screw them for the entire week they're here. That guy bought me a drive-through cheeseburger last night and talked about nothing, zero, nada, and then wanted me to blow him in his car. It was humiliating even being asked. And if I went with him again tonight, the understanding would be that he'll do me for sure. I am not a vacation sex doll!"

Now she had me thinking about me and Sheila.

"So don't go with him..." I suggested.

"Of course not. But there's an endless supply of these entitled meatheads here and they all rotate through in a week. At least you can work the au pair circuit." She sounded bitter. "Let me know when you find a guy au pair!"

She had the cutest frown.

I told her I was sorry but that I was sure a good guy would come along soon.

"I've been combing through the candidates," she said, "without success. It's exhausting. And it's not my style. As you may have noticed."

I wasn't sure I agreed. She had all the equipment to take down any guy she wanted.

****

I didn't know what to expect from Sheila. Maybe I had disrespected her. Maybe I was an entitled meathead. Maybe she just wasn't into affection. But she showed up the next afternoon even though it looked like rain and her charges were reluctant to swim. She again pulled up a chair next to mine and started talking.

After a while I mentioned that I hoped she had a nice time last night. She said yes, without elaboration. With a carefully planned line, I said I hoped I hadn't pushed things too fast for her. She looked faintly amused and said, "Don't worry about me. What are you doing tonight?" So I left it at that and we planned another 8:15 pickup.

She again bought me lunch at the snack bar and asked for $7.29 as reimbursement. And she resumed chatting.

Her chattiness still relieved my concerns about running out of conversation, which was relaxing. The few silences we had were far between, and she would fill the void or do something with the kids after only a minute or two. But it was beginning to be like white noise. I couldn't recall what she had said even five minutes ago. It was cheery and friendly and energetic and probably entirely normal, but it was harder and harder to pay attention. She seemed interested in things other people had said or done to each other that would affect no one but themselves. I assumed most normally extroverted, "people-people" were more socially attuned and would be interested. But I wasn't. So I tried to launch some more abstract topics, and they went nowhere.

Nevertheless, she hung around until closing, brushed a boob up against me, and confirmed our date as she said goodbye. Only Jenny was still around, so I put a hand on the small of her back and kissed her as I walked her out.

****

It was up to me to plan the evening, so I found a restaurant that stayed open late. Since she wanted confidentiality, I parked on the street outside her mansion and texted to say that her chariot was waiting. She trotted down the long driveway through the misty rain, jumped in, and slammed the door so hard I thought it would fall off. But we made it to the restaurant, and as we sat I discovered that under her rain jacket she was wearing only a translucent white top. It was stretched tight over two darker spots beneath, and stress ridges in the material ran between them. I thought of tensor vectors.

The service was slow and I enjoyed the view at length. I think she was consciously flaunting her boobs at me, which was hot. But as time went by she got antsy and I got the sense we were on the clock. She suggested we skip dessert and coffee and "get on with it." Maybe that was flattering.

So once again we piled into my car and drove to her place. But this time we charged straight into her immaculate bedroom, disrobed and fucked in one smooth motion. She got on top because, she said, she knew guys liked to watch her tits. I was out again in less than 30 minutes.

Driving home, I decided I would never forget her riding me, swinging those big boobs in my face. But then I thought it was time to reflect again. Despite my inward-looking personality, I had a girl. That was good. "Girlfriend" might be too strong, but she made me feel less lonely and somewhat appreciated, which was nice. She liked quick sex with no entanglements, which is every young man's dream, right? Except mine, apparently. Which was bad.