Kinkiest Request

I finally got my chance with this girl Kim, who was a lifeguard. She worked that same pool every summer from high school through college, and, like every other heterosexual male, I'd lusted for her for years. It was one of those summer relationships that was destined from the get-go to end in September. Oh, we liked one another, all right, had a good time together, but it was clear it was not going to be a long-term, lovey-dovey type of thing, as she was perhaps the most opinionated person I've ever known, and besides, we were both returning to our respective out-of-town universities in the Fall.

But when it came to her looks, everyone had the same opinion: One damn fine-looking gal, lithe and athletic, with short brown hair and brown eyes, tall and thin, with a huge white smile. She had very nice, super firm, super sensitive little breasts, and a perfect butt--her best asset.

Her skin was naturally light complexioned, very smooth and clear, so her dark tan contrasted dramatically with her white boobs and bottom, and she was always careful to keep the tan lines in exactly the same place. This was so important to her that she wore but one style of bikini, which she had in every color of the rainbow, with visors to match, that she wore every day at the pool.

Kim was decidedly outspoken about everything--politics, religion, sports, sex; you name it, and she held extremely strong opinions. Nixon should be executed. Catholics didn't get it. And the Dallas Cowboys could do no wrong. No brag, just fact, but it was surely my ability to coolly flex with her my-way-or-the-highway attitude that enabled me to be selected her summer boyfriend over the scores of more studly pool-jocks vying for her. Once she made up her mind who the lucky guy was—which took only about a week—she did not subscribe to that take-me-out-on-dates-and-I'll-let-you-go-a-little-further-each-time routine. No, she knew the summer was short and time's a wastin'.

So we fucked on our very first "date," which consisted of picking up some food at the Sonic and then following her directions to a secluded parking spot, where she promptly stripped herself and me and stuck her tongue down my throat. I really liked her what-are-we-waiting-on attitude about sex, but, though a pretty good lover, she lay towards the conservative end of the sexual behavior spectrum—at least at first. She gave good, though not great head (did not swallow), liked to have her pussy eaten (but could never quite cum from that), and liked to fuck in the missionary position. She had always been the Alpha Female—the leader, in charge—and so had never done anything that was someone else's idea. Since she was considered such a to-die-for prize and "put out," whatever guy she chose as her boyfriend wouldn't risk losing her for trying to persuade her to do something new.

I surmise that today she is probably either CEO of her own business or the dictator of some small, heavily armed, right-wing island republic. It was easy to picture her in fatigues with a .45. Ha!

Sex? Forget about cumming on her tits or face or spanking or bondage or anything like that. She had a particular aversion to anal sex, and would frequently mention how horrible she thought that was, even though I never tried it with her or even brought it up.

As far as fucking went, she was really good, but her pussy was a bit on the small side and moist but not real wet, so I wanted to fuck her doggie-style, as that position opens a woman up wider, and, of course, would give the best view of her best part, her fabulous butt.

I thought I'd never get her to do it doggie, though, and initially figured it was because of her extreme dislike of anal, as this position makes quite visible the anus, on the theory that if a man can see it, he'll want to fuck it.

Turns out, that wasn't the reason at all. You see, when I FINALLY got her to turn over, she was acting real coy. WhatTheFuckWasThatAbout? She knew she had a superb butt, so what was the source of her reluctance? Pimples. Yeah, pimples.

You see, because Kim was a lifeguard and had to get in and out of the water umpteen times a day, her swimsuit would, naturally, get wet. Since she sat in the lifeguard chair, the seat of her suit would stay wet. That's a formula for pimplia buttocksia.

Anyone who has ever spent much time in the water knows that this happens and just deals with it. Kim had otherwise flawless skin, so she was especially embarrassed about the occasional pimple on her bottom. I assured her that it was nothing to be concerned about, and that it did not bother me in the least.

By mid-summer, I'd used my soft-selling approach to coax her into doing new things: She learned to let herself cum when I'd eat her pussy. Using a fair-is-fair logic, she then agreed to try swallowing my ejaculate, only to surprisingly discover that she didn't mind at all the taste of semen. But, understandably, she wasn't through until she'd had a good, long dicking.

OK, so where's the kink? All right, all right, I'm getting there.

Gradually, she got over her embarrassment, way over her embarrassment, as you will see.

Well, after pool hours, we generally went back and got naked in the privacy of the girls' locker room there on the Astroturf floor. This one time in late July, before I could even shuck my trunks, Kim was already on all fours with her ass hiked up high in the air, back beautifully arched down, pussy pointing right at me, and looking back at me over her shoulder, exclaiming, "Hurry up!" I parted and kneaded her perfect ass cheeks, licked her gash good and wet, then sucked her clit hard before plunging my stiff rod inside and fondling those tiny taught tits, watching my cock go in and out her tight little pussy.

She'd gotten to where she actually preferred the doggie-style position, and I could certainly fuck her longer that way, with her pussy being wider open than missionary. Kim, however, no matter what the position, would never cum until I did, yet she would always climax just a second after I did. Not that there's anything wrong with that, but I prefer to bring a woman to orgasm at least once before I spew. The result was long—some of them extremely long—fucking sessions, not that that was a bit of a problem in itself.

So, I'm massaging that splendid butt while doing the old in-out, and I see that there's a big red pimple on it, right on her tan line. No big deal. She was over her embarrassing pimple phase; at least I thought she was. In fact my thumb was on it when she says, "I want you to pop that pimple."

Huh?

"I said I want you to pop that ugly zit on my butt. I can tell by the pressure, it's ripe for squeezing. I hate that feeling, and it's such a relief when it's popped. Keep fucking me--go just a little faster and deeper--then pop that pimple. You'll have to squeeze it really hard to pop it, so bear down as hard as you can. Don't worry about hurting me. I can take it. The important thing is to pop it."

Well, now, if I hadn't heard all. Chick wants me to pop the zit on her ass! Sonofabitch!!!

So I picked up the fucking pace a notch as she's watching me over her shoulder, her open mouth making "ooh, ooh, ooh" sounds with each thrust. I got that big old pimple between my right thumb and forefinger and squeezed hard.

She immediately responded by exuding more pussy juice and louder ooh-ooh-oohs. The extra lubrication was welcome, as her pussy was so tight I had to concentrate mightily to keep from cumming too quickly. I have very strong hands and was squeezing with considerable force, so I know it must have been painful, but the pimple held its own.

"Pop that big ol' ugly zit! Squeeze it out of me! Make my butt cute again!" she implored.

Now, when it comes to sex, I'll do about anything but extreme pain and degradation stuff, but this was downright weird. I mean, pimple-popping and lovemaking go together like ketchup on an orange. Yet I understood. I've had pimples before, and I know first-hand the sense of instant relief one has when they're popped, practically a feeling of achievement and victory. So, with mixed feelings, I continued.

I wiped my hands dry on a towel lying there, and got another grip on the pimple, this time with the thumb and index finger of both hands as I fucked her furiously fast and deep. I squeezed that zit with all my might. Still gazing at me over her shoulder, Kim pleaded, "Come on. You can do it. Pop that sonofabitch!"

Suddenly, I felt something give way, and out shot a volley of warm pus, like lava from a miniature volcano, right into my belly button! Gross, you say? Well, it's surprising how fast one will adjust his definition of "gross" when he is pounding in and out the mushrooming lips of a tight, wet pussy centered in the perfect ass of a screaming young, tan lifeguard!

Kim's pussy literally gushed with juice like it never had before, and the freakish sounds of orgasm emanating from her were not unlike a pack of wild African hyenas.

Then, still hanging onto that voided pimple, it now oozing a little blood, I came inside her convulsing pussy in wave after wave of orgasmic ecstasy, filling her with volumes of hot man juice. At long last I had discovered the, uh, shall we say, unique, key to her cumming before me.

My cock was still semi-hard a half hour later after we showered, dressed, and were leaving. Kim just kept saying over and over how good that sex was, how it was by far the best she'd ever had, and thanking me.

We had sex most days, and it was always good. However, about once every week or so, a zit on her butt would ripen, and we'd have another episode of profoundly pleasurable pimple-popping passion.

Lends a whole new meaning to the expression, "main squeeze."