Jan--The Good, The Bad & The Ugly


"Sure, but let's get this behemoth chest inside, first, OK?"

Though we were both strong, athletic guys, it took everything we had to get that sombitch up seven steps, through the tiny kitchen, down the narrow hall, and back into his bedroom. With sweat pouring down our faces, David popped a couple beers, and I twisted a bone. We sipped and smoked leisurely inside as David continued the Jan saga:

"From the liquor store, I took Jan to a party at the SAE house. She'd always wanted to go there, but I'd been able to keep her at bay with the story that minors weren't allowed because of all the drinking. So, now that she was of majority, it worked out perfectly. It was still a calculated risk, for some inebriated, loose-lipped brother could spill the beans about my sexual dalliances."

"But by then I was an officer—the treasurer—and the next-year fraternity president-designate, so I had the power to enforce a strict code of silence. This was a semi-formal mixer with Chi Omega, with which the SAE chapter on this campus had a special relationship.

"Chi Os, eh? I've banged a few of them," I tossed in.

Yeah, but the Chi Os at State were reputable girls a guy had to go steady with before they'd put out. Accordingly, I'd never been to bed with any of those sisters and so didn't have to worry about one of them leaking my unfaithfulness to Jan."

"Since they ran in a totally different circle from all the slutty chicks I'd fucked, they had no clue about that. In fact, they'd heard me talk about Jan and considered me the paragon of virtue. A dozen or so of our most respectable brothers were dating them."

"And so, in accordance with your master plan, this dressy party of somewhat older people would further make Jan feel 'grown up.' Clever, but let's get to the sex part," I prodded.

"Hold your horses, cowboy. The critical piece was for Jan to witness those nice, well-dressed, respectable brothers going up to their rooms with their nice, well-dressed, respectable steady girlfriends to have sex. Guys like me; girls like her. I wanted her to see first hand that such activity was perfectly normal."

"Later, when I took Jan upstairs to my room, I purposefully had a 'problem' with the lock on the door so we'd be stuck in the hall for several minutes. That guaranteed she could not help but hear what was obvious sexual activity going on behind the closed doors of rooms nearby."

"David, I appreciate all the details, but, dude, the anticipation is killing me!" I exclaimed, choking back a lung full of funny smoke and passing the number back to him.

He continued, "OK, OK, OK. I popped the cork on the last bottle of bubbly and sat her down on my bed for a serious heart-to-heart, saying, 'Honey, you're 18, a woman, and I'm 21, a man. I love you, and you love me. Normal men and women who love one another express it in many ways, an important one being sexual relations—that's why they call it making love. We're not making love, which is not normal. Now is the time to start being normal. Trust me, sweetheart, you're ready to make love.'"

"Then what?" I coughed.

"Well, she just sat there, atypically silent, but attentive. She had on a long, black velvet evening dress with a plunging v-neck; a strand of pearls and a matching pair of ear rings she'd borrowed from her mom; hair up; and black, patent leather high heel shoes. I'd never seen her—or any woman, for that matter—more beautiful. Passionately French-kissing her, I worked my way down her neck, slid the straps off her shoulders, stood her up to let the dress drop to the floor, then peeled her panties down to her ankles."

"While she didn't help, neither did she resist in the least. Oh my god! After four years, for the first time, I was seeing Jan totally naked! Those big, nice tits with the ideal down, out, and up swoop! Those dark, pointy mega-nipples! That perfect apple-shaped bottom! And what a pleasant surprise, an incredibly lippy pussy! She was a goddess."

"So, did you finally jump her bones?" I inquired.

"Not exactly 'jumped.' First, I used up a whole bottle of lotion massaging her body, both sides, head to foot. That accounted for at least an hour. Then I fondled and nibbled and sucked her boobs. She liked that—a lot—purring like a kitten while running her long slender fingers through my hair."

"It was hard to leave those tits, but the wonderful aroma of her pussy beckoned, so I eventually kissed my way south across her tiny waist to lick-suck that gigantic clit and slurp around on those huge, sopping-wet pussy lips. She loved it and, surprisingly, came right away, then came again when I introduced a couple fingers into her virgin-tight love tunnel."

"OK, David, did you fuck her or not?" I prompted, my jeans becoming uncomfortably tight.

"I'm getting there, sport. Swabbing my raging hard cock up and down between her extra-extra-large labia, I parked it at the entrance ramp to the ecstasy expressway. Wanting to make absolutely sure she was good to go because she was sort of semi-stiff-arming my hips, I looked her straight in the eyes and asked, 'Are you ready to make love, Jan?' With a simultaneously eager but reluctant look, she whispered, 'I'm really not sure, honey.'"

"Goddamn, David, what the hell did you do then?" I screamed, feeling his frustration.

"I had to make a decision, and quick. Back off, and I might regret it the rest of my life. Forge ahead, and she could freak out. Either way, it could be four years down the drain. So I took her by the wrists, held them down against the bed, and plunged in her pussy all the way to the hilt."

"'Oh, David, that feels so good, but I don't know, I just don't know,' she kept saying. It was like the old joke, 'Don't! Stop! Don't! Stop! Don't ...Stop! Don't stop!' but there was nothing funny about this situation. Fortunately, in just a few minutes, she got into it, I mean REALLY got into a rhythm with me, and orgasmed several times. For me, even after having visited pussyland with lots of college hotties, Jan was unquestionably the best ever."

"Wow, after all that time, you finally poked her. Thanks for sharing," I said, feeling nearly as exhausted as I would have had I been through all that myself.

"There's more. Amazingly, after all that reluctance and total lack of experience, she took to sex like a bird to air. Before the evening was over, I'd showed her everything in the book, and she quickly became expert at giving head, licking balls, titty-fucking, rimming, even anal, the whole nine yards." "

I came four times, first in her pussy, next between her boobs, then in her mouth—yes, for her very first blow-job she swallowed every drop of cum like it was nectar—and finally in her super-tight little butthole. The whole time, she kept saying, 'Oh, David, why didn't we do this years ago?' I chose to ignore that question, as the plain and simple answer was because she'd always said, 'I'm just not ready yet,' and I was the patient-as-Job boyfriend."

"And that's the BAD component?" I asked, somewhat confused.

"Well, in a way, yes, because even in the ensuing nine years of dating and thousands of fucks, she never has gotten over her sexual hang-up. You see, every time we did it, EVERY TIME, it was like starting from point zero again: lots of drinks, the long message, hours of foreplay."

"Then, when it came down to the old dick-in-the-hole, she'd start that I-don't-know routine, so I'd hold her down, fuck her silly, and she'd suddenly bloom into an uninhibited sexual tigress once again. It's the damnedest thing."

"How strange. So, you've covered the good--that she's an exceptional lover--and the bad---that she's still always reticent at first--but where does the ugly figure in?" I wondered.

"The booze and drugs. Her mom had a full bar and a medicine cabinet overflowing with get-fucked-up pills. The completely unsupervised Jan started sampling the stuff in her early teens, about the time I started dating her. Said she learned which drugs to take from Health class at school—ha! No big deal; most of our generation experimented with drugs."

"By the time she was in the 11th grade, though, when I was a sophomore in college and only saw her about once a week, she'd developed a substance-abuse problem I didn't realize was so serious. Then, when I graduated and moved in with her, I discovered that she was a real addict."

"Jan has what amounts to an in-house liquor store and veritable home pharmacy of every kind of prescription anti-anxiety, pain, sedative, sleep aid, and muscle-relaxant pill manufactured—all prescribed and legal. She doesn't smoke dope, though, because it's not!"

"Ugly, for sure" I said.

David wrapped up, "I'm giving you fair warning, my friend: proceed with caution. Jan is seriously addicted to alcohol and narcotics. We were going to get married, but because she doesn't think she even has a problem and refuses to get help, I broke up with her after an astounding thirteen years together."

"I wouldn't have gone splitsky unless I thought it thoroughly through, and though we're still friends, I've moved on. Jan's an essentially sweet girl, a fantastic if perennially reluctant lover, but she's a real mess, man."

And with that, David cranked the mint Chevelle to burbling life. I hopped in, he put the pedal to the metal, and we made the trip from our street to Russell and Vickie's in record time.

David rumbled off, and I stood there on the sidewalk pondering what to do. OK, I had the complete scoop on Jan. She was a great-looking gal, friendly and extroverted, sweet and tasteful, with a good job, easy to talk to, superb in the sack, but a train wreck. Good judgement said avoid her, but it would be impossible to forget about her because there she was 30 yards from my best friends, twisting her fine self to and fro every day. And I was horny.

As usual, horniness trumped good judgement. I told my friends I was going to beg off for the evening and spend it with Jan, instead. Screwing up my courage, I stomped across the street and knocked on her front door.

"Hey, what a pleasant surprise! Come on in. That was really nice of you to help David with the big chest."

It was HER big chest that I wanted to help, I thought, my eyes darting back and forth between nipples. Then her pretty, smiling face. Then that very large mouth with its full lips. Then that slim but fleshy bottom. Then those slender, mile-long legs. Then her thick, shiny brown hair. Damn, she was so fine, the whole package. If I followed David's playbook just right, I would fuck Jan that very night, I resolved.

"Jan, would you like to go out for that 'drink or five' tonight?"

"Oh, you're such a dear, but no thanks. I'm feeling real stay-at-home tonight. But I'd love your company, so, please, have a seat and make yourself at home," she invited.

She lit a cigarette and disappeared into the kitchen. "I'm drinking Vodka gimlets...over Valium and Percoset—doctor's orders, hee-hee. What a perfect combo! What'll you have?" she asked, obviously well ahead of me.

"Same drink, hold the pharmaceuticals. Mind if I roll a doobie?" I said, being as forthcoming about my drug of choice as she was of hers.

"No prob. Only I don't smoke pot. My doctors wouldn't like that. By the way, I couldn't let you have Vals or Percs even if you did want them. You have to have a physician's prescription for those," she explained over the clink-clink of ice.

Making quick judgements, I analyzed her words. "Doctors,"—plural. How many docs did she have? "Vals" and "Percs?" Did she have pet names for all her beloved drugs?

"What's your doc's name? Mine's Maria Wanna, a bit green, but she's good-looking—nice large buds and slender stems," I kidded, hoping Jan both got the corny joke and made the connection with her own big boobs and slim legs.

Reappearing with a huge glass in each hand, she didn't "get" the joke until I explained it to her, but then she broke up in genuine laughter, saying, "Ha-ha-ha—that is fun-NEE! I like a guy with a sense of humor. Sounds like you like girls with big breasts and skinny legs?"

"Absolutely. Let's see, who around here has those features?" I teased as she sat down beside me on the couch.

Obviously, things were off to a great start and got even better. Over the next few hours, we drank and talked and smoked our respective leaf of choice and got ever cozier until we were kissing and groping like teenagers on prom night.

That brings the timeline up to where I left the story in the beginning: Jan nude on the floor with my cock in her hand, having just given me awesome head, telling me she wasn't positive she wanted to go any further. Just like David said, she was vacillating when the moment of erect-penis-in-wet-vagina arrived. This was Jan's "bad" on the UCEGBUS, the Universal Clint Eastwood Good Bad Ugly Scale.

Now, according to David's play book, at this point, I should get on top of her, pin her arms to the floor, and screw the holy shit out of her. And that's what I'd intended to do until that moment actually arrived.

You see, there is an ethical compass deep within me that points at forcing sex on a girl as WRONG. Unless a girl gives you a verbal go-ahead or physically guides you inside her, she's not indicating it's OK. Jan was doing neither, yet she wasn't saying "no," either.

In fact, her "I'm not positive I want to go any further," and "We dated for years before I let David make love with me" bit and neither pulling me in nor pushing me away was essentially meaningless—for me, the GUY, that is.

On the other hand, for Jan, it was her way of transferring The Intercourse Decision from her to the guy and therefore absolving herself of all moral responsibility while enjoying every bit of the pleasure should he decide to screw her.

Realizing this, it's enough to make a man angry enough to, well, pin her arms down and fuck her silly.

So, I did.

At first, lying flat of her back spread eagle, she froze and just stared straight up into my eyes with a blank expression as I slowly pumped her warm, wet pussy. In two minutes, she was beginning to relax, move a bit, and make soft pleasure whimpers. In another three, eyes trained like lasers on mine, she was rocking her hips stroke for stroke with me, mouthing a rhythmic "yeah, yeah, yeah," and her pussy was fever-hot.

I had to look away from her eyes, though, because her grapefruit-size boobs were sloshing so beautifully up and down. I realized that if I altered my fuck on the in-stroke just a bit to the left, then withdrew it slightly to the right, it made her titties gyrate in a clockwise circle. Reverse the stroke, and they started going around and around counterclockwise. How wonderful!

As I've always said, "Big tits do not an attractive girl make." It's their overall shape, consistency, where they're situated on the chest, how they coordinate with the rest of her body, and how they "behave" when in motion. But in Jan's case, her ta-tas were very big AND perfectly shaped AND extremely well-behaved.

I had to gather them up, squeeze them together, and nibble-suck those rubbery, finger-tip size nipples—left one, right one, left one, right one. I squeezed them forcefully together and got both nips in my mouth at the same time. Slurp, slurp, slurp, slurp.

Then Jan shuddered, her skin flushed all over, and she came with a long "oooooooooooooo, thaaaaaaaaat's soooooooooooo gooooooooood," lips half open, back arched, fingernails dug into to the carpet. Isn't it wonderful when there's no doubt whatsoever that you made the girl you're making love to orgasm?

The waist is an often-overlooked erogenous zone, and Jan's was simply divine. The first thing you noticed was how tiny it was, remarkable in itself but all the more so given that she was a 5'10" 125- to 130-pound woman. I don't know what it measured, and, yes, I do have large hands, but I could compress them around her midriff and actually touch my thumbs and middle fingers together. Amazing!

Centered in it was a wide, "outie" belly button she just loved me to kiss and tongue. Of course, that her waist was so slim just made her already generous boobs seem even bigger.

If you're a leg-man, Jan's would have you shouting "hallelujah." A yard long and satin-smooth, her legs were like a ballet dancer's, downright skinny, yet not bony or knob-kneed. Creamy soft thighs connected to muscular, elongated calves. Narrow, dramatically arched size 10 feet terminated in long, fingerlike toes. She enjoyed me messaging and sucking them. I enjoyed how she could use them with hand-like dexterity to jack my cock.

Feeling suddenly deprived of her ass, I asked, "You like to do it doggie-style, Jan?"

"If it's sex, I like it, period! I'll do anything any way you like," she said with her usual enthusiasm, turning over to get on all fours and hike her butt up high.

Ass-men, pay attention, because Jan's was fantastic, in a most unusual way.

As soon as I saw her bottom from this angle, the term "pillow-top" came to mind. It's a term mattress manufactures use to describe a certain type of high-end bedding that features a thin but lofty pad attached to the top of the mattress itself.

Jan's buns were constructed just like that—an extra layer of cushy butt flesh atop the musculature below, with a defined, visible "seam" in between when she tightened her derriere muscles. So you get the benefit of both a pad of soft, jiggley stuff as well as the firm butt flesh on which it rides.

I sank my hands into those buns, peeled them apart, swabbed my cock between her prodigious pussy lips, and plunged it into the sopping, warm wetness. Because they felt so good, it was a while before I let go of her buns, but when I did, their unique make-up was a visual delight:

Every time my hips would contact them on the in-stroke, the flesh would ripple in a forward-and-back wave. Getting in the right rhythm kept them in constant motion, just like her big boobs, swaying like bell clappers, their pronounced nipples kissing the carpet fuzz.

"Look, ma, no hands!" I shouted.

Despite the corny expression, she laughed anyway.

"Uh, uh, uh," Jan moaned with each stroke, occasionally looking back over her shoulder at me with a sexed-up half-smile.

I gave each bun a spank, and when she responded by fucking back more vigorously, I smacked them again, harder, then again harder still. She liked that—a lot—so I kept it up, making them rosy red and her pussy even wetter.

Good thing, too, for I was about to cum, and the extra lube enabled me to bang her for another twenty minutes or so. Even though she'd had a bunch of mini-orgasms, when I reached around to seize those wonderful orbs, the meaty sensation along with erect nipples boring into my palms sent me over the edge, and I blasted over and over and over into her.

As soon as I did, that must have taken Jan to the next level, too, as she shuddered with an ear-piercing climactic scream, fucking back in a furiously fast blur and milking every last drop of man-milk out of me until we gradually wound down to panting stillness. Un-fucking-believable!

The male refractory period—when he's just ejaculated but is not yet ready to go again—is perhaps the only time in which a man can assess a woman truly objectively. So, that's precisely what I did with respect to Jan right after our first fuck.

David said she was 27, but she looked about five years older. The booze, pills and three-pack-a-day habit had taken their toll: In the light of the 150-watt ceiling fixture, her fair skin was absent a healthy glow, the tiny "crow's feet" around her eyes were a few years premature, her teeth were a shade below bright white, and the taughtness of her body was a tad less than you'd expect for a woman in her late 20s.

Nevertheless, Jan still looked great, a solid 9 on the old 1-to-10 scale, but not quite the beauty I'm sure she once was—or could have still been had she not had the drug and alcohol problem.

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