Quintuple Virginities

Janet and Phyllis had been friends for over forty years now. Through junior and senior high schools, college. "Going away to college" meant family support to live in "dorm independence" on the local campus: four years of rooming together, sharing joys and triumphs and problems.

Post college, their lives ran on similar, largely parallel tracks. Marriage: Janet's first had lasted twenty years and yielded one kid. Her next two marriages were ill-advised and mercifully short. She was currently single. Phyllis was still married to her first: they'd produced three kids, all grown. Similar interests and studies had led the women to similar masters' degrees and careers: five years ago they'd found themselves working for the same big aerospace company, but in different cities and divisions.

The jobs had brought them together in this pricy hotel: a four-day technical conference to which each had been sent independently. Janet had access to the overall list of company attendees, spotted Phyllis's name, called her: they pooled resources and got a deluxe suite together for less than two singles.

They arrived yesterday: today had been the first conference day. Last night was spent catching up -- they'd not spent any significant time actually together, face-to-face, in well over thirty years, and their considerable correspondence hadn't really filled the bill on keeping up to date.

They were still utterly compatible, exchanged intimate confidences easily, eagerly. Kids, husbands, work -- commiseration, admiration, secret self-evaluations. Jobs? Both were senior technical staff, rising steadily, and happy.

Personal life -- meaning of course sex-life? Janet admitted to her mistakes -- all three hubbies as errors of judgment: when pressed, she admitted that yes, there had been lovers, quite a few both during and outside the marriages.

Phyllis had to ask, was she still in touch with Jerry, Janet's first extramarital? Phyllis knew he'd appeared on the scene less than a year into that marriage, that he and Janet had cycled in and out of one another's lives multiple times, that Janet was hopelessly and permanently in lust for him, and apparently he for her as well, a nice match. In fact, some years back she'd even seen photos of him and Janet (some of them quite explicit), and could understand the physical attraction completely.

No, Janet told her a little dreamy-eyed, she hadn't seen Jerry for over five years, but would gladly do so on any excuse whatever. If only! Maybe she should re-initiate things? Phyllis's husband had been a dud sexually: no sex-life at all for the past several years, no lovers -- she was too chicken, she said, although thought it a good idea in the abstract. She made do with a vibrator and daydreams, and lots of 'good works' activities. Sublimation didn't have to be unconscious, did it?

The hotel had a fine restaurant: they had just ordered and settled into more conversation and a bottle of merlot when Phyllis goggled at something behind Janet's shoulder, sputtered, and finally managed "Janet! Don't turn around, but a man just walked in and sat down about three tables away and I swear, absolutely SWEAR, he's your Jerry... but without the full beard. My god, Jerry has a twin! And he's looking at us pretty hard. Now he's studying the menu. Go easy, turn and take a look."

The man lifted his head at exactly that moment, as if on cue, stared straight at Janet, did a perfect double-take, grinned broadly and stood up. Janet squealed -- it was indeed her Jerry! He joined them at once and seemed extraordinarily pleased to meet Phyllis. He was, in fact, quite taken with her: although he was careful to lavish most of his attention on Janet, the more than adequate portion allotted to Phyllis made her quite happy. Plus there was this subtle male aura around him. Pheromones, perhaps? Anyhow, he was most attractive.

Dinner lasted until nine: it didn't take long for Phyllis to understand why the Jerry-Janet thing had gone on practically forever, and it certainly boded to re-erupt right here and now -- the obvious looks the two exchanged were completely transparent! The conversation ranged all over the place, always fast, intellectual and fun. The later it got, the more familiar she became with this man, the better she understood Janet's attraction to him -- and envied her. At nine, they all admitted that perhaps they'd worn out the restaurant's welcome. Jerry stood, said they would have to meet for dinner again, maybe breakfast also, he'd give them a call early AM.

Phyllis's belly did little flip-flops as Jerry and Janet clinched. From within the clinch he whispered something longish into her ear, she looked at him coyly and nodded agreement. Then he was gone.

Back in the room, Phyllis looked at Janet and let her envy show. "So THAT'S your long-term lust-bunny! I approve! He's luscious. But what was it you two were planning there at the end? Right after that incredible PDA? I was expecting you to just drop to the floor right there, maybe do a rabbit-fuck or something!"

Janet blushed, giggled, and then looked somewhat apologetic. "He's going to come here to the room and get me at eleven sharp. That is, eleven tonight. Sorry."

Phyllis grinned and threw a pillow at Janet's head, muttering "The only thing you're sorry about is that it's been so many years and now you have to wait two more hours! Can't fool THIS girl! I'm so jealous I could just curl up and die. What are we going to do while YOU wait for YOUR tryst to arrive? I guess I'll just stay here in my lonely room, like in the old song!"

"Well, Lady Phyllis, I have some definite prep work to do -- but two hours is plenty of time. I know this man's tastes and talents very well. He happens to be the best eater of pussy that anyone's god ever created, and he likes it absolutely hairless -- and I agree. Shaving exposes nerves you can't even imagine! So I'm going to shave myself squeaky-clean, totally smooth, right NOW."

She sighed, then grinned: "Jerry gave me my very first pussy-shave, you know. He's a genuine expert. And he's a positive fanatic about anal, he's just superb at it, all loving and careful and STRONG. Best of all, he's never in the slightest hurry, not for pussy, or oral, or anal. He can make me come a dozen times each way before he needs to come himself, and so I'm going to give myself a little enema in anticipation. Because he's going to want into my bottom almost immediately -- I KNOW this man! - and I'm not going to deny him or myself that pleasure!"

Phyllis looked both astounded and vaguely disgruntled. Janet studied her for a very, very long moment, then finally said quietly "Phyllis, have you ever done a trio? A threesome? Of any sort? Two men and a woman, two women and a man? Or maybe even three women?"

Phyllis reddened, shook her head: No, she hadn't -- and had Janet?

Janet admitted to "never" -- but she'd often wondered... had even discussed it with Jerry years ago. But no, nothing had ever materialized. Fantasy-ville.

Janet kept right on - "Phyllis, I may be a bit nutty about lots of things, but now I'm going to be perfectly serious, so just listen to me for a second, okay?" Phyllis nodded. The suggestion seemed to explode out of nowhere. "You should join us. When he arrives at eleven, we -- you and I - can sandbag him with something special: he can just come in and stay for a while. Preferably a long while! He's fully capable of handling two of us and I'm sure he'd love it. His tongue never wears out, and his cock -- well, let's just say it should be on a horny sixteen-year-old, talk about resurrection capacity! It'd be something new and special for us all!"

After a moment's recovery from initial shock, Phyllis laughed ruefully and said "No, I just don't think so. I haven't got that sort of thing in me."

Janet wasn't having that: she took Phyllis by the shoulders and held her with their noses inches apart. "Baloney! Bullshit, even! Look at me, girl -- don't you dare blink or look away. The "thing you don't have in you" is about eight inches long and attached to a nice pile-driving male butt and controlled by a good brain. Now, just be silent for thirty seconds, and think about fucking Jerry. You've seen pictures of him and me, so your imagination should be pretty well primed - just let it run free! Or imagine whomever you wish, but do choose someone specific. Think hard about it, and when I say "TIME'S UP!" I double-damned-dare you to tell me you wouldn't like to have Jerry fuck you silly, and that you simply absolutely haven't got it in you to make it happen. Just you dare tell me in thirty seconds that you're not soaking wet between your legs. Just like I am. GO!"

At about second number ten, Phyllis broke out in furious giggles and blushes. "You win! But there are other reasons I can't. I've never done that stuff. Wouldn't know how."

Janet snorted. "What? Never shaved your pussy, for Pete's sake? I can teach you that in two minutes. Or I can just do it for you! THAT would be something completely new and different for us both! But, Dearie- are you worried about being caught because of shaving all of a sudden? If you and hubby aren't doing the nasty together, who'd ever know? Or care? Except YOU! And I guarantee you'll love it!"

Phyllis reddened brightly and said "No, not JUST that! It's ALL of them. Everything, all of those things, I mean." She held up a hand, ticked off items on her fingers: "I've never shaved my pussy. No man has ever made me come with his mouth. I've never done anal ANYTHING except my OB-GYN's fingers during an exam and although interesting, that wasn't particularly sexy. I've never had a lover, and for sure never a threesome. I think that's five -- a sort of five-fold virginity."

Janet shook her head wonderingly: "You, my old roomie, miss once-upon-a-time-hot-pants, have arrived at age fifty-three, and you've never done any of those things? You are just fucking IMPOSSIBLE! This cannot be allowed to continue! Good lord, girl, such a waste of talent! There's nobody in the world better for you to start with than Jerry. I did. I was sort of halfway joking when I started talking about it two minutes ago, but now I am completely and absolutely serious. I don't own him, and I wouldn't get jealous or any other such juvenile crap. It would be such an incredible hoot, girl! You need to carpe this diem, Phyllis. TRUST ME kiddo - you NEED this... in so many different ways!"

She shrugged, grinned again. "Besides... such fun! We've never shared a man so far as I know -- certainly not literally simultaneously - and I can just imagine the look on his face when we tell him. I've never been in bed with both a man and a woman. I doubt Jerry has been in a threesome yet, although I haven't the foggiest why not -- we can ask, he'll be honest. Please?"

Phyllis sputtered - her deep abdomen had done a most unusual midair quadruple twist with a double backward somersault: she hadn't known that troops of butterflies could undertake massed choreography on the trampoline in her belly.

"Phyllis, he genuinely LIKES you, is seriously attracted to you, he'd hit on you in a minute if I weren't here; believe me! I know that, I can tell -- he liked talking with you and he also liked you physically. You don't need to worry about that. But his FACE, my god I want to see it when we pop this on him -- we could both get ready like I was planning -- I can help you. Shaving and enemas are HUGELY sexy just by themselves. You can lose all those nasty useless, counter-productive virginities in one fell swoop and I'll bet you come at least five or six times doing it. You need that! Please? PLEASE!?"

Phyllis's brain was churning. A big part wanted desperately to scream YES, but the fail-safe 'rational' part was busy applying the brakes. And the brakes were smoking hot and fading on this slippery slope. Finally, shyly, she answered "Tell you what. We have two hours, lots of time like you said. How about I agree to the 'get ready' part -- that'll be fun no matter what. And then when we're all ready, I can make my final decision. Okay?"

Janet shook her head, then agreed grudgingly. "Oh, all right Miss Fraidy-Cat. That's what we'll do. But -- you're in trouble pretty deep here because I know, even if you don't, just how arousing shaving and enemas are. By the time we get through with your prep, you are going to be clawing your way up the curtains like a kitten and you are NEVER going to be able to say NO. So you might as well say yes now, really. Of course, you don't believe me yet, so let's get going. Time's a-wasting."

Janet's scissors and battery-powered mustache trimmer made short work of both pelts. Embarrassment they shoved aside for the actual shaving: Janet demo'd on herself, and by the time she had gone over every hair-bearing square millimeter on Phyllis between waist and thigh, both front and back and in between, the poor girl's juices were flowing mightily. The necessary mechanics of careful trimming brought Phyllis shivering to the edge of climax repeatedly. Likewise the enema. Then, at about half past ten, shorn and emptied and dripping with the hornies, they stood together at the big wall mirror, a study in contrasts. Janet was just short of actually skinny, and very nearly boob-less. Phyllis was inches taller, tens of pounds heavier, approaching zaftig. Blond and blue-eyed versus solid gray and nearly black-eyes.

"He's going to love your boobs, Phyllis. What are they these days, 36 double-dee? He's always been very nice about saying he likes my fried-eggs with raspberry nipples. He does, I can tell, but I know he also likes real boobs. And you've got enough there for two full sets -- you could give me some and hardly miss it! Mother Nature's a bitch, sometimes!"

Phyllis shrugged: her boobs had always been her pride and joy, and even today, after three kids and fifty-plus years, they were strikingly attractive. She shimmied, watched Janet's eyes, then said worriedly "He won't mind my big butt? Or my caesarean scar? Or especially that I won't know what the dickens I'm doing? Won't all that bother him?" She traced a fingertip over the long arc across her abdomen as she listened to herself speaking not in the conditional -- purely in the affirmative and not a trace of IF left! At that moment she realized that she was actually going to do this nutty thing, and her belly gave a huge and quite delightful twist.

Janet noticed the grammatical shift and grinned internally: "Phyllis, believe me -- I keep telling you that I know this man. Jerry genuinely likes women, and their bodies. He understands them! He simply loves butts, and armpits, and ankles, and mouths, and earlobes, and boobs, and pussies. Pussies uber alles for mouth games, and for warm-up fucking, and then it's butts for serious, prolonged, high-intensity fucking. Pussy-fucking is for kids to make babies, that's what he taught me long ago -- he maintains and I agree that the true center of the erotic is way up inside your butt. The only thing that can properly set it off is a well-applied cock, and once you've experienced it you are NEVER going back to simple momma-poppa pussy fucking! Trust me, he's going to be very careful and considerate and sexy -- I know how he treats first-timers because he taught me, and did so the very first time we ever slept together. I was scared to death of the whole idea before we started -- took me about twenty seconds to dump that opinion! I honestly don't remember if he got into my pussy before my bottom, he's that persuasive, and that good. God how I came that first time! Now -- you and me, WE are going to do this thing. You can't back down now. No way! Okay?"

Phyllis managed to nod. Yes -- carpe the ever-loving diem, she was going to DO it, by god. "YES! Okay I mean. Let's do it. But how are we going to set things up?"

Janet was way ahead -- she already had a fully-fledged plan. "We write two notes, one is pretty innocent and goes on the outside door for him to find before he knocks. He will be EXACTLY on time, by the way. That note just says "Don't knock. Come in, shut the door, say not a word, and read note number two on the other side of this door." That gets him into the room, and mystified. He'll have a perfectly gorgeous cast-iron hardon immediately -- believe me, I know our man! Then the second note says "Stand there and strip naked. Then knock once on the wall and come on into the room." Then he finds us, you and me, side by side on the bed on our chests and knees, butt beside butt, waiting. So there are our two naked bottoms and shaved pussies staring up at him. We just stay still and and silent, and wait to see what he does. I guarantee we're going to enjoy whatever it is!"

Phyllis blushed furiously -- she'd never dreamt of putting herself into such an exposed and blatantly, wantonly inviting position. But the idea had its own strong, perverse attraction. She gulped slightly and nodded.

Janet said "Good! You write note number one, he won't know whose writing it is, that'll intrigue him too! I'll do number two."

Two sheets from the phone-pad, two pens. Janet first wrote what she'd told Phyllis, then added a terse little paragraph all her own: "Jerry, we've set up a threesome. Phyllis is my dearest friend. She's NEVER EVER been eaten to a climax. Never even tried anal. Do HER FIRST, and you treat her RIGHT. Gentle, careful, and LOTS of orgasms. LOTS! Me you can handle after that. I can wait. A little while. Thanks!"

They posted the notes without reading one-another's. Janet turned the thermostat up to 78: "We're going to be naked for quite some time. Room better be at girl-temp, not man-temp!" Ten minutes to go, Janet had another idea. She grabbed a lipstick, handed it to Phyllis, lay down on the bed and said "Write on my butt, just above the crack. Write 'Enter in rear' with an arrow. Then I'll write something on you, too. Not quite so crude, though."

She wrote in block letters "Go slow: virgin ass". Then at the last minute, "Grab one of those big rough bath towels -- we'll lay it on the bed under us -- the texture will feel wild on your nipples!" The women positioned themselves at the bed's edge, knees wide apart, a left and right calf touching, boobs flattened against the towel. Phyllis, launching herself headlong into the adventure, secretly wriggled against it, making nipple-lightning. Janet reached to the nightstand, laid a bottle of infinite-slippery lube and her little battery-powered vibrator in the space between them. She grinned lewdly at Phyllis, waggled her butt so their hips rubbed. "RULE NUMBER ONE for all anal games -- you cannot have too much lube!"

A moment later they sensed -- felt rather than heard -- the door opening. Phyllis shivered. Janet waggled her butt again, squeezed Phyllis's hand to help quell the nervousness. Soft sounds of undressing. Ten, then twenty seconds passed before Jerry rapped once and stepped quietly into the room: four female eyes locked onto his in the big wall mirror. Janet was right about his hard-on, and it was attached to quite a nicely constructed body, no overt fat, lots of visible solid musculature. Phyllis bit the towel, kept her eyelock on Jerry as he approached, as his eyes went back and forth between hers and Janet's, then shifted to their bottoms. Phyllis's lube-glands did something that felt exactly like her salivary glands when she bit into a fresh lemon.

Jerry stopped to look, his face bemused, appreciative. After a long stare, he said "Lovely! What a beautiful pair of pairs! Pear-shaped pairs. Such a nice contrast. My god but the two of you are beautiful! And you both come complete with printed instructions! How quaint." They continued to study him in the mirror. He knelt and they lost eye contact, but he kept musing aloud on the view. "A study in the differences between pussies! Two extremes, Janet has such pronounced outer lips, and the inners hang out so nicely. Phyllis -- you practically have no lips, but such a wonderful, smooth, lickable surface!" Each of his hands took possession of one bottom, caressing. Both sets of female thighs produced swarms of goose-bumps. He maneuvered a fingertip up each slit -- "Wet, both of you. Positively dripping. I wonder why?" A long pause, then quietly "Janet, if I'm to be a gentleman and display good manners, then I have to take care of Phyllis first. Don't you agree?" Janet's vague murmur passed for assent. "Don't worry, Lady Janet, we'll get to you soon enough!" He turned to Phyllis's bottom, said gently "Your clit is still in hiding. Use your hands to spread yourself wide for me. I need access, please, to do my job."