I still clearly remember my first near-miss with Lena. We were both in the ninth grade, and I had a perpetual erection. Lena was my best friend, had been practically since kindergarten, and we were over at Katja’s house. Everyone was there, all the social outcasts from our high school: every dork, dweeb, nerd, geek, and punk; all thirteen of us. We were watching a terrible movie that purportedly had a brief shot of full-frontal nudity in it. Katja’s parents were hippies; as long as we weren’t actually shooting heroin or smoking tobacco products, they really didn’t care what we did.
The lights in the living room were turned off and the only illumination came from the big, clunky, antique television set. Sickly sweet, watery sangria was drunk. Two by two, the kids who would line the gym walls at the school dances, the one’s wouldn’t normally get anything other than ignored and humiliated by the opposite sex began to pair off and slip away: down to the basement, over to the game room, out onto the back porch.
I was sitting on the couch next to Lena. She was sitting next to Katja. Lena’s hand was resting lightly on my jeans-clad thigh, and seemed to me to be moving, with glacial, almost imperceptible slowness, closer and closer toward my aching, straining, mortifyingly visible erection. My dick was drooling inside my uncomfortable tight white briefs, and I was trying to work out in my head what exactly I should say to her that would sound neither ridiculous nor obscene. Before I managed to open my trap though, Katja had put her arm around Lena’s shoulders and whispered something in her ear.
The two girls got up and more or less discreetly left the room together, hand in hand, exiting through the back door. Nobody else paid any attention. The air was practically foggy with horny pheromones. Soon enough, I was the only kid left in the room to witness the fleeting nude scene. It really wasn’t worth the wait.
For a while after that, Lena and I weren’t best friends any more, but I got over it soon enough.
We’d always told each other everything, pretty much. Now Lena had a lot to tell me, and she blithely kept me up to date on her new foray into the wild world of sexuality.
It turns out that Lena and Katja hadn’t actually had sex that first night, as I had assumed. They had just sat out by the beach and kissed and touched for a while. When Lena had finally gone home – alone – she’d been so turned-on (she told me a little sheepishly) that she’d had to masturbate. She proceeded to give me a little (fully clothed) demonstration, propping her feet up on the raw plywood table in the basement where a dozen or so lead miniature figures marched across a labyrinth of graph paper, and running a long slender middle finger up and down the seam at the center of her crotch, where the two legs of her jeans came together. Up and down, and back up again, pausing to do a few pirouettes at the apex of its traverse, just below the bottom button of her fly, and then swooping back down toward here petite butt cheeks, ensconced in soft blue denim. Watching her, I nearly came in my own pants.
Katja, tall and slender and blonde and Scandinavian-looking, with none of that adolescent awkwardness that plagued the rest of us, was a virgin, in every sense of the word. So was Lena, for all her lustful intent and active imagination. They learned together, and I got to hear all about it. Lena would give me the blow-by-blow while we were riding our bikes home from school, or doing pre-calculus homework together, or plotting new D&D adventures in my basement. She casually perpetuated my eternal hard-on, like an arsonist lazily dripping kerosene on glowing embers just to watch them flare up. My poor cock became a single-headed hydra that I wrestled with and slew single-handed every night, only to have it spring forth anew every morning.
Katja had a really pretty pussy, she said. It tasted pretty nice. She’d been afraid she wouldn’t be any good at licking pussy, she told me. She said she’d been afraid she wouldn’t like the taste. It wasn’t at all bad, she confided in me. It wasn’t like honey, not something you’d pour on your breakfast cereal, but it wasn’t bad. Kind of salty, she mused thoughtfully, kind of smoky-sweet, kind of something else… Would I like to try some?
I don’t remember what I said, but my dick, which was already obnoxiously hard from just being alone with Lena and listening to her talk about sex, suddenly strained and throbbed painfully inside my pants.
Lena looked around, as if she needed to be certain that no-one had snuck down into the basement with us and was surreptitiously watching. When she was sure we were really alone, she quickly and carefully undid the top button of her jeans, and slipped one hand down her pants. Her hand stayed down there for a moment, digging and probing around; she bit down hard on her lower lip. When she pulled it out, her index finger was wet and slippery, and she held it out for me to sample.
She was right, the taste wasn’t bad at all. I didn’t know how to describe it; it was salty and musky; it was slick and a little sweet. Lena said it was kind of like snot, only sexier. Later on, when I was alone, I would jerk off with that taste still lingering in my mouth.
Lena and Katja dated all the way through high school, on and off. Katja, it turned out, was a jealous type, and fond of drama. Lena, on the other hand, was conflict-averse, and would rather hide in my basement with me, playing antique video games for hours on end, than risk a fight. I remained resolutely, and unwillingly, a virgin.
They broke up for the last time early in our senior year. I got to spend the remainder of our high school career listening to Lena gripe and moan about the sex she wasn’t having. Katja wasn’t at all kinky; if sex was food, she liked meat and potatoes, and lots of it. Lena always wanted to explore, experiment, push boundaries, and Katja would have none of it.
Lena had wanted to dabble in S&M. She asked Katja to tie her to the bed and give her a spanking before fucking her; Katja called her a pervert. Lena had wanted to try a threesome (here, she pressed her thigh suggestively against my own); Katja wasn’t interested. Lena had wanted to experiment with anal sex; Katja thought that was unhygienic, unnatural, and just plain gross.
When we graduated from high school, we both split our flat and sleepy hometown like the place was Chernobyl. At one point we had talked about going to the State College and being roommates, but that wasn’t how it worked out. We ended up fleeing in opposite directions: she went East and I headed West. Our dorm rooms were a continent apart, but we stayed in contact over the phone and the internet.
I lost my virginity in due course, got my heart broken a few times over, and along the way I also made the exciting discovery that there is more to mathematics than solving quadratic equations and finding derivatives. I discovered that it was fun. And that I had some real talent for it.
All the way through college, I got constant updates on Lena’s romantic and sexual life. I heard about the stripper she dated, the professor she fucked, and the roommate she wanted to fuck, but didn’t. I got to hear about her brief foray into heterosexuality (“I don’t know, I mean I had orgasms and everything, but it just didn’t feel right. You know, he had a dick.”). I got to hear about the woes of yeast infections, and the unfortunate timing of her menstrual cycle. As soon as she had an adventure, I would be the first to know.
She called me up one night. It was late on my side of the country; it must have been nearly morning where she was.
“Oh… My… God!” Lena said, “I can’t believe I never tried strap-on sex before!”
She had been house-sitting for one of her professors (not the one she had boinked, a portly women’s studies professor), and of course she had brought her girlfriend du jour over, and of course they had somehow managed to stumbled upon this professor’s treasure trove of sex toys.
“I always wondered what it would be like to have a cock,” she told me, “Once I got the harness buckled on, I thought it looked really sexy. My dick was big and black, and it waggled in front of me when I walked. I made Tanya” (Tanya was her latest girlfriend. I had trouble keeping track of their names) “get down on her knees and suck my dick. She looked really hot doing that. I bet she’s really good at it. It made me think I wouldn’t mind watching her go at it some day…
“Then I had her get naked, and I fucked her doggy-style right there in my professor’s library. It was so fucking hot! Her pussy looked like it was begging for my cock. I swear I could actually feel her pussy squeezing my dick when I slipped the head inside her. She was soaking wet, and so was I!
“Damn! Fucking is a workout! No wonder you guys have such cute little butts. I fucked her really hard, and she loved it. I loved it too. I stuck a finger up her butthole and totally made her come all over my dick, and that was all I needed. I came too, just by grinding the base of the dildo against my clit. Man, you wouldn’t believe how wet I was! It was so fucking sexy!
“You know what? Just telling you about it just now got me moist all over again. I might have to let you go now, and take care of some pressing personal business.”
I certainly had some pressing personal business of my own to take care of.
Later on, I got to hear all about her very first threesome. Of course. Lena called me up on the phone and gave me all the gory details. She wasn’t a big fan of the experience: too many fingers and tongues going on; too hard to keep track of which body parts belonged to whom. Me, I couldn’t have been more green with jealousy if you had dumped a bucket of paint over my head.
Lena had a crush on this one girl, Angela. She was a freshman, straight out of Ohio, a sociology major, all of five feet-nothing tall with freckles and unruly mop-top of brown hair, and a penchant for wearing pajama pants to class without (as far as her flock of admirers could make out) anything on underneath. She was as adorably cute (so Lena told me) as a little plush Elmo doll. This other girl, Darcie, had the same crush going on, and the two of them had been competing for young Angela’s affections all semester, while she basked in the attention and toyed with their emotions, pitting the one against the other, and playing the ‘I’m not really sure if I’m really gay’ game. Actually, she sounded like a bit of a twat to me, but infatuation will do strange things.
So, probably inevitably, the three of them ended up in Angela’s dorm room one fall afternoon. Wine coolers were sipped, pot was smoked, innuendo flew like fall leaves on a blustery day, and the hormones and pheromones and other bodily juices were flowing like ecstasy at a rave.
It started with tickling. Angela was wearing a red t-shirt with googly eyeballs and the words “Tickle Me” emblazoned across the front in big pink letters; and both Darcie and Lena took her up on the offer with gusto.
As you can probably imaging, things progressed (or digressed) rapidly from there. Small, ticklish, and coy, but horny Angela found herself sandwiched in between two bigger, more persistent, and hornier girls. Hands strayed, fingers roamed, and various layers of clothing came flying off.
Four hands were inside Angela’s soft plaid pajama bottoms, while two mouths competed for the affections of her lips. Angela was thoroughly enjoying herself, reveling in the attention.
Pros: The way it started out anyway, the whole scene was hotter than hell, and Angela was even cuter naked than with her clothes on. She did not, in fact, have anything on underneath those pajama bottoms, and her pussy was shaved bare. She had (and I quote here) ‘A taut little body; pretty, perky boobs, and a tight little ass that was simply delectable’.
Cons: Maybe it was just inexperience, but Angela came off as a rather passive, selfish lover, content to have things done to her, without participating overly much. And when she did participate, she was a bit of a biter, which was more annoying than cute or sexy. She was also just a little bit of a prude, and was kind of picky about where and how she got touched.
At first, the two girls concentrated on Angela, both of them fingering her pussy at the same time while they each kissed and sucked one of her pointy little breasts. They took turns licking her over-excited pink little clit. Lena stood on the bed and held her upside-down by the ankles, allowing Darcie to slurp up and down her bald, puffy, slippery slit while Angela sputtered and protested unconvincingly.
But slowly Lena and Darcie gravitated toward each other, paying less and less attention to Angela until she was no longer really even part of the game. What had started out as a hot threesome was now a really hot twosome with one irritating spectator trying to get a few licks in here and there.
Darcie wasn’t all that hot-looking, I thought; from the photos Lena sent she looked to me kind of plain-looking and chunky. She had an upturned little piggy nose that could charitably be described as ‘cute’; but when it comes right down to it, good looks only count for so much. She was bright, funny, over-sexed, kinky, and had a tongue (Lena assured me) like a mutant iguana. And, as a bonus, she really got off on S&M and anal play.
They ended up in what Lena described as sort of a contorted 69 position, with Lena doing a semi-shoulder stand on Angela’s bed, her feet propped up against the dorm-room wall, with Darcie kneeling on top, straddling Lena’s face, her own fuzzy pussy just barely within tongue’s reach. While Lena strained upward to get her licks in, Darcie pried Lena’s buttocks apart, and buried her face between the cheeks like a girl eating the biggest, juiciest peach in the world, doing her absolute damnedest to shove her tongue all the way up Lena’s ass. All the while Angela nipped and yapped at their haunches like an annoying little Chihuahua dog, frustrated beyond measure at being ignored.
That sort of sealed the deal. Darcie and Lena moved in together not long after, and were together all the way through college and beyond. Darcie was plenty kinky enough for Lena, and more than willing to try anything Lena could dream up.
A graduate degree in pure mathematics may not be especially glamorous, and certainly isn’t any kind of a chick-magnet; but it proved awful attractive to the big insurance companies. They were, I found, more than willing to pay ridiculous amounts of money to anyone who could write them some halfway clever algorithms to help cope with their chronic information overload. And all I had to do was sell my soul.
I bought myself a five-bedroom house, four bedrooms of which remained eerily vacant, in Wisconsin, where I dabbled in windsurfing, jogged sporadically, drew a blank on the dating websites, and masturbated fitfully. My twenties passed by, if not exactly happily, then prosperously and generally uneventfully.
I still had long, one-handed conversations with Lena on a regular basis. She was in Berkeley, teaching freshman English, and living with Darcie, who was going to grad school for Bioengineering.
“We made guacamole tonight.”
“Oh Really?” I said into the phone, “That’s nice.”
“Oh Yeah. It started out in the morning. Darcie woke me up by licking on my kitty, and then I discovered that she’d already tied my wrists to the bed frame. She likes to do that. Well, she kept on licking me and teasing me, and getting me wetter and wetter, but she wouldn’t let me come. Are you still there?”
I was still there. My dick was hard and out and wrapped comfortably in my right hand. Lena went on.
“So from somewhere, Darce pulls out an avocado, and starts rubbing it up and down my poor hungry pussy, which felt pretty excellent. I was begging her to hurry up and fuck me, and she just laughed.
“She started really grinding and shoving that avocado up against my twat, which felt really nice, and then, just as I was starting to realize what she was up to, the whole fucking thing slipped right up inside me.
“It felt weird, and a little scary, like I had been stretched almost but not quite past my limit, and it definitely felt sexy in there. But weird.
“Darce laughed at me again, and kissed me lightly on the clit, and untied my wrists, and told me to hurry up and get dressed or I’d be late for class.
“She was right, I was already running late. She watched, gloating, as I rummaged around for some clean underwear, hurriedly pulled on the same skirt and top I’d worn the day before, and slapped some deodorant onto my pits. Darce stopped me just before I ran out the door: ‘Lose the panties.’ she said, and I did, kicking them off and leaving them right in the middle of our apartment floor.
“And so I had to teach three sections of English 101 to a roomfull of bored, fidgety, ADD-ridden freshman, all the while trying to keep that obnoxious avocado from falling out of my pussy mid-lecture. My clit stayed obnoxiously erect all day, and my pussy wouldn’t stop drooling. I swear, by mid-afternoon, my juices were running down my thighs.
“When I finally got home, Darcie was ready for me. She tackled me, threw me bodily across the couch, and proceeded to eat out my asshole like a hungry dog with a tin can of soup. Which was plenty hot, but then she butt-fucked me with about three fingers while pulling mercilessly on my hair until I came like fucking TNT. Dude, it was the most amazing orgasm I’ve had in a long time, and right in the middle of it, that naughty avocado popped right out of my cunt and shot halfway across the room. And then we mashed it up, and made guacamole out of it, and had it for dinner with chips and salsa.”
I managed to not actually shoot off until she had hung up.
The McMansion I’d bought was way too big for a single guy living alone. Hell, it would probably have been too big for a family of seven. Lena and Darcie came to visit once; they made a detour during a cross-country road trip. Having guests over just made the place seem even bigger and emptier than it already was. The unfurnished rooms and bare hallways rang with their footsteps like it was the Mines of Moria.
It had been a long time since I had seen Lena in the flesh, and she gave me a big, warm, friendly hug that seemed to last a few beats too long, and left me slightly dazed and obnoxiously erect. I swear she had pressed her crotch up against mine on purpose.
Darcie struck me as bossy, abrasive, and overly sarcastic, a woman who had a chip on her shoulder. She reminded me more than a little of the Stay Puft Marshmallow Man. The blue blazer and shorts and the red tie she was wearing only added to that impression.
We ordered pizza (at the time my cooking repertoire was limited to mac & cheese and instant Indian), and proceeded to get fairly shitfaced drunk over a couple of bottles of overpriced wine with pretty labels. Darcie kept sticking her hand down the front of Lena’s shirt. The drunker we all got, the sloppier they became, kissing and making out in a big overstuffed armchair right there in front of me. Lena removed her bra without taking off her t-shirt; pulling it off through one of the sleeves and tossing it on my floor. Darce slipped both hands up inside Lena’s shirt, and started nibbling on one ear. My dick was straining against the zipper of my pants. Lena was sitting on Darcie’s lap, perched atop one of her thick, pale legs like she was riding a horse bareback. Darce leeringly asked me which bedroom was theirs. I told them they could have their pick.
They chose the bedroom adjoining my own. I helped them inflate my ‘guest bed’ air mattress, and gave them a pile of sheets and a couple towels before leaving them to their own nefarious devices. Inside my own bedroom, I lay naked on my bed with my ear pressed up against the wall.
I could barely hear Darcie at all; just a few grunts here and there, and some muffled, unintelligible whispering. But Lena I could make out loud and clear; every moan, every gasp, every throaty entreaty. It was almost as if she was being loud on purpose to make sure I could hear everything.
“God, I love the way you touch me… You make me so horny Babe… Can you feel how wet you make me?
“Fuck, I love it when you do that to me… Oh, you sexy thing!
Through the thin, cheaply-built wall, I heard the *whump* of two bodies tumbling onto the air mattress. I heard a rustling sound, and some grunting and the sudden hissing sound of someone sucking in air through clenched teeth. A hoarse, half-whispered “Quiet!” in Darcie’s voice, immediately followed by a peel of girlish giggling.
“…I don’t care if he does… OW! Oh, you bitch!” It was Lena’s voice again.
“Mmm, well don’t stop… yeah, that feels good… oh, so good… mmm, yes… what are you doing?”
There was a startlingly loud and clear SMACK! that resonated straight through the thin sheetrock wall and jangled my eardrum. In my mind’s eye, I pictured Darcie’s hand crashing down on the soft, pale expanse of Lena’s naked butt, leaving a scarlet handprint, and I held my breath, expecting an outraged scream of pain to follow, but it never came.
SMACK! SMACK! SMACK! The beating continued, as they say, until morale improved.
(something inaudible from Darcie) Then Lena: “Well why don’t you taste it and find out?”
And then louder: “Oh fuck yes! Oh yeah girl, eat my pussy! Oh fuck yes! Stick it in my ass! Fuck my asshole! Oh you horny fucking bitch! I love you! Oh fuck my ass harder! Lick my cunt! I’m coming! I’m coming! I’m fucking coming, oh shit!
I was too, in a big way. I rolled away from the wall, flat on my back on my bed and jerked with abandon, squirting semen all over my belly and gnawing on my own shoulder to keep from shouting out. I slept hard that night.
The next morning, I took them out for breakfast, and wished them well. I didn’t see Lena again for many years, though we stayed via email and now and then over the phone.
In the middle of the worst economic crisis in a generation, I finally worked up the nerve quit the high-paying job that I hated. I sold my house at a loss, and moved to the Pacific Coast where I bought a small place that the realtor optimistically described as ‘rustic’. The roof leaked when it rained, which was often, but I could see mountains from my back yard, and I windsurfed every morning and ran every evening. I took a job teaching math at the local community college, and discovered that not only was I pretty good at teaching, but that I also enjoyed it very much. I met a girl, fell in love, got married, and for the first time in my life, I was having sex on a regular basis. It was good sex too: lights-on, exuberant, unselfconscious, meat-and-potatoes straight-up fucking. If I wasn’t completely happy, I certainly didn’t have anything to complain about.
Lena and Darcie were one of the first couples in their state to take advantage of the new same-sex marriage laws. They were also one of the first gay couples to get divorced.
They’d hooked up with another girl, a woman who was a former ex-girlfriend to them both, and for a while it had been one big hot, kinky, three-way lesbian fuck-fest. She pocket-dialed me during one of those fuck-fests. I’m pretty sure she did it by mistake, but holy shit! And then things inevitably went south, and this time Lena was the odd woman out. She got her own place, dabbled in alcoholism, and spent a lot of time in therapy. We were chatting via email one day, talking about life and the strange places it had taken us, and all of a sudden it hit us both, like an eight-pound hammer right between the eyes: we had somehow, without realizing it, become middle-aged.
I ran into Lena recently. She was in my corner of the country for a conference, and emailed me to ask if I wanted to get a drink. Of course I did.
She still looked hot to me, though the years had taken their toll. There were permanent dark patches under her eyes, and she looked like she had put on some weight. She gave me a big warm hug, and I felt the softness of her breasts pressed up against my chest.
We annexed a corner table, and proceeded to get shitfaced while we caught each other up on our lives. If Lena had gained weight, it didn’t look bad on her, no not at all. She looked bustier than she ever had before, softer and more vulnerable, and her foot kept brushing up against my leg under the table in a way that was most distressing.
I asked her if she had a new girlfriend, and she told me no, she had given up on girlfriends. She asked if my wife knew where I was tonight. I said I’d told my wife I was just meeting an old friend from high school for a drink or two. She raised her eyebrows at that, but didn’t say anything else.
When she got up to use the bathroom, I watched her ass sway across the restaurant, wide and soft and delicious-looking. I thought about Darcie sodomizing her in the guest bedroom of my awful old McMansion. I wondered if I’d ever work up the nerve to ask my wife if she’d like to try anal sex.
Lena came back, and against our own better judgment, we ordered more drinks. I asked her if she remembered that night at Katja’s house way back when. She sure did.
I told her that I’d been too shy to make a move on her that night.
“Phew!” she said, “Just think if you had! Man, I was so horny that night, if you’d just given me an opening I would totally have jumped your bones…”
My face must have given it all away.
“Oh no,” she said, “Oh God, you’ve been holding onto that all these years, haven’t you? Oh Honey, you can’t live your life like that. You’re clinging to might-have-beens like last winter’s snowflakes. Let it go Baby, let it all go.”
Lena took a cab back to her hotel; I drove home, though I really was in no condition to do so. I took my time, driving slowly on back roads, sucking my teeth and feeling hollow and brittle inside. By the time I walked in the front door, I was halfway sober.
“Honey,” I called, “I’m home.”