My best friend Amy’s divorce was bitter, protracted, acrimonious, and complicated by the fact that she and her girlfriend weren’t actually married or anything of the sort. They had, however, been together ten years; and they owned a car, and a house, and a houseful of stuff together, and Alice fought her every inch of the way.
My own divorce was a sedate, banal, relatively amicable affair. John and I simply threw in the towel, calling it quits after eight years of marriage, six of them really quite pleasant. We let the lease on our apartment expire; divided up our junk; gave away or threw away the stuff neither of us wanted; split the security deposit, and went our separate ways.
John promptly got a new girlfriend, and I couldn’t even bring myself to hate her. As a matter of fact, I would have done a threesome with them, if John had asked, just for old times’ sake. But he didn’t ask.
Amy rented herself a Ryder truck headed east, packed full of books, furniture, and garbage bags full of clothing. I took an Amtrak train west, carrying a backpack stuffed full of my laptop, a couple changes of clothes, extra underwear, and my running shoes. We met up in Chicago.
We got ourselves apartment, a medium-small two bedroom place in Lakeside East, not too cheap, not too sketchy. We unpacked and moved in. We got jobs, we drank too much, we cried a lot. We’d been best friends since college, but we’d never lived together. It actually worked out surprisingly well.
I belatedly discovered internet porn, and re-learned how to masturbate. I hadn’t had sex in over a year, and I craved it, in mind and in body.
I hooked up with some guy off the internet. There was never any pretense that it was about anything more or less than sex. It was a one-night-stand; my first attempt at such a thing, and I wasn’t sure how I’d react.
He wasn’t particularly attractive, but he was attractive enough. Conversation was awkward, adolescent. I had the impression, though I didn’t bother asking, that he hadn’t done this before either. I brought him back to my place. Amy, thank God, wasn’t home.
In my bedroom, we got down to business. He didn’t want to kiss me, which made me feel weird. I hadn’t seen another penis (in person) since John and I had first gotten together, over a decade ago. I discovered that, while I’m not especially picky about penis size; apparently I am quite particular about penis aesthetics. This guy did not have an attractive dick: it was reasonably long, but the shaft was pale and skinny, and the crown was an unpleasant shade of pink and shaped like an English bobby’s helmet. He shaved his pubes, which I found oddly disturbing, in a way I couldn’t quite put my finger on.
He did, however, eat pussy; and I had no complaints about that! He was nearly bald on top, and his head looked really sexy down between my thighs, and the things he was doing with his tongue were simply amazing. It wasn’t like John had never gone down on me; he used to before our sex life had dried up completley; but this guy’s style was completely different. Not better, definitely not worse. Just different.
He ended up sucking my clit between his lips like a strand of spaghetti, humming an AC/DC tune, and finger banging me to the loudest, most intense orgasm I’d had in ages.
I sucked his dick a little bit, an activity that I’d forgotten how much I enjoyed; and then he pulled away, wet dick bobbing merrily and pointing up at the ceiling. We were ready for the main event.
He didn’t want to wear a condom. He didn’t exactly fight me on it, but he was obviously reluctant, and disappointed when I insisted.
I wasn’t going to get another orgasm out of the deal, but it did feel really nice to have a real, honest-to-God penis inside of me. He fucked me hard, deep, and selfishly, which was just fine. It didn’t take that long, which was OK too. I thought it was really sexy when he came, and I could feel his cock twitching all the way through the condom. I grabbed his balls and held him deep inside me until he finally stopped moving.
The after-sex conversation was painfully stilted, awkward, and mercifully brief. As he got dressed, I lay naked on my bed, feeling kind of horny, kind of dirty and gross, and deeply discombobulated.
He thanked me for my time–whatever that meant—and went to shake my hand, then thought better of it. He said goodbye and left. I got up and took a shower.
I started whacking off under the hot spray of water, and about halfway through I realized I was crying. I couldn’t stop masturbating, and I couldn’t stop crying. I was in the shower for a long time.
When I finally did get out, out of tears and unsatisfied, Amy was home. She asked me how my date went. I shrugged. She asked me if I was OK and I said ‘I guess so’.
I woke up to the sound of screaming. There was a clatter and clunk of furniture being violently knocked over, and then the cry again. It was Amy. “No! No! Please no! Don’t! No!”
“Shut up, cunt!” That was another voice, low and deep and guttural, and it seemed to resonate up and down the walls of the apartment. I heard a WHUMP that sounded an awful lot like a body being thrown across a room.
I grabbed an umbrella—I don’t know why, it was the closest thing to a weapon that came to mind—and burst into Amy’s bedroom, my adrenal glands cranking away on afterburner.
Amy was sprawled out, completely naked, half-on and half-off her bed. A little trickle of red was leaking from her nose, and a small vise-grip dangling from one breast, clamped onto a nipple. Her legs were splayed apart and I could see everything. Her pussy was almost bald. There was a single puff of soft hair down there, crowning her vulva like a cowlick. She had prominent, pink labia that peeked and curled out.
A woman I didn’t recognize, the size and shape of a dump truck, was towering threateningly over her. She was wearing black granny panties, a black sports bra, and she had an impressive-looking black dildo strapped to one of her thick, meaty thighs.
They both stopped what they were doing, frozen like bunny rabbits, and looked at me.
I felt small and ridiculous in my baby-blue pajamas, wielding a short green umbrella.
“It’s OK,” Amy said, “We’re just playing.”
I’ve never been so embarrassed in my life.
Amy told me later that the woman’s name was Phoebe; that they’d met in a bar; that it had just been a one-night stand; and the sex wasn’t really all that great. Apparently Phoebe had a reputation for picking up new girls on the scene, chewing them up, and spitting them back out again. We had a pretty good laugh about it, but I just couldn’t get that image out of my head: Amy, naked, eyes glazed and legs spread, and pussy ready and wet.
A number of people (many of them horny girls on the make) have told me that everybody is bisexual to one degree or another. I’m not sure I agree. I like guys, I always have. I like their bodies. I like their dicks. I’ve never been attracted to women in general, or to Amy in particular.
So I still have no idea what I was doing when I traversed our apartment in the middle of the night, quietly opened her bedroom door, and slipped into bed with her. I think I was just horny.
I was wearing my pajamas; Amy always slept naked except for panties. I don’t know whether she was asleep or not when I climbed into her bed; but when I snuggled tightly up against her backside, like two spoons in a drawer, she slithered her underwear right on down, kicking her panties off and pressing her naked butt against me.
We kissed for a long time like that. She was looking back over her shoulder at me, craning her neck, her long hair falling all over her face and getting in our mouths. It felt weird to kiss a girl. Her lips were really soft.
I cupped her breasts in my hands. They were smaller than mine, but beautiful, soft and warm, like half-melted butter. The nipples were achingly hard. I squeezed one and she very softly moaned, and squirmed her ass against my pajama-covered crotch.
My cunt was on fire, my clitoris bulging and straining.
We kicked the blankets aside. It was very dark in the room; I could only barely see her naked body. I slid down between her legs, which parted for me like an automatic door.
She was incredibly, shockingly wet, a floodplain of hot and slippery joy juice. I started licking. The taste was powerful, almost overwhelming, but not necessarily bad. I was immediately lost, bewildered, overwhelmed in her folds. I felt a sudden rush of sympathy for every guy who’d ever gone down on me and fumbled it: these pussy things are complicated—they should come with a road map! I settled on slurping, dragging the flat of my tongue up and down her pussy, and occasionally swirling it around what I was pretty sure was her clit.
I must have been doing something right because she kept getting wetter and wetter, and she wrapped her legs around the back of my head, and grabbed a fistful of my hair and pulled my face deeper into her, until I thought I might drown in her pussy.
Finally, her whole body went rigid, tight as a drawn bow, and she made an ‘ah-ah-ah’ sound like someone who has just jumped into a freezing cold swimming pool, and I knew she was coming, and I felt a rush of pride and pleasure all my own, and kept my tongue jammed up against the squirming little knob of her clit.
Then she sighed and relaxed and unclenched, and she was done, and I disengaged myself from her damp pussy and kissed her one more time on the lips, and slipped back into my own room and my own bed, where I whacked off to the memory of eating her out, her juices still fresh on my own lips.
The next morning, over coffee, Amy asked me if we were OK. “Yeah,” I said, not meeting her eyes. “We’re OK.”
Amy came to my bed that night. I was halfway expecting her, lying on top of my sheets with one hand down my pajama bottoms, idly masturbating.
She wasn’t wearing anything. That is to say, she was naked except for a black nylon harness. A formidable neon-yellow dildo jutted out from her crotch, with spiraling ridges like a unicorn’s ivory horn, and a fat, mushroom-shaped crown at the end.
“I want to fuck you,” she said, standing at the foot of my bed.
“Alright,” I whispered.
“I want to fuck your sweet little ass.”
My entire body shivered with a secret thrill. “Yes,” I said softly, “do it.”
John and I had tried anal sex once, mostly I guess because we felt like we should try it at least once. It had been OK. I think it had kind of weirded John out; he had never tried or asked for it again. It hadn’t exactly rocked my world either, but I remember thinking, ‘This has potential…’
Amy climbed up onto my bed, took my pajama bottoms by the ankles, and yanked them right off. She looked powerfully sexy like that, sexy in a way I never would have imagined, with her petite boobs hanging down, and that big day-glo phallus projecting out from her crotch. She clambered on top of me, kissing me hard and biting my lips and neck, and I strained to rub my pussy against her dick.
She flipped me over onto my hands and knees. My tits hung down, feeling heavy and vulnerable inside my cotton pajama top. Amy caressed me through the soft fabric, pinching and tweaking my nipples. I shivered.
I wanted her. I wanted it viscerally, in a way I could taste, in a way that made my molars ache. I wanted her to take me, pound me, skewer me, sodomize me. I wanted her to fuck my ass until I couldn’t take any more. And then some.
She kissed the back of my neck, and her dildo brushed against the backs of my thighs. I shivered again, savoring the anticipation, wanting her.
Amy took her time about it, kissing her way down my spine, agonizingly stretching my anticipation out to the breaking point. I could feel my cunt drooling away between my legs. God, I wanted this.
Her kissing lips finally made it down past my tailbone, down between my cheeks. It was like a floodgate had been opened up. I could feel my own wetness, hot and slick on my thighs; my clit was swollen and super-sensitive. I squirmed, mashing my labia together, as she kissed and licked her way up and down the cleft of my ass.
Then her tongue found its way inside my anus, and I moaned aloud, arching my back like a horny cat and pressing back toward her. She gurgled something and pressed her tongue even further inside me. I couldn’t believe how good it felt, how raunchy and nasty and deliciously exquisite. My clit felt like a dong, fat and thick, jutting out from my pussy like my very own cock. Amy shifted position, removing her tongue from my asshole, and nudged her dildo against the sphincter.
“I’ll be gentle,” she said.
“Fuck me!” I said, pushing back hard against her.
The bulbous head of Amy’s neon dildo nudged its way through my sphincter muscle, making me gasp involuntarily. The invasion felt weird. Weird but good. Really good.
True to her word, she fucked me gently. Too gently even. Long before she had the whole shaft buried in my asshole, I was begging with her, pleading with her to fuck me, fuck my ass harder.
Finally she obliged. Her hands on my hips, she started fucking me in earnest, sliding her silicone cock in and out of my asshole, making a sweet little grunting noise with each thrust.
I was totally out of control, howling like a monkey, grinding my ass back against her humps. Amy slapped my ass hard, alternating cheeks, making it sting; once, twice, three, four times: Smack! Smack! Smack! Smack! She slipped a finger into my already distended asshole, alongside the dildo, and that was just enough to set me off.
I came, and I came hard, like a motherfucking avalanche rolling down the mountain. It was the first and so far only time I’ve orgasmed without any vaginal or clitoral stimulation, and it was one of the most intense ones I’ve ever experienced.
I think Amy came too, at the same time, but I was kind of wrapped up in my own spasms of pleasure, so I’m not sure.
She gently disengaged from me, which if anything felt stranger than the insertion, and kissed me: the top of my head, the back of my neck, the small of my back, each tingling ass cheek, the backs of my knees, my toes. Then she padded off out of my room, back to her own bed.
Things were a little weird between us after that. Not exactly bad weird, but our relationship was definitely a little bit tangibly off. Our friendship felt strained. We never did fuck again, though I certainly contemplated it. I still don’t think I’m bisexual; maybe I’m an amphibian.
We ended up getting separate apartments, which suited us both better anyway.
I talked with John on the phone sometimes. We danced around the topic, without ever actually mentioning the idea, of getting back together. One time we had webcam sex, which was strange and kind of one-sidedly intense. It wasn’t bad exactly; I got an orgasm out of the deal, for sure, and it was kind of cool and a little sexy to watch him jerk off. In all the years we’d been married I’d never gotten to see him masturbate. With someone else, I might have been interested in making a habit out of it; it’s just that John was so intensely into it that it was a little off-putting. After that, I kept him at more than an arm’s length.
Me and Amy went back to being best friends. We’d meet up periodically for coffee or drinks, and bitch about our sex lives, and the lack thereof. I got a tattoo, a small blue salamander crawling up my ankle. Getting it done hurt a lot, but it was a good kind of hurt.
I downgraded my job situation, and went back to school to get a degree that would be actually useful. I loved it: I loved the challenge and the engagement, and the fact that I was surrounded by young guys who were smart, attractive, and more-or-less single.
I shocked myself, and this string-bean of a twenty-year old math savant named Mitch, by asking him out. He shocked me even more by saying “Yes”, and then by kissing me, right then and there in the math lab.
When I got home, there were two new emails in my inbox, both from Amy. The subject line of the first one read ‘Thinking of you…’ The subject of the second was ‘OPEN THIS FIRST’.
It said she had clicked the ‘send’ button without really thinking through the consequences, and asked me to please delete the previous email without reading the contents.
I deleted them both, and then emptied out the ‘trash’ folder, just to be sure I didn’t succumb to temptation later on.
And speaking of temptation, I had a date to get ready for.