Fit the First: The Landing
Carroll rang my phone right at 7:00. Alice, my girlfriend at the time, gave me a look and raised one eyebrow. I guess she hadn’t thought Carroll would actually show. Well, she had thought wrong. Carroll always keeps her appointments. I buzzed her in, and we waited, jittery with tension, as she climbed the six flights to our tiny little apartment.
Alice and I had been dating for nearly eighteen months at the time, a personal record for me, and we’d been cohabitating for a year. It hadn’t been going so great lately. I was starting to feel a little stagnant, a little claustrophobic. Worse yet, Alice was showing signs of getting bored. And then I got the crush.
I told her about Carroll right away; I’m not the kind of guy who’s able to hold stuff like that back. Alice thought it was cute. Alice was the one who suggested inviting her over.
Carroll was a freelancer, a tech, a hired gun. We met at work, and right away we had this very intense instant chemistry. It was like there was an electrical charge passing between us, an electromagnetic attraction. She had milk-chocolate skin, short tidy dreads, and full, plump lips. Her figure was largely hidden under the baggy grey jumpsuit that she always wore to work. She was strong as hell, with ropey muscles that twisted and bulged in her forearms as she worked
She did her thing, troubleshooting an errant control cabinet, while I watched and supervised. It was hot up there on the catwalk, and we were both perspiring freely. I stood a little closer to her than strictly necessary. When I handed her a tool, our hands touched, and I felt a spark that made my dick jump and swell in my pants.
We bantered as she worked, dancing around and eventually gravitating toward the subject of sex, a rapidly decaying orbit of declining decorum. She told me a story about a friend of hers in college who had once shoved a whole avocado up her twat, walked around all day with it inside her, and then made guacamole for her roommates. My dick felt heavy and thick. I bet she had a really nice body inside that baggy jumpsuit.
When I got home and told Alice that I thought this girl at work was interested in me, she grinned. “What did she have to do, flash you her tits? She must have been hitting on you pretty hard!” It’s true, I’m usually really clueless that way. Back when Alice and I first got together, she had to force me to take her phone number.
The next day, elbows-deep in a box full of crossed wires and circuitry, I asked Carroll if she’d like to come over and hang out after work. She came up from inside the tangle of wiring, gave me a look.
“Up was wired to down and down up,” she said, screwdriver dangling idly from one hand, “I thought you had a girlfriend?”
“I do,” I said, “She’ll be there too.”
I told her to be there at seven. I told her to call my cell when she got to the front door; the intercom was broken. I told her I was looking forward to seeing her outside of work, and she grinned.
Fixing the damn cabinet took us the rest of the day.
Carroll knocked, and I opened to door for her. I wouldn’t have recognized her if I’d seen her on the street; but then again I wouldn’t have been looking at her face.
She was wearing white short-shorts that stopped just shy of her crotch, and showed off her long, thick, brown legs. Her midriff was bare, her navel exposed, and she had on a floral halter top that was for all intents and purposes transparent. It was clear that she had nothing on underneath it; her nipples stuck out like a pair of thumbs. Her breasts were a lot bigger than I would have thought, and appeared to be self-supporting.
Carroll smiled, somewhere between sheepish and sardonic. “Can I come in?” she asked. The question was clearly directed to Alice, standing behind my left shoulder.
“Of course,” Alice said, “Come on in.”
The door shut behind her, and there we three were, cheek to cheek to cheek. My apartment is small, too small for two people really. It is just one room, with a barely separate bathroom and a tiny kitchen squeezed in. With three people inside, it was like a crowded elevator. I had an erection that was probably visibly from space. Carroll’s boob kept brushing up against my arm.
The girls sized each other up like a pair of cats.
“Do you guys want to go out?” Alice asked, “Or just stay in?”
“Oh, stay in,” Carroll said, “Definitely stay in.”
We drank a lot of wine that night. Carroll produced some high-quality pot, and we all got stoned. I hadn’t been stoned in years. We all ended up on the bed together; there was really nowhere else to be.
It was really late, and I was dizzy and yawning, and my eyes kept drifting shut. I for one had to work in the morning.
“I wanna watch you two fuck.” Carroll declared. That woke me right up.
“Ok,” Alice said, “No problemo.” She was already pulling her shirt off over her head.
My dick, which had started off the night edgily swollen and twitchy, had slowly lapsed into a flaccid state of dormancy as it got later and I got more and more sleepy. Suddenly I was hard again, ragingly, eagerly hard, my erection making a highly visibly lump in the front of my pants.
Any misgivings I may have had about getting naked in front of Carroll were effectively swept aside as Alice tossed her bra aside, and barely suppressing a fit of giggles, went to work on fishing my cock out of my pants.
What proceeded was kind of an awkward dance, like a hobbled game of Twister. We didn’t usually undress each other; usually we showered and got naked and got into bed before getting it on; plus we were both a little drunk and high. The end result found Alice naked, and me nude from the waist down, the pair of us kneeling chest-to-chest on the center of my bed, kissing hard and groping shamelessly.
Carroll migrated to the top of my dresser, sweeping aside a stack of folded towels, sitting cross-legged, enjoying the view, perched up there like a Cheshire Cat, grinning hungrily.
Alice’s not-so-small boobs were pressed against the sweat-damp material of my t-shirt, and her hand was wrapped around the almost painfully hard shaft of my cock.
“This is SO hot!” she whispered in my ear, before traversing her way down my body, grabbing my butt with both hands, and swallowing me whole.
It was hot. Both of us were more turned on than we had been in months and months. Alice’s head bobbed up and down on my dick. Her mouth felt amazing. I couldn’t think of the last time she’d given me a blowjob. I reached around her rump, feeling her up; her pussy was slick and sticky wet.
Carroll had discarded her top. Her boobs were big and round, like a pair of cantaloupes. The areolae were huge and brown, and her nipples stuck out excitedly. There was a thick white scar that ran down the left breast, just missing the areola, and traced its meandering way along her sternum. As I watched, Carroll unfolded her legs and slid her short shorts down, gathering them up around her knees. She was wearing black mesh underwear, and I could see her fat, puffy slit through the sheer material. She slipped her hand down the front of her panties and leaned back against the wall, pinching one large nipple with her free hand.
I was humping back against Alice, fucking her face, my balls swinging lewdly. At last she popped up, panting like she’d just ran a foot race, her eyes wide and sparkling.
“Fuck me,” she said, “Fuck me now. Do it to me, do it hard and fast!”
We reconfigured ourselves so that we were facing Carroll, with Alice on all fours and me behind her. That wasn’t a position we used very often, but it gave us both a great view of what Carroll was doing perched atop the dresser.
We hadn’t used condoms since early on in the dating phase of our relationship. I slid my cock straight up Alice’s pussy. She was shockingly hot, and wetter than I’d ever felt her. Her pussy was hungry for my cock, she seemed to grasp and milk me.
“Fuck me!” she hissed, “Fuck me hard!”
I complied. We fucked hard and we fucked loud. The harder I thrust into Alice, the harder she thrust back, and the more noise she made. Carroll’s fingers were busy inside her panties as we screwed in front of her. Alice’s breasts were swinging, her ass was jiggling, and her head was thrown back as she groaned and whined in unintelligible ecstasy. It felt like heaven: wet, hot, slippery bliss.
It didn’t take long. I was overexcited, and I wasn’t holding anything back. The more noise Alice made, the harder I fucked her, and the harder I fucked, the more noise she made. My balls clenched up, my toes curled, my spine went rigid, and with a shout I buried myself in her juicy pussy one last time, smashing my crotch against her ass, and I came, shooting what felt like buckets and buckets of come into her pussy.
Alice came at almost the same instant, her hand between her thighs, squeezing my dick, rubbing me up and down her sopping pussy, her head upturned, eyes glued on Carroll.
We watched together as Carroll finally got off in a protracted, gasping series of jerks, tits shaking, back arched, fingers buried in her pussy. It was beautiful; when it was over I felt like applauding.
Alice and I cuddled as Carroll got dressed and left. It wasn’t awkward at all, which was both surprising and nice. After she was gone, we turned out the lights and breathed each others air for a little while. It was very, very late, and we both had to work the next day, but her fingers made my dick hard again, and my hand found her pussy still wet, and we managed to bring each other to one last sleepy orgasm apiece before drifting off.
Fit the Second: The Hunting
My phone rang at 7:00 exactly. Not 6:59 or 7:01. The girl was prompt if nothing else. She kept her appointments.
Alice giggled and bounced up and down on the balls of her feet. She was wearing a terrycloth bathrobe with nothing on underneath. I buzzed the door to let Carroll up.
It seemed to take her forever to climb the six flights up to the apartment. My dick was already getting hard, and Alice helped things along by squeezing and rubbing it through my trousers. The sex we’d had the previous week, with Carroll jerking off to us from on high, was the best, we’d both agreed afterward, the best we’d had since we first got together, maybe the best ever. We were both eager for more.
Carroll was wearing tight a little red pleated skirt with white hearts that ended just above her knees, and a black sports bra that squished her big boobs and showed off a long deep valley of cleavage. She was smiling big, two sharp rows of perfect teeth, and she kissed us both as she hopped across the threshold.
“Anybody hungry?” she asked, lifting up her skirt and flashing us a momentary glimpse of her bare plump, brown, shaved pussy, “I baked tarts!”
The tarts were delicious, but eating them at the little round table in the corner of what served as my kitchen, I kept getting distracted, sandwiched in between two attractive, giggling, nearly naked girls who kept using every flimsy, snorking excuse to reach over and touch me and each other under the table.
By the time the tin of tarts was reduced to crumbs, we were all three pretty hopped up, hot and bothered. Alice let her bathrobe fall in a heap on the kitchen floor. Carroll clambered up to her aerie atop the dresser, her red-and-white skirt bundled up around her waist, and snapped her sports bra off like an oversized rubber band.
She caught me staring at the nasty white scar that ran across her otherwise flawless mocha bust. “Welding slag down the front of my bib,” she explained with a careless toss of her dreads, “Hurt like a cunt.”
Alice undressed me, taking her time, kissing each section of bare skin she exposed unit I stood naked in front of her, quiveringly hard, my dick standing out like exclamation point.
“You should go down on her,” Carroll pronounced, “I want to see you lick that pussy.”
Alice lay down across the bed, spreading her legs wide apart, her neatly-trimmed petite little pussy pointed directly at Carroll. The inner lips were just visible, pouting out like a young tulip not quite yet in bloom.
I’ve always been a little shy about going down on Alice. It’s not like I mind the taste (I actually rather like the way she tastes), but I’ve always felt kind of incompetent at it. Alice always said I do a good job down there, but I’ve never been sure she’s really into it, and I had never made her come that way.
I lay down on the bed on my stomach, put my head between her thighs, and started licking.
She pulled her lips apart for me, giving my tongue access to her moist, slippery bits. I found her taste intoxicating. I licked harder, getting into it, slurping up and down, like a dog at a water bowl.
“Slow down!” Carroll commanded from on high, “Lick her clit! Tease her a little bit!”
I pulled back, spreading Alice’s wet pussy with my fingers. It was almost the first time I had ever gotten a really good close-up look at her sex. Her pussy was beautiful, and sopping wet. Her tiny clit stood up excitedly, hard and pink. I tentatively touched it with just the tip of my tongue, and Alice gasped.
I let my tongue dance lightly around Alice’s clitoris, sometimes brushing against it, sometimes just missing it. The more I teased her, the more excited she got. My dick was rock hard and leaking underneath me.
“That’s fucking hot!” Carroll said, “Now put a finger inside her. Two.”
I did what she said. Keeping the tip of my tongue balanced on Alice’s joy buzzer (as best as I could what with her squirming around), I slid a finger, and then two up her slippery wet pussy. She was hot inside, and her pussy seemed to grasp my fingers. I slid them in and out, finger-fucking her as I teased her clit.
“Three. Put three fingers in.” Carroll sounded hoarse.
It was a tight fit, but I managed to get a third finger up her pussy. Alice was moaning constantly, like a cat in heat. I wasn’t sure I’d ever heard her so aroused.
“Now play with her asshole.” Carroll instructed.
I let my pinky finger slide down into the forbidden zone between Alice’s butt cheeks. My finger found the tight ring of her anus, and gently stroked it. Her pussy was gobbling my fingers, and as I reapplied my tongue to her straining clit, she howled and bucked, writhing and shaking underneath me.
“Fuck! I’m coming! I’m coming!! Don’t stop! I’m coming, I’m fucking coming!”
I stayed with her all the way through her orgasm, and when she was done, I was soaked in her juices.
“Now fuck her!” Carroll said. She had one finger buried in her own pussy up to the knuckle, and I could see the wetness dribbling out of her.
We arranged ourselves as before, doggy-style, so we could watch Carroll masturbate. I slid my dick up Alice’s red-hot pussy, and it felt like heaven.
“That felt so gooood,” Alice whispered back to me, “fuck me good and deep and come in my cunt!”
I knew I wasn’t going to last long. I tried to prolong the ecstasy by going slow. I’d ease my cock all the way inside Alice’s pussy, and then slowly withdraw it until just the head was nestled in between her clinging lips. Even so, I was just hanging on by a thread. It felt exquisite. We could both here the squelching sounds of Carroll masturbating: she was plunging two fingers in and out of her shaved, brown and purple vagina, and she was using two fingers on the other hand to peel back her fat lips and expose her pink little clit.
“Now fuck her in the ass!”
Now that was right out of left field. Alice and I had never done that, never even discussed doing that. I’d never had anal sex. I’d always wanted to try, but I’d never known how to ask.
I waited for Alice to say Yay or Nay, but she just buried her face in the sheets and thrust her rump even higher in the air. I took that for a ‘Yes’.
I pulled my wet dick out of her pussy and carefully parted her cheeks. There it was, her tiny little brown crinkled asshole. It looked so small and delicate; there was no way my cock was going to fit inside. I nestled my slippery cock head up against her anus, and she kind of moaned and wiggled her ass. I looked up at Carroll, who was grinding herself against her fingers, and who grinned down at me.
Very carefully, I took aim. As gently as I could, I nudged forward, and her body seemed to open up and swallow me. Alice kind of grunted and lurched back toward me, and suddenly the fattest part of my dick was lodged in her asshole. Her sphincter squeezed me so tight it was almost painful.
I nudged gently forward again, slipping past the tight ring of resistance, and then I was inside her. Alice sighed, arching her back and pressing back against me.
I felt the orgasm bubbling up from my toes. “I’m going to come!” I gasped hoarsely.
“Don’t come!” Alice whispered insistently, “Please not yet, I want to come too.”
With everything I had, closing my eyes, curling my toes and clenching my ass, I held it back. Alice’s fingers were rubbing furiously on her clit. I kept fucking her ass, slowly, steadily, plunging in and out. Her breathing was getting sharp and ragged, and I knew she was right on the edge.
I slid one finger up her pussy. It was tight, and I could feel my own cock moving through the thin layer of flesh. That set her right off, like a string of firecrackers, and it set me off too. I forgot about being gentle, and started slamming my dick into her asshole, finger-fucking her hard at the same time, as my orgasm roared through me like an express train. We were both shouting and growling and bucking, fucking like wild things, as we came together, and I squirted jet after jet of hot sticky semen straight up her butt.
I guess Carroll came at the same time as us, but I was too wrapped up in Alice to even notice. I think that was the longest, most intense orgasm I’d ever had.
After I’d carefully extracted myself and we’d cleaned up and Carroll had gotten dressed and left, Alice and I were cuddling in bed together.
“Why didn’t you ever do that to me before?” she asked.
“I don’t know,” I said, “I didn’t think you’d like it.”
Fit the Third: The Vanishing
Alice broke it to me over breakfast: orange juice and bacon flavored seitan.
“There’s no easy way to tell you this,” she said, “So I’m just going to say it. I’m leaving.”
It knocked the wind out of me, like a roundhouse punch to the stomach. It hurt, and I felt literally dizzy for a moment as the world shifted on its axis. But at the same time, it was a relief, and it felt like a tight strap around my chest had just been relaxed. I could finally breathe again.
“I’ll be packing my things over the next couple days,” she told me. I couldn’t look at her. “I hope we’ll always be friends.”
Unwashed dishes began to pile up in my sink.
Fit the Fourth: The Capture
I was late. I was already running behind my time, and then the subways were screwed up, and then I was really late.
My dick felt like a lead ingot between my legs, a heavy pendulum swinging back and forth as I walked up their block.
They had a basement apartment in Astoria they called the Rabbit Hole. Carroll met me on the landing at the bottom of the stairs, naked. Naked, that is, except for a strap-on and harness: black on black.
The dildo glistened wet and slick in the fluorescent light of the stairwell. The flesh around the scar on Carroll’s chest was livid and red. “Come on in,” she said to me, “You’re just in time for the main event.”
Her phallus wiggled and bobbed obscenely as she walked. For just a moment, I imagined what it might be like to be bent over in front of that fat black dildo, and it gave me a secret thrill.
She led me into the bedroom, where Alice lay spread-eagled on the bed. Her pussy looked freshly fucked: pouting pinkly open and drooling wet. There were bruises on her wrists and ankles, livid red and purple. Her nipples were erect. She wore a dog collar, fastened with a tiny padlock, and she had a fresh tattoo, still red and irritated, a copy of the classic Tenniel illustration of the Mad Hatter. Instead of a tea cup, he held aloft a large pink dildo, shaped like a flamingo. When she saw me, she smiled and waved.
I got undressed, and sat down in a big purple overstuffed easy chair to watch the show.
Carroll had fished herself out of the strap-on harness, and was busy pouring lube all over her hand and Alice’s crotch.
“Girl’s got a really tight pussy,” Carroll said to me over her shoulder, “I had to loosen it up a bit first.” She grinned. “I am really going to enjoy this.”
She methodically began finger-fucking Alice. One finger at first, then two, then three. She stopped and applied more lube, then worked a fourth finger in. Even though I knew what was coming, I couldn’t believe it was actually going to happen.
It was beautiful to watch. Alice appeared lost in ecstasy. Her pussy opened up to devour Carroll’s invading fingers, wider and wider. Carroll’s face was a mask of concentration as she formed her hand into a duck-bill shape, gently but insistently working all five fingers deeper and deeper into Alice’s wide-stretched cunt.
It was as if we were all three balanced on a razor’s edge. At long last the tension broke. Alice sighed, a long, drawn-out, contented-sounding sigh, and Carroll’s fist slid all the way up inside her, buried to the wrist in her pussy.
“Oh fuck, you’re inside me!” Alice said, her voice trembling, “You’re really really inside me! Fuck me! Fuck me, make me come!”
Carroll starting fucking Alice with her fist: infinitesimally small, meticulous little movements that made Alice writhe and contort. Both women were in a universe all their own. They seemed completely unaware of me, and my skyward pointing, completely erect, oozing dick.
“I’m going to come! I’m going to come! I’m going to come!” Alice squeezed her eyes shut, her face contorted into a grimace. Her abdomen contracted and shook, her nipples turned bright red, and her breath came in raspy little gasps as the orgasm rolled through her.
As the peak passed, Carroll carefully withdrew her hand. Her fingers were absolutely covered with juice, a mixture of come and lube. Alice’s pussy gaped wide open as she rocked through a series of aftershocks. Her clit stood up, tiny and bright pink.
“That was really amazing!” We all three agreed, naked over mojitos, my dick still painfully hard, my balls heavy and tender. The ice clinked in my glass, and the girls kept brushing their naked thighs against mine.
They lay me down on the bed, flat on my back, my cock pointing up at the plaster ceiling.
Alice stooped over me, kissing my lips like a hummingbird while her boobs hung down, her nipples brushing lightly against my own, sending a jolt of electricity through me every time we made contact. Carroll squatted between my legs, insinuating a finger between my butt cheeks.
I jumped and started to protest when she found my anus, but she was insistent, and Alice shushed me, so I tried to relax and let her do her thing. Carroll’s slippery finger felt huge as it probed and invaded my sphincter. It felt awkward, uncomfortable, and oddly erotic.
Suddenly she was inside, worming her way deeper and deeper into the recesses of my body. It felt strange, but not in a bad way, no, not at all. I felt myself squirming to give her better access as she finger-fucked my asshole, and my cock was harder than ever. A big fat drop of pre-come oozed out the end, and ran down the shaft like a tear drop.
“Fuck me, fuck me, fuck me!” I heard myself begging as Alice kissed my lips and tweaked my nipples. A grinning Carroll complied, banging my ass harder and deeper, forcing her finger all the way up inside me.
She started tracing the length of my cock with the fingertips of her free hand, just barely touching me, running her fingers lightly up and down the sensitive flesh as she worked a second slick finger up my freaked-out, hyper-excited asshole, curling and pulling and twisting her fingers inside me.
The orgasm took me by surprise, blindsided me, like a stray jolt of lightning, the kind of flash-BOOM that means you’ve just missed being electrocuted. All of a sudden I screamed out loud, shooting come in a high arc all the way up my chest and onto my chin, spattering Alice on her face. My cock twitched and my asshole spasmed, and I came and came, pumping bucket loads of semen all over my heaving stomach.
Finally I started breathing again. Carroll carefully extracted her fingers from my clenching anus. The girls lapped up the come all over my torso as if it were icing on a fancy French dessert. There was a lot of giggling, all around, and then we all three took a shower together.
It was late late by the time I got back to my cozy little apartment, but I didn’t care. My cock felt thick and comfortably satisfied in my pants, my asshole was still buzzing and my balls were sore. I stayed up for a while, did the dishes, had a beer, lounged on the bed, stretched my legs out and half-studied a book on chess openings.
I might masturbate later on, imagining Carroll in that strap-on, fucking Alice’s pussy. Or Alice wearing that strap-on, fucking my ass while I licked Carroll’s smooth brown pussy.
My snark may have been a boojum, but I kind of liked it that way.