A First Time For Everything

“Are you sure you want to do this?” Chip asked me.

“As sure as I’ll ever be,” I said, feeling surer even as the words came out of my mouth. After all, what kind of tease would I be if I backed out of the bukkake party I’d organized for myself?

It all started with Truth or Dare. I’m a wordy girl and will always pick Truth over Dare, even though I consider myself pretty gutsy. But without truth, without words, without syllables spilling out into sentences, dares don’t make any sense; they’re just reckless actions of the sort performed by drunk boys in late-night race cars, rather than the magnificent grace of a tightrope walker or bungee jumper. I want to be the daredevil superhero girl of sex, boldly going where few, if any, of my peers have gone before. If I go with a dare, it’s of my own making, one that really does push me right up to my limits, not just where an envious partygoer would like to see me go.

The truth is, I’m a thrill seeker. I’m the girl who’s been there, done that, and gone on to relish telling the story over and over again. I’ve had sex with men and women, in groups, in public, in dungeons. I’ve had all manner of sex toys, real and improvised, shoved into my pussy. I’ve been fucked underwater and spanked on camera. I’ve said yes to things simply to shock other people. I’ve used a violet wand, a Magic wand and a TENS unit. I’ve had all my toes shoved into a greedy bottom’s mouth, and I’ve sucked two cocks at once. I’ve made a girl profess her love to me the first night I met her, all because of the way I wielded my fist. I’m only twenty-four, but let’s just say I get around. I prefer being single because it gives me room to play the field without worrying about hurting anyone’s feelings. I like to come home at six a.m. once in a while, do the quick two-hour catnap, shower, and change, using the memory of the night before to fuel me when the lack of sleep threatens to kick in. I’m the one my friends call on for advice, even referring me around to curious but shy friends: “Oh, call Caitlin, she’ll know.” Yes, that’s me, the girl who’s done just about everything (and everyone), whose little black book is actually a massive journal scrawled with names and stories and phone numbers and Polaroids, a glorious jumble of limbs and cocks and breasts and lips, ones I’ve never sought to try to untangle into a neat, chronological history.

Sex has always been the starting point, never the end, to any inquiry about who I am. It’s the gateway drug to, well, more sex, to finding out more about how I operate, what buttons I like having pushed and which I set permanently to caution. This utterly carnal lifestyle is balanced by the hours-days-weeks-years’ worth of fantasies that must jumble together until I’m compelled to act. I’m not just an ethical slut; I’m a thoughtful one, too. The time I spend thinking about sex, pondering its every nuance and possibility, far exceeds the time I spend engaging in it, and I’m perfectly happy with that uneven ratio.

So when Sally asked me what my deepest, dirtiest, darkest fantasy was during what had, up till that point, been a rather tepid game of truth or dare (bra size and taking one big bite of everything in the refrigerator among the highlights), I told her—and the whole room. “I want to do bukkake. I mean, be on the receiving end. I want to be lying naked on the floor and see a circle of cocks, all pointing at me. I want a round of boys to want me so badly they’ll get naked in front of each other, press their dicks up in my face, while I beg them to come all over me. I want them to take turns shoving their cocks down my throat, slapping them against my lips, rubbing them on my skin, in my hair, doing whatever the hell they please. Maybe I’ll be tied up, though then that would deprive me of the pleasure of giving two hand jobs at once. I don't know exactly how it would work, but it’s been a mainstay of my fantasy life for years.”

I paused, mentally highlighting my vision in my mind where they all started to spurt at once, barely giving me a chance to open up and say, “Aah.” I swallowed hard and blinked rapidly, trying to get back into the present. “Yeah,” I finished quietly, breathless, my eyes closed, almost ready to cry. Some fantasies are too primal, too out there, too real to ever admit—even to ourselves. But it was true; just thinking about all those anonymous cocks close enough to taste, close enough to smell, close enough to swallow, had my panties soaking wet.

I wasn't the only one who was intrigued with the idea. Everyone started asking me logistical questions, their eyes lit up, the tension in the room palpable, but I shushed them. “It’s just a fantasy. You asked for the truth and you got it. If you really want me to go through with it, catch me next time I say ‘dare.’”

I didn’t mean to sound so haughty, but then again I hadn’t meant to reveal something so intimate when everyone else was only sharing the most superficial of details. I hugged my arms to myself, beyond blushing. What does it say about a girl that she dreams of jizz raining down her face, dreams of being a sex object in the most extreme fashion in the way that some girls dream of getting married? What does it say about me that after I went home, the idea just wouldn’t go away? I’d thought it was one of those fantasies that could never come true, and even if it could, that it would be pushing things, even for me. Whoever heard of women willingly submitting to bukkake outside of porn? Maybe gay men, but that was okay. They’d be pigs among pigs (in the best possible sense of the word, of course). But who would I be in such a scenario? Could I ask men to degrade me and respect me and get off on me, literally, all at the same time?

Apparently I could, because my gay friend Chip called me the next day and tried to sound casual about bringing it up. “God, Caitlin, when you said that, everyone in the room got a hard-on. Even Mikki,” he said, referring to our most vanilla, conservative friend, who just happened to be a lesbian (but would never call herself a dyke). “Seriously. It wasn’t just that we were getting off on the idea, but your voice got so breathy when you said it, like you were literally seeing yourself doing it in your head, not just spouting off some story you tell all the time to impress people.”

“Thanks, I guess,” I said, wondering what kind of can of worms I’d opened up. “But it’s nothing, really. It’s a fantasy.”

“But what if…?” His voice trailed off.

“What if what?” I hissed.

“What if you could actually do it? What if I found you hot, straight guys—big cocks guaranteed—who were into it? I’d so do that for you. All I’d ask is that I get to watch.”
“Whoa, whoa, whoa…slow down there. You? Watching me? And where would these guys come from?” I was supposed to be suspicious, supposed to protest, but I was intrigued and knew from the pounding in my pussy I wasn’t going to stop the thoroughly filthy path this conversation had taken.

“I know people, Cait, guys who’d love to jerk off over your pretty face.”

“Like who?” I just couldn’t imagine anyone we know would actually volunteer for such a task, in the presence of other guys.

“Rob, for one.”

“Rob? Hot Rob? Really?” My nipples hardened at the thought of bodybuilder Rob, always so brooding, silent, and hunky, being naked before me. I’d tried flirting with him in the past, but he seemed so stiff and quiet.

“Yes, Rob. I already asked,” he said.

“What?” The word came out as a yell, but inside I was starting to get totally wet.

“And Rob can bring Jeremy and he said he has at least two other friends who are interested. They’ve all been tested and are single, so there’ll be no jealous girlfriends butting in. And I have another friend, Omar, who wants in on it. I’ll arrange everything; you just have to show up.”

“Really? You’d do that for me? I mean…” I trailed off, not really sure what I meant since I’d never been in a situation remotely like this one before.

“Really, Cait, trust me. And it’s not for you. Well, it is, but it’s for us, too. Believe me.” We hung up and I slid beneath my quilt, letting my fingers plunge deep inside my wetness as I contemplated saying yes to making my fantasy come true. The answer was obvious.

I wound up letting Chip plan the whole thing, and when he was done in a week’s time, he had five guys willing and eager to cover me in their come. It wasn’t quite the dozen-man orgy of dick I’d fantasized about, but the fact is, we live in New York, and a twelve-cock circle jerk along with spectators, and me, would probably have been too much to ask for. Five was manageable, a nice albeit odd number, just slightly above four, which was still a respectable configuration. What we were about to embark on could even be called a sixsome, if that’s a word, I told myself, and then Chip.

“Caitlin, let’s face it. This is your big slutty night. Whether it’s five or fifty cocks, it’s still bukkake. Be proud, girl! Everyone I’ve told about this is totally jealous. You’re gonna have the time of your life; don’t downplay it. This is your chance to live out a fantasy you never thought you’d get to.”

He was right. As his words burned in my ears, I went about cleaning up for what promised to be the party to end all parties. I had a few days, but I’d need them.

---

The night of the party, I was the perfect host. I prepared a spread of hors-d'oeuvres, light snacks like veggies and fruit, some chips, some candy, and laid out soft drinks and a few beers, though I kept the alcohol light. I offered plenty of lube, flavored and not, condoms, in case one thing led to another, and some sex toys, including handcuffs. I’d thrown in the restraints I sometimes get shackled to my headboard with. Yes, I’d decided to do it where I’d be most comfortable, on my bed. Chip was there to oversee things and to get off on the spectacle. “What about this?” he asked, rummaging through my toy chest as only a gay man can, coming up with a red blindfold my ex had gotten me years ago. I didn’t even know I still had it.

“But I want to see all those cocks,” I said, already picturing the guys wanking away just for me. That was the part I liked the best; the men wouldn't just be jerking off, they’d be doing it with a purpose. I’d be the center of attention and get to feel wave after wave of hot come splashing across my face. I’d always loved the depravity of shutting my eyes and submitting to that most intense of sensations. Even more than swallowing a lover’s spunk, having him grace my cheeks, lips, even my hair with it made me feel at once worthy and degraded. I’d had lovers refuse to do it, unable to see me as the filthy whore I sometimes longed to be. One ex had chickened out at the last minute, able to paint my breasts creamy white but otherwise wanting to come only on my insides, not my outsides. Knowing men were being handpicked for this activity, men who’d want to be there, who’d know just how much I wanted it, was a truly special thing to contemplate. Utterly perverse, utterly fucked up, and utterly arousing all at once, all the more so because they weren’t just horny beasts off the street but men I admired and respected enough to welcome into my home to defile me. Unless you know the thrill of pure submission, those two things may sound like opposites, but believe me, they’re not. It takes a special, enlightened, intelligent kind of man to treat a slutty girl like me just right.

“Well, I’d recommend keeping the blindfold handy, both for you and for them. They may not be able to go through with it with you staring up at them. Plus think about how your other senses will be enhanced by not being able to see.” I shut my eyes and pictured myself surrounded by cock, pure cock. We were expecting the five guests who’d RSVPed, so that would be five dicks, five sets of balls, and hopefully five hot blasts of come streaming over my lips and the rest of my face. It was like a gangbang, but even better.

“Okay,” I whispered, already feeling my body respond to the mere thought with an intense ache.

What does a girl wear to her very own bukkake party? I pondered, flipping through my closet and then my dresser drawers. Nothing seemed quite right, considering, but I didn’t want to answer the door naked. I settled for a simple, sheer nightie in mint green, and almost as soon as I’d put it on, the doorbell rang. Chip had been urging me away from my makeup, against my natural instincts (how could I host a party with a bare face?), but now the doorbell had decided it.

The first guest to arrive was hot Rob, wearing basic jeans, sneakers, and a white T-shirt. He’d brought a friend who could’ve been his twin. Both were equally delectable.

“Welcome,” I said, giving a small smile to the newcomer and a flirty wink to Rob. “I’m Caitlin,” I said, sticking out my hand.

“Joe,” he said, reaching forward and enveloping me in a hug. My body responded to his sheer size, and I wondered if his cock would match his heft.

Rob seemed to want in on the hugging action, and as soon as Joe put me down, he swept me up. “You look beautiful tonight, Caitlin,” he said, possibly the longest sentence he’d ever bestowed on me.

“Rob,” I said, smirking slightly, “you don't have to butter me up, you know. I’m a sure thing, tonight anyway.”

“Look, I know that. And if you want the truth, I’m a little nervous. I’ve never been in a room full of cocks before.”

“Well, if it makes you feel any better, neither have I,” I said. Well, that wasn’t strictly true; I’d been to orgies and sex parties where naked couples abounded, but none where I would be so close to dick, and I couldn’t wait. “And…I’ve been especially looking forward to seeing what you’ve got under there,” I said to him, lightly running my fingers over his package. He stirred beneath my touch and as a reward, I lowered the nightie so my boobs popped out. Rob leaned down and began sucking one nipple while I moaned. The doorbell rang, but I figured someone else would get it. I wasn’t sure about proper bukkake party etiquette, but that seemed like an oxymoron if I’d ever heard one.

We continued to kiss and fondle each other, and I just shut my eyes and focused on Rob. That lasted all of a minute or two, until Chip was pulling me aside. “Save some room for the main course,” he whispered. I giggled, then winked at him as I twirled around before clapping my hands and calling everyone to attention.

“Okay, boys, I guess we’re ready to get started. I just want to thank you all for coming (ahem) and tell you how excited I am.” With that, I paused and made eye contact with each of the men whose cocks were soon going to be right up in my face. “The only rule I have tonight is that we’re all here to have fun, and I want to make sure you’re all comfortable. Does anyone have any questions?”

One guy, Jaime, raised his hand. “Can we come anytime we want?”

This was something I hadn’t considered; I’d sort of assumed that they’d all jointly have the urge to splatter me with their jism… just like in the movies. But the question also granted me the power to answer, and thereby control his orgasm, and my pussy responded to this unexpected opportunity. 

“No.” I looked directly into his eyes, then walked toward him, reaching under his shirt to twist his nipple. He whimpered, and I smiled. “No, Jaime, you’re all going to come when I tell you to. Just because I’ll be lying there aching to suck, lick, and feel your cocks doesn’t mean I’m not in charge. If you want to stay at the party, you’ll have to learn to wait.”

The collective mood in the room went from excited to practically orgasmic as we all realized that this wasn’t a prank but that we were all about to engage in something we’d only dreamed of. “Okay, then, I’ll give you a few minutes to get naked. I’ll be right over there,” I said, pointing to my room. I wasn't sure how they wanted to handle that process, so I let them be while I slipped out of my lingerie and looked down at my naked body.  The slight curve to my belly felt sexy, and I slid my hand down over it to my mound, which sported just a few tufts of pubic hair.

I walked over to my bed, the scene of the crime, as it were, and lay down on my back. Chip placed the blindfold and a bottle of water near me, then kissed me on the cheek. “All those cocks are soon to be yours,” he whispered to me, and I opened my eyes long enough to see that his own cock was extremely aroused. I began playing with myself, lightly stroking my clit, then running a finger along my slit, trying to be patient. As I glanced at the men as a group they ceased to be individuals distinguishable by voice and looks and conversation. They were all equal, their cocks together forming a whole that would transport me into another dimension, or so it felt. I let myself sink fully into that fantasy, losing whatever shreds of propriety I was clinging to in order to make the most of this momentous opportunity, for that is what it was.

The first man to saunter over was Jaime, and I immediately felt a frisson of arousal as I looked at his cock. It was already hard, and fat and delicious-looking. I smiled at him, then rolled over to the edge of the bed, turned onto my side, and brought my mouth within sucking distance by way of greeting.

Without saying a word, he offered me his dick. Well, the head of it, anyway. His fist was wrapped around it and he fed it to me slowly. As I took the rounded tip in, then let my lips move down over the crown, I shuddered. Nothing makes me more aroused than wrapping my mouth around a man’s hard cock. Today it didn’t matter whose cock it was or what he thought of me or even how he was feeling. For once, it was okay for it to be All About Me, though I was sure the men would enjoy themselves as well. I immediately had to keep stroking myself as I swallowed Jaime’s cock, his hardness making me frantic. Before I could really start bucking up and down though, he wrapped his fingers in my hair and pulled me away. His forcefulness combined with my now-empty mouth turned me on even more.

“Baby… if you want me not to come, you can’t suck me like that. I’m only a man, after all,” he said, taking a step back. I looked up at him, begging with my eyes, running my tongue over my lips, but he shook his head, seeming to take delight in withholding it. “Later,” he murmured, and when I turned onto my back, I saw that another man was next to him and three more on my other side, perched on the bed so they could be close enough. They were each stroking their cocks, almost tentatively, as if waiting for a cue from their comrades that they could go faster. I’d given up trying to distinguish whose cock was whose, because at that moment it just didn’t matter.

I moved so I was facing the trio, my back toward Jaime and his pal. I opened my mouth and two men brushed their cocks against my tongue. I looked up and all I saw was dick, dick, dick, literally, as another one appeared near the others, trying to get inside, though as talented a fellatrix as I am, that would’ve been impossible. I could hear heavy breathing and pumping on the other side and Chip clapping in delight. “Give it to me,” I said, stretching my mouth as wide as I could so those first two cock heads could fully enter my mouth.

This was much farther than I’d ever gone before, for even the largest cock I’d swallowed, and there had been some that had made me truly stretch my mouth, gag, and strain, didn’t come close to having two dicks jockeying for position. Soon I pulled back and kissed the three tips. I took the dildo I’d placed beside me and began working it into my pussy. I had lube nearby, too, but found that I didn’t need it. I knew this wasn’t the traditional version of this kind of gangbang, where the men’s pleasure was paramount, but since I’d orchestrated this scenario, I wanted to reap the rewards. Far from being humiliated, I was overjoyed at getting to arrange this affair to my exact specifications, and the wetness I found between my legs proved it.

I was torn between closing my eyes and focusing on the feel and smell of so many cocks and seeing them in action. I sat up on one elbow, dildo inside me, and we all jerked off communally, grunting and grinding, hands flying over skin, slamming and jerking, violent words for harsh actions yielding dizzying results. I’d always found it to be true that a light touch may as well be a tickle; I need firm, steady pressure, and gazing upon these men with cocks in fists, apparently they did, too.

Under my observation, the men seemed to jerk their cocks faster, moving in sync almost. Someone crawled behind me and I lowered my head down to the sheet so his penis could rub against my forehead. That gave the others entrée to slide closer, hover directly on top of me, and slap their dicks against my face. I fucked myself with the dildo, wishing I had a vibrator because soon my hips were rising and crashing down against the mattress, my eyes tearing in ecstasy as all those penises suffused my senses. I turned my face slightly to the left and took the nearest dick into my mouth, easily swallowing its long, swollen length. Just then, I felt the first jet of cream land on my back, and I whimpered as best I could with a mouth full of cock. I looked up into the eyes of Rob, and he cradled the back of my head gently in his hand as I sucked him. This may sound crazy, but it felt spiritual to me, a moment of bonding that went far beyond the mechanics of sex. Or maybe I’m just the rare girl who can have a holy moment with five gorgeous cocks surrounding her.

I gave everything I had to Rob, slamming the dildo so deep inside me it bordered on pain, the best kind of pain, as I let him invade my mouth. I’d wanted this invasion, asked for it, negotiated it, and now I delighted in it, all of it. I moaned against his mouth, urging him to come down my throat, and my man of the moment obliged. The stream of hot liquid surged into my mouth and I swallowed, my cunt contracting around the dildo at the same time. Rob’s release freed me to lean back and simply let the men take over. I surrendered to the glory of this unique situation and watched as one, then another, then yet another dick let loose until I was coated in sticky, white, beautiful come. I reached up and smeared it all over my face, and kissed whoever’s lips moved forward to kiss mine. I didn’t want to get up just yet; this sex spell was too beautiful to be broken. I lay there and smiled up at my suitors, my good-time guys, my bukkake boys, a grin covered with come, basking in pure bliss. It sure beat the hell out of most of my other sexual firsts. Chip winked at me, and I winked right back, reaching out my hands for whoever wanted to grab them.

This story was originally published in X: The Erotic Treasury, edited by Susie Bright.