One is an absolute monster. I pick it up. It’s heavy and more than fills my palm. “Bloody hell, now that one is definitely scary.”
“I know. I was a bit horrified when I opened the parcel. But the little one’s fine.”
I pick up the other one. It’s still weighty and a serious size, but not off-the-scale huge. It warms quickly in my hand. I start to imagine sliding it inside him, but I make a spur-of-the-moment decision. “I want to watch you put it in. When we get a strap-on, I want that to be the first time I put something in there. I think it’ll be better that way.” I can be patient. I can wait so that the first thing I push inside him is my special pillar-box red cock.
Ryan goes to the bathroom to take the other one out, then positions himself kneeling on the bed with a tube of lube and the medium plug. I lean my butt back on a chest of drawers and find that my hips are pulsing just a little inside my slouchy weekend sweatpants. He rubs lube all around his opening, then pushes a finger inside. He spreads more on the plug and presses its tip to his asshole. It is such a sweet sight. And thoroughly obscene. It slides slowly inside as Ryan breathes hard.
“What does it feel like?”
“Big. Fucking big,” he murmurs, pausing its inward journey. He gathers himself for the final push. “It feels amazing actually. It’s all wrong, something going in when all the muscles want to push it out. But I can’t believe how good it feels once you relax around it.” His hole is stretching over the widest part and he groans a little as it slips in and settles into place. “The first time I tried, I put my hand on my cock and before I knew it I was coming.”
“Come now. Come in me with it in you.”
As Sunday mornings go, that one ranks pretty highly. But when the next one rolls around, it’s time to up the ante. After he’d fucked me on the new rug, struggling to keep from coming too soon with the object in his ass upsetting his usual equilibrium, I subtly persuaded him about the strap-on we would buy and we placed our order. Two days later, it arrived in a discreet brown parcel. But we decided to wait for the weekend. For Sunday morning, when we have nowhere to be and no visitors expected.
I take the webbing contraption out of its box and work out the straps, pulling it up my legs, feeding the dildo through the holder and buckling everything into place. I’m otherwise naked but Ryan, sitting on the edge of the bed watching, is mesmerized not by my tits or pussy, but by the red tip of my cock. I stroke my hand up the shaft and his feet fidget. I step up to him and thrust it toward his face. He leans down and puts his lips around the end. Instant power. I want to push it down his throat until he gags.
“I’m going to fuck you senseless,” I tell him while it’s deep inside his mouth. He moans his assent and then his disappointment as I pull it out. “On your knees on the rug.”
He hesitates before sliding down onto the floor. For a moment I think he’s going to say something. Does he want to make a speech to mark this momentous occasion? Or express last-minute doubts? I want to thrust it in him so quickly he can’t change his mind. But I need to make sure he’s sure. If he changes his mind, I’ll just have to live with it. My fantasy has only recently become his and it would be quite reasonable for him to have second thoughts.
I kneel behind him. “Are you okay with this?”
He’s on all fours on the rug and when he turns his head to me it’s just like that first time I saw the plug in his butt. But this time his voice is less assured. “I’m a little, um, apprehensive. Yeah, that’s the word. Part of me is wondering how the hell I got myself into this position.”
“The dildo is slightly narrower than the medium plug,” I assure him. “I’m going to take it very slowly, and it’s not going to hurt.” He’s been wearing the medium plug every evening since last Sunday.
“Just be gentle,” he says. “It’s one thing putting a plug in yourself. Letting someone else fuck you…” He trails off.
“I’ll be gentle.” I want to say something momentous myself. That I’m honored to be popping his ass cherry, perhaps. But I don’t want him to get any more worked up. I squirt lube into my hand and massage it all over my dick. I place my hands lightly on his asscheeks to begin with, then start to circle my thumbs into his crack, spreading more lube toward his hole. I’ve spent the last week picturing to myself what it’s going to look like when I press the tip of my cock to that puckered hole and ease it inside him. And now I’m so close to fulfillment. My throat is tight and my pussy is wet.
It’s not just that he’s handing me control and letting me play out my fantasy on him. It’s the fact that he wants it. He’s offering himself up to me in the most intimate way possible, and I can see from his eyes that he wants it as badly as I do. That look powers all the way to the muscles I’ll be using to thrust inside him.
When I’ve spread the lube all around him, I slip the tip of a finger inside, waiting for his sphincter to relax and let me in. I slide it in and out, easing him open, and push in a second finger. He rocks his hips back onto me, breathing hard. His back and butt are damp with sweat already. Inside, his ass is hot and moist with a texture I know only from the times I’ve stretched to put a finger an inch up my own butt while masturbating. That damp, woolly feel. I’m already awed at having my sensitive fingertips pressed inside my husband, but it’s time to put my cock in there. I slide my fingers out.
“Part your legs a little.” I can’t reach otherwise. I have to kneel high to bring the tip to the right place. He’s suddenly desperate, skittish, squirming into position too quickly, turning to try to grasp the dildo and pull it into himself. I place a hand on his hip. “Relax.”
The butt plugs have paid off. I push my cock against him and I see his ring loosen and push outward as he opens up for me. The shaped head disappears inside. I realize I’m holding my breath and let it out as I ease the shaft gradually in. Just once, Ryan’s ass tightens and his shoulders tense. I see the rug wrinkle as he grasps it. But he calms himself and starts to moan low with each out-breath.
The flared shaft stretches his hole wider, excess lube rippling at his opening as his taut skin skims it off the dildo’s surface. I’m panting as I push in the final inch and rest the strap-on’s frame against his body. “I’m all the way in.”
It’s Ryan’s turn to let out a trapped lungful of air. He drops his head toward the rug, accentuating the animal strength of his shoulders. I pull my cock slowly back until I see the beginning of the head one inch from the end. I slide it back in and begin to fuck him slowly. I watch the thin, wrinkled skin of his asshole glide in and out along the dildo. I’ve imagined what this moment was going to feel like, but am completely unprepared for the intensity of the experience. He’s mine. I’ve bent him over and penetrated him and now I’m going to fuck his brains out. I have my cock deep inside him, pounding him, and from the sounds he’s making, he’s loving it.
He rocks his ass in time to the fucking, slamming up into the base of the dildo, inviting it to hammer into him harder and faster. I grasp his hips tightly to help me pound him deeper. I’m hot and sweating from the exertion. Webbing teases my labia and rubs my own asscheeks. My thighs ache and my knees are getting stiff.
Ryan’s moans change. He’s struggling to say something, muffled against his forearm. “I…I…” I smile at the realization that I’m fucking him into incoherence. “I’m going to come,” he eventually stammers out. I only hear the F of the next word, as a deep groan of satisfaction rips the curse from his throat. I can’t see his cock, but as that groan tails off I know it’s time to slow down. I come to a rest halfway in.
“Fuck.” He eventually manages to complete the word.
“Yes,” I agree, my hands resting on the top curve of his butt. “Fuck.”
I let him catch his breath. “I’m going to come out now,” I say. “Breathe deep for me.” As he sighs, I pull my cock out, watching his hole tighten over the tip and pulse as it empties.
I stand and slip off the straps, kicking them over my feet. Ryan hasn’t moved.
I sit down beside him and let him rest his head on my thigh. “Honey,” I say, “You’ve come on our new rug. Hand woven by Berber nomads. It’s one hundred percent wool. Dry-clean only.”
Ryan looks up at me without raising his head, like he’s completely spent. “I honestly couldn’t give a shit right now if it was hand woven from moon dust by little green men.”
I watch the puddle of come slowly sink into the wool, knowing that a quick dash for a towel could mop up the worst before it’s all absorbed. It’s only a rug.
A FIRST TIME FOR EVERYTHING
Rachel Kramer Bussel
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 a tease would I be if I backed out of the bukkake party I’d organized 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 and a Magic Wand and a TENS Unit. I’ve had all my toes shoved into a greedy bottom’s mouth, and much more. 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 coming home at six a.m. once in a while, doing 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, tidy 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 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 amongst 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 the vision in my mind where they all started to spurt at once, barely giving me a chance to open up and say, “Aaah.” 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.
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 on 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 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 amongst 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, referencing 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 block the thoroughly filthy path this conversation had started down.
“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 five-some, if that were a word, I told myself, and then Chip. “Caitlin, let’s just 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.
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