by Penny Wylder
“Fuck yes you dirty little girl, take me all the way inside you. Take every inch of my thick cock. You feel that?”
I moan.
“You like that dirty girl? You like me stuffing both your holes at once?”
I reach up to cup his ass and pull him against my face in response, ramming his cock against the back of my throat again. He groans, a low sound, so guttural it almost sounds like a growl.
We’re close. I can feel it. My whole body is tense with the need to orgasm, and I can sense Caleb’s abs flexing in response for his own. I want it, so fucking badly. I want to taste his cum. I want him to come in my throat while he’s stuffing me full like this. I clench my fists tight around the muscles of his rock hard ass.
But just when we’re almost there, he pulls back. I gasp in protest as I lose my grip on him, and his cock drops out of my mouth. He steps back, away from me, leaving me on all fours, hips still against the wall, the dildo still deep in my pussy.
I was so fucking close. Dammit.
Caleb smirks at me, like he knows exactly what he’s doing. He does, I’m sure. “Did you think I’d let you finish that easily, Carmine?” He shakes his head, tsking a little, as if he’s disappointed.
Then he crooks a finger to me. “Come here.”
I hesitate. Slowly, I crawl away from the wall. The dildo pops out of my pussy with a slick wet sound, and his smirk widens.
“Enjoying yourself, were you?”
I swallow hard and manage to nod.
“Don’t worry. We’re only just getting started.” He tilts his head and eyes me, as though planning his next move. It makes my belly go tight, wondering what he could be planning. What he’ll do to me next. There are plenty of options given my collection of goodies. But somehow, I have a feeling whatever he does, I’ll be surprised.
“Turn around,” he says. It sounds even more commanding and sexy in his accent. The accent I can’t get enough of. If he never stopped talking once, I’d be happy.
Heart in my throat, my pussy still soaking wet and my clit oh so fucking heavy with lust, I slowly turn around on the bed, until my ass points in his direction. I lean forward, expecting him to fuck me from behind. “Did you bring condoms?” I remember to ask.
He laughs. “Of course. But we’re not quite there yet, Carmine…”
Then I feel his warm, thick hands parting the cheeks of my ass. I dare a peek over my shoulder, quivering with anticipation. Is he going to stick his finger up my ass?
That’s when I spy the anal plug in his hand, and my eyes go wide.
He picked the thick one, the one I’ve only just started to practice with. The end is thicker than his fingers, and he has thick fingers to start.
As if reading my mind, Caleb reaches past me for the dresser and grabs a bottle of my lube, the warming kind. He pops the lid and slathers it across the head of the plug.
“You told me you wanted to be stuffed, didn’t you dirty girl? Are you having second thoughts?”
Despite the tension in my throat and the way it makes me knees quiver—hell, my elbows too, in this position—I shake my head. “No way in hell. I want you to stuff me so full I’m screaming, Caleb.”
His grin widens. “There’s that filthy mouth.” He places the head of the anal plug at the tight little pucker of my ass. “You’re going to have to relax again. Unless you want this to hurt…”
I take a deep breath and spread my legs a little wider, willing myself to let go. To surrender to him. Caleb is in charge now. He’s in control, and my body is his plaything. I’ll do whatever he wants me to do.
No guy has ever made me feel like this before.
He pushes the tip of the plug into my ass and I gasp, eyes going wide. Unlike the beads, the plug is a constant, slow, stretching sensation, increasing with every centimeter further that Caleb presses it into my ass. He doesn’t slow down, but doesn’t go too fast either. He gives me time to breathe in deep, adjust to the sensation as, inch by inch, he stretches my ass wider.
Then, without warning, his other hand slips between my legs to cup my pussy. He spreads my lips and circles my entrance, swirling his finger around in my juices, coating himself nice and well. I moan with desire, unable to help myself, as he keeps pressing against the plug, driving it farther into my ass.
“God you are so fucking filthy, aren’t you?” There’s a soft approving sound in his voice, along with that throaty white-hot desire.
“No one’s ever taken me like this before,” I manage to gasp between rotations of his finger.
He laughs softly. “You haven’t seen anything yet, dirty girl.” He presses his index finger into my pussy, and I cry out loud at the feeling of both my holes being filled at once.
It doesn’t last long. He draws his index finger straight back out again, somewhat to my disappointment. But then he circles it across my clit, making my knees lock and my body shiver.
My clit is already sensitive as hell from the spit-roasting earlier, and from how fucking hot Caleb makes me. It only takes a few slow, masterful rotations of his finger, pressing just the right amount, to bring me quivering to the brink of an orgasm.
“Fuck,” I hiss between my clenched teeth. “I’m going to come.”
“Come as I push this plug all the way inside your ass, Carmine. Come for me.” He keeps pressing, keeps swirling his index finger, and at the same time, he gives one last hard push against my ass. The plug glides the rest of the way into me with a pop, stretching me to my limit.
My mouth falls open, a guttural cry escaping as I hit my orgasm. It washes over me in a wave, the searing pleasure mingled with the pain in my ass of the stretch, the plug hitting home.
I’m still shaking from the force of that orgasm when I hear the sound of a condom wrapper. In no time at all, I feel the bed shift under me as Caleb kneels between my legs.
Then I feel the press of his cock at my entrance, his fingers spreading my pussy lips wide to give him access.
I gasp and tense, realizing he’s going to fuck me with the plug in my ass. No man has ever done that before. Not even when I asked—practically begged— my exes. They worried it would be too painful, too weird, too kinky. They didn’t understand.
Caleb does. Caleb is as filthy as I am.
“I’m going to fuck you, Carmine,” he murmurs, that accent of his making the words even sexier than they already are. “I’m going to fuck you with your ass already stuffed. I’m going to stretch your tight little pussy so fucking wide.”
I moan with desire. “Fuck me, Caleb. Fuck me so fucking hard. Fuck me until I can’t walk straight.”
He laughs, a low, throaty sound. “Oh, don’t you worry about that, Carmine.” He reaches up to caress my cheek with one hand. His finger leaves a sticky trail across my cheek, still wet from my pussy. “You’re going to have trouble sitting down tomorrow, let alone walking.”
With that, he thrusts into me, deep, all in one shove. My pussy is so wet he glides all the way into me, and I scream out in sheer pleasure as his cock stretches my tight pussy. I can feel the plug deep in my ass still, and the thick girth of his cock straining at my pussy walls.
As I cry out, he slides his finger into my mouth. “Suck it,” he commands, and I clamp my mouth around his finger instinctively, tasting myself, my juices mingled with the sharp salt flavor of his skin.
He pulls back to thrust inside me again, keeping his finger in my mouth at the same time, his other hand clamped tight around my hip to hold me in place. I lick and suck at his finger, thirsty as fuck, while he builds up his pace, starts to fuck me in earnest.
“Fuck, Carmine,” he growls. “You fucking like that? You like my cock inside you?”
I moan into his hand, and he adds another finger to my mouth, then a third. As I lick and suck his fingers and thrust back against his cock, making the anal plug bounce inside me, I feel like I’m being fucked by three guys at once, every end satisfied, as full as I can be.
He shifts his hips, angles his coc
k so the head drags along my inner front wall, and I cry out again, the sound muffled by his fingers deep in my mouth, as he thrusts against my G-spot. A few more thrusts and I’m already at the brink again, my clit still sensitive from my earlier orgasm, my pussy straining to accommodate his girth.
He can tell. “That’s it, Carmine,” he murmurs. “Come for me again. Come for me, you filthy girl.”
I scream with the force of the orgasm that hits me. He doesn’t slow down, doesn’t even pause in his thrusts. His cock keeps driving into me, sending me over the edge, and making the orgasm last, my knees shaking, my belly tight, hands quivering.
Then he lets his fingers drop from my mouth, and I suck in a deep gulp of air, trying to catch my breath.
But he’s grabbing my hips with both hands now, driving full-force into me, and I realize he’s about to come too.
“Fuck yes, Caleb,” I cry over my shoulder. “Fill me up. Fill me up with your fucking cum, come inside me.”
He growls and fucks me harder, so hard I can hear his balls slapping my pussy lips. I’m pretty sure my ass is going to bruise where his hips crash into mine, but I just push back against him, thrust as hard as I can against him. With a roar, he comes hard, still fucking me. I squeeze my pussy tight around him, milk every last drop as he thrusts away.
Finally, he slows, then stops altogether, his dick still deep in me. I squeeze my pussy again, and he gasps, his cock twitching inside me. He lets go of my hips, slowly draws his cock out of me. There’s a rush of my own juices, spilling down my inner thigh as he slides out of me.
I collapse forward onto the bed. I listen to the rubber snap of him rolling off the condom and tying it. Then he falls beside me a moment later, one hand resting on the plug in my ass.
“Oh, I can…” I reach for it, but he catches my wrist and folds my hands in front of me.
“Relax,” he commands yet again. And with a soft popping sound, he draws it straight out of my ass. Before I can make a move or offer to do anything, he’s already up off the bed, heading to the bathroom to take care of that and the condom. I’m not used to that. Not used to sharing my toys—or having help after everything is said and done. It’s nice to have someone else here. Someone else to come up with the ideas, someone else to take care of me at the end.
Not to mention someone else whose backside I can ogle while he does it. I smirk as I drink in Caleb’s sexy ass, and the sharp muscles of his back, almost as sexy as that V-cut on his front.
Then I roll onto my back and stretch. Before I even finish, he’s already back, lying beside me to wrap his arms around my waist.
“Shit,” I murmur, curling into his side. “That was…”
“Fucking hot as hell,” he murmurs, leaning down to kiss my temple.
“Yeah,” I manage. I’m not sure how else to sum it up. I’d fantasized about this for so long—finding someone as kinky as me, someone who was into my same fantasies. Someone who’d be willing to get down and dirty with me. Not to mention have some fun with my toy collection.
But I never imagined it would feel like this. So comfortable, so easy. My other boyfriends or hookups would all act horrified when I told them about my kinks. If they let me talk them into trying anything, I still felt like a freak, a dirty weirdo who was corrupting them, or totally insane for wanting any of this.
Caleb, on the other hand, is just as filthy as I am. Maybe more so. And he doesn’t care. He doesn’t judge me for who I am. On the contrary, he seems to fucking love it.
“Is it always like that?” I ask softly, curious. Is this how clients and escorts always feel?
If so, I can’t say I blame people for hiring escorts. This is so… comfortable. So relaxed. He liked everything we did. Was into everything I was. Didn’t judge me, in a way no one ever has. He just tried it all, no questions asked. Hell, he was enthusiastic about it.
“Fuck no,” he murmurs, his voice low and sleepy.
I swallow hard. What does that mean? Is it usually better? Did he enjoy himself as much as I did? It certainly sounded like it. But maybe I was wrong.
Before I can work out a way to ask what he means, though—to ask how this time was different—the tone of his breathing shifts. It goes deep, even, and his chest rises and falls against my ear in a soothing, relaxing rhythm. It lulls my eyelids into going heavy, my own breathing into slowing.
Without even realizing it, I nestle closer to Caleb, his warm arms still wrapped around me. I fall asleep with the sound of his breathing in my ear, his scent wrapped around me, and the faint, pleasant tingling sensation in my body of being totally, completely satisfied.
5
I wake up feeling like a million bucks. Even the usual shrieking tone of my alarm clock doesn’t unsettle me. It sounds better today, more manageable given how fucking great I feel.
My body is sore as hell, yes, but it’s the best kind of ache. A bone-deep feeling that tells me I’ve finally found someone who can really, truly satisfy me. Give me everything I want—everything I ever imagined and then some.
I stretch, luxuriating in this feeling, the warm, pleasant glow that suffuses my whole body.
That’s when I realize, stretching feels way too easy.
I roll over and find the bed beside me still warm, Caleb’s scent still on my sheets. I crack one eyelid and squint at the room. Nobody.
I roll the other direction and sit up to peer at the bathroom. Lights off, door wide open. Not there either.
I reach out to turn off the alarm clock. Then I stifle a yawn and sit up. But there are just my toys neatly stacked beside the bed, all of them squeaky clean. None of Caleb’s clothes are here anymore—not the boxers or shirt he left strewn around the place.
“Caleb?” I call, hesitant, knowing it’s a long shot.
The dead silence of my house answers the question. He’s gone.
I collapse back onto the pillows with a deep sigh. It’s fine, I tell myself. This is what I’m paying for, after all. I hired him to have a little fun. To get the release I was craving—the one I needed after two years without a partner in my bed. That’s all.
So why do I feel emptier now than I did before I was filled?
I get to the bakery on time today. Lara comes in later on Saturdays, so I open the storefront myself and set up the front of house while I wait on Jen to come in. She and Carl trade off on Saturdays. Normally it should be a lighter load today, but after the delays yesterday, we’ll still need to work our asses off to catch up.
I’m not looking forward to it.
Lara keeps insisting we should hire a third assistant, or that I should let her help out in the kitchen. Or at least let Jen or Carl take over lead chef position once a week, as practice.
“They’re good kids,” Lara keeps saying. “If you give them enough instruction, they can handle taking care of things for a day or two a week. To give you some time to recharge.”
I know, deep down, that she’s right—I’ll have to let them take on more responsibility sooner or later. Lara can supervise them when I’m gone—and hell, at this point, Jen and Carl have been with us for so long that they could probably handle running the whole store on their own for a while if need be.
But it’s so hard to trust anyone else with my baby. I built this company from scratch. It’s doing so well right now. But I’m all too aware of how fast successes like this can collapse in the food world. One wrong step, one terrible review, one vengeful customer with too much influence, and your whole empire can come crashing down around you.
I refuse to let that happen to my baby. Which means I refuse to leave my baby in anyone else’s hands, even for a single day.
Today, however, I’m distracted from said baby for once. It takes me three tries to count the register right, and I give up on balancing the account book entirely this morning. I’ll handle it in the afternoon, hopefully once my dose of caffeine kicks in, or once Lara shows up to smack my forehead and snap me back to reality.
In the meantime, I can�
��t stop daydreaming.
Reminiscing, really.
Did last night really happen? It feels like a dream now, a distant fantasy that couldn’t possibly have been real. No way did I find a guy that hot, a guy who was into the same kinks as me, and willing to get so down and dirty with me in the bedroom. No, more than willing—excited to.
That’s why they call them escorts, I remind myself. He’s paid to do that. To make me feel totally relaxed and at ease with myself. To make it seem like he’s feeling just as much as I am about our hot, wild night together.
My belly tenses. I bet he’s off planning another wild night like that with some other client. I’m probably just one in a million women with freakish kinks who he’s banged.
But something about it felt different. Felt like more than just a monetary exchange, a paid hookup.
Unbidden, I find myself opening my phone and flipping through to the website. To ogling the photos on his profile again.
Fucking hell, he looks even hotter in person than he does on this site.
Still, he doesn’t look too shabby on here.
I’m ogling one of his shirtless photos when Jen arrives and startles me into pocketing my phone.
“You okay?” she asks, eying me strangely.
“Of course!” I answer, my voice too high-pitched, my smile too wide. Really subtle.
Luckily Jen has never been the curious type. We work side-by-side in the back for most of the morning. Then, at lunch break, I’m back to the same site, scrolling through the pictures again.
My pussy tightens at the memory of the way his thick cock felt inside me. And his filthy mouth, goddamn. Or the way his cock tasted when he deep-throated me, my back pinned against the wall by that dildo…