Cassidy
He takes a deep breath like he’s about to say something. Then he changes his mind. “Good night, Cassidy.”
Shit. Is that how I want this to go? “Wait.” He pauses, but doesn’t turn. I take a deep breath. Using a voice that’s not quite mine and more or less jacked from a porno, I say, “You don’t have to go, Mr. Webster. I thought you might like something else sweet. For your birthday.”
He turns, eyebrows up. “That depends on what you’re offering me, I guess.”
I want to say something sexy. My tongue ties itself in a knot, though. Instead, I shoot for honesty. “I don’t know how to do this. I’m not experienced. I’m afraid I’m doing this all wrong.”
“Do you want me to help you right now?” He reaches his hand up and lightly, so lightly, traces my jaw with one finger.
“Yes,” I whisper.
He tugs on my ponytail. “Tonight, Cassidy. I’ll be Mr. Webster and you can be my shy, inexperienced babysitter. Would you like that?” He smiles. “I can see your pulse racing like crazy. I think you do like that. You can just relax, sweetness. Just submit to me. Can you do that? Can you trust me tonight to take you where you want to go?”
I hear a sound and realize it’s me. Whimpering. “I think so.”
“That’s not good enough. Do you want to be my naughty babysitter tonight, yes or no?”
My pussy floods with moisture. I think it makes me a pervert, too, maybe. But I don’t care. I want to play this game.
“Yes, Mr. Webster. I want to be your naughty babysitter tonight.”
He swallows hard. “You change your mind, you tell me what your safe word is. Because as of right now, it isn’t no and it isn’t stop. In fact, no is just going to make me go at you harder. So, tell me a word that will halt the scene.”
I didn’t realize there was going to be a thinking portion of the game. “Um...”
“You’re a smart girl. Tell me a safe word.”
“Diaper,” I blurt out. I should just retire now. I suck at being sexy.
He shakes his head, trying to hide his smile. “All right. That’s the only thing that will stop me now. Do you understand? For the next few hours, you’re not my partner. You’re my shy teenage dream. And I’m not Conner. I’m the man you don’t get to say no to. I’m the man who will take you where you’ve never been before. I’m going to make you so, so dirty. Got it, baby? You’re not my friend tonight. You’re not the woman who runs my house. You’re going to learn what naughty is. You’re my toy. You still on board? Do you think you can handle playing this role?”
I nod but I can’t breathe. This is what I want. I want to give myself to him. Live the fantasy.
I don’t know what to expect. Well, except I do. I’ve been watching a lot more porn this week. And all of it has been babysitter smut. I’m so turned on right now.
I’ve been reading some stories, too. I think Conner reads the same ones, maybe. Either that or he reached right into my head and pulled out my darkest desires. To be submissive to a dominating man. To let go. I’m not talking BDSM with props, but the idea of him controlling me makes me flush everywhere.
And I want to please him. I want to do this right. He’s making it easy for me—all I have to do is play the shy, inexperienced teenaged babysitter. Which shouldn’t be a character stretch.
“You’ve been a really good babysitter, Cassidy.”
“Thank you, Mr. Webster.”
He gets behind me, his hand on my hip and the rest of him brushing against my back.
I stiffen and try to scoot away, like my character would, but he pushes against me harder.
“Don’t,” I say. “It’s not appropriate for you to touch me, Mr. Webster. I’m your babysitter.” I don’t know how I’m falling into this role-playing so easily but it’s like a huge weight lifts off me. I’m not me, right now. It’s letting go and becoming at the same time.
He squeezes me even harder, leaning in to speak in my ear so I feel his words as much as hear them. “Don’t what, sweetness? Give my best babysitter a hug? I’m so grateful for the way you take care of things.”
“You’ve been drinking, Mr. Webster.”
He moves us a couple steps so I’m in front of the sink. “I like a beer or two at night. It helps relax me. What do you do to relax, sweetness?”
“You shouldn’t be touching me.” He’s still squeezing me. I start to feel trapped. Mr. Webster is strong. Really strong. I’m falling into the game, and all my senses are leading me further in. I start to forget I’m playing. “I should be going since you’re home now.” He nuzzles my neck. I try to wrench away, but Mr. Webster holds me firm. “I have to go,” I say.
“Do you like working here?”
“Yes.”
“That’s good. I’m glad. I want you to keep working for me, but I’m worried.”
“Worried?”
“How do I know you’re a good influence on the kids? How do I know you’re a good girl?”
I feel like the script of a bad movie is on the teleprompter of my brain. “I am, Mr. Webster. I’m a very good girl.”
“I don’t know if I can believe you. You’re going to have to convince me you’re a good girl.”
“What do you mean?”
“You need to prove to me you’re a good influence, Cassidy. That you won’t do something that would reflect badly on me as your employer. That I can trust you with my kids.”
I think about what I could possibly say to convince him.
He takes a step back, and I sigh with relief. The adrenaline is coursing through me hard. “Tell me what you do when on your off time. What do you do with your friends?”
Ugh...what do normal girls do? It seems like it’s been a really long time. “We watch movies and hang out.”
“Are there boys there?”
I shrug. “Sometimes.”
“Do you kiss the boys?”
My skin heats suddenly. “Mr. Webster, I don’t want to talk about boys with you.”
“That means yes.”
“Yes, I’ve kissed boys before, but it’s no big deal.”
“Show me how you kiss the boys, then.”
“What?” He can’t mean it.
“Like this?” He pushes his mouth against mine. His lips are gentle, and he is kissing me almost sweetly. “Like that? Is that how you kiss them?”
I nod.
“That’s not so bad.”
I nod my head, agreeing with him. “You shouldn’t be touching me like this, Mr. Webster. It’s wrong.”
“I’m just getting information. I have to know you’re safe to have around my kids. That wasn’t so bad, but do those boys ever do this?”
He pulls me to him again. This time, his clever tongue licks my lips until I open, allowing him in. His kiss is slow, his tongue tangling with mine languidly until all my muscles loosen. He tilts his head, deepening the kiss. He tastes like chocolate and coconut. All I am is sensation, the slow glide of his tongue, the rasp of stubble on his chin, the smells and tastes of him. My mind loosens more than my muscles, and I can’t hold a thought. I’ve never been kissed into a hazy mind before, and he groans into my mouth.
He pulls back and goes for my throat. “Do you let them do that? Do you let the boys put their tongues in your mouth when you kiss them?” he asks against my skin.
“Sometimes,” I whisper. Nothing like that. Never anything like that.
“Do they touch you here?” His hand gropes me, squeezing and kneading my breast.
I gasp loudly, surprised by the sudden change.
“Do they?”
My porno script opens back up. “My ex-boyfriend did, Mr. Webster. But we were going out for a long time before he tried.”
“Over your bra or under, like this?” He snakes his hand under my T-shirt and into my bra, tweaking my nipple.
I know I shouldn’t like it, know it is wrong. I can’t believe I asked for this and I like it. My adrenaline is high, and I’m trembling.
“Under, but just once in a while. I swear.”
“I’m not sure I believe you. Show me your tits, sweetness. I need to see something for certain.”
He steps away, giving me room.
“Mr. Webster, I don’t think...”
“Take off your shirt, Cassidy. Don’t make me tell you again.”
My breath catches in my throat. I should be scared. And I am. Kind of. Mostly, I am totally hot. I pull off my T-shirt, keeping my eyes on the floor. I don’t need to look at my chest to know my nipples are pebbled like hard little stones in my bra.
“You’re not done.”
How far is this going to go? Are we really doing this? I shiver, remembering that veiny monster he keeps in his pants. I reach behind me and unclasp the bra, sliding the straps down and letting it fall to the floor.
“Those are real pretty, sweetness.”
“Thank you,” I whisper, not sure what to say while my boss stares at my breasts like they are a meal set before a starving man.
“Hold them up for me, baby. I want a really good look.”
“I can’t...” I’m so embarrassed.
“You want to keep this job, don’t you?”
I nod.
“Tits. Now.”
He’s really good at this. He promised me a pervert and he’s delivering.
I slide my hands beneath my breasts and cup them from below as if I were offering them to this older man I work for.
“Those are nice. Really nice.” He leans down and licks one rock-hard nipple, causing a shockwave to course through my body straight to my pussy. Oh God. “You taste delicious. Anyone ever tell you that before?”
I shake my head.
He keeps his face by my tits, but looks up at me. “Are you saying no boy has ever licked your raspberry nips before?”
I shake my head again.
“I don’t think I believe you. No boy has ever done this?” He licks the other one and then alternates between the two a few times.
I am going to pass out. I can’t remember what is fact and what is fiction. I like it when he talks roughly, when he treats me like an object. What does that say about me?
But he likes it, too. And we’re adults. Lonely adults with too many responsibilities. We’re not hurting anyone. We’re just getting off.
“Mr. Webster, we’re being so bad.”
He puts his hands on my hips and sucks my left nipple all the way into his mouth, and I groan out loud with pleasure.
He steps back, and the cool air hits the warm saliva he left behind on my boob. “Just because nobody has sucked them before doesn’t make you innocent.” He reaches for my hand and sets it on his groin. “You ever touch your boyfriends here?”
“No,” I whisper, my voice gone who knows where. He forces my hand to rub him through his sweats. He is so hard and big. I clear my throat. “We shouldn’t be doing this. It’s wrong.”
He’s watching my face very carefully. Since I’m not pulling my hand back, he knows I’m still playing along.
“Don’t you want to see what you’ve been missing, sweetness?” He takes my hand and shoves it down his pants. His pubic hair crinkles around my hand, and he strokes my fingers down his shaft. It feels different than I thought it would. Like steel encased in velvet.
Desire spears through me. I feel so naughty.
He tips his head back as if in ecstasy. “You know how long I’ve been waiting for this?”
“Mr. Webster, please let me go. You don’t want to make me do this.”
“Baby, you have been begging to do this for months. You think I don’t notice you checking out my cock? Did you like watching me the other night?”
I blush even hotter. Now he’s bringing reality back in. This weird mix of the real Cassidy and the naughty babysitter Cassidy are turning into one.
He pulls my hand out and circles both my wrists in one powerful grip. He backs me away from the sink and against the wall. He raises my arms above my head so my tits lift, pinning my hands to the wallpaper. I groan as he plunges his other hand beneath the waistband of my shorts and into my panties.
He traces one finger down my slit, and I shudder, looking into his eyes as he grins like the devil. “You’re soaking wet. All for me, sweetness.” He thrums his thumb against my clit, and I bow my back, arching my pussy to him. “Your boyfriends ever touch you here?”
He pushes my button again, and I gasp. “No. Just you. You’re the only one.”
“That’s a good girl. You waited so Mr. Webster could show you what you really want. What you really need. Isn’t that right?” He pushes a finger into me and presses my clit with his thumb.
“Oh God,” I cry.
“Jesus, baby, you’re going to fucking come in my hand.”
He keeps diddling me, and I become desperate. He is going to make me come. I should stop him, at least pretend to, but what he is doing feels so fucking good. I hit my head on the wall trying to knock some sense back in, but then he lowers his head and starts sucking on my tits again, and I know I am going to lose.
“Please, Mr. Webster. Stop this. Please.”
“You’re so fucking wet right now that it’s running down your leg.” He slows down but doesn’t take his hand away. I don’t think my legs will hold out much longer. “Those boys you kissed weren’t man enough to let your inner woman out, but I am, sweetness. I’m all man. What you need. An older man. A very bad daddy.”
He pulls his hand out of my pussy, and I almost cry with disappointment. He wipes his fingers on my nipple and then sucks the juices off. The sensation makes me clench my legs together. “You taste like honey.”
He lets go of my wrists and steps back.
I am free, but I don’t know what to do.
While I am trying to decide my next move, he reaches for the hem of his tank top and pulls it over his head. Oh God. He’s perfect like a statue. Like the cover of every romance book I’ve ever read. I want to touch him. That tattoo mesmerizes me. I want all of him pressed against me. He raises his eyebrows like he can read my thoughts as he pushes down his sweats.
I need to get back on script. “What...what are you doing, Mr. Webster?” I ask, even as he kicks the last of his clothing off.
And there it is.
The beast that lives in his pants. It is stiff as a flagpole and pointing just as proudly. I can’t tear my eyes from it.
His hand goes to his cock, and he pumps it slowly.
“Right here? You’re going to do that right here?” I am trapped between him and the wall.
And I can’t tear my eyes off his dick.
“Did you like the way my dick felt in your hand, Cassidy? I know you did. I like the way you feel too, all slick and moist and hot.” His eyes are hooded, and he focuses on my tits. “And the way your pussy tastes. Damn. I just got a small sample, and I’ll never forget how sweet you were.”
I can’t get a deep breath. His words are hypnotizing me to the movements of his hand on his cock. It has to be eight or nine inches. But it is the girth that really amazes me.
He isn’t pounding it fast. He takes his time, stroking up and down slowly, his eyes on my tits. I clench my pussy tightly to keep from humping the air. I want to dip my fingers in and come so badly.
He picks up my hand, and I don’t pull it back when he brings it to his stiff cock. He folds my fingers around him as far as they will go, and moves my fist up and down in the same rhythm he was using before.
“There, that’s not so bad, is it? You’re doing so good, baby. That feels great.”
He loosens his grip, but I don’t let go. My hand slips a little on the pre-cum oozing out, and it helps me to slide my hand faster. “Like this, Mr. Webster?”
“Mmmm,” he says, reaching his hands to my tits again.
He strokes them softly, and I add my other hand to his cock. His strokes become harder until he is pinching my nipples just like I do to myself sometimes. I cry out as a tiny orgasm rips through me, stunning me. I didn’t know I could come without touching my pussy.
He chuckles and loosens me off his cock. “That’s what I thought.”
Before I know what is happening, he grasps my waist and picks me up as if I weigh only a few ounces. He plops me onto the counter and spreads my legs wide, pushes the crotch of my shorts to the side, and dives his tongue into my slit.
Up and down, in and out. He uses his whole face in my pussy, making noises like some kind of animal. Tonguing me, nipping me. I have to rest the backs of my knees on his shoulders and hold on to his hair as he goes crazy on my clit. The pressure inside me is building higher and higher as I squirm against his face. I can’t stop my body from arching and trembling.
“Come on my face, Cassidy,” he says into my pussy. “Get it all over me.”
I have no choice but to obey. The biggest orgasm I’ve ever had rips through me, ricocheting off every nerve. He is down there slurping me, moaning about how good I taste, and still I can’t stop humping his mouth.
I am a shaky mess when he finally lifts his head. Mr. Webster grabs the back of my head and pulls me into a kiss I shouldn’t want. I try to back away.
“Taste how good you are,” he says and thrusts his tongue into my mouth again, forcing my own musky sweetness into my mouth.
Incredibly, it turns me on more, the taste of me on his tongue, and I suck on him, unable to stop myself.
He rips my shorts down and wraps my legs around his waist, pulling me easily off the countertop. His turgid dick grazes my bottom and makes me squirm as he carries me. “Which bed should I fuck you in, sweetness?”
Oh God. My breasts rub against his chest. “No, Mr. Webster...We can’t—” but the motion of his cock under me as he takes us upstairs is getting me hot again, distracting me.
He lays me on the bed, his, and goes back to eating out my pussy.
I come again, hard. I’m wrung out and shaking.
That’s when he says, “Diaper.”