My Boyfriend’s Dad

In a recent email exchange with my lover, I remembered a fantasy I had about my high school boyfriend’s dad, Mike. I started to write it all out in our emails, and before long I was masturbating to it, confessing all kinds of dirty things. Although the story below is fictional, the fantasy was very real to me when I was 18 years old. There were so many moments on Mike’s back porch when I used to wish for this to happen. I’ve included a few sentences of my email exchange, and then the fantasy below. I hope you enjoy it as much as I did!


I’ve had another orgasm imagining all of this and I felt sort of guilty about it, so I thought I’d unburden myself here. Something tells me you won’t judge me too harshly. I feel like such a bad girl…



You are a bad girl, and you have me smiling big.




I am… a very bad girl… I can hear him saying that to me in my ear, in that deep husky voice.

I’m wearing Jeff’s white button down shirt, a little drunk from being out earlier that night. The top few buttons are undone so that you can see the round fullness of my tits and the depth of my cleavage every time I lean down. The bottom of the shirt hangs to the middle of my thighs, just barely covering my ass as long as I don’t bend over. And I have my panties on too, always the same black cotton string bikini ones I wore in high school. No pants, bare feet, my long brown hair in a tousled ponytail, a little damp at the nape of my neck from sweat. Of course, I’ve just been fucked. Jeff’s still in bed watching the movie we’d popped into the VCR. I always do this, come down for a cigarette after we fuck, and if there’s a bottle of wine open in the kitchen, I pour myself a glass. Jeff has the coolest parents. They never seem to care about that kind of stuff.

As I file down the last few stairs that lead into the living room, I glance at the sliding glass door to the back porch. Mike’s sitting there at the patio table with his back to me, cigarette in hand, glass of red wine on the table. I can’t help but smile when I notice that Katherine is nowhere to be found. I love when it’s just him and me. I pour myself a generous glass of wine before slipping out back, startling Mike a bit, but he smiles when he sees that it’s just me. “Mind if I join you?” I ask a bit breathlessly, already pulling out the seat next to him and making myself at home.

“Of course not, Joanna,” he smiles and slides his pack of Marlboros across the table towards me, his eyes darting up and down my body almost too quickly for me to notice. Almost.

“Thanks,” I chime a little too cheerfully, pulling a cigarette from the box. I look around for a lighter but he has it in his hand already, flicking it for me. I lean in towards him, inhaling deeply, trying to keep my eyes on his. I think of all those old movies where the sexy, confident man lights a woman’s cigarette and they hold gazes just like I’m doing with Mike right now.

“So,” I exhale and tap my cigarette onto the rim of the ashtray. “What were you thinking about all by yourself out here?” Mike smiles in his sexy way and I feel my pussy swelling a bit, moistening again in my panties.

“Oh nothing interesting… just work stuff,” he replies, blowing a thin stream of smoke out into the night. I can’t help but smile, admiring how the smoke curls from his lips like a whisper. “How about you,” he grins. “Are you having a good night?”

I try not to smile too obviously. Mike knows what we do in Jeff’s room before I come downstairs for this smoke. In fact, sometimes he’s in his bedroom next door to us while we’re doing it. Sometimes I wonder if he can hear, and what he can hear. Can he decipher my little whimpers, my moans when Jeff fucks me deep and rough? Does he hear the sound of Jeff spanking my ass, telling me what a bad little slut I am, while he fingers my hot pussy? Does he ever wonder what it would feel like, my little teenage cunt wrapped around his cock, this man old enough to be my father who I flirt with at every opportunity?

“Oh, I always have a good night when I come over to your house,” I say with a smile, unable to look him directly in the eyes as I think of all the things his son has done to me tonight. I take a sip from my wine and stretch my legs under the table, flinching slightly when I feel Mike’s leg brush against my bare thigh. I look up at him and bite my lower lip. I know he felt it too.

“Well,” his voice shakes a little but his gaze is steady, first locked on my eyes and then traveling lower, to my mouth, watching me wrap my full lips around the cigarette and suck on it slowly, “it always sounds like the two of you are having fun.” He laughs a little nervously. “Not that I eavesdrop or anything…”

“Of course you don’t.” I look up at him and smile, stretching again but this time letting my leg sweep along his more slowly, more deliberately, my bare foot resting along his ankle. He looks at me curiously but says nothing. “I’m sure it wouldn’t be that interesting to you anyway,” I giggle.

“Oh I wouldn’t say that, Joanna,” he replies, his voice lowering a bit, the expression on his face a little more severe than usual. “Sometimes I’m very surprised by what I hear.” I can feel the blush spread across my cheeks as he says this, like I’ve been found out, like I’m getting in trouble. I open my mouth to say something to lighten the mood but nothing comes out. I can’t even look at him.

When I bring my cigarette to my lips we both realize that my hand is shaking, the cigarette quivering in the air. I hear him chuckle softly and I finally bring myself look at him. His eyes are fixed on my trembling hand. “Nervous?” he asks, with an amused smile.

“I…” my voice trails, growing hoarse all of a sudden. I smile shyly, a bit embarrassed at how young I must seem… or, maybe embarrassed at how young I am. “I guess so,” I manage to say. God, he must think I’m such a baby! In my fantasies I’m never like this, so young and bashful, ashamed of myself even. I feel his hand resting warmly on the top of my knee, squeezing lightly. I gasp a bit and look up at him hopefully. He smiles.

“Do I make you nervous?”

I nod slowly, looking down but finding the courage to slip my hand on top of his where it rests on my knee. I want to keep him there, and I want so much more, if I could only tell him…

He slides our hands just a little bit higher up my leg, to my thigh. My heart starts to pound in my ears, and I can feel it in my pussy. It’s like my pussy is on fire, overheating, his hand so close… He’s leaning in now, so close to me, whispering in my ear, “Tell me, Joanna… Why do I make you nervous?”

He pulls back to look at me as I struggle for the words to tell him. I take a deep breath. “Because… you make me feel things…” my voice is shaking. “…that I’m not supposed to feel.” My cigarette rolls out of my fingers into the ashtray, like I’m too weak to hold onto it anymore. My other hand is stroking the back of his now as it moves higher, and I guide him to the edge of my panties and then further, his fingertips grazing the wet spot at my pussy. My eyes meet his and I press his fingers against the wet cotton. “Do you feel that?” I ask softly, like it’s a secret.

He nods, and strokes my cunt through the panties, leaning in close to me so he can stroke me harder. I moan softly. “You make me feel like such a bad girl…”

“You’re a very bad girl, Joanna,” he tells me sternly in my ear. I feel his mustache tickling me there, and his breath, so warm. I move my fingers over his and help him rub my hot pussy through the panties, almost like I’m using his hand to masturbate…

I feel his teeth on my ear, now his tongue, and I groan. I can’t even control myself anymore, so greedy for him. I slip out of my chair and down to my knees on the floor, kneeling in between his legs.

“I am,” I whisper in his ear. I kiss his earlobe softly, and then I nip at it with my teeth. He rubs my pussy harder through the panties and I moan into his ear, unable to resist one more dirty whispered plea. “Please, Mike… punish me…”

I move in to kiss him and he grips my shoulders tightly, holding me in place so I can’t inch closer to him. The look in his eyes– what is that? Anger? Lust? Disgust? God, please let it not be that…

“You want to be punished, little girl?” his voice is steely but quiet. My heart is pounding, like when I was little and getting in trouble, but also from excitement, my nipples tightening against Jeff’s shirt, my pussy overheating, moisture soaking the center of my panties. I weakly nod my head and he grabs my hair by my ponytail, pulling my face into the crotch of his pants. I feel his hard cock straining through the fabric, pressing into my cheek, my mouth, my chin.

“Unzip my pants and suck my dick, little whore… If you take me all the way into your mouth, maybe I’ll reward you with a nice hard spanking…”

I can’t help but whimper when he says that… I know he’s heard us now, heard his son’s hard slaps against the tight flesh of my ass while I rub my wet pussy against his leg, bent over his lap like a naughty little girl. Does he know that I picture him when Jeff spanks me? Does he know I want to be his bad little teenage whore, his cheap fucktoy? I want him to know…. I want him to know everything, to do everything to me….

My fingers are trembling but I manage to unzip him, to pull his pants to his ankles, to take his hard cock out of his boxers. Oh god it’s perfect, long and thick and so hard. I love how it feels in my hand, so hard and swollen… I kiss it slowly, indulging in the smoothness of his head, the taste of his precum as it leaks onto my lips. I look up at him hungrily and start to wet his cock with my mouth, licking the shaft, admiring how it shines, kissing it almost lovingly, worshipfully, desperately. I want to be good for him… a good little girl…

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I wrap my lips around the tip of his cock, slowly sliding my mouth over him inch by inch. I want it to feel like he’s prying my mouth open with his dick, like he’s fucking a tight virgin pussy. He groans as my lips glide over more and more of his length. I angle my mouth so I can keep going, so I can take him deep into my throat, and when I do, I hold his cock there, all the way inside me, my throat fluttering around the tip. I look up at him for approval and he smiles, his eyes full of lust and his hands on the back of my head, pulling me deeper so my nose presses against his abdomen. My eyes well up and I start to gag… but it feels so good. Can he feel how hot this makes me? I want to take more… I want him to stuff that cock in me, to rape my little mouth…

He finally releases his hold on me and I’m coughing, gasping for air, wiping the tears from my eyes. He swats at my lips with his cock, so hard now and slick from my mouth. “More, Mike…” I plead with him, opening my mouth to catch his cock as he slaps it against my lips. “Please…”

“What a filthy little whore you are, Joanna,” he smirks at me. “Is your pussy wet?”

I open my mouth to answer but then I stop myself and instead I slip my hand into the waistband of my panties, drawing the opening of my slit with my fingertips. I gasp when I feel how creamy my pussy has gotten, still sore from being fucked by Jeff, but unmistakably swollen and leaking with desire now… I bring my wet fingers to Mike’s face, running them around his lips again and again before he catches them in his mouth and sucks on them greedily.

“Mmmm,” he moans as he licks and sucks my creamy little fingers. “Such a sweet young cunt…” He brings me up to my feet and then gets down on his knees, his face only inches from my mound. I close my eyes and a moment later, I feel his breath on me through the cotton, then his nose pressed against my slit, inhaling… Fuck, that feels so good, his breath so warm on my panties, his nose pressing against my clit. I whimper and grind against his face impatiently until he finally pulls my panties down to my ankles and brings his mouth to my naked cunt.

“Ohhh god… yesss…” My fingers slide through his thick gray hair, pulling him deeper into me. His mouth is ravaging my pussy, his mustache rubbing against my smooth mound. I spread my legs wider for him and his hands trail back to my ass. He squeezes me there so hard that I gasp out loud. He looks up and smiles at my reaction. “Dirty little whore.”

Suddenly I feel the sting of his palm on my ass, first one cheek and then another, harder than Jeff has ever done it, punishing and cruel. His mouth is still locked onto my pussy but his palms crack against the flesh of my ass so hard that I can’t help but cry out. Squeezing my red ass cheeks, he wraps his lips around my clit and sucks insistently, shoving two fingers deep in my pussy and rubbing my g-spot while he works me off with his mouth.

“Oooohhh fuck… I’m so close Mike… ohhhh….” My knees buckle and I fall forward a bit, overcome with my orgasm as it shoots through my whole body, leaking into his mouth and all over his hand. My body aches with it until finally the last wave rushes over me.

He rises to his feet and unbuttons my shirt, kicking off his own pants, stripping down so I can admire his naked body for the first time. I run my fingers along his chest, smiling at the gray hairs I find there. God he’s so fucking sexy… How can I want him this badly even when he’s right here in front of me?

I bury my face in his chest and kiss him there, my tongue trailing along his skin, biting gently, moving to his sexy shoulders, his neck, making love to every inch of flesh he gives me access to. My lips find his and we kiss deeply. I can taste my cunt on his mouth and I can’t help but moan. We grind into each other, his hard cock pressing into my bare mound. Oh how I want it inside me. I want him to spear into me right now… As if he’s reading my mind he asks, “Where do you want my cock, slut?”

“In my pussy, please, Mike…”

He spins me around and bends me over the table so my tits are pressed against the cool glass and my firm ass is arched out towards his cock. He rubs the tip slowly up and down my slit. “Do you like how that feels, whore?”

“Oh fuck yes… I love it… I love your cock, Mike…” I arch as far back as I can, daring him to violate my little teenage pussy with that big hard dick. It’s agony, waiting like this. But he keeps torturing me.

“Mmm I want you to tell me something, Joanna,” he says slowly, still dragging the tip of his cock up and down my slit, coating it in my juices. “Do you ever think about fucking me? I mean, before tonight… had you ever… imagined it?”

I turn to look at him over my shoulder and his eyes seem to bore into mine. My whole body flushes with fear, excitement, guilt. “I…” my voice trails and I try to take a deep breath and begin again. “I have… Sometimes I try to pretend it’s… innocent… like, a little schoolgirl crush…”

“Innocent?” He laughs, and then he spanks my ass hard. “No, I don’t think it’s that…” I moan helplessly when his palm cracks down on my ass, and he’s relentless this time, he’s not fucking around.

SLAP! “Do you think of me when you’re fucking Jeff?”

My eyes are pleading now as I look back at him. “Mike… don’t make me answer that…”

He pushes the tip of his cock into my pussy from behind and starts fucking me with just the tip, just an inch, and I start to groan. He slaps my ass again. “Do you want more cock, Joanna?” I whimper, and nod. “Then tell me, you dirty little whore. Tell me… Do you think of me when my son bends you over his knee? Do you wish it were me?”

“Ohhh god… Yes… I think about you, Mike… I wish it were you, punishing me just like right now… I wish you were filling me with your cock!” My eyes well up, and I can feel my cheeks turn red with shame. I’m so desperate for this fuck, I’ll say anything, but he knows it’s true. I can hardly look at him, but I feel my cunt leaking obscenely down my thighs…

SLAP! “Oh you dirty fucking bitch!” I groan as he spanks me harder than ever, my ass turning bright red. “Beg me for my cock, little whore. Beg me to fuck your hot little teenage cunt!”

“Yes please!! Please Mike…. Fuck me… I’m begging you, bury that cock all the way inside me… oh please!!!”

He slams his whole cock deep into my pussy and I cry out… “Ohhhhh!!” Mike’s cock is bigger than Jeff’s… he fills me so completely… I groan when I realize that I had his son’s cock in me less than an hour before. I feel like such a cheap little slut… and it only makes me hotter for Mike. Holding my hips firmly, he slides his cock out of me only to roughly shove it back in, my body jerking forward with every thrust. He pulls on my ponytail hard and pounds me harder, harder than I’ve ever been fucked. “More, god, more please… oohhh fuck, I’m so close!!!” He rapes my pussy again and again until my feet are dangling off the ground, my whole body spread out on the table.

“Ohh that pussy’s so fucking tight… cum for me you slut… Cum all over my cock!”

I cry out again and my cunt starts to squeeze against his hard dick, juicing all over him, leaking onto his balls… I’m moaning, completely swept up in orgasm, but he keeps pounding at my poor little pussy, relentless, until I beg him to slow down.

It takes me a few moments to gather myself, to feel my feet touching the ground again. He slides his cock out of my pussy and I stand up, turning to face him. My legs are still trembling from my orgasm and I reach for his shoulders, pulling him close to me, and kiss him hard. His mouth feels amazing against mine, and I’m so greedy for more of him, sucking on his tongue, trying to take him into me, to keep him inside. He lifts me off the ground and sits me on the edge of the table, breaking our kiss and looking deeply into my eyes. His hand travels down my naked body, between my tits, down my flat stomach, his fingers tracing the outline of my swollen pussy lips but then moving lower, further back. I gasp when I feel his finger rubbing gently against my asshole, and he smiles at the look of panic on my face. “Jeff hasn’t fucked you there yet?”

I shake my head slowly, unable to speak, my heart starting to pound. I’ve never even thought of being touched there, let alone being fucked there. And yet, I find myself grinding against the flats of his fingers as they rub up against my asshole, spreading the juices from my pussy to that very private place. He leans in close to my ear and whispers, “I haven’t cum yet, Joanna. Do you know what I’m saving it for?”

I shake my head nervously, but of course I know. God, can he feel my heart pounding in my chest? My whole body is tightening up against him, like the panic has spread everywhere. Because I don’t know how to say no to him, but I can’t imagine saying yes…

“I want to fuck you where nobody else has,” he says evenly, his lips moving against my ear. “Not even Jeff.” My eyes are welling up and I feel a tear trickle down my cheek and drip onto his shoulder as he talks. Can he feel that too? Does he have any idea how scared I am? I want him to know… “Now, are you going to be a good little slut and take my cock there?” he moves back to look at me, brushing a tear off my cheek with the back of his hand. I nod my head silently and he smiles, kissing my ear slowly, his breath warming me. “Good girl.”

His mouth travels down my body gently, so gentle now, like he’s a different person almost, his tongue flicking against my hard nipple, his mustache tickling my navel. He plants soft kisses along my slit, licking, making me wet again. I lay back on the table and he pushes my legs up against my chest, exposing my virgin ass to his gaze. I feel his tongue trailing back so slowly, like he’ll never get there, but he does, and soon I’m moaning softly while his tongue sweeps across my ass, wetting me, exploring me. Without meaning to, I find myself pulling my legs further back, giving him more to taste, silently giving him permission to penetrate me with his tongue. “Ohhhh…” I moan when he finally opens me, first with his tongue and then with his finger soaked in my pussy juice. “More… Mike….”

He stands up and pulls me to the very edge of the table. I’m still bent back all the way, my pussy and ass open to him, waiting to be violated. My eyes are on his, and I see for the first time the look of pure lust in his face as he rubs his cock along my slit and then further back, pressing against my virgin ass. Gently, he starts pushing the head inside me and I whimper, my breath catching in my throat when I cry out in pain. I feel so stretched, such an invasion, so wrong… I’m shaking my head, trying to take deep breaths, anything to accommodate this thick cock filling my most private place.

He groans. “Ohhh god you’re so fucking tight, Joanna… Mmmmm….” I feel him sliding inside me slowly, every inch of his length filling me, like he’ll never stop… I bite down onto his shoulder when he tells me that he’s buried all the way inside me now, his cock in my ass, he’s saying it over and over again, holding himself inside me until I start to relax a bit. He takes my hand from behind his neck and moves it down to my pussy. “Play with yourself, Joanna…”

I slip my fingers between my pussy lips and gasp when I realize how wet I am. He smiles. “You like that, little girl?” Starting to move his cock inside me now, in and out, slowly. I can feel myself stretching to fit him, to take him into me, almost like he was meant to fuck me in this forbidden little hole. “Ohhh, god…” my fingers working faster now, something changing inside me, something unraveling, like I want… “more… Mike… More, please… I can take… harder….”

He groans and sinks his cock all the way inside me, then starts to fuck me in earnest, pumping me full of his length, pounding into my tight virgin ass, and I’m moaning, we both are now, every profanity we’ve ever known. My pussy is so wet I can hardly find my clit through all the cream but I do and I rub myself so hard, as hard as I’ve ever done it before, edging towards an orgasm unlike any I’ve ever known. His hand is on my throat now and he’s holding me down flat against the table while he pounds me, and fuck it feels so good, his fingers wrapped around my neck, his cock buried in my little ass, my clit swelling, my pussy dripping, so close now, I hear him groan and I do too, both of us unleashing on each other. My whole body is throbbing, clenching, milking the hot cum from his balls and feeling it fill my ass, shooting so deep inside me, someplace I didn’t even know existed until now.

Seconds pass, but it feels like longer. He’s laying on top of me, panting, until his cock finally softens and slips out of my ass. I sigh when I feel him slide out of me, an emptiness I never felt before. He falls back into his chair and pulls me with him, peeling me off the table and drawing me into his lap. I wrap my legs around his waist, kissing him softly. “Mmm, I can feel that cum leaking into my lap, dirty girl,” he says. I grin and untangle myself from his embrace, dropping to my knees again on the floor. I know what he wants… I don’t even have to ask. Slowly I lick the cum from his thighs, my eyes wandering from his lap to his face, meeting his gaze. He guides my face to his cock and I open my mouth, licking him there too, eating every drop of cum as he runs his fingers through my soft hair. “That’s it, little slut… Clean my cock with your mouth…”

We reassemble ourselves after a few minutes, and I look back at the sliding glass door, debating if I should go upstairs and join Jeff in bed. Mike notices the look on my face and smiles gently, offering me a seat beside him at the patio table. He opens his pack of Marlboros and offers me one. “Don’t you normally do this… afterwards?”