My name is Jessi Fellatio, and no, that’s not a typo or a crass pseudonym I picked up in a desperate attempt to sound edgy. It’s my actual, legal, given name, a peculiar burden I’ve had to bear since I first set foot in this world nineteen years ago. It’s a name that’s turned more than a few heads and elicited a smattering of snickers in class, a name that’s caused me to reconsider my life choices and question the sanity of my parents. But here’s the kicker: it’s also the name that’s currently funding my college education.
You see, I’ve got a sugar daddy, a man named Richard, who’s old enough to be my grandfather. He’s a successful entrepreneur with a penchant for young women, and apparently, a sense of humor when it comes to names. We met through an online platform that specializes in these kinds of “arrangements,” a place where sugar babies and daddies swarm like bees around honey. The deal is simple. He gives me a monthly allowance that covers my tuition, books, rent, and a little extra for living expenses, and in return, I give him what he desires—my time, my attention, and my body.
Now, Richard isn’t what you’d call a looker, but he does have one feature that’s undeniably… substantial. He has a big cock, one that could make a porn star green with envy. It’s not just long, it’s thick, veiny, and heavy, the kind that makes you gulp when you first lay eyes on it. When it comes to my job, I mean, my “arrangement,” let’s just say I’ve had to become a bit of a size queen. It’s not something I’d admit to my friends, but I’ve learned to appreciate the… assets that come with the territory. And believe me, Richard knows exactly how to wield that weapon.
Our encounters are always the same—dinner at an upscale restaurant, a fancy hotel room with a view of the city, and a night of passion that would make even the most seasoned adult film star blush. He’s not exactly gentle, but there’s something about the way he takes control that sends shivers down my spine. When he unzips his pants and pulls out that monster, I can’t help but feel a mix of fear and excitement. The way it fills my mouth, my throat, my pussy… it’s overwhelming. But it’s not all about the size, it’s his dominance, his hunger for me that gets me wet, that makes me want to please him in every way imaginable.
As we lay there in the plush hotel bed, my body aching from his relentless pounding, I can’t help but wonder if this is what the future holds for me. Sure, the money is good, and the sex is… interesting, but is this what I want to be known for? The girl who got through college because she could deep-throat a man old enough to be her grandpa? I try to ignore the voice in the back of my head telling me I could be doing so much more, that I’m wasting my potential. But then again, when his cock is pumping deep inside me, and he’s whispering sweet nothings into my ear, the thought of pre-med or law school seems so… trivial. So, I push those thoughts aside, and I focus on the here and now, on the feel of his hands on my body, his hot breath on my neck, and the sweet taste of his cum on my lips. For now, this is my life, and I’m going to make the most of it.
But tonight is different. After the usual dinner and small talk, Richard surprises me. He tells me he has something special planned, a little treat for being such a good girl. We enter the hotel suite, and the room is dimly lit with scented candles flickering on every surface. He leads me to the bed, and before I know it, he’s kissing me, his hands roaming my body, teasing my breasts, and making my nipples stand at attention. His tongue darts into my mouth, and I can’t help but moan as he bites my bottom lip. Then, without warning, he pushes me down, his mouth descending to my neck, leaving a trail of kisses and gentle bites that make me squirm with pleasure.
He spreads my legs wide, and for the first time, I feel his hot breath on my pussy. His tongue darts out, flicking against my clit, sending shockwaves of pleasure through my body. He’s never gone down on me before, always preferring the more traditional methods of penetration. But tonight, he’s different, more attentive, as if he’s discovered a new toy and is eager to explore every inch of it. He licks and kisses me, teasing my folds, before finally settling on my clit, sucking it into his mouth like it’s the most delicious piece of candy he’s ever tasted. My hips buck as I try to get closer, to feel more of him, and he responds by pressing his tongue harder against me.
The sensation is intense, and my moans fill the room. It’s been so long since anyone’s paid this much attention to my pleasure, and it’s driving me wild. His beard scratches against my inner thighs, adding an extra layer of sensation to the mix. I’ve never been with a man who’s this hairy, but in this moment, I can’t think of anything but how good it feels. His hands are everywhere, kneading my breasts, pinching my nipples, sliding down to spread my ass cheeks apart. He’s devouring me, his hunger palpable in every lick and nibble. And I’m loving every second of it.
As he continues to feast on my pussy, I feel an orgasm building, starting as a small tremor in my core and spreading outwards like ripples in a pond. My muscles tense, my toes curl, and my nails dig into the sheets. He senses it too, and his pace quickens. His tongue is a masterful artist, painting a picture of pleasure on my clit that’s so exquisite, I think I might just pass out. And then, with one final, hard suck, I cum, my body arching off the bed as wave after wave of ecstasy crashes over me. It’s the kind of orgasm that leaves me boneless, my legs shaking uncontrollably as I try to catch my breath.
After a moment, Richard stands up, his face glistening with my juices, and smirks down at me. Without a word, he undoes his pants and pulls out that thick, meaty cock of his. It’s already hard and ready for action, and the sight of it makes my pussy clench with anticipation. He slides it into me, and I gasp at the sudden fullness. It’s like being filled by a velvet-covered battering ram, stretching me wide open and pushing all my buttons at once. He’s not gentle, but the tenderness of his earlier ministrations has made me wet and eager, so he slides in easily despite his size.
As he starts to fuck me, our tongues tangle together, a dance as old as time. He tastes faintly of mint, but underneath that, there’s a hint of me, a musky flavor that only adds to the intimacy of the moment. We kiss deeply, passionately, our breaths mingling as we move together in a rhythm that’s become almost second nature to us. His strokes are strong and sure, and I can feel every inch of him as he fills me up, his cock hitting spots I didn’t even know existed.
My eyes are closed tightly, my hands clutching at the bed sheets, as I try to keep up with the sensations crashing over me. His thrusts are punctuated by grunts that resonate in his chest, vibrating against my own. With each push, he hits a spot inside me that makes me see stars, and I moan into his mouth, my body begging for more. It’s a delicious agony, a sweet surrender to the power he holds over me. I’ve never felt so alive, so consumed by desire.
Just when I think I can’t take it anymore, that I’m going to shatter into a million pieces from the sheer force of pleasure, he surprises me. Richard pulls out of my pussy, and before I can even process what’s happening, he’s flipped me onto all fours, my ass in the air, exposed and vulnerable. I feel a brief moment of panic, a whisper of fear as his cock, still slick with my juices, nudges against my tight asshole. It’s been a while since anyone’s been there, and the thought of taking his size is daunting. But then he whispers in my ear, “You’re mine, Jessi,” and something inside me relaxes.
He doesn’t just plunge in; he takes his time, lubing me up with gentle strokes of his thumb, circling my asshole, teasing me until I’m begging for it. And then, with one swift, decisive move, he pushes the head of his cock inside. I gasp, my eyes watering, but it’s not pain, it’s… different. A new kind of fullness that makes me feel like I’m being split in two. He holds still, giving me a moment to adjust, and then, with a growl, he starts to push deeper.
Inch by inch, he fills me up, my body stretching to accommodate his girth. I’ve never been so aware of every sensation, every nerve ending in my ass. It’s an odd mix of pleasure and pain, a tightness that borders on the uncomfortable but is somehow… intoxicating. He’s so much bigger than anyone I’ve ever been with, and the thought of taking all of him sends a thrill through me that’s equal parts terror and excitement. He’s gentle at first, his strokes measured, but as my body relaxes and starts to move back into him, he picks up the pace.
The room is filled with the sound of skin slapping against skin, the slick noise of his cock moving in and out of my ass. I’ve never felt so wanton, so completely used. And yet, there’s a power in it, a sense of control that I didn’t expect. He’s mine, just as much as I’m his, and the knowledge that I can make him feel this good is heady. His hand reaches around, finding my clit, and he starts to rub it in circles, his thumb pressing down hard as he fucks me deeper.
My body responds to his touch, my pussy clenching around his cock, my ass taking him in like it’s been waiting for this moment its whole life. It’s an animalistic, primal feeling, one that has me panting and moaning like a bitch in heat. And as he fucks me harder, faster, his grip on my hip tightening, I realize that I’m going to cum again. This orgasm is different from the last one—it’s more intense, more visceral, as if my entire being is focused on the point where his cock meets my body.
He seems to sense my impending climax, because he speeds up, his strokes growing shorter and more erratic. He’s close, I can feel it in the way his body tenses, in the desperation in his breath. And then, just when I think I can’t take anymore, he reaches around and pinches my clit hard, sending me spiraling over the edge. My walls clamp down around his cock as I scream out his name, the pleasure so intense it’s almost painful.
The orgasm rips through me like a tornado, leaving me shaking and gasping for air. Richard doesn’t stop though, he keeps fucking me through it, his hips slapping against my ass in a rhythm that’s almost cruel. But it’s what I need, what I crave. His hand is a blur between my legs, working my clit like he’s trying to break it off. And all the while, he’s groaning, his own release building.
With a final, desperate thrust, he cums inside me, filling my ass with his hot seed. The sensation is so intense, so overwhelming, that I can’t help but cry out, my nails digging into the bed. He holds still for a moment, his cock pulsing deep within me, and then slowly pulls out. I feel empty, used, and absolutely alive.
With a surprising gentleness, Richard flips me onto my back, his eyes gleaming with satisfaction. Before I can even process what’s happening, his mouth is on my ass, licking me clean. The feeling is indescribable—his warm tongue lapping at my still-twitching hole, tasting himself on me. It’s intimate, degrading, and oddly… thrilling. He’s never done this before, never shown such an interest in my body beyond his own pleasure, and the gesture sends a bolt of lust straight to my core.
As he licks me clean, his eyes never leave mine. They’re filled with a hunger that’s both terrifying and exhilarating. It’s as if he’s claiming me, marking his territory in the most primal way possible. His tongue is relentless, tracing the path of his cum up my crack and across my sensitive skin. He’s thorough, almost loving in his attention, and I can’t help but push my hips up to meet him, silently begging for more.
His beard tickles my thighs as he moves up my body, kissing and biting every inch of me as he goes. His cock is still semi-hard, glistening with a mix of our juices, and I’m surprised to find myself craving another round. Richard seems to sense my need because he doesn’t waste any time. He slides back into my pussy, which is still slick from his earlier attentions, and starts to fuck me again. This time, it’s slower, more deliberate, as if he’s savoring every moment.
The head of his cock hits my g-spot with each thrust, sending shockwaves of pleasure through my body. I’ve never felt so alive, so utterly consumed by someone else’s desire. His eyes are on mine, watching every expression that flits across my face, as if he’s memorizing them. It’s like we’re connected by a string of pure, unfiltered lust, and he’s pulling on it, controlling me like a marionette. I wrap my legs around his waist, urging him deeper, my hips moving in time with his.
Our bodies are a symphony of flesh, each movement creating a crescendo of sensation. His cock stretches me, filling me so completely that it’s as if I’ve been made for him and him alone. The room is hot, the air thick with the scent of sex, and I can’t get enough of it. The bed creaks under us, a testament to our passion, as we move together in a dance that’s been performed since the dawn of time.
Finally, with a guttural groan, he cums again, his cock pulsing inside me, releasing a hot flood that seems to go on forever. I follow suit, my pussy contracting around him as my orgasm takes hold. It’s a feeling so intense, so all-consuming, that it’s almost painful. And yet, as the last spasms of pleasure die down, I find myself already eager for more.
As Richard rolls off me, his breathing heavy, I can’t help but feel a twinge of disappointment. He collapses onto his back, one arm thrown over his eyes, and within minutes, he’s snoring lightly. It’s a sound that’s become oddly comforting over the months we’ve been seeing each other—the sound of a job well done. But tonight, as the afterglow of our encounter starts to fade, I feel a strange restlessness. I don’t want the night to end just yet.
So, I do the only thing I can think of—I grab my chemistry textbook from my bag. It’s a weighty tome that I’ve been avoiding all week, but now, as the silence of the hotel room presses down on me, it seems like the perfect escape. I’ve got an exam in the morning, and while the thought of atoms and molecules is hardly as titillating as what we just did, there’s something comforting about diving into the orderly chaos of science. Plus, it’s the kind of thing that keeps my mind off the fact that I’m lying here, naked and sore, next to a man who could be my grandfather.
I flip through the pages, the words blurring together as I try to focus. But the scent of our sex still lingers in the air, and it’s hard to ignore the sticky wetness between my legs, the feeling of his cum leaking out of my ass. I can’t help but glance over at him, his chest rising and falling with each deep breath, his body sprawled out in a way that’s both comical and a little pathetic. Yet, there’s something almost… endearing about it.
The truth is, Richard isn’t just my sugar daddy. He’s also become a surprisingly good fuck, a man who knows exactly how to push my buttons and make me cum harder than I ever thought possible. Sure, the arrangement is transactional, but the chemistry between us is undeniable. And as much as I might try to convince myself that this is just a means to an end, a way to pay for my education and keep a roof over my head, I can’t help but feel a twisted sense of satisfaction when he looks at me like that—like I’m the only thing that matters in the world.
As I lay there, the sweat drying on my skin, I can’t help but think about what he said before we started, that he had a special treat for me. Was it the way he ate me out, the gentle, almost loving way he took my ass? Or was it something more? Was this his way of saying he cared about me, beyond the terms of our agreement? It’s a thought that sends a shiver down my spine. Could I… could I actually care for him too?
I push the book aside and roll over to face him. The candlelight casts shadows across his face, making him look almost… vulnerable. He’s not just some rich old man with a big dick and an even bigger wallet anymore. He’s a person, with wants and needs and feelings. And as much as I’ve tried to convince myself that this is just a job, that I’m not getting attached, the truth is, I am. There’s something about the way he makes me feel, something beyond the physical. It’s like he sees me, really sees me, and it’s intoxicating.
ASK JESSI 
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