Being a sexless, cumless simp for a beautiful woman sounds like a fair trade to me

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@sissy-wimp
Being a sexless, cumless simp for a beautiful woman sounds like a fair trade to me

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Making an entrance on Pink Wednesday.

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Sex isnt for you my little sockssexual beta loser. You must always know your place.
Goodboys like you destroy nasty broken beta sperm inside my dirty used socks, toilet or trash.
i know that i don't deserve any pussy. i'm a loser with a tiny peepee, and no female should want anything to do with me!
Pussyfree since 5th September 25
there is no dought that I will be pussyfree for life
I want a gf like that … see that smile
I would so do this

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With apologies to Prissy
The Nymphomaniac — Part IV: The Demonstration
You ring her doorbell on a Thursday evening.
Your palms are damp. Your heart is doing that familiar, frantic drumming against your ribs.
Your cock has been in a state of semi-arousal for forty-eight hours, twitching at the memory of her fingers on the cardboard roll, of Caleb's cock splitting her open and filling her pussy on the screen.
You’ve been thinking about her all day—about the calibration session, about the videos she promised, about the censored tapes Jordan is making.
The door opens.
She’s there, smiling that warm, certain smile. She looks cozy. Approachable. Safe.
“Hi, sweetie,” she says, stepping aside to let you in. “Come on in. We’ve been waiting for you.”
We.
You step into her apartment. The air smells like vanilla candle. The living room is softly lit. And there, on the sofa, sits another woman.
She’s about the same age as your girlfriend. Pretty, with blonde hair, bright blue eyes, and a wide, friendly mouth. She smiles when she sees you, vibrant and sensual.
“This is Jessica,” your girlfriend says, closing the door behind you. “My best friend. Jess, this is him.”
Jessica’s eyes sweep over you. They linger on your face, then drop briefly to your crotch before returning to your eyes.
“Hi,” she says, her voice cheerful. “I’ve heard so much about you.”
You manage a nod. “Hi.”
Your girlfriend takes your hand and leads you further into the room. She doesn’t guide you to the sofa. She stops you in the middle of the carpet, facing both of them.
Jessica is still sitting, leaning back, one arm draped along the back of the cushions. Your girlfriend stands beside you, her hand still in yours.
“We’ve been talking,” your girlfriend says, her thumb stroking your knuckles. “Jessica and I. About you. About the big day.”
Your throat tightens. “The big day?”
“The day we have sex, sweetie,” she says, as if reminding you of something obvious. “The day you finally put your little guy inside my pussy. We’re worried.”
Jessica nods, her expression turning serious. “We’re really worried.”
“Worried?” you echo.
“That you’re going to choke,” your girlfriend says softly. “That it’s all going to be too much for you. Sex intimidates you. We know how scary it is for you. We want to make it safer. More comfortable.”
Jessica leans forward. “We think you might need a demonstration. Some educational help.”
You stare at them. Your mind is scrambling. “A demonstration?”
“Of sex,” Jessica says, as if it’s the most natural thing in the world. “So you can see it isn’t so scary. So you can watch it happen and realize it’s just… bodies. Mechanics. Pleasure.”
Your girlfriend squeezes your hand. “We thought maybe we could sit down and talk about it. Figure out a plan. Would that be okay?”
You nod, because you don’t know what else to do. You’re being led, gently but firmly, to the sofa. Your girlfriend sits in the middle.
She pats the cushion to her left. You sit. Jessica is to her right, curling one leg beneath her, turning her body to face both of you.
For a moment, no one speaks. The vanilla candle flickers. The silence feels heavy, expectant.
Then your girlfriend speaks, her voice a soothing murmur. “We thought maybe… if you could watch someone else do it first. Someone you trust. Then it wouldn’t be so overwhelming when it’s your turn.”
Your blood goes cold. Then hot. “Watch someone else?”
“Have sex,” she clarifies, her eyes soft with concern. “Someone you trust completely. So you know they wouldn’t take advantage. So you know they’d be gentle. Educational.”
Jessica nods enthusiastically. “A teaching moment. Like a… live tutorial.”
Your mind is reeling. You look from your girlfriend’s calm, caring face to Jessica’s eager, bright-eyed one. “Who?” you manage to ask.
“That’s what we wanted to ask you,” your girlfriend says. “Who do you trust? Really, truly trust? A friend, maybe?”
Your thoughts scramble. Friends. You have a few. But trust? Completely? With her?
“Mark,” you hear yourself say. The name falls out of your mouth before you can catch it. “My best friend. Mark. I trust him.”
Your girlfriend’s face lights up. “Mark! Yes. You’ve mentioned him. He sounds wonderful. Solid. Dependable.”
Jessica is beaming. “Perfect! That’s perfect.”
You feel a surge of relief, followed immediately by a dizzying wave of confusion. “Perfect for what?”
Your girlfriend turns her body fully toward you. She takes both your hands in hers. Her gaze is earnest. Tender.
“We think you should ask Mark to fuck me,” she says, her voice low and gentle, as if she’s proposing a mild medication.
“Because you trust him not to take advantage of the situation. He’ll do it for you. As a favor. To help you. He’ll fuck me while you watch. So you can see it isn’t so scary. So you can see how it works. How I react. How… normal it is.”
The room tilts. The words hang in the air, shimmering with impossible, terrible clarity.
Ask Mark to fuck me.
While you watch.
You open your mouth. No sound comes out.
Jessica is talking now, her voice quick, practical. “We’ve already thought about logistics. He could come over here. Or we could do it at my place. My place is bigger. And I have a better sofa for spectators.”
“Spectators,” you whisper.
“You,” Jessica says, smiling at you. “The student.”
Your girlfriend is watching your face. She sees the panic. She sees the arousal—because you can feel it now, a thick, insistent heat pooling in your groin, your cock stirring against the fabric of your jeans. She sees the conflict. She smiles, a soft, understanding smile.
“It’s okay to be overwhelmed,” she murmurs. “All this talk about sex must be so much for you.” Her hand releases yours and comes to rest on your thigh. “Your little guy is reacting. That’s natural. It’s a natural response to a charged conversation.”
Jessica’s eyes drop to your lap. She giggles—a light, airy sound. “Oh, wow. He is definitely reacting.”
Your girlfriend follows her gaze. She sees the tent in your jeans. She giggles too, a softer, more intimate echo. “He is. Poor thing. All this talk about his best friend fucking me… it’s stirring him up.”
You want to cover yourself. You want to run. But you’re frozen, pinned by their combined gaze, by the warmth of her hand on your thigh, by the brutal, thrilling image taking shape in your mind—Mark, your best friend since high school, between her thighs, pushing into her, fucking her while you watch.
“You know,” your girlfriend says, her voice thoughtful, “maybe you should show Jessica how you hump your roll now. Since you’re so worked up. It might help you focus. Release some of that tension.”
Humiliation floods you, hot and thick. “I… I don’t have it.”
“I do,” she says. She nods toward the kitchen. “There’s a fresh one in the recycle bin under the sink. Would you go get it, sweetie? For us?”
It’s not a question. It’s an instruction.
You stand up. Your legs feel weak. You walk to the kitchen, your erection pressing painfully against your zipper. You open the cabinet under the sink. There, among the empty cans and bottles, is a clean, empty cardboard toilet paper roll. You pick it up. It feels light. Insignificant. A ridiculous object.
You carry it back to the living room like a security blanket.
They are talking in low, soothing tones as you approach.
“…just so much for him to process,” Jessica is saying.
“I know,” your girlfriend replies. “But we have to be patient. He’s trying so hard.”
You stop in front of them. You hold out the roll.
Your girlfriend takes it. Her fingers brush yours. “Thank you.” She pats the cushion beside her again. “Sit back down. Let’s get you comfortable.”
You sit.
“Now,” she says, her voice gentle but firm. “Why don’t you pull down your pants and underwear? So you can really get into it. So you can show Jessica your technique.”
Your face is on fire. You look at Jessica. She’s watching you, her head tilted, a small, encouraging smile on her lips.
“It’s okay,” Jessica says. “We’re all friends here. This is a safe space.”
Your hands move on their own. They fumble with your belt buckle. They pop the button of your jeans. They pull down the zipper.
You lift your hips and push your jeans and boxer briefs down to your knees. Your cock springs free, fully hard, curving up toward your stomach. The head is already wet, gleaming in the soft light.
You hear Jessica’s soft intake of breath. “Oh,” she says. “He’s really… ready.”
Your girlfriend holds the roll for you. “Go ahead, sweetie. Show her how you do it. How you train.”
You guide the tip of your cock into it. You push until you’re sheathed to the base. The fit is snug, familiar, a pathetic mockery of the real thing.
“Good,” your girlfriend murmurs. She scoots closer to you on the sofa, her thigh pressing against yours. “Now, just relax. Do what feels natural. We’re going to talk some more about the plan. You just… listen. And practice.”
You begin to move your hips. Small, shallow thrusts. The cardboard rubs along your shaft. The sensation is immediate, electric. You close your eyes.
“So,” your girlfriend says, her voice shifting to a conversational tone. “Mark. You really think he’d do it?”
You keep your eyes closed. You hump the roll. “I… I don’t know.”
“He’s your best friend,” Jessica says. “If you asked him as a favor, to help you get over your fear… I bet he would. Guys do stuff like that for each other, right?”
“He’s a good guy,” your girlfriend adds. “From what you’ve said. He wouldn’t be jealous. He’d be… educational.”
You hump faster. The image is there, sharp and vivid: Mark, naked, kneeling between her spread legs. Mark, pushing into her pussy. Mark, fucking her with slow, deliberate strokes. Mark, making her moan.
“Does he have a girlfriend, though,” Jessica says, a note of practical concern in her voice. “Would that be a problem?”
Your girlfriend sighs. “If he did it might. We’d have to explain it’s just a demonstration. A clinical thing. For educational purposes.”
“Right,” Jessica says. “Not cheating. Just… community service.”
They both giggle. The sound is light, dismissive. They aren’t looking at you.
You can feel their attention shift away from you, toward each other, toward the plan. You are furniture. A piece of the scenery, humping a cardboard tube on the sofa.
You open your eyes. They are facing each other now, leaning in slightly, talking over you as if you’re not there.
“My place is definitely better,” Jessica is saying. “I have that big sectional. He could sit right there, have a perfect view. And the lighting is good.”
“Lighting is important,” your girlfriend agrees. “For the educational value.”
“Plus,” Jessica says, her voice dropping to a conspiratorial whisper, “I have my equipment.”
“Equipment?”
“For recording,” Jessica says, her eyes bright. “I have a nice camera. A tripod. We could record the whole thing. That way he could have it forever. He could watch it over and over. Really study it. Until he’s comfortable.”
Your girlfriend makes a soft, considering sound. “Record it… That’s a wonderful idea, Jess. A permanent reference. For his training.”
You’re humping furiously now. Your hips are pistoning, driving your cock into the cardboard tube with wet, slapping sounds.
The friction is incredible. The mental image—Mark fucking her, recorded, a video you could own—is pushing you toward the edge.
“And,” Jessica says, her tone becoming excited, “we could stream it.”
Your girlfriend pauses. “Stream it?”
“On my OnlyFans,” Jessica says, as if it’s the most obvious thing in the world. “I have a page. My fans love live content. They’d go crazy for this. ‘Virgin’s Educational Demonstration: Best Friend Fucks Girlfriend While He Watches.’ It’s got a great hook. Very niche. Very hot.”
Your girlfriend is silent for a moment. You can feel her thinking. You keep humping, your breath coming in ragged pants, your balls drawing up tight.
“Would that be okay?” your girlfriend asks, her voice soft. “To have strangers watching?”
“They wouldn’t be strangers,” Jessica says. “They’re my fans. They’re supportive. And they’d be rooting for him! They’d be cheering him on, in a way. Watching him learn. It would be… interactive. Motivational.”
Another giggle. “Plus, the tips would be amazing. We could split them. Use the money to… I don’t know, buy him a better training aid. A fleshlight or something.”
They both laugh. The sound is warm, amused. Dismissive.
You are nothing. You are a thing on the sofa, humping a tube, while they discuss monetizing your humiliation, your fear, your best friend fucking your girlfriend for an online audience.
And you are desperately, unbearably aroused.
Your thrusts become frantic, uncontrolled. The cardboard is wet with your precum, the sound obscene in the quiet room.
Jessica glances at you. Her eyes widen. “Oh, wow. Look at him go. He’s really humping hard.”
Your girlfriend turns her head to look at you. Her expression is one of gentle approval. “He is. He’s a visual learner. The idea of having a recording… of seeing Mark and me… it’s really working for him.”
She reaches out and places a hand on your bouncing thigh. Her touch is steadying. “It’s okay, sweetie. You can cum if you need to. This is a lot to process. Your little guy needs the release.”
Her permission is the final trigger. With a choked, guttural cry, you slam your hips forward one last time and erupt.
Thick ropes of cum shoot into the cardboard tube, spattering against the far end with a series of wet, hollow pops.
You shudder through it, fucking the roll through your climax, each convulsion milking out another spurt until you’re spent, gasping, collapsing back against the sofa cushions.
Your girlfriend keeps her hand on your thigh until the spasms subside. Then she carefully slides the roll off your softening, messy cock. She peers inside.
“He filled it up again,” she says, a note of pride in her voice. She holds it out to Jessica. “See?”
Jessica takes the roll, looks into it. She grins. “Impressive. For a virgin.” She sets the soiled roll on the coffee table.
For a long moment, there is only the sound of your ragged breathing.
Then your girlfriend moves. She takes a tissue from the box on the end table. She cleans you with gentle, efficient swipes. She helps you pull up your underwear and your jeans. Her touch is tender. Almost maternal.
“You did so well,” she murmurs, zipping you up. “That was a very productive discussion. We have a plan now. A good, solid plan.”
Jessica is nodding, her excitement barely contained. “Maybe you should give me Mark's number. I’ll text him tomorrow,” she says. “Feel him out. See if he’s open to it.”
“No,” your girlfriend says softly. She looks at you. “He should ask Mark. It should come from him. As a personal favor. It’ll mean more that way.”
You stare at her. Your mind is blank, wiped clean by the orgasm, by the sheer absurdity of what they’re suggesting.
“You’ll ask him, won’t you, sweetie?” she says, her hand coming up to cup your cheek. “For us? For your education?”
You nod. You have no will left.
“Good,” she whispers. She leans in and kisses your forehead. “My brave, brave boy.”
She stands. Jessica stands too. They both look down at you, sitting there with your pants zipped, your body humming with aftershocks, your soul hollowed out.
“We’ll let you process,” your girlfriend says. “We're going out to the club. Just lock the door on your way out. I’ll text you tomorrow. We can talk about how to approach Mark.”
Jessica gives you a little wave. “Nice to meet you. Really. This was fun.”
They walk to the door together. They step out into the hallway. You hear their voices, fading as they walk away, giggling, talking about cameras, angles, lighting.
The door swings shut.
You sit on her sofa, the smell of sex and cardboard and vanilla candle thick in the air.
You look at the soiled toilet paper roll on the coffee table.
You think of Mark.
You think of her, spread open, taking him.
You think of the camera recording it.
You think of strangers watching, tipping, cheering.
Your cock, soft and spent, gives a feeble twitch.
It’s already decided.
It wants the demonstration.
It wants to watch.
It wants to be educated.
This is the fourth in a series about a woman, a virgin, and the dangerous, delicious question of what happens when she decides his first time should be with her — and his only time might be, too.
Previous: The Nymphomaniac Part I | The Nymphomaniac Part II | The Nymphomaniac Part III
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The Nymphomaniac — Part V: The Live Stream
The day arrives.
You wake with a hollow, fluttering panic in your gut. It’s been three days since you asked Mark. Three days of stuttered texts, awkward phone calls, his confused but ultimately compliant agreement.
“If it’ll help you, man. I guess. Yeah. I’ll do it. I'll fuck your girlfriend.”
You dress in simple clothes—jeans, a t-shirt. You feel like you’re preparing for a medical procedure.
Mark picks you up at noon. He’s quiet. Pale. He keeps clearing his throat.
“You sure about this?” he asks, for the tenth time, as he drives toward Jessica’s apartment.
You nod. You aren’t sure about anything. But your cock is already stirring, a throb of anticipation. “It’s just a demonstration,” you say, repeating the phrase your girlfriend has used so often. “Educational.”
Mark grunts. He doesn’t look convinced.
Jessica’s apartment building is modern, sleek. You take the elevator to the twelfth floor in silence. The air between you is thick with unspoken dread.
You ring the bell.
The door opens almost immediately. Jessica stands there, beaming. She’s wearing a tight black tank top and tiny shorts. Her blonde hair is piled in a messy bun. She looks like a fitness influencer about to film a workout.
“Hey, boys!” she says, her voice bright and welcoming. “Come on in! We’re all set up.”
You step inside. Mark follows, his shoulders hunched.
The apartment is spacious, minimalist. The living room has been transformed. The large sectional sofa is pushed against one wall. In the center of the room, a professional-looking camera is mounted on a tripod. Lights on stands cast a bright, clinical glow over a king-sized bed that has been positioned where a coffee table might normally be. The bed is made with crisp white sheets.
Your girlfriend is sitting on the edge of the bed. She’s in a matching lace bra and panties—black, delicate.
Her hair is down, her lips are red. She smiles when she sees you, but it’s a different smile. It’s a performer’s smile. Warm, but distant. Prepared.
“Hi, sweetie,” she says. “Hi, Mark. Thank you so much for doing this.”
Mark mumbles something. He’s staring at the camera, the lights, the bed.
A man steps out from behind the camera. He’s tall, broad-shouldered, with close-cropped dark hair and a confident, easy stance. He’s wearing jeans and a plain grey t-shirt that strains over his chest and arms.
“This is Tom,” Jessica says, gesturing to him. “My boyfriend. He’s going to be running the camera today. Normally he's the star.” She winks.
Tom nods at you both. “Hey.” His voice is deep, calm. He looks at you, then at Mark, his gaze assessing. He doesn’t seem nervous at all.
“Okay!” Jessica claps her hands together. “So, here’s the plan. We’re going live on my OnlyFans in about fifteen minutes. The title of the stream is ‘Virgin’s First Lesson: Live Demonstration.’ The fans are already hyped. The chat is popping off.”
She points to a small loveseat that has been placed at the foot of the bed, facing it. “That’s the bench. You'll will sit there. You’ll have a perfect view while Mark is on camera.”
You look at the loveseat. It’s small. Intimate. You will be sitting, naked, watching your best friend fuck your girlfriend. Your cock throbs.
“Mark,” your girlfriend says, her voice gentle. “Why don’t you get undressed first? Get comfortable. The stream starts soon.”
Mark looks at you, a flash of pure terror in his eyes. He swallows. Then, with stiff, robotic movements, he begins to undress. He toes off his shoes. He pulls his t-shirt over his head. He unbuttons his jeans, pushes them and his boxers down, steps out of them.
He stands there, naked, his arms crossed over his chest. His penis is soft, small, nestled in a thatch of dark hair. He’s shivering slightly.
“Good,” Jessica says. She points to the bed. “Have a seat. Get used to the lights.”
Mark walks to the bed and sits. He keeps his arms crossed, his knees together. He looks like a patient in a waiting room.
“Your turn, sweetie,” your girlfriend says.
You undress. Your hands don’t shake. You feel detached, floating. You fold your clothes neatly and place them on a chair by the door.
You walk to the bench and sit facing Mark. The leather is cool against your bare skin.
Tom is behind the camera, adjusting a dial. “Sound check,” he says. His voice booms slightly in the quiet room.
Your girlfriend stands up from the bed. She walks toward you, her hips swaying. She stops in front of you. She looks down at your laps. Your cock is already half-hard, thickening under her gaze.
She looks at Mark on the bed. His is still soft.
She reaches out and cups Mark’s cheek. “It’s okay to be nervous,” she murmurs. “Just remember, this is for him.” She gestures to you. “You’re helping your best friend. That’s a beautiful thing.”
Mark nods, his jaw tight.
She turns her attention to you. Her hand strokes your hair. “And you. My brave, brave boy. You’re going to learn so much today.”
Her fingers trail down your neck, over your chest, and give your nipple a gentle pinch. A bolt of arousal shoots straight to your cock, which jumps, filling further.
She smiles, satisfied. Then she turns and walks back to the bed. She lies down on her back, arranging herself against the pillows. She spreads her legs slightly, the black lace of her panties a dark contrast against her pale thighs.
“We’re live in five,” Tom says, his eye pressed to the camera’s viewfinder. “Chat is already at five hundred waiting.”
Jessica bounces on her toes, excited. She picks up a tablet from a side table. “Ooh, they’re going wild. So many questions. ‘Is the virgin really there?’ ‘Is the friend cute?’ ‘Can’t wait to see him give the virgin his lesson.’” She giggles.
Mark flinches.
“Three minutes,” Tom says.
The room grows quiet. The only sound is the faint hum of the lights. You can hear your own heartbeat in your ears.
“Okay, Mark,” your girlfriend says from the bed. Her voice is soft, encouraging. “Come here. It’s time.”
Mark stands up. His legs seem unsteady. He walks to the side of the bed. He stands beside it, looking down at her. At her body. At the camera pointed at them.
“It’s just us,” she says, patting the space beside her. “Just a demonstration. Ignore the camera.”
Mark climbs onto the bed. He kneels between her spread legs. He’s breathing heavily.
“Take off my panties,” she whispers.
Mark’s hands tremble as he hooks his fingers into the sides of her black lace panties. He pulls them down her legs, slowly. He drops them on the floor.
She is naked now from the waist down. Her pussy is neatly trimmed, lips plump and pink. You can see the glistening wetness already there.
Mark stares. His Adam’s apple bobs.
“Touch me,” she says.
He reaches out a hand. His fingers brush her inner thigh. They hover near her folds.
“Two minutes,” Tom says, his voice flat, professional.
Mark’s hand retreats. He looks at the camera. At the red light now glowing on its side. He looks at the bright lights, at Jessica watching eagerly with her tablet, at you on the bench. His breath hitches.
“It’s okay,” your girlfriend says, her voice still gentle. “Just relax. Pretend it’s just you and me.”
Mark nods. He tries again. He places a hand on her thigh. He leans forward, as if to kiss her. Then he freezes.
You can see it happen. The tension seizes him. His shoulders lock. His back goes rigid. He looks from the camera to her face, and his eyes are wide with pure, animal panic.
“One minute,” Tom says.
“Mark,” your girlfriend says, a note of impatience creeping into her tone. “We’re live soon. You need to get started.”
Mark tries to move. He shifts his weight. He brings his other hand to her hip. He lowers his head toward her chest. But his movements are jerky, unnatural. He’s trembling.
The red light on the camera blinks once, then stays solid.
“We’re live,” Tom says.
And Mark chokes.
It’s not dramatic. It’s a quiet, total shutdown. His body goes still. His penis, which had shown a faint sign of life, shrinks completely, becoming a soft, small nub against his thigh. He just kneels there, paralyzed, staring at the camera lens as if it’s the eye of a predator.
Your girlfriend’s smile falters. She reaches up and touches his arm. “Mark. Sweetie. It’s okay. Just breathe.”
But Mark is gone. He shakes his head, a tiny, desperate motion. “I can’t,” he whispers, the words picked up by the microphone. “I’m sorry. I can’t.”
A burst of laughter comes from Jessica’s tablet. She looks at it, her eyes widening. “Oh, wow. The chat is roasting him. ‘LMAO he’s terrified.’ ‘Stage fright!’ ‘This is pathetic.’ ‘Refund!’”
Humiliation floods Mark’s face. He tries to cover himself with his hands.
Your girlfriend sits up. She looks from Mark’s terrified face to the camera, to the chat on Jessica’s tablet. Her expression hardens, just for a second.
Then it softens into one of gentle concern. She pats Mark’s cheek. “It’s okay. It’s a lot of pressure. Why don’t you go sit with him for a bit?” She nods toward you.
Mark scrambles off the bed, his face burning with shame. He hurries to the bench and sits beside you, his head hanging, his hands in his lap.
Jessica steps forward, her business face on. “Alright, folks!” she says brightly, addressing the camera.
“Looks like our guest teacher needs a minute! No worries—we always have a lesson plan B!” She turns to your girlfriend. “What if Tom steps in? You know, a professional demonstrator. For educational clarity.”
Your girlfriend’s eyes light up. She looks at Tom, who is still behind the camera. “Would you, Tom? For the sake of the lesson?”
Tom doesn’t hesitate. “Sure.” He steps out from behind the camera. “Jess, take over filming.”
Jessica hands him the tablet and slips behind the camera. Tom looks at the tablet, scrolling through the chat. He smirks. “They’re saying the benchwarmers are both soft. Let’s see if we can change that.”
He puts the tablet down. Then, with calm, deliberate movements, he begins to undress. He pulls his t-shirt over his head, revealing a sculpted chest, defined abs. He unbuttons his jeans, pushes them down. He isn’t wearing underwear.
His cock is already thick, heavy, semi-hard. It’s not as monstrous as Caleb’s, but it’s impressive. Substantial. It swings as he steps out of his jeans. His balls are full, hanging low.
He walks to the bed, completely at ease. He kneels between your girlfriend’s legs, right where Mark had been. He doesn’t look at the camera. He looks at her.
“Ready for your lesson?” he asks her, his voice a low rumble.
She smiles, a real, hungry smile. “Yes. Please.”
Tom doesn’t hesitate. He doesn’t tremble. He leans forward, one hand braced beside her head, the other guiding his cock. He pushes into her in one smooth, confident stroke.
Your girlfriend’s back arches off the bed. A sharp, genuine gasp tears from her lips. “Oh, fuck, Tom.”
He begins to move. Deep, measured, powerful thrusts. Her body rocks with each one. The sound is immediate—wet, rhythmic, the slap of his hips against her thighs.
You watch, transfixed. So does Mark.
And as you watch, something happens.
Your cock, which had been half-hard, surges to full, aching erection. It stands up, curving toward your stomach, the head already dripping with precum. You hear a soft intake of breath beside you. You glance over.
Mark is staring, his mouth slightly open. And his cock, which had been soft and shrunken, is now stiffening, rising from its nest of hair. It’s bigger than yours, but only just. He’s getting hard watching Tom fuck your girlfriend.
Jessica, behind the camera, notices. She giggles, the sound picked up by the mic. “Well, well! Look at the bench! The students are paying attention! They’re both pitching tents!”
Tom glances over his shoulder as he thrusts. He sees you both, hard and leaking. He grins. “They need something to do with those hard-ons. Jess, hand them their training aids.”
Jessica reaches into a bag beside the tripod. She pulls out two fresh, empty cardboard toilet paper rolls. She walks over to the bench and hands one to you, one to Mark.
“Here you go, boys,” she says, her voice cheerful. “You know what to do. Hump along with the lesson!”
You take the roll. It feels familiar. Comforting. Mark stares at his, confused.
“Just put your penis in it,” you hear yourself say, your voice hoarse. “And hump.”
Mark mimics you. He guides the tip of his cock into the tube. He pushes in. You both sit there, on the bench, naked, with cardboard rolls sheathing your erections.
On the bed, Tom is fucking your girlfriend with relentless, expert rhythm. He shifts her legs, drives deeper. She cries out, her fingers digging into his back.
“That’s it,” Tom grunts. “Take it. This is how it’s done. Pay attention, boys.”
You begin to move your hips. Small, shallow thrusts into the cardboard. The friction is dry, rough, but the visual—Tom’s thick cock plunging into her, her breasts bouncing, her face contorted in pleasure—makes it electric.
Mark starts to hump too. Tentatively at first, then with more urgency.
Jessica is back behind the camera, but she’s commentating. “Chat is going insane! They love this! They’re saying the bench is hotter than the main event!” She laughs. “They’re starting to bet! They’re betting on which of the benchwarmers will cum first! We’ve got odds!”
Humiliation burns through you, but it’s fused with a dizzying, unbearable arousal. You are being compared. You are being bet on. You are a sideshow.
Tom changes position. He pulls out, flips your girlfriend onto her hands and knees. Doggie style.
She’s now facing you and Mark directly. Her breasts swing beneath her. Her face is flushed, her eyes glazed. She looks right at you as Tom re-enters her from behind, a long, slow slide that makes her moan.
“Look at them, sweetie,” she pants, her eyes locked on yours. “Look at how hard they are for you. They’re learning. They’re so eager. Hump your rolls, boys. Hump for me.”
You obey. You fuck the cardboard tube in earnest now, your hips pumping, your breath coming in ragged gasps. Mark is doing the same beside you, his eyes glued to where Tom is connected to her.
“Jessica!” your girlfriend moans. “Show them! Show them the split screen!”
“On it!” Jessica says. You hear a click from the camera.
On a large monitor set up to the side, you see the feed change. The screen splits. On the left side, the main shot: Tom pounding into your girlfriend from behind, her body jolting forward with each thrust.
On the right side, a new shot, from a second camera you hadn’t noticed: a close-up of the bench. Of you and Mark, side by side, frantically humping your cardboard rolls, your faces tense with concentration and lust.
The chat on the tablet explodes. The text scrolls too fast to read, but you catch flashes: “BETA KINGS!” “$50 on the friend!” “Virgin boy is gonna blow first!” “This is the hottest shit ever!”
Tom is fucking her harder, faster. The bed creaks. Her moans become screams, punctuated by his guttural grunts.
“You gonna cum, boys?” he he says over her shoulder, not missing a stroke. “You gonna blow your loads in your little tubes while I blow mine in her pussy? Let’s do it together. A synchronized finish. For the stream.”
The idea—the three of you cumming together, you and Mark into cardboard, him into her—is the most degrading, most thrilling thing you’ve ever imagined. Your balls draw up tight, a familiar, urgent pressure building at the base of your spine.
You glance at Mark. His eyes are squeezed shut. His thrusts are frantic, erratic. A thin string of precum hangs from the end of his roll. He’s close too.
On the bed, your girlfriend is reaching her peak. “I’m gonna cum!” she shrieks. “I’m gonna cum! Don’t stop! Make them cum with me!”
It’s a command.
You let go. You surrender. You slam your hips forward, fucking the roll with abandon, your eyes locked on the split screen—on the left, her body convulsing as Tom drives into her one last time; on the right, your own desperate, humping form.
With a ragged, broken cry, you erupt. Hot cum pulses into the cardboard tube, jetting against the far end. A fraction of a second later, Mark lets out a choked sob and joins you, his body shuddering as he spills into his own roll.
On the bed, Tom roars, his body stiffening as he buries himself to the hilt inside her. Her back arches, a silent scream on her lips as she climaxes around him.
For a few seconds, the room is filled with the sounds of completion: your panting, Mark’s whimpers, Tom’s heavy breaths, her soft, continuous moans.
Then, silence.
The only sound is the faint hum of the lights and the rapid ding of tips coming through on Jessica’s tablet.
Tom pulls out slowly. He turns and looks at you and Mark, both of you slumped on the bench, spent, your rolls still on your softening cocks. He grins, a wide, easy grin.
“Good job, boys,” he says, slapping his thigh. “You kept up. You learned something.”
He walks over to the bench, naked, his own cock still glistening with her wetness. He claps a hand on your shoulder, then on Mark’s. “Seriously. You did great. Perfect timing.”
He says it like a coach praising his players after a game.
Jessica stops recording. The red light on the camera goes out. She bounces over, looking at her tablet. “That was AMAZING! The chat loved it! We got so many tips! And three new top-tier subscribers!”
She looks at you and Mark. “You two are naturals. The ‘beta bench’ is a hit. We have to do this again.”
Your girlfriend slowly sits up on the bed. She looks dazed, satisfied. She smiles at you, a warm, proud smile.
“You did so well, sweetie. You too, Mark. You both learned so much.” She stands, wobbly, and pulls on a robe that was draped over a chair. “That was a very successful demonstration.”
Mark carefully slides the soiled roll off his cock. He looks at it, then at the floor, his face blank.
You do the same. You set the wet, sticky tube on the floor between your feet.
Tom gets dressed. Jessica starts packing up her equipment. The stream is over. The lesson is complete.
You sit on the bench, naked, the smell of sex and cardboard and sweat thick in the air. Your girlfriend comes over, her robe loosely tied. She leans down and kisses your forehead.
“I’m so proud of you,” she whispers. “You took your education so seriously.” She straightens up. “Get dressed, sweetie. I’ll text you tomorrow. We can debrief.”
She walks away, joining Jessica and Tom, who are already discussing the metrics, the highlights, the possibility of a follow-up stream.
You pull on your clothes. Mark does the same, his movements slow, shell-shocked.
You leave Jessica’s apartment together. You ride the elevator down in silence. You get into Mark’s car.
He starts the engine. He doesn’t look at you.
He drives you home. When he pulls up to your curb, he finally speaks, his voice flat.
“I’m never doing that again,” he says.
You nod. “Okay.”
You get out of the car. You watch him drive away.
You walk into your empty apartment. You lock the door.
You stand in the middle of your living room. The memory of the split screen burns behind your eyes: her pleasure, your humiliation, side by side for the world to see.
Your cock, soft and spent, gives a feeble, aching throb.
It doesn’t care about never again.
It wants more.
It wants to be on the bench again.
It wants to be a good student.
This is the fifth in a series about a woman, a virgin, and the dangerous, delicious question of what happens when she decides his first time should be with her — and his only time might be, too.
Previous: The Nymphomaniac Part I | The Nymphomaniac Part II | The Nymphomaniac Part III | The Nymphomaniac Part IV
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Successful entrepreneur Janice had built a massive fortune for herself. So much so she decided to retire in her mid 40s. She wasn't interested in getting married or relationships, apart from the odd fling. But she did enjoy a project to keep her very active mind firing. And her latest project was Jamie. Jamie, formerly her ever loyal PA James, was 25 and on the surface a normal man in his mid 20s. But the perceptive mind of Janice knew he was different and not so long after becoming her PA she worked out his secret sissy fantasies. So when she retired she invited him over to her sprawling mansion and put her theory to him and offered him a position as her personal maid at her home. Through a combination of her own expert negotiating skills and his own desires, he agreed. But she had three non-negotiable conditions. One, she was completely in charge of him and he couldn't refuse any order or decision she made for him, (she assured him she would always act in his best interests). And two, this was not just dressing up and having some fun, he had allow her to completely feminize him , and three, be in chastity, in which she would be in control of his sexual release. James.es agreed and started in his towards becoming Jamie. She was a reasonable and caring Mistress, and allowed him to her as Miss Janice, and even encouraged him document his transformation on social media. In the scene above, Jamie was posing for a live stream, and she saw a golden opportunity to embarrass him. She new he secretly loved it and it would give his audience a thrill to see him bossed around, especially as Jamie had thoroughly washed and polished her car the day before, and given his followers a lovely and teasing show on a live stream as well.

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A new role in the office. Part Three.
Poor Martin, this wasn't the outcome of his visit to HR that he was hoping for.