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Crystal tries to avoid ranking the dates she’s been on recently, but Jason doesn’t do badly, she muses. He’s pulled out a chair for her before sitting down (not that this ever lasts past date number three), and he hasn’t played the amateur vinologist, or done any of the other myriad boring things middle-aged men think will impress a woman their own age.

But in all honesty, there is one thing different about this date. And that’s the fact that they were high school sweethearts twenty-five years before.

“Do you like my hair?” She asks him, causing him to nearly choke on his food. Her new bob, fresh from the hair stylist, falls to her cheekbones, but is dominated by the undercut

“I think you know I do.” Jason answers, an amused smile creeping onto his face.

“Would I?” She answers, fluttering her eyelashes in mock innocence.

“Your hair was still long on your Facebook profile.” he says, with a certain amount of defensiveness. “I would’ve been happy to meet you whatever the state of it.”

Of course he’s reminded of the fight they had a quarter of a century ago. The reason they broke up.

“But your appetites haven’t changed?” Crystal insists, unable to resist teasing him.

Jason sits back, extending his gut. “I think my waistline disagrees.”

“I like the beard, I like the belly. I’ve never been a skinny girl myself, and I’m done dating guys who are smaller than me.” she says, reassuringly. “But, I’m talking about your tastes in hair.”

“They haven’t changed.” Jason states, clearly flustered.

“For what it’s worth, it was wrong and immature of me to react the way I did.” Crystal says. “I was young. I’ve let men off the hook for worse. Much worse.”

“And I shouldn’t have pushed my kink onto you that way.” Jason apologizes in turn. “You must’ve felt like I was taking advantage of you.”

“You didn’t push. Not the way I remember it. You just asked.”

The awkward silence is almost unavoidable, but Crystal has a plan for tonight. She hunches over, and says in a conspiratorial tone “So, did you ever get to do it?”

“Do what?” Jason is as stubborn as she remembers him.

“You know – shave a girl’s head?”

“No. You’ll be happy to know that I dated a girl with long hair for five years afterwards.”

“Lisa? I think I remember her.” Of course she remembers. The confusion and envy of seeing the guy she dumped with another woman. The gut-wrenching finality of it.

“Yep. She never wore it above her shoulders in all the time we were together. Nor the girl after Lisa, nor the girl after that girl. I guess I had to prove something to myself.”

“Aw, poor you. The sacrifices you’ve made.” her eye roll doesn’t impress him.

“But you’ve been living the bachelor life for the past five years. No cute short-haired things you’ve been able to lure to your bedroom?”

“Not one of them as cute as you – or as short-haired” he tries to flatter her.

“But, I bet you’ve got a pretty sweet bachelor pad, right? Single guy, 45, good job, no kids?”

“That I do.”

“Wanna show it to me?”

It doesn’t take him long to ask for the check.

They spend a lot of time inspecting each other’s naked bodies, so familiar yet so different. His chest more broad and hirsute, her boobs now heavy and pendulous.

“What, you’ve never seen a girl with ink before?”

“Not as much as this. Does it run all the way over your back?”

She turns around to show him. “When you’ve got a lot of skin, why not use it for art?” she giggles.

“You hide it well. I had no idea in the restaurant. Well — I knew you were a work of art, of course.”

“Until now, it’s only skin I can cover up with clothes. I really want to get my forearms and chest done, but I keep chickening out.”

“I never figured you for the type.”

“I’m not the same person as the girl who left you. More ink, more butt, more belly, more boobs, more chins. And a lot more confidence.”

That’s his cue to run his hands over her hips.

“I’m the kind of guy who likes it when there’s more of everything. Well, I like that there’s less of this.” His fingers are running up her shaved nape like they used to, and suddenly his touch feels intensely familiar.

“Why, that reminds me.” Crystal says. “Your hair is longer than mine. We need to fix that, stat.”

Of course, Jason has clippers in his bathroom. Big, chrome-plated things that seem more at home in a 1950s Cadillac dealership.

“What do you use to trim your beard?” She presses him.

Sheepishly, he produces much more usable, cordless ones.

“How short are we talking about?” He asks.

“Don’t you worry about that. Get on your knees, and concern yourself with this.” she says, holding out one of her barbell-ed nipples, its areola the center of an inked mandala.

He needs to use both his hands to cup one of her breasts, but the touch of his lips is delicious.

“Go gently.” she says, as the clippers start humming.

Crystal doesn’t remember that much about her teenage sexual fantasies before meeting Jason. Brief, mostly romantic affairs, informed by a clinical sex ed book and the occasional glimpse she had of a porn magazine.

But in the months after their breakup, the gut-wrenching time when she missed the touches and smells and rawness of the real thing, she developed complicated narratives about their reconciliation. One involved him submitting to the same humiliation he’d proposed for her, shaving his head to prove his love.

What she’s doing now, peeling the hair off his head like an orange, she’s done a hundred times before while masturbating. And at least five times with other men, whenever they needed her to forgive some misstep. She’s found she rather likes shaved heads on men.

Already, her hands fold one of his ears forward to allow the unguarded clippers to get at every last bit of Jason’s pepper-and-salt hair. And then it’s done, his bushy sideburns contrasting sharply with the bare skin above.

“Hmm, let me see you.” she says, plucking him off her breast. “Much, much better now.”

“I’ve had it buzzed to a #2 before.” he says, looking at his own reflection in the mirror. “But this is to the skin.  I feel very naked.”

“In case you haven’t noticed, I like you naked.” she answers, stroking his erect cock. “Now show me this bed of yours.”

It’s only a matter of time before she has him lying on his back, his cock curiously familiar after twenty-five years before she takes it in her mouth. His hand is already exploring the shaved nape of her bob.

“Do you like the feeling of it?” she asks as she pauses for a second.

“All of it.” he laughs.

There was another frequent sexual fantasy she developed after she broke up with Jason. One where she imagined apologizing to him, willing to do whatever it takes to get him back. She had vivid fantasies of her own head being shaved, of becoming his bald play toy, a constantly visible reminder that she was so depraved that she’d happily choose sex over her own dignity.

She’s still holding the hair trimmers in her hand. She pushes them into his.

“Shave me, you bald fuck.” she says.

“Are you sure?” He asks, clearly unable to believe his luck.

She answers by taking his cock back in his mouth, because she isn’t. Or because she is, but she can’t say it out loud.

The cold steel blades of the clippers touches her forehead, and a buzzing sensation starts as her locks start dropping onto his belly. She slows her pace, knowing that he’s not that far removed from exploding in her mouth. She wants him to focus on her head.

Another pass, taking another strip off the top of her head. At least he was smart enough to start there, and not on the sides. There’s no backing out now.

She decides he’s had enough fun, leaving his turgid cock alone, and looks at the bleached-blonde locks on his pelvis and bed sheets.

“Sit up.” She commands, turning around on her back as he does so. “Now take care of my head, while I take care of myself.” Putting her head in her lap, one hand strokes her slippery wet pussy, another softly kneads a breast.

The shaving continues, while Jason moves the clippers over her head with the slowness and intent of a caress. He wants to savor every second of this. That makes two of them.

Finally the buzzing stops. She’s bald. She’s made herself cum to the idea of it for Twenty-five years, but now it’s real.

“You look extremely hot bald.” Jason says, stupidly. “Do you want to see?”

“Shh.” Crystal shushes him. “Get on your back.” Maybe she does look hot. Maybe she looks stupid. But this is the brief period of time when she doesn’t know yet, when there’s no mirror to tell her anything, when the possibility of searing regret and happiness are both equally palpable.

Putting her knees on either side of his face, she pushes her fat pussy onto his chin. “Don’t talk. Eat.”

He does with gusto, and when one of his hands stop cupping her big ass, she knows it’s because he’s enjoying the experience just as much as she is, stroking his cock while he licks and sucks her dripping wet pussy. With both her hands flicking her nipples, she looks down upon his smothered face, seeing nothing but delight in his eyes.

Finally, she allows herself to touch her shaved scalp first with one hand, then running both hands over it, the raspy feeling of stubble against her fingers both familiar and strange. This is her own head, not somebody else’s. She allows herself to imagine what she looks like, knowing the light color of her hair will make her look completely hairless, unbroken pale skin from head to shoulders to toes.

She arches her back, pushing her pussy even further down, one arm supporting her weight, while the other is still on her own head. She’s bald at last. And she knows she’ll enjoy every second of it.

A sudden warm, wet sensation on the back of her head startles her, and when she realizes what it is, it sends her over the edge. She cums with a loud moan while she rubs Jason’s sticky jizz all over her scalp.

For what seems like half an hour, they just lie there, head to toe, Crystal only moving her legs to relax her knees and make sure Jason has space to breathe freely.

She wonders what Jason is thinking. If he’s thinking she’s desperate to get back together, fulfilling his ultimate fantasy to get a ride on his cock. She needs to make him realize that this is now HER fetish, even though she’s happy to let him come along for the ride.

She wonders about the wig she has at home. The cover story she has for her coworkers, about wanting to go back to long hair. Will it be itchy?

But above everything she wonders what she looks like. Slowly, she gets up and makes her way to Jason’s bathroom.

She’s used apps that use AI magic to make her look bald. She’s asked seedy men on the internet to doctor her pictures so that she could see what she’d look like bald. None of it has prepared her for the real thing. Seeing the outline of her own skull, turning around to see it from all angles. Powdery blonde-gray stubble reflecting the light, giving only the barest hint of where her hair line used to be.

There’s another possible scenario. She could show up at work bald. Endure the cross-examination of her friends and coworkers. Gradually inhabit her new identity as a fat, bald, tattooed woman. And never worry about growing it out, or the wig slipping. The more she looks at herself in the mirror, the more she likes that idea.


All images accompanying this story were generated by AI. Any resemblance to real persons, living or deceased, is unintentional.

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