I first met Jessie at a work party. She was a spry young thing, clearly very excited to be there, feeling like a real adult, enjoying the free champagne. I soon found out that she was the daughter of one of my colleagues, a man who worked for a different department in the company. I couldn’t take my eyes off her all night, fixated on her long legs, the way her body filled out her short little black dress, and, most of all, her head of lush blonde waves.
For days after the party, I couldn’t stop thinking about Jessie. What incredible hair that girl had! I wasn’t sure when I’d get to see her again, when, just my luck, some internship positions opened in my department. It was my duty to welcome the fresh recruits and show them the ropes.
A couple young men filed into the company’s front room, and then, I heard the click of high heels coming down the hall. I resisted the urge to grin as she stepped in, looking so smart and put-together in her tailored little skirt and blazer. Her hair was neatly pinned up in a large bun at the back of her head. While I showed the interns around and welcomed them to the company, I kept stealing glances at Jessie from behind. Her hair was so thick, and it shone wonderfully, even in the room’s fluorescent lighting.
We started to interact more often as her internship progressed. The job didn’t exactly come naturally to Jessie, but she was eager to learn, so she came to me often with questions. Eventually, I decided I could invite her to see me outside of work hours without it seeming strange or creepy. Sure, I’d been unable to stop thinking about that pretty blonde head for months, but I didn’t want to make the girl uncomfortable.
We had a few drinks at a bar near the office and talked for a while. I was going to order a cab home when she hit me with her first surprise of the night, not to be the last.
“Why don’t you take me home?” She looked up at me with big brown eyes, tugging at the hem of the tiny little dress she’d changed into for the evening.
“Are you sure, Jessie? I’ll pay for the cab.” Still, she insisted, and who was I to pass up such a pretty girl? It’s not everyday that someone with those looks wants to go home with a middle-aged man like me.
As soon as we were inside my apartment, she shed her jacket and heels. “God, get me out of these clothes!” She beckoned to me, so, naturally, I helped her out of her little dress. Her curves pressed against my hands as I pulled down her tights, then unclipped her bra, taking the opportunity to feel up her generous chest.
“Oh yes! Strip me naked, please!”
Things were getting hot and heavy awfully quickly, but I figured maybe young people did things differently now. Jessie’s panties were wet as I pulled them off, and I was about to slip a finger into her when she batted my hand away.
“You’re not done yet.”
“What do you mean?” I retorted, somewhat confused. “You’re already naked.”
“I need you to take something else off of me.” There was a wild look in Jessie’s brown eyes. “I need to get rid of it.”
“Jessie, what are you talking about?”
“Shave my head.”
“I’ve had long hair all my life, and I’m sick of it. My parents made me keep it long even though I wanted to cut it like a boy’s, but they don’t control me anymore. I need it gone!”
“Can’t– can’t you go to a salon for that?”
Jessie looked at me sidelong. “I thought you’d be more fun. I’ve noticed you staring at my hair, don’t you wanna keep it like a trophy?” I’d never thought of it that way, but she had a point. If I kept Jessie’s hair, I could touch it and enjoy it every day, and she’d have the freedom she so badly wanted.
I decided to play up a bit of an act; Jessie seemed like the type who’d enjoy it. “Alright then, on your knees, Missy. And stay here.” I could hear her assuming the position as I headed to the bathroom to get my clippers, as well as my razor and shaving cream.
When I got back, I pressed Jessie’s face against my crotch, letting her feel how I was getting hard. I also made her kiss the clippers before I turned them on, which she did eagerly.
Her hair was satin-smooth and perfectly soft as I gathered it all in one fist, the other hand lowering the roaring clippers toward Jessie’s forehead. She winced as I severed the first section of hair from her scalp, but said nothing. I started running the clippers over the crown of her head, then down to the sides and back, her long, gorgeous locks coming free in my hand. A few strands fell onto Jessie’s shoulders, but she brushed them aside, onto the floor.
Soon, I had a fistful of blonde strands, and a quivering, shear-headed girl practically between my legs. Setting the hair down on the nearest table, I guided Jessie’s hands to her head, running my own fingers over the short, rough stubble that was all that was left of her once-perfect mane. She made a wordless little sound of both pleasure and surprise, looking up at me with her eyes huge.
“We’re not done here.” I gripped her stubbly head in one hand, the other undoing the fly of my pants. My cock sprang out and Jessie stuck out her tongue, coyly licking my tip. “I’ll need more than from you, baldie.” I roughly grabbed her head with both hands and forced her jaw open with one thumb. She moaned in delight as I began to fuck her mouth, not caring that she was drooling everywhere. God, that girl had a tight little throat! It wasn’t long before she was red in the face and I was pulling away, only to unleash my come all over her pale, sheared scalp.
I made her rub the come into her stubble, then guided her to the bathroom so she could see herself in the mirror. It took her a while to say anything, but she finally managed a cry of “Oh, I look good! Really good!”
“You look so much better like this, Jessie.” I rubbed her ass. “But I don’t think we’re done here.”
“No, Sir.” She dropped to her hands and knees and crawled back to where I’d taken her hair, kneeling in a prettily submissive pose. I covered her head in the shaving cream; she was clearly trying to stay still as I began scraping the safety razor over her head, leaving behind strips of pale, perfectly smooth skin, but she was breathing hard and shaking a little.
“Are you alright, Jessie?”
“Yeah…” She took a deep breath. “I’ve just wanted this for ages, and it’s finally happening!”
“Oh, it’s happening.” I tilted her head so I could shave behind her ear. “You’re gonna be bald, the world will know you’re a cueball, you’re gonna be so smooth and hairless…” She seemed to like me talking like that, moaning prettily. When I was done removing her hair, I rubbed some aftershave into her scalp. She winced at my hands worked over her newly smooth skin, thumbs tucking behind her ears, getting the stinging, manly-smelling liquid everywhere.
Jessie was a bit red in the face, but she couldn’t wipe away her grin. Between that and the telltale wet patch she’d leaked onto my floor, I could tell she’d loved being shaved smooth. I offered her up my shower to clean off any remaining stubble and cream, and she told me to undress and that she’d meet me in the bedroom.
“Now you can tell everyone you’ve been with a bald girl.” She winked.
“If you’ve still got eyebrows, are you really bald?” I retorted, playfully brandishing the razor. It was obvious, I was in for one hell of a night.