My boyfriend Chase and I have been dating for about two years, and early on into our relationship we revealed to one another that we both liked bedroom time on the rough side. Because of this, we’d come up with a code word if anything ever got too aggressive, and it was “Oklahoma”. It all started after Chase teased me for miss-hearing Peyton Manning’s play call as Oklahoma instead of Omaha, and it just kind of went from there.
Now, I absolutely love Chase, and I am fairly certain he will propose soon, but there is one thing about him that absolutely drives me nuts, and not in a sexy way. It’s his hair. It hangs in his face constantly, and he hides behind it like a little kid. It’s usually greasy, it’s so long it has no volume so it just hangs limply from his head, and it’s resulted in a few people cat-calling him thinking he was a lady with his long blond tresses. When we first met it was shaggy and curled over his collar, and I always figured he was just growing it out because it was winter. I was wrong. I don’t think he’s gotten an actual haircut since we met, and now it’s about mid back. I mentioned cutting it once, trying to be casual about it, and he turned beet red and just told me “I like it long”. He wouldn’t let me grab onto it during sex for a week, like he was afraid I was going to rip it from his head. So, I never mentioned it again, since I really hadn’t meant to upset him.
The thing was, I was beginning to doubt I could stand looking at it any longer. And the thought of walking down the aisle and seeing him standing there like a muppet was just really making me question if I did want to take the next step with him. I ran my dilemma by my good friend Breeanne and she suggested something I hadn’t thought of. See, she knows we like it on the rough side. She also knows we’re into roleplay. Breeanne one of the few friends I can be totally open with about that sort of stuff. She’s also a salon owner, and she’s always hated Chase’s hair.
“He likes it when you play headmistress, right? Why not tell him he’s got to get a proper haircut like a good school boy? I can lend you a set of shears and clippers, and you can have your way with him!”
“That could be fun,” I mused, “I’d have to start off slow, give him a chance to tap out, and then I could be as ruthless as I wanted…”
Breeanne nodded enthusiastically, “Drop by tomorrow and pick up the supplies from my shop. And promise me you’ll go on a double date with me and James after you’ve sheared him? I can’t wait to see the final results.”
I picked up the shears and clippers from Breeanne on Friday night and stowed them away in the dresser in our spare bedroom. My plan was to get Chase hot and bothered over dinner Saturday night and then let the game commence afterwards. I fixed his favorite meal, fettuccini carbonara, and poured us hefty glasses of wine. I knew that would set the mood off to a good start.
“I was thinking, you’d look cute in your school uniform, sitting there eating like a good boy eating your dinner.”
This earned me a big grin, “Will Headmistress Lucy be visiting tonight?”
I nodded, “Oh yes, she’s heard you’ve been a very naughty boy.”
His face went pink, “I haven’t, honest, I’ve been good.”
“Well finish your dinner,” I commanded, “And maybe you can have dessert.”
He nodded vigorously and polished off the rest of his plate and his wine. “May I be excused?”
“Yes, you may. Now go to your room and wait for Headmistress to come give you your weekly evaluation.”
He scampered off, and I set the dishes in the sink, giving him some time to slip his school uniform on. Then I went and put on my black pencil skirt and blouse, and got the hair supplies out of their hiding spot.
I walked into the bedroom and he was obediently sitting on the edge of the bed, not making eye contact. I placed the clippers and shears on the nightstand and tutted at him, “Chase, I hear you’ve been a naughty boy this week.”
He continued looking at the floor, “I swear, I haven’t Headmistress Lucy. I’ve been good.”
“Don’t you lie to me,” I barked, “You’ve got numerous dress code violations this week, what do you have to say about that?”
His head bobbed up and he met my eyes, “I-I-I’m sorry, Headmistress, it won’t happen again.”
“You’re right, it won’t,” I cupped his chin in one hand and squeezed it roughly, then raked his hair away from his face with the other, “I’ll see to it that you won’t have any more violations for quite some time.”
His eyes went a bit wide, questioning, but I could also see his manhood was swelling slightly in his trousers. This wasn’t our normal playbook, but he seemed to be enjoying it.
I pulled out the desk chair and dragged him over to it by his hair, “You sit here and be quiet.”
He nodded meekly. I grabbed the scissors off the nightstand and stood behind him, running my fingers through his hair, tutting at him again, “I’ve let you get away with this for too long, Chase. You know school policy, boys are to be clean cut. Look at this mop you have, disgraceful.”
His shoulders tensed, but he stayed silent.
I wrapped my hand around his hair and held it firmly so it formed a messy ponytail just below his nape. “Now, if you’re a good boy and let me tidy you up, maybe you won’t be late for your geography lesson.”
This was his out. I bit my tongue, waiting for him to mumble our safe word, but he just silently squirmed in his seat.
I placed the scissors at his nape and started snipping straight across. It didn’t take long before I was holding over a foot of his hair in my hand. I dropped it onto the desk in front of him and he eyed it nervously. I went to his side and grabbed his chin again. His hair now fell in jagged jaw length waves around his face.
“Better,” I mused, “But still work to be done.”
He looked like he was going to cry, but he didn’t utter a word. The bulge in his pants was a tiny bit bigger, I noticed. I dropped his chin and his hair fell forward over his face. I wanted to have a little fun with the shears before I broke out the clippers, so I picked up a chunk of his hair near his ear and severed it, leaving little two inch strands sticking out. I heard him gulp so I swatted him upside the head. Then I went to his other side and repeated the same motion, removing another hefty chunk of hair. I then started taking handfuls at random and slicing them off, dropping them into his lap. My ultimate goal was to reduce him to a nice short buzz, but I wanted him to see some hair raining down when I ran the clippers over his head, so I was careful not to cut any patches too short just yet.
Once there was no hair left longer than two inches all the way around, I stroked the back of his head tenderly, “Oh dear, Chase. Well now you’ve just got a mess, haven’t you? Don’t you worry, I will straighten this right out.”
I glanced over his shoulder, his manhood was throbbing against the fly of his pants.
I retrieved the clippers and plugged them in. Breeanne had suggested a #3 all over to start, then she said to try running a #1 over the back and sides, and finish with a 0 at his nape. I clicked the guard on and placed the clippers right at the center of his hairline. When I flicked them on, Chase jumped at the noise. I half expected him to blurt out Oklahoma! but he just sat there wordlessly.
“What a good boy you are,” I murmured, as I dragged the clippers straight down the middle of his head. I wanted so badly to run my lips over the strip of 3/8th inch fluff they left behind, but I didn’t want to ruin the rapport we had going. Instead I continued making slow even passes over his head, sending thick tufts of blond hair raining down onto the floor and Chase’s lap. Once I was finished I turned the clippers off and brushed my hand over his head, which felt heavenly, and Chase shivered.
“Much better isn’t it?”
“Yes, Headmistress,” he squeaked out. I could see he was still hard, and I made the decision to postpone giving him a proper fade until later. I wanted to stare into his eyes while he begged me to finish him off, which was going to be much easier now that I could actually see his eyes!
“You can stand now,” I commanded, “Turn and face me.”
He stood and looked at me, and I had all I could do not to smile. Just as I knew he would, he looked absolutely decadent without all that stringy hair falling into his face.
“Yes, that should do,” I stated, “Won’t be breaking the dress code for a long while now. Are you ready for your reward, for being such a good boy for me?”
He nodded, flashing me his puppy dog eyes, “Please, Headmistress, I’ve been on my best behavior.”
I pushed him down so he was sitting on the bed, and I was sitting on his lap, then I began unbuttoning his shirt. Once it was unbuttoned I cradled his head in one hand, running my thumb over the hairs at the base of his neck. With my other hand I undid his fly, releasing his manhood.
“Have you been a good little boy and earned your treat?” I cooed, “Tell me how much you want your treat.”
“Please, I want it very badly Headmistress Lucy.”
“Tell me how much you like your new haircut,” I crooned, stroking his member with one hand and the back of his head with the other.
“I love it, Headmistress Lucy.” He let out a soft whine as I tugged on him, “Thank you for making me look like a smart little boy, Headmistress.”
“That’s right,” I whispered in his ear, “My good little boy, my handsome boy.”
He found his release then, and let out a low groan, flopping onto the bed and pulling me down with him. I kept gently stroking his hair as he panted and curled up next to me. Once he’d caught his breath he pulled me in close and kissed me, hard.
“I’ve been waiting for this night,” he breathed, “Surprised it took you this long to go for it.”
I bit his lip and rolled so I was directly facing him. “Had to wait for the right time,” I hummed, “Since, I knew it was going to be a one time deal.”
He gave me a questioning look.
“You know I’m keeping you shorn,” I growled in his ear, “My good, hairless little boy.”
“Yes, Headmistress,” he sighed, kissing me roughly, “Anything you say.”