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David & Nate by Oliver

My name is David and I'm a junior in high school in a small town in Texas. I'm average height and average build with sandy blonde hair and thick-rimmed glasses. I'm definitely attractive, and my family always used to ask me why I didn't have a girlfriend. Well the answer is quite simple; you see, I'm was never exactly attracted to women. In fact, I had my sights set on one guy for quite a while. His name was Nate.
Nate was a very popular guy at school, being on both the football team and school debate club. He was tall and very well built with a thick neck and medium to short chocolate brown hair. His hair was cut off the ears every once and a while and never reached his collar. Nate and I were lab partners and eventually became close friends. It wasn't hard to tell that the two of us always had a flirty undertone to our relationship.
So one day I invited Nate over to study with me. I cleaned my room and went into the bathroom to make sure everything was neat and tidy. While I was there, I took a look in the mirror. My sandy blonde hair definitely wasn't long, but it wasn't buzzed or anything. I had always fantasizes about getting a shorter haircut than this, but I never had the courage. It's not like short hair was unheard of in my town or anything. Some JROTC kids had buzzcuts. My cousins all went to a private school in town where boys were required to keep their hair under an inch in length. One teacher, Mr. Johnson, even gave extra credit to any kids who went out and got flattops like his. Even though I had such a fascination and attraction to short haircuts, I never could work up the courage to cut my hair shorter.
I hear a knock at the door and run downstairs to open it. There's Nate, handsome as ever, wearing a tight tee shirt that showed off his muscles very nicely.
"Hey there, stud." he said with a smirk.
I immediately took notice that his hair was shorter than usual. Nothing super drastic, but definitely shorter than usual. The sides would be too short to grab if you tried. It wasn't so short that the scalp was visible (though you could almost see some skin at the nape area.) Clippers were definitely used on the sides and likely even up to the crown, but nothing shorter than a #4. The top, which had been noticeably thinned out, was about 2 inches long and styled upwards and over to the side with product. I always loved when guys got haircuts slightly shorter than usual like this.
"Hey did you get a haircut?" I commented
"Yeah I just got it right before I came here. It's a little shorter than usual haha." He blushed a little. I could tell he was afraid i didn't like it.
"It looks really great. I really like this shorter length on you," I added. "Are you gonna keep it this length?"
"Thanks!" he chuckled bashfully and felt the buzzed hair at his nape. "I went to the barber with the intent of getting a new hairstyle to keep. To be honest, though, the barber left it longer than I wanted."
"Oh really?" What he said had really excited me. "How much shorter did you want it?"
"Well I kinda wanted it done with electric clippers all around my head. Like one of those JROTC kids." he said shyly. "I mean he used clippers on the sides and even some towards the top around the crown, but I wanted to try something super short."
I was still extremely aroused by the idea of Nate getting a short haircut. It would look so hot with his thick neck and athletic build.
"You'd look great with a cut like that. I tell you what, let's ditch the studying and go get you a haircut." I told Nate, who clearly felt the same way about the idea as I did.
"Alright, but while we're at it, you should get a haircut too." Nate said, tousling my hair in a playfully flirty manner. I couldn't help but smile a big, toothy grin.
"I'll take that cute little smile as a yes."
I couldn't stop thinking about this haircut I was gonna get. I'm pretty scared to try anything too drastic like a flattop or a high and tight, but I have always wanted something like that.
We find a barbershop that we're sure will give haircuts to the shortness we desire. We walk in and a waft a clean-smelling air blasts us immediately. Only one barber is on duty, and that's a fairly handsome 40 year old man with a ginger side part shaved down to the skin at the sides. A man in one of the chairs waiting to get cut has an incredibly short high and tight buzzcut; can you imagine having hair so short that when it exceeds 1/4", you go for another cut? In the chair is a very timid-seeming, handsome-faced teenager about my age who is strapped into an unfortunate big complex headgear braces contraption and being shorn to a very short flattop. He looks very embarrassed and his pale scalp shows that this is his first haircut this short in... well... ever. I know exactly what's happening to him. You see, in my town, there is on especially mean dentist named Dr. Higgins. All his victims end up getting fitted in headgear, which they are expected to wear 24/7. Most of these kids, whose popularity is already out the window, get their hair cut especially short to prevent discomfort with the headgear straps. I can't begin to imagine the embarrassment they feel. Once he's finished up, the boy gets up and walks to the door l and I recognize him as Gage, a boy I know on the soccer team. He must have gotten the Higgins treatment on Friday, because last time I saw him at school, he was not wearing that torture device.
"Hey, Gage." I say. He seems completely mortified.
"Hey, guyth." He says as he bows his head and rubs his newly shorn flattop. He speaks with a heavy lisp through all the wires.
"Higgins?" Nate asks.
"Yeah. That guy thuckth. He thayth I can't take thith thing off. I came here to get a haircut to make the thtrap hurt leth."
"The cut looks good on you though if it's any consolation." Nate says.
"Thankth. Well, I'm off. Thee ya." Gage attempts the best smile he can and walks out, now palming the bristly flat part on top of his head.
"Next" says the barber.
I go up there and get my new style: a trendy undercut. The sides are buzzed to a number 2 and the top is styled in a part. Nate comes up and rubs the sides of my head.
"Is that the shortest you're gonna go? Oh well, it still makes you look even more attractive than before." He says flirting as he takes my place in the seat. Nate's next words truly shock me.
"I'll have what the kid with the braces got."
"One short flattop crewcut coming right up." said the barber.
The clippers roared to life and the barber started with a #2 all around the head except near the front. A grin spread across Nate's handsome face. I could tell he loved having his hair stripped away. The clippers started around the ears, freeing Nate's skin and allowing it to breathe. The clippers then tore up the nape, which was the shortest part of Nate's most recent haircut before this; though the new short length made that part look long. The other side was then clipped the same length. The most surprising part came when the clippers were passed across the top of the head and the crown area. Nate had a #2 buzzcut everywhere but in the front section of his hair.
Next, the barber switched the blades and began to taper the sides of the haircut to a low fade around the ears and the nape. Now for the best part, the remaining part of Nate's hair was cut down to an inch and styled upwards where it was leveled as the barber made slight adjustments from each side.
What Nate was left with was a sexy and very short cross between a flattop and a crewcut, and boy was I turned on. On the ride home, I rubbed Nate's short hair and we talked on and on about how good it looked and how he's gonna keep it that way.
We got back to my house and went up to my room and sat down on my bed. When suddenly, Nate leans in and locks lips with mine. We continue to kiss as he pushes me down against the bed. The short buzzed hairs on the back of my head feel incredible against my pillow. I reach up and feel his hair and he purrs in delight.
"Now for something i've been waiting far too long to do." Nate says as he reaches his hands into my pants and well... you know the rest. Needless to say, that's how Nate became my boyfriend.

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