A New Haircut

When I was younger, I hadn’t had a haircut in a while, and my hair had gotten a bit out of control–it was now past my shoulders–and I wanted it cut. I didn't want it cut too short, because I was so used to having long hair.

One day, my sister’s gay friend, Wyatt, came to the house and stayed with us. Keep in mind that at the time, Wyatt was a year older than me and I had a crush on him, and my sister knew that (apparently) and would purposefully invite him to make me flustered.

My sister told him that I wanted a new haircut, and he offered to cut it. So, me and Wyatt went into the bathroom together, and he immediately began to cut my hair. As he was cutting it, I could only focus on his hand in my hair and his breath on my neck, which kept making me blush and feel awkward. He was surprisingly gentle and precise with each snip. He kept talking to me and telling me jokes, which helped to make the time pass more quickly.

At a certain point, I noticed that he was getting pretty close to my ear as he spoke, and was smiling every time I shivered, and I felt my face heating up more and more. 

Then, after what felt like hours (but was probably only a few minutes), Wyatt asked me: “are you gay?”

That made me blush even more, and I shook my head and said, in a very awkward voice, “of course not!”

Wyatt then looked down at my lap, and then back up at me, which made my heart jump. I was hard, and Wyatt had noticed.

“Really? Because…” Wyatt cut himself off, smiling as I ducked my head down, hiding my blush.

I couldn’t help but look away, feeling my cheeks flush even more. I felt my heart racing, and I knew he could see it. He slowly reached out and brushed his fingers against my palm, sending shivers down my spine. I looked back up at him, my eyes wide with surprise. He smiled softly and said, “It’s ok if you have feelings for me, too.”

I quickly looked away once again, feeling myself get harder. Wyatt chuckled, and then gently put his hand on my thigh. His fingers were warm and his touch felt electric.

“What are you doing?” I asked, my voice barely above a whisper.

“Nothing,” he replied. His eyes were focused on mine and I could feel myself melting into him. I looked down and then back up, feeling my heart beat faster.

I knew he could see my heart racing, and I nervously looked away again. I felt his fingers intertwined with mine and I looked back up at him, my cheeks flushing even more. He smiled softly and said, “It’s ok if you want to kiss me.”

I felt my heart flutter as I looked into his eyes. I was so drawn to him, like I was being pulled in by an invisible force. His gaze was intense, and I found myself unable to look away. I felt my breath hitch as he slowly leaned in, bringing his face closer to mine. His lips were so close that I could feel his breath on my skin. I closed my eyes as he pressed his lips against mine, and suddenly I was lost in a cloud of emotion.

“Hey–” I started to say, but I could feel myself losing control as he pushed his hand under my shirt, pulling it up. I felt his fingers on my skin, and then he slowly pushed his palm up my stomach, over my chest, and then down my side. I shivered as his fingers traced my side, and then suddenly my shirt was gone.

I felt myself getting harder, and I knew that he saw it twitch, and then he gently put his hand on my bulge, rubbing it with his thumb. I felt my heart beating faster as if I was about to have a heart attack, and I tried to relax, but I couldn’t stop my hands from shaking as he touched me.

I was inexperienced, and this was my first time, so i felt nervous and excited at the same time (I had never even jerked off at the time, and I really had only got boners, and never thought to touch it).

Wyatt quickly pulled off my pants, taking my underwear with it, and immediately got to stroking. I kept my lips shut tight, doing anything to stop myself from making an embarrassing noise, and tried to stay still, which barely worked. The more he stroked me the more I let out gasps and soft moans that made me cover my mouth and close my eyes.

By the time my eyes opened again, Wyatt’s other hand was around his cock, and now he was in front of me, stroking us both.

His dick was short, and thick, and flushed ruby pink. I wanted to touch it and see what happened, but before I could Wyatt was moving again. When he leaned in close, the smell of him was overwhelming, filling my lungs and forcing me to groan to make room for it in my chest. Wyatt lined us up, tip to tip, and the touch against such tender flesh made my nerves twitch in anticipation. It got better when his warm fingers clasp around us, and Wyatt made his first, tentative, stroke.

Wyatt moaned quietly as he pleasured us both. It felt incredible, aided by the slip of precum spilling freely over Wyatt’s knuckles, the sensation of it consuming me, clogging the gaps in my brain. I felt like I had slid into some narcotic delirium, but it was heaven and I wanted to stay there forever.

I had no thoughts but sweat glossed skin and every needy inch of my shaft being stimulated by the press of a slippery hand.

I buried my face in the side of Wyatt’s neck, where his muscles stand out clear and ropey. The pressure behind my balls reached a terminal point, and I probably wouldn't have been able to hold on much longer even if Wyatt didn't make a sound so fucking sexy my restraint crumbles, completely.

I collapsed like a bridge with the struts blown out, release surging through me in deep, throbbing pulses, and soon Wyatt teeters into climax too. His hips jerked, an involuntary gasp, and I was still thrusting into his fist with no purpose beyond the instinct of an animal. My body felt wonderful. My mind was calm. Wyatt’s weight on my chest was heavenly, tangible deep down in my core.

Or at least, it was until Wyatt propped himself up, and pushed my limp and sweaty bangs back off my face. He cocked his head and touched my lashes with the pad of his thumb.

“Good job,” he murmured, like it was a compliment. For some reason hearing it from Wyatt felt alright, because he wasn’t saying it sarcastically.

“Thanks,” I replied, panting softly.

Soon after, Wyatt left, and every time I saw him in school I would blush, getting reminded of that day over and over again.