The Haircut Story Site

SIR, YES SIR! -2- Scotty's Dream by Clipperaddict

This is the second in a series of stories. To get more context, I recommend reading SIR, YES SIR -1 �" Alec’s Dream first.

It’s been 12 weeks since Alec arrived on base, and I first sat in his chair with my shaved head. I’m Scotty, currently serving in the USMC. It’s been 8 years now serving as a drill sergeant, with just under two years until I retire with 20 years of service. Alec is a youngish guy (28, I discovered) working as a barber at the base barbershop. He is 5'10" with a mop of curly hair, a goatee, and a mustache. Alec’s dream is to keep a US Marine Drill Sergeant squared away with a radical shaved high and tight horseshoe flat. He asked me to grow out my hair on the top of my head so he can fulfill his dream, and as he puts it, "Perform his patriotic duty". He has dutifully been shaving my whitewalls every 3 or 4 days since we met. The top has been trimmed ever so slightly just to keep it looking sharp. Over the past 12 weeks, we’ve become fast friends. There’s no doubt there is some significant chemistry between us, and so far, I’ve gently resisted his overtures to be more than just friends. I won’t pretend it has been easy, but I’m not out and have never been in a romantic relationship with another guy.

Alec turns me back to the mirror to inspect his latest masterpiece. He fixes his gaze on me in the mirror and tells me it’s time. I blush as I’m not exactly sure what he means. I shuffle nervously in the chair as he declares that the next time I sit in his chair, he will be carving the most badass, radical, shaved high and tight horseshoe flat top ever. I let out a deep breath, somewhat relieved as he bends over and whispers in my ear that it won’t be happening here in the base barber shop. I turn my head to look directly at him and ask what he means. He leans in and grabs my face with both hands and tells me it’s time for me to visit his private home barber shop. Then, without warning, he pulls my face towards him and kisses me, forcing my lips open with his tongue, making out for a good ten seconds. Part of me wants to push him away, and the other part of me doesn’t want it to stop. The other part wins as I give in to his amorous advance, and my tense shoulders relax. He slowly lets go and steps back, looking at me anxiously for my reaction. I’m still a bit stunned, so he asks if I’m OK. It takes me a bit to respond that I think so, but I’m not sure. For the first time, I saw his confidence crack just a bit. As he starts to apologize, I stop him and assure him that I am OK and just need a minute.

Alec is still a little flustered and pretends to be busy folding the cape and disposing of the straight razor blade. For most of my adult life, I’ve done a really good job of managing to keep my emotions in check and not allow myself to give in to feelings I’ve had for attractive men. I stand up out of the chair and turn Alec towards me. He’s trying to avoid eye contact, so I grab his face with both hands and tell him I’m sorr,y and can’t find the words to explain, so I simply lean in and kiss him deeply. We both succumb to the moment. After coming up for air, I told him I wanted to sit in his private barber shop chair and have him carve the ultimate shaved radical high and tight horseshoe flat. Before I do, though, there are some things he needs to know about me. I am off duty the next day, and he is only working until noon, so I suggest I pick him up, and we can take a drive to the beach so we can talk.

After a restless night, I get myself ready for our "date". I selected one of my brilliant white, thick cotton T-shirts and a pair of khaki cargo pants. I arrive right on time, and Alec gets into the car. The conversation is light and slightly awkward as we head to the beach. I have a favorite spot with a rocky peninsula that juts out 20 yards off the pristine golden sand. We walk for a bit, and then I lead us over to the rocks so we can sit and enjoy the waves crashing. Before I get a chance to say anything, Alec blurts out that it doesn’t matter what I need to tell him. It won’t change how he feels about me. I appreciate him saying that and tell him I hope that is the case, but I won’t hold it against him if he changes his mind.

I take a deep breath, clear my throat, and begin by telling him that yesterday was the first time I had kissed a man. I assumed he knew that I wasn’t out, but what he didn't know was that I wasn’t even really out to myself. Meeting Alec and flirting with him is the first time I’d allowed myself to acknowledge that I am a gay man, and honestly, I’m scared s**tless. Alec is taking it all in. His eyes grew wider as I shared my deepest secret. He stutters as it dawns on him that most of the assumptions he had been making about me, my sexuality and experience were completely off. He just said, "WOW! WOW! WOW! You mean you’re a virgin?" His shocked expression is comical, and I can’t help laughing as I confirm that I am a forty-year-old virgin. "OH MAN!" he says, "You know that makes you even hotter to me? I feel like I need to help you. Assuming, of course, that’s what you want?" Therein lies my dilemma.

Meeting Alec has turned my world upside down. My plan was to continue to put any kind of romance off until I retired in a couple of years, when I hoped to find a submissive mate of similar age, nowhere near a military base, but rocking a military haircut. Here I was falling for a guy who was nothing like what I had imagined. He’s a much younger guy, not similar age. He works beside me, and I’ve never approved of workplace romances. He’s sporting a mop of curls, which I find strangely attractive (although I wouldn’t mind seeing him in a military cut). I’m enjoying being dominated by him, having always wanted to be in charge. It had all come to a head yesterday when Alec kissed me. I felt completely out of control and a range of contrasting emotions, arousal, lust, passion, along with guilt and confusion. "You’re right, Sarge, that’s a lot," Alec said, putting his arm around me. His piercing blue eyes filled with compassion as he asked, "What do you want to do? ". In that moment, it all became clear, and I pulled him towards me, pausing just for a moment before our lips locked. His hands were rubbing my smooth whitewalls as my hands got lost in his curly mop.

After coming up for air, Alec looked at me tenderly and told me he was incredibly honored by my trusting him with my story. In a serious tone, he told me that he still wants our relationship to go deeper and more intimate. Given my complete lack of experience, he wants to lead me in trying new things. He would tell me first and wait for my response of "SIR, YES SIR" before proceeding, giving me an out if I wasn’t ready. Lightening the mood, he asked if I would like to feel his rock-hard erection? It was tempting to keep him waiting, but I didn’t, telling him "SIR, YES SIR". He took my hand and placed it on the crotch of his jeans before unbuttoning them and taking my hand and placing it directly on his cock. I must admit it was just a tad embarrassing for me, but not at all for him. "Recruit, I am about to stroke your hard dick!" he announced. "SIR, YES SIR". A line had been crossed, and it was so much better than I had ever imagined it would be.
Heading in the car to Alec’s place for my haircut, he had a ton of questions. He wanted to know how I satisfied myself and was in disbelief when I told him I’ve never risked online porn or any form of social media, as I didn’t want to jeopardize my career. My only source of relief was an obsession with haircut stories.

As we got closer to his place, the mood turned serious again as Alec told me he’d better warn me of a few things before we got there. "Unlike you, I have a significant online presence. Nothing sexual, but a large following on TikTok and Instagram with videos of major haircut transformations. Guys come from near and far for their Alec the Barber makeover. Even when he moved across the country to take his dream job as a USMC barber, guys continued to come to him. With only working 3 days a week on base, he had plenty of time to fit in appointments. I was stunned. He thought he'd better tell me, as I’d likely wonder how he could afford such a nice place on a part-time military barber salary. Apparently, his online business was very lucrative. He also wanted to explain why his home barber shop is set up with cameras, lights, and editing equipment. He was quick to assure me that he wasn’t planning on recording my haircut, especially as he hoped it would be an intimate experience.

We pulled up to this beautiful craftsman bungalow in a plush neighborhood. The detached garage to the side had a barber pole attached above the doors. Inside was the classic traditional barber shop setup. An antique Koken chair with red leather, white porcelain, and gleaming chrome was in the center of the black and white tiled floor. A white porcelain hair wash sink and chair sat to the side of a custom-built mahogany barber console fitted with an enormous mirror and all his pristine barber tools and equipment neatly laid out. Opposite the console, a row of red stadium seats for waiting clients and companions. In the corner, there is a custom mahogany bar with a selection of fine liquor, a beer tap, and wine. Alec offered me one of his specialty old-fashioned cocktails as he invited me to take a seat in THE chair.

The delicious drink went over easily. Alec approached, asking if he could help me get a bit more comfortable by removing some of my clothes. "SIR, YES SIR!". Between kisses, he removed my t-shirt, cargo pants, socks, and shoes. Sitting in my underwear (white cotton boxer briefs), he asked, "Are you good with no cape recruit?". "SIR, YES SIR!".

It was 4 days since my whitewalls were last shaved and 6 weeks since the top had last been cut. He began with the Osters 76 00000 straight back from my right temple. The second path from the left temple met at the back, forming a wide bald ring. The rest of my hair below the ring was quickly removed with it falling on my shoulders, down my chest, and some resting on my bulging underwear. The top hair was sprayed, ready for the hairdryer and stiff brush, firmly making every single hair on top stand erect. As Alec leaned in with the Osters and a vertical fine-toothed comb to run around my head, he pressed his hard cock into my shoulder. He, too, was stripped to his underwear (a skimpy, almost thong-like pair of black briefs). Each pass of the clippers over comb was precise, over and over again. I was struggling to stay still as my dick was ready to burst out of my briefs. "Take it out if you want, recruit.", Alec said. "SIR, YES SIR!" I replied as I opened the fly and out it popped. For the first time, I noticed Alec lost his cool just a bit as he stared at my member. "Oh my, that’s impressive," he muttered quietly before regaining his composure and standing to the side as he readied to flatten the top freehand. He was bold with the first pass down the middle, with the Osters almost touching down on my scalp. Passes to both sides saw half-inch locks falling in my lap. His concentration was 100% as he leaned in close to check his work, tilting his head to double-check in the mirror behind. It was at least 15 minutes with only the hum of the Osters. Neither of us said a word. The second and third rounds of passes over the top did touch down, and without being able to see, I could easily imagine a wide landing strip being carved.

After all the clipper work, Alec set about prepping the hot towels and lather. He used a Proraso shaving crème mixed in a shaving mug and applied with a badger hair shaving brush. Another first-time experience that was most enjoyable. The towels (yes, he uses two) were at the hottest possible temperature without scalding. As he wrapped them around my face, they captured the sandalwood aroma of the shaving crème. It was heavenly. While the hot towels did their work, Alec told me he was going to help me out with my impressive manhood. "SIR, YES SIR!". On a day that I didn’t think could get any better, he knelt in front of the chair and took my member into his mouth. I can’t describe the amazing sensation. All my adult life, I had dreamed of this happening, but nothing came close to the actual experience. I still don’t know how I managed not to cum immediately, and just when I was about to, Alec stopped to remove the towels and begin the first shave of my whitewalls. His tool of choice was a finely honed antique straight razor. His technique was masterful. Stretching the skin with his thumb and shaving the tiny bristles with short, precise strokes. A quick check for smoothness before moving on to the next area is repeated. For the first time, I wished I could face the mirror to admire this master craftsman at work. The whitewalls were followed by the landing strip. I had to take shallow breaths to avoid shooting a load. I’d been shaving my head for 10+ years before I met Alec, so this wasn’t new to me, and yet it seemed it was. Round 2 was a repeat of Round 1. Instead of Alec pleasuring me, he asked me to stroke his dick while the hot towels did their work. "SIR, YES SIR". I guess I did a great job, as he had to tell me to stop as he was about to blow and didn’t want to yet.

The shave completed, he grabbed his shears to make a few fine-tuned adjustments before making the grand gesture of turning me around to face the mirror. I was in awe as I studied the master’s workmanship. The high and tight horseshoe flat top with shaved whitewalls and landing strip has always been my dream haircut. This wasn’t my first, but it was the best I’d ever had. My dream had come true.
(TO BE CONTINUED.)

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