The Haircut Story Site

"SIR, YES SIR!" - 3 - Scotty Retires. by Clipperaddict

This is the third in a series of stories. To get more context, I recommend reading the previous two SIR, YES SIR stories first.

It’s been almost two years since my life was turned upside down by meeting Alec the barber. I’m Scotty, currently serving in the USMC as a drill instructor. I’m coming up for 20 years and planning to retire. Alec is ten years younger than me, is 5’ 10" with a mop of curly hair, a goatee, and a mustache. He is working his "dream job" part-time at the base barbershop. He also has a significant online presence. Nothing sexual, but a large following on TikTok and Instagram with videos of major haircut transformations, which he does from his perfect home barbershop. We have been dating secretly for 18 months since Alec persuaded me to swap my shaved head for a radical shaved high and tight horseshoe flat. He maintains it for me as part of "His patriotic duty". I had never been in a romantic relationship with anyone before meeting Alec. I had a lot to learn and experience. He has been a great teacher taking things slowly. For each new experience he tells me what he’s planning and only moves forward when I reply "SIR, YES SIR!". It has been amazing for the most part although I know he struggles with my decision to stay closeted until I retire, and, we have yet to fully consummate our relationship.

We have established a twice weekly routine of freshening up my horseshoe flat. Once a week at the base barbershop and more intimate appointments once a week at his home shop. We find other opportunities to be together and enjoy each other in addition to the haircuts.
I try to pick busy times at the base shop so I can see my master barber in action. After a few weeks I noticed that he always gives the guy in his chair a shorter haircut than he asked for. Sometimes it’s radically shorter. So far, he’s gotten away with it. Mostly because he is such an accomplished barber and always gives a cut that the guy rocks. Even his colleague, old Ron, is sporting a bald fade after 40+ years of a tapered short back and sides. Alec has even managed to give him a hard part.
The only guy in the barber shop with long har is Alec himself with his curly mop top. It always looks the same, entrusting its care only to himself. I’ve worked out he gives himself regular tiny trims to keep it the same, never looking freshly cut. Although I don’t like long hair on men, it somehow turns me on with Alec. I love running my hands through it when we’re intimate. I also am not a fan of facial hair, but I find Alec’s trimmed mustache and goatee attractive.

Alec and I are both looking forward to my retirement and we’ve started to make plans. We are both going to go to barber school. I’m going to study for my master barber license, and Alec is going back to become an instructor. Our dream is to open the "SIR, YES SIR! Barber Shop and Barber Academy". More about all of this in the next chapter.

My official retirement ceremony is held on base. It’s very formal and traditional. The base Commander and colleagues I’ve served with give glowing accounts of my service. There is a parade, and presentation of a US flag and a USMC service medal followed by me saying a few words. There is a party in the evening after the ceremony which Alec and I planned.

The day of the ceremony I’m seated in the chair at Alec’s home barber shop. Unusually, we are both clothed as Alec doesn’t want to be distracted from giving me the most meticulous shaved high and tight horseshoe flat. He’s kept me out of the chair for 2 weeks so there would be more than just a millimeter to take care of. Also unusually, I am faced towards the mirror so I can admire his craftsmanship. After 45 minutes, I get out of the chair looking and feeling like I just stepped from a USMC recruitment poster. Alec tells me to check in with him again once I’ve changed into my dress uniform just to make sure everything is perfect. He also tells me to report back after the ceremony to get ready for the party. I had no idea what he had planned but from his boyish grin and the twinkle in his eyes I was certain we would enjoy it. "SIR, YES SIR!".

The ceremony is fantastic. I’m humbled by the kind words and recognition I received. Now I am officially retired it’s time to come out. Alec has been so patient and respectful. I’m not sure that anyone else would have understood and agreed to being in a closeted relationship for that long. As we headed home to get ready for the party we were both excited about revealing our secret. Alec came out in his teens and is openly gay. Everyone just thinks he hasn’t dated in a while. We were intrigued to see if anyone had figured us out.

Back at his house we took off our formal clothes and enjoyed a cocktail in our underwear. Alec disappeared into the large bathroom and called for me. I opened the door to find him naked standing behind a chair with his Osters in his hand. There was a massage table set up against the far wall. He tells me to sit down, and I respond as expected, "SIR, YES SIR!". As the clippers clicked on and placed at my forehead he tells me it’s time for a fresh start and he’s going to take me where no man has gone before. The clippers run swiftly over my head decimating my horseshoe flat. He is a man on a mission as he sprays Barbasol lather on my head and proceeds to shave it clean with and against the grain using a Gillette Pro razor. He commanded me to strip and lie down on the massage table. We were both aroused as I quickly undressed. "SIR, YES SIR!".

Lying on the massage table he held the Osters below my chin telling me there will be no more previews of what he’s going to do. I excitedly bark "SIR, YES SIR!" as the clippers ran right down the center of my chest. My thick, curly chest hair fell away as he removed it all. He held my erect dick with his left hand as he proceeded to remove my pubic hair. My torso is covered in Barbasol as he efficiently makes me smooth. Alec has been smooth the whole time I’ve known him. He has had me shave him a few times. It never occurred to me that he would make me smooth but I enjoyed every moment. After rinsing off, he started to run his tongue down my chest heading towards my cock. He took me in his mouth, and his facial hair tickled my crotch. I gently tug on his curls. He stands up and I quickly jumped off the massage table and pushed him into the chair. He looked at me with a mix of confusion and excitement.

He had a set of edger clippers on the vanity that he used for some of my hard-to-reach places. I grabbed them and pulled his head back. His eyes were wide open as I brought the edgers to his upper lip and removed his mustache quickly followed by his goatee. After shaving his face, I leaned in and we kissed. We were running our hands all over each other’s smooth bodies. I pushed away and took a seat in the chair holding my dick. "I need you to finish what you started." Immediately he dropped to the floor. As he was about to take me in his mouth he looked up and said, "I thought for a moment you were going to shave my head." Relieved, he got back to business. I laughed as he took me back into his mouth and I reached for the Osters barking "SIR, YES SIR!". I brought the hungry clippers to his forehead and ran them all the way back across his head. He released my dick and stood up staring at me and at his reflection in the mirror. He was in shock as he ran his hand along the stubbly path on his head. He turned to look at me and mouthed, "THANK YOU." as he sat in the chair.

The transformation was amazing. Alec had never had short hair and now he was clipper shaved. From the reaction of his dick, he loved this new sensation. He turned on the shower and stepped in to get rid of all the loose hairs. I followed him and we enjoyed running our hands all over each other. Purposefully I stepped in front of him nodding,as I turned my back on him pulling him in. There was no need for either of us to say anything as he pushed in slowly but firmly. I winced slightly gasping as I was overcome with euphoria. He started to rock slowly at first. He planted his hands on the shower wall for leverage and began to pound faster. With one last thrust he released, and I was filled with his warm semen. As he pulled out, he caught some and rubbed it on my head. I turned back to face him, and we kissed like we have never kissed before. He grabbed the Barbasol and raised it above his head squirting a large pile onto his stubbly scalp. Immediately I began to rub it all over his head as I reached for the razor. He dropped to his knees and again took my dick in his mouth so his no longer a virgin boyfriend can shave him smooth.

Arriving at the party hand-in-hand people were aghast, taking it all in. Many didn’t even recognize Alec minus his curls with his shiny bald head. As the crowd parted for us to walk through they broke into spontaneous applause, hooting and hollering. It took them a few minutes to notice the sparkling new engagement rings we were both wearing on our left hands. It was indeed a new beginning. (TO BE CONTINUED.)

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