Please Sir, Cut My Hair by Shant

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I was lucky enough to retire at 55. It had always been my goal to retire at an early age and then get to do all the things that were on "my bucket list."

The first year flew by rapidly. I was traveling all the time, and rarely had a dull moment. After about a year though, I found myself tired of always going somewhere, and decided to stay home and work on projects I had been putting off doing for so long.

I soon realized that being retired, while all my friends were still working, resulted in my spending way too much time alone. I have a lot of interests, but I wished I had more things to keep me active. A big part of the time, I was just plain bored.

I decided to place an ad online and see if I might meet someone who shared some of the same interests I did. My ad read: I’m 55, in good shape. I have a lot of great friends, and I like to keep active. I retired last year and find I have way too much alone time on my hands. Would like to meet a guy that shares some of the same interests I have.

I’m a retired barber, and find I miss cutting a good head of hair. Would be great to meet a guy with great hair who enjoys having someone pamper his fantastic mane.

My hair is dark brown, very thick and is about five inches on top and three inches on the sides. I would love having someone play with my hair as well. As a barber, I got to brush a lot of great hair, but I rarely ever had someone brush my hair. I love the thought of someone brushing my hair and playing with it.

Age is not a major criteria, but a good head of hair is definitely a major plus. If this appeals to you, just email me and we can talk and see what, if anything, happens. I’m very easy going and in no rush to jump into anything, but it would be great to meet some new people and have some fun, too.

A couple weeks went by and then one day I received a response to my ad from a guy named John. He actually only lived about fifteen minutes from my house.

He said he was 35 and he also had always been attracted to a guy with great hair. He wrote that he loved getting his hands in a guy’s hair and having the same thing done to him.

He said my ad caught his eye and he thought this might finally be the chance to meet someone who loved hair as much as he did. He had never confided in anyone about how much he loved playing with some guy’s hair. He said that my ad was even more tempting, seeing that we lived so close to each other.

He wrote that he had never seen an ad like mine before, and thought maybe this was the chance to do some of the things he had always thought about wishing he could do.

When he read that I was a barber, he said he really got excited. He thought could there ever be a better opportunity than this? To have a barber, who loves great hair, help him live out some of his fantasies would be great.

He wrote, "My hair is a dark chestnut color and has bright highlights. It is very thick and has great texture and has a slight wave to it. My hair is so thick that I can not use a normal comb to comb it, but have to use either a wide tooth comb or a brush. My hair on the sides is about four inches long and I brush it back, above my ears. The top I have been growing for several months and is now almost eight inches long. It is the longest that it has ever been."

"My hair has a naturally slight part on the left side and I brush it all up and back," he said. "My hair is slightly coarse and has such great body that once it’s combed, it stays exactly in place all day long." It really did sound like he had an amazing head of hair. The thought of getting my hands in it, was an immediate turn on for me.

He said he received a lot of compliments from guys telling him how great his hair looked. He hoped that the conversation would lead to the guy being interested in playing with his hair. He said it never happened though, and he was way too shy to initiate the conversation.

He said he always hoped he’d meet a guy he could feel comfortable enough around that he could talk about how much he was turned on by great hair. "I’ve never really had much luck on these websites, but I figured what would be the harm in contacting you? I could be missing out on a great opportunity just because of being afraid to respond to someone," John said. "If you’re interested in meeting, we could easily get together for coffee or a drink whenever you’d like. It’s great that we live so close to each other."

I felt a rush when I read what he had written. I thought to myself, "Don’t chicken out! How often do you get a chance like this? To actually get to meet someone who enjoys hair as much as I do never happens. Do this! Go for coffee and see what happens. That’s why you placed the ad. Now’s your chance to do something about it."

I wrote him back and we decided on a time to get together. From the moment we met, we both felt comfortable around each other. We were both pretty good looking guys. We later told each other that from the moment we met, we were immediately attracted to each other, and especially loved how great each other’s hair looked.

The entire time we were talking, I could not keep my eyes off his hair. It really was great looking. I finally decided to bring up the topic I knew we both wanted to discuss. "You’ve got an awesome head of hair there. You’re really lucky to have it. It’s so thick and has such a great shine to it," I said.

"The slight wave you have makes it stand out even more. It really stands up great and the waves just seem to fall naturally into place. Have you worn your hair like this for a long time?" I asked. "I would absolutely love to brush your hair. Would you like to come over to my house and let me brush it for you? It’s been awhile since I’ve had my hands in a head of hair as awesome as yours and it would be a lot of fun."

"That would be great!" John said. "Would you let me brush your hair too? You really have a great looking mane yourself and I would love brushing it and getting my hands in it, and seeing all the different ways I could get it to look."

"I love having someone brush my hair but it doesn’t happen very often. I know how lucky I am to have it," John said. "Everyone is always telling me how great my hair looks and that I should never cut it short. To be honest, I get so many compliments about how great my hair looks that it has actually made me afraid to try a different style haircut."

"There’s a part of me that would really like to try something different with my hair, but I dread all the comments I know I would get from everyone asking why on earth did I cut my hair?"

"I wish I had the nerve to do it and not care what anyone thought and just went ahead and cut it. Once I did, I think from then on, I would change how I wore it all the time."

"I’m always thinking about cutting it short and then growing it out again. I get more and more tempted and I know that one day, on the spur of the moment, I’ll just get up my nerve and go ahead and do it."

"My younger brother, Gary, has hair just like mine. Every time I see him, he has his hair cut differently. He told me that his barber encouraged him to start cutting his hair in a different style all the time."

"His barber told him that he had such great hair that he should really take advantage of it, and have some fun with it while he was young, and wear it a lot of different ways."

"Flaunt it, if you’ve got it! he told Gary. He said if he had hair that was as fantastic as Gary did, he would be cutting it different ways all the time. He said it would be fun seeing how many ways Gary could look. He told Gary if he ever decided to go for a new look, that he would love to cut it for him."

"My brother said he started thinking about doing that and finally got up his nerve one day and told his barber to go ahead and cut his hair anyway he wanted. The barber ended up giving him a slightly longer style flattop. It was squared up the sides and back, with the front just long enough to brush back. The rest of his hair on top was about an inch long. It stood up so great that he really did look awesome with his new haircut."

"My brother said the feeling was unreal when the barber took his scissors and started cutting all his long hair off and then running the clippers up the sides and back. He said he couldn’t believe that something he had thought about doing for such a long time was actually happening."

"It really flipped me out at first watching all my hair get cut down to less than an inch long. It was such a rush!" he said. After the haircut was finished, he said he really liked his new haircut and didn’t regret cutting his hair short at all.

"Gary said he doubted he would ever let his hair grow as long as it had been. He had worn his hair long for several years, and had always loved it, but he said that he was really glad he had gotten up the nerve to go for the big cut. He said he has a lot of fun trying a different looking haircut whenever he gets the urge. He had always hated going to the barbershop before, and now, couldn’t wait to see how different he would look after he had his hair cut again."

"With my hair being just like his, when he talks about how glad he is that he cut his hair, it tempts me even more to get mine cut. I’ve had many barbers tell me that I could cut my hair just about anyway I wanted, and it would look great," John said.

"I know most of them were trying to see if they could convince me to sit down in their chair and let them give me a short haircut. I knew they would love getting to do that. I can usually tell by the smile on a barber’s face how much he would like to cut my hair short."

We finished our drinks and I asked him, "If you’re not doing anything now, how about coming over to my house and we can talk some more and play a little? I’d love to brush your hair for you and run my hands through it, and have you do the same to me."

"Sure," John said. "I know I’d like to get together with you. We both want to get our hands in great hair and here’s our chance. We both know how rarely that ever happens. I have no plans for the rest of the day and would be glad to come home with you."

We got to the house and I showed him around. We then went upstairs and I sat him in a chair and started brushing his hair. I think that both of us immediately got hard ons.

"It’s wonderful getting to brush your hair," I said. "It is so thick and full. It’s really beautiful. It would be fantastic if we both want to do this again. I would be disappointed if this ended up being a one time only thing because I’m really enjoying myself. We’re getting along really great, and we live so close to each other, that we might get to do this on a regular basis. It’s obvious you love great hair and get turned on by it, as much as I do." I said.

"Being totally honest with you," John said, "My biggest fantasy has always been instead of going to a barbershop, was to find some hot, older man sit me down in a chair and cut my hair however he wanted."

"I don’t know why it is, but the thought of having an older guy doing that has always been a real turn on for me, especially if the guy was really good looking and hot. You are definitely all that, and even better, you’re a barber. It couldn’t be more perfect. Would you like to give me a haircut?" he asked.

"I have always been interested in guys that are older than I am. I have wanted to be in a relationship with an older guy for as long as I can remember. The thought of it makes me feel, I don’t know, I think the word, secure, would best describe it. I think it would be great to have a person, that has experience and can help guide me as a mentor, and also be a partner."

"Growing up, I had no relationship with my father at all. He barely acknowledged I even existed. I couldn’t wait to finish high school and get out of there. Having no siblings, I never experienced any male type bonding, until high school."

"I’m sure that because I didn’t have any relationship with my father, is a big part of the reason why I have always wanted to be with someone older."

"I hope it’s okay to ask you this, but are you interested in being in a relationship? If you are, would you be interested in dating someone like me and seeing how it worked out? I haven’t dated anyone in so long that I’m probably making a fool of myself, and being way too forward, but I sure would like to see you again," John said.

I’m sure that John could tell by the smile on my face that I would definitely like to see him again. I continued brushing his hair, all the while admiring how gorgeous it was. I had such a hard on as I kept running my hands through it. It had been a long time since I had done anything like this with a guy and especially a guy that was so hot looking. It was fantastic."

"This has been a great evening for me too," I said. "It has been ages since I’ve had such a great time with anyone. I really had never thought about being in a relationship with a younger guy, but if the guy were you, I would definitely consider trying it and seeing how it could turn out."

I decided it was time to start being more aggressive and see how far John would be willing to go along. "So, you’d like to be my boy, would you?" I said, as I continued running my hands through his awesome mane. "You think you’d enjoy being involved with a guy like me? You’re such a hot looking young man and are so attractive that any guy interested in being in a relationship with a younger guy, would jump at the chance to be with you."

"If you wanted to be my boy, your hair though, is a little too long, and would need to be cut. Actually, I think it’s time you get rid of all that hair and you let me give you a short macho looking haircut. You would look so much more like a hot stud, instead of some pretty boy, without all that long hair you have. Would you like me to cut your hair for you? That would show me if you really are serious about being in a relationship with me." I said.

John surprised me by immediately saying, "Please Sir, cut my hair however you would like. If cutting my hair gives me a better chance of being your boy, then go ahead and cut it. I’m so stoked that I am actually going to get to live out one of my greatest fantasies. I don’t care how short you cut my hair."

"I have never found the man that I wanted to cut my hair. I think you are definitely the right guy. You being a barber makes it even better. I don’t have to fear that you are going to butcher my hair and I can tell by how great your haircut is that my hair will look good when you are finished."

"I’ve always been so in love with my hair that the thought of it all coming off at once has been way beyond my wildest imagination. I’m already hard just thinking about it!"

"The thought of you being in charge and deciding how you are going to cut my hair, makes me so stoked that I’m already about to explode, and you haven’t even started giving me a haircut yet! This is such a rush, being afraid, excited, and horny, all at the same time!"

"I get so turned on just combing my own hair. I don’t know why, but playing with my hair has always made me horny. I’m always running my hands through it, brushing the front back so that it isn’t hanging in my eyes. I constantly have to keep pushing it out of my eyes now that it is so long. I can’t wait to see how it looks and feels not being in my face anymore."

"Sir, I really want you to cut my hair! Cut it all off if that’s what you want to do. I want to watch in the mirror and see it as it is buzzed off and falls onto the floor. I can’t imagine what I will look like after having had my hair long for so many years. I can’t wait for you to do it. You are such a hot looking man that it’s driving me crazy thinking about you cutting my hair!"

"Before you start cutting it, would you play with my hair for awhile? Pull my hair and be rough with, it if want. Talk to me like an angry father would. Tell me how you are going to punish me by cutting off all my pretty hair that I am so vain about! Really give me a sharp tongue lashing about what you are going to do my hair."

"Really curse me out while you’re manhandling my wonderful mane! I’ve always fantasized the guy in charge would be really aggressive and would be really turned on getting his hands in my hair. Tell me what you are going to do to my beautiful hair that you hate so much!"

"I hope what I just said doesn’t freak you out or anything. I just get turned on even more, the more aggressive you are with me. I think we feel pretty much the same about how attracted we are to really awesome hair. To meet someone that I can talk with about how much I love my hair, is great. I’ve always wanted to share my infatuation with someone."

"Do you know how you want to cut my hair? It would be a rush if you gave me a short haircut. Is that what you would want to do? If I were your boy, it would be up to you to decide how my hair is always cut."

"You said you thought my hair really looked beautiful and you would enjoy getting to run your hands through it. Do you want me to keep it like this for awhile so you can play with it? Whatever you want to do is up to you. If things work out between us, I’ll love having you give me a different looking haircut all the time."

"How about giving me a flattop sometime? I’ve never had one, but I think it would probably be one of the wildest times ever. Seeing you cut almost all my thick, long hair off, and then cutting me down into a flattop would be unreal. I’ve fantasized for years about doing that. I’m actually about ready to explode just thinking about you doing it!"

I continued to brush John’s hair and run my hands through it. It was so sensual and I was actually delaying the haircut because I loved how thick and long his hair was. I couldn’t get enough playing with it.

I finally decided it was time to start cutting John’s hair and let him get to experience the fantasy he had always had. "You’ve been a good boy this evening and I have a special treat for you," I said. "Come into the bathroom and I’m going to sit you down and really get my hands into that awesome mane of yours. My handsome young man is going to get his hair pampered like he never has before. Just touching your hair causes me to instantly get a hard on. We’re going to have a lot of fun with that pretty boy hair you have. Your hair on top is so beautiful. I bet you love getting your hair brushed, don’t you, boy?"

"Yes, Sir. I get so turned on just thinking about someone playing with my hair. Having someone brush it is really great."

"Whenever I hook up with a guy, I hope they will want to manhandle my hair, but they never do. I’m not comfortable being the aggressive one, so I never say anything about his hair or mine. I just keep hoping that someday it will happen. I’m sure you understand completely how I feel."

Three walls of my bathroom were solid mirrors so we had an amazing view of what was about to happen. I adjusted the lights so that it was light enough to see everything, but not so bright as to be blinding.

I washed and then dried his hair. It looked amazing. God, his forelock was beautiful! I just couldn’t quit running my hands through it and brushing it over and over again.

I stood in front of him and brushed all his hair straight back. The top must have been at least eight inches long. When I ran my hands through his beautiful locks I couldn’t even see them. It was going to be a total rush to give him a much shorter haircut and watch his beautiful hair fall to the floor.

I decided that since we had talked about seeing each other again, that I’d rather not cut his hair really short tonight. If things ended up with us seeing each other, I would not want to cut all his hair off and have nothing to play with. I would much rather get to run my hands through his mane and play with it all the time.

Cutting it all off would be a real rush, but then there would not be much hair to play with for quite a long time. I definitely would rather play with great hair all the time. Cutting it all off would be a bigger rush, but it’s only for one night and then it would take months before it would be long enough to get my hands in it. John’s hair was so beautiful that I knew it would be a long time before I decided I had played with it enough before cutting it down short.

As I brushed his hair, I could tell that John was enjoying this as much as I was. As I ran my hands through his gorgeous mane, I heard a slight moan coming from him. It was obvious that he was turned on as much as I was.

I was in heaven. Playing with this handsome young man’s beautiful hair was totally mind blowing. It had been ages since I had the chance to play like this with anyone. I was so stoked and couldn’t believe that this was actually happening. I was already thinking about giving him the extra key to the house and have him start moving his stuff in, if we continued having such great times together.

I reached over and got my scissors and comb. I stood behind him and grabbed his forelock and said, "Yeah man! If you are going to be my boy, most of this pretty hair you have is going to come off! I’m going to give you a real man’s haircut, instead of this girlie, pretty boy mane that you have! Do you want me to cut your hair? If you want to really be my boy, you need to cut off that long pretty hair of yours. Are you ready to get rid of all your pretty hair?"

"I can’t wait to see this happen," John said. "I have wanted to do this for years and I’m finally getting to do it! Go ahead, Sir, cut my hair!"

John was totally mesmerized watching me, as I combed his awesome forelock straight up and sliced off about four inches of his lovely, thick, shining forelock. I didn’t think it was possible to be any more turned on than I was. Because of Covid, I had not had physical contact with anyone in almost two years. I had forgotten how great it could be.

I kept lifting up his beautiful locks and cutting them off. I left his hair about three inches long on top so I would have plenty of awesome hair to play with again. I continued taking about three inches of hair off his entire head. When I finished cutting it, I stood behind him and continued brushing it and running my hands through it.

"Your hair is so beautiful! I just want to keep running my hands through it forever." I said. "I hope you like how your haircut looks. I think it looks fantastic. You still have enough hair to comb a lot of different ways. I also wanted to leave it long enough so that I would have plenty of great hair to play with again."

I thought after finishing his haircut we would go into my bedroom and really have an intense time. John surprised me, however, and said, "We’re not all done yet, are we? I really want to get my hands in that mane of yours and play with it. Your hair really turns me on, too!"

I sat down in the chair and said, "I’d love to have you brush my hair and get your hands in it. I really get turned on by someone playing with my hair and it’s been forever since anyone has done that. It’s easily been more than two years, thanks to Covid."

As I sat back and relaxed in the chair and enjoyed John playing with my hair, I thought that this might possibly turn into a really fantastic situation for both of us. I definitely thought that he was a really nice guy.

"You know," John said as he was brushing my hair, "Your hair really is amazing. It is so thick and I can’t believe how long it is on top. It’s unbelievable how awesome your hair is. I love it!"

John continued brushing my hair and then said, "I think that your hair on top is a little long though, and needs to be cut. I want to cut an inch of your beautiful hair off the top. I want to leave the sides just the way they are. With all that hair you have, you won’t even notice that I cut it. This will also show me if you are interested in being in a relationship with me."

I had never had anyone other than a barber cut my hair, but I thought it would be okay and the thought of him cutting my hair really did turn me on. With him only taking hair off the top, it really would not be noticed, and I could always blend the top and sides together if needed. "Go ahead and cut an inch off the top if you want. Who knows, maybe we’ll end up being each other’s barber from now on."

John stood in front of me and brushed all my hair back. He then took a comb and said, "Oh man, I am really excited about getting to do this! You really have great hair, too and I can’t wait to cut it!"

I watched in the mirror as John combed a lock of my hair and cut off an inch. I couldn’t believe how turned on this made me feel. It was so hot, compared to just sitting in the barbershop chair and getting my hair cut. The guy that cut my hair had probably been cutting it for about fifteen years and it really had never been much of a turn on. I usually got it cut every month so the change was never all that dramatic.

Having such a handsome young guy cutting my hair for me, was just the ultimate experience. Knowing how much John was loving cutting my hair made it even more intense.

Who knew what could possibly happen here? The physical attraction between us was really great. We really enjoyed the time we had spent together tonight. I was optimistic that there would definitely be more good times ahead. It would be great to just take it slow and see what happens.

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