New Haircut (M/F)

I prefer to let my hair grow out because haircuts in the past few years have gotten expensive. Being in college I dont have alot of time or money to go every time I need a trim but today was special. Cassy and I were assigned to work on a history project together. We discovered that we both had an interest in ancient Rome and its rise to power. Now who was Cassy? She was a looker. She was probably 5’4 definitely a C cup, maybe bigger. I’m a boob guy so maybe I was embellishing. Either way I definitely liked what she had. Her hair was reddish blonde and it was cut to her neck so when she wore less clothes in the summer you could see her upper chest and upper back. She had a tribal tattoo peeking out from the middle right side of her back. Her eyes were blue on the brighter side and she and I got along rather well. I felt like this was the perfect time to ask her out. In hindsight there probably were better times but you know guys, we don’t always do that.

Cassy was a girl I went to high school with and now we shared some college classes. She always noticed when I got a haircut and I took that as a sign she liked me. That was pretty much it though. Other than getting trimmed, she didn’t seem to ignore me but didn’t really acknowledge me either. Yeah I know, why would I even be interested in her? She was pretty chill and never had a boyfriend. She also didn’t seem like the type to NOT WANT a partner either. So I wanted to ask her out but I decided to look better than I did currently when I do so. After all what could be the worst thing that happens?

After school since I had the day off from work, I looked up a hairdresser place. I was going over to Cassy’s later tonight to start the project. My game plan was simply to get a haircut and have her see it so she would start off the night “acknowledging” me. I wanted to look good so I decided to splurge a little and go to a nice salon that catered towards men. You know one of those places where they do shave, shampoo, massage, the whole nine yards. The issue was that there wasn’t any of the major brands around me but there was a stand alone salon that advertised that they basically only catered to men.

There was one a little bit of a drive from my dorm but I figured it was worth it. I called and asked if I could make an appointment for as soon as possible. To my surprise I was able to come in at any time.

“Yes it’s a slow night, I sent the other two girls home since we don’t have anymore clients for the night” said the lady over the phone”

“Okay cool i should be there in about 30 minutes”

“Okay I’ll put you down” she paused, “What is your name?”


“Phone number Mike?”

I gave her my number

“And what would you like done?”

I told her my plans for the night and what I wanted.

“Okay honey, I’ll put you down for that. I should have you ready to go before it gets too late”

“Thanks!” I said

“See you soon, thank you for calling”

“Bye” I hung up the phone. I got a change of clothes because I was going straight to meet Cassy and didn’t want those tiny hairs poking me all night.

I got there and walked in. There was a woman sitting in one of the chairs who had dark brown hair hiding the silver gray hairs underneath. She had to have been somewhere between 40 and 50. She wore light make-up and greeted me with a smile.

“Hey honey are you Mike?” She spoke as she got up to check me in. Now that she was standing her height was only a few inches shorter than mine but then the most noticeable feature was what her apron was trying to conceal. To say she had quite a pair of breasts would be a gross understatement. They didn’t sag much but were definitely natural. I tried my best to advert my eyes but I had a terrible feeling she noticed. I feel like if you have something that big on your chest that you notice people looking there. I brushed it off though.


“Welcome in follow me. My name is Kelly”

We walked past the chairs and I tried to catch another look in the mirrors we passed. No luck. I sat down in another chair next to a sink.

“So what will it be, honey?”

“Nothing fancy just want to look good for a date tonight”

“Oh my. And who’s the lucky lady?”

“A classmate”

She wrapped me in one of those waterproof covers and had me lay my head back.

“Lucky girl. What’s the plan honey?”

“Studying for a college course”

“Not much of a date but I guess it’s what you young kids do nowadays”

“Maybe not but I’m hoping tonight will change something.”

She nodded

Kelly turned on the faucet and the sounds of the water blocked out any noise. I looked at her to see of she was taking but she seemed to know what the water was doing. It was a tad cold it first but quickly warmed up. she ran her fingers through my hair making sure every follicle was wet. Her fingers ran around my ears, forehead and down the back of my neck. I looked at her again and she looked very focused so I just closed my eyes. I thought about how good it was feeling and how relaxed I was. My mind wandered and I started to think about Cassy and how maybe she would be doing the same with my new haircut. Maybe I would be laying down on her thighs. Maybe she would be topless. I was thinking of my head between Cassy┬┤s tits as she rubbed my- Shit I had a full on hard-on. I wasn’t overly well endowed but I was wearing gym shorts and boxers and that’s not the greatest cover up. I tried my best to hide it and kept my eyes shut so I wouldn’t raise suspicion.

Kelly stopped the water and put some tea tree shampoo into her hands. She started to lather my hair and my scalp repeating the same motions as she was doing before when she was getting my hair wet.

All the massaging was starting to relax me again and she started to rub her hand on my hair harder, really making sure she got every inch of my scalp. She took the water sprayer and rinsed the soap from my hair. Kelly then repeated the same process with conditioner.

“Would you like a nice warm towel on your face to relax before heading back to the front”

“Is it extra?” my bank account said.

“No honey, just an option”

“Let’s do it then”

She grabbed a towel from a little box I assumed to be a warmer and placed it over my face. I’ve never done it before and the mildly hot towel felt really nice. Then my whole face was covered. She started to massage my forehead, temples, and cheeks. I felt like I was in heaven. She reached for a towel and got a lot of the water out but still left it damp. She removed the towel and I opened my eyes. She made her way around the sink and as I lifted my head up I caught a quick glimpse of that godly cleavage. It seemed like more was showing but I brushed it aside.

“So Mike, are you ready?”

Kelly touched my upper arm to probably coax me to my feet. She then led the way over to the same chair she was sitting in when I walked in. I took a seat in the swivel chair that goes up and down. After a couple pumps with her foot, She slowly spun me around to face the mirror.

“Just a trim?”

“Yeah like a said, nothing too much just noticeably different”

“Sounds good sweetie.” With that she quickly squeezed my shoulders and walked in front of me. I couldn’t help but look and notice that she had quite a nice shape behind her jeans. Think of your friends hot mom. Not like skinny or anything but obviously older and more mature and is doing a great job of keeping herself in shape. Kelly had that kind of ass.

She returned to behind me and I made eye contact with her. She quickly smiled and showed some small crows feet next to her eyes. She started with the comb and carefully made sure my hair was knot free and straight. She seemed to take longer than it would usually take. But I didn’t mind. It’s not like she had any more customers.

She returned to her station in front of me and grabbed her scissors.

“Shit!” She dropped them “I’m sorry excuse my words.”

“You’re fine i won’t tell anyone”

She gave me a pity laugh and bent over to grab them. If I didn’t know any better I swear she wanted me to look at her but because there would have been a better angle she could have picked them up from. But I’m here for a haircut and there’s no way this random hairdresser is hitting on me.

She started to cut my hair and slowly made her way around my head. She started at the sides and worked her way up. She got to the top and it looked like she was having trouble.

“Sorry honey” she let the chair lower and returned to the top of my head. Kelly got even closer to me and I was suddenly looking right into her open shirt. She had freckles and sun spots covering her upper chest but it wasn’t a deterrent in any way. Each cut sent the slighted jiggle down to her chest. For the first time that day I smelled her. It was a long day’s work mixed with the smell of passing the perfume section at your local department store. Not bad in any way. It was quite nice. I found myself trying to secretly take in more of it. That mixed with her beautiful chest started to stir my blood again and I found myself rock solid again.

“Doin okay?”

“Yeah I’m good you?” I tried to look at her

“We are doing great and should have you out of here in no time.”

She pulled away, looked at me and smiled. She then started to work on my sideburns and spent a lot of time “comparing” each side to make sure it was even. Eveytime she did so, Kelly made it a point to bend down facing me so I could get another view. I’m sure that wasn’t her intention but it became increasingly harder to believe that. I would go soft and then she would “compare” and I would go hard. It was starting to drive me crazy. But as soon as it started, it ended. She went behind me and put her hands on my shoulders again only this time they were a little bit lower touching my upper chest. She brought herself to me and I felt her rack press into the back of my head.

“Everything good honey?”

“Y-yes” I swallowed.

She took off my smock and bent over again to check for the 20th time.

“She’s gonna like this alot mike.” She turned the chair and let me out. “If I was your age well-”

I gave her a smile, I got up and noticed I was still sporting half a boner but I just tried to act casual.

We got to the register. And Kelly removed her apron and revealed that the apron was holding them back. What was an amazing set of boobs before became incredible. I couldn’t help myself and just looked.

“Sweetie, don’t you have a date tonight with a younger woman?”

Fuck, “Im so sorry I was just-”

“Your total is $37”

I swiped my card and it got to the top screen. I quickly tried to think of a good tip but Kelly grabbed the card reader.

“No need honey. You save the money for your lady.”

“Are you sure?”

“Of course” she quickly looked me up and down, “She’s gonna be lucky to have you” she gave me a wink.

“Thank you” I made my way to the door.

As I went through she said one more thing. “Have fun tonight you. I know I will.”

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