[M/F] Best haircut ever

Disclaimer: Apologies for the length and pointless details, this is my first time writing up something like this. For the longest time I’ve had a preference for older women, and finally made progress talking to a lady in the most unlikely of places.

So, For the longest time I always cut my own hair. Being a guy and military son, I would just buzz my own hair and carefully trim in the mirror. Occasionally, a buddy of mine would help line me up. Thinking longer hair would look a little better, I decided to grow it out and start getting a professional haircut. Having no idea which barber to go to, I simply go to the nearest “Men’s/Sports” cuts around the corner. She washed my hair, massaged my scalp, put a hot rag on my face, all kinds of shit I wasn’t expecting. It actually made me feel really awkward. After the haircut was done, I paid and left. I can remember telling a friend how violated I felt having some woman massage and wash my hair like that. He laughed and made some lame feminine joke to me, as bro’s will do.

Skip a few weeks later, And it’s time for another haircut. I’ve let my hair grow much longer than I usually like, simply because I wasn’t sure where to get it cut. I didn’t really want to talk to anyone or have all this “froo froo” stuff done, I just wanted the hair cut and to move on. This time, I text a buddy of mine and asked where he gets his done. He recently moved but says he usually just went to a place near his house, roughly 5 minutes from mine, and it was quick and cheap. Perfect. I get in the car and head over.

It’s a typical rental barber place, a generic name, hiring “independent contractors” to come in to cut hair. I’m sure most barber shops operate the same. I walk in and there’s 3 older women, probably in their 40s, but God help me if I actually tried to guess, cutting hair and taking names. You don’t get to pick which one cuts you, it all just goes in order. In my mind, I already have made a preference on which one I’d like to cut my hair. She looks the most calm, laid back, and confident of the bunch. My name gets called and I breathe a sigh of relief, as my mental pick is the next available barber. I suppose it helps that she was also the most attractive. She’s a thin, healthy, and confident looking woman with her hair meticulously done and the only one without gobs of makeup on. I’m in my 20s and don’t think anyone couldn’t say she wasn’t attractive.

As the next few months go by, except for one occasion, I somehow end up paired with her for a haircut. Over those months, and only during the haircuts, we’d talk the entire time. Conversation came so easily and I was convinced she was just great at her job and loved talking. I never once thought she was interested in me like that. She was just a sweet woman at work.

Except, during this last haircut something was different. When I walked in, I was lead by three other people. We instantly packed the shop and you could tell all the ladies working felt overwhelmed. It was near closing time and they were going to have to start cutting people off. As we all walked in, they took everyone’s name but mine. I was honestly hoping I’d still be able to match with her to cut my hair, but given the circumstances I was probably out of luck.

What happened next was nothing short of a miracle. She finished cutting the client she had, walked to the back, and by the time she came back and was ready, I was next in line. She seemed rushed during her break and was frequently walking to the front during that time with papers and folders. I felt bad, knowing I was probably going to keep her past 7:00 PM. I expressed my concern, but she assured me it was okay. We began talking and it was as if she got in the zone and all the stress she appeared to be under just a minute before was gone. She was talking about her recent outings with friends, how she bust her ass trying to spin around a stripper pole, and how great my hair looked when I walked in. Conversation continued without fail and I said something with instant regret. We had just talked about how the place got slammed with customers and how they had to turn one guy away and he left all pissed off. Somehow this prompted a thought in me and I just came out with it. Uncontrollably, I asked, “Is there a way I can contact you directly? You know, to see if it’s a good time to come in.” I felt like an idiot. It seemed so blatant why I asked and I began expecting the soft let down a respectful, but hopefully flattered, woman would be so accustomed to.

Instead, She smiled and said of course! And as I was expecting a generic business card, she instead pulled out her cell phone and we exchanged numbers. I said thanks and that I’d give her a call in a few weeks. She told me to text her instead, since she’d be at work. I agreed, paid, and left to go home.

I’d lie if I said I wasn’t excited. My mind started questioning if maybe she really was interested in me. All the compliments she gave me earlier flooded back to my memory but my conservative nature admonished that and continued to fill my actions with restraint. No way would I actually text her, she’s just a sweet woman who doesn’t need to be bothered by some young horny guy.

But An hour later I get a text from her. My eyes grew large as I was still certain our friendship was strictly professional. Her text said, “Hey, just wanted to let you know Tuesday’s are the slowest and I’m off every Friday through Sunday.” My thumbs couldn’t type a message back fast enough. As they riddled my phone keyboard, my brain somehow went all in and my thumbs typed out “Oh, so that means you can get a drink with me tomorrow then.” What. Was. I. Thinking? I quickly wanted to recant but said No, it’s all or nothing.

15 of the longest minutes of my life go by and she responds with “:) sure” and we worked out a good local bar to meet at.

No shit. I guess she really likes my company, and all those haircut conversations, maybe we really did become friends. I was just always convinced it was just her “work attitude”.

Skip to the next day, I walk into the bar and see her sitting at a table, wearing a dress that compliments her body so well. I really hope she didn’t see my jaw drop. She looked amazing. It portrayed that classy, mature, confident nature I know she has. I sat down and asked if I had kept her waiting long. She said no, and as the waitress came by we ordered our drinks. The conversation went so smoothly, much better than my social anxiety predicted. After a few drinks, when she’d laugh, she’d put hand on top of mine. I’d carefully rub her hand with my thumb while smiling and giving the hardest bedroom eyes I could.

Around 9:45, and after what really was a fun night, she mentioned she should probably head home and I agreed. I walked her to her car and said I had a great time tonight and told her how easy I felt it was to talk to her. She smiled, said thanks and looked down briefly. I lightly grasped her chin between my thumb and index, carefully lifted her head up, and kissed her. It was one of those multi part kisses, where our lips neglected no part of each other’s. I told her to be careful on her drive home, and that I wanted to make sure she got home safely. She asked if I wanted to guarantee she got home okay. I said of course I did. She said, “Then get in”.

I got in her car and we headed to her place. As she unlocked and opened her apartment door, I couldn’t wait any longer, so I placed one hand on her hips and the other lightly closed the door. She turned with an anticipation and we began to make out. My hands running up and down her body.

She guided me to her bedroom, her bed neatly made. Her dress falls off her shoulders and hits the ground the same time my jaw does. She’s absolutely stunning. Her legs were tone and tanned, her hips were a perfect width and curved to compliment a tight core that even I was jealous of. Her breasts were much larger than her dress allowed for, and all attributes of her went together better than any girl I’d ever been with.

I’m sitting on her bed, leaning back on my elbows as she displays the work of art that is her body. She straddles me near my knees and begins to undo my jeans. I’m wearing a button fly, so as she undoes one of them, I quickly pull apart the rest with impatience. She laughs briefly but then her hands reach in and pull out my dick. I’m so hard from anticipation that she smirks, and like a woman who knows how to please, she begins to stroke on the shaft and suck on the head of my cock. My elbows give out and I’m fully on my back.

The noises, good god the noises she was making with my cock made me audibly moan. I’d never received head like this. Her enthusiasm to please was the biggest turn on to me. She pulled my jeans down the rest of the way and I stood up and with one arm hugged her at the hips and gently laid her on the bed. Her legs lifted up, her hand reached below her thigh and she guided my dick into her. I started off so slow and gradually began pushing deeper. With every full stroke I heard a high pitched moan. Her legs rose and she rested her ankles over my shoulders. She had lied to me earlier if she said she couldn’t do what she used to. I still hadn’t found what she must have been referring to.

As that position continued, I leaned over and kissed her, and her arms swung over my shoulders. I said hold on, and I wrapped my arms around her and picked her up. She let out a “Oh!” and I could tell she didn’t expect that. I sat down on the bed, assuming the bottom position, my cock never leaving her. When she got comfortable in position, my cock was balls deep inside of her, and she began to rock back and forth grinding on me. I could feel the tip of my dick pivoting back in forth in her, and feeling the spot she’d hit where she’d moan the most at. I let her ride for a few minutes until she was just barely moving and her mouth was just open, breath coming out and in with quick bursts.

I grabbed her ass and began going to town, our bodies clapping together that a fucking applause from a Presidential Address to the Nation. I told her I’m about to cum, and she yelled don’t stop. I didn’t expect such a direct order from her, given her petite and sweet nature. I kept going even after I came and somehow my dick stayed rock hard. Even after I pulled out my dick was still throbbing and hard, ready to go again.

I couldn’t believe the entire experience. How did we end up here and have such phenomenal sex? It all seems so surreal. She came back from the bathroom and I just held her in my arms until we both fell asleep. The next morning we showered and washed each other in the shower, neglecting nothing. We didn’t have shower sex or anything, but just showering together with our hands all over each other and kissing periodically was sensual enough.

We got dressed and she brought me to my car at the bar around 8 AM. The car ride was quiet but not awkward. When she pulled up to my car she said, “don’t forget about me” With a smile. I told her “how could I?” And I made a joke about how I still need her to cut my hair and make me look good.

This was a little less than a week ago, and I haven’t seen her since, but I haven’t had a haircut either. I’m kind of nervous to go back but feel like I could trust things would be somewhat normal still. I’d love to text her and see what she’s up to this weekend, but I’ll probably just wait for her to text me.

Source: reddit.com/r/gonewildstories/comments/459wei/mf_best_haircut_ever