[M/F] Best haircut ever | 2016

Update #2 Buried Below

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.

Update: This post got a lot more attention than I thought it would! Thanks for all the encouragement! I got a text back from her and she said work was swamped today and is only now starting to slow down. I asked if I could help her relax after she got off. Her reply: "I'd like that :)". So I'm heading over to her place around 8 tonight! If all goes well, you'll have to wait until tomorrow for more!

Update #2: Alright, this has been a crazy ride for me this far. To recap, this is my first time with an older woman and I can't help but be a little nervous. After our first night together my nerves calmed down a lot, but didn't diminish. I guess I never let my heart rate rest our entire first night together, even after the drinks I was still "on alert". I would feel as if that would have resulted in a disservice to her, but based on how tonight went, I would highly doubt it.

Anyway, I get to her apartment. It's in an area that I'd probably live, but not somewhere I'd want girls to see I live. I grew up mostly in the 'burbs and spent the rest of the time at my grandparents "farm". It wasn't much of a farm as it is a homestead. You see, my Grandparents are so broke they grow and raise up their own food. I do what I can to help, but mainly just "barter" to do work or give petty cash to my pawpaw for chicken eggs. I'd do the work for free or just give him cash, but I'd be kicking a workhorse in the mouth and probably couldn't give him a hug if he didn't think he earned it. But I digress, I lock my car and pull the handle to double check. I don't want my nerves to leave me exposed to any unwanted opportunities for someone else. Also, I had recently got my door locks fixed and this was a dying habit.

I get to her door and knock three times. I thought about trying to be discreet but I ended up knocking with authority. No one knocks on my door so when someone knocks like the fucking police my heart jumps and I'm on more alert than a long haired cat in a room full of rocking chairs. So I gave her the hard knock. I hear the door unlocking and for some reason thought about how fucked I'd be if instead of her a bunch of dudes opened up and just fucking jumped the shit out of me and took everything I had. This is my crazy paranoid mind y'all, it's pretty fucked up. Thankfully, it's just her. She's still in jeans and a T-shirt, and she's mid bite into what looks like a turkey sandwich.

"Hey! Come on in!" She said, much to my comfort.

I was inappropriately nervous, but talking always soothes my nerves. So, I asked her how work was. Instead of giving me some lame and basic "Good" with nothing to work with, she began explaining her day to me, humbly mentioning that she did well on tips. I smiled and said that's great. Inside, I was hoping I didn't appear unimpressed. She knows my career and knows it's associated with high salaries. I'm trying my best not to appear conceited.

She mentioned that she had seen her cousin today that she misses a lot. I asked about her. She started showing me pictures on her phone of them, which appeared to be decades old. The way she talked about the "simpler" days calmed any nerves I had. It's like she has that power over me. She just knows how to make you relax and slow time, just enough to appreciate every moment. After she finished her sandwich, she said she'd be right back and went to her room. She didn't close the door and I could see her changing near the closet. Seeing her walk back out with those pajama pants and small, but loose, t shirt made my dick jump in my pants. Literally. I felt it move and I can remember thinking how attracted I was to her if my dick really was acting independent of my brain. Good Work, D.

She walked back with some photos of her back in the 80s (Polaroids). I can remember playing with a Polaroid camera as a kid, and haven't seen a photo from one in a minute. She said she was a teenager but she definitely looked more in her 20s. She looked cute and you can definitely see the similarity in the pictures. Her smile hadn't changed a bit. She's a blonde now, with piercing hazel eyes, but in the pictures her hair is brown. I inquired about this. She laughed and said that she does dye her hair now, but over time her hair just grew lighter. And in case you're wondering, The pictures confirm that brown hair and hazel eyes are a dangerous combination.

We left the pictures on the table and she asked if I wanted something to drink. I could see her tits poking through her thin shirt... it took the strength of 100 men to hold my hands back. I asked for a water. We walked to the couch and sat down, her legs curled under her and she was covered with a Mickey Mouse blanket. I'm about 2 feet away, sitting about mid couch as we gave ourselves room to just talk. The temperature outside is warming up but her apartment is cold as ice. I kept thinking how maybe she used the ol' "turn on the A/C and cool this place to hell so we have to cuddle" technique on me. I wasn't trying to jump right into things, as I really wanted to get to know her more. If we relate more personally, then we should relate more sexually. At least that's the thought.

I rub my arm and she notices I'm cold.

"Awe, baby, are you cold?" I let out a soft acknowledgment and she lifted the blanket. I didn't need a second invitation.

As I crawled on the couch to her, I carefully placed one hand on her hip and the other holding myself up near the pillow. Most of my weight is on my right hand to the right of the pillow, the left is just there for the grips. My core was straining from doing what seemed to be the hardest plank of my life, but it was worth it. She covered me with the blanket before I moved in. I kissed her neck and she lifted her face up and away, giving me as much room as I needed to cover her with blessings. I debated taking my time, but decided to go straight for her lips. We kissed for a moment and she commented on my prickly beard. I laughed and mentioned I needed to trim. She disagreed and said it looks good on me.

While kissing her I simultaneously lifted her shirt enough to get a hand on one of her breasts. My right hand still propping myself up, my core, ready to give Louisiana its first earthquake. I was losing strength in my arm, but at least it was giving me a good pump, so I got on my elbows with my face above her waist. I kissed her stomach, slowly, and worked my way to her hips. My hands now free and unoccupied, needed to be put to work. With just two fingers, pivoting at the thumb, I lightly pulled down her pajamas. Just a few inches, but enough to see the mound and give my tongue stretching room to her clit. My kisses got closer, and as I was just to the right of her clit, I sucked on her just a little. Harder than I intended, right on the outer lips. I say harder than I intended, because when I did this, the inner lip went with it, and I could taste her. Having broke the threshold, my tongue slithered out and went to work. I loved how wet she got and how covered my beard was with her juices. I swear Her panties were as useless as a screen door on a submarine. With a gasp she sat up a little, put her hands around my shoulders and motions me back up.

For some reason, I sat up. I back handedly wiped my face like a kids first time with ice cream, and took a breath. She slid her pants off and with the blanket to the side now, she undid my pants. How my boner didn't drill a hole in my jeans, I still don't know. As she's doing this I have a "top-down" POV of her ass and my hands refused disobedience. I grab her ass, thick, but not big, and just enough to fill my hands. She reaches in my pants to pull out my dick, but it's too hard to just flop out, so I lifted up a little and pulled them down further to give her more access. My balls are fucking freezing. She covers them with one hand and with her mouth begins sensually licking and sucking on my member. The cupping of my balls as I gripped her ass and relaxing on the sofa made me want to fuck her so hard. I was ready to give her the hardest ride I could.

She comes up for air, and starts slowly stroking while she asks if I could stay the night. I say I can, but I'd have to leave early for work. FUCKING AMATEUR HOUR OVER HERE. She says I shouldn't stay and she didn't want me to be late for work. I half smirk and say she's right but we still have time and I didn't want to leave just yet. She smiled and pushed me on my back. At this time we're taking up the whole couch (longways), my pants are halfway down, she's bottomless, and she begins to work on me with her mouth again. This time she's stroking full fisted and working the tip. The slurping and popping noises, or however you describe them, with the sound of wet friction has got my dick pulsing and ready for blast off. I look down and can see her breasts hanging through the large cut out of her VNeck shirt.

I let out a quiet but urgent "okay, okay.." Privately wishing she wouldn't hear so I could cum in her mouth. She heard me, detached at the lips, and began vigorously beating my dick. I couldn't help but notice the amount of energy she has. As I came, jizz flew all over my jeans and her shirt. Once all was out and the only thing left was the cum slowly coming out of my pecker from her slightly tighter gripped strokes, she went down and polished me off with a feeling I have yet been able to describe. She quickly grabbed a tissue from the table next to her couch and wiped off my jeans and her shirt. I wasn't ready to put my dick away so I left it out for a moment as the stiffness died down and my dick wilted over like a flower desperately needing water.

I sat up, hugged her, then laid back down and held her in my arms, face to face, my dick still out, resting in front of her pussy. We covered up in the blanket and warmed up for a minute as my hands rubbed her back and ass. I pulled my jeans back up. She stood up and out her pajamas back on, and I stood up with her, and while facing her, I slid my hands under her pajamas, grabbing her ass. She gave me a light kiss and said "Don't be late for work tomorrow, text me."

"You're killing me." I complained with a smirk.

"You're a big boy, you'll be fine." She teased as she tapped on my chest. "We'll do this again, don't worry." she reassured with a smile.

I went home and regretfully got to work on time this morning. All in all it was a great night and we've been texting most of the morning. Haven't made any plans yet and I'm probably going out with some friends after work. But given the word, I'd bail on them in a second. Not sure when or if to bring up any conversations about a relationship or anything. To be honest, I kind of just like what we have now. I feel she knows our age difference is insurmountable and we're in this for the fun of it. We'll just have to let this train run its course. We'll figure it out when the track ends.