She’s been cutting my hair for years, ever since I was young. When I hit puberty I really took notice of her body. She’s always been a milf to me. I used to sit on the counter at the shop to try to get a good peek down her shirt. Well…some things never change. I still take a look if the opportunity arises. Recently though during a typical hormone-filled exploration through porn I got an idea. A bad idea, yet oh so good.
Over the years we’ve gotten to know each other quite well. She’s pretty much a mother figure in my life. But not so much of a “mother” that I’m not sexually attracted to her. There was a short time where I dated her daughter and had the incredible opportunity of indulging certain details to her about what her daughter and I were doing. It could be somewhat of a turn-on at times. Needless to say, the line of communication between us is quite open. Anything is on the table.
Back to the idea. It had been a few days since I’d jacked off. After about 3 days of restraint, all sense goes out the door. I was about 5 days overdue. I struck up a conversation with her over text and jokingly said that there was a porn star that reminded me of her. I sent her a picture of the porn star and hinted at the fact that I wouldn’t mind doing to her what the guys in the film did to the actress. I opened up for the first time about my crush on her since I was young, and how she’s at the forefront of my mind whenever I come across the word “milf.” I didn’t want to make it awkward or be disrespectful, so I didn’t push the issue too much. She did, however, send me a picture of her cleavage at the end of the conversation. It was just cleavage, but it was sent by the woman who now knew that I had been catching glimpses down her shirt since I was a boy. To me, it was piece of a dream come true.
A few months go by. I had felt guilty after the first conversation once I masturbated to her picture. She was a married woman after all, and I was pretty sheltered growing up. Guilt comes swiftly once my libido leaves. But libido is a good friend of mine, and he comes around every few days. A few days past due on choking my chicken and I’m back in the same position I was several months ago. I text her that “the system’s backed up.” She knows what that means. Luckily, she’s in a good mood. We talk about the usual lightly dirty topics. Fetishes, preferences, insecurities and the like. I run out of time that day. She’s going to bed but I’m having the time of my life talking to her about these topics while I’m hard as a rock. I don’t jack off that night and as a consequence have a dream about her. I wake up early the next morning with a crazy idea.
I roll over and grab my phone and shoot her a text telling her I’ve got a crazy idea, but I’m open and comfortable enough with her to ask it. She of course has no problem with it. “Can I show you my stuff?” I feel a surge of excitement as I send it. Hopefully she’ll know what I mean. If she doesn’t get what I mean and I begin to feel guilty then I can still bail. It takes several hours before she can reply. Finally, in the afternoon, I see that she replied to my proposition. I’m excited and nervous. “Ya sure” she says. Wow. My heart starts pounding. “You know what I mean by ‘stuff’ right?” She does. And she has no problem with it. Talk about pitching a tent. I tell her how surprised and excited I am and that this is a fantasy for me. Turns out, her husband is out of town and she’s got the house to herself so it’ll be a quiet and boring evening. Perfect. She tells me to send them to her around eight that night.
Between about five in the evening and eight that night (among the longest three hours I’ve ever experienced), I gather up nearly every picture I’ve ever taken of my dick. There’s about a dozen that I can scrounge up from the past couple of years. I wait patiently to hear from her just in case she’s had a change of heart. Finally she texts me. She’s ready.
After small talk about how nervous I am, she reassures me. “I’m not going to judge you. Nor am I in it for exploitation. I just want to give you confidence. As well as knowing that it’s a fantasy of yours.” From the start I wasn’t looking for a gain in confidence or feedback really. Sure, I have a few small insecurities, but overall I’ve been very proud of my cock. I think it looks quite good if I do say so myself. I’m in it purely for the rush. And what a rush it is. I sit there with the first picture loaded and ready to send. I know she’s looking at her phone waiting for me. My heart rate soars and I begin to get the shakes. My mouth runs dry. The hormones flowing through my body at this moment are quite unlike anything I’ve ever felt before. I finally hit send.
It takes forever for her to reply. Really, it’s only about ten seconds. But knowing that this is the woman I went through puberty jacking off to that’s now quite willingly looking at my penis…I’m high as a kite. Her response kicks in. “Dang boy! That’s not what I was expecting!” She likes it. Or at least I hope she does. She sends a few more of her thoughts to me. Not only is she impressed, but it seems that she really does like it. I keep sending one after the other. She mentions how her face showed her surprise when she saw the first picture and even more so on the following ones. I only wish I could have been there to see it. I admit, I’m getting a little carried away now. I was only planning on sending a few of the best ones, but now that she seems to be enjoying it I send her everything I can find. This is going down as one of the best sexual experiences I’ve had. It seems so taboo that the excitement drawn from it is intensified several times over. The night ends with her mentioning how perhaps she’s willing to be with another man as part of experimentation in the bedroom. She adds, “you’re not a little boy anymore.”
A few weeks go by. I have a few haircuts over this span of time and nothing has been awkward or different between us. It’s just our little secret. By now, I’m even more comfortable with her than ever before. One day while I’m quite horny I take a second to whip out my dick and send her a picture. “You haven’t had lunch yet have you?” I joke. She knows what I mean. More and more lately I’ve been daydreaming about what it would be like with her lips wrapped around my cock. Slowly sucking the cum right out of me while I sit there watching something I can’t believe. The thought crosses my mind: how far is it until I hit the limit? Would she be willing to see it in person? Maybe grab a handful just to see how it throbs for her? Could more of my fantasies possibly become a reality?
Today’s my next haircut. I’m usually her last client. Sometimes there’s nobody else in the salon, but most times there’s another woman or two there still finishing their work for the day. I get a text from her asking if I can come in a few minutes later because she’s running behind. I can’t help but think about my daydreams of what that would lead to.
I show up at the shop. The parking lot is pretty empty. That’s a good sign. I go inside and sure enough, she’s the only one there. Things go on as they usually do while she’s cutting my hair. The conversation is the normal stuff we talk about. Once done, we continue talking like we do during every other appointment. She’s busy sweeping up and getting things ready for the next day. She locks the door and goes to the room in the back of the shop to do the remaining laundry. I sit quietly spinning in the chair as I usually do while she’s out of range for conversation. After a minute she calls to me from the back room. I walk to the back of the shop and around the corner. She wants me to get some laundry detergent from the top shelf. So much for that daydream. I get it for her and turn back towards the entrance of the room. She’s propped up in the door frame with her arms crossed, standing there looking at me. “Do you want to show me?” she asks. My heart sinks for a split second before the adrenaline hits my system. “Hmm?” is all I can manage as a response. “You mentioned showing it to me. Do you want to?” She glances down towards my waistline and back up at me. It seems like she’s doing it more for me to get arousal out of it. The way she’s asking is like she can take it or leave it, it doesn’t matter to her one way or the other. In most situations, I just can’t bring myself to act when the time comes. But this time…
I’m shaking already. When she asked and glanced down towards my crotch, I went half-mast immediately. I want to say no and avoid any guilt that might surely catch me later. But with her…I’m unsure. A desire within me is overriding that initial rejection. It’s wrong, but not wrong at the same time. It’s just showing her, right? I mean, if I had a medical emergency or wanted her to check some problem down there, she’d probably do it and it wouldn’t be seen as wrong. Right? The debate flying through my head in a split second is insane. “Uh…sure.” I’m following my boner on this one. Usually not a smart idea, but let’s see what happens. She walks in and pushes the door shut, then comes over and pulls a chair over by me. This feels like some sort of examination. I’m feeling like I’m being put on the spot. At the same time, I’m comfortable with her. If she’s gonna look, I want her to get a good one.
I unzip and slowly pull my jeans and boxers down. As I pull them low enough, my dick pops out like a jack in the box. It bobs up and down a few times as I stand up straight. I look at her and quickly look away. I can feel the embarrassment on my face. She’s looking at it from maybe two feet away and hasn’t taken her eyes off of it yet. After a second, she reaches towards it and looks at me, giving a “may I approach” look. I look at her, down at it, then back at her and give a little shrug. She grabs it.
I may have been a little more than half-mast up to this point, but the second she wrapped her hand around me I went full on rock hard. I can feel it start to throb in her hand. The rush inside my brain hits me so fast I almost feel light-headed. “It’s very nice. You should be proud of it.” she says. “I’m sure it’s quite enjoyable.” “Thanks,” I say nervously, “it gets the job done for me.” She’s still holding it. “…very enjoyable.” she adds. She strokes it a couple of times. I almost finished right then, but luckily managed to hold back my excitement. “Of course, this stays between us.” she says, giving me a look. “Well yeah…” I shrug. She keeps staring at me for a second with my cock in her hand. It’s almost as if she’s deciding something. She licks her lips.
The feeling of her warm, wet mouth sliding down the shaft of my cock is extraordinary. Years of fantasies, a sudden shock from the unexpected, and the overall warmth and feeling of her mouth suddenly traveling down my rod all culminate into a once-in-a-lifetime explosion of utter thrill and satisfaction. She slides down to the base, then backs out and looks up at me. “You OK?” she asks. I nod like some shocked schoolboy who just saw boob for the first time. She continues sucking on my cock, reaching up and grabbing my balls while she does. This is the epitome of pleasure. I feel myself relax and just focus on her and the feelings she’s giving me. I watch her lips move back and forth, gliding over my now wet and slippery penis. She moves slow, allowing both of us to savor the moment. Everything fades away. The world and all of it’s thoughts and problems are waiting on the other side of the door to this room. But inside the room: bliss. I’m not sure if she wore darker lipstick for the occasion of if she’s always worn that color. Regardless, it really amplifies the visual effect of her soft lips gliding over the surface of my vein-filled shaft. It’s quite red at this point. I feel years of desire building up within me. After a few minutes of her slow sucking, I can’t resist the build up. I jerk as my cock throbs in her mouth and mutter “I’m-” and that’s all I can manage. Screw it, she’ll figure it out. I hold back for as long as I can, tightening every muscle I can find within me to keep the floodgates from opening. I try to pull away from her but she stays right with me as I move. The dam bursts.
I explode straight into her mouth. She continues to slowly rock back and forth. I shoot more of my juices into her mouth. The second shot is the biggest. I can feel it traveling up from my balls, down my shaft and to the head before busting the doors down to get out. She sucks hard from the base to the head as this happens, resulting in her pulling the semen right out me. I jerk as I shoot it hard into her mouth. She gives a quick “Mm!” in shock. As she continues to suck, she lets some of the cum come out of her mouth and around my cock. She pulls away and rubs her lips on the head of my cock as it shoots more cum onto her mouth and over her face. I’ve only ever had loads this big once or twice up to this point in my life. I nearly cover her face in the stuff. It stops spurting and she grabs it to squeeze out what’s left onto her tongue. Then she gives it an extra suck or two, pulling out any remnants that may lay deep inside my balls. She looks up and lays my still throbbing cock on her cum-soaked face. It’s everywhere. She smiles with her eyes closed. The image of her sitting there covered in my cum, my cock laying across her face, with her eyes closed and a big smile while she soaks it all in is one I’ll never forget. She eventually moves away, but comes back one more time to give my shaft a kiss. The fantasies were nowhere near as good as the real thing. “Our little secret” she says, giving me a look.
–I write this while hard and daydreaming. Some of this has happened, the rest is part of the fantasies that take place regularly. What could make this even more arousing than putting it into words? Maybe I’ll tell her to read it. Maybe putting it into words and having her read it will be like a way for us to symbolically do exactly what’s written. Maybe, just maybe, that was the plan from the start.
Source: reddit.com/r/eroticliterature/comments/5reaem/mf_the_hairdresser_milf_xpost_rsexystories