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A Haircut To Remember

I am a 40 year old married man and father of 2 children. I’ve been married for 13 years and have always been faithful to my wife. For the past 10 years I have gotten a monthly haircut from the same woman, Jenn. When she first started cutting my hair she worked in a salon in the town we live in. She was 22 and single, I was 30 and had been married for 3 years. My wife and I had one child at the time, now we have 2. I was attracted to Jenn from the first time I saw her. She’s about 5’ 7’ with long blonde hair, blue eyes and a very nice body. Over the years I sat in her chair while she cut my hair with a hard on hidden underneath the smock. She has always been talkative and friendly with me and I know a lot about her and her life from our monthly conversations over the years.

8 years ago she got married. She had 2 children in a 3 year span after she got married and she put on some weight that didn’t come off right away. After her 2nd child was born she cut her hair real short and at some point she started wearing glasses. She went from being a real knock out to looking like a frumpy, middle aged school teacher. She still cut my hair and we still talked about everything under the sun but my sexual attraction to her more or less disappeared. It always amazed me how someone who was once such a hottie could let herself go like that. But in the long run it really didn’t matter because I was happily married and Jenn was still a real sweetheart. Besides, she did a really good job with my hair.

About a year or so ago she began a transformation back into the hot babe she had once been. She was letting her hair grow long again, she got contacts and she was working out at the gym and dieting. Each month when I went in to get a haircut I was more and more surprised and how good she was looking. I commented to her often that she was getting better with age and she said the same about me. My hair is starting to get a little salt and pepper as more and more gray creeps in and she always tells me how distinguished and handsome it makes me. I figured she was just being nice and trying to help keep my spirits up as I was getting grayer.

A few months ago while she was cutting my hair we were talking as usual. We got on the subject of her weight loss and newly acquired overall appearance because she had been dressing more and more sexy as she was losing weight. I joked with her that she was becoming a MILF. She didn’t know what a MILF was and tried to get me to explain. I told her to go home and type MILF in Google and find out for herself. She told me she would do that.

The next month when she was cutting my hair she told me that she was leaving that salon after 10 years and opening her own salon near by. She asked me if I would be interested in being a customer of hers at her new place and I assured her that I would follow her anywhere. Most of the conversation that day was about her new place and her plans for it. When she was done with my hair she walked with me to the front as she always does. She handed me a business card from her salon so I could call and make an appointment. Just before we got to the counter for me to pay she whispered, “Do you really think I’m a MILF?” I was surprised that she asked me that and I couldn’t help but laugh as I felt my face get a little hot. “So, you looked it up, huh?” I asked, smiling. “Yes, I did!” She said, as if she was proud of herself. My face got hotter. “Is that what you think I am?” She asked. “Well, you certainly qualify, yes.” I said. “Well, I’m honored that you think of me that way.” She said, smiling. By that time we were at the counter around other people and that was the end of the conversation. I paid for my hair cut and left.

The next month she cut my hair at her very own salon. It was a Saturday afternoon and the place was crowded. She had a couple of other ladies working with her and they were all booked solid for the day. Jenn was working on a hair coloring for an older lady and I could tell she was in a rush to get through with me because the lady was sitting in a chair in the back room with foil in her hair. The room we were in was small, crowded and loud and we really didn’t have much conversation. She had to leave to go check on the color job several times while she was cutting my hair. When she was done she apologized for having to rush and told me that she hated to miss out on our monthly chat. I assured her that it was fine and congratulated her on her apparent success with her new salon. She told me that in the future I should make appointments during the week late in the day or in the early evening. She said it would be quieter at those times. She said that she takes her last appointment at 7 PM and if I made an appointment at 7 then I’d likely get her all to myself. I told her I’d keep that in mind.

Last week I went in for my monthly hair cut. This time I had made an appointment for 7 PM on Wednesday night. When I got there, right at 7, Jenn and another lady that works with her were the only 2 people in the salon. The other lady was sweeping up and as Jenn washed my hair in the back room the lady came and told Jenn she was leaving for the night. Jenn told her to lock up on her way out since I was the last appointment for the day. The lady said she would and left. I was laying back in a reclining chair with my neck resting in the curved cut out of the sink. It was hurting my neck and I commented that my neck and back were sore from having helped a buddy move some furniture the day before. Jenn was just finishing rinsing conditioner out of my hair and raised my head up off the sink. She held one hand against the back of my head and with the other she started massaging my neck. She was moving her hand up and down the length of my neck as she applied pressure and it felt really good. I couldn’t help but think of her running her hand up and down my cock that way and I felt my cock stirring inside my jeans. She didn’t say anything and acted as if this was just part of the normal routine.

After a minute I joking said, “I’d pay you $20 extra to rub my back like that.” She laughed and said, “I might take you up on that, I can always use the money.” I laughed and said, “In that case I’ll pay you $50 extra to rub my entire body like that.” She laughed again and said, “If you want me to rub your back you need to take off your shirt.” I wasn’t sure if we were just kidding around or not and I wasn’t sure if I should really take off my shirt. Instead I said, “Does that mean I’ll have to take off everything if you take me up on my other offer?” Again she laughed and said, “Hmm… I’d have to think about that.” Then immediately she said, “Yep!” I laughed and said, “You didn’t think long.” She laughed again and said, “I don’t have a problem with naked men. But I bet you have a problem being naked in front of your hairdresser.” Suddenly I was feeling very awkward. I had never even flirted with another woman since I had been married and I wasn’t even sure if we were flirting or just playing around. Jenn is married and as far as I know happily married. I sat up in the chair and she kept her hand on my neck. When I was sitting up completely she moved her hands onto my shoulders and began massaging them. She said, “Wow, you’re either really tense our you are really strong because your muscles are really tight.” It was a combination of both. I am in great shape physically. I work out a couple of time a week at the gym and I swim regularly. I have an athletic build. I’m 6’1”, 185 pounds. A swimmer’s build. I have good muscle definition and six pack abs. I was more than willing to take off my shirt and everything else if I believed for a moment that she was serious. The problem was, I didn’t believe she was serious at all. And I didn’t want to run the risk of damaging our friendship by going too far with her.

“You know what you should do?” She asked, as she continued to massage my shoulders. “What’s that?” I asked. “You should sit in the massage chair. Naked!” She laughed. “What massage chair?” I asked. “Right over there,” she pointed across the room. I looked and there was a big black chair with weird looking leg holsters at the base. I had seen the chair but not paid any attention to it. But now that I was looking at it closely I realized it was one of those massage chairs that I had seen at the mall. “I didn’t even notice that,” I said. “It’s great,” she said. “It works wonders. I do it all the time at the end of the day.” “Do you sit in it naked?” I asked, teasingly. “When I’m here alone I do,” she said. “Really?” I asked, imaging her naked body sprawled out in that chair. “Oh, yes!” She said. “It’s pretty intense in certain places.” She walked in front of me and grabbed my hand pulling me out of the chair. “Come on,” she said. “Give it a try.”

I got up and let her lead me across the room. I could feel her warm hand against mine and I realized that was the first time I had ever touched her skin. That only helped increase the sensation I was feeling inside my jeans as my cock was growing by the second. As we got to the chair she squeezed my hand and said, “Ok, take of your clothes.” I laughed and said, “You’re joking, right?” She said, “No, I’m serious. It’s awesome naked!” I said, “Maybe for you, but I’m built different. It may not have the same affect on me.” She said, “I bet it does,” and she grabbed my t-shirt and started to pull it up over my head. I was embarrassed at the thought of her seeing me without a shirt on even though I know I look good without a shirt. But the situation was awkward for me for some reason. I wasn’t sure how far she would go, how far I would go or how far I even wanted it to go. All I knew was that she was turning me on and part of me wanted to let her see my naked body and my growing cock. When I am fully erect I am about 8” long and pretty thick, too. I’m proud of my naked body. Especially when my cock is hanging low, semi erect like it was then.

I let her pull my shirt over my head and she tossed it into an empty chair. She said, “Now the shoes and pants. You can leave your boxers or briefs, whichever you wear on if you’re too scared to let me see you naked.” She laughed as she said that. I kicked off my sandals and said, “Neither. I’m commando.” She giggled and said, “Even better! Now I get to see you naked because your pants are definitely coming off!” With that she reached for the top button on my jeans and started undoing it. I really expected her to stop and tell me that it had gone far enough and fun time was over but she didn’t. She unbuttoned my pants and began to unzip them. I stood in front of her with my cock getting harder. She started pushing my jeans down off my waist as if this was just routine. As the jeans went lower the length of my cock was revealed to her. “Mmm… Nice!” She said as my jeans fell down around my ankles. I wanted badly for her to reach and grab my cock but instead she patted the chair and told me to take a seat. I stepped out of my jeans and sat in the chair.

It felt like I was sitting on ice cubes. I let out a little moan as the cold leather made contact with my ass, balls and back. She laughed and said, “Oops! I should of turned the heat on first. Sorry.” She grabbed a remote control that was attached to one of the arms and pushed some buttons. The chair started vibrating all around me and within a few seconds I could feel the heat on my ass from the internal heaters. She moved in front of me, between my legs and extended the 2 leg rests. They were designed to go partly around your legs to massage your calf muscles. As she extended them upward from the floor she also extended them outward away from the middle. I could tell right away that in order for me to put my legs in the there I was going to have to spread them wide. “This will give me a better view,” she said giggling. She lifted each of my legs and placed them on the leg rests and pushed the flexible sides up to better hug my calves. The feeling was, as she said, intense. The thought of Jenn seeing me naked like that combined with the vibrating sensations throughout my body felt really, really good. The chair was getting warmer now from the heaters and I could really feel that heat against my balls, my ass and the head of my cock as it lay on the chair between my legs.

She grabbed the remote and pushed some buttons and the vibrations turned to what felt like little steel balls rolling all over my back and on my ass and legs. At first it kind of hurt on my back where the balls were rolling across my spine but I adjusted in the chair a little and it was ok after that. The balls rolling against my ass and under my balls was a different story. That felt really intense and my cock was responding by starting to rise up off the chair. Jenn said, “That’s my favorite setting. I can have an orgasm with those balls rolling all over me.” The thought that Jenn had sat naked in that same chair and had an orgasm made me moan out loud. “Do you think you can have one sitting there?” She asked matter of factly. She caught me off guard with that question but I managed to answer her as calmly as I could. “Probably not,” I said. “I bet you can!” She said, and walked over to the counter nearest the chair. She grabbed a bottle from the counter and came back to me as she was opening the top of it. I could see that it was some sort of lotion and she squeezed some into her hand. “Close your eyes,” she ordered. I laid my head back and closed my eyes. I was beginning to wonder if she was going to put the lotion on my face but then I felt her oily hands on my inner thighs, ever so close to my cock. The lotion on her hands was cold and it sent a chill through me that made my cock jump a little. “Ooo..!” She giggled. “I like that!”

I opened my eyes and looked down. Jenn was on her knees between my legs on the floor in front of me. She grabbed the bottle of lotion again and squirted some directly on my cock. The cold lotion made my cock jump again and again she giggled. I watched as she moved her hand on me and began rubbing the lotion into my cock. I could feel a slight tingle from the lotion and that only heightened my arousal. As soon as she touched my cock it became rigid and was now standing up pointing back at my face. She moaned and began to slowly work her slippery hand up and down the length of my cock. Her other hand began to massage my balls. I immediately felt as if I would blow my load all over her hand and my stomach. She continued to moan as she slowly pumped my cock. Occasionally she’d let her finger of her other hand brush against my ass hole. That sent shock waves through me every time she did it. She would move her other hand up and rub lotion into the head of my cock in a circular motion while her other hand continued to stroke me up and down slowly.

At one point she took my cock in her left hand and moved her right hand down between her legs. I heard her unzip her pants and I could tell that she had bushed her hand down inside the front of her pants. She began moaning loudly and I knew that she was playing with her pussy and clit. I wanted so badly to be able to do it for her but I was not in a position where I could reach her. I couldn’t even see her pussy. All I could see was her hand down the front of her pants. She moved her hand up out of her pants and I could see her middle 2 fingers were wet. Oh my god! What a sight! She rubbed the head of my cock with her wet fingers. She moved her fingers around in a circle over the head of my cock just like she had done with the lotion. She moved her hand back down to her pussy and after a few seconds she moved her wet fingers back to my cock. I was dying for her to take my cock in her mouth but she never did. She repeated the process a few more times and I was able to see her wet pussy juices on the head of my cock. After a few times of moving her wet fingers to my cock she moved them to her mouth and sucked her own juices from her fingers. That drove me insane. I said, “Let me taste!” She removed her fingers from her mouth and looked me in the eye for the first time since all this started and said, “No, I can’t. I’m a married woman.” At this point I thought she was just kidding about that part and I said, “So? We’ve gone this far. I really want to taste you. I want to please you.” She said, “This is all we can do. Just lay back and enjoy it. I’ll take care of myself.”

Being that my cock was rock hard and feeling as if it would explode at any minute I couldn’t put up much of an argument. She moved her hand back down between her legs and this time she was moving it faster. She was pumping my cock faster and faster and squeezing it very tight. She was moaning more and more and she said, breathlessly, “I want to watch you cum. Please cum for me!” That was all I needed to hear. I felt the orgasm building deep inside of me and suddenly I was erupting. I watched the first waves of my cum shoot out and land on her arm and on my belly. She continued to pump my cock in her hand as more and more cum shot out of me. After the first couple of spurts went high in the air it was more or less pouring out of me, down the side of my cock and over her hand. She just kept saying, “Yes! Yes! Cum for me!” Even after my orgasm ended she kept pumping my cock slowly. Her hand was still working feverishly on her pussy and clit and after a few seconds she lowered her head and squeezed my cock hard in her hand. Her back arched a little and she was shaking all over and grunting as she gave herself what appeared to be and intense orgasm. I watched as her back and hips bucked against her hand with each wave of her orgasm. After what seemed like a full minute or more she stopped bucking and became completely still. Her head was down and she was breathing hard. Her hand was still inside her pants and her other hand was still on my cock but she was not squeezing it or stroking it. Just holding it gently in her hand.

I was breathing hard, too. I sat there in amazement looking down at my cum covered belly and her cum covered hand. She slowly stood up and her hand was still down inside her pants. I could see the red lace panties she was wearing and the sexy belly button ring in her naval. She raised her cum soaked hand to her mouth and touched the very tip of her tongue to a spot where my cum was. She got a tiny little taste of my cum on the tip of her tongue and said, “Mmm…” “Hey!” I said, “That’s not fair! I didn’t get to taste you!” She smiled at me and moved her hand out of her panties and moved it towards my face. “Ok,” she said. “One taste, that’s all!” With that she put her wets fingers against my mouth. I quickly took her 2 middle fingers into my mouth and sucked her pussy juices from them. I looked her straight in the eyes as I did it, flicking my tongue around them, savoring every bit of her juices. She moaned and seemed to be melting as I did this and for a moment I thought I was going to be able to get her in the chair naked. But then she pulled her fingers away from me and said, “Ok, lets get cleaned up and get your hair cut. It’s getting late.” I protested and told her that I wanted to see her naked in the chair and return the favor. “Nope, playtime’s over,” she said as she tossed me a towel from the sink. She headed into the bathroom and I grabbed the remote and turned the chair off. I got up and went into the other bathroom and cleaned up then I got dressed. When I came out of the bathroom she was standing by the sink and she told me that she’d have to get my hair wet again before she cut it. “This time,” she said, “There will be no rubbing or massaging of any kind. Deal?” she said. “Deal!” I said, and sat down in the chair.

She quickly rinsed my hair to get it wet and then we were off to her chair so she could cut my hair. The silence between us was more awkward than the flirting had been earlier. After several minutes I finally spoke, “Are we not even going to talk about what happened?” I asked. She seemed a little embarrassed and wouldn’t even look up at the mirror to make eye contact with me. “No, I prefer we didn’t talk about it,” she said. “And just so you know,” she added, “there are no extra charges involved with your visit.” “Oh, really?” That was a freebie?” I asked jokingly. “I’m not a prostitute!” She said, seeming as if she was mad. “I never said you were, Jenn.” I said, apologetically. “Good!” she snapped. Suddenly I was aware that perhaps I had done what I didn’t want to do and had harmed our friendship. I felt terrible. “Jenn, I’m sorry,” I said. “I shouldn’t have joked around with you about the massage like I did.” “No need to be sorry,” she said. “I’m a big girl, I knew what I was doing. I just don’t want you thinking I do that sort of thing all the time. I’ve never done anything like that in my life with anyone other than my husband.” “I don’t think that at all,” I said. “In fact,” she continued, “I’ve never even done that with him. All we ever do is have quickie sex when he wants it and it’s always wham-bam-thank-you-ma’am sex.” “Well, all I can say is that I enjoyed the massage chair very much,” I said. “And to be honest, I have always had a fantasy about you.” She smiled a little when I said that and she said, “I’m glad I could make one of your fantasies come true and I trust that you will never speak a word about this to anyone.” I said, “You have my word. I’ll never tell another soul what happened.”

With that she was finished with my hair. I told her there was no need to blow it dry and I got up from the chair. We walked to the front so I could pay her and I gave her 2 twenty dollar bills for a $20 haircut. She said, “It’s only $20.” I said, “I know, the other twenty is a tip.” She seemed hurt again and said, “I told you, I am not a prostitute!” I said, “No, you’re an awesome hair stylist who just gave me the best haircut I’ve ever had and I’m tipping you.” She seemed reluctant to take the extra money and I said, “Well, I wanted to tip you in another way but you wouldn’t let me, so just take the tip and say thank you.” She smiled and said, “I would have felt better letting you tip me the other way.” I laughed and said, “I’m sure you would have. It’s not too late if you want me to tip you another way.” She smiled again and said, “No, I’ll take the twenty.” I laughed and offered again but she politely declined. I told her that I liked Wednesday nights at 7 PM and that I would come at the same time on my next visit. She said that was fine with her, too. I offered to hang around while she closed up shop but she told me she had some paper work to do and would be there a while. I headed for the door and told her I would see her next month. She came over to unlock the door to let me out and as I was going out the door she said, “Hey… Have you really had fantasies about me?” “Oh, yes!” I said, “Lots of them.” She smiled and said, “Good, cause I’ve had fantasies about you, too. Lots of them!” “Really?” I asked, genuinely shocked. “Yep,” she said. “Maybe I will tell you about them next time.” “I’ll look forward to it,” I said. “Me, too,” she replied. “Too bad my hair doesn’t grow faster,” I joked and we both laughed. “Yes,” she agreed. “Too bad. But 4 weeks gives us plenty of time to think about the next time, I guess.” I smiled at her and headed to my car sporting the best haircut I have ever had. At least for another 3 weeks or so.

End of Story