This is a true story. It isn't really a missed opportunity, but an example of one of the times in my life when a woman inexplicably figured out I had a strong interest in haircutting despite my continuous efforts at making sure no one ever knew that about me.
When I was in my mid-twenties I worked in an office. There were several women near my age in the office, and a couple of them were single and attractive. I was becoming rather interested in one of them (her name was Teresa), and I thought she was feeling the same. Neither of us had done anything overt, limiting ourselves to simply being friendly while at work.
The other attractive woman (whose name was Megan) in the office seemed to be interested in me, though I was not really into her. She was a single mom and had three kids by three different fathers, and had never been married, and I just didn't want to get involved in that situation. But, as luck would have it, she was much more forward in her flirtations than the woman I was actually interested in. Maybe Megan knew or sensed that I was interested in Teresa instead of her, and she decided to try harder to win my attention out of jealousy.
Over the course of several weeks Megan had dropped a number of hints that she would like me to ask her out, always letting me know that she had no plans for a Friday or a Saturday night, or letting me know that her kids would be visiting her mother and she would be home all alone that night. She also did things like make cookies and brownies to put in the break room, but would always take a few out on a separate plate and put them on my desk for me. I was always nice to her but I didn't do anything that would indicate I was interested in seeing her outside of work, because I really didn't want to get involved in her home situation, and also because I was still hoping I could get Teresa to go out with me.
One Friday afternoon the only people working in the office were me, Megan, and the office manager. The officer manager left at four, which left me and Megan alone in the office for an hour. Our desks were within ten feet of each other and we chatted amicably as we worked. She had already mentioned through the day that her kids were being picked up at day care by her mother and that she'd have the house to herself that night, but as usual I hadn't done anything to indicate I was interested in coming over. As the afternoon wore on she made a few comments about how tight money was for her lately, but I didn't think anything of it until she specifically mentioned how expensive it was for her to go to the salon to get her hair cut. I don't think I showed any outward reaction to her comments but maybe I did and she picked up on it. I think she must have already had some idea that I was interested in hair to have brought the subject up at all, even though I was sure I had done nothing over the months I had worked there to indicate to anyone, ever, that I had any sort of unusual interest in hair or haircutting. But maybe I wasn't as inscrutable as I thought.
Megan was an attractive woman, with a rather unremarkable face but a very nice, slim, athletic body. I knew she did aerobics at the gym every morning before work, and it showed. Her hair was light brown, not terribly thick, and a few inches past her shoulders, with a side part and long bangs she wore swept to one side.
After mentioning how expensive it was to get her hair cut in a salon (and maybe after assessing my reaction to her comments) Megan began talking about how she had been thinking of changing her hairstyle. She said she was considering getting a blunt bob, about mid-neck level, which she said she thought she'd look good with. She also said that the best thing about a straight bob was that she could have a friend cut it for her, since all that was needed was to cut in a straight line. That way she could save money by not having to go to the salon.
Despite not wanting to get involved with Megan because of her home situation, I was getting very, very turned on by this conversation. Still, I was trying desperately to act as though none of this was very interesting, and I thought I was being very nonchalant about the whole thing. Maybe I wasn't being as cool as I thought, because Megan kept on going.
Megan said she'd watched as other women got bobs in the salon, and she knew just how to do it. She said you just sectioned off the hair, combed it straight down, and cut in a straight line. She said it was so simple anyone could do it, even if they'd never cut hair before in their life. As she talked she was running her fingers through her hair like she was sectioning it off, and then she was using her fingers like scissors to pantomime cutting it. I was probably staring intently at her by that point and she could probably tell I was getting very turned on. I knew I wasn't able to stand up from my desk because there wouldn't be any way to hide my erection if I did.
Acting as if the thought just occurred to her, Megan asked if I would be willing to do her a favor and cut her hair for her. She told me she would really appreciate it and if I was willing to come to her house after work to cut her hair she'd thank me by making me a nice dinner. I probably stared blankly at her for a few seconds before mumbling something about how I probably shouldn't because I'd screw it up. She smiled and told me it didn't have to be perfect, and anyway it was so easy she was sure I'd do it just fine.
I very much wanted to say yes, but I was mortified by the thought of everyone in the office noticing her new haircut on Monday and Megan telling everyone I had done it. If that happened I was sure everyone would think I was some sort of freak. Plus, I really didn't want to get involved with Megan because of her home situation, since in my mid-twenties the thought of dating a woman with three children scared the crap out of me. I told her again that I would probably screw it up and I didn't want to ruin her hair.
I must have been doing a lousy job hiding how turned on I was, because Megan definitely seemed to sense my resolve was weakening. She kept smiling and told me that I was sweet to worry about that, but it really was the simplest thing. Then without getting up she rolled her office chair around her desk and rolled it toward me. While sitting in the chair she turned it around so she was facing away from me and then she scooted it back the last couple of feet so the back of the chair was almost right up against the left side of my chair. She reached her arms up and gathered up her hair in a ponytail, then sectioned off from ear to ear horizontally with her fingernail, letting that section hang loose.
"We'll do a dry run, so to speak," she said, looking back over her shoulder for a moment and smiling at me. She faced forward again and said, "Just imagine we're at my house and you have my scissors in your hand. All you'd have to do is cut a straight line right in the middle of my neck. Piece of cake."
I didn't move or say a word for a few seconds, because I was torn between wanting to jump at the chance to cut her hair that night and not wanting to take the chance that everyone I worked with would find out I had an unusual interest in cutting hair. I was dying to do it but at the same time I was pretty much terrified of letting anyone know how turned on haircutting made me. I was so torn I was frozen.
Megan looked over her shoulder again, smiling, and then faced forward and told me not to be nervous. She told me to go ahead and use my fingers to pretend I was cutting a straight line at the middle of her neck. I hesitated again and she urged me to go ahead, laughing a little and saying there's no way I could be worried about screwing up her hair when I didn't even have scissors in my hand.
Pretty much overwhelmed at this point, I reached up and started to indulge my fantasy, just a little. I began to play with the section of hair that was hanging down, and I said that if I cut it at the middle of her neck she'd be losing about six or seven inches of hair. Just saying that turned me on even more, if that was possible. Megan said that was alright, she was okay with going shorter to save money.
I kept playing with her hair, running my fingers though it and imagining how great it would be to actually be able to cut it. After a few seconds, Megan let go of part of the ponytail she was holding on top of her head, and then used her fingernail to mark off another section and let that hair spill down into my hands. She said that all I'd have to do is cut a section at a time in a straight line, and that it would be so easy I wouldn't believe afterwards that I had worried about screwing it up. After another moment or two she let go of the ponytail completely and tilted her head back a bit as she spoke, letting her hair dangle down her back as I played with it.
We probably sat there for close to ten minutes, with her telling me how easy it would be and how she'd seen it done a million times in the salon, and all the while with her facing forward as I ran my fingers through her hair over and over again. She told me a few times how good it felt to have me play with her hair, and how I must be a natural and would no doubt do a great job on her haircut.
Unfortunately, even though I should have been having the time of my life, the whole time I was playing with her hair I was thinking that I shouldn't be doing this. I was thinking that if I actually went through with cutting her hair then she would know I had a hair fetish, and soon afterward the whole office would know I had a hair fetish. I also knew that if I went to her house to cut her hair I would probably wind up having sex with her, and I really didn't want to get involved with her in that way. I tried to convince myself to just go to her house, cut her hair, have sex with her, and then dump her, but using her like that when I knew I didn't want any kind of a relationship simply wasn't my style.
By that time it was nearly time to leave work, and I abruptly stopped playing with her hair and told her I really didn't think it was a good idea. She seemed surprised and said she thought I had gotten comfortable with the idea, but I gently told her I wasn't comfortable with it and I didn't want to do anything to mess her up. I was really trying to tell her that I didn't want to date her and that if I didn't want to date her I didn't think it was right of me to lead her on by going to her house that night. She seemed to get the message and although she was disappointed she seemed okay with it.
I later learned that Megan and Teresa hated each other for some reason having to do with a guy they had both dated a few years earlier. I'm sure that factored into her efforts to get me interested in her when she knew I was interested in Teresa. Still, I don't know how she as able to be so dead-on accurate with regards to how excited I would get with her haircutting gambit. I always thought I was very cool and that I never did anything to reveal my haircutting fetish to anyone, but apparently I wasn't as smooth as I thought I was. There have been maybe a half-dozen times in my life when a girl seemed to figure out I had an unusual interest in haircutting despite my perception that I never did a single thing to broadcast that interest to anyone.
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