Four Girlfriends: Part 1


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For as long as I can remember, seeing a woman’s long hair cut has been exhilarating. Naturally, whenever I was in a relationship, it became a goal to get my girlfriend’s hair cut. This story is completely true, and it is the first in a four-part series (all true) about four girlfriends I have had and my experiences trying (and succeeding) in getting their hair cut.

My first girlfriend was a girl by the name of Catherine. Catherine was a lovely girl, a bit shy, but about 5’7”, brown eyes, and a little tomboyish, but what originally caught my attention was her hair. Long, smooth, not too thick or thin, and the most gorgeous shade of light brown you hand ever seen, cascading all the way down to her hips. It was our sophomore year of high school, and we had some classes together for the first time, which is how I got a chance to approach her, and then was lucky enough to start dating her.

We had been dating for about three months when she brought up her hair for the first time. We were laying on the couch, watching a movie, and I was running my hands through her hair, as I always would. Catherine said to me, “God, sometimes I wish that I could just cut my hair off. It drives me crazy.” Being new at the whole “boyfriend” thing, I was hesitant to expose too much of my dream, especially since she thought I loved her long hair, given that I would play with it so often (Of course, I did love her long hair, but I just loved the idea of cutting her hair even more).

Finally, I mustered up the courage to say, “Well if you want to cut your hair, I think you should do it. I bet it would look cute on you.”

Catherine blushed, but then quickly stated, “I’ve tried before, but my mother hates the idea of me with short hair. She won’t allow it.”

Knowing her mother and the strained relationship that they had, I knew I would get nowhere, since Catherine didn’t want to make things any worse. Still, over the next couple months, Catherine kept complaining about her hair. Whether it were a text about her hair getting tangled in the wind, a knot in her hair while she was brushing it, or getting it caught in her coat zipper, she more and more frequently brought up how much she wanted her hair cut. And every now and then, I would encourage her towards rebelling against her mother’s wishes.

One night, Catherine sent me a text that read, “I’m done with this. I’m going downstairs and demanding from my mother that I get my hair cut off.” The bond had finally snapped. I wished her luck and hoped to get a nice surprise. Boy, did I ever.

After about a half an hour, Catherine texted me again, saying, “My mother isn’t happy about it, but she says I can get my hair cut, as long as I don’t go somewhere to pay for it. She finds that a waste of money. What should I do?”

I could hardly contain myself. I gave several options, but I heavily hinted that she come over and I do it for her. If it wasn’t perfect, she wouldn’t mind; she was never one to be too concerned with her appearances, and besides, I think at this point she had a pretty good idea that I liked the idea of cutting her hair, because she jumped all over that idea. “Be over in 10 minutes,” she said, “Have scissors ready.”

When she got to my house, I greeted Catherine with a passionate kiss. She smiled, and said, “I can’t wait to see what happens afterward if you’re this excited now.”

I offered her a chair, and when she was seated, I asked if she would take her shirt off. She was more than happy to oblige, and so it was just her in her bra seated before me. I couldn’t believe it-it seemed too good to be true. I held up a mirror and asked her how short she wanted me to cut her hair. I placed my hand at her collarbone, and she said that that was a good place to start. I brushed her long, gorgeous light brown hair one last time before getting the scissors. I put the mirror to the side-Catherine liked the idea of a surprise, and so did I. I opened the scissors and slid them under her hair just below her shoulders. Schink!—a piece of hair probably 16” long cascaded to the floor. I couldn’t contain myself and kissed Catherine again. She smiled from ear to ear, and then I continued cutting her hair that same shoulder length. I held up a mirror and she looked into it, adjusted a few things, but then didn’t say anything for what felt like forever. Then she turned around to me and said one word: “Shorter.”

She held up her hand to her jawline. I couldn’t believe it! I said boldly, “for it to look good this short, I need to grab some clippers for the back.” Catherine grinned and said that was fine. I ran and got some clippers from my bathroom and put them aside. First, I took her shoulder length hair and combed it out, and then I put the scissors directly on her jaw, right next to her chin, and then-snip! I cut all the way around her head. 6 more inches of hair cascaded to the floor into the pile. After that was done, I put a #2 guard on the clippers and sectioned off her hair to give her an undercut. Upon the first pass of the clippers up the back of her head, Catherine shuddered and melted into my arms. When I was done, I held up the mirror and she squealed with delight.

“My hair! It is short. Very much so!” And she gave me my favorite smile. She then told me to go sit on the couch, where she climbed on me and pushed me back against the couch, where she proceeded to make out with me in her sexy, rebellious, short new haircut.

The relationship ended a while later on mutual terms, no hard feelings, but Catherine gave me the thrill of my life, letting me realize my greatest fantasy…that is, I thought she did, until Sara entered my life.

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