Winning The Bet

Winning The Bet

Winning the Bet – Zirc

This is a true story of a bet that was made and fulfilled my dreams of erotic haircutting.

My lover and I had been seeing each other for a year. Her name is Kathy, she stands 5’4″ with golden brown hair that cascades over her shoulders and falls to the middle of her back. People have commented on her hair looking like Julia Roberts’ hair in the movie “Pretty Woman” only longer. Her hair has a year old perm that gives it gorgeous flowing curls and beautiful natural blonde highlights.

I was attracted to her because of her hair. When I first set my eyes on her my heart went thump! Whenever I look at women, I notice their hair before anything else. Kathy’s hair looked fabulous, framing her face and frolicking around her bosoms. When we started going out I would love to run my fingers through her hair when we made love. Letting it fall onto my chest and into my face.

We both lived about 3 hours away from our parents so we would offer drive with each other to see them. The drives would be long and boring so we started playing a road game of looking for words on signs that would start with all the letters of the alphabet. Starting with A through Z. The winner was the person who usually found a “work zone” sign before the other person. We made this game more intriguing when we starting setting up prizes. I would ask Kathy “what do you want if you win?”. We started with simple things like I would have to cook the dinner of her choice, or I would have to rub her feet for a half hour when we got home. I would request prizes like her letting me braid her hair or style her hair.

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The prizes started getting more intense. When I was asked I responded, “Well Kathy lets see, if I win, I want to trim your hair.” Kathy agreed because she needed a trim anyway and knew that I had my cosmetology license from years ago and felt confident in my abilities. Kathy hesitated, deep in thought, but responded with “OK, but if I win, I want to shave your chest”. WOW where did that come from? Hey, sounds like fun. “OK”.

Well, I lost on purpose! The drive was only part over so I asked to play double or nothing. She agreed. “OK, Kathy if I win I still want to cut your hair, only I want to cut it to the shoulders.” Kathy jerked like she was hit with something.

“I thought you liked my hair, I’ve never had it that short, I don’t know if I’d like it” I told her I did like her hair but if I was going to lose my chest hair, I should be able to get something in return. The tension in the air just quadrupled. All of a sudden, the game wasn’t just a game it was an erotic adventure.

After asking Kathy a couple more times, she reluctantly agreed but came back with that if she won, she got to shave my whole body from the neck down, not just my chest. I thought about it deeply for a half a second then agreed. (Heck I would win either way! An erotic adventure was guaranteed). The game started and it was more cut-throat than it ever was. There was no giving the benefit of the doubt anymore.

The second game ended a very close one. Kathy and I both were on Z when I spotted a falling rock zone sign first. I won! Kathy turned instantly quiet. Whenever we played we always had the rule that you never bet what you won’t do. We joke all the time about “no welching” on a bet. Kathy started asking me not to cut her hair. She really did not want 12 to 18 inches of her hair just lopped off. She took great pride in it.

I refused to back down, citing our promise of keeping every bet. Kathy jumped up with, “OK then… double or nothing, if I win you don’t cut my hair at all. What do you want if you win?” Well we still had enough time left for one more game so I agreed… but with a stipulation. “OK” I said “But if I win this one. I can cut your hair as short as I desire, any length I choose!”

Again, there was a long pause. Kathy couldn’t believe my request. It was obvious that her love for me dropped 300% at that point. She knew how close the last game was and knew she won the first game by a wide margin. (She won, with me still on ‘Q’, but remember I let her win that one!) She agreed, but before we started I asked her again, “Are you sure you want to do this, there’s no backing down if you lose….”

She accepted by saying, “I don’t want my hair cut at all but if you’re going to cut it to the shoulders I’m not going to like it anyway, so I might as well try to stop it from being cut at all.”

The game began and ended with a huge grin on my lips and a quivering lip on Kathy. We didn’t speak the rest of the trip. When we arrived home Kathy was very quiet, answering my questions with a quick, short answer. My stomach was doing flips every time I thought about my prize. Her hair was beautiful, but to be in control of cutting it all off against her will was too much to take, I could feel myself rock hard and waiting for relief.

I told her I would do the deed the following day since it was getting late and I wanted the anticipation to build to an ecstatic level. Besides, I needed to plan for it. I wanted everything to be perfect. She slept on the couch that night, refusing to sleep with me. That’s OK, my dream was coming true and she’d get over it, I guess. The next morning she was up before me with a cup of coffee poured for me and a muffin toasted and buttered. She smiled and gave me a kiss on the cheek. I told her how much I loved her when she put her arms around me and she said, “Honey, please don’t cut my hair, I know you love it as much as I do and I would do anything not to part with it.”

I wrapped my arms around her and said, “I love your hair too, but a bet’s a bet and today is the day. I’ll be as gentle as possible.” She pulled away and huffed into the living room, turning on the television.

I proceeded to collect my supplies and laid everything out on the dining room table. When I was ready I called her out. “Kathy, come on out, it’s time.” The air felt heavy and thick. I found myself almost gagging from trying to breathe in. My excitement and adrenaline was pumping intensely through my veins. I called her two more times, reminding her of our rules that we both agreed to. She stomped out in a huff and plopped down in the chair I had pulled out. I watched as she scanned the table top. Her eyes grew wide as she saw the spray bottle, hair cape, clips, combs, brush, scissors, clippers, shaving cream and three safety razors. Kathy stated loudly, “WHAT THE HELL ARE THOSE FOR?” I reminded her that our bet was that I could cut her hair to any length I chose and I intended to cut it however I decide! I saw tears start running down her cheek as she quietly muttered, “Please don’t honey, I really don’t want my hair cut”. I pretended not to hear it as I draped the cape around her sweet neck and fastened it around her nape. I slowly pulled her tresses out and let them fall atop the cape. Again I looked in awe of her gorgeous locks. Thick, flowing, shining waves of beauty.

I began brushing her hair out while Kathy’s head faced the floor. Crying a little more loudly so I would hear it. I brushed out her lovely locks for what seemed like hours. As I laid down the brush and picked up the shears, Kathy broke out into sobbing. I ignored it again as I placed the blades of the shears to her neck and waited. Again the cry faded to a quiet moan of Kathy saying over and over “please don’t, please don’t.” My hand was quivering and my head was spinning with anticipation as I gripped a huge section of hair at the base of her neck and closed the blades above my hand. SCHNICK SCHNICK, SCHNICK went the shears as her flowing hair which took years of growing and caring for, fell limp in my hand. Kathy stopped whimpering and fell limp in the chair as well. It was like she gave up all hope as she heard and felt the shears do their job.

I felt a huge burst of energy and continued cutting through the rest of Kathy’s mane that lay beyond her neck. Cutting around to the front of her hair I got no reaction from Kathy. I had to position her head up over and over again as it slowly slipped back down onto her chest. Her hair was finally all one length, above the shoulders, with shiny swatches laying everywhere. I’ve never seen so much unattached hair in my life. I wanted to stop and pick it up and fondle it, but I continued. I started pulling sections of hair 90 degrees from her head and cut it to about a three-inch length all over. My energy level made my heart pound out of its chest as I cut more and more. Finally I put down the shears when Kathy’s hair was cut in a kind of pixie cut / shag style.

Upon picking up the clippers I put on an attachment that would leave about 3/4 inch of hair left. I hesitated for a minute thinking if I had any sense of pride or feeling. It was like I was in a daze as I continued despite my thoughts, flicking them on. Kathy jumped, well maybe she didn’t pass out like I thought. As I placed them on her nape I expected Kathy to try to stop me. She didn’t even move, I guess she gave up all hope. Well, up came the clippers as it formed a spiky strip of mowed down hair through the middle of Kathy’s head. I continued bringing the clippers up the back, and up the sides until it had done the complete job. Kathys hair now looked like a military cut.

I continued by picking up the shaving cream and applying it liberally through her scalp. I heard a quiet sob again from Kathy as I stroked her head with the razor, over and over again till I made contact with every part of her scalp. Toweling it off I smiled because I purposely left the cap on the end of the razor so she would not be bald, just think she was. I kissed her on the cheek and began cleaning up. I handed her a mirror to see that she wasn’t bald but she didn’t look. She got up and walked out the door.

I’ve never seen Kathy since, but I’m sure we will remember the experience forever.

I still get hot when I look at my souvenir and start thinking about it.


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