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Back when I was at school, I had a bit of a crush on this girl. Her name was Alison and man did I have a thing for her. She used to hang around with me and a group of my friends, those were the days. We used to have so much fun together, jamming to music, chatting out the day, bitching about people. All in good fun of course and Alison was part of it all. You see we were all a bit punk/emoish back in the day so there was a lot of dark colours worn and metal listened too. In addition some of us had some pretty out there hairstyles too. Some of the guys had mohawks and all of the girls had some pretty awesome colours in theirs. I still remember the day when my friend Katie came into school with half of her head shaved I couldn’t keep my eyes off it, I had to constantly re- adjust myself when ever she was near. Still though she had nothing on Alison, She had bright blue hair at the time and a nose ring that really suited her, plus she was as cute as a button so she always looked amazing. For years I fantasised about being with her and yes some how never had the courage to ask her out. I mean you guys didn’t know how hot she was, even the jocks thought she was hot and a couple even tried it on, but were shot down like fighter planes. Was always funny seeing the other guys try to hit on her and crash and burn. Things went on like this for a while then at around about the start of the final year, we all rocked up to the usual spot and no Alison. Katie and the guys were all accounted for but she was nowhere to be seen. Then at lunch we saw her. She was blond had regular clothes and the noes ring was gone instead it was a little stud, then she sat with a group of girls and missed us entirely. My heart sank the girl that I had lusted over so much was now gone, she had changed from our little ways and started anew. Over the course of that year all of us changed too, I dated Kate, the guys dated the popular girls and the punk/emo days were over. However this didn’t stop Katie doing mad stuff with her hair still and its kind of where my fetish for hair started. She had an under-shave for ages then had a pixie cut then a cute red bob all in the space of a year. Then what really kicked off the fetish is when she asked me to join in. She wanted me to buzz under her bob so that the back and sides were shaved and the bob covered it. I didn’t know how to react I just seemed to go along with it as I loved her at the time. She took off every bit of clothing she had on and sat in my desk chair and smiling at me, waiting for her little haircut. I pushed her head down fired up the clippers and buzzed the parts she told me to buzz and it was heaven. I had never experienced anything like It, the rush of cutting someone’s hair. The power that I now had, it was increasable. I literally got so hard you would need an anchor to bring it back down again and Katie, well she rather liked it too. As the clippers went her hair sliding down her naked body all I wanted was to fuck her and when it was done, I picked her up, chucked her on the bed and fucked her so hard I nearly broke my bed in the process. After School had finished, Katie and I broke up as she was going to a different college and wanted to see other people. So this meant that I spent most of my summer alone, in a way. I spent that entire summer on my computer looking at haircutting and head-shaving videos, not healthy I know but I was hooked.

There was all those guys and girls out there pleasuring themselves to regular porn and there is me, knocking one out to the sight of a girl getting her head shaved. When I hit college though that’s when things changed and a blast from the past re-entered my life.

It was at a frat party that some guys were throwing, plenty of beer and chances to hook up while I was there though, I spotted someone that I never in a million years expected to see there. Alison. She came in on her own and started to mingle straight away with some people, I couldn’t be live it the girl that I had a chorus on for so long, was now back in my life. I thought that it must have been a gift from the gods or something. It wasn’t before long that she spotted me and came over. “Hey” she said in an oddly excited tone, she wrapped her arms around me and hugged away. “God I haven’t seen you in so long” she said as she released her grip, “yeah I know right its been 2 years I think” I replied as I slowly took a sip of my drink. “Hey the are doing a betting drinking game at the bar wanna go check it it out?” Alison asked, “sure” I replied as I finished my drink and walked over there with her. As we joined a girl was downing some random concoction at the bar, the crowd silent eager to see if she would be able to finish it. As the last gulp occurred the bar erupted as the last of her drink went down and her friend handed over 50 bucks. This went on for a while as more and more people took the challenge. It was all rather entertaining there was even a guy that puked on the girl that he was trying to seduce. Needless to say that It didn’t end well for the poor guy, as he was met with a swift kick in the balls and a wave good bye. Then as things started to slow down a bit, Alison decided to inject some life back into things. “This guy right here is gonna take up the challenge!” she shouted across the bar as he lifted up my arm. I didn’t really see how I would get out of this, so decided to play along and entered into the field of battle. The guy at the bar handed me a what I had to drink, It smelt foul and didn’t exactly look that appetising but I was here now. “So then blondie, what is the bet?” he asked. At that moment Alison rummaged through her pockets to try and see if she had any money, but turned up nothing. “come on there has got to be something” the guy said in a husky tone demanding his bet. There was a pause for a few more seconds as Alison made a decision, I looked at her and it was all most as if I could see cogs turning away. Then her answer came forth and it surprised even me. “My hair” she shouted “if he downs it he can do something with my hair”, at that moment I was instantly game. Here sitting in my lap was the golden opportunity, the girl of my dreams was telling me that I could do something with her hair and all I had to do, was drink the drink. This drink was going down and her hair is gonna be mine. Before the head guy even said if that was an ok bet, I grasped the glass tightly and started to down the liquid. The taste was extremely unpleasant I had no idea what was in it, but it seriously was not nice. More and more I chugged desperate to finish and clam my prize, as well as gain some bragging rights along with it. I finally chugged the last of the drink and slammed the glass back down on the side of the bar, challenge complete. The crowd erupted with cheer at the sight of my victory. Alison smiled and hugged me “well done” she said, as she wrapped her arms around me once more.

I accepted her embrace, my hand touching her hair wondering what I was now going to do with my prize.

The next day I told Alison to come up to my dorm room to for fill the bet. She arrived promptly with a slight spring step. “hey” she said in an oddly excited voice “ready to do this”, she slumped on my bed ready for her for fit. I could already tell just by looking at her that she was nervous, worried about what I may end up doing with her luscious blond locks. The over excited nature was just a mask for the fact that she now had to deal with the consequences of her actions. I got her to take a seat in my desk chair, then I took out the equipment that I would be using. I grabbed the cape, slowly draping it across her body and fastened it tightly around her neck, then I began to look for the rest of what I needed. As I Alison started to ask questions, trying to figure out what it was that I had planned for her. “so what are you going to do?” she asked, I simply said nothing as I found what I was looking for and placed them on the desk in front of her. The item in question, was a set of electric clippers. There was a moment of silence as Alison stared blankly at the clippers in front of her, then with unrelenting force she started shout. “Are you fucking kidding me!?” she shouted directly at me as I stood behind her. “I though you were going to dye my hair a crazy colour or maybe give my hair a trim something like that, not shave my head” she cried. Tears started to well in her eyes as I could tell that this was something that see really did not want to do. Frightened that she would chicken out and I would miss my opportunity i chimed in, “well you bet your hair and you said I could do something with it, do want people to think you chickened out?” I said. Alison once again went silent as she though about her predicament. “Ok” she said with a slight sigh “I bet my hair so I have to pay my debts”, I grabbed the clippers and turned them on. The sound of the buzzing clippers then filled the room as I double checked the guard, a grade 2. I placed them at the tip of her forehead and slowly pulled them back over her head, the blades slicing through the blond hair, causing it to fall straight to the floor. There were no tears only a little bit of laughter from Alison, trying to hide how worried and scared she really was. “I can’t believe that I am getting my hair shaved off by you” she said as she took some of the loose blond hair and threw it to the floor. I said nothing and continued the job at hand slowly moving the clippers over head as more of her hair slowly submitted, leaving a short blond pelt behind. “head to the right please” I called out in a dominating manner, Alison complied as she sniffled a little, the clippers then started to move along the left side of her head. I started to wonder, as now that the haircut had began Alison had not cried at all. There were some tears to begin with but as soon as the clippers got started there was nothing almost complete compliance. “head to the left please” I asked and once again Alison complied, leaning her head as the clippers ran along the side of her head. The clippers ran past the side and around of her ear, merciless in their quest to remove all of her long hair. Still their was no reaction Alison, she sat there as still as a mouse taking her forfeit well. I forced her head down and slowly started to run the clippers up the back of her neck, flicking the clippers back to toss the hair back onto the floor. More and more passes were made to remove the last of her Alison’s long hair, the clippers being relentless in their task. I ran them over her head one last time to get every last hair, then I turned off the clippers and removed the cape. More of Alison’s blonde hair fell to the floor as she stood up and walked straight into the bathroom, desperate to see her new look. “Oh my god” she said as she saw herself in the mirror “I look like im about to join the army”, a few tears appeared in her eyes. She slowly raised a hand and started to run it over her head exploring her head, some tears hit the sink as the reality of it all hit home. “you can take a shower to wash off the last of the hair” I said as I turned it on for her, she hugged me once again and wiped her eyes again still with tears filling them. While Alison showered, I cleaned up and made a small pony tail and placed it in a draw then put the rest In a little bag to do with what ever she wanted. I then sat back on my bed feeling over the moon at what at just happened, I shaved Alison. Finally doing something I had always wanted, to the girl I had always wanted and it felt so good. In a way I though she kinda deserved it for ditching us all that time ago and now she got her punishment for leaving. My eyes were firmly locked on my laptop as the bathroom door swung open, then I was disturbed by the sound of Alison’s voice. “Do I look hot to you?” she asked, as I looked up their she was completely naked. My jaw hit the floor as she looked absolutely stunning, “you have no idea” I replied. She then came over and started to take off my clothes, “time for me to pay the barber for such a good job” she said as she took off my jeans and tossed them onto the floor. As she took off my underwear, I got as hard as steel and Alison reacted to that sliding herself onto it then falling on me kissing my lips intensely as she started to grind on top of my junk. I then spun her round so that I was onto and started to really give it to her thrusting so much that she started to scream. More and more I pumped as she really didn’t want me to slow down, my hands running over her buzzed hair causing her to moan so much. “dont stop at all!” she yelled, I was more than happy to comply as I started to go even faster. Faster and faster I went until filially she let out a scream in pleasure letting me know that she was done. We laid there afterwards just kissing each other as finally we were together, I even admitted that I had a crush on her. To my surprise so did she and was always waiting for me to say something as she was really shy too. At that we smiled and re entered the bathroom to take a shower together.

The day after everyone was shocked to see what had become of Alison’s hair, but people respected her for going through with her bet. She often acted like she hated it, but deep down I know she really liked being buzzed. Right now she has a cute little bob and refuses to go any longer, she is done with long hair her words. The best part is that we finally found each other and we have both never been happier. I have a little treat for her at Easter, she wants me to shave underneath her bob cut so she has a kinda all over undercut but I think I’m going to razor shave it down to the skin. Hopefully she reacts as well to that as she reacted to the buzz cut. Fingers crossed eh?

3 thoughts on “Betting the Wrong Way

  1. JimB says:

    Man TAKE A BREATH …..

  2. Dave says:

    I don’t understand the new rating system. Under the previous one I would have given a 5 for excellence.

    1. hlstoo says:

      You can click on the stars to rate the story.

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