The convention

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It was my fourth night in Chicago.  I was selected to go with 5 other co-workers to work at my companies booth at the convention center.  The first three nights we worked until early evening, and either had room service, or ate together at the hotel bar.  Tonight was the first night that we had the evening off.  All of my co-workers, all male, were all excited to head out bar hopping, the thought of being hit on all night by a brunch of drunk guys wasn’t my idea of a fun night, so I turned down their offer to join them.  I decided to head out on my own for the evening, and on my way thru the lobby, the concierge, a short haired girl named Hannah, saw me and asked where the rest of the group was.  I told her I didn’t want to be hit on by guys all night.  She tells me she knows just the place I needed to go to and she gave my a flyer for a place just around the corner from my hotel.  I found “Club V” just 2 blocks from the hotel.  It looked like a nice place from the exterior so I headed inside.  It was still early, so it was still mostly empty inside.  I ordered a drink then looked over the menu the waitress brought my drink and took my food order.  While I waited for my food I see more people start to filter in.  After a few minutes of people watching I noticed that I had not seen any guys come in yet.  I then wondered why the concierge thought this is where I should spend the evening.  I came from a religious family and had always went out with guys, so I hadn’t noticed the concierge flirting with me.  The food was great and the drinks were strong, so I decided I would stay for a while.


I had been at the club for about an hour and I was ready to move on for the evening when I was approached by a girl that I would have to say was butch.  She had short hair on the sides with a gelled fauxhawk on top.  I had never had thought about being with another girl before, and wasn’t looking to be with one now, so I politely told her I was not interested.  To my complete horror she then says” come on Lisa let me buy you a drink.”  My mind was racing as I tried to figure out how this girl knew my name when she then says “Do you still live with your parents on Maple Street?”  I still was at a loss trying to remember how this girl could know all this about me.  The girl sits down across the table from me and then says “How do you think your mom and her church friends would feel if they knew you were hanging out in a bar full of lesbians.”  My thoughts immediately changed to how upset my family would be if they knew I was here.  While I considered myself quite liberal when it came to peoples lifestyles, my parents were very conservative Christians who thought of gay people as disgusting.  I took a hard look at the girl and then it came to me.  Her name was Kimberly, and she was 2 years older than me.  We had grown up on the same street, but were never friends with each other.  Then I remembered that she was sent to boarding school when she entered High school, and I was in middle school.  I never saw her after that and assumed she went to college then moved away.  She then told me that it wasn’t really a boarding school she went to, but a camp that run by the church where they tried to “fix” young people of the gay feelings that they had.  Kimberly said she spent 9th grade locked up, unable to leave the compound, but the summer after that she was allowed to go out in groups with a chaperone.  On her 3rd time allowed out she found a way to escape, and never went back.  She had not been back home since she left 18 years before.


I don’t know why, but I felt like we had been friends for years.  We sat there until last call, but I wanted the evening to continue so, surprisingly I asked her to come back to my hotel.  As we walked thru the lobby the concierge gave me a smile and a little wave.  We sat in my room and talked for several hours.  A little after 3am Kimberly said she should call it a night.  I told her she was too drunk to find her way home by herself, and quite innocently told her she needed to stay in my room for the night.  I had asked her to stay for her safety, thinking she would sleep in the extra bed.  To my surprise she came out of the bathroom in just her panties, and got into my bed.  My mind was racing.  Here I was, a good girl from a religious family about to share a bed with another girl.  Due to my upbringing I always felt guilty when I had sex with men before, but this was a whole new level.  I got into the bed with no idea what was about to happen, but, I felt close enough to Kimberly to proceed.


That night was one I will cherish for the rest of my life.  Kimberly knew that this was all new to me, and took charge of what went on in bed.  I thought that I would be overcome with guilt for being with a lesbian, but, just the opposite happened, I felt totally at ease with her.  The next day I had to work at the convention center again, but my thoughts were consumed with my night with Kimberly.  I told my boss that I wanted to take the next week off for vacation.  She scoffed at the idea at first, but when I offered to pay for my own flight back home she gave in.  Kimberly too was excited, she insisted I check out of the hotel and stay at her place.  My first thought was the $300 per night I would save on the room.  Kimberly had other thoughts on her mind.  We hit some of the standard touristy spots on Monday and Tuesday, then on Wednesday she said we should go for coffee and run her errands.  After we grabbed our coffee Kimberly said she had a hair appointment, but, if I didn’t want to waste time she could reschedule it.  I figured it was only a half hour so she should get it done.


After a short walk we arrived at a small barbershop.  We walked in and the barber greeted Kimberly as an old friend and gave me a big smile.  She told us to have a seat, again smiling at me she said “It won’t be too long”.  I had assumed that I was going to watch Kimberly getting her hair done but when we sat down I looked at Kimberly and only then realized that her hair looked like it had been cut recently.  I still hadn’t figured out what she was up to when the barber finished with her customer then she looked directly at me smiled again and said “okay your next”.  I didn’t immediately react, then Kimberly patted my arm and said ” Go on Lisa, it’s your turn”.  I slowly got up, and made my way to the chair.  As I sat in the chair the barber floated the cape around me and asked what I wanted to do.  I only ever had my long hair trimmed, not cutting more than 2 inches at any one time, so I asked her to give me my standard one inch trim.  The barber then asked if I was with Kimberly to which I replied that I was.  She then said, “Well I know that Kimberly only dates butch girls, so I might want to pick something more fitting to what she wants”.   I wasn’t prepared for this, Kimberly and I never discussed my hair or wanting me to cut it short.  I asked her what she wanted me to do, but she just said to me “You saw the kind of people I hang out with.  If you want to be with me, I like bois type girls, no girly girls for me”


The whole situation made my mind spin.  I was falling hard for Kimberly, but I knew my choice had definite consequences.  My family was still very active in the church, and that meant I would probably not be welcomed home once they found out I was now a lesbian.  Still, I was kind of liking the thought of `what my new life would be like.  I asked Kimberly to pick a haircut for me, but she insisted that this was a choice I had to decide on my own.  I looked at a poster that was on the wall across from me showing short clipper cut styles.  I decided on boy cut with short spiky hair on top, with white-walled sides.  I looked over at Kimberly as I was telling the barber what I wanted and saw her nod with her approval.  The barber didn’t waste any time cutting my shoulder length hair off at ear level.  Then came the clippers.  Having already been in a heightened state of arousal, the feeling of the clippers running up the back of my head put me into a state of euphoria.  I don’t know want happened for the rest of the cut, but came to my senses as the barber started shaving my nape and a full inch over my ears.  Kimberly had the biggest smile on her face as she got up from her chair and told me how proud she was of my choice.  She then went on to tell me that if I was her girl it would be the last time I picked out my hairstyle.  I was to come to the barbershop every 2 weeks and if she hadn’t told the barber how to cut it, then the barber could do as she please.


Three month’s have now passed since I have left my job and moved in with Kimberly.  I only went back to my old apartment so I could grab some of my personal belongings and get rid of all my other stuff.  I gave all my old clothes to a charity shop because they were suited for a girly girl, not the butch girl that I now proudly am.  Kimberly has kept her promise, selecting  shorter and shorter haircuts for me, but I am nervous for tomorrow because she is traveling for work and said she didn’t have time to tell the barber how to cut my hair.  This will be the first time the barber has free reign, but she has hinted over my last several visits that she always wanted to give a girl a flat top.  It looks like she will get her wish.



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