I had a crush throughout the last half of high school. It was a girl named Ashley I had known since about 7th grade. I had not really gotten to know her until high school where we had a few classes together. The more I got to know her the more I began to like her and notice just how unbelievably attractive she was. She was not so much hot, sexy, or erotic, but she was cute as hell.
She stood about 5’9”. Short compared to me at 6’7”. She kinda looked like Avril Lavigne with her eye shadow hazel eyes, big smile, and white skin. Although her face was the only way they looked alike. She was taller and with much bigger boobs. I began to think how I could have missed those. She was skinny, not bony at all, but she had a very slim waist and cute little ass. Her DD boobs seemed to not go with her body, but her height helped. She was a little goth but not much at all. She cut her hair to her shoulder and went brunette with some reddish streaks from her strawberry blonde hair but sometimes she put it back in a ponytail and/or let it go back to her natural color. She wore some tight shirts that showed the size of her breasts. She usually wore some dickies pants but other times she would wear these tiny skirts with shorts under and boots with fishnet stockings.
I really got to know her junior year in my chemistry class where we didn’t do much but talk. She was actually a cool person, a little immature like me, and to my disappointment, had a boyfriend. I still became good school friends with her but we never really hung out of school. We would be really good friends in school and would sometimes talk for a while. Senior year she broke up with her boyfriend. She really wasn’t all that upset about it. I talked to her about it and she said that he seemed to be more into his friends than her. I said that he was a dumbass, and that how could anyone not focus more on her.
Not long after that in our economics class when we were doing nothing us and a couple of her girlfriends that sat nearby were talking. The conversation went to what they were looking for in a boyfriend. I paid attention to what Ashley said especially. She simply said that she was looking for a sweet guy that would pay attention to her, not in a “you are the most important thing in my life” way but still in a way that made her feel she mattered. She also said something that surprised me but not her friends. She said that she would like her next boyfriend to be a virgin like her. She spent about a year and a half with her boyfriend and didn’t have sex! Well better for me. I never really had a serious girlfriend in high school and I was one too. I thought I fit the description pretty well. I was huge but I was, as many of my female friends said “a sweet guy”. I was just to shy to make a move plus I think she didn’t really want a boyfriend at that time either. She obviously wanted the first guy to be special and I shared her feeling about my first girl.
We graduated, and at the graduation ceremony we said our good byes hugged and left. I still saw her but not much at all. I knew she worked at a restaurant but I never really got the chance to go. I saw her a few times over the summer but then every time I went to the restaurant it seemed to be that she had that day off. I knew she still worked there because I heard a few other employees talk about her.
I went to the local community college and hoped that I would see her there because she was thinking of taking a year off and then maybe go to the same school. I never saw her there. I later transferred to a university and I was in the middle of my junior year and then I heard my name called as I was just leaving class. I turned but I couldn’t see anything.
“Ed,” I heard the clearly female voice call my name again, and this time I saw her. I didn’t believe it. It was Ashley. I saw that she hasn’t changed her look and neither have I except that I had lost weight and was noticeably skinnier than I was in my husky days in high school. She came up to me and gave me a big hug. I picked her up as I hugged which made her laugh excitedly.
“Long time no see,” she said. We both didn’t have any more classes that day so we went to the cafeteria to catch up. I found out she had taken that year off and managed to get on the waiting list of the school and was eventually accepted. She lived on campus and worked in a department store nearby. I paid close attention and still marveling at my friend and ex crush here after 2 years of not seeing each other.
I then told her about me. I had transferred there and had scored enough financial aid to get a place right off campus and I worked in an electronics store a few minutes away from the school. She seemed impressed that I lived alone. I told her not really because this school was relatively close to my parents house so I went there just about every week for laundry and a good home cooked meal. We were there until for a couple of hours just talking and it seemed that we were right back to where we were back in high school if not closer.
My old feeling for her had returned and having gained some confidence I began to lightly flirt with her, smoothly throwing a few compliments her way when I got the chance. Every time I did this she giggled and seemed to blush. I knew I was much more attractive now than I was in high school and maybe I thought I had a shot with her. When we left I got bold, at least for me, and asked her out for a friendly dinner the next day. She agreed and said that we would meet here at about 6. I dressed what was fancy for me, in some kaki pants and a semi casual dress shirt, and my jacket because it was winter, but this was California so it was only about 60 degrees.
I couldn’t really concentrate that day but thankfully I had my easier classes that day so I was fine. I got there about 2 minutes before 6 and I saw Ashley sitting at the same table we were sitting the day before. She was wearing some black boots that reached half way up her shins and this black skirt that reached mid-way down her thighs with a white blouse. This was definitely the fanciest I’ve seen her but it still had that casual look. She had her hair tied back with two bangs hanging over her face. She still looked cute as hell but at the same time she looked sexy.
I led her to my truck, and like a gentleman I opened the door for her. She thanked me and gave me little curtsy. I got in and she told looked at how I fit in it. She laughed and said that if I was any bigger I would need a semi-truck to drive. I told her that they had smaller interiors than you think which made her laugh more. I had always enjoyed her laugh. We got to the restaurant. It was not a fancy restaurant; it was more like Denny’s than a fancy French restaurant. We ordered and continued to talk. She commented that we didn’t talk about our love lives yesterday and wanted to know what was up with me.
“You lost weight and now you are even hotter than you were back in high school. You must be beating off the girls with a stick,” she said. I couldn’t help by blush at what she said and I could tell she noticed. I told her I went out with a few girls but I just couldn’t find a good girlfriend.
“I thought guys were just looking for a nice piece of ass. Why are you looking for a girlfriend?” She asked jokingly.
“Oh don’t get me wrong, I still look for that nice piece of ass but that is not all that I want. I would actually like a relationship with a sweet girl… you know?”
“I think I do.”
“What about you?”
“Well, I really haven’t dated anybody either. I usually just go out with friends instead of date.”
“Why? It can’t be that you can’t get a guy, I mean just look at you!”
Now I made her blush. “Its not that its that I just feel that guys are just after one thing.” She then points at her breasts to illustrate her point. I take a quick glance but do not linger there for long.
“Aww, come on, there is a lot more better things about you than that.”
“Like what.” She said with a gleam in her eyes.
“Well, for starters…” I paused to make it look like I had to think about it. “There is your smile and eyes which catch my eye a lot more than those.” I said. “Plus, you as a person, are just great.” She smiled and looked down trying to hide the heavy shade of red she was turning. I was enjoying just flattering her.
“You really think so,” She then reaches over and takes my hand into hers. We have often hugged but this contact seemed to have more meaning behind it.
“Of course I do, when have you ever known me to lie.”
We continued to talk but we talked more about our casual lives and school. We eventually realized that there were people waiting to be seated and we’ve been done eating for a while. I asked her if she would want to go to my place to continue talking. She agreed and we went to my apartment.
I gave her the little tour and we went to the living room she sat on the couch as a grabbed a few of sodas from the fridge. I sat next to her and we continued our conversation. Eventually we decided to watch some TV but still continued to have a little small talk during commercials and such. Eventually we both inched closer to each other and I put my arm around her and she puts her head on my shoulder.
I have had sexual fantasies about Ashley, naturally, but I have also had deep feeling for her and I have dreamt about holding her closely and lovingly as I was at that moment. She then put her arms around me as well and we stayed like that holding each other for a while. We continued to talk and eventually forgot that the TV was still on.
I decided to lead the conversation back to our love lives and brought up that conversation we had back in highs school. She laughed because she didn’t think that I would remember. I assured her I had a good memory.
“I am still a virgin and am looking for pretty much the same type of guy.”
“I’m still a virgin too.” I said.
“No way… Look at you how could you not get a girl.”
I smiled at her comment and made it known to her that I appreciated what she said. “That’s not really the problem. I could have already had sex if I wanted too. The problem is that I want a the girl to be special, you know.”
“Yeah I know,” she said. We looked into each other’s eyes and had our first real kiss, and then hugged each other closer and continued to watch TV. Finally we realized the time and we realized that although we had no school tomorrow we both have to work. She started about half an hour before I did.
“You know it is kinda late and I don’t want to wake my roommate up so can I just crash here for the night.” I agreed but I know her so I knew not to expect anything. She asked me if I had anything that she could sleep in. I looked in my dresser and pulled out a pair of old sweats. She went into the bathroom to change and I changed into the sweats I used to sleep in. When she came out I was just floored by what I saw. She was wearing the sweatshirt that I had given her but not the pants and her socks. The shirt was big on her so it almost reached down to where her skirt was. She had taken off her make up but still looked cute as hell. She smiled and seemed a little embarrassed with the sleeves of the sweatshirt being to long for her arms and covering her hands. She smiled and said that the sweat pants were just to big to wear so she decided to just wear the shirt since it was long enough.
I just nodded and she went over to the bed and got under the covers. I said that I would sleep on the couch so she could have the bed and she told me that It was fine if I got in there with her since she trusted me. I paused a little but decided to get in bed with her. I wasn’t just happy that she said that it was fine for me to be in bed with her but that she also said that she trusted me.
We said good night to each other and she then turns onto her side with her back to me. I reach over and hug her and give her a kiss on the cheek. She grabs hold of my hand and keeps it there, signaling that she wants to fall asleep with me holding her. I position myself so that my inevitable boner won’t poke her while we sleep. I had managed to keep control until now but I knew that wouldn’t last.
When I awoke the next morning I realized that we were in a different position. I was now on my back with my left arm around her and she had her head on my shoulder and her hand on my chest. I just watched her sleep for a while admiring her. I had a hard on, obviously and concentrated to get it down. I then realized the time and I knew that I had to take her home to so she and I could have time to get ready and go to work. I kissed her softly on the forehead to gently wake her up.
