This is a story about my best friend and me on our road to discovery. It is a recollection of our first time pleasuring each other. I really loved her and fondly remember these experiences from twenty years ago. I hope you enjoy it as much as I enjoyed putting it in writing. This is my first time ever, writing out a story, but all of you have inspired me to give it a try.
Depending on feedback, good and bad, I'd like to continue my story. Please be gentle but honest in your comments. I hope you enjoy.
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I don't know how old we were when we first met, as it seemed we had always been friends. All I know is that Holly and I became friends sometime in Elementary School. We were just kids, innocent and pure. We lived close to each other and we would walk to and from school together. We would sometimes eat lunch at each others houses and would play together after school and on weekends. To tell the truth, I didn't even consider her to be a girl. Holly was just a friend and we did everything together. Holly was my equal in anything physical and we had a lot of fun together. We'd ride bikes, play in the park, shoot basketball, play soccer, and just hang out lying on our backs down by the river.
I think the first time I ever realized Holly was a girl was one day in middle school. I over heard a group of boys laughing and making jokes about my best friend. As I listened, I heard them saying something, how shall I say, less than polite about Holly's chest. I don't remember when Holly had started developing, but on that particular day, Holly had worn a t-shirt that was a little too tight. I found out later that Holly never wore a bra as she thought they were uncomfortable. Anyways, Holly's chest was very noticeable through the tight t-shirt. While curious, I was really embarrassed and didn't know what to do. Fortunately, one of our teachers had noticed and talked to her mother about the situation, and from that time on, Holly always wore a bra (at least from what I could tell). Looking back, the situation was handled pretty well as Holly had been spared any future embarrassment in front of the boys. Holly was a real tomboy and had not realized that her developing physique had any effect on anybody. Like I said, we were both pretty innocent and naïve.
However, from that day on, I suddenly noticed that Holly was not one of the guys, at least not physically. Holly was becoming a young lady and as such, I had to respect that. I knew what girls were like, I had four older sisters. But Holly and I were just friends. Physically we were both developing, but the changes were just cosmetic. We weren't any different inside. So we continued just being friends and spending time together. We did a lot of outdoor sports and played a lot of soccer with a group of other kids, but we also had our other activities and friends away from each other. I just treated her as one of the guys.
Eventually, Holly and I graduated High School together, celebrated our eighteenth birthdays, and were ready to conquer the world. I had noticed that Holly had blossomed into a beautiful young woman. Holly wasn't the prettiest girl, but she was very attractive and had a very athletic figure. I never tried to make a pass at her as Holly was still very much a tomboy. If Holly got mad at me, she wouldn't hesitate to slug me in the shoulder. Of course, I'd just wind up and slug her back, not hard enough to hurt her but enough to let her know I didn't appreciate the bruise she gave me as she was very athletic and had a nice whollup. Sometimes that would lead to a serious wrestling match and half the time I'd let her get the best of me. Holly was strong, but I kept my strength in check as to not physically hurt her. We were just having fun, but I would have never forgiven myself if I had ever physically hurt her.
In those times when I let her take me, I would let Holly pin me to the ground until I cried, "Uncle!" Then Holly would usually sit on top of me as we both caught our breaths. More than once while Holly was sitting on my crotch, I'd get a huge erection. If Holly ever did notice she never said anything, but I think Holly liked to tease me as I got the distinct impression that she enjoyed grinding her crotch against mine, fully clothed that is. Holly was a tease but who was I to complain. I was enjoying it as long as she did too.
Over the previous few years I had dated other girls as I could never seem to find a way to take Holly and my friendship to the next level. In truth, I was probably scared that Holly would get mad at me and not want to have anything more to do with me. So I dated other girls I knew, while Holly and I remained good friends. Holly never seemed to care too much and we still hung out. We'd occasionally talk about the opposite sex with each other but Holly never dated and never seemed to be all that interested in boys. There were a few times when I thought that maybe Holly preferred girls, but that didn't seem likely either. Holly just didn't seem all that interested in sex other than the occasional crotch grinding Holly would tease me with. I was still a young, immature young adult and I didn't know what to think. Looking back, I wish I would have just asked her.
Of the other girls I dated, I liked them all, but none of them became more than just casual friends. I mean we would sometimes hold hands and kiss, and there were even a couple of times that we got into some mutual heavy petting. After bringing one girl to orgasm that way, she was more than willing to go all the way, but for some reason, I didn't want to go all the way. At least not with her! I don't know. Maybe I'm a little weird that way, I wanted to do it, but on my own terms with someone I really cared about. Oh, she did jerk me off and it felt incredible, but afterwards we just held each other and kissed.
One day while in our freshmen year at the local community college, Holly came over at my house after classes. While doing some homework, out of the blue, Holly asked me if I had ever looked at a men's magazine before. I didn't tell her that I had a sizeable collection of my own hidden in my bedroom as she probably would have thought I was a pervert. Wait! I guess I was one, but let's not get too personal! I asked her why she was asking. Holly said that she had been in her parent's room one day looking for something and had come across a few magazines that her father had. Holly was curious if all men read these type of magazines and if I, specifically, read them. Read? Yeah right! 'Looked' would be the operative word. I was a little embarrassed and I guess Holly saw my face turn red.
I half-lied to Holly and said "Yes", but that my older brother owned them. Right! He didn't even live at home any longer but fortunately Holly didn't catch that one. I asked Holly if she had looked inside any of them and she shyly replied that she had. I asked her what she thought and this time it was Holly's turn to turn three shades of red. After patiently waiting and a little prodding, Holly said that at first she was just curious but that after a while she became interested. Holly wondered how she compared to other girls and wondered how she measured up. Oh boy! If Holly only knew! I would have loved to have shown her but I kept myself in check as thoughts that could have got me arrested in some States raced through my brain. Or, should I say my groin? I looked Holly in the eyes and told her she was the most attractive person I had ever known and that she should never doubt herself. I added that though I had never seen her without clothing, other than in a swimsuit, I thought she was more attractive than any of the women in the magazines.
Holly smiled and said, "Yeah right!"
I looked her in the eye and without thinking said, "Don't sell yourself short! I'd pick you over any of them any day of the week!"
Holly stopped for a second as she seemed surprised, and then smiled at me. Holly leaned over and gave me big hug and said, "Thanks. I needed that. Sometimes I feel so awkward."
Now I don't know if it was intentional or not, but as Holly hugged me, her breasts pressed into my chest. Suddenly, Junior quickly started waking up! As we separated Holly's hand fell from my shoulder and accidentally brushed against my growing erection. I think she noticed, as I detected a small gasp in her voice and her eyes got a little bigger. Holly just smiled at me.
I thought the conversation was over and had turned back to my books but then Holly asked me another question. "What do you think about when you look at one of those magazines? I mean, do you feel anything?"
I looked at Holly surprised and said, "I don't know. I guess I enjoy looking at the pictures. I guess they sort of turn me on."
"What do you mean by they turn you on," she said.
I replied hesitantly, "Well, it's a little embarrassing but, you know, they cause me to get an erection."
"You mean like when I just hugged you?"
"So you noticed, eh? Yeah, like that," I said as my face burned with embarrassment.
Holly smiled at me and leaned over and repeated the previous hug. My cock jumped a little! Holly laughed.
"Thanks," I said. "That's a really good way to build my confidence!"
Holly smiled at me and put her hand back on my crotch. "I'm sorry. I didn't mean laugh. I was just.... Wow! That is really hard! Does it hurt?"
