Ashley and I virtually grew up together. She is a year older than me. Our parents were friends and she was like my big sister. Usually this type of relationship fades when puberty starts, but that was unique about her. She is very loyal and caring. Not that she is a saint by any means. She is not easily influenced by outside sources or opinions of others. We went to the same elementary school but for some reason, different middle schools. That separation during those years caused some widening of our circle of friends. Also, during that time, Ash started puberty. She was always taller than me, but in elementary school it doesn't matter that much. I was a very late bloomer and did not hit puberty when she did.
Being in different schools hindered our friendship some, but our parents got together frequently, and we were together often. I did notice when she started spurting up and even when she started developing those pretty lumps in her t-shirts. When her breasts really started to grow, she seemed embarrassed at first, but later seemed to relish the fact that her bust was much bigger than all her classmates. When she did stop growing about ninth grade, she topped out at 5'-10". And she was no string bean either. Her ass took on that rounded heart shape. She played basketball in middle school, while I was in the band. We both made straight A's and were both interested in biology. I became much more interested in her biology, in fact.
It surprised most of her friends that she hung out with a little shrimp like me. She didn't seem to mind the ridicule from her girlfriends, but when she became interested in guys, one of them better not demean me in front of her. Kids can be so mean. Occasionally some want to be boyfriend would start rumors about why we were friends. When she started dating later, I was left behind often. She did include me in many group activities, but inevitably we grew further apart.
High school was a different story. We did not have any classes together until my junior year when I was taking some senior level courses and college credit courses. We loved to study together for those classes. We argued over some concepts just like brother and sister, but generally agreed on most things. She was attracted to the more mature boys and I was afraid of girls on a sexual level. Even though I was horny as hell just looking at Ash, I never acted on that. Anyone could see that an early maturing beauty would never have a love interest in a 5'-6" runt.
In eleventh grade I hit my growth spurt, but I had acne and I was always self-conscious about my face. My mother kept me at the dermatologist during those years. With treatment and good care, I eventually overcame it. I did not have to shave until my sophomore year in college. On top of that I have dishwater blonde hair and my body hair is almost nonexistent. What I do have is very light and sparse. I always dressed quickly or hid in gym classes. It wasn't just my lack of body hair. In fact, it wasn't that at all. It was my little dick. I kept waiting for it to grow when by body started growing some. It did not. After I turned twenty, I gave up hope and had to accept the fact that I had a very tiny penis. It is only two inches long when flaccid and three and a half inches when totally erect.
Not that it mattered in high school. I didn't have a girlfriend except Ashley, and she was just a friend. There was no romantic connection on her part. Just fantasy on my part. That was my focus during masturbation. I did look at some porn. I really loved the perfect female figure, but Ashley had one already. I just could not see her naked. The closest I came was in the pool. I made sure I kept my little dicklet under water. Small as it was, it still did get rock hard when I saw her perfect breasts spilling over her bikini top.
At that time, Ashley was concentrating on track. She was a hurdler. Those long legs and toned muscles led her all the way to the state championship where she finished a close second place. She is still pissed about not winning. This led to a major college scholarship. She went out of state while I stayed at home and attended university. Luckily there are three universities in my hometown, and I was able to get a scholarship based on my perfect grades. I studied hard and graduated in two and a half years. I did my master's degree in another six months.
I did meet a fellow 'geek' student, Karen. While maintain my friendship with Ashley via email, I managed to get in study groups with Karen. Eventually I asked her out and she accepted. This led to a casual relationship that eventually turned sexual. While Karen may have qualified as a 'geek' intellectually, she was not sexually inexperienced. I ended up losing my virginity to her. The first time we tried to have sex I came as soon as my little dick touched her vaginal lips. She tried to assure me that this was normal for virgins. I was so embarrassed that I stayed in my apartment for two weeks without calling her. Finally, she came over and confronted me. She had me strip and lie on the bed. She got naked and stood beside me rubbing her pussy and then rubbing her moistness on my lips. I was aroused. She sucked my little dicklet just enough to get me hard and then mounted me cowgirl style. Karen was not drop dead gorgeous, but she was cute. She was 5'-4" with a little more than an A cup. But her breasts were very pretty and her nipples got hard during sex.
Over time she taught me everything I knew about sex. However, sex was not the biggest part of our relationship. We clicked on an intellectual level. That was good enough for me, but ultimately, I learned that after we were dating about four months, she started seeing others. I did not know this at the time. I guess I was absorbed in school and never thought that she might need more than my little cock. Later after we broke up, I learned that she had told one of her friends that she could not continue to have sex with me and lead me on. She implied that my cock was too small to satisfy any woman and that was certain to doom any future relationship.
I was devastated when it happened. I emailed Ashely constantly hoping for reassurance. She was kind as always and tried to buoy my spirits. While she was in college, Ashley was exposed to just about everything. Being a female athlete, she was not surprised that many of her teammates were lesbians. She said that she learned to accommodate their sexuality and most of them were accommodating to her. Since Ashley was not interested in a lesbian encounter or relationship, she ended up dating mostly male jocks. She did not dwell on it much, but I learned later that she did not much care for an alpha male psychologically, but that she did love certain endowments that they offered. It was a trade off for her. She said that the alpha male macho bullshit was the thing that some of her lesbian girlfriend despised about men. On that they agreed and Ashley poked fun at them good naturedly about not judging her because she just loved cock.
After graduating, Ashley took a job as a high-level athletic trainer. She was very successful having had a strong athletic background. What eventually happened was that she built up her clientele from all over the nation. She trained NFL prospects, high school basketball and track athletes, both men and women in sports. Eventually, she got so busy that she had to hire assistants. This gave her more free time to set up programs, diets and workout regimens for her clients. She kept a close eye on the assistants lest they tried to take her clients. She understood that these people would one day leave. The catch was that they still had to rely on Ashley to speak well of them. It worked out great in the end.
While she was starting her business, I took a job with a very well know IT firm. It was a transition for me and most others. The big guys handled big clients and some smaller ones. Eventually the spinoff entrepreneurs would soak up some of the medium sized and smaller clients. That is what I did after two years of hard work.
When I first broke up with Karen, Ashley guided me through the grieving process. After I graduated with my master's, she told me to come stay with her for a while. I didn't have much money saved yet and we worked out a roommate agreement. She was so busy with the business at first that she did not socialize much and when she did it was with mostly clients. That is top tier professional athletes or aspiring athletes. Only a few of them made any suggestion that me living with Ashley was strange. She set them straight immediately by telling them just what our relationship was and was not. She was stern enough that they learned to respect our living arrangement.
I was still madly in love with Ashley and I am sure she knew it. As we became more comfortable with our arrangement, we interacted mostly like siblings. One night we went out to a club together and danced too much. We also drank a little too much. We caught an Uber back to her condo. Though still buzzing, we were not sleepy. I poured us some wine and we settled down on the couch together. It must have been the liquor, but as we talked, Ashley already short skirt rode up her legs. I could see her gold thong panties and the outline of her bare pussy. I slowly place my hand on her leg and continued talking about our evening. She did not resist but opened her legs slightly. I moved my hand up to her thong and traced the slit of her pussy.
Her eyes opened more and she looked directly at me.
"Ray. Are you trying to fuck me?"
"Uh, well, gosh, Ashley. You know I have loved you for a long time."
