My Friend Ashley Ch. 01

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."

"I know, but our relationship is more like family."

"Yes, but not blood family, Ash."

I don't know why, but she stood up and removed her skirt and top. She unhooked her demi-bra and stood there in just heels and the thong. She towered over me almost a foot in her spiked heels.

"Ok, Ray. If you think you can handle this, come on."

She walked across the room into her bedroom. I followed. When we got near her bed she leaned down and kissed me. She kicked off her heels and peeled off the thong. It was my dream come true. Tall, long legged, big breasted, blonde amazon woman and getting naked for me. Then the anxiety made my hard little cock deflate. She started pulling off my clothes and stripped me down to my briefs. I pulled them down and she saw my pitiful excuse for a cock.

"Oh, Ray. It is so cute, but so limp. Does it get hard?"

I was too embarrassed to answer. She knew that I was not a virgin, but this was like the first time I made love to Karen.

"Tell you what." She said. "I am so horny I could fuck anything right now. Get up on the bed and lick my pussy. If that doesn't get that thing to attention, we will try something else."

I knew little about oral sex. Apparently, she knew a lot. She guided my face to her beautiful vaginal lips and pulled my mouth to her sex. I began licking her. She softly instructed me on how and where to put my tongue. Eventually she guided me up to her protruding clit. It was much more prominent that Karen's had been. It pierced my lips like a tiny cock. How ironic, I thought. Her clit was almost as long as my cock. Well, that was an exaggeration, but I could not help thinking that anyway. She guided me so well that she had an intense orgasm.

As she relaxed, she told me to fuck her. My little cock was very hard now. I had regained my form while she helped me to pleasure her orally. She had me mount her and then she guided my little gusher into her waiting sex. She felt so wet and hot. I came immediately. She knew it and continued to rub my ass as my little cock returned to its wet noodle state.

What could I do now? I knew that if I could not satisfy my ex-girlfriend with my little appendage, I had no change of servicing Ashley with it. She spread my cum around her pussy and used it for lubrication. Then she guided my fingers to her pussy and had me bring her off with my hand. Again, her clit rose to her full hardness. I was amazed at what caused this oversized protrusion. I assumed that like dicks, they came in all sizes. I had seen some pictures of pussy but never really noticed as prominent a clitoris. I guessed that these pictures were taken when the women were not sexually aroused.

I drifted off to sleep. It was the combination of the alcohol and sex. I kept waking up and looking over toward Ashley. She was indeed sleeping soundly next to me. It was not a dream. I managed to get in some cat naps during the night. I arose just after dawn. Ash was still sleeping. I went into her kitchen and made coffee, bacon, scrambled eggs and toast. I did not have to wake her.

"Oh, good job, Ray. You are such a good wife to make me breakfast."

I knew it was just an expression. She was just joking. Somehow the relationship aspects managed to soothe me and make me somewhat euphoric. I had just had sex with my one true love and she alluded to a different kind of bond other than friendship. I was probably not thinking right and read too much into the casual conversation.

We had breakfast and talked about the evening before. I mentioned the club and drinks. I jabbered incessantly about dancing and drinking. Finally, she said, "Don't miss the elephant in the room, Ray. We had sex. I know it was a combination of drinking, dancing and letting off steam, but we just had sex. I don't want that to ruin our friendship. So, let's just put it in perspective and not get too uptight about it. We can talk about it now or later. I don't regret it because I think it was actually good for both of us."

We mentioned it a few times each over the next week or so. I was on my best behavior. I cooked for her and cleaned the place. I served her just about everything she wanted. I was hoping that my dream would continue. I saw our lifelong friendship as just the start of a lasting relationship. I would pinch myself and tell myself to slow down.

Later that week, she came home from her gym one evening. I had cooked, but she just had a bowl of soup and then took a shower. When she got out, she came into the living room wearing panties and a thin tank top. God, she was gorgeous. I poured her a glass of wine and sat next to her on the couch. Just as I was making progress in subtly moving closer to her, she said, "Ray, we probably should talk about the other night. Our friendship has always been special to me. One, it is unique for two people to be this close without being romantically involved. Two, as I said, I don't want that to ruin our friendship. It is a more modern society than our parents grew up in and sex comes more easily with less guilt. It was sweet, but we really need to take stock of what our next step is."

Next step? Next step? How wonderful that sounded. Maybe Ashley was done with the hot studs and just wanted a husband to love her. She surely did not need me to provide for her. She was more successful already than I was. As mentioned, I later got a foothold on my business and became well off enough to move out of her apartment.

But right then, she brought me back down to earth.

"Let's look at the practical side. If we can be roommates and the chance comes up again, I have no problem with what happened the other night happening again. However, I worked hard while in college and then starting my training business. I have tons of commitments to clients and yes, some of them have become occasional lovers. If we can move on from that and not become emotionally involved, then let whatever happen. But if you come out of your pity party funk and find a sweet girl that loves you, I will be the first to congratulate you. Heck, I would even be your best 'man' at the wedding. That is how I value our friendship. When I entertain guests, which will sometimes happen, just be sure that you are and act like my roommate."

While somewhat encouraged by the total commitment Ashley was making to me, I was still bummed. I knew now and forever that I could never become romantically involved with her. She was a winner on the scale of twelve out of ten. I knew that I did not have the full package. (Pun intended) To think that she would marry a man inferior to her in every way was total fantasy to me. How could I be so stupid? I almost resented her for having sex with me. It took me a few days to come to grips with my feelings. I was just a crybaby about emotional attachment. I knew that Karen had not left me just because my dick was so little. It had to be more than that. After a few days, I finally had my head on a little straighter and decided that staying with Ash was way better than moving into an apartment by myself and being lonely all over again.

When I came clean to her about my mixed emotions, she said, "Oh, I am sorry, Ray. I didn't mean to come across as a bitch. I want you here as long as you want to stay. While our relationship is unusual for a man and a woman, it is more unusual that two different sex people can be this close without sex getting in the way."

She caught herself. "That came out wrong. What happened was not something that I regret and I hope that you do not either."

"Are you kidding me, Ash. That was the highlight of my whole life so far. I mean sex was good with Karen. I mean, well, you know, all right. But I guess the fact that she was not getting what she needed sexually sort of held her back and left her unsatisfied. I tried to fill the void, but in the end, she told others that I was not up to standards."

Ashley smiled her lovely enduring smile. "Uh, Ray, don't worry about the equipment, Dear. Unless you want to seek surgical remedies, you should learn to appreciate what you have. You are brilliant, while a little on the shy side. Put your confidence in your talents, not your shortcomings."

"Does that mean that you could learn to love me regardless of my penis size?"

"Ray, I already love you. Our friendship is so dear to me and I know it is to you. But as far as becoming committed lovers, I, uh, well, that is probably not in the cards. I have started to enjoy my sexuality and I have been fortunate to learn to be more accepting of sexual feelings. I was a little uncomfortable in the beginning about being around women who were openly gay. Over time, I learned a little about looking at the person. Some of them were bitches, yes. But I learned that it was not necessarily their sexuality that made them bitches. Some people are just bitches. Women and men. There does not need to be a distinction necessarily. The good thing about the women's movement is that we no longer must live up to male expectations. Or female, either. So much is becoming equal. Hell, awhile back, some people would have a problem with you living here with me. Fuck 'em. Fuck their labels."

"Have you ever, uh, you know?"

"What?" she asked, "Made it with a woman?"

"Uh, well, have you?"

"No, Ray. But that does not mean that I think of myself above that. Like I said, screw the labels."

Sex with Ashley was wonderful. For me. But I knew it was not for her. I could not be so selfish to think of myself only, knowing that I was so underendowed. The more I thought about it, the hotter I got thinking of my beautiful blonde friend enjoying a big cock. I brought up the subject soon afterward. We were close enough that I could ask her about her love life. We were watching TV one evening and I just came out with it.

"Ash?" I said, "For you is sex about the relationship or the act?"

She giggled. "Both. I mean sex with you was a little awkward, but I was glad that you made the first move. I did not expect it because I was afraid that you would think that sex was more of a commitment. You had sex with your ex-girlfriend, and you are still down in the dumps about losing her. I had sex with you because I wanted to. I don't mean to mislead you and that is why we must be open about it. For some reason, a guy with a big cock just makes me want to fuck. Not make love, mind you. Just fuck. I want to take all of his cock. The bigger, the better. I want to wear out the big stud and just fuck him into submission."