First Encounter

When I was in Middle School I met my first girlfriend. I remember that day like it was yesterday. We were outside after lunch when I saw her for the first time. I immediately had a feeling of butterflies in my stomach at the site of a girl for the first time. She was the most beautiful girl I had ever seen. Tall, athletic, with long flowing blonde hair. I asked around about her and learned she was new to our school and did not yet have a boyfriend. It took no time at all for word to get back to her that I was interested and by the end of that day I had been passed a note, carefully folded into the shape of a rocket, asking if I would be her boyfriend. I was on top of the world and had fallen in love at first sight.

We were an item for the remainder of our time in middle school. We attended dances and banquets together, did the homecoming rituals of mums and garters, and would occasionally meet up at the town theater to watch a movie. I would spend the entire movie working up the nerve to hold her hand. The idea of kissing or anything beyond that was just not even a possibility in my mind. Eventually, one of her friends would share with me that Julie was getting restless for her first kiss. Apparently I was moving too slow. I agonized over it for days and eventually asked her to meet me during class at the coke machines for a private kiss. I was so nervous and worked up over it that it amounted to a forced peck on the lips that really wasn’t enjoyable because off all the stress I put myself under. Nevertheless, we continued our relationship not really knowing what to do next.

One day during summer break we were chatting on the phone when she asked if she could come over to my house. My heart was about to beat out of my chest at the thought of it. I agreed even though my parents had a strict rule of not having friends over, especially girls, when they were not home. She arrived a short time later and I greeted her at the door shocked that she was wearing lipstick, very short shorts and a tight fitting tank top. This was unheard of for a small town girl in that era.

We broke the ice with casual conversation until she boldly proclaimed her disappointment with the level of intimacy in our relationship. I admitted that our one and only kiss had not turned out like I had imagined. She suggested we try again in the comfort of  complete privacy afforded in my bedroom. She also suggested that we lay in my bed so it would be like “in the movies.” She was right, the private setting and the spontaneity made me much more at ease and we began to passionately make out and eventually even used our tongues. My early teen hormones kicked in and it was no time before I was sporting quite a boner and was worried she would notice and think I was a pervert. 

When we broke our embrace she did quickly take note of the tenting in my shorts and asked if it was because we kissed. I said yes and added it was also because of how pretty she was and how she was dressed. She broke into the biggest smile and said she was relieved to know she could have that affect on a guy. When I asked why she would ever doubt, she became noticeably self conscious and mumbled something about not being as well developed as other girls in our grade. I honestly had not noticed because in my mind no one could compare to my Julie. She lamented that she was as flat as a boy and other girls had B cups and some even larger. I told her it really didn’t matter to me because it wasn’t like I could see them or anything. That’s when she said I could, if she had any to show, but only if she could see my hard on. 

My mind began to race out of control. I had never even considered this moment as a possibility when she asked to come over. I told her I would show her my cock but she had no obligation to show me anything if she was uncomfortable. I took it out and felt so good having someone else see it. She stared for a moment and admitted it was the first she had seen and much bigger than she had imagined, but made no attempt to touch it and seemed to lose interest pretty quickly. I on the other hand was getting really worked up and wanted to go further. I asked if she would let me see some of her and she surprisingly agreed to showing me her pussy but not her tits. She removed her shorts and panties and  my eyes gazed upon the first vagina I had ever seen in real life. She had a small amount of light colored pubic hair which closely resembled mine. Her slit was nice and clean and the sight of it provoked feelings inside of me that I had not yet experienced. After a few seconds of viewing it I fully expected her to put her shorts back on, but instead I was met with the strangest request. She asked if we could pose in front of my mirror and standing behind her if I would put my penis between her legs so she could see what she would look like as a boy. I was eager to comply as it would put my cock against her beautiful pussy. As soon as we got into this position and I was enjoying the warmth of her pussy against my cock, she quickly removed her shirt revealing only the slightest beginnings of breast buds. That’s when she giggled and said, look I’m a boy.

I instinctively began to thrust my hips causing my hard cock to rub against her labia when she pulled away and began to put her clothes back on. She said she had to get home before her mom returned from work and left soon after with me confused and wanting more. A quick peck on the lips goodbye and she was out the door. I had not discovered masturbation yet and had never had an orgasm at that point so I was relatively satisfied with our experience. Like I said, the feelings I experienced were pleasant and new, but far from what I would later learn was the “end goal.” 

Julie truly was my first love. Sadly, that one encounter was the most we ever did. After that summer she got more involved with sports and me with band and we grew apart. Later in High School, she began to date a popular jock. She remained very nice to me and we would occasionally talk on the phone to catch up. Once she came to a church youth retreat without her jock boyfriend and spent almost the entire time with me catching up. Later in a capture the flag game that night, I fell in the dark and got pretty banged up. She stopped playing and helped me off the field and tended to my minor wounds while the game continued without us. I never stopped loving her and I think she knew it.

In college we lost touch but I never stopped thinking about her. I heard she was planning on marrying the Jock from high school after they finished college. I had other girlfriends and even a lot of sex by then, but Julie was the one I always wanted. After college, I moved home to realize that Julie had broken off her engagement with the Jock and was living with her mom. I reached out and we picked up right where we left off. We were inseparable again. We even went to Vegas once to celebrate turning 21. When we checked into the hotel I was sure this is where we would finally make love. She requested two beds from the clerk and I began to worry that maybe I was misinterpreting our relationship. I made multiple attempts to become intimate with her on the trip and all were rejected. Finally, one night at dinner she broke the news to me that we would never be more than friends.

After that trip, having full realization I was in the friend zone, I moved on but never really got her out of my mind. Years later when I was engaged to a smoking hot girl, Julie reached back out and asked if I was sure about getting married. To be honest, she did have me second guessing my decision for a brief period of time.  I finally concluded that I had given her plenty of opportunity, but for some reason bigger than me, that ship just would not sail. Years later I found Julie on social media and the rainbow flag that was her photo background and the other girl listed as her “partner” helped me to understand a lot. 

I still think of Julie fondly. I could not count the number of times I have masturbated to the memory of our one time sexual exploration . I credit her body and that experience to the formation of my life long sexual preference toward  tall, athletic blondes with very small tits and little to no pubic hair.