This story is from my college days. I was going to school at a little church college on the North Shore of Oahu. I won't name it because this isn't the right place or time to bring in religion, but many of you may know the college. Anyway, I had set my sights on this 19-year-old freshman girl named Kate (of course I changed the name). She was out of my league, but she was a freshman and I was a Junior and I figured if I got to know her before the other guys discovered her than I might have a chance.
Kate had super long brown hair that went past her waistline. She was part el-Salvadorian and her skin was a dark golden brown. She had a tiny waste, a round athletic butt, and full breasts and a smile that melted me. Honestly, I couldn't find a flaw in her figure or her face. I was infatuated.
As for me, I was a casual surfer through high school from San Diego and continued surfing through my days in college in Hawaii. However, in college I also picked up swimming and weightlifting for exercise. I was swimming 3 days a week and lifting weights the other two days and surfing in my free time. I was in good shape in high school, but any softness I did have was melted away in my wonderful Hawaiian lifestyle.
My problem was that I was a really nice guy. I had no shortage of girls interested in me, but I was insecure and naturally very shy, and I would get moved very quickly to the "friend-zone". I was told often how good looking I was (and looking back at pictures they weren't lying) but that I was just too needy and too nice. Ugh!
So I started asking Kate out on dates. She accepted enthusiastically and we started going out often and became very close friends. Being my terribly insecure self, I didn't have the courage to make a move on her and so by the fourth date the closest I had ever got was to put my arm around the back of her chair. But. . . she kept saying yes, and I kept asking her out. After a few weeks we were hanging out between classes, eating lunch together, and we had become best friends - all without me making a move.
I had blown it. I had once again moved myself into the friend zone. Years later she had confided in me that she was more than ready to move things forward, but I had given her clear signs that I was not interested in her in that way. Ouch! The problem had been I was TOO interested in her and the fear was just too great. We hung out nearly every day on the beaches and she would watch in her tiny bikini while I surfed -- all the benefits of a hot girlfriend without any of the physical benefits. It was pure frustration.
Most everyone in the school thought we were a "cute couple" and she and I had to keep telling people that we were not dating (again ouch!) -- we were just close friends. Our reputation as a couple was so complete that neither she nor I could get a date without reassuring people that we were not a couple.
Six months later. . . my best friend Joe (again, changed the name) joined me at the college and moved in as my roommate. We were both 22 years old and Juniors, with one year left until graduation. My torment was complete when I introduced him to my friend Kate and within two days of hanging out on the Hawaiian beaches, they were making out feverishly in the sand. Kate in a tiny bikini that barely covered her tan body and Joe in his swim trunks.
I still remember watching him stand up and stretch after that first make-out session and seeing his erection protruding like a flagpole through his shorts. I knew that she had to have felt him pressing against her stomach and I felt the knife of jealousy take an extra deep twist in my gut. I had wanted to press myself against her just like that for the past six months and now that hope was gone.
Kate and Joe quickly became an item.
Now that the pressure was off and I was no longer constantly afraid of blowing it with her, she was very free with her hugs and touch, and even friendly kisses on the cheek. Joe was her boyfriend, but in many ways, I was still her best friend -- the one she came to for support. She and I grew closer without the threat of a relationship in the balance. I was finally able to open up to her and tell her how I felt. Joe already knew how I felt because he knew I had been trying to get together with her even before he became my roommate.
I went through a period when I refused to go out with the two of them (both my best friends) because of the intense jealousy. They agreed to cut down on the making out in front of me and I went back to being a third wheel.
About this time, Joe bought a very old and beat up CJ-7 Jeep. The Jeep had no doors and no top and was the color of rust from top to bottom. It drove like a tank. It was loud and windy and perfect for our island lifestyle -- and it only had two seats. This gave us the freedom to surf up and down the North Shore and weekend trips to Honolulu to play at being tourists or to see a movie.
I tried riding in the back with the surf boards and gear, but that was super uncomfortable. Kate offered to take turns riding in the back, but I was way too much of a gentleman to be comfortable with that. So, we compromised on having Kate sit on my lap while Joe drove (I'll come back to this).
I should mention that Kate was not perfect. She had one huge flaw -- she loved attention. Along the way, Kate had begun to tease me by showing off parts of her body. For short or occasional trips most surfers spend the day in their swimsuits. However, when it is your daily lifestyle you learn that it is nice to rinse the sand off and put on dry clothes. Otherwise, you would spend literally every day in a wet swimsuit.
Joe and I are from San Diego, and we had always changed under a towel after a day at the beach (which now was everyday) rather than finding a changing room. For the boys it was easy, but for Kate it was a stretch to cover everything at once while taking off her wet bikini. Kate would "accidentally" drop her towel and give me a flash of her full incredible breasts, or she would raise her hands up to tie her hair with her back to me -- giving me a brief glimpse of her butt cheeks.
It's amazing -- I saw her ass cheeks and tits in a tiny bikini nearly every day but there was still something incredibly arousing about seeing the same breast without the little piece of cloth covering the nipple, or the same perfect round ass cheeks defying gravity without the thong lacing down the middle. It was naughty and forbidden and it drove me crazy.
I think the first time she flashed me her tits might have been an accident, but seeing my response encouraged her. Soon, it became a daily game she played. Joe noticed her flirting, but he wasn't the jealous type and thought it was funny. I think he felt bad that he had taken the girl I was after and so he had made it ok in his mind for her to flirt with me as a consolation.
Joe and I would change to dry shorts and Kate would remove her wet top and replace it with a loose-fitting t-shirt or tank top. I loved how her side-boob and upper torso showed through the tank top and her perky nipples stuck out through the cloth.
