The Usual Disclaimer: This is a work of fantasy. All characters featured in sexual situations are over 18. The characters in these stories are fictional. Any resemblance to actual persons living, dead or undead is purely coincidental. Do not try this at home.
This story started out as two paragraphs in
The Outsider
, but it didn't really fit within that story. I liked the characters and the chemistry between them, so I kept writing it as a separate story. Thanks as always to my friends who reviewed this story for me. In particular, I need to thank Pat, who pointed out a glaring hole in the plot.
* * * * *
I was best friends with Kevin since about the third grade. I always thought his mother was pretty, but I never would have imagined anything would happen between us. She was incredibly strict and prudish, and if you had told me I would fall in love with her I would have said you were crazy. I never saw her wearing anything that would give away the marvelous curves of her body. It wasn't until I was eighteen and started having sex that everything changed.
I was a virgin until well after my eighteenth birthday. Oh, it wasn't like I had never dated or kissed a girl, but I hadn't gotten much further than that. In retrospect, I guess I had been operating under the assumption that women just weren't interested in sex the way guys were. The obvious clues that women were interested in me went unnoticed, because I simply wasn't looking for them.
Before I go any further, I should explain that I had to repeat the seventh grade. I got really sick a few times that year and missed a lot of school. I was pretty big for my age, and I was a basketball player all through junior high and high school. I started on our varsity squad my freshman year. Most of my friends from childhood were still my friends in high school. They were just a year or more ahead of me in school.
That was why, when I was eighteen and finally got laid for the first time, I was only a junior in high school. The girl I was with was nineteen. Tamara had gone to our school, but she had graduated the year before. I ran into her where she worked, and we had a nice chat. I missed the obvious signals, like when she laughed a little too hard at my jokes, kept saying, "You're so funny," breathily, and her subtle glances at my body. She invited me over to her apartment after she got off work, and I went along just to continue our conversation. I still had no clue she was interested in me.
I was completely gobsmacked when she started kissing me on her couch. When I got over my surprise, I eagerly returned her kiss. When she got up and dragged me back to her bedroom, I couldn't believe it was happening. My eyes were wide when she stripped right in front of me. It was the first time I had seen a woman's breasts, and Tamara's were mouth-watering.
I would love to say, "It was magical and perfect," but it was far from that. It wasn't Tamara's fault at all; I just didn't know what I was doing. Still, it was my first time and Tamara was lovely. I was a klutz and it was fortunate I didn't injure her.
When she lay back on the bed and slipped off her panties, I could not take my eyes off her pussy. I leaned in closer and then I started to lick her. I was doing it wrong and I was sort of jabbing her with my index finger. She looked down at my face and it was obvious from her expression she wasn't enjoying it.
"Steve...What are you doing?" she asked.
I felt like an idiot. "I'm sorry, Tamara," I stammered. "It's my first time doing this. I thought you'd like it."
Her expression changed in an instant. "Oh!" she said softly, and her eyes went wide. "Wait. You've never licked anyone before, or never had sex before?"
I blushed. "Any of it," I replied.
A lot of what happened is clear to me in retrospect, like the way Tamara took over and tenderly made love to me. She gently told me what to do as she rolled over on top of me in her bed and guided my hard cock into her. I thought she was being bossy and selfish when she directed me how and where to touch her, and when to speed up and slow down when she spread her legs for me. It wasn't until much later that I figured out she was trying to be helpful and make me a better lover.
I sought her out early in the summer to thank her and apologize. By then she was engaged, but she had such a loving expression on her face that I had to wonder how it could have been if I had stayed with her.
Once I started to figure out that women might actually be interested in me, though, I started seeing the signs more and more often. Less than a week after that first time with Tamara, I had my second time with a girl in my high school that I had long fantasized about. Gabby was a lab aide for my chemistry class. She had always seemed so much more sophisticated and clever than other kids our age. When Gabby carefully guided me through how I needed to use my tongue and lips to please her pussy, I followed her instructions carefully. She told me I was "a natural" after I got her off several times that way, and it made me proud.
Gabby lived up to her name. After that one time with her, I was approached by several girls who were keen to have their pussies licked. I fucked all of them as well, and started learning how to get women off repeatedly before my own orgasm. Usually I got a second or third time with each of those high school seniors, but all of those were just hook-ups without much emotional attachment. Some of those girls had on-again, off-again boyfriends they went back to. Some of them had cheated on their boyfriends with me.
I dated two girls after that initial barrage of quick, meaningless sex. Valerie and I were together for almost a month. We got busted having sex at her house, and her parents were furious. My parents were upset, but they tried to be reasonable when they sat me down after they got that angry phone call from Valerie's parents. They explained that I had to be more responsible, and that led into a longer and more embarrassing discussion about safe sex. Valerie's parents were adamant that she could not see me again, and that was the end of us as a couple.
A few weeks later, I started dating Kylie. We only lasted two weeks before she dumped me and got back with her previous boyfriend. Later on she would confide that it was a mistake, but she had loved that guy for a long time. When I was with Valerie and Kylie, we had sex almost every day. I probably learned more about pleasing a woman from those two girls than all the rest combined. I also learned how to read a woman's body language and gauge her arousal, which would prove useful when I met other women who were interested.
After Kylie, I had several more brief hook-ups before I dated Leslie. We were much more serious as a couple and continued dating until well into the summer. By then she had graduated, and she would be going away to college. It made sense that we should break up when she left, but it still hurt when it happened. What made it worse for me was that my family acted like it was a good thing that Leslie and I broke up.
This is another thing that I can look back at and know that I completely misread what was happening at the time. I was heartbroken after Leslie left, and my family tried to console me and let me know I would be alright. I was just overly sensitive and thought they were bad-mouthing Leslie.
I thought my mother said something snide about Leslie, and I blew up. Again, in retrospect I know my mother simply misspoke. She didn't mean to imply that Leslie wasn't good enough for me, but that was how I took it. When I snapped at her, Dad immediately stepped in to try to calm me down. I thought he was taking Mom's side, and I yelled at him too. My dad has a bit of a temper, so that didn't go over well.
