It'd be fair to say that I'd wanted to be with Kara Mendel for better than ten years before a real opportunity presented itself. It wasn't for lack of trying though.
We'd gone to high school together, I met her when we were both in 10th grade. An oddity of the small private school we'd both attended was that students tended to be grouped together freshman year and attend the same classes and activites throughout their entire school career. The school was very small - it was rare for a graduating class to number even 100 students, so that made it all the more intimate.
With all the time we spent together in class, studying, and socializing outside of school, there was never any hint of a sexual connection between the two of us while we were classmates. Strange, because even back then she was quite a sight to behold.
I didn't meet Kara before she hit puberty, so I never knew her when she didn't have a woman's body. Unlike many of the girls in our school she wasn't skinny as a rail, she had an hourglass figure the whole time I knew her. While her hips were maybe a tad wider than most of the girls our age, she was tall, about 5' 7", and more than proportional up top, sporting C's bordering on D's even back in adolescence. Despite this fact and that I preferred blondes like her, I was never my nervous shy high school self in her presence, I managed to act like a normal human being around her, unlike most of the other girls I thought were pretty.
We counseled each other through a number of puppy love crushes, but never even considered the possibility of being something more in those days. Well, at least I didn't. I can't speak for her though she certainly had her share of suitors at the time.
After graduation, she took a year and traveled Europe, spending quite a bit of time and eventually being accepted into school in Switzerland. We kept in touch via email, and she generally made it back for the holidays. I moved out West for school and ended up getting my first job out of college in San Francisco.
A few years later, we both found ourselves living back in our hometown, and renewed our friendship, still strictly platonic. We were both involved with other people at that point, and eventually I got an invitation to her wedding. She was completely smitten with the guy, and they seemed happy together. Even so, a week before the wedding, I got a call from her on a weeknight asking if we could have a drink. She came over to my place and I drove us both to one of our neighborhood hangouts.
I hadn't actually seen her in quite some time and she looked fantastic. She'd been getting in shape for the wedding and she seemed more alive and vibrant than ever. She had been given a bag of candy as a pre-wedding present and offered me some. I munched on some Pez while she put on a candy diamond ring. We sat at the bar and talked about our lives, and she confided that she was not without some doubts about her marriage. As it did sometimes, the conversation turned sexual and she suddenly asked "Do you think it's okay to cheat?"
The short answer for me was "No." I came from a broken home and had seen firsthand what infidelity can do to a person's life, and was strictly against it. As we continued to talk, I realized that for the first time in all the years we'd known each other, she was coming on to me.
As we sat in the bar, I felt myself starting to wake up a bit downstairs. I was definitely not going to be standing up anytime soon without embarrassing myself greatly. She had moved closer and begun to act suggestively, touching her hair, my face, and frequently leaning over to whisper in my ear. Initially I thought she might have been a little tipsy before I noticed there was only diet coke in her glass.
As difficult as it was, I made the decision that I wasn't going down this road, and somehow managed to diplomatically make clear that point. I may have considered a frank conversation with her about getting married if I was single but I was in one of the first apparently healthy relationships I'd ever managed. We chalked it up to pre-marriage jitters, and I dropped her off at her car, which was across the street from my apartment.
She had been sucking on her candy jewel ring, and made one last attempt to garner my interest by making a show of first licking it suggestively and finally putting the whole thing in her mouth and sucking hard. My soldier once again stood at attention and this time she had no compunctions about visibly noticing it. Before I knew what was happening, her hand was resting on my leg, pulling my pants tight around my throbbing hard on.
It took all of my self control not to jump her right there, but I just couldn't do that to the girl I was dating or to her fiance. I moved her hand back, told her I would always be there as a friend, and she reluctantly got out. After pausing to collect myself for a moment I pulled my car into the garage. The rest of my evening consisted of imagining an alternate ending to the encounter by myself in bed. In fact, for years afterwards that story was a regular headliner in the movie theater of my mind during "alone time."
She got married and was happy for a while. I broke things off with my then-girlfriend not too long afterwards - it just wasn't going anywhere. About a year later I started dating a woman named Susan who I thought I might marry. We were compatible in many ways, though the relationship was far from perfect. After we'd been together a few years her mother got sick, and she started traveling to Kansas fairly regularly to care for her. We would talk each night and occasionally I could persuade her to play around with me on Skype, but she never seemed to enjoy it the way I did.
One night while Susan was in Kansas, a few friends from school were in town and we organized an impromptu reunion. Despite the huge group of old friends and the din of the club we'd somehow thought would be fun to hang out at, Kara and I managed to spend a long period just talking to each other. Her husband Jerry was out with his own friends, so neither of us had a date. We ended up sitting across from each other at a long table.
Looking back, I don't remember how we got on the topic, but our conversation got very deep in detail about our masturbatory habits. She confessed her sex life with Jerry was not exactly smoking, and as such she'd acquired a wide array of toys. I sat transfixed at the thought of this beautiful woman taking matters into her own hands. Her looks had only gotten better with age - her breasts were fuller and she carried herself with a sexiness and confidence that only comes from maturity. She told me of the various items she had in her collection, and seemed disappointed that I'd never partaken in a fleshlight or any other such device.
We both fessed to our porn viewing habits, and I even admitted that one of the most intense "sessions" I'd ever had was following that night in the car. She told me she'd gotten herself off twice before she even got home after I dropped her off. That led to my confessing that I absolutely adore watching a woman get herself off. It's easily one of the most wonderous things on the planet in my mind. The only thing I might possibly find more intoxicating is watching two women together. I have plenty of porn clips on my hard drive, and one of my favorites is a scene where two women finger each other to simultaneous orgasm. Something about that is just overwhelming to me. She then followed that tidbit up that she has a folder of Japanese Bukakke porn on the laptop she takes to bed with her, because she loves to watch guys jack off.
As far as either of us were concerned we were the only ones in the club from that point forward. She told me she liked to use her big purple dildo in her living room while Jerry was at work, and she knew the woman who lived across the street could see. I told her I'd liked to play on webcams and my lube preferences before I'd gotten involved with Susan. I couldn't see clearly across the table but one of her hands had vanished underneath the tablecloth. I was transfixed watching her cheeks flush as her foot kicked off her shoe and started to brush against mine, up my leg, and into my lap while all ambiguity in what she was doing vanished. Her gaze had gone into a thousand yard stare for a moment, but she felt the effect her ministrations were having in my pants her eyes locked onto mine.
I honestly have no idea where the evening would have gone if my cell phone hadn't gone off in the middle of that reverie. I looked down to see "Susan" with a little heart icon next to it. The spell was broken but neither of us ever forgot what had happened.
Life went on. She went back to Jerry, I went back to Susan. We never spoke of it again.
One Friday night almost three years later I got a call.
"Hey, it's Kara."
We hadn't talked in awhile.
"Hey! How are you?"
