Kays Sexual Awakening

An invitation

Join me for the story of the sexual awakening of a young woman at the age of 18. She starts as a virgin who had never masturbated or had an orgasm, and who had always thought she would not sleep with a man until her wedding night. But then she meets her new boyfriend, also an 18-year-old virgin. Over two years, an adventure unfolds in which this innocent girl becomes a sexual adventurer who enthusiastically tries everything with her new boyfriend. This is a true story: everything really happened, just as described. Some events are dramatic, others mundane, but the grit of reality is what gives this story its power and sexual heat. Come along to vicariously experience the excitement of puppy love, the fumbling first attempts at sex between a pair of virgins, the first orgasm for the girl, her growing confidence in her body, and finally the blooming of her sexuality. The story starts out innocently enough, just some kissing, but soon enough it gets really dirty. You find out how it all happened, step by step. Ready?

***

Puppy love

I had never dated a girl before I met Kay. I was a science student, graduating from high school and starting at the university. On the side, I played violin in a student-run chamber orchestra, a group of 15 young musicians. At home in bed at night, I masturbated like crazy fantasizing about having sex with women, but I was too introverted and too focused on my studies to actually ask a girl out. Years later I learned that I lie on the spectrum at the borderline between neurotypical and Asperger's, so... that explains a lot. Looking back, it's funny that I didn't realize at the time that girls thought I was super cute and admired my smarts and musical talent. If only I had known how to capitalize on that!

The harpsichord player my chamber orchestra, Kay, was a stunningly beautiful Korean American girl with a vivacious personality. She was smart and ambitious too. She had dated a whole series of boys, moving from one the next every few months. When a new boy came along who appealed to her, she just dumped her current boyfriend and started with the next one. Dating to her meant going out to dinner and the movies, holding hands, flirting, and making out with the boy when they were alone. That was as far as things went. The boys -- well, they were thrilled to have a chance to French kiss with Kay and maybe feel up her boobs. She was a catch, and they were proud to be seen with her. Especially since Kay generally picked smart, nerdy boys who had never dreamed they could be with such beautiful, spirited girl.

One December our orchestra travelled to another state to play in a competition. I boarded the bus and sat by myself, socially clueless as usual, when Kay plopped herself down in the seat next to mine and began enthusiastically chattering away to me. This continued for the entire four-hour drive. A viola player in the orchestra later told me she "practically gagged" watching Kay throw herself at me like that. Yes, although I hadn't realized it yet, Kay had picked me to be her next "boyfriend".

After we returned home, I somehow got it together to ask Kay out, although in my typical nerdy fashion, it was to go to a science event at the university. Soon, Kay and I were spending all our free time together, having lunch together every day, sharing everything. But I never made a "move" on her, much to her disappointment. For all her self-confidence in social situations, Kay believed in traditional gender roles, having been brought up by very conservative parents. So, she had to wait for me to initiate a kiss or any other physical contact. I had no idea this beautiful girl was dying for me to kiss her! Until... the kiss finally happened.

Our orchestra was at the beautiful opera house downtown, getting ready for our dress rehearsal for a festival concert at which several different student groups would perform. We were waiting for another group to finish their run-through on stage before our orchestra would have its turn. Kay and I, together as always, explored the opera house while we waited. We climbed the stairs to the very uppermost balcony and watched the other group on stage from there, totally alone up in the nose-bleed seats. We had to whisper so as not to interfere with the ongoing rehearsal, and I approached Kay very closely so she could hear me. She interpreted this as me moving in for a kiss, and her reaction was to pull me in with her arms and attack me with her mouth! I finally realized this girl had been dying for this moment for weeks, and the heat of her eagerness was overwhelming. I was tasting her, and smelling her, and feeling her breasts pressing against my chest! That kiss - it lasted a long time. The ice was broken.

From that moment on Kay and I always looked for opportunities to be alone, and when we found one, inevitably we would press our bodies together and lock lips. I'm sure it was Kay who first pushed her tongue into my mouth, but once that barrier had been broken, I eagerly explored her mouth with my tongue every time we made out. Everything in there was explored -- her teeth, her tongue, the roof of her mouth. Looking back, I feel sympathy for all the teenage girls who have patiently tolerated this type of treatment from an eager boyfriend.

The next barrier that was broken was touching Kay's breasts through her clothing. As usual, we had sought a private spot to make out. In this case, it was a small area behind a building at the university. As we tongue-kissed, Kay, so frustrated that I hadn't done this yet, grabbed my hand and placed it on her boob, making a point of increasing the urgency of her kisses to show me how much she wanted this. She was wearing a blue cashmere sweater, incredibly soft, over a bra. The memory of that sweater is burned in my mind. Kay had lovely B-cup breasts, and after the literally years I had masturbated dreaming of the pictures of breasts I had seen, I could not believe this was actually happening. Like tongue kissing, boob fondling became something I did with Kay every chance I could, increasing even more my motivation to find times to be alone with her. In retrospect, I think Kay's previous boyfriends must have already fondled her boobs during their make-out sessions with her. So, as incredible as this experience was for me, this wasn't breaking any new barriers for her. However, at this point we had reached the limits of Kay's experience with flirting, kissing, and petting -- she had never moved beyond tongue kissing and boob fondling.

Kay lived with her conservative parents, who expected her to someday marry a Korean boy and to preserve her virginity until marriage. They forbid me from their house -- a white American boy could not be tolerated as their daughter's boyfriend. I also still lived with my mother, who similarly did not approve of Kay. So, it was forbidden love, like Romeo and Juliet.

It turned out I was a very different boyfriend from Kay's previous beaus. I made it clear to Kay that, just as I was deadly serious about my studies and my music, I was also serious about her. When I did something, I did it all the way. There would not be any moving on from me when she met some other cute boy. Kay was so attractive that other boys often tried to woo her. I showed Kay that I had zero fear of her taking up with these other guys: I even invited them to come do things with me and Kay! I established to Kay that I was completely confident that she was "mine", and this was something totally new to her. A guy who she could completely rely on, who was committed to always be there for her, and who seemed to be 100% secure in his relationship with her. Today I know that this seeming confidence was just a manifestation of my cluelessness, the Asperger's in me. But to Kay this seeming confidence was...attractive! So, we were a match and our relationship ended up going on for two and half years, only eventually ending when our career ambitions led us to pursue opportunities thousands of miles apart.

The two virgins have sex

I had been masturbating and looking at porn for years, trying to learn everything I could about sex and women's bodies. Kay had a different experience altogether. She had never masturbated or had an orgasm. But almost every day she was pressing her body against mine and feeling my tongue in her mouth as my hands explored her boobs. She had the body of a woman, and she was beginning to feel physical and emotional urges that were new to her. Despite her overall social confidence, because of her conservative upbringing she could not bring herself to talk with me about sex. It turned out that while talking was hard, sometimes action was easier for her.

One night, I walked Kay back to her apartment late at night after a date. Of course, I couldn't go in her house with her, but she told me to wait outside, below her second-story bedroom window. A few minutes later, the light went on in the window, and there was Kay, wearing her nightie. This was the nightie I would come to know so well, the one I still think of all these years later. It was deep purple terrycloth, floor length, with straps that left the skin of her shoulders and a bit of her cleavage exposed. Underneath her nightie, Kay wore...nothing. Kay opened her window, smiled, and shout-whispered to me. She told me to stay where I was. Minutes later, Kay came outside, wearing a jacket over her nightie, carrying the keys to her parents' car. We got in the back of the car together and started making out. The jacket came off. This was just like all our previous make-out sessions, except...Kay had nothing but a nightie on, and it was totally private in the back of a car out in a dark parking lot. I felt her boobs through the terrycloth that was so much thinner than any clothing I had felt those boobs through before. And Kay was kissing me with a level of passion that was also new.

This was my chance. I slid my hand under the top of her nightie, right where her cleavage was showing, and cupped her bare breasts. They were so soft, and her nipples... oh my! The intensity of her kisses increased -- she wanted this. So, my hand kept exploring, lower. Down her belly, until I felt her shockingly soft pubic hair, and then the folds of her lips below that. She kept kissing me. And... I panicked. I withdrew my hand. All these years later, I'm still disappointed with myself for this. We kissed a bit more, and then Kay went back inside, and I went home. But a new barrier had been broken.

Not long after, I was again dropping Kay at her place after a date. I had an appointment to get to, so we needed to say our goodbyes quickly. While we had been heading to her place, Kay was gossiping to me about another couple our age who had recently started having sex. Kay loved this type of gossip. As I kissed Kay goodbye at her door, she tried to finish our conversation by flirtatiously saying "Would you want to have sex with me?" This was not meant seriously, it was just Kay's way of having fun, teasing me. Kay and I had never discussed the idea of the two of us possibly having sex, despite my recent exploration of her body with my hand. My response to Kay's teasing question was not in the flirty tone we had been using in our conversation up until that point, because to me this was a deadly serious issue. I looked Kay right in the eye and said with complete sincerity "Yes, Kay, I would love to have sex with you." Glancing at my watch and seeing I might be late for my appointment, I quickly kissed her and ran off.

When we saw each other next, the issue had to be discussed. Kay told me about how she had been raised in a conservative family, taught premarital sex was not for her, and that she was shocked by my serious answer to what she had meant as a joking flirt. But now she knew that I wanted it - I wanted her. The subsequent conversations are a blur, but ultimately, we decided together to "do it". My clearest memory of this period is going to the local drug store with Kay to buy condoms. We found out when we got to the condom section that there was an amazing variety on offer. Lubricated or not? Ribbed "for her pleasure"? Reservoir end? Natural sheep membrane or latex? We had no idea. We chose non-lubricated, reservoir end, latex. What was lubrication for anyway? That sounded gross.

The chosen day arrived. We knew all of Kay's family would be away from home for hours, so we had complete privacy in her bedroom. We lay next to each other on top of the covers of her double bed, kissing, fully clothed. Moving slowly, I removed her top, then her jeans, leaving her in her bra and panties as we continued to make out. It was time for Kay to start to undress me. Kay looked me in the eyes and told me she was nervous. In an epic fail I will regret for the rest of my life, the best response I could muster at the time was "Don't be". She slipped her hand under the waistband of my pants with the objective of fondling my cock. Well, there was very little room inside my tight jeans, and my erection was already taking up what little space was in there. So, the attempted fondling was uncomfortable for both of us. None of the rest of the sex went any better. When I finally inserted my cock in her, it did not feel good for her or for me. Despite my years of looking at porn, I had no idea that sex required lubrication, and neither our condom nor Kay's pussy had any-- she was too nervous to be turned on. But despite our awkwardness and the fact that our inexperience prevented the physical acts from being at all pleasurable, we loved each other. We were having a once in a lifetime experience, together, and that was what mattered to us that day.

The next day, we talked about what we had done, and how we felt. Kay told me that it had hurt and that she still felt sore "down there". I turned beet red when I realized I had been hurting her but had been too clueless to realize that as it was happening. I somehow had thought her heavy breathing was passion, not a reaction to pain. In yet another epic fail, my response was "Why didn't you tell me?" There are moments in life you wish you could relive. How do girls put up with teenage boys? Well, somehow this girl put up with me. We did love each other, and in our minds, that first time together wasn't a failure, it was just a first attempt that we were going to repeat until we got it right. So, the sex kept happening, every chance we got. And it did get better, slowly.

Kay's sexual awakening

My memory of the next weeks and months is a blur. What I have for you is fragments, the most memorable moments that I've kept alive by rolling them over and over in my mind. Since we both lived with our disapproving parents, our sexual exploits often occurred at night after our parents were asleep, when one of us would walk over to the others' house (a good mile or two) and climb in the other's bedroom window. Kay's bedroom was in the basement, and I would squeeze through a small window just above ground level and down into her bed. My bedroom was on the first floor, and Kay would clamber up and into my window, stepping down inside on a chair I put there for that purpose. The entire encounter had to be silent, nothing above a whisper, to avoid being detected by our parents. We would explore each other's bodies for an hour or two, fall asleep, wake up at 5 in the morning to an alarm, and then one of us would have to climb out a window, trek home, and climb back into our own bedroom. We were constantly sleep deprived from these nighttime adventures.

I loved it best when I spent the night at Kay's. She normally slept on a stack of two twin mattresses that lay on the floor. When she knew I was coming over, she would prepare everything for my arrival. The two mattresses were unstacked and placed next to each other to make a bed big enough for two. When I arrived, Kay was always freshly showered and wearing her purple terrycloth nightie, with nothing underneath. As I lowered myself down from the window into her room, her arms would close around me in a warm embrace. We kissed, and... well, I was a horny teenage boy. So, I put my tongue in her mouth, and simultaneously lifted her nightie and inserted a couple of fingers into her pussy. She had been anticipating my arrival, and her pussy was always wet. Every time, my first words to her were to whisper in her ear that I loved so much that her pussy was already wet for me.

I need to tell you what Kay looked like. Her face was beautiful - not just pretty - I mean beautiful. She was a full-blooded Korean, about 5 foot 5, with straight black hair that hung down just below her shoulders, and a lovely smile. She had an hour-glass figure: B-cup breasts with reddish brown nipples, and a very narrow waist that broadened out into feminine, womanly hips. Her pubic hair was jet black. The hair in the bush above her pussy was long and so soft -- I loved to run my fingers through it. When she removed her panties sometimes the long hair was matted, and other times stood up on end. Down below around her pussy the hair was sparse, naturally: she did not trim or shave it. She had light brownish skin that grew darker around her pussy. Her inner pussy lips were thick -- I loved to squeeze them between my lips. And her little clit became visible if you lifted up the hood that covered it.

We explored each other's bodies. Kay was nervous at first, both about showing her nude body to me and about seeing me naked. So, every night I came to Kay's bedroom, soon after my arrival, I positioned her lying on her back, gently spread her thighs apart, crawled between them, and spent the next 30 minutes or so gently fingering and licking her pussy, reaching up to play with her breasts. I told myself that I was helping her by doing this, that I needed to help Kay become more comfortable showing her body to me -- only if she could learn to relax and be more comfortable being seen naked could she enjoy the sex more fully. The truth is that after my years catching little peeks of women's pussies in pictures from porno mags, I had a real live pussy I could examine as much as I wanted, and I took advantage of the opportunity. I was fascinated by every detail between that girl's legs.

Eventually we would put a condom on my cock and I would fuck Kay's pussy and come, and then we would snuggle and kiss, feeling close to each other. Kay was very eager to have sex with me and seemed to love everything about it. But I had no idea whether she was having orgasms and was still too shy to talk to her about it. She breathed hard and had strong physical reactions when I licked her and fucked her, but was she coming? Well, of course eventually we talked about it and things became clear. She did not have orgasms for the first few weeks, even though she experienced pleasure and enjoyed herself thoroughly. She had never masturbated, and it took her a while to be able to relax and let herself go with me, and to figure out how her own body worked. When that first orgasm finally happened, she was still so shy and reserved that she didn't tell me, and I was too inexperienced to realize what was happening!

But those orgasms became a regular thing, and she stopped trying to hide them. She was still very quiet when she came: we had to be careful that our parents didn't hear, after all. I joked with her that I only knew it was happening because she made "funny noises". I'd tell her "Kay, tonight you're going to make funny noises!" Her orgasms did not happen easily -- I would lick her or use my fingers on her clit for 20 minutes or more to work her up to one. After an orgasm she needed to rest, and giving her a second orgasm would take the same long work up. But... I just loved making her come, it was the highlight of the experience for me. So, I made Kay come first, at least once and usually more times, every time we made love. And Kay bloomed sexually before my eyes after those orgasms started. Her enthusiasm for sex, already high, went through the roof!