Looking back from 2009-11-06.
My Virginity Troubled Me
By the time my twelfth grade year rolled around at WPSBC, I felt that life had short-changed me because at eighteen years old, I was still a virgin! Surely, all my pals and enemies alike had, by this point in their lives, enjoyed sex many times. At least, to hear them talk about it, that’s the impression I got. So what the heck was the matter with me? Indeed, I was eager to shed this then-dubious distinction because during that age of sexual liberation, I believed that there were lots more non virgins out there than virgins like me, and I hated being in the minority.
That Older Schoolgirl
Her name was [Dawn] and she graduated some years earlier. But she remained in Pittsburgh, living just a few blocks away and working downtown for a local high tech company.
We never talked much while she was a student, though she was always cordial when I’d say hello. Yet, saying hi back seemed to be all the more conversation she ever cared to have, although admittedly, I never really pushed for deeper discussions. You see, I was rather shy then (as now too) around pretty, older girls. For one thing, she was nearly five years older (that’s a lot for an eighth grader to handle), and for another, boys never left her alone. One fellow in particular, she hung with throughout most of (her) senior high. Anytime you saw her, you’d usually see him too, and during his occasional absences, another guy would immediately move in, within hours in some cases, hoping to take his place, at least for a while, until her and the original boyfriend made up again.
It’s no wonder that so many guys liked her. She had long, straight, dark brown hair, exquisitely fair skin, and she was slender, even before thinness became a wide-spread ideal. She wore thick glasses, that gave her this intensely studious appearance. She came across as quite the prim and proper girl, and she rarely made a peep. I’ve never heard her yell or talk incessantly. So, she was mysterious, and this aroused my curiosity in her senior year though I was some years younger.
Not that her mystery itself intrigued me. But with all the more I knew about her, which was very little indeed, anything good that might happen remained possible. Since I knew so little of anything about [Dawn], I therefore detected no show-stoppers or skeletons in her closet. The sky was indeed the limit with [Dawn].
I’ve usually found that as we come to know someone — as we replace the mystery with awareness and knowledge — we typically learn things along the way that lessen their allure; transforming the beautiful stranger into the unattractive buddy at best. Indeed, until I found something severe that I didn’t like, I was content giving [Dawn] the benefit of the doubt. I just knew that we would have lots of fun together, if she’d ever give me the chance, and I never assumed that any badness existed in her until I actually saw it for myself. Nor did I look for it. The way of my heart was to form a first impression, then, if that was a good one, to run ahead, at full speed, until given a good reason to slow down. Caution, I thought, was for the old.
Thus, it was these possibilities that [Dawn’s] mystery implied, her initial beauty, and the lack of any objectionable knowledge about her that interested me. Since I knew of nothing bad, emotionally I figured that everything would be good, and my libido concurred. In those days as I said, I did not look for problems. In fact, feeling attracted to a girl was all the reason I needed to pursue her. I didn’t care about how long my infatuation might or might not last, or her history, or associations, or any bad habits that she might have, or what awful things she could possibly do to me if she had despicable morals and gained access to intimate details of my life. So I sometimes picked the wrong women, but realized it not until I had already fallen in love. Then, I’d suffer the pain of falling back out of love again, once I knew them to be less than what I’d hoped for.
Though not quite Miss America, she appeared frequently in my mind’s eye when I’d fantasize about getting intimate with a few of the older schoolgirls, as I so often did. Indeed she topped the short list of the girls I’d have taken to bed if allowed, because she was petite, soft-spoken, and gorgeous in a girl-next-door sort of way. Though definitely not a goddess, I imagined that I’d still enjoy a romantic interlude with [Dawn]. But such opportunities never arose while we both attended school as students. In actual fact, she was simply never available. Plus, though she never scoffed at me and was always friendly, she seemed forever indifferent to me. I saw how she acted toward those she really liked; all bubbly, animated, and giddy at times, yet observed none of this when she talked to me.
The Reunion
But in February of 1979, fate looked fondly upon me, and I got the chance that I’d almost forgotten that I wanted four years earlier. The weather had begun warm up, and I worked the school’s telephone switchboard for an hour each day; a half-hour at breakfast, and another half-hour at lunch. Occasionally, I’d substitute for the fellow who did the evening shift, [Morry], and he and I enjoyed a friendly rapport in those days. He and his girlfriend both knew [Dawn], and [Dawn] would often come to the school after work and sit with them during the evenings, at the reception desk, talking, playing cards, and such. This is where I met her again.
I’d see her sitting on the desk behind the switchboard, dangling her cute legs over the sides, giggling at [Morry’s] jokes, and then I became curious about her all over again. She never brought any guys with her during these late winter visits. So I guessed, hopefully, that she currently was unattached. Thus, my curiosity grew into desire and passion in just one or two of these her-alone sightings. Yep, I came to want her badly each subsequent time I saw her. Could it be that she’s finally available to come out and play?
Indeed, [Morry] picked up on my desire, and apparently, [Dawn] had expressed to him some interest in me as well. Surprising, as she never seemed intrigued by me in her school days. But four years had changed the two of us such that now, it was a whole new ballgame. [Morry] helped the two of us break the ice and get talking – I was so bashful back then, probably because I wanted her so badly. Thus I very much appreciated his help.
Her visits shortly became routine, occurring almost every night. I checked the reception desk (another name for the switchboard) each evening, seeking her, and was usually quite pleased to find her. Any time I did, I went in to chat, and she and [Morry] welcomed me profusely, each and every time.
With her so inviting, my shyness quickly ebbed, and in a week or two, I was sitting beside her on the desk. Either that, or I’d sit in a chair immediately in front of her but still close enough to feel the waves of heat radiating from her 98.6 degrees. We’d hold hands and I’d whisper lewd comments. But unlike the women I’d known so far, who tended to be somewhat reserved in such matters, she responded with risqué’ statements in kind. She was not put off by “dirty talk.” To the contrary, she seemed to enjoy it just like us teenage boys did. In fact, she dared me to put my money where my mouth was and to do the things to her that I joked so much about doing. While I would not describe these encounters as romantic, they were nonetheless quite arousing. I got hard each time she and I would engage in these playful and enticing exchanges, and before too long, she and I planned our first date.
She began telephoning me as I worked the switchboard, and call me a naughty boy for being so excited by her. But she promised that we’d be together soon, and as it turned out, she kept true to her word.
Our First Date
After a few weeks, she invited me to her apartment. This two bedroom place she rented along with a male roommate; though she assured me (and I believed her) that they were in fact, just friends. She even walked to the school to pick me up, as I had no idea where she lived. The evening grew chilly and windy as we walked with the sun setting at our backs. But her dwelling was quite warm; providing a romantic contrast to the coolness outside.
She cooked us dinner too; the food already baking and boiling when we arrived. It smelled wonderful, though I do not remember what exactly she prepared. I was quite nervous actually, because everyone knew what this date was to be about. She knew it, and so did I. Her roommate joined us for supper, and he must have known it too because shortly afterwards, he made himself scarce. Apparently, the two of them had discussed my coming and [Dawn] had asked him to leave after the meal. He did so without a grudge.
My heart thumped and I worried that she might hear it, or feel it even, should we embrace. I heard it in my ears and could feel it in my temples. I could even see the pulsations in my vision as the light went momentarily dim with each heartbeat, and then it would brighten up again as the heart muscle relaxed in preparation for the next stroke. My palms sweated as well and my knees knocked a little too. My teeth chattered a bit and I shivered despite her balminess of her dining room.
My nervousness puzzled me because I knew she would not reject me. It could not have been clearer to me that we came here so we could get physical. She wanted it, and often said it. So what was there to be afraid of? We left nothing to chance for this evening; we’d discussed going to bed together at the switchboard. Each of us knew what the other hoped would happen. Indeed, we’d both been quite open about our expectations for our “first date.” So my apprehension seemed baseless, except for the newness of the experiences that I was about to encounter. I’d never before been so close to a woman who openly said that she desired me, and perhaps I feared that I wouldn’t know how to handle myself. But my anxieties turned out to be for naught however, as nature showed me what to do and when to do it. Yes, nature took its course.
Her First Touch
She finished putting the dishes away while I waited for her on her light-colored, sheet-covered couch in the living room. Soon she came in and approached me with a sly grin. “Okay,” she said. “Here I am.” At that, I rose from the couch, swept her off of her feet into my arms, with a strength that surprised me. She was very light and now, she was giggling as I held her. “Now, what are you going to do with me?” she asked playfully. I carried her back to the couch, with a lamp at either end. Only one of the lamps glowed (the one to the left as we faced the couch) and so the lighting was at best, subdued. This was the only light source in the entire room.
I sat down, still carrying her, but soon found that she was too heavy to support indefinitely; her bony butt jabbed uncomfortably into my thighs as she sat on my lap, grinding. So I slowly moved her to the cushion beside me, and she, picking up on my cue, assisted and eased herself toward that spot without a word. She then began rubbing my shoulders, arms, and thighs; her hands gently exploring my every nook and cranny except for where what makes me a man was located. She was careful not to touch there. But after five minutes or so, I said coyly, “So when are you going to massage the rest of me?”
She said, “Ah, if I touched you there, you’d shit. Wouldn’t you?”
“No, go ahead,” I said quite eagerly but also sorry at that moment, that I had encouraged her. What had I let myself in for? Now that I’d given her the green light, she’d certainly be coming with all due haste. Oh no! But actually, she didn’t move too quickly, taking a couple more minutes getting there as she made big circles on my stomach and thighs with the palm of her right hand. Then, she switched to tracing the circles with her index finger, and these circular motions got smaller and smaller in diameter, zeroing in on home plate, the bull’s eye. Obviously, this woman was no stranger to the bedroom and brimmed with self confidence. Few if any inhibitions I saw, unlike myself then, and she gladly took the driver’s seat this evening; assertively settling into her role as the senior love partner.
Now just a couple inches away, she asked, “Are you okay? Shall I keep going?”
“Yes,” I whispered, my heart boiling over with a sweet combination of anticipation and trepidation.
Her hand found me then and oh my goodness. I held my breath, savoring yet dreading her touch. It was delicious! I wanted to moan but was afraid of turning her off. So I made no noises; self-conscious of even my breathing. I didn’t want to act as though I liked it too much. But I really did.
Jesus quickly rose then as thoughts of this older woman putting her hands in my pants ran through my mind. This wonderful yet nasty lady, who just four years earlier, I would never have had a chance with, seemed eager to get my clothes off today. I watched her hand rubbing me and working my fly, and her finger as she outlined the embarrassing bulge in my blue jeans.
Then I looked into her eyes, and she gently smiled as if to ask, “There now, that’s not so bad, is it?” But then she snapped me back to reality by sarcastically scolding, “Shame on you, you naughty, naughty little boy!” She enunciated each syllable and created still more emphasis by tapping my other head with her right index finger as if to punish it for emerging.
At this exaggerated authoritarianism, I thought Jesus would tear though my jeans; the irony of the setting drove him crazy with blissful sensation. He got so hard that he hurt as her slender and long, pale, manicured fingers stroked his head and neck, and tapped all around him through the denim. “Oh, you are so bad,” she muttered, now breathing heavily herself. “Do you like it?” she asked.
“Yes,” I gasped.
“Now, do you think he’d like to come out and see me?”
“I don’t know,” I replied softly. Now I really was feeling self-conscious, for no woman, except for my mother dressing me as a toddler had ever seen that part of me before, much less touched him. Plus, I’d often worried about not being big enough to please the girls. Now to be honest, I had no idea of just how big I had to be to get female approval. Yet to hear the fellows talk at the north side school playground over the past five years where I hung out, the rule of thumb was: the bigger the better. In fact, they’d often boasted about their sizes and how the gorgeous girls told them how wonderfully large their manhood was and how much they liked it. But while I never actually compared my size to theirs, I was virtually certain that I’d never be big enough to please anyone. In those days, I so frequently troubled over such trivial things, that my self-confidence never got a chance to flourish until well into adulthood. Back then, I was quite shy and possessed many more hang-ups than today; I was innocent.
She must have read some doubt in my face. “Oh come on,” she coaxed. “It will be fun.” She caressed him some more; teasing, tickling, and drumming with her right hand while stroking my hair with her left. Again, I’d never seen before any woman that liked me this much, much less someone that I’d admired from afar as an eighth grader in 1975; someone that back then, I was nearly certain I’d never get to love. After having been forced for so long to fantasize rather than to experience, the dreams about to come true this night frightened me. I felt the tension building in my stomach and chest, and suddenly, her non existent inhibition and aggression took on a dirty air, and I got the sickly feeling that I was about to get naked and then jump head-first into a cesspool. I became queasy. Thinking about her unzipping my jeans brought the supper I’d just eaten back up into my throat, and I struggled not to vomit.
Now at the switchboard over the past couple weeks, her consistent interest reassured me and bolstered my self-esteem. It enticed me to explore her further as I was about to do then. Up ‘til then, I’d been grateful for having this lady get so aroused over me. But her perhaps-too-open-and-abrupt expressions of horniness — her heavy breathing and moaning — made her appear trashy or sluttish, and I felt mildly disgusted at myself for allowing our encounter to occur, and I blamed her for so enthusiastically encouraging it. Of course nowadays, now that I’ve acquired a measure of experience in the bedroom myself, subsequent encounters have been much more enjoyable than this initial one with [Dawn]. Back then, I was sick with disappointment in myself, and perhaps a little disillusioned as well, as I learned that sex for real might not be as fun as it seemed in my imagination while masturbating in the suitcase room, as I’d heretofore done hundreds of times.
My Doubts
There was comfort in the fantasy but horror in the reality that was about to play out. I don’t know for sure why I was afraid besides the notion that this was the first time I’d ever actually been with a girl like this. Maybe the fact that she was so horny intimidated me. Indeed, she did not act like the prim and proper woman that she seemed to be back in eighth grade; a behavior I’d come to expect from all ladies at that point. I thought she should be the shy one; not me. But the roles were reversed because she had the greater amount of experience in bed with lovers; me the newbie, her the older, yet very warm and soft hand. I’d often heard of how males are supposed to take charge in the bedroom. But on this night, it was she who made the advances and set the tone, and I felt self-conscious, again, as a result. Why wasn’t I living up to my manly responsibilities, and shame on me for not. To me, my innocence was no excuse, and I felt ashamed of it.
What would my parents think if they knew? What would [First Love] think? [Dawn] and I were about to do something I’d dreamt of since my first orgasm by my own hand, some seven years earlier. Yet the whole thing seemed unclean somehow. Though [First Love] had avoided this kind of relationship with me all through school except for a few small moments, I thought it wrong that my first time making love would not happen with [First Love]. I wished that I’d just spent the last hour on her couch instead of [Dawn’s].
Besides, I wasn’t sure how much [Dawn] really liked me, and I was not in love with her. I was too young then, to appreciate the virtues of the kinds of casually intimate, no-strings encounters like the one we were having. So I expected that any lady, who found me attractive sexually, ought to also profess her undying love and devotion to me.
But I don’t think [Dawn] desired a long-term relationship; her heart was elsewhere. Indeed, she frequently asked how [Tad] was doing and what he was up to. As I’d answer her, I’d notice the increased gleam in her eyes. She’d turn toward me and move closer as she listened intently to my [Tad] words. Even today, some thirty years later, she still calls him every few months to chat, while I have heard nothing from her; not once in 28 years. Yes, even in 1979, I sensed that she really liked [Tad], or at least, seemed more acutely interested in him than me, and I worried over creating a competitive situation among between he and I; one that I’d likely lose.
I picked up less of that sort of interest from [Dawn] toward me, and this also gave me pause. Did I truly want to go to bed with a lady who didn’t really care about me that much? Perhaps not, because I feared that doing so might make me more vulnerable to her than she was to me, and thus, give her greater emotional power. I suspected that [Dawn’s] feelings for me ran only so deep and so, I dreaded laying my heart on the table for her if she would end up treating my feelings as casually as she seemed to regard the sexual energy between us. Not that she was cold by any means. But something warm was definitely missing from our date. The whole interaction just didn’t feel as special as I imagined it should.
Further, the thought of dating her aroused me sexually; but not romantically. Over the past month, she starred in a number of my most potent fantasies. But pursuing those desires seemed wrong if I did not love her, which I did not. The idea of taking her to bed intrigued me all right, but at the same time, the image of her coming home to meet my family repulsed me. She was great in private but I had no wish to go public.
I felt no emotional vulnerability toward [Dawn], yet feared that I might become her emotional slave if we were to continue down our current path toward casual sex. In retrospect though, I doubt that I would have fallen in love as a result of this one encounter. But at eighteen years old, and this being my first such expedition, I had no idea how I’d react, and lacked the confidence to effectively deal with whatever might happen. I’d spent the past seven years in nearly continuous pain over the relationship with [First Love]; a situation where I constantly felt exceedingly powerless, and therefore, hopeless and sad as well. Why did I regard my relationship with [First Love] so negatively? Because at this point, [First Love] desired me much less than I did her. As a result, throughout school, I campaigned to entice [First Love] to go out with me on a real date, like the one [Dawn] and I were “enjoying” this night. But this night happening so soon after finally feeling like I could get over [First Love], I was in no hurry risk placing myself in the weaker emotional position again; not when [Dawn] appeared to be more seriously interested in [Tad] than me. In short: I was scared. So I didn’t want things to go further than they had. In point of fact, they’d already gone too far.
But I Was Curious
Yet in spite of all these concerns, I kept silent. I wished not to disappoint [Dawn], and intellectually at least, if not sexually, I truly wanted to see her in the nude. That is: I still wanted to at least have the experience of seeing her that way, even if that experience would prove to be far less sexually enjoyable than I’d hoped. Again, this was a night of first-experiences, and seeing this lady in the buff would indeed be a first that I thought I might enjoy, or at worst, regret not doing later if we ended the date before she put on her birthday suit.
As an eighth grader, I often admired her legs when she wasn’t looking, and now as a senior, she was offering me an early graduation present: the chance to see them close up, and bare as bare could be. Though she lay across my lap, her legs within a forearm’s reach, I wished to explore no more. Crazy. I mean, here I was, actually living the dream that I’d played over and over while pleasuring myself in that dark suitcase room on the third floor with the creaky floor on the boys side. But, much to my shock, I could find none of the arousal that, while fantasizing, I was certain that I would find if I ever could live out the fantasy. Indeed, I got what I had wished for this night. I was doing much of what I dreamt of. But I found, upon living that dream, that I didn’t really want it. It turned out to be nothing like I thought it would be, and far less pleasing to boot.
However, I figured that if I didn’t check her out, that I’d never get the chance again. So I kept going with the flow, even though I was quickly losing interest in seeing where this flow would lead.
“Oh, what happened to him? He’s all soft again,” she said with exaggerated but nonetheless apparent disappointment.
“I don’t know,” I muttered. “Perhaps I’m nervous.” She rubbed and stroked me a little more. But the hardness would not return.
“What can I do to help?” she asked with genuine concern that seemed motivated by more than just a sexual interest. She did care to a degree, and I think that had I fallen in love with her, she would have tried to make us work well together even if she didn’t feel for me what she felt for people like [Tad].
Off To the Bedroom
“I don’t think you can do anything,” I replied, suddenly wishing to put some distance between us. I moved to get up and she threw her legs off my lap and stood up with me. Audaciously, yet against my better judgment I said, “Let’s go to your bed.” Like she, I also wondered how I could become aroused again, like before, when she touched me down there for the first time.
“Ooh!” she replied. “Okay.”
I smiled and then put an arm under her butt, lifted her to my waist-level, and carried her to her single bed in the adjacent room. She was thin and light; just like I liked, and also one of those “older” girls that intrigued me so just because they were older. Ironically, curiosity, more than desire, motivated my interest in going to her bedroom. I knew nothing about how I’d feel once there, and so, I wasn’t sure if I desired this level of encounter or not. But I did wish to figure it out, and reasoned that backing out now would deprive me, quite likely forever, similar opportunities with [Dawn]. So, I encouraged the evening to progress toward intercourse though admittedly, my heart just wasn’t into it.
I wanted to desire her in the worst way, and in fact, felt pressure to do so; though I’m sure, that did not come from [Dawn]. It was all me. I hoped I’d again find the desire for her that I’d lost on the couch earlier, somewhere now under the bed covers, and perhaps even underneath her clothes. Indeed, I had to find it to make the evening worthwhile, for I did not want to return to WPSBC with this evening described in the history books as a total bust. But so far, any passion that I’d previously felt in the reception room at school, had vanished.
The last of my hardness disappeared too as I carried [Dawn], and then I became as limp as a soggy Vienna sausage by the time I gently lowered her down to her mattress, face up. Strange too, because one would think that heading for the bedroom while carrying a very pretty and willing girl, would have had the opposite effect. Indeed, I insisted to myself that I should be as hard as a rock, and was disappointed that I was not. I believed that restoring my interest (and thus, salvaging the date) was still possible, if only I could find the missing piece; an ingredient which I was certain was there with us. I just had to find it; though I had no idea what it even was much less where to look.
I sat on the bed beside her as she removed her thick glasses while watching me with an inviting gaze. This was the first time I’d ever seen her without her spectacles, and so, I was not used to it. Now, I regretted even more, going this far because (I’m frightfully ashamed to say) I found her appearance to be quite the turn-off. With the barriers between strangers and casuals now gone, and any illusions of her beauty gone with them, I discovered that to me, she possessed no real (i.e. lasting) beauty. I never did learn to find her bare face attractive, though I struggled to for the rest of the date.
She said softly then, “Why don’t you take off your clothes?” Again, there appeared that trepidation in my heart, coupled with my lacking interest, as well as emerging feelings of guilt and shame. I deemed myself shallow and hated myself too, for so easily and so quickly becoming displeased with her. She didn’t deserve this level of rejection, because as far as I could tell, she’d done nothing to warrant it. She has always been nice to me. So how could I, aspiring to be this “sensitive new-age guy,” just cut her off like this? In fact, I couldn’t; at least, not yet. I couldn’t bear to hurt her feelings. So, I continued onward.
Though I was not horny, I encouraged her; stripping down to my underwear as she looked on, smiling with excitement, like a little girl whose parents are in the process of handing her a Christmas present, while she watches them bringing the box closer. Another first: This was the first time any woman had ever seen me undress, and [Dawn] appeared to be enjoying the view immensely, and wanted to see more. Her excitement grew as I peeled off each piece, whereas mine declined as she removed hers.
Surprisingly, I felt no embarrassment at her seeing me nearly naked. In fact, ironically, I wanted her to see me; the thought of her beholding my starkness got me a little hard again for an instant. So, I did as she asked and in less than two minutes, all that was left to remove was my underpants.
She beckoned, “Come here,” and then motioned with her right hand where she wanted me to go. So, I slid over top of her, now cheek-to-cheek, just as if we were slow dancing. Another first: I’d never lain on top of a lady before. Yet here I was, doing it. I was certainly glad to be doing it if, for no other reason, than that I could now truthfully boast to my friends that I had in fact done it. However, I found no sexual arousal in it.
My First Pillow Kiss
I hated having so many things on my list that I had yet to experience, and sometimes, friends and enemies alike would rib me for my innocence. So I was proud to now have this experience in my repertoire, even though it gave me nowhere near the thrill I’d imagined it would during all my hours of masturbating since 1972. Exchanging kisses in bed with [Dawn] made me less innocent, and that was just fine by me because this decreased naivety would give the bullies at the playground less reason to laugh. It might even make them envious; a thought I savored as I kissed [Dawn] on the lips for the first time.
But [Dawn] didn’t like lip-locking much. Now she didn’t mind the occasional pecks every minute or two, so long as they lasted no more than two or three seconds. However, the thirty-second wet kiss was out, and she absolutely detested French kissing. Sometimes I regret that my first pillow kisses happened with a girl who didn’t like kissing. Still though, she was a great sport about it, and humored me way more than her duties in this matter called for. But the hardness did not return.
I looked at her then and smiled. She smiled back and our lips met in what would become my first pillow kiss. “How can I make it better for you?” she asked.
“Oh I don’t know,” I replied. “Maybe if you took off your clothes…”
She did not object. In fact, she rushed to unfasten her pants and pull her shirt over her head, as though she’d been eagerly waiting for the right time to do this all night. Now, that right time had just arrived, and she was going to be sure and get her clothes off before the moment passed. I liked what I saw. Her body was probably about as pretty I’d imagined before, but that beauty didn’t dazzle me as it had in the suitcase room theater, where I beheld it only in my mind’s eye.
She lay back down after undressing, and as I took in her entire appearance, now undistorted by clothes, makeup, glasses, or anything else, I considered moving down her body past her legs, to her feet. Sexually speaking, a woman’s feet and legs excite me the most of any of her parts. Yet I hesitated for reasons I do not fully understand. She would have been okay with me down there. I’m sure. But the thought of worshipping her feet just didn’t seem interesting enough to pursue on this occasion, despite the many minutes of sexual stimulation this vision inspired in the suitcase room. I wasn’t afraid of asking her either. I just didn’t want to. At least, I wasn’t sexually motivated to do that.
To this day, I regret foregoing that opportunity. I never did see her feet up close, and now, I’ll likely never get the chance again being that she’s in her fourth decade of marriage and lives too far away besides.
We Assumed the Position
“Why don’t you try getting on top of me?” she suggested.
“Ummm, okay,” I said reluctantly. I felt as nervous as I had my first day of kindergarten, and about as limp as well. No hardness at all was left. In fact, Jesus had grown cold and clammy. Like a curious turtle, he stuck his head out, found out that he liked nothing he saw, and then went back in. He would not come back out this night.
Still though, I had to press on, if for nothing else than the sheer account of it; to make this experience one of my own. So, I did as she asked. She was warm. Her legs were smooth. She had no bad odors. In fact, she may have smelled of Clairol’s Herbal Essence shampoo.
We never did turn down her bed. So I never got to embrace her under the covers. But I didn’t care, because by now, the sad notion that I was not going to find “the handle” to turn myself back on, had become a convincing reality. This night just wasn’t going to get any better than a C average.
I lay above her, looking hard into her eyes, and casting my eyes up and down her pale-skinned and soft body, desperately searching for some feature of hers to get physically excited about. But after perhaps ten minutes, I had found nothing.
We talked some. She said not to worry about her roommate, as he would be gone the rest of the night. I looked at my LCD watch that Rich Parker had given me for Christmas, backlit by tritium, and saw that it was just after nine PM. She talked of going to work the next day, all the while fondling my sweet spot to no avail. It was over. We both knew it, and I felt ashamed. True. I wanted the night to go this far, before it has actually done so. But now, I regretted taking those steps. My stomach again grew unsettled.
We Got Dressed
“Well, I’d better get going,” I said with (I hope not too much) relief. Any residual horniness from earlier had long since left us both, and we were conversing as nonchalantly as two friends would, and not even very close friends at that. Whatever barriers had lowered, were quickly rising again as we each put our clothes back on. Before too long, our semi-stranger status was back. But unlike before, I never again felt physically attracted to this beautiful stranger.
We said nothing to each other as we dressed. Clearly neither of us came away with anything like what we’d hoped. Despite my persistence, in spite of my lacking sexual desires to persist, I never found anything that aroused me again about [Dawn]. Unfortunately, this evening would indeed be written into my history books as “a bust.”
I felt sorry for [Dawn], for I wanted so much to give her a good time but just could not make my body obey. I truly wished not to hurt her feelings. But hurt her feelings I did, though fortunately she never voiced any blame at me. Nonetheless, this bust would trouble me for some years, until I realized that so much of what makes good sex good, goes far beyond the choices we make and the actions we take. Those do affect it to be sure. But without the presence of some other key ingredients (like genetics, knowledge about the lover, complimentary desires and gifts, and so on), good sex just won’t happen, no matter how much you try to force it. Though I now had in fact gone through most of the motions of the sexual experience that the playground bullies boasted of, and could therefore, truthfully boast right along with them, my heart was still empty and my thirst for women unquenched.
The Date Was Done
After we finished dressing, [Dawn] walked me half-way back to the school. She said, “I’m sorry, Tom,” and that was all. We hugged our good-byes. Then I turned and scurried away as fast as I could. The wind made me shiver and my teeth chatter even though the temperatures topped the mid fifties that day. Again, I wanted to throw up, and wished not for her to see. At least now that it was completely dark, I could easily find a bush to dump into if needed.
What had I done? Had I tainted my suitcase room fantasies forever with this little excursion, with a much less exciting reality? It sure looked that way. I worried that I might never be able to enjoy masturbation again in light of the apparent un-attainability of the fantasy. Up to this point, I assumed that my masturbatory visions could happen for real if I just found the right women. Indeed, I think this is one reason these visions produced such pleasure. But now, I was not so sure. After all, [Dawn] appeared in my mind’s eye just as appealing and pleasing as any of the most attractive girls I’d ever erotically dreamt of. But in truth, she physically pleased me not in the slightest. Would it be like this always? Could I ever again count on my fantasies to point out the women most likely to pleasure me in the for-real?
Another first: This mediocre experience got me to question for the first time, whether my fantasies could ever become real. However, that uncertainty didn’t last long. Maybe I just couldn’t face the possibility that truth and fantasy often don’t agree, and that what seems fantastic, is, in reality, nothing of the kind. Maybe I just put this out of my mind because if this were the case, it’d be much harder to enjoy sex by my own hand; particularly if I thought that what I desire inside my mind could never happen for real. Perhaps the detailed memories of [Dawn] faded after a while; restoring my sexual vigor. Whatever it was that brought it back, after a few days, I returned to the suitcase room with the same high sexual energy as before the [Dawn] experience. The reality of [Dawn] only dealt my world of fantasy a small blow.
Though I hadn’t the wisdom to express this fully back then, I believe today that there are women, for real, that are every bit as desirable as those in my dreams. I found some at the foot parties earlier this year in fact. There, I met them for real. I felt them for real, and they really turned me on. The dreams can come true. However, as it turned out, [Dawn's] real image pleased me far less than did her angelic, dreamy, and imaginary portrait.
Though the outcome of this particular encounter was less than I had hoped, unfortunately I couldn’t have figured this out without doing exactly as I did, and pressing on a little with the date. When it comes to love and sexual joy, it’s difficult to know what’s behind the door until you actually open that door and walk in. Witn [Dawn], I did just that, but did not find what I sought. So I came back out again. So would I do the date over again, just as it was done, in order to find out if she could retain her beauty in my eyes after the first time? You bet.
Click here to read the next installment of this story.
Tom Hesley
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