My First


There are, I believe, three monumental events in the life of most teenage boys. Graduating high school and turning eighteen years of age are two of these, as both are regarded, in their own way, as making the transition from a boy to a man. However, the third, and certainly considered the most important by those who desire to experience it, is the losing of one’s virginity. It is not for nothing that for a young man to lose his virginity to often referred to as “becoming a man,” and it is hoped by most that this method of becoming a man will occur before the other two. By the time one graduates high school or turns eighteen, whichever comes first, it is hoped that the loss of virginity has already happened, and that when a young man is thrust into the world, he will not be completely inexperienced in matters of sex.

Because of the seemingly earth-shattering significance of losing one’s virginity, everyone has their own story of this occurrence, and it seems that everyone regards their own personal story as one worth telling, for the simple fact that the loss of one’s virginity can only happen once, and nothing experienced previously can prepare one for this monumental occasion. But such stories are rarely interesting, due to the similarities of most of them, and the lack of storytelling skills on the part of the teller, with the resulting inability to make the minor details seem greater, and thus, differentiate their own experience from that of virtually everyone else. Simply put, the story of a young man’s loss of virginity is only, in most cases, likely to be interesting to himself, especially if the experience of the listener seems eerily similar. For a story such as this to seem remotely interesting, it must be unlike the vast majority of other such stories. My own story, which is soon to follow, will perhaps serve as one such example. I can state, with some assurance, that few can claim a story like my own, and therefore, I believe that it is worth relating.

I must caution the reader that the following story will be difficult to believe, and there is nothing wrong with that. The reader is free to believe whatever he or she regards as reasonable. That said, I also caution the reader that whether or not he or she believes the following story is irrelevant. I am not relating this in the vain hopes that the reader will take the whole story as truth. That is simply not the point. The point of this is to simply inform the reader of an incredible experience that, in many ways, has shaped me as an adult male. The reader is left to their own devices concerning whether or not they wish to regard this story as truth or not.

In the three aforementioned methods by which a teenage male becomes a man, I am afraid that my 18th birthday and my graduation from high school were, respectively, the first and second methods that I experienced. I was never regarded as particularly handsome, or charming, or cool. I was not especially ostracized by my peers, so please do not get that idea. I was not bullied, at least not often, and when such a thing was attempted, it rarely went in favor of the aggressor. It would be most accurate to state that I more or less just faded into the background. I felt rather comfortable there for the most part, but in matters pertaining to the opposite gender, I wished there had been some method by which I could have made myself more noticeable, but no such methods were clear to me at the time. I had had few dates, no real girlfriends, and my high school years seem to pass me by without me learning all that much about the female of the species.

Like so many others, I consequently got most of my ideas about sex and girls from pop culture, particularly the movies, and in such movies, as the reader perhaps knows well, the loser, geek, outcast, or what not always seems to get the girl in the end. Being young and predictably naïve, I hoped that such would be the case in reality, but let’s just say that this was an early lesson on how disparate the movies and reality could be. After I graduated, I felt as though I was a failure, something less than a man if you will. Events, before much longer, would take the reins and thrust me into a situation that I could not have predicted, and allowed me to achieve manhood in not only a rather uncommon way, but in a way that few would believe, and consequently, I have never spoken or written of that day in any real detail prior to writing this.

About two weeks after graduating, I had begun to relax and shake off four years of tedium and frustration as I looked towards the future and another four years of education. My parents, now that I was out of school, had decided to take some time for themselves, which they rarely ever did, and take a vacation, just for the two of them. They went on one of those tours of Europe that lasts a month, and I was initially quite ecstatic, believing that I was going to have the house to myself for that time, my first real taste of personal freedom. My hopes were dashed when I was informed that they were çanakkale escort not willing to leave my on my own for that long, and that they had already made arrangements with a co-worker of my mother’s to put me up until my parents returned from Europe. When I heard that I was going to be living for that time with Alice Pike, I was less than impressed.

Alice Pike (which I confess is an alias) was a divorced woman in her early 40s by this point, and had been a friend of my mother’s for at least a decade by that point. I knew her quite well, as she was a regular at the dinner table, both when she had been married and afterward. To say that she had dazzling beauty would be greatly overstating the matter. But that said, she was an attractive woman with darkish blond hair and eyes that somehow hovered between green and brown, and tended to keep her hair in a ponytail. She looked, for want of a better description, more like your favorite aunt than the sexy older woman. But physically speaking, she had a great deal to recommend her, but I had found her uninteresting for any reason other than that, if for no other reason, than when she and my parents spoke, it was about all manner of things that an average teenage boy would regard as boring. We only spoke in the most polite of manners, such as a simple greeting when she came to the house, and a farewell when she left. She sometimes, when my parents were otherwise occupied, asked how school was going, or if I had my eye on any particular female classmate, things of that nature. That was about the extent of our association. I wasn’t particularly looking forward to spending a month with her. I had nothing against her, it must be stated. After all, she was a good friend to my mother, and therefore, I had a degree of respect for her. But I didn’t know what an eighteen-year-old kid and a forty-something divorcee would do in the same house for a month. I did not relish the slow passing of roughly thirty repetitive days.

I will not bore the reader with meaningless details, but suffice it to say, my parents caught their flight to London to begin their lengthy excursion, I drove my own car to her house that same day, and knocked on the door. I was shown to my room, a Spartan guest room that likely saw little use, and my month of boredom began. Her house was a nice two-story, and the only one in a cul-de-sac, which allowed for much privacy but probably compounded her obvious feelings of loneliness, to which I attributed her willingness to put me up while my parents were gone.

I wasn’t disappointed at the house. She had a pool in a rather spacious backyard, with a hot tub underneath an awning, both of which I expected to use a great deal. But for the first few days while she was at work, I drove out to my few friends’ houses to hang out, play video games, and generally do what young people do. It was the first Friday that she came home a bit early (which did not surprise me, as my mother tended to come home early on Fridays as well). She simply walked in, put her purse and keys on the kitchen counter, just around the time that I was about to head upstairs to change, as I intended to hit the pool. It was an unusually hot day after all, even for early summer.

“Hey, Alice. How was the office?” I asked.

“Nothing interesting, John. How about your day?” I confess that I use an alias in place of my own name for the sake of maintaining the flow of the story.

“It passed, I guess. Didn’t do much of anything interesting. I’m going to splash around for a bit, though. Scorcher today. You?”

“Going to get out of these work clothes and start thinking of something for dinner. I doubt I can cook like your mom can, but I hope I’m not too terrible at it.”

“Not at all, Miss Pike.”

“Still? You can use my first name, you know. There’s really no need for formality while you’re here. I’m a friend of your mom’s, not one of your teachers.”

“Okay, Alice. It’s just weird. I never address adults by their first names. Wasn’t raised to.”

“You’ve graduated, and you’re eighteen. You are an adult, John. It’s okay to talk like one.”

That was the end of that conversation. I headed upstairs to the guest room throw my trunks on and grab a towel, partially closing the door behind me. I kicked my shoes off, pulled off my pants and socks, and tossed my shirt on the bed. I stripped off my underwear and dropped it to the floor, reaching for my dark blue trunks at the same time. I had just raised one leg to put them on when, and I can think of no better description, the door flew open. I barely registered what happened next, so sudden as it was, and certainly unexpected.

I found myself forced into a seated position on the bed with my trunks falling off my leg, with a hand holding the back of my head and another working its way up my other leg, and strong kisses all over my mouth, cheeks, and nose, along with sounds that I had never heard from any source other than a movie. I can only describe it as an unrestrained whimpering, as though someone was unable to contain a severe bout of desperate passion. I apologize for the poor description, but words fail me in this instance. I expect that if the reader has ever experienced a rather intense carnal encounter, the sound in question would be well known to them.

After about three or four seconds, I still wasn’t completely sure what was happening. I was surprised beyond measure and even somewhat disoriented, but quickly enough I was able to determine what precisely was happening, though my mind remained unable to grasp the reality of it.

I heard Alice’s voice, deep and passionate, speaking with her lips still pressed against my closed mouth. “Oh my god, John. Give it to me. I need it…I need it so badly…”

My vision, which had gotten blurry around the edges, managed to sharpen in another second or two, and Alice came into focus. She was sitting on my upper leg, rather as though it was a saddle, with her chest pressed firmly against my own. Something seemed to be rubbing with some strength against my chest as she moved, and despite having no experience in such matters at the time, I quickly realized that what I was feeling was her erect nipples moving across my chest.

My only clear thought in those few seconds was, “Is Miss Pike, or rather Alice, naked and rubbing against me? Is this real? Can this seriously be real?”

And it was. But just as I was only beginning to realize the full extent of what she was doing, she seemed also began to take notice of her actions. Her face pulled away from mine and she stared me right in the eyes, her own beginning to fill with tears. Her expression could only be described as utter shock, shock that matched or surpassed my own. Alice stood up quickly, as though horrified, or at least embarrassed at what she had done, and backed away. That was when I saw that, apart from a pair of sky blue panties, she was naked. My penis stiffened completely in barely a second, though I barely noticed the sensation.

In the next second, I was able to unconsciously take in the full view of her. She had surprisingly shapely legs, a curvy body, and firm, sizable breasts that she quickly concealed as she clamped her hands over them. Looking as though she was about to scream, she turned and ran out of the room. I remained alone in my room, naked, sitting on the bed, surrounded by my clothes, and with my swim trunks on the floor in front of me, for several seconds, still struggling to believe that what had just happened was real, and just what in the hell I was supposed to do know. Stay in my room and see if she wanted to come say something about what she had done? Follow her and try to get her to talk about it? Would either smooth things out, or make things worse? Was there a right or wrong thing to do here, or had she already, in a matter of seconds, pushed things well past such considerations? After ten more seconds (perhaps, even a minute, as time seemed to be moving at a rather odd pace around then), I stood up and grabbed the bath towel that had been lying on the bed, wrapped it around myself, and headed after her, with no idea whatsoever of what I was supposed to do or say.

I headed out the door and saw that a pile of her clothes was lying in the hall. A pair of beige pumps, a pair of stockings, a blue bra, a white collared shirt, and a gray business suit, dumped on the ground as through dropped there in haste. Still confused and a little disoriented, and knowing that things were about to get a great deal more awkward than they already were, I headed towards her door, which, I quickly saw, was wide open. With my trembling left hand holding up my towel, I walked in and saw Alice, sitting on her bed.

Her elbows rested on her knees and her face was in her hands, muffling what I believed to be low sobs. She took no notice as I walked in. I had no idea what to do, or if there was a course of action that could defuse everything right away, but I thought it best to assure her that I wasn’t going to take any kind of drastic action. Besides, I was not displeased to see how wonderful she looked naked, or close to naked, and I genuinely wanted to see why she had done what she did. All I could do was shoot from the hip and hope that the next three weeks wouldn’t involve us hiding in our respective rooms from each other.

I sat down next to her, towel still held loosely around my waist, simply put my arm around her. She had not donned any sort of clothing, though she was largely hidden behind her shaking arms as she sobbed. Alice had not heard me enter, as when I put my arm around her, she almost yelped. She realized I was there and turned to face me, with her hands now clasped firmly over her breasts. Her expression could only be described as apologetic.

“Miss Pike? I mean, Alice? Are you all right? I mean…what…”

“Oh my god John, what did I just do? I…oh hell. I didn’t…oh god. I just saw and…”

I tightened my grip around her shoulder. She made no attempt to remove my arm.

“Alice? What…why did you…god, I don’t know what to say. What was that? I mean, what did you just do? Why did you do that?”

“I’m sorry, John. I’m so goddamned sorry…I just…I couldn’t help myself. I couldn’t stop. By the time I even realized what I was doing, I was already…oh my god, when your parents find…”

“Alice, you really think I’m going to tell my folks? Why in the hell would I do that? I’m not going to do anything, I promise. There’s no reason, none at all. Just…what just happened? I mean, did I do something that…”

Alice looked down for a few seconds before looking back into my eyes. The tears were gone, but that apologetic expression remained.

“It’s been so long since I…not since before I got divorced. At least four years since any man…my god. I can’t believe what I just did. But it’s been so damned long. Your door wasn’t closed all the way, and…I just…”

“Just what?”

“I stopped and saw you taking your clothes off. I couldn’t look away. I just couldn’t. I haven’t seen a man…like that…in years. I couldn’t look away, you understand? I mean, you were right there, and…goddamn. I just stripped off my clothes and…I wanted it. You see? I needed it right then and there, and…”

I remained clueless as to what she meant, but I didn’t want any lingering confusion. Things were awkward enough as it was.

“Alice? You needed…you needed what?”

“You know what I mean, don’t you? I mean, I know it’s crazy, expecting, or hoping, or whatever, I mean…you’re eighteen and I’m past forty. It’s ridiculous, I know. But I thought…I mean, by the time I realized what I was doing…”

“Alice, I really need you to talk to me in plain English. What were you trying to do?” Still, I hadn’t pieced it all together in my mind.

“I…for god’s sake, John. I wanted you. I wanted you to make love to me. It’s been so long since I’ve had a man on top of me…inside me…and…”

“Alice, are you saying…”

“Oh god. I’m so embarrassed. I’m so ashamed of myself…”

“Alice…” At that moment, it came together in my head. I realized what she wanted, and I was surprised then, and still am today, how long it took to figure it all out. It seemed impossible to believe, but there it was. She wanted me to have sex with her. She really wanted it. My mind went fuzzy for a few seconds after this realization, but I forced my world back into focus. I knew I wanted it, too. I saw her mostly naked, and she had a marvelous body. I wanted her, and I didn’t want to steer things away from that. If she wanted to have sex with me, I wanted her to give in to it. I knew, or I hoped, that this was my chance, a chance to finally become a man, and not in the usual fashion of young men of that age. I had a chance for my first time to be with an older woman. That’s the dream of plenty of teenage boys eager for their first sexual experience, but here it was, possibly about to happen. I remember wondering, for at least a second or two, if it was all a taunting dream.

“I wanted you, John. My god, I wanted to make love to you. I need it. My body needs sex. I need sex so badly, and I saw you with no clothes on, and I…”

“Did you really want to have sex with me? I mean, did you really want it? Please Alice, please tell me.”

“John, I…I did. I really did. But…I’m so ashamed of myself…I know that a young man, a man your age…”

“I don’t want you to be ashamed. I want…” I didn’t bother finishing my sentence. I doubt that I knew what my next few words would be anyway. I leaned forward and kissed her gently on the cheek. I didn’t know what else to do.

I was surprised when she kissed me back, this time on my mouth. “Do you…do you want me? Do you…”

“Yes.” That was all I could say.

“When I stood up, you saw me? Do I have…do you think I have a nice body?”

“Yes. My god, yes. You have a beautiful body.” I spoke with utter sincerity.

“You…you want to make love to me? Do you really want me? Do you want my body? I mean, do you really want to make love to a woman my age?”

“I do want you, Alice. You look incredible. I mean, you’re a sexy woman. But…”

“But what?” Her expression was no longer apologetic, but rather curious, as though she was interested in where this was going.

“I’ve never done this before,” I said, without a trace of shame. “I’ve never been with a woman before. I’m still…”

“A virgin?”


Alice leaned forward again and kissed me on the mouth, and I kissed her back. Gently at first, but within a few seconds, her tongue entered my mouth. I had never experienced a kiss like that before, and I felt myself stiffening again. I got so hard that it was beginning to force my towel open.

Alice pulled her tongue from my mouth but kept her face pressed against mine. “My god, John. I want it. I want you to make love to me. I want your mouth on me. I want you to kiss every inch of my body. I want to feel you thrusting inside me. I need it so badly. I want to be your first. I want to show you what it’s like to have a woman. Let me show you.”