Teenagers In Lust

I wasn’t ready to have sex when I started dating my babysitter. Though he was nineteen years old, with many notches on his belt, I was only fifteen, with not so much as a pinprick through mine. And the last time we were anywhere near a bed together, I was eleven and he was tucking me in. My family wasn’t too keen on my dating him; yet nobody tried to dissuade me.

  I didn’t like him very much, but because he was the first boy to acknowledge me, it was a novelty. I was all too aware that my gut was trying to warn me, saying things like, “Uh...I wouldn’t do that if I were you” and “What the fuck’s wrong with your brain?” But I was going through an ugly phase with my hockey hair, Javex-dyed jeans, and Harley Davidson sweatshirt; I was quite positive there wouldn’t be any other takers. The same could’ve been said about him. He wore hand-me-down Cosby sweaters that were two sizes too small, sported a long, curly mullet, and still lived with his mother in her trailer.

  Consequently, both of us were embarrassed to be seen with each other. He was embarrassed because I was a fifteen-year-old girl who looked more like a ten-year-old and he didn’t want to be mistaken for a pedophile. I was embarrassed because deep down I knew I wasn’t a redneck, even though I looked the part. I wasn’t exactly sure what I was. All I knew was that I was the only girl in the school who dyed her jeans white by soaking them in buckets of pure bleach.

  At first, our dates didn’t consist of much. He’d invite me to the trailer to watch TV with his mom. Every time she left the living room to refill her glass of moonshine, he’d stuff his hand between my legs and start rubbing me vigorously. It was awkward and inappropriate. It lacked class; yet it was exactly what I expected. Living in a town of sixteen hundred people, of which 80 percent are redneck, I knew what I was getting myself into.

  Despite my dislike, I eventually let him steer me away from his mother to make out in his bedroom. It was my first time doing anything with a boy and it turned out to be quite repugnant. I would emerge from our sessions with my mouth slathered in saliva; the edges already dry and crusty with his spit. I sometimes had to pretend he was someone else, like Michael J. Fox or the son from Mr. Belvedere –-  someone attractive who didn’t look like he’d know what to do with his tongue. It only worked for a short time, though. I knew I couldn’t continue doing this, and I certainly knew I couldn’t go any further. 

One post-spittle-exchanging evening, he threw a box of condoms on the bed. Panic shot through me.

  “I’m still a virgin,” I blurted out.

  “That’s okay. I’m not, but whatever,” he said, ripping into the box. I threw my hand over his when he reached for a packet.

  “Well, I just don’t think I’m ready yet.”

  “Really? But we’ve been dating for two weeks.”

  “I know.”

  “When d’ya think you’ll be ready?”

  “I have no idea.”

  “Well, what about tomorrow? Do you think you’ll be ready then?”

  “I doubt it.”

  Within five minutes, I found myself in the passenger seat of his pick-up truck. Besides the Kim Mitchell playing softly in the background, it was completely silent. He didn’t even look at me. I couldn’t decide whether I wanted to crawl under a rock or punch him in the face. Not that either would’ve made a difference, or a dent, in his life.

  An hour later, he called me. No surprise there.

  “Look, I can’t go out with you anymore,” he said.

  “That’s okay.”

  “It’s just that, well, I’ve been too busy working on my truck and I don’t think I’m going to have any free time in the next while.”

  “That’s okay.”

  “I mean, it’s not that I don’t like you...it’s just...you know...my truck...”

  “I understand.”

  “Oh. Okay. Well...see ya around then.”

  “See you.”

  Even though I was relieved, I couldn’t help but consider the possibility that my life was over, that I was doomed to walk this earth alone.  But I knew deep down that it’s better to be alone than to be with a redneck that didn’t even have his own trailer.  

Just as I predicted, there was nobody after that. Not that year, anyway. And not in that town. But the next year, when my mother, brother, and I moved to a slightly bigger town (with forty thousand people, only 60 percent redneck), I happened upon a whole new breed of humans. They looked exotic with their skull toques, flannel jackets, and Nine Inch Nails cassettes. Skateboarders were a far cry from rednecks; in fact, they were downright classy in comparison. For starters, their long hair was all one length, they listened to songs about anarchy rather than songs about patio lanterns, and not one of them lived in a trailer. It was time for me to get classy too.

  I cut off all my hair and traded in my rocker civvies for over-sized, thrift-store clothes. I started doing rebellious things like drinking malt liquor outside the 7-Eleven past midnight, sticking my fingers down my throat before bed and after breakfast,  and writing “clit” in pen on my desk in math class instead of learning algebra. I was cool, skinny and sexually adventurous. There was no shaking me. I was ready for second base. Well, relatively ready. As long as there weren’t any penises involved.

  For the first couple of months, I let the boys I dated touch my breasts. I couldn’t believe my luck. I was so happy that they actually wanted to. First there was Rick. He was overly cautious around me; respectful and kind and all that other stuff that appealed to me in the beginning but became a turnoff in the end. He actually asked my permission to cop a feel, which I granted and then regretted. He was so tentative about it that I had to look down to know for sure that he was actually touching me.

  The next day, he sent a half-dozen roses to my house with a note that said “Thank you.” To be with someone that thankful for such a small thing kind of freaked me out. I wondered what I’d get if we actually had sex. A half dozens wreaths with a note that said, “Marry me”?

  I broke it off with him and moved on. Next came Trevor, then Seth, then Scott. They weren’t as courteous as Rick, or as thankful, which was great, but they ceased to blow my mind. They didn’t give me reason enough to go back for more.

  And then came Todd. I can’t recall exactly what made him so special, except that he was in French immersion, touched me with such accuracy that it definitely made me want to go back for more, and was so cocky that he knew exactly how to play me. He’d switch from pretending I didn’t exist to grabbing my ass in the hallway. He always had the upper hand, and as a result, he was the only one whose penis I felt compelled to see. The first time was in the boiler room at school, which was our usual stomping ground. He unzipped his pants for me and whipped it out. It was hard and smooth and something that my hand was meant to be wrapped around. He soon became accustomed to his daily lunch-hour hand job. It was with him that I discovered something quite unsettling. Something that made me horribly nauseous. When your hand comes in contact with a penis on a regular basis, it’s easy to fall in love. Needless to say, the hand jobs increased in both quantity and quality. We were the makings of a happy couple. Well, he was happy, and we weren’t exactly a couple. Which was why he was happy. He got the hand jobs without the commitment. All I got was a cool muscle between my pointer finger and thumb, and a stalker-ish obsession.

  “But, why, Todd ? Why won’t you go steady with me?” I’d ask, putting my hand down his gotch.

  “Because I just don’t think we’d make a good couple,” he’d answer, letting me.

  “But, why?” I’d ask, beginning to wank him.

  “Because I like....the way....things are....you know?”

  “Are you sure?”

  “Oiu...oiu!” he’d yelp, accidentally getting spooge on my pants.

  “How, oh how, am I going to get him to be my boyfriend?” I’d wonder to myself as I wiped the cum off with the sleeve of my shirt. “And how am I going to explain this crusty white spot to my mother? It doesn’t exactly look like toothpaste.”

  Finally, to my astonishment, the begging paid off. He agreed, but it didn’t last long. Five days to be precise. He wanted to go back to the way things were. I wanted to give up on men entirely and become a lesbian. So, for the rest of that year, that is precisely what I did.

  I started wearing polyester granny dresses and coming onto the girls I passed in the hallway. We did everything within the realm of the mouth, from tentative pecks to full-on tongue action. The latter I experienced with Kylie. She tasted different from the guys. More pure or something. Maybe it’s because she was the only one I’ve been with who used a toothbrush on a regular basis. Whatever the case, it was nothing short of mind- blowing.

  One day, sitting together in the library, we started passing notes to each other.

  Kylie: I think I might be bisexual.

  Me: Me too.

  Kylie: I want to do more than just kiss.

  Me: Me too.

  For the second time that year, I fell in love. We would hide behind a stack of books in the back of the library and do things I wasn’t sure were considered sex. I mean, it’s not like she broke my hymen or anything. But it didn’t matter because she was beautiful and soft and I would like to have said she was all mine but she wasn’t. She had a boyfriend who she spent half her time with, a boyfriend who made things difficult when we decided to take our relationship one step further.

  Kylie: I think we should do oral.

  Me: Okay.

  Kylie: I have the place to myself this weekend. Want to come over?

  Me: Okay.

  This was definitely new territory. I’ve never put my mouth on anything quite that fleshy before. Not even a penis.

  At the beginning of the evening, she sang a song she wrote for me on her guitar and then tried to teach it to me. It was the most romantic experience of my teenage life. After I learnt the first few chords, I went down on her. It was weird. First of all, I wasn’t too keen on what my mouth was doing, and second of all, her boyfriend was watching us from the living room window. Next thing we knew, he was in the living room with us, naked. I didn’t want to be a part of their dynamic (after all, I was still a virgin and wasn’t emotionally or physically equipped to take on two people at once), so I sat in the corner and waited for her to give him a quick blow job before kicking him out. After he left, she closed the blinds and then finally went down on me. That was a better experience, but I knew it couldn’t last. After seeing Jacob’s penis, I still had a hankering for boys. And Kylie definitely still had a hankering for Jacob.

  Kylie: I love Jacob, but I love you too. I don’t know what to do.

  Me: Can’t you do both?

  Kylie: Jacob wants me to choose. 

  By the end of the Summer, she chose Jacob and I became straight again. To celebrate my born-again heterosexuality, I got rid of my feminist hippie clothes and decided to start having sex. No mashing mittens this time; I was talking full-on penis-in-vagina penetration.

  I wanted my first time to be with Todd, but since he was away for the summer, I decided to go for what I thought would be an easy target. Someone whom I assumed was also still a virgin, someone who just seemed too nice a guy to not be. Instead of approaching Rick directly, I made my intentions known to his friends.

  After word got around, I literally had to chase him down. He was being so impossible, avoiding me at every turn. Was he no longer interested in me? Was he just nervous? Was he dating someone else?

  He was dating someone else. But I didn’t let that discourage me. After all, the word was already out, all I had to do was convince him that I was the one he should lose his virginity to.

  I figured his friend’s house party would be the perfect setting. I knew his girlfriend wasn’t going to be there and that the pressure from his friends would help set my plan in motion. Once we were there, though, it was almost impossible to get him alone. We played cat and mouse for a good part of the evening until finally I was able to corner him. “I want you to be my first,” I said.

  “Why? I thought you didn’t even like me.”

  “What d’you mean? I like you.”

  “Then why’d you break up with me?”

  “I don’t know. Because I’m stupid.”

  “Well, I’m seeing someone.”

  “Well, just don’t tell her then.”

  After a couple of minutes of shameful haranguing on my part, he took me into one of the empty bedrooms. By the time he closed the door and turned on the lights, I was a quivering mess. And by the time he took off his clothes and I saw his penis, I was epileptic. I mean, my God, it was the size of my forearm! And the head alone was as round as my wrist. It was at least two times bigger than Todd’s. There was no way that thing was going to make it all the way in me. No way in hell. I stood there gaping, scared stiff until I reminded myself that a woman’s vagina is very pliable. I mean, they had to be. How else were babies able to get out?  As long as he was slow and gentle, it was possible for it to make it through. I needed to calm down and prepare myself for this thing that looked like a tree branch. I could use the same tactic I used on my babysitter. I could pretend he was someone else. As he stood naked before me, all six feet of him, with his wild hair and his gigantic, tree-branch-shaped penis (which I suddenly wanted to swing from), I couldn’t help but think of Tarzan.  I quickly took off my clothes and sprawled out on the floor. He lied down next to me and then rolled the condom on; he did this with such ease and precision that I wondered if he wasn’t a virgin after all.  Maybe he had already done it with his girlfriend. Maybe even twice.  Maybe with more than just her. Maybe I’d end up being so good that I’d surpass them all.

  I raised my legs high into the air to indicate my readiness. He responded by climbing on top of me and promptly sticking it in.  First came the head, which to me was big enough on its own to cause irrevocable damage. Was it possible for my hole to become so stretched out that it would stay that way forever? But surely after women give birth, their vaginas return to normal size. I reminded myself to breath and then spread my legs as wide as they would go.

  Next came the shaft, which he pressed into me little by little until half of it was engulfed in my now-gaping minge. He stayed like that until I gave him the go ahead. He pressed in farther still until not a trace of his penis could been seen. I was a little in pain, but triumphant. I took it! I took it all!  My head broke out into the Barry Manilow song “Looks Like We Made It.” Then something popped, but it wasn’t my cherry. It was the condom; it seemed his cock had torn right through it. I asked if he had another, but he didn’t; he had to borrow this one from his friend. I asked if he could borrow another one from his friend, but he said no and I assumed it was because he was too embarrassed. So, instead of doing it again, he laid me against his chest and promised to call me the next day.

  That call never came, but I didn’t really care because I was woman now, even though my hymen was still intact.

  I became even more rebellious, purchasing whore-ish clothes from Le Chateau, masturbating with ferociousness, and developing a superiority complex.  I even went as far as getting a job as a dishwasher and moving out, because real women don’t live with their mothers.

  The first day of the last year of high school, I blazed in wearing my Spandex hot pants and platform shoes. I wasn’t fucking around this time. I meant business.

  Todd saw me approaching from all the way across the schoolyard. Hell, everybody saw me. I was the scantily attired girl plodding clumsily through the grass toward Todd, looking like a child prostitute desperate for her day’s pay.

  “Nice outfit,” he said, either sincerely or sarcastically. I couldn’t tell.

  “It’s French,” I said and then I asked him point-blank, “Do you want to have sex with me?” He said yes and we picked a weekend his parents were going to be away. It was that easy.

  It was my first time at his place. I wanted to take full advantage of our alone time in this spacious, moderately decorated lair. As he took me for a tour, I imagined doing it on the kitchen island, in the La-Z-Boy, in the tub, on top of the dryer, on top of the mini-fridge, on top of the pool table, in the wine cellar, and in his parents’ closet.

  The last stop was uninspiring. His bedroom. With his tiny single bed and Spider-man pillow that was almost as big as the bed, I wanted to change my mind and do it at my place instead where I rented a room in a house with a married couple and a schizophrenic. I had a queen-sized bed and naked pictures of Madonna all over my walls. My place was sexier aesthetically speaking, but the seventy-year-old mental case that lived across the hall and complained about killer squirrels was not sexy. I knew I had to make do and I was too nervous at that point to suggest doing it on the porch swing instead.

  “Après vous,” he said, pointing to the bed. Fuck, I loved it when he spoke French. I threw the pillow down and yanked back the sheets. When I climbed into his bed, I swear I felt dirt. I tried to discreetly wipe the bedsheet clean while he took off his pants.  He jumped in beside me and asked, “Is this your first time too?” My, my, the boy was still a virgin and I was not. Who had the upper hand now?

  “Yup. Looks like we’ll be losing our virginity together.”

  “Cool,” he said, pulling out his penis and plopping it in my hand. It was a hell of a lot smaller than I remembered. Rick had completely distorted my perspective on size. This was going to be a breeze.

  Foreplay lasted about five minutes, which was more than I could say about Rick. But in terms of getting the condom on, he was clumsy at best and it lasted longer than the foreplay.

  When he was finally ready for action, I positioned myself in the only way I knew how: on my back with my legs thrown up in the air. He hovered over me, confused for a minute or two, before finally hooking my legs over his shoulders. And then he entered me–supposedly. I lied there, hardly feeling anything at all. If he was actually inside me, as he claimed to be, I didn’t know it. I worried that my worst fear had just been realized: that I was stretched out beyond repair. I wondered, “If I hadn’t had sex with Rick, would I be able to feel this right now?” I didn’t bother to pretend he was someone else. There was nothing really to go on.  He managed to pump me three, four times before coming. I was relieved it was over so fast. I wouldn’t have been able to keep up the charade that I was actually enjoying myself. And even that didn’t consist of much. I just kept my eyes closed and moaned every now and then. It must’ve been enough because when he rolled off me, panting and red-faced, he asked me a question that completely threw me. “Did you orgasm?”

  “Yeah,” I said. “We should do it again sometime.” My unconvincing words hung in the air, waiting to be condemned. But Todd just lay there, breathing heavily while staring off into space. Either he didn’t hear me or he didn’t care or he didn’t know how to respond to a pathological liar.

  As soon as he rolled off me, I started to dress myself.

  “You’re leaving?” he asked.

  “Yeah.”

  “Really? I thought you said you wanted to do it again.”

  “I didn’t mean today. I just meant, you know, in general.”

  “Oh.”                                                          

  I bolted out of there faster than he came. When I got home, there was a dribble of blood in my underwear. Now I really was a woman. And all it took was the erratic thrusts of Todd's tiny penis. (Not, oddly enough, the all-encompassing, slow plow of Rick's tree branch. Perhaps my hymen simply needed a warm-up). 

I managed to avoid Todd for the rest of the year. After graduation, I moved to an actual city. With the population of 629,500 and an equal percentage of rednecks, skaters, lesbians, and French guys, I managed to avoid them all. For the next two years, I experimented with goths, hippies, punk rockers, and bisexual men, all of which turned out to be just as disappointing. But I trudged on like a trooper until I turned twenty and did it with a jock. A little late in the game admittedly but they were a breed I never even considered (and a breed that never considered me). I must say, there’s something to be said about the dumb, pretty ones. They’re good in bed. 
 

Tammy Kenward is a freelance sex writer residing in Toronto, ON. Her essays have been published in NOW Magazine and currently appear in Clean Sheets, Inscribed.org and The Erotic Woman.

Check out Tammy's own site by visiting http://www.tammykenward.com. And don't miss her hot new sex column at http://www.shedoesthecity.com

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