Supposedly, prom night is the night most people lose their virginity. If this is true then I don’t know most people. The average age of being deflowered in my high school was 15----16 at the very latest. I didn’t know anyone who was 17 and still a virgin. I myself was a late bloomer, being one of those who didn’t lose it until my sixteenth birthday. So, for me and the others like me, the only allure prom night held was that it was simply the one night we could go out and party and not be expected back. This left the evening with only one attraction for me: lots and lots of time. For the first time ever, Nicole and I were going to have sex at a leisurely pace; no worrying about how much time we had until we had to get back or when either of our parents would be returning. We would just do it until we were done. Still at the age where I could do such things, I planned to luxuriously fuck her at least three times, climaxing in an exploration of the forbidden zone: anal sex. Nicole had previously been unwilling, but I felt that was only because I didn’t have enough time to convince her and I wasn’t about to waste our valuable sex time on begging and pleading. That wouldn’t be a problem on prom night. I would be able to wear her down at my leisure. Initially, things progressed like clockwork. My dad, thinking that this was going to be the first time I ever had sex, was more than happy to lend me his BMW, but not without obvious hints about buying condoms. I, in turn, hinted that I already had done so, but I was lying. Nicole used sponges so I never used a condom. We were still young and stupid enough to believe that diseases were for other people. I later found out that half the senior class had herpes. The only thing that saved me was a habit of consistent, long-term relationships. Like my junior prom, we were obliged to start the evening with photos and films for both sets of parents, not to mention formal photos for a professional photographer. The latter appointment was actually the first social event of the evening, as everyone who was anyone went to the same photographer. While waiting for our turn, the boys and girls separated to discuss our plans for that night’s real event: after the prom. As usual, Melanie’s mom was throwing a party, but that was for the losers. The cool kids were headed either for other, unchaparoned parties or for various hotels and motels all over the city. Josh even had his parent’s place by the lake, the bastard. It was during this exchange of information that I got my first hint of the trouble to come. Apparently, Nicole and I were in adjoining suites with Glenn and Trisha at the Marriott. Nicole was best friends with Glenn’s girlfriend Trisha. This had forced Glenn and I into a closer friendship than either of us wanted from the other. I didn’t dislike Glenn, but I didn’t want him to hear me fuck, nor did I want to hear him fuck, but apparently the girls wanted to have breakfast together and they though this would be a good idea. My second clue was that Glenn was already drinking. Early on I’d learned that sex and drinking didn’t mix. I got drunk with the fellas, not the girls. In fact, the goal was to get them drunk so they would agree to have sex. Glenn didn’t share my outlook. More than once had he gotten too drunk and saddled Nicole and I with Trisha, usually ruining whatever plans I had for intimacy that evening. I was not looking forward to this on my prom night. After our pictures were done it was time for the prom, which was being held in the ballroom of the Hilton where some people had been dumb enough to get rooms. To me, that was asking for trouble. It was a little too close to our teachers for me to be comfortable. Leaving early for "dinner" could prove to be embarrassing when you bumped into the track coach on the way to your room. For me, it was all a waiting game. After all, I didn’t see anyone there that I didn’t see every other fucking day, so why was that night any different? In fact, it was worse. How were we supposed to party effectively under the watchful eye of the faculty? My only source of entertainment was to progressively get Nicole intoxicated with the vodka I had on me. My idea of sexual preparedness was to buy lubricant and a flask. By the time the "official" end to the evening came, Nicole was good and buzzed, but unfortunately, Glenn was completely fucking drunk. This meant I would have to drive us all to the Marriott. This quickly pissed me off, because I knew the girls would want to socialize more when we got there, thus cutting into my literal fucking time. Even worse, they’d be drinking more. Granted, I wanted Nicole drunk enough to let me butt-fuck her, but I didn’t want her passed out drunk. I’d fucked her a few times that way and it sucked. To try and prevent that contingency, I began passionately making out with Nicole while waiting for Glenn and Trisha by the car. As close as they were, Nicole was still capable of blowing Trisha off to get laid if she was hot enough. I needn’t have bothered. Glenn and Trisha spent the ride over making out in the back seat. This actually seemed to arouse Nicole, and for the first time I thought maybe their being so close might be a good thing. When Nicole reached over and began playing with my dick while watching the backseat activity, I developed a sudden appreciation for the company of close friends. Our friend Kyle, who worked there on the weekends, had previously arranged our hotel rooms. Two hundred slipped to the desk clerk for an unused room had more than taken care of everything. Later, I realized we couldn’t have been the only people who had this deal. Their take for the evening must have cleared a grand or two, easy. We slipped in the side entrance and headed up to our rooms, the others giggling like a bunch of fucking kids in giddy anticipation. I had no reason to laugh, as what I feared most about Nicole and Trisha came to pass: as soon as we hit our rooms they opened the connecting doors and continued our unwanted (by me at least) foursome further. Champagne had been arranged and was already waiting. The girls popped the cork, turned on the radio and began their little party, which seemed to be based on trashing their female classmates’ prom attire and dates. I’m sure sex was somewhere on their minds, but it wasn’t first on their minds. Glenn, ever the student of an altered conscious state, was no help. He would always rather party than fuck, and had abandoned whatever passion he’d displayed previously to fire up a joint. The girls eagerly shared it and I was then forced to join in so Nicole wouldn’t get mad at me for bringing everybody down. No matter how I fought it, the effects of shallow toking and slow sipping of champagne came, and time slowed down to a crawl. It seemed like hours before my chance to end that little bacchanal arrived, but arrive it did in biology taking its course: after a full night of drinking, Nicole had to go to the bathroom. When I dashed in after her, she merely giggled drunkenly at me then sat down on the toilet. She laughed outright when, in an all-or-nothing move, I pulled out my hard dick and stuck it in her face. Nicole looked at it for a few moments before her eyes, formerly heavy-lidded with booze and pot, now became heavy-lidded with booze, pot and lust. She looked up at me and smiled before engulfing more than half my length without even using her hands. Nicole began to suck on me softly, using the flat of her tongue to stimulate the sensitive underside tip, and for the first time that night, I really began to enjoy myself. It was short lived. By the time Nicole started to push me into the back of her throat, with one hand now on my balls and the other on my ass, Trisha began to miss her and started knocking on the door. With a reluctant moan, Nicole released me. She then kissed the head, wiped herself and was about to leave, when I sank to my knees and grabbed her waist. I pushed her dress back up and began to literally kiss her ass, pulling aside her white lace thong to taste the bitter rosebud of her anus. She gasped, shuddered and halted in her tracks. When she began to push back to me, I know our little party with Glenn and Trisha had come to an end. Trisha continued to bang on the door, but once I reached Nicole’s pussy, her soft sighs became very audible moans. The knocking then stopped and the next outside sound I heard was that of the connecting door slamming shut. Finally, it was time for our night to really begin. I quickly stood and grabbed Nicole quickly for a passionate kiss, causing her to taste herself, something she’d object to if given a chance, but I felt she secretly got off on it. Little did I realize how much. I would later discover she not only liked her own flavor, but became curious about others as well. A curiosity that would be encouraged. We moved from the bathroom to the bed kissing, struggling to simultaneously undress without breaking contact. As much as I disliked the actual physical effects of drugs and alcohol on sex, the mental effects were always a plus. What little inhibitions Nicole possessed would vanish with her sobriety. The girl who once refused even admit she masturbated, would soon be finger fucking herself in front of me and making me lick her fingers clean. That night was no exception. Nicole had the foresight not to wear anything other than her panties under her dress, so she was naked first. Our embrace was broken for as long as it took me to get off the rest of my things. While watching me struggle with my clothes and my excitement, she began to touch herself. Though I hate to admit it, the fact that her hair was still up in that prom-doo made it all the more exciting. Once naked, I crawled onto the bed slowly, doing the "jungle-cat-sexuality" thing that Nicole loved. Like a cat, I began to lick her slowly while looking into her eyes. Nicole maintained eye contact for as long as she could before she closed them, surrendering to the to pleasure. Sex with Nicole wound up spoiling me, as we were so in tune sexually. We knew all the right buttons to push on one another. The first woman I had sex with in college was not very impressed with the "jungle cat" or me. That night, however, I was still on top of the world, and Nicole was grabbing the back of my head as her first orgasm rolled over her. Though never a quiet lover, Nicole was especially vocal that night. If I had been a bit more astute, I would have realized she was merely showing off for Trisha. It’s what that night was all about. At the time, however, all I knew was that it was getting me incredibly hot. I couldn’t wait to get inside her. I rolled Nicole onto her stomach and pulled her down to me, where I entered forcefully from behind. Ironically, when she became truly overwhelmed by pleasure, her volume decreased, leaving the most audible sound in the room that of our colliding bodies. Due to my over-excited state, I was totally lost in the sex and was unaware of Trisha’s entrance. I only noticed her when Nicole noticed her, and when Nicole noticed her she came so hard her constricting vaginal muscles pulled my orgasm from me prematurely, the sudden bolt of pleasure momentarily forcing my eyes open. That’s when I saw Trisha sitting there, watching us. We collapsed on the bed into a gasping, spasming heap to Trisha’s quiet applause. Nicole giggled but I, however, was not amused. I’d had a great fuck ruined by a premature orgasm. It’s like being forced to gulp down a fine wine. You still get intoxicated but without the pleasure of the drinking. Trisha must have seen the evil in my eyes, as she apologized with more sincerity than I was used to from her. It seems that Glenn had passed out in the middle of a blowjob sending her over sooner than they’d planned. They’d planned? The slightly panicked look on Nicole’s face told me this was one detail I wasn’t supposed to hear. I pulled out of her and sat back on the bed, too annoyed to bother covering my wet, half-erect dick. Trisha didn’t even pretend not to look at it. "Take a picture," I said, "It’ll last longer." "Don’t think I wouldn’t," she retorted. "Well, Nikki?" I said with a sigh. Nicole recovered quickly and didn’t bother answering until she had gotten herself another glass of champagne. Trisha didn’t pretend not to look at her either. "Well, lover," Nicole began as she lay back down beside me, "I wanted to make this night something special, you know? I mean, how many times to we get a chance to fuck all night without worry about time? Didn’t you want to take advantage of it?" "You have no idea," I said, trying to fight the smile that was spreading across my face. "Please," Nicole snorted, "A little something more than just fucking me in the ass." They both laughed at this, damping my ardor somewhat. Nicole had obviously been sharing the details of our sex life with Trisha. "That wasn’t the only thing," I protested weakly, hoping they wouldn’t ask me just what else. "Aw, I’m sorry baby," Nicole said, cuddling up next to me, trying to soothe my tender, teenage, male ego. "I know you did. It’s just that I felt, maybe, we’d have more options if we had more....people." At this, they looked at each other and smiled. I felt an odd chill that I couldn’t decipher. Was it anticipation or fear? "Well?" Trisha asked. "What about Glenn?" I replied, not knowing why. Seeing Glenn naked was high on my list of things never to do in this lifetime. "What about him?" Trisha said, standing. "I really didn’t count on him for this. Even if he had managed to fuck me, he’s usually only good for one and we need more than that." At that, Trisha began to undress. Unlike Nicole, Trisha hadn’t even bothered to wear underwear, so in matter of moments she joined us naked on the bed. Trisha lay down on her stomach and cradled her head on her interlocked hands like a libidinous Audrey Hepburn. She smiled sweetly at the two of us and said, "Well?" Like any normal heterosexual male, I had fantasized about having sex with two women at the same time, and at that moment I realized the one component that had been missing from all my fantasies: a beginning. Just how does one begin a three-way anyway? At this point the odd chill returned but this time I knew exactly what it was: fear. I felt a wave of butterflies rush through my stomach and Nicole, whose head was resting there, must have felt them because she turned and began kissing my abdomen. "Oooh, someone’s excited," she said, handing me the glass of champagne. "Not from this angle," Trisha said, looking at my crotch with an exaggerated squint. "Some of us have already had sex," I countered, actually nervous about the fact that I wasn’t hard again even though Nicole was now sucking on my nipples. "So what? According to Nikki, you can get it up on demand. Well, I demand that you get it up for me." At that moment I realized why I had always disliked Trisha somewhat: she was my competition. Since Day One we had been engaged in the eternal struggle: The Best Friend vs. The Boyfriend. The Best Friend initially holds the upper hand because, well, they’re The Best Friend. They were there before you and would be there after you were gone. However, The Boyfriend through sex can establish a narrow lead. It’s the one thing in which The Best Friend can’t share. Now I was on the verge of losing that one advantage. Trisha and I both knew it and one of us was very happy about it. Realizing the best thing for me would be to put Trisha out of my mind, I put down the drink and turned my total attention to Nicole, who was now up to my neck. I pulled her onto me and began kissing her deeply, sucking on her tongue and then allowing her to suck on mine. My tensions were somewhat eased when I felt my dick finally began to stir, struggling to extend between our two bodies. Realizing space could only do me good, Nicole rose up with her knees on either side of my body, her ass high in the air. It was then that I found out how a three-way began. Nicole was kissing me when suddenly she moaned and dug her nails into my shoulders. I had been gently squeezing her nipples but that had never provoked a response this intense. It was only when she broke our kiss to rest her head on my shoulder that I was able to look down and see the source of her pleasure. Rising just above the crest of Nicole’s ass was the top of Trisha’s head. She was eating Nicole’s pussy. My dick expanded to its full length so quickly it actually hurt. "Now, that’s much better," Trisha said taking my dick into her hand and beginning to pump it. At that moment my first three-way also became my first instance of self-loathing. Someone I would otherwise despise sexually aroused me. I felt an odd surge of anger, which in turn fed my desire. My dick never felt harder than it did at that moment. Trisha only made matters worse by beginning to blow me and being good at it. It wasn’t all she was good at either. Nicole began to rock back and forth, moaning. As Trisha wasn’t eating her anymore, this meant she must have been fingering her. She was blowing me and finger-fucking Nicole at the same time and in rhythm. She was good. Too good. I began to hate her even more, which of course made me even harder. "Somebody’s ready to fuck," Trisha said, releasing my dick with a loud slurp. "I wonder who it is." Nicole didn’t reply. She was too busy trying to feverishly mount me. I don’t think she was on the same plane of existence as us anymore. Like me, she was more aroused than she had ever been in her life, though for different reasons. She came as soon as she got me inside her, but it wasn’t enough and she began to ride me furiously, now genuinely loud with a passion I’d never seen before. This display delighted Trisha, who forcefully pulled Nicole’s head back so she could kiss her deeply. This was all Nicole needed and she suddenly ground hard on me, indicating yet another orgasm. Trisha then did the one thing I hoped she would/wouldn’t do: she leaned forward and kissed me with the pungent taste of both Nicole and me on her lips. Our kiss was more a duel than anything else. We stabbed with our tongues and bit each other’s lips until we drew blood. Trisha broke our kiss with a triumphant laugh. I didn’t know it then but she was entitled. She had won. After that night, the shadow of the passion she brought would always be there with us. Nicole and I wouldn’t be able to touch one another again without thinking of how much better it would be with Trisha there with us. And Trisha knew it. The rest of the night was a blur of naked flesh, with every possible sexual permutation explored---including anal sex, which was a bit of a let down for me, though pleasurable. Nicole, however, seemed to enjoy it, but Nicole enjoyed everything that night. She never came down. Nicole furiously fucked us both until she collapsed from exhaustion----with me still inside her and her face in Trisha’s crotch It was an awkward moment; me still inside the sleeping Nicole and her head resting between Trisha’s legs. Not knowing what to do next, Trisha and I managed to look at every other object in the room before coming to each other. Simultaneously we both made Nicole the focus of our attentions. We carefully laid her under the covers, though I doubt even a shotgun blast could have woken her. Once that was done we were again left without a purpose and once again we made the same decision: shower. We moved off the bed and in the same direction at the same time, our bodies gently bumping. We stood there for a second, trapped in the tension like flies in amber. I wondered if she could feel my pulse through my still-hard dick, which was resting, against her stomach. When she wrapped her hand around it, I shuddered with hatred and strange lust. Trisha and I went into a heated embrace and sank to the floor. She guided me into her and wrapped her legs around my back. I grabbed her ass and tried to penetrate her as deeply as I could, over and over and over again. When we both came, it hurt like hell, but for one brief, odd moment, I felt incredibly close to Trisha as we lay there shivering on the floor, our raw genitals still coupled. She felt it too and I feel it unnerved her even more than me. Hate is a powerfully binding emotion. Mixing it with sex only makes it worse. It came as no surprise to me when Nicole told me that Trisha had no interest in doing it again, nor was the knowledge that it was Trisha’s idea from the beginning. After Nicole had told Trisha of the thrill she got from tasting her own juices on my lips, Trisha was quick to suggest maybe she’d like to try another; specifically Trisha’s. Nicole wasn’t too enthused about a singular homosexual experience, but a menage a trois caught her little bourgeois fancy. Still, once the wall came down for Nicole, there was no going back. We maintained our relationship for the rest of the school year and that summer before college, but I knew she and Trisha continued to fool around even though I was no longer invited. Nor was Glenn, for that matter. Trisha dumped him the day after the prom. I had a good idea as to what this said about Trisha, but I kept it to myself. I knew that Nicole would cut all ties with her if she thought for one second that her best friend was a dyke and not just another upper-middle-class girl taking a walk on the wild side. Eventually, however, there was no more denying it. When the time came for us to go our separate collegiate ways, Trisha got the same farewell fuck that I did, but she made the mistake of blurting out that she was in love with Nicole, something that had never even crossed my mind. Nicole reacted the way any girl would who’d been eating pussy all summer but still had a boyfriend: she dropped Trisha like a bad habit. I got the ax as well. After all, I too was responsible for her being with a..... lesbian! I didn’t see either of them again until our ten-year reunion. Nicole, there with her good-looking, but-obviously-dull husband, barely acknowledged me and outright snubbed Trisha. Apparently, she’d rather forget the crimes against god and nature we’d committed together. I expected the same treatment from Trisha, but surprisingly, she was very nice. Maybe it was because I was the only one who didn’t bat an eyelash when introduced to her fiancée, Sharon. As I was dateless, I wound spending most of the evening with the two of them, prompting a slight buzz of attention from our former classmates and a cold, hard continuous stare from Nicole.
