(Author’s note: This is going to be a multi-part story. This first chapter is relatively light on sex, but there will be a lot more action in subsequent installments. Everyone in this story is at least eighteen years old)
(And a quick shout-out to ErikaKane for her editing assistance with this story. Couldn’t have hoped for better.)
I turned eighteen a month into my senior year of high school. Skinny, shy, good at math; I was last pick for the basketball team and last pick for the opposite sex. But by Christmas, I had gone from being terrified of girls to living the cliché as the official “sexually non-threatening platonic guy friend” of the five hottest chicks in school.
As nice as it was to have popular friends and beautiful women to look at all day long, I was also anguishing in a special circle of Hell, where my penis and I were at a constant state of war with each other. The argument went something like this:
MY PENIS: “Fuck her! She’s hot!”
THE REST OF ME: “No, we’re friends, it’d be weird…”
PENIS: “But… tits!”
Needless to say, it was a confusing time for me.
It all started with Corrine — a bodacious blonde who was clearly destined for the Playboy centerfold. For a late-blooming nerd like me, she was also the most intimidating person on the planet. Every detail about her seemed specifically designed to twist my tongue into knots. First off, she was the tallest girl in school. I was 5’11” and she had maybe half an inch on me (Corrine liked to joke that this was due to her “Viking ancestry”). She also had a dazzling smile that belied an impish, teasing spirit, and a natural hourglass figure. But what really made my head spin were her tits. Her absolutely gigantic tits. The day those things had grown in, every guy in school promptly forgot his name. Seriously, her tits could stop traffic.
She and I became friends when I sheepishly asked her to be in an amateur horror movie I was directing with some buddies. Asking had not been an easy task for a guy like me—Corrine had always been a merciless tease. But nonetheless, as soon as the class bell rang, I stumbled over to her desk, feeling mortified but knowing that all the other AV club guys were counting on me to succeed for the sake of our film. I tried to play it cool, but my cheeks went crimson and my voice sounded like it was coming from inside a box:
“Hey Corrine, I’m making this horror movie and we kind of need someone to play the, like, buxom bombshell in distress. I was just wondering if you might think that was fun… or something.”
She raised an eyebrow and grinned wickedly, leaning so far forward it took all my willpower to keep my eyes away from her pendulous breasts. “Sure, Ian,” she said simply, “What do you want me to wear?”
It turned out my nervousness had been completely unfounded. While Corrine was definitely a tease, she was also really easy to get along with. She and I hit it off the first day of filming. We made each other laugh, hit an easy rhythm of conversation, and she even made fun of her own intoxicating hotness—happily donning the increasingly skimpy outfits I asked her to wear. She totally got the movie’s trashy sense of humor, too, and would throw an extra bounce into each step as she fled from a lifeguard-turned-werewolf (Yeah, the movie was crap).
Even after we finished the film, Corrine still called me every day after school, just to chat. We had almost nothing in common besides our sense of humor, but that made our talks all the more interesting. I would keep her on the phone as long as I could, inwardly glowing at the thought of such a gorgeous creature enjoying my company.
Knowing Corrine even got me invited to some real parties for a change. I wasn’t deluding myself that it was love—I certainly wasn’t in “love” with her—but a part of me hoped that against all odds she had started finding the scrawny nerd kid mysteriously attractive. That was all dashed to pieces four weeks into our friendship, when I finally got up the guts to ask her out.
It was at a party Corrine had invited me to. I threw down a couple beers and headed through the dim lights, finally finding my girl in a dark corner, speaking quietly with her equally hot friend, Talia. They didn’t see me in the dark, and I was just about to speak up when I overheard Talia say: “You and Ian seem to be getting pretty tight, would you ever think of going out with him?”
The timing was ridiculous, but what can I say? That’s how it happened. I froze, not wanting to eavesdrop but too close to avoid it. Corrine thought for a second and then answered, “You know, I don’t think so. It’s nice having a guy I can talk to who doesn’t treat me like I’m just a pair of boobs, but he’s not really that attractive. I bet he will be one day, maybe when he’s thirty or whatever. But he’s a GREAT guy.” Soon as she said it, Corrine realized I was standing there and she reflexively apologized. I assured her it was no big deal. We were just friends, anyway. I gave her a quick hug, inwardly groaning at the feel of her tits squashed against my chest, and headed outside to get some air.
Thirty?! I thought, Some consolation prize that is. I’ll be fuckable by the time I’m ready to settle down. I needed another beer. It wasn’t that I was devastated to be rejected by Corrine — hell, I’d been expecting that. It was how her words had confirmed my worst fears: I was doomed to be “just friends” for the rest of my life.
An hour later, I was reclining on the hammock in the front yard, wallowing in self-pity over my bad luck with women, when a body dropped on me and snapped me out of it, a stray elbow clocking me in the face. “Oh, I’m sorry!” Talia laughed, clearly blazed out of her mind, “I totally didn’t see you there!”
I assured her it was no big deal, and she mumbled something incoherent about me being such a “great, great guy” or whatever. We were both too wasted to bother getting out of that hammock, so we just lay there together.
Talia and I barely knew each other. We’d shared a few classes over the years and I had seen her at one or two of Corrine’s parties, but at that moment there were only three things I could recall about her:
1. She was insane. I don’t mean the Ted Bundy/Ed Gein/Glenn Beck BAD kind of insane, I mean the GOOD kind of insane. Like a female Jack Sparrow, I guess? The kind of insane that livens up any party and provides you with a lifetime of anecdotes.
2. She was gorgeous. A raven-haired, smoky-eyed, exotic beauty (half Korean, half Colombian; a winning combination, if you ask me) with full, perky breasts and a fabulous ass she liked to show off with the skimpiest clothing she could find. And —
3. Talia was dating a twenty five-year-old drug dealer named Steve, who weighed about a hundred pounds more than me.
Regardless, I was horny, frustrated, mortified, and confused. And drunk. So I wasn’t exactly thinking straight when Talia started making out with me in the hammock a few minutes later. She was completely faded and her breath stunk of weed. Her kisses were awkward and sloppy, barely making contact with my mouth. It was about the least romantic scenario I could have hoped for, but I gave it my all, desperate to prove Corrine wrong about my ability to attract a mate. My hands roamed her amazing body, daringly squeezing her firm, athletic ass–yes!
Then she passed out. With a disappointed sigh, I rolled away, leaving her to sleep off what was sure to be one hell of a hangover. Talia’s affections had been nothing more than the result of drunken pity, that much I knew. And knowing it made the shame of the evening all the worse. Corrine’s words replayed over and over again in my mind: “Maybe when he’s thirty.” It felt like some gypsy had put a curse on me.
Gloom hung over me the next day at school. Talia bumped into me towards the end of lunch and took me aside, clearly mortified for what had happened between us. She was on the verge of tears as she whispered, “I’m so sorry about last night.”
I put a comforting hand on her shoulder and assured her that I understood completely. “It was just a party thing,” I muttered, “Don’t worry about it.” She nodded and hugged me close, her words spilling out with machine gun speed:
“I’m so sorry I fell asleep—it wasn’t you—I swear—I was just so wasted–I swear I am never ever going to smoke weed again in my life! Can we just—Oh, and thanks for being cool about it and, you know, leaving me alone after I was out.”
She was so earnest, I couldn’t help but smile. “Look, Tal, you know you’re gorgeous, so don’t take offense when I say that the whole non-consent thing just doesn’t do it for me.”
She laughed through her tears, and awkwardly added, “And could you please not tell Steve, if you see him?”
“Right, like I’m gonna tell your huge scary boyfriend I made out with you.” That got me another laugh from her, as well as a playful punch to the shoulder. Then for some reason I just blurted out, “Do you think Corrine was right last night? That I really won’t be attractive until I’m like thirty?”
Talia had enough of a heart to let me down gently: “She was exaggerating, Ian. What she meant was you’ve got the potential to be really cute, but right now you aren’t living up to it. You’ve got a cute face and, like, really amazing eyes, but girls want a guy who takes care of himself. Get a better hair-cut, stop just wearing those baggy comic book t-shirts, and maybe start taking PE a little more seriously. Just a suggestion.”
Unexpectedly, our brief conversation over lunch soon led to me becoming even better friends with Talia than I had been with Corrine. She was always a ton of fun, despite her ADHD, and nowhere near as intimidating. Unlike with Corrine, I never even considered making a move on Talia. Sure, I admired the way she looked in the microscopic clothes she always wore, but we got so comfortable with each other so quickly that thoughts of dating never even came up. Even when she finally broke things off with that loser Steve, we just stayed the course as buddies.
The tighter I got with Talia, the tighter I got with her friends. And what friends they were…
Amy was a naturally beautiful tomboy with strawberry blonde hair and a lithe, lean body. She was far more frank about her sexuality than anyone else I knew, even guys (a bit of what my grandmother would call a “floozy”). The first time Talia introduced me to Amy outside of school, she was wearing a t-shirt with “YES THESE ARE MY TITS” printed across the bust. Amy was the biggest jock I knew, but her real passion was ballet. She poured every bit of herself into her dancing and all that effort had sculpted her body into a thing of beauty. I saw a few of her recitals and she was incredible. There was a graceful, feline sensuality to her movements.
But one thing kept her dreams of dancing professionally in check. Well, two things I guess. Apparently most professional dancers don’t have Amy’s tits. She joked that nobody in the world would hire a C-cup dancer, “Unless it’s on a pole.” I promised her that, if I were to ever own a ballet company, I would ONLY hire dancers with C-cups or bigger.
Then there was Stephanie, who embodied classical Hollywood glamor. Perfect golden ringlets framed a soft, round face and big, piercing blue eyes. She had the kind of zaftig, pinup-type figure that fighter pilots liked to paint on their planes during World War II. Va-va-voom, as the chairman would say. She was feisty and flirty, and a bit neurotic about her hair and makeup. Whenever we all went somewhere she would, without fail, be the last one ready. Our school’s resident “drama club diva,” Steph had played the lead role in every school play since she was a freshman, pissing off the older girls in drama club to no end.
Ever since pre-school, Stephanie had been BFF’s with Elizabeth. Like all great pairs, the two of them were different in almost every way. While Stephanie was only a few inches shorter than I was, Elizabeth barely reached 5’2″. Steph was blonde as they come, but Elizabeth had luxurious dark hair and very fair skin. Steph loved the spotlight, Elizabeth was shy as a mouse.
About the only thing they did have in common was their bra size, 34DD — a running joke that tended to make Elizabeth blush whenever it came up. While the taller Stephanie rocked her curves in groovy proportion to the rest of her frame, on short little Elizabeth those boobs looked positively humongous. As a life-long “breast man,” Elizabeth’s tits made me practically drool, but she was really self-conscious about them, choosing to dress much more conservatively than her friends.
Despite being beautiful enough to merit a statue in the Parthenon, Elizabeth’s quiet, good-girl nature caused her to often be overlooked by guys more interested in outgoing easy types like Talia or Amy. This lack of attention gave Elizabeth the ridiculous notion that she was “the ugly one” in the group, something that drove me insane. Aside from being a regular feature in my sexual fantasies, she was the kindest, sweetest, most thoughtful person I knew and she had no business being insecure.
Before that year, all of us had been in separate cliques, but when we started hanging out together things just worked. We found that rare, perfect group dynamic. If you ignored the gender ratio, we fit every high school cliché: the nerd, the tease, the basket case, the jock, the diva, and the shy kid. Me, Corrine, Talia, Amy, Stephanie, and Elizabeth. But you know what? Our differences made every conversation more interesting. I always say that the longer a person spends with people exactly the same as they are, the dumber they become. It’s like inbreeding your personality.
To my great surprise, I learned that, of my beautiful new friends, only Amy and Talia had any serious sexual experience. Even professional cock-tease Corrine had never gone further than letting a guy feel her up, and Elizabeth had never even done that. My adolescent assumptions about these gorgeous women with their wild, wanton sex lives evaporated when I got to know them all as a group of regular, cool people with the same frustrations and anxieties about sex as every teenager.
Pretty early into our friendship, Amy took it upon herself to get me into shape, and I must say she made the typically miserable task of exercising a lot of fun. Running laps around the park actually became a treat when I was running behind her, watching that impossibly fine ass stretching her tight little shorts. Over time, my body filled out with some nice, lean muscle definition.
I asked all five girls to take me shopping so I could replace my wardrobe. Instead of dropping the money from my summer job on video games, I saved up for some decent clothes. After some female advice and a few trips to the mall, I started to look like a grown man.
As the only male in our group, the babes teased me incessantly. But it was always good-natured and no sane man would complain. Occasionally, however, the line between platonic friendship and sexual curiosity would blur ever so slightly. Somehow, the stars had aligned to make all five girls somehow single during those early months of our friendship, so when I’d be hanging out alone with one of them there seemed no harm in us snuggling up on the sofa to watch a movie, our hands gently roaming each other’s bodies, always careful to avoid direct contact with the naughty bits. It was pleasantly arousing, but never overt enough that things felt weird between me and the girls afterwards.
One time, this innocent snuggling led to me giving Corrine a prolonged massage. I worked my hands up her back until she asked, “Could you undo my bra? It would feel better.”
I swallowed, throat tight. My hands were actually shaking a little bit as I blindly reached beneath her shirt and fumbled with the hooks. My awkward fumbling must have been pretty obvious, because Corrine sat up wearing a Cheshire grin.
“Have you never taken a girl’s bra off before?” she asked. I shrugged, wishing it could be anyone else in the world having this conversation with me. Corrine turned away from me, helpfully lifting up the back of her tank top to reveal the heavy-duty strap beneath her shoulder blades.
“Here, let me show you.” She demonstrated the clasp for me a few times, then said, “Now you try.”
My mouth turned to cotton while I imitated what she had done, unclasping the garment from her back. Suddenly unsupported, her substantial breasts dropped to their natural slope, and my eyes dropped with them. Corrine cast aside the enormous bra and turned to me, tits the size of cantaloupes swaying braless, hidden beneath her tank top. I wanted her so bad it hurt.
“There, now you’re an expert.”
My eyes were glued to the fabric tugging across her curves. Corrine glanced down at her boobs, cocking her head to the side. “Ian?” she asked coyly, “Why do you like my boobs so much?”
“I don’t know,” I sighed, raising my gaze to her eyes, “Why do you like teasing me so much?”
Corrine opened her mouth to say something smartass, but the seriousness in my tone of voice must have changed her mind. Instead, she lowered her voice to a whisper and answered, “I don’t know. I guess because I’m not really good at anything else. I’m not good at art, I’m not good at sports, and my GPA’s such a joke I might not even graduate.”
Corrine was usually the most confident person I knew. Even that small show of vulnerability couldn’t have been easy for her. I brushed a hair from her eye and pulled her close for a hug, saying, “You’re good at tons of stuff, Corry. You’re funny, you’re friendly, and you’re really easy to get along with. And yeah, you’re excruciatingly hot. Look, don’t worry about graduating! School is the one thing that I’m really good at, and I’m not gonna let you flunk out.”
Corrine hugged me back as tight as she could, letting out a deep sigh. “Sorry I got all serious like that.”
“Anytime, Corry, you’re my friend.”
“Is it cool if I keep teasing you?”
“Yes, Corry, it’s very cool.”
She grinned, wicked as ever. “Good, then you can finish my back rub!”
With that, she laid down on her stomach and hiked her shirt all the way up to her neck, revealing a slender back and a pair of magnificent breasts splashed out to the sides of her body.
I believe I actually groaned at the sight.
As the school year progressed, I made a real effort to prove myself wrong about my presumed zero percent chance with the opposite sex. I asked other girls in my class out on dates, and a few of them even said yes. That’s when I started experiencing some of the downsides to hanging out with the hottest babes in school.
My handful of relationships never lasted more than a couple weeks. It was always the same story: no matter how much I liked a girl, she just couldn’t get over feeling intimidated by my bevy of gorgeous friends. Girls always got weird about my social circle before I could even get past second base with them. One truly awful girl broke things off with me on New Year’s Eve, leaving me dateless when midnight rolled around. It may sound silly, but I had never had a chance to ring in the New Year with a kiss and I had been really looking forward to that milestone. My five beautiful friends all tried to cheer me up by kissing me after they had kissed their own dates, but it wasn’t the same. I wanted to be somebody’s first choice, not a charity case.
The situation pissed me off, but deep down I could understand. On some level, that girl was right to be jealous. Even though I wasn’t romantically interested in any of my five friends, I hardly ever fantasized about anyone else. It didn’t matter if I was dating another pretty girl, or if I had just bought pornography—whenever I was in the mood, I would inevitably picture myself with one or more of my friends, pounding away while they wrapped their supple legs around me—or better yet—squeezed their massive tits around my cock and tit-fucked me into oblivion.