On a Dare

When you think about it, it's practically bound to happen at one point in your life: you're a horny eighteen-year-old boy, hanging out with all your other horny eighteen-year-old boy friends. You're cute enough, but no girl's expressed interest... ever. So you hang out with the boys, and because you've all been bored ever since pubescence, you've played every stupid game under the sun. And when there's no adult supervision around, things sometimes get weird. Sometimes you play stupid drinking games with a bottle full of "Satan's Piss," which is some Frankenstein drink your friend (whose house you're visiting for the night) mixed together from the top inch of every bottle in his dad's liquor cabinet. AKA, a recipe for disaster. And because you're all so banefully horny as a group, your dares become weird and silly propositions that, through no vocal communication whatsoever, become a mix of jokey homoeroticism and secret titillation. One person has to do something embarrassing that the others find themselves—oops!—precumming to in their basketball shorts or their pajama bottoms, and then the circle continues with the next victim.

Yes, that's me. The liquor (if you can even call it that) is a horrifying mix of tequila, green gin, a cheap-ass vodka and small collection of Allen's dad's bourbon collection. I've had too many shots already, just like all the other boys, and there have been a few questionable dares so far. Allen, who's house we're in and made us our nasty ass cocktails, has already been stripped to his boxers (oh, what an embarrassing and not-at-all handsome display), and Josh has had to endure a long, definitely-sensual lick behind his hear from Kyle. Then there's Wyatt and myself, and Wyatt's unfortunately been asked to steal a bra from Allen's sister's room and wear it without a shirt. I've given him that dare; maybe injecting a bit of femininity into my masculine friends is a turn-on, don't ask me. But I'm last to be dared in the circle, and Wyatt (now decked out in a too-small pink lace bra) has his hand to his chin, dramatically thinking about how he might take the dare against him and turn it around tenfold. I pretend not to shiver in anticipation at the thought.

"What are you thinking, Wyatt?" Kyle asks. Kyle's easily the most forward with leaning into our teenage homoeroticism, and I get the nagging feeling he'd be glad if we all immediately transitioned into a gay orgy without question. Wyatt keeps his eye on me, despite responding:

"I'm thinking... Allen, your sister's in ballet, right?" Allen, at this point, has given up on keeping his sister's room its own private space. He sighs.

"Yes," he says plainly.

"Well, then I think our friend Landon here should go find himself acquainted with one of her leotards."

"Are you sure that's not going too far?" Allen asks, but it might be apparent from my too-calm reaction that nobody is objecting.

"You ass," I say simply.

"Who knows? Maybe if you're feeling it, you put on one of her pretty pairs of tights, too."

"You cool with that, Landon?" asks Kyle, clearly going along with it but courteous enough to ask about my feelings. We're repressed gays, yes; not assholes by trade.

"I don't back down from dares," I say coolly, and with a performative sigh I get up from the ground. "Well then, boys, until I get back, do enjoys yourselves."

So I'm in his sister's room alone. I can still hear the boys laughing from the other room every few seconds or so, their voices muted by the walls; one talking a bit louder, another responding in jest. I think they're continuing the game while I'm figuring this out. I carefully open and close all of his sister's drawers, moving on past underwear and dresses—not what I'm after tonight. Eventually in the bottom drawer I find an assortment of leotards on one side, and various dancer's tights and pantyhose on the left, partitioned in the middle by a pair of satin ballet flats. Because I'm not a pussy and because Wyatt suggested it, I. figured I would double down and wear a pair of tights as well, because—why not. I pick a mostly-opaque white pair off the top and immediately strip down to nude. I know enough from TV and the women in my own life that you have to scrunch the leg up around your hand and dip your toe in, so it's not that difficult. But this isn't exactly a sheer pair of pantyhose: they're thick, but still really tight.

I'm comfortable enough pulling them up my legs because I'm almost certain they'll fit. I'm not exactly a buff guy; I'm average, if a little bit less so. Not frail, just thin from genetics. Bigger than a teenage girl, I'd bet (if I recall, Allen's sister is... fifteen. Maybe fourteen. After some thought, I figure it would be morally irresponsible to return these items to her after tonight). Ultimately, I'm not so masculine in appearance that I couldn't look androgynous or feminine in this costume.

So I pull the tights up over my thighs, over my semi-hard cock, and briefly enjoy the sensation of the tight material wrapping around my ass and cupping my balls. The leotard, however, is an entirely different game. She has at least a dozen here; from the few that I pull out, there's a thick, matte black one, a plain blue one, and a satin-y pink one. It's obvious enough which one I need to go with: the last. I need something embarrassingly feminine and tight in all the right spots to really show these boys I mean business when it comes to dares.

I mention the girl's younger age because, as I'm stepping my feet through the leg holes, I realize this suit may be slightly too small for my body, despite my size. I manage to pull it up my legs, and the previous luxurious feeling of the tights is multiplied by how the material slides over my thighs. I do manage to get it over my hips, cupping my ass and balls, so tight that it (more than successfully) flattens my crotch to look like a ken-doll (or more accurately, a barbie) despite my hard-on. But then there is trouble, because while I can fit my arms through the sleeveless holes, it becomes far too difficult to fully wrap the suit around my body. After a couple minutes of struggling (and denying that I am struggling), I manage to finagle it around my torso, at least. The feeling is grand, and tight, and silky, the way it perfectly clings against my body. I am almost ready.

But the zipper is... essentially impossible. I would feel incomplete if I returned to the boys like this. So instead of facing the facts and undressing myself, I put both hands behind my back in attempt to zip it up again. Even with the girl's full-length mirror, it's a fruitless effort. I'm about to give up when I hear a knock on the door. I practically jump to the ceiling in shock at the noise.

"Landon?" Wyatt asks, vaguely concerned but more than anything else—obviously cheeky. Maybe he can sense I'm having trouble. "What's going on in there?"

"I'm having trouble with a zipper. I'm nearly done."

"Well, that won't do," he says resolutely, and without even asking he opens the door and walks in. More curiously, he leaves the door open behind him. "Woah," he says, pausing at the view of me. I'm still facing the mirror, my tight and round ass on full, feminine display.

"You see my dilemma. Help?" I ask, and it's good that my cock is practically tucked to perfection on its own, because my boner is practically raging. Despite the lengths we're both willing to go to, I want to keep this titillation between us repressed and hidden, even if it's so obvious. He comedically shrugs and walks over to my backside, immediately grabbing the zipper with one hand, pulling the two sides together, and giving it a tug. He makes a little bit of progress, and then a little bit more, but then there's a pause again.

"Fuck. I need more hands."

"Seriously?" I ask. "Well, I can't even reach that far up my back."

"Boys!" Wyatt yells aloud. It's a good thing none of Allen's family is home tonight—they're on some school-related overnight trip for their daughter. As if on cue, the gaggle of other boys find themselves spilling into the doorway. They yell in half-faked shock at the state of disarray, partly because no one can deny this is an absurd situation I've gotten myself into (literally and metaphorically). "Landon here needs help getting into his pretty princess costume. Can we use your hands?"

So, picture this. All the boys immediately follow in, surely aroused in some way by this but pretending they're with varying failure. With more hands than possibly necessary, they guide me: two hands are holding the backside of the suit together, two hands are instructing me to suck in, two hands aren't helping at all but squeezing my ass, and Wyatt, I'm assuming, is doing the zipping. I'm being manhandled on all fronts, feeling the tight material grip my body all over and getting caressed. One moment I'm being pulled back, then a second later I'm roughly held in place, then pushed up against the dresser. At one point, I'm so out of control of my body that two of the boys pick me up by the shoulder fabric of the leotard, forcing my body to push all its weight down by gravity, cramming my cock even further into a flatness. It works—Wyatt gains more leverage with the zipper, I suck in my stomach, and then I feel myself become entirely enclosed.

And I feel packaged in like a hot dog. The shape of this leotard is definitely made for a girl, because it has some slight firm shaping in the hips, the waist, the indication of breasts. I'm not exactly a "woman," but because the suit is too small for me, what should've been just the slightest suggestion of shapewear becomes a restrictive, unforgiving, corset-like material that molds me into a distinct feminine hourglass shape. A new girl, really, about my age, with all the material so tight that there's no wrinkle to be seen, my plain boyish shape tucked in or exaggerated on all sides. The satin, spandex material of the suit allows a sheen of light to cross over ever curve and line, and the semi-opaque white tights do the same. Even the shoes are shiny. I'm less myself than ever.

I pretend I don't like it. I'm thinking all the boys are going to pull away from me now, but there must've been a change of chemistry in the air, because none of their doting hands have left my body. Kyle brazenly slap my ass, Allen steps away briefly to get some "perfect addition," Wyatt is accentuating my waist by wrapping his large hands around my sides and pushing in, and Josh is stroking my back and pretending he's not. Allen comes back over in a flash with a pair of silver heels I didn't agree to. Instead of objecting, all the boys work together to lift me off the ground as Allen affixes them to my feet, succeeding against my surprised struggle. There's a little strap on the front of my foot that he loops in and ties. I'd lean over and undo them if I could, but I don't have room with all the boys around me, and clearly because of the strap I'm not capable of kicking them off.

"Allen," Kyle asks, "Wasn't your sister in a recital where she played a shadow? Wore like a black head-to-toe suit?"

"No, she was the fairy. Wore a pink suit. But yeah, head-to-toe. Why?" Allen asks, almost innocently. Kyle, ever the mischievous one, cheekily caresses my cheek.

"As fun as it is to see Landon blushing to high heaven, I'm having a hard time imagining him as a pretty little princess if his face is all boyish. You should find the suit," he tells him, all without my consultation. I'm about to speak up, saying, hey! Slow down! But carefully playing that line between cheeky and actually dominant, Kyle covers my mouth and shushes me. I'd fight back more if the other boys weren't teasing me in every way possible, rubbing their hands all over me, making me feel the shiny, tight material constantly caress my body. "Pink," Kyle ruminates to himself in the meantime, "Even better than I expected."

Allen, forced to rifle through his sister's stuff, comes out of her closet with a zentai in the same shiny, baby pink color of the leotard. It doesn't show any signs of being forgiving in size, just like the rest of what I'm wearing. Kyle aggressing grabs my chest.

"This won't do. Wyatt, why don't we turn this around on our dear boy Landon? Wyatt, take off that bra, give it to me. Josh, please put your tongue back in your mouth and take off the poor girl's heels."

It's like they're working to his will. Wyatt, clearly the most driven by lust, pulls off the bra in an instant. While I'm incredibly turned on, I'm wondering if this is too much. I'm sure if my cock was free I might have made a mess by now, but the way my body is tucking it tight underneath me, I'm riding an anxious high I can't come down from.

"Kyle, Wyatt, guys-" I try to say, but Wyatt hands the bra to Kyle, who doesn't waste time guiding my hands and arms through the straps, pushing the bra (literally, a push-up bra) all the way up. Wyatt works with him to keep it in place, hooking it together. Meanwhile, Josh and Allen are pulling the heels off briefly so they can work on the zentai.

I know what's happened at this point. To them, I'm barely Landon. Instead, they've let go of the homoeroticism and, at the immediate sight of a female form, latched sexually onto that instead, thinking it must be "more straight." What was once repressed homosexuality has turned into some unrepressed desire to make me into a girl.

The heels are off. All the boys are working together to get the legs of the suit over my feet while I do nothing but dawdle, protest, and scoff.

The suit it just as tight as expected, if not more so. Maybe this suit was from last season, because it might be a size smaller than the leotard. The legs, which should've been easy, are already a struggle. They can pull it up to my thighs, halfway up, but are caught at an impasse—my ass.

"I think we should lift her up at once as a team, by the waist of this suit," Kyle devises, clearly marking himself out as the devious leader.

"'Her?" I say, at a loss for words. Before I can get a grip, all eight of their hands take an inch of the suit's waist and lift up. My body is elevated off the ground, and what should've been a zentai that I never could've gotten into, something truly not made for my body, accepts me. I slip into the satin-like material, and it's tight as hell—like a second skin. I officially have no cock or balls to speak of, what with how forcefully the material makes my crotch flat. The suit doesn't even need to be pulled up anymore to reveal that I now have a thigh gap: a small triangle between my groin and my thighs that Josh unabashedly sticks two of his fingers through to test out.

The suit is resting at my waist now, practically cinching it, and the effect on my physique is obvious: it's giving me a rounder ass, and more significantly, hips. Small, but very obvious hips. Like a normal girl—not especially massive, but assuredly feminine. When Wyatt was holding my waist together earlier, to indicate an hourglass, it now looked like that without assistance. Even more cinched than that, actually. With the combined strength of eight hands and four mad-with-lust boys surrounding me, they force my hand into the sleeves and push the material up my torso. My hands slip through the sleeves just fine, but it's like my they shrink when they enter the gloves. Pulling the material up my arms is a full-team struggle that ends with absurdly tight success.

Unlike anything else before, I am both terrified and trembling on the edge of orgasm at the thought of zipping the back of the suit up. It was already so hard the first time around, and with my new breasts burgeoning through the chest of the zentai, there's even less room.

"Just put her on the ground or something," Kyle says dismissively, almost derisively, and I've basically just given up on protesting. The four boys place me stomach-down on the ground, and Wyatt carefully places his foot on my back. Not to hurt me—it doesn't hurt at all—but to give him leverage as he starts zipping up the suit.

So I have to expel all the air in my lungs, hold in my stomach, pull my shoulders backs as far as I can, and meanwhile all the boys are holding my body in a vice-like grip. I feel stuffed to high heaven. When I said I was packaged in like a hot dog earlier, now I feel like a hotdog packed into a tiny vienna sausage. They do, miraculously, pull the zipper up, then put me back on my feet. Looking in the mirror, I can see the changes right in front of me:

Pulling up the suit and manipulating it around my body meant I had to expel all the air in my lungs, giving me an even smaller, more cinched waist. The comparison has made my hips considerably curvier, and there's still no wrinkles in sight. The material presses the bra against me in a way that gives me a modest A-cup, and my shoulders look less square and masculine. Wyatt and Kyle are right behind me as I look in the mirror, their bodies pressed on either side of my back, and their heads lay on my shoulders, staring lustily into my eyes through the mirror. Josh and Allen are relegated to putting the heels back on my feet while I just sit there in shock—horny as hell, but still, shocked. Wyatt's hand, laying on my hip, slides down to my empty crotch and makes the motions for fingering, feeling in awe at the nothing. Meanwhile, Kyle kisses my neck and grabs my new tit, gives it a fair squeeze.

"Finally, for the pièce de resistance," Kyle says, and grabs the hood that still lay over the top of my chest, swiftly pulling it over my head before I can raise my hands in protest. It's really tight, but he does it quickly, deftly. I can feel it crossing over the top of my head and hair and meeting the back of my skull. The material at the front tightens over my face and especially my jaw, to the point that I can't open my mouth even if I wanted to. I grunt to indicate this, frustrated and especially turned on. Wyatt grabs my jaw and turns me to look at him as Kyle completes the process and zips the suit together. He pulls the suit's two zippers strategically to the middle of my back where I can't reach, then pats my shoulder as if I we were bros. The heels are on and strapped, I am cinched to high heaven, and I have effortless curves. There's no part left of me that's a boy, and I feel as if we've abandoned the "dare" a long time ago.

Oh, well.

"Josh, Allen, you've been absolute dears," Kyle says louder, so they can hear. "Could you two leave the room for a few minutes? With the door closed?"

"This is my house," Allen protests, exasperated. Kyle turns back to give him an intimidating look, but I can't see his expression through the mirror. I know it works though, because Allen and Josh are out of the room in a flash. Kyle gestures for Wyatt to move, and Wyatt doesn't seem to mind. He steps out of the way while Kyle moves to stand behind me, and I can feel his cock rubbing against my new bubble butt, the material so tight it creates a perfect divide between my cheeks for him to ride between. His arms wrap around me—one around my waist, and the other around my chest, reaching up and holding me by the neck.

"God, you're so fucking hot like this," he whispers. The two of us couldn't be closer as he needfully grinds against me. Wyatt sits just to the side, merely inches away, now stroking his cock underneath his pajama pants. As if realizing what he's wearing, he quickly strips himself naked and throws his clothes to the side. Kyle's in just his pajama pants and nothing else, and seeing this, Wyatt assists him by pantsing him. Still focused all on me, Kyle can barely think through his lust to step out of dropped pants.

But he does, and then there's nothing stopping him from grinding into me. His lowers his hand from around my waist until it's placed it over my empty crotch, and with the other hand, he lets go of my neck and adjusts his cock to slip effortlessly into my triangular thigh gap. I can almost see the head of his cock through the front, in the mirror, but I can definitely feel it. He starts thrusting slowly again and lets the silky material rub against his member, eventually getting faster and faster, taking advantage of the tightness. He's moaning, I'm grunting like a bitch in heat because I can't even open my mouth, and in one surprising, fell swoop he moves and throws me on the girl's bed, faced down. He assumes the exact same position over me and shoves his cock in like his life depends on it. Wyatt's breathing heavily, hands moving fast over his rock-hard cock. The girl's sheets are soft and silky too, and I'm practically slipping under Kyle's grip, despite how firm it is.