Work Text:
“I’m sure we all know why we’re here.” Dustin said in a bellowing voice, calling the boys only party meeting to order.
“Last week, our cleric here-“ Dustin pointed to where Will sat nervously facing the three teenagers, “told us something shocking-“
Mike snorted, making Will wince.
“Okay, not shocking but significant-“ He held his finger up, “and we have come to a consensus.” He motioned to the three of them.
Will braced himself.
“Despite how this could complicate our lives, we have decided to stay friends with you.”
“Really?”
“But there are a few conditions, I’m sure you understand.”
“Of course,” Will nodded, ready to take whatever conditions they offer him, not expecting even this much, “I can leave the room when you change, I never looked I promise, I mean I don’t like any of you like that-“
Lucas cleared his throat uncomfortably as Will’s babbling trailed off, “That’s not what we mean.” He clarified.
Will frowned at his friends, “Then what-“
“It’s a big risk, Will.” Mike interrupted, “Being friends with a queer. You understand that?”
“Um, yeah,” He shrugged.
“So, if you want us to take that risk, it should be worth it? We should get something?” Mike asked, a weird glint in his eyes.
“I don’t-“ Will stuttered, “What do you want? I don’t have money or-“
“We don’t want your money.” Lucas said, cutting him off, “We wouldn’t blackmail you.”
“Of course not, you’re our friend.” Dustin agreed.
Will nervously tapped his fingers on his knee, “So what-“ he swallowed.
“Well, we were talking-“ Mike smiled, gesturing to either side of him, “about how this could be an opportunity.”
“Opportunity?” Will whispered.
“Yeah, an opportunity that could benefit all of us, even you.”
“What-“
“So you know how Suzie lives in Utah and Max and El put out as much they might as well live there too.”
“What’s that got to do-“
“You could solve that.”
Will’s mouth gaped, “What?”
“We talked about it. You’re small and pretty, feminine enough-“ Mike said, Dustin and Lucas nodding along, “Will you can’t expect us to act like nothings changed. You’re a fairy-“
Will flinched,
“Hey, don’t get upset. I’m not trying to be mean. You’re gay which means you’d like it. We’re handsome guys after all. It’s only right that you offer something if we’re going to put up with this for you.”
“Offer what?”
“Yourself.”
Dustin jumped in, “We won’t like touch you back, that would be queer-“
“But you can take care of us-“ Lucas added,
“And we stay your friends.” Mike finished.
Will was silent as they stared at him, frowning “Like… sexually?”
“It’s a fair trade, Will.” Mike said, “It’s also our final offer.”
“Oh,” Will sat back, “Like what?”
“Whatever we want. We wouldn’t hurt you though, just normal stuff.” Mike’s face softened, “You can think about it if you want but you should say yes,” he smiled, “You’ll like it too.”
Wills dick twitched betraying the truth in Mikes words.
He probably would enjoy it.
It was also the only way his friends would stay his friends.
“Okay,” Will whispered, agreeing.
The three boys brightened, Dustin grabbing the discarded bag beside the sofa, and thrusting it at Will.
“You should go get ready.” He ordered, jerking his head toward the bathroom.
“Get ready?” Will asked, peeking in the bag, flushing at the shock of pink lace. “I thought we were playing D&D?”
“We are, once you get ready.” Lucas directed pointed at the toilet door.
“But-“
“We’re not queer Will, that will make it easier. Go, unless you’ve changed your mind-“
“No,” Will said quickly, “No I haven’t changed my mind, I’ll do it.” He made his way to the small bathroom to get ready.
“Don’t be long.” Was said as he closed the door behind him.
His hands shook as he nervously pulled out the bright pink lingerie from the bag, tiny lace panties that would barely cover him, and a feminine silk slip cupping his non-existent breasts.
He stripped his clothes, leaving them carefully folded on the corner of the sink, slipping the panties up his legs to rest on his hips. The elastic dug under his ass, making his cheeks protrude enticingly. His cock standing at attention, poking out the top of the lace.
The stockings went on next, Will unrolling the flimsy material up his legs, avoiding snagging the fragile fabric on his leg hair. He clipped them in place to the garter belt he found deeper in the bag, and pulled the slip over his head.
He took a deep breath before returning to the room, determination clouding his features. More than ready to do this if it meant he wouldn’t lose his friends.
That didn’t stop the anxious curl of his shoulders when he stepped out and no-one said anything. All three of them sat on the sofa staring at Will standing before them in only women’s lingerie.
“What do you think?” Dustin asked the other two.
Lucas wrinkled his nose, appraising Will “Could be better but it’ll do I suppose.”
“He doesn’t look to bad,” Mike defended him, making Will blush “For a boy, at least.”
“Hmm,” Lucas responded.
“Turn around.” Dustin said to Will, who spun instantly.
“Oh,” Lucas sounded happier, “That’s better.”
“See,” Mike crowed, “Told you this was a good idea. Just fuck him from behind.”
“He does have a good ass,” Lucas considered.
“He’s got a better ass than most of the girls.”
“Doesn’t mean he knows how to use it.” Dustin reminded them, “Come over here, lets see what you can do.”
Lucas sniggered, “He should crawl.”
“Great idea,” They both agreed, “Get on your knees.”
Will sunk down immediately and started crawling to the sofa, the scratchy carpet irritating his legs despite the stockings.
“Swing those hips.” Mike ordered as Will crawled, who added a flourish to his performance, making sure his bum moved enticingly, until he was right in front of Mike, where he stopped, sitting back on his heels.
“Now wha-“
Mike lightly slapped his face cutting him off, “No speaking.” He stroked the red mark that arose on Wills cheek, “Can you do that?”
Will nodded.
“Good girl,” Mike cooed, tightening his fingers on Wills chin, “Now you’re going to suck my dick.”
Will nodded again, immediately unbuckling Mikes belt, who lifted his hips to pull down his opened pants and briefs exposing his soft cock. Mike placed his hand in Wills hair and directed his face to the tip of his dick.
“Get me hard.” Mike ordered, not removing the pressure on his head, and Will started mouthing at the tip. Rolling the pliable flesh between his lips to encourage it to plump under his ministrations. It didn’t take long for Mikes dick to get hard, growing inside Wills mouth until he was nearly choking on the length.
While that was happening Dustin and Lucas were removing their own pants either side of them, and Will found both his hands being moved to grip the hardening flesh of their cocks. He did as instructed, wrapping his fingers around the throbbing erections, and pumping in time with the way he sucked down Mikes cock.
It was hard to multitask and soon Will found he was merely along for the ride. Mike fucked his face forcefully, thrusting his long cock down his throat, causing Will to choke through his nose, saliva dripping down his chin.
Lucas and Dustin covering Wills hands with their own to set the rhythm they prefer. Pre-cum leaking over his fist and covering his wrist as they used his hands as a makeshift hole. Wills own cock, trapped in the lace of his panties, tantalising rubbing against the material.
It went on for some time until Mike ripped Will of his cock, and Lucas and Dustin released him, leaving Will to catch his breath on the floor.
They didn’t give him long before he was being carried to the table, which was quickly cleared, and placed on all fours on top.
“Wha-“ he started before shrieking when a finger coated in a cold substance began poking between his cheeks.
He was slapped on the ass by one of the boys, all of them pausing when the action made his cheeks jiggle, before the finger was back. It pulled aside the string of the panties that had ridden up his ass crack, and stroked over his furled and untouched hole.
“But-“ Will tried again, not sure he wanted to give up his virginity, squealing when he was spanked twice in quick succession.
“You know the rules,” Mike said sternly, “Besides this is what fags like.” He finished, shoving the probing finger past his rim, and Wills hole immediately clamped down tightly on the intrusion.
Will moaned, involuntarily at the feeling. “See you like it.” Mike praised him, pushing a second finger to his rim and sliding it in beside the first.
“Mike-“ Will whined, when a cock was shoved back into his mouth cutting off his whimpers, Lucas stood in front of him, his dick half-way down Wills throat, beginning to thrust his hips. Dustin grabbed his hand and directed him to continue jerking him as Mike started spreading his fingers to stretch Wills hole.
He couldn’t help bucking back on Mikes long fingers as they grazed the sensitive bundle of nerves. That appeared to be the sign Mike was waiting for, as Will found himself janked down the table until his legs hung of the edge, bent over, allowing easy access to his ass.
One moment he was empty, the next Mike had hilted his substantial cock all the way within Wills tight passage, making him scream out around Lucas’s cock. Mike didn’t give him any time to adjust, immediately pulling his hips back and removing his dick before slamming back in.
Mike set a powerful rhythm, matching Lucas thrusts, and Will found himself swinging between the two of them as they fucked him erratically. They spit roast him like he wasn’t a person, just two holes to be used.
Dustin thrusting into his hand, as he reached under Will to pinch at his perky nipples. Will sucked and clenched as best he could under their attentions, barely able to hang on. Sweat dripped down on him, Mikes hands clammy where they held Wills hips painfully.
Will thought he was about to lose consciousness when both cocks were removed from his holes, he was relieved it was over but he was wrong. The boys just changed positions, Dustin jabbed his cock into Wills hole and Will found the dick that was just in his ass shoved into his mouth.
Lucas took the time to pinch and rub at Wills exposed skin. Dustin poured more lube down Wills crack and the sloppy sounds of fucking could be heard over his sucking of Mikes cock. His hole was starting to feel rubbed raw already, and his throat was hurting.
His own dick was still hard, leaking pre-cum into the pink panties uncontrollably.
They switched again, and Will screamed when Lucas thrust into him, his cock stretching him further than either Mike or Dustin managed. It didn’t go on long before Dustin cut him off with his dick. Will was lost in pleasure as he was fucked, with not a moment of rest. He didn't orgasm but the pressure on his prostate from the constant poundings, fucked the cum out of his dick, milking him until he cock ran empty.
He wasn’t sure how long they switched between his orifices, each having a go at least three times in each hole, when Will felt the first one cum. Shooting a giant load into his ass, with a groan as they collapsed on Wills back.
A small amount of cum leaked out when the cock was removed, soon plugged by a new cock which only thrust a couple of times before adding it’s own load to the mess inside him. He expected the third one, tightly clenching as the dick was pulled out and replaced with another, pounding for slightly longer, then exploding.
Will desperately tried to close his hole when the last cock left, but the muscles were too tired, hole winking lazily in the air where he remained collapsed over the table, cum steadily leaking out of his ruined ass and down his shaking leg.
The other boys ignored him, redressing as they joked with one another, before leaving the room in search of food after working up an appetite.
Will passed out where he was, dressed in torn panties, leaking cum like a whore, and fucked silly by his closest friends.
He couldn’t wait till next time.
