Interactive Story - Greg's Naked Nightmare - Part 7 (Patreon)

For part 6 click here 

Part 6 Voting Results

Greg has been offered clothing to make his journey home less embarrassing, but it comes with a price as he gets caught up in a bet between shool friends. How far is he willing to go to cover up?

1. Agree to let Wade fuck him – 0%

2. Make a run for it and try to get home – 25%

3. Agree to let Wade fuck him, but only if he fucks Dill first – 75%

Part 7

The nightmare needed to end. Greg’s nudity had pushed him into embarrassing situations and terrible decisions, but so far none of the damage appeared to be permanent. Assuming his neighbour hadn’t recognised him as he leapt from the truck several minutes ago, nobody from Greg’s actual everyday life had yet seen him naked and this was possibly his last chance to keep it that way.

As he looked from Wade to Dill and back again. Could he really let this guy fuck him? Though he would never admit it to anyone, Greg had played with his butt before. In fact he rather enjoyed it, but it had neve been anything more than a solitary finger for a brief moment right before he came. The scrawny kid couldn’t have been packing that much, but even a small dick is a bigger challenge than a finger.

The grin plastered over Dill’s face was infuriating. The puppet master of the imminent encounter, a spectator to the misery (or maybe pleasure, that was yet to be determined). He would win his bet without paying anything for it, unless…

“I’ll let you fuck me,” Greg said confidently, then let a small smile break out as he continued, “But only after I see you fuck him!”

“Yeah, no fucking chance!” Dill scoffed.

Greg shrugged. “Oh, then… no. And enjoy losing your bet!” he said, hoping Dill wouldn’t call his bluff.

“Dill, c’mon, he’s… willing, and we REALLY don’t have long left!” Wade did his best to convince the other boy.

Greg couldn’t help wondering whether Wade really thought this was their best shot, or whether it was just a chance to have a go on Dill, but he sounded convincing either way.

“Ugh, fine, but… we’re going inside!” Dill said, looking back to the house.

“You were gonna make us do it out here?” Greg asked in shock.

“Whatever, let’s just get on with it,” Dill huffed as he hurried back towards the house. “Relax, my dad’s already left for the day!” he said, seeing Wade’s obvious reluctance.

Greg hurried across the front garden, nervous of being seen by anyone passing, but he made it inside with the others without being seen. Hopefully that would be the last time he ever had to set foot outside without clothes.

“Here,” Dill said as he reached into his blazer pocket and pulled out a condom.

“You just… carry these around with you?” Wade asked, suddenly nervous at the realisation of what was about to happen.

“Only since the bet,” Dill shrugged, pulling out a sachet of lube. He looked to Greg and said, “He does me for ONE minute then he does you til he finishes!”

“Great,” Greg said flatly.

“Ugh, this is SO stupid,” Dill huffed as he undid his trousers.

For some reason, Greg had expected the two boys to get naked, so he was a little surprised when he saw Dill kneel on the stairs with just his butt exposed and Wade with just his dick pulled out through the open zipper of his own trousers. Even more surprising was the size of Wade’s dick. He was stroking it as discretely as he could, but it was growing rapidly and getting less discrete by the moment.

“Jesus Wade,” Dill exclaimed, looking a little pale. “Definitely a grower!”

“Hnnh, yeah,” Wade giggled awkwardly before opening up the condom and beginning to slide it on. He kept fumbling with it, struggling to get it started.

“It’s… you just… you need to…” Greg started, but couldn’t find the words. “Here, let me!” he said, taking the condom from the teen. As the others looked at him in shock, he said, “What? He’s about to fuck me. I think we’re past the ‘oh my god he’s gonna touch his dick’ phase!” The comment was borne of sheer frustration, but still managed to make both of the others laugh. “And you need to lube up, but save some for me. I ain’t taking this thing without lube!”

Dill nodded compliantly and blushed as he reached back to start lubricating his hole, though his blushes were unnecessary as Wade’s attention was entirely on Greg as he took the condom, got it in place and started rolling it down the rigid prick.

“Ya get it now?” Greg asked as he let go.

“Yeah, thanks,” Wade blushed. “Are you… ready?” he asked Dill nervously.

“Ready as I’ll ever be!” Dill replied, pulling out his time to ready a timer. “And go easy. This ain’t my thing!”

“Sure, but getting fucked by a schoolkid to earn myself some clothes is totally my thing,” Greg muttered sarcastically.

Wade grinned at the comment, then moved forward to press the head of his dick against Dill’s hole.

“Timer doesn’t start til he’s in,” Greg said, partly to prolong his tormentor’s suffering, but also in a vain attempt to ensure Wade was as aroused as possible which would reduce his own time impaled on the meaty rod.

“Ugh, fine,” Dill huffed. He steadied himself on the stairs as Wade slowly started to push in.

“How does it feel?” Wade asked curiously.

Dill scowled back at him and snapped, “How d’ya fucking think?”

“He’s probably hard!” Greg said with a snigger.

“Takes one to know one,” Dill snapped back, sneering at Greg’s semi.

Greg blushed as he realised he was definitely a little thicker than he had been when they started. It didn’t seem possible. He had cum twice already that morning, one of which had been barely fifteen minutes earlier, yet he could definitely feel himself getting harder again.

“Okay, that counts as in!” Dill gasped and started the timer.

“Okay then,” Wade said, taking it as his cue to really get started. He pulled back and pushed back in. He had never fucked anyone before, but he had certainly fucked a few inanimate objects. Just last Halloween he had found himself alone with a pumpkin, though that’s really another story. He did his best to fuck his friend without hurting him too much, but he lost himself a little in the pleasure – so much so that he barely even noticed as the timer went off.

“Okay, geddoff!” Dill grunted, pushing Wade back before quickly covering up his butt.

“Have you… got another one?” Wade asked as he reached down to pull off the condom.

“Here,” Dill said, reaching into his pocket before handing another condom back without looking round at either of them.

“Thanks,” Wade said as he took it and quickly ripped it open. He copied what he had just seen Greg go and quickly had it rolled down over his dick, ready to start over with Greg.

“Lemme kneel there,” Greg said, pulling Dill back. “Wow, I was only kidding, but as it turns out…” he said, looking down at the obvious tent in Dill’s trousers.

“Dill, did you…” Wade started, shocked.

“Shut the fuck up!” Dill snapped angrily, “Both of you!” He turned away and ordered, “Just fucking do it!”

Greg smirked at the annoyed reaction. At least his wasn’t the only dick that was in the business of betrayal today. He grabbed the lube packet from the stair where Dill had left it, squeezed out the rest and reached back to finger himself briefly.

“Okay then,” Wade said without hesitation. He moved in and repeated what he had just done with Dill, slowly working in, though this time he had no timer and as he slowly started to build a rhythm, he knew the only goal was to cum. There was no way Dill (or the others) would be satisfied unless he could prove he had finished the deed.

“Ah yeah, perfect!” Dill suddenly called out.

As the other two looked round, they saw Dill holding out his phone showing a picture of them mid-fuck, the angle perfect to show Wade’s dick entering Greg without showing much else of him.

“Wait, is that legal?” Greg asked nervously.

“No really, I’m only twelve!” Wade said.

“WHAT!?” Greg yelled out in shock.

Dill and Wade both burst into laughter as Wade explained, “Just kidding… oh, bad choice of words!” They both laughed again. “Chill dude, I’m eighteen. I’m legal and so’s the picture!”

“That was too good,” Dill laughed, shaking his head. “But hurry up. We’re already gonna be late for school!”

“Fine,” Wade said, shaking his head before turning his attention back to Greg. “Stand up!” he instructed, pulling at Greg’s shoulder.

Greg stood and let out a slight grunt at the way the move pressed the teen’s dick onto a different spot inside him. He felt Wade’s arms wrap around him and his mouth on his shoulder, kissing and nibbling gently as the fuck went on. Surprising as it was to realise, it felt… pretty amazing. The fuck was eager and firm without being rough, while Wade’s hands were so delicate as they roamed his body.

As Greg turned his head a little to look at the teen, his lips were immediately met by Wade’s. Greg had never been fucked and he had never kissed a guy before. Two firsts at the same time. Were it not for the nightmarish morning, this might have actually been a pretty wonderful day.

Wade moaned into Greg’s mouth but eventually pulled off as he gasped. “Ah, oh fuck, fuuuuck!” He gripped on tightly as his cock spasmed inside Greg’s rectum.

A few moments later, still panting heavily, Wade pulled back. Dill was immediately up close with his camera pointed at the other boy’s dick. He snapped a picture of the cum-filled condom then said, “Okay, you head off to school. I’ll sort some clothes out for… fuck, I don’t even know your name!” As he saw Greg go to speak, he shrugged and said, “And it turns out I don’t care. Go on Wade, I’ll catch up!”

“Oh, okay,” Wade said with a nod as he pulled the condom off and put his dick away. He watched as Dill pushed past Greg and ran up the stairs then looked to the naked young man and said, “Thank you. That was… fun!”

Greg blushed as he replied, “Yeah, it… kinda was!”

They stared at each other for a moment before Wade leaned in for another brief kiss on the lips before he turned and left the house, full condom still in hand.

Greg watched the door for a moment. It was strange. He didn’t necessarily feel any attraction to the teen, but it had still been a surprisingly tender moment. They had popped each other’s cherry, yet they would likely never meet again. He wasn’t sure whether that was beautiful or awful. He was shaken from his thoughts by the sound of Dill returning, a bag clutched under his arm. He quickly picked up the lube and condom packets and stuck them in his pocket before nudging Greg towards the door.

“Wait, my clothes!” Greg demanded.

“Yeah, outside,” Dill said dismissively. “I ain’t standing around waiting for you to get dressed. I’m already getting detention for this shit!” He nudged Greg out, then shut and locked the door behind him.

Greg glanced at the street, but thankfully was able to remain mostly hidden from anyone who might happen by.

“Y’know, if you’d just done what I said, you’d be wearing sweats by now, but you had to go and drag me into it,” Dill said coldly.

“Oh yeah, and you clearly hated it!” Greg said, knowing he probably shouldn’t tease.

“Fuck you!” Dill snapped. “Here, they gave me these cos they were so sure we were gonna lose the bet, but I guess I don’t need ‘em now!” He reached into the bag and pulled out a black lacey bra and matching panties. “Have fun, homo!” He didn’t even wait to see the reaction, he just ran off down the driveway and disappeared around the corner.

“Fuck!” Greg grunted. Why couldn’t he have just kept his mouth shut and done what he needed to. Staring in dismay at the ‘clothing’ now in his possession, he tossed away the bra. Even if it could cover part of him up, the embarrassment of wearing it would have been worse than just being topless. He wondered whether the same applied to the panties. With a groan, he reached down and stepped into them, pulling them up to tuck his still-semi-hard dick and balls into them.

Though lacey, the front panel was not transparent, though the cut meant it was exceptionally difficult to contain all of himself in it. He eventually managed, though they were stretched a little to contain him fully and threatened to let him pop out at any moment.

Not feeling any less exposed than when he was naked, he rushed down the driveway, checked the coast was clear and continued down the road. Despite being stranded in virtually no clothing, existing in a constant state of semi-arousal and still nursing a bitch of a hangover, Greg finally started to feel like luck was on his side as he made it down a few more streets without being seen. He had to hide a couple of times to let people pass, but he remained unspotted.

As he reached the end of the next street, he found himself facing a choice. The road ended in a T-junction. Straight ahead of him was a pitch that was used by the locals most evenings and weekends to play football and used throughout the day by local dog-walkers. His house was right on the other side of it. Going either way meant several more minutes of walking, possibly more if he had to hide from anyone. The left took him dangerously close to the pub he bartended at occasionally but was in an area that was pretty dead at this time of day, while the right was less likely to lead him towards a familiar face, though it was much busier. He was so nearly home, but which way to get there…

For part 8 click here