Date: Fri, 7 Jul 2023 11:36:00 +0700
From: Andrew Passey <andypassey69@gmail.com>
Subject: Shipperton Rules Part Nine (Young Friends)

"We don't have to do this, just because Dad says we do and the stupid
fucking rules do!" Ken said vehemently as Nick came into Ken's bedroom
from the ensuite bathroom having just had a nice hot shower. Ken was
already lying on his big double bed in a towel having showered just
before.

It was Saturday night and both boys knew what needed to happen that
night. They'd had a nice evening of pizza and watching a movie, ignoring
the elephant in the room for as long as they could. They'd both showered
in Ken's en-suite bathroom (separately) and brushed their teeth. Now it
was time for the main event. Ken had felt extra awkward when his Dad had
sent them off to bed with a message of "Remember the rules are the rules
and trust you to follow them," and now the tension in the room was
palpable.

"We promised him we would," Nick replied even though he knew he'd be
more than happy not to do this. Despite his words he was still hoping
there would be a knock on the door and Jeremy would be there all smiles
and telling Nick there had been a big misunderstanding and that he was
off the hook. However Nick knew that time had passed and that there was
no way to avoid his fate.

"Fuck him, fuck the rules, fuck Shipperton!" Ken said bitterly.

Nick sighed, "Yeah but he trusts us to follow through with this. I
signed up for this. You did as well. So yeah...I guess rather than fuck
the rules it's fuck me."

Usually Ken would have giggled along with Nick as he made his joke but he
didn't feel it was a laughing matter. He hated seeing his best friend so
despondent and again hated himself that he definitely felt some level of
excitement about what he was going to do to him. The silence in the room
grew with both boys not wanting to move things forward before Ken
eventually cracked.

"So.....this is awkward," he said as he watched Nick not knowing whether
he should get on Ken's bed like he usually would for their sleepover or
do something else. They'd always slept in Ken's big double bed but now
it had extra meaning and the awkwardness in the room was palpable.

Nick exhaled and gave a short laugh, "You're telling me! This is so
fucking awkward it's painful!I've not even seen you naked for ages and
now you're going to be...um...you know...um fucking me."

"It's weird for me too," Ken replied with a shy smile at his friend.

"Yeah and your parents know what's going to happen tonight. They
literally know the next time they see me that you'll have had your dick
up my bum and shot your cum inside me!"

"You really do have a way with words," Ken giggled as he said this which
Nick joined in with despite himself.

"Three year, 365 days, that's at least 1095 times you're going to fuck
me. If it's only once a day! If it ends up being double that then that's
well over 2000! But 1095 times minimum which sounds huge!" Nick said
trying not to sound as panicked as the sheer quantity made him feel.

"Actually 1096, next year is a leap year. Sorry, I worked it out too,
Nick."

The room went silent again before Nick decided the waiting was making
things worse.

"We both know what we need to do. How do we do this?" he asked nervously.

"I suppose we should take our towels off first," Ken replied, feeling as
nervous as Nick sounded. It was strange he thought, they'd been naked in
front of each other for years, at least until recently when puberty had
struck them both. Yet now it all felt heavily loaded with the knowledge
of what was about to come.

Nick pulled his towel off and so did Ken. Nick looked over to his friend.
He hadn't seen him naked for a while and Nick was relieved to see Ken's
dick was still small. Ken looked back at his friend and marvelled at how
he looked naked. His dick was bigger than Ken's although nothing like
Paul or Christian size with a beautiful little patch of wavy blond hairs
surrounding it.

Nick continued to examine his friend and could see a light dusting of
small black hair round his dick and balls. Ken had clearly started
puberty but his dick had barely grown.
Although as Ken smiled at Nick nervously, Nick saw Ken's dick start to
grow and harden. Ken blushed and started to stammer an apology but Nick
stopped him

"I didn't realise I had that effect on you," He said, forcing a giggle
and trying to lighten the mood as Ken continued to try to apologise.
"Look, it's fine. You need to be..um...hard to get inside me and so yeah
it's fine. I guess I'll just lie on my front on the bed, just
um,..please make sure you use lots of lube."

Nick then walked over, got on the bed, lay on his front and waited
nervously. It felt all business like, what was going on. If this was his
first time with a girl or even a boy he was romantically attached to then
there would probably be kissing and foreplay but here it was something
else. Something  he just needed to lie down and take. He recoiled
slightly as cold lube was squirted liberally between his parted bum
cheeks and then rubbed in.

He then felt them go back together before a moment later he felt Ken's
hard dick slide between those very same bum cheeks. Nick tensed as he
felt the tip of it touch his now slicked up hole. He then felt Ken's hand
stroke his neck gently,

"It'll be okay. I'll be gentle," Ken said as he pushed forward, his
hard dick slipping inside for the first but definitely not the last time.
This caused both boys to groan, Nick in a bit of pain, Ken in what Nick
suspected was pleasure. Nick clenched his teeth as he felt the tip of the
dick enter and then the rest of Ken's dick push all the way in.

"So tight and warm! " Ken said enthusiastically he started to push in and
out of Nick. Nick found it very uncomfortable at first and just gritted
his teeth, trying to ignore the pain. Then to his embarrassment and
mortification he started to feel his own dick hardening with all the
internal stimulation as well as the friction of it against the bed until
it felt as hard as it had ever been. Pushed up against the mattress by
Ken on top of him there wasn't anything Nick could do with it. Even if
he'd wanted to wrap his hand around it there wasn't room to. Ken
continued to thrust in and out before he suddenly stopped.

"Have you finished?" Nick asked slightly hopefully but also slightly
confused as he hadn't heard Ken make a noise to suggest he'd just cum
nor had he felt anything inside him.

"No I....do you mind if we change positions? It is...it just feels
really...I dunno impersonal to not see your face. Can we try on your back?
Maybe lift your legs up or something?"

Nick was conflicted. This would mean Ken would see that his own dick was
hard and he also thought it would probably be weird to see his best
friend's face wrinkled in enjoyment as he fucked him. As he ultimately
came inside him. Nick wanted it to be business-like. He'd lie down and
let Ken do what needed to be done. This way added a lot more emotional
complications and nuance than he was comfortable with. But Nick wanted to
keep Ken happy so just simply said "okay"

Ken pulled out of Nick and got off him allowing Nick to roll over, "Wow!
Did I do that to you?!" Ken said proudly pointing at Nick's hard dick.

Nick blushed and didn't know what to say. Was he enjoying it? If he was
honest with himself then....maybe... yes, at least a little bit. For some
reason the stimulation when Ken was inside him was making him feel really
good.  Nick couldn't meet Ken's eyes though, he felt mortified that Ken
could see this.

"Hey Nick, look at me," Ken said. He looked at him and his expression
was soft and gentle, like he was as a person. "It's nothing to be
ashamed of. I'm just pleased you're getting some enjoyment out of it .
Now let me lift your legs up, yeah like that, okay let's try this
then!"

He pushed inside Nick again and then smiled at him gently,"if you were
enjoying it before think how good it's going to feel now when I wank you
off at the same time!"

Ken then wrapped his hand around Nick's hard dick and started wanking him
at the same time as he started thrusting inside his friend again.

"Uhh...Fuck......fuck......." Ken said between grunts as Nick finally let
himself go with it, letting whatever worries he had about enjoying it
drain away. At that moment there was just Ken, his dick inside Nick and
his hand wanking Nick's hard dick. Nick was now also making appreciative
noises, the room was quiet apart from that and the slap slap slap sound
of skin against skin. Then with a loud grunt Nick shot over Ken's hand,
the intense orgasm causing all of Nick's muscles to tighten and squeeze
the hard dick inside him which then set Ken off as he shot inside his
best friend for the first time.

Ken kept thrusting away expelling every last drop of cum from his balls
before after getting his breath back he pulled out and started cleaning
them both up with tissues that he was able to reach with his hand. Nick's
legs were still up around Ken's shoulders and he felt exposed. There was
an awkward silence as both boys realised there was no going back from
what they'd done.

"So 1 down, 1095 to go. God that was fucking amazing!" Ken said, breaking
the silence enthusiastically. He smiled down at Nick and continued to
talk, "It was so tight and warm inside you! Like really hot! So much
better than wanking. And when you came and your hole tightened around my
dick? Best. Thing. Ever! How was it for you?"

"Um..." Nick wasn't sure what to say. The truth? Maybe he did actually
enjoy a bit of it, actually more than a bit, maybe most of it? But if he
did what did that make him? Gay? Bi? Was it just his body responding?
Would it be like this with every boy? He doubted it, Mike made out that
it was a nightmare at first. Maybe because it was Ken it was a little bit
nicer than he was expecting, maybe even slightly special? But if that was
the case what did that all mean? Was Nick trying to ignore something that
was trying to push through to the forefront of his brain?

He tried to think of something else and Ken then started chattering again
which helped.

"If you'd told me a couple of weeks ago I'd be losing my virginity AND
wanking my best mate off at the same time I'd never have believed you!
Fuck, I'm hard again talking about how amazing fucking you was! I never
wanted it to stop! I can't wait until we do it again tomorrow!"

Ken moved excitedly as he said this and his newly hard dick ran up the
crack of Nick's bum  causing him to jump slightly. Nick looked up as his
friend who was smiling almost expectantly at him. Nick sighed to himself.
No point in fighting it, Ken's enthusiasm was infectious.

"You can...you can do it again now if you like," Nick said softly.

"Really?!? I mean I never wanted to stop, you're the best!" Ken replied
pushing back inside Nick without a seconds delay, it was still wet and
sticky from a few minutes earlier and he slipped in easily. Nick didn't
know why he said yes but he let Ken pound away at him. It actually felt
pretty good but he thought he might be sore in the morning. Being
penetrated twice was something he definitely wasn't used to. Again the
stimulation of being fuck meant that his dick hardened again and Ken
started to wank him off again, leading to the inevitable conclusion a few
minutes later of  both boys having their second orgasm of the night
almost simultaneously.

It took a while to clean up afterwards but soon both boys were tucked up
in bed together. Nick couldn't sleep though. Ken snored gently next to
him and he thought Ken was probably exhausted and totally sated by
fucking Nick twice. Nick didn't really know how to process what had
happened. He'd let his best mate fuck him twice, the second time when he
didn't actually need him to. Nick had to admit to himself he'd sort of
enjoyed it. He'd cum twice with Ken's hard dick inside him. Those little
questions from earlier came back to him. Was he gay?

Nick thought he still liked girls so maybe he was into both boys and
girls or maybe something he'd always buried was unlocked? Nick guessed
his conflicted thoughts didn't really matter. In the morning Ken would
fuck him again and then possibly other boys would for the rest of the
week and the next three years. Nick realised he was just a convenient
"tight warm hole" for all of them including Ken.  That's all. A better
substitute for their hand. There would be no emotions involved, just the
physical act of anal sex. Something he had never thought would ever be in
his life a few weeks ago. In fact Nick didn't even quite realise it was a
thing until then. Now it was something that might be about to take over
his whole life