Date: Wed, 19 Feb 2020 15:21:21 +0000
From: Cliffy B <bootusrim@gmail.com>
Subject: Desperate Times 10

Desperate Times 10

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All events are fiction. All characters are a figment of imagination.

As I try to get my brain and breathing back to normal, I feel Lee getting
off the bed beside me. I'm not quite sure what to do or say. My horniness
satisfied - for now - I start to worry; Is Lee going to regret this? Was
this the first time he's sucked a dude off? I know it was my first time
getting a blow job, but I have to say; it was pretty amazing.

"Fuck, that's a hot sight." I open my eyes, looking up at Lee - looking
down on me - horniness still in his eyes. "Dick's going to be raging all
the way home." Lee gives me a wink before awkwardly stuffing his dick back
into his trousers.

"Well, if you want, I could help get it down before you go home." Propping
myself up on my hands, I notice how Lee's fully dressed while I'm
completely naked.

"Fuck mate, wish I could. Really I do! I know it looks like I'm doing a
dump and run, but I actually need to go." Lee looks genuinely apologetic as
he gives his hard cock a squeeze through his damp trousers. "But, I've got
to go home, clean myself, get ready and go to Katie's to help with `party
preparations'. Believe me; I'd rather stay here with you." Lee leans down
and plants a quick kiss on my lips before making his way to the door.

"Oh, no worries dude. I mean, if you want to do this again, just, uh, let
me know." I shuffle to the end of my bed, looking for clothes to put on so
I can show Lee to the door.

"Actually," Lee stops in the doorway and turns back towards me, "I don't
suppose you're free this Friday evening?" Getting off of the bed, I slide
my football shorts up over my legs.

"Uh, far as I know, why?" There's a large part of me hoping Lee's going to
invite me to the party. I've never actually been invited to a party
before. Only ever went to one guy's house for tea. That's as far as my
after school invites go during Secondary school.

"Well, would you like to come to the party Friday? Katie's parents will be
out, so it's going to be a big end of school bash." I can barely hold my
excitement. Lee Metcaff is inviting me to a party.

"Um, yeah, I'm sure I could come." I try to act cool. It might be dumb, but
it's nice to finally have friends. Even if they did come right at the end.

"Awesome. I could really do with you there ..." Lee hesitates a moment, a
look of worry in his eyes. "You see, Katie's decided that, with school
over, she doesn't need a trophy boyfriend, so she's decided that Friday
will be the night we break up. In classic Katie fashion, it has to be a big
dramatic affair. I've got, like, a script and everything," Lee rolls his
eyes, "it involves me being a cheat for some reason. Though, I suppose
that's technically true now." He gives out a sudden laugh. I just give him
a friendly smile, unsure of what to say. "But don't worry, it won't be
until, like, the end of the party, so you can still come along and have
some fun before the fireworks." Looking me in the eyes, Lee traces a finger
over my abs. "And, maybe after, we could go somewhere together?" My cock
gives a slight jolt.

"Um, yeah, sounds good." I smile back at Lee. Now I really can't wait to
get to Friday!

"Awesome. Seriously though, really sorry I've got to fly. I'll make it up
to you! I promise!" Lee turns away, and I follow him to the front
door. He's just given me my first blow job, what's he got to be sorry
about?

Waving Lee's car out of my drive, a silver Audi pulls into next door.

"Hey, Mr Cody." I wave to my hot, muscular neighbour.

"Hey, Tim, how's it going?" Dressed in a button-down shirt and smart
trousers, you can still tell the body underneath is in good condition.

"Not bad. Just looking forward to Friday." I give a smirk at my own double
meaning.

"Oh yeah, last week of school. Well, good luck with the exams, Tim." Taking
a bag out of the boot of his car, Steve makes his way to his front door.

"Thanks, Mr Cody. See you later."

"See y'u, Tim." Turning back into my own house, I swear I saw my neighbour
give me a sly wink.

Climbing the stairs, I can't help but think about Lee. I've spent the last
seven years of school admiring him. His good looks, his body, his
abilities, his friends, his larger than life personality. Hell, I've even
admired his relationship before. However, that doesn't seem to be the real
Lee. The person I knew would never have been so ... sweet? It's obvious he
likes kissing, but he's always played the big man part, someone who's much
more 'treat them mean, keep them keen'. Just goes to show how much you
really know someone.

* * *

Walking home at two in the afternoon's pretty weird. School usually
finishes at 3.20, however, after two hours of English revision followed by
two and a half hours of English exams, the principal gave us permission to
go home early. He obviously realised that no one's going to be in the mood
for more revision after an exam.

I got to talk to Bobby a bit after. I did ask him if he wanted to come back
to mine, totally innocently, of course, however, he said he had to go
shopping with his mum. They're going on holiday to Spain at the weekend, so
they need to get supplies. Apparently, Bobby tried on his trunks, but they
were barely able to get over his ass. Bobby's quite a slight guy, so how
old these trunks must be I do not know!

I'd have tried to speak with Lee, however, he was amongst his group with
Katie dragging him around by his arm. I decided I should stay away. He's
been keeping me updated on the state of the party through messages. Booze,
catering, decorations. The full nine-yards! It helps Katie's parents are
pretty loaded. Joint partners in some big law firm. To be honest, it's
actually kind of intimidating; where do I fit in? Hopefully, they have a
pet I can spend the night with, hidden away until Lee's free.

It kind of sucks how I wasn't able to see Lee naked yesterday. I've gotten
glimpses of him in the changing room, but never got a good view. Especially
not of his ass. I know he's got muscular cheeks, but I'd love to get up
close and personal with them. Also, I'd like to get a view of his
hole. I've watched enough porn to know I want to try rimming and I
definitely know I want to try fucking! The only question is: do I want to
get fucked?

I admit; I've always kind of shied away from my own hole. I guess I've
always thought getting fucked was too gay. Stupid, I know! But, I guess
that's the kind of complex you get when you're desperately trying to keep
anyone from finding out you're gay.

Despite my internalised homophobia, I've looked up about how to prepare for
anal, about fingering and items you can use for practice. The only thing
that's stopped me experimenting in the past is the lack of being able to
... clean myself out. I've had a little play with my hole in the shower
before, however, I've always been too scared to actually insert anything.

The thought of Lee and holes is starting to have an effect on my cock, that
horny ache in my balls telling me they need some release. Be amazing if Lee
or Bobby were free. Parents aren't going to be home until around six or
seven, would have given us plenty of time to have some fun. Or it could
give me plenty of time to get a bit exploratory. If only there was a way of
cleaning myself.

Getting home, I go straight to my room. Stripping off my uniform and
putting on a t-shirt and football shorts, I log onto my laptop and I go
straight to my favourites. I click on a gay forum I've been going to for
years. Being closeted, it's been my main source of information. Also meant
I've been able to talk to other gay guys without fear of being outed. It
has threads about porn, areas members can post pics of themselves, but also
a pretty active community where people talk about gay issues.

Doing a quick search, I can't really find any threads about how to clean
yourself without the appropriate tools. Lots about the importance of
douching, how to use a douche properly and discussions about whether or not
members do douche, but none that helps someone who wants to be clean, but
not the means to acquire the equipment. I mean, sure I could order
something from Amazon, but if my parents found out what's inside there will
be a lot of questions that I'm not ready to answer. I'm sure they wouldn't
open my mail, but dad might mistakenly open it thinking it's his, or the
packaging might be ruined during delivery enough to make out what's
inside. It's too risky. Plus, it doesn't help me right now.

Probably be easier to just make my own post, to be honest. I know I could
google it, but it might be useful to others on the forum, plus it'll be
nice to have some form of social contact. Sure, through a computer, but
still. Also, someone on the forum might have a solution others haven't
thought of before. So, no reason not to really.

`Hey, never done any butt stuff, but been really tempted lately. The only
problem is I've not got any equipment to make sure the back package is
clean, so I'm just wondering if anyone has any advice on a makeshift way of
making a douche."

Quick and to the point. Now I just have to wait. Checking the rest of the
forum and watching some Youtube, I check back after an hour.

Three comments: Two telling me to google it -very helpful, thanks - but one
guy seems more willing to help:

`I know the struggle man. If you want advice hit me up in the discord.'

I've never been a part of the Discord before. One, I've never bothered with
discord, and two the thought of direct, instant contact with other gay guys
on the forum makes me a bit ... nervous? Don't know why, it's not like
they'll be able to see me, or know where I live or who I am. Maybe it's
because, technically, the forums are for over 18's only, what with the
posting of porn, however, I've been a member since I was 16. A bit naughty
of me, but it's why my profile says I'm 20, not 18.

Clicking on this guys profile, I decide to check him out before committing
to a conversation with him. Apparently, 24 (though that's not necessarily
true), lives on the East coast of America and posts a lot in the advice
threads. Unfortunately, he doesn't seem to have posted any pics of
himself. His avatars a pretty cute picture of Conan Gray. Be nice if it was
Conan Gray, however, I highly doubt it!

Downloading Discord, I make an account and use the same username as on the
forum: Footy lad. Original I know! Adding the forum's server, I look
through the usernames to find the guy who commented: BostonNoSocks.

Thankfully, I didn't need to search for long as a private message flashes
up; `Hey man still need some advice?'. I assume it's the same guy,
different username, but seems to know what's up.

`Hey you BostonNoSocks?' Just in case. It's good to know who you're talking
to.

`Yeah thought it'd be easier if we chatted here.' He's not
wrong. Especially if it's a bit more complicated than sending a simple
link.

`That's cool.' Asking a stranger to help me play with my ass is getting me
kind of horny. It's a bit naughty, you know?

`The easiest thing is if you've got something with a long nozzle. When I
was younger I had a squeezy ketchup bottle that I bought for like 50
cents. There's also a honey bottle that I've seen people use.' I'm glad he
said he bought one - not just used one from his cupboard and put it back
after!

`I'm pretty sure I've got nothing like that." All our sauces come from a
Heinz bottle, and they do not have a long nozzle. I've never known us to
have honey in the house.

`Okay, how about a drinks bottle with a long straw or one of the new ones
that have those rectangular mouthpieces. They're short but might do the
trick.' This is definitely the right guy to ask!

`Sorry not got any of those either.' I'm starting to feel a bit bad like
I'm turning down his help, even though I know it's not really my fault.

`Heh, no worries. The only other way is a bit more fiddly. You got a
plastic bottle? Like from a coke or bottled water?' Success.

`Yeah one in my bag.' Don't know why I'm being so specific.

`Nice! Next items a bit less likely. You got a drinking straw?' As fate
would have it we do. My parents make Iced Tea during the summer and my mum
has to drink it through a straw. Not good for the environment, I know.

`Yeah got a whole bunch.' It's pretty obvious how the two items come
together to make something to douche with, but I wait to hear his
explanation anyway.

`Cool. Now you can either make a hole in the top of the bottle and stick
the straw through, or take the lid off and use sellotape to keep the straw
in place and make sure no water leaks out.' Very self-explanatory, I'm not
sure why I didn't think of this myself.

`Awesome! Thanks dude!'

Getting the bottle from my bag, I raid mums straws and get some sellotape
from the kitchen bits draw. Putting it all together, I realise my
mistake. Taking off the sellotape, I fill the empty bottle with water and
re-seal the straw to the bottle.

Back at my computer, BostonNoSocks has left a message: `glad I could help'
- Hopefully he can help further!

`Hey I've never done this before. Any tips on how to actually do it?' I
know it sounds simple - shove it in, put water up my ass and let it out -
but I'm sure if there's a way for this to go wrong, I'll find it!

`The most common rooky mistake is not taking a dump first. Can get really
messy. Only other thing is when you're inserting the straw make sure you
push your hole out a little. Also be very careful when inserting the straw
the edges are a little sharp. You don't want to cut your ring.' See, I'd
never have thought of any of that. Probably ended up covered in shit and
blood.

`Thanks again dude!' Wonder if he's hot. Be nice if he'd be able to give me
a more hands-on demonstration if he is hot.

`No worries. You might need to do a few refills and the bottle will
probably be crinkled and unusable after. Just do it till the water runs
clear and you should be good to go.'

I'll save you the details. I am not into shit. The only thing worse is
vomit. Took me about fifteen minutes till the water was clear, the last two
goes being a bit tricky as the bottle ended up being pretty crinkled - Just
as BostonNoSocks said it would be.

`So you bottom often?' Naked and with a clean anus, I decide to continue
talking to Boston. Maybe get a chance to see what he looks like.

`I'm verse so I get my share of dick. Though I've got an actual doucher
these days so a lot easier :p' I know it's unlikely for a dude on a Discord
of a gay forum will be hot, however, I've never had a conversation about
how someone likes to fuck before. It's getting my dick a bit
excited. Though, to be honest, it's been half-hard since I first started
talking to Boston.

`Lol. Not to be annoying but I don't suppose you have any tips for playing
with my hole do you?' Maybe I'm just being overly British, but I feel a
little bad about asking him so many questions.

`You're not being annoying. Happy to help. I can give you some advice
though to make it specific for your hole I might have to see it first ;)'
The flirtings escalating quicker than I thought it would. Though I guess we
did start the conversation about my ass, so I'm not sure what I expected.

`Would I be able to see yours?' Maybe a pic swap won't be too bad. I've
never sent pics of myself to anyone before.

`Sure! Can use video chat if you want. Make it easier. Believe me taking
pics of your hole is not easy!' He makes a convincing case. However, do I
really want a random stranger on the internet seeing me naked and playing
with myself? My dick's been hard since he implied he wanted to see my hole,
so I know I'm horny enough to. I suppose, if he's not that good looking I
can just end the call, uninstall discord and never visit the forum ever
again!

`Okay, I think we can do that.' It's worth the risk. If he's hot this'll be
pretty awesome.

Within seconds, Discord is asking for my permission to start a video
call. Accepting, the screen is suddenly filled with a guy in a bedroom. The
risks paid off. Short, dirty blond hair, blue eyes and a cute smile greets
me as the feed comes into focus.

"Hey, I see you've started the party without me!" His voice is pretty cute
as well. Slightly camp, but nice to listen to with his American accent.

"Heh, yeah, didn't see much point of putting clothes on after getting
cleaned up." I can feel a slight blush appear on my cheeks. While I'm
naked, I can see Boston's not.

"Not complaining, you're super hot!" I'm sure the blush is getting
deeper. I'm really not used to people complimenting me on my looks. I move
my left hand to rest on my shoulder, shyly hiding a bit of my nudity as
nervousness starts to replace horniness.

"Uh, thanks dude. You're pretty cute." In my embarrassment, I almost forget
to compliment him back. Though, it's a pretty lame one.

"Thanks, can see by your body you actually do play soccer," He's being too
complimentary. My whole body is going to turn red in a moment, "Plus that
sexy British accent!"

"Heh, I wouldn't call the British accent sexy." Always confuses me when
people say that. Have they ever heard the scouse accent? So very not sexy.

"Well, my dick disagrees with you." He winks at me through the camera as
his right-hand goes out of frame; probably to feel his dick.

"And we all know you can't argue with a dick." I give a wide smile to the
camera.

"Hot and funny! Really glad I replied to your thread now!" Me too! This
could be fun. "I'm Troy by the way." Didn't expect he'd want to exchange
names. Though, I guess we can't call each other BostonNoSocks and Footylad.

"Tim. Nice to meet you. And thanks for helping me out." In my nervousness,
I'm being a bit overly polite.

"No worries, not like I'm not getting something out of it as well," Troy
gives a wink to the camera, "I'd best catch up to you. Can't do this in
clothes!" Standing up, Troy takes off his red t-shirt, revealing a decent
body. Slim, with the hint of muscle underneath. All natural-looking, no
sign of having done much exercise. Still, pretty hot though.

Removing his white shorts, his hard dick bobs about before he sits back
down on his chair, moving it back slightly, allowing me to see him slowly
wanking his circumcised cock. It's hard to tell from the image, but I'd
guess he's between 6.5 and 7 inches long, but pretty thick shaft, the head
being thinner. Kind of like the opposite of Lee.

"First thing you'll need is some lube." Troy reaches out of the screen,
returning with a small bottle, of what I assume is lube.

"Heh, well you're good and prepared, unfortunately, I'm going to have to go
find something." Getting up, I head to the bathroom.

Searching the cabinet, the only thing remotely useful is a tub of
Vaseline. I've no idea what it's actually for, all I know is we always have
some. I'm sure it'll be good enough.

Returning to my room, Troy's still on my laptop screen, still slowly
wanking, though his dick looks a little shinier than before.

"Only got this," I wave the Vaseline up to the camera, "hopefully do the
trick."

"Heh, that should be fine. You really haven't done anything anal, have
you?" Troy gives a lopsided smirk. I must look like a completely clueless
fool.

"Naw, only had my first blow job yesterday." Maybe if he knows how much of
a virgin I am he'll take pity on me.

"Wow, really? Someone hot as you?" I slightly squirm in my chair from his
compliment, "you mind if I ask how old you are?" Do I go with what's on my
profile? Would he have even read it? To be honest, I doubt he'll snake on
me if he knows I was a member at the age of 16.

"18." I go with honesty.

"Nice. I'm sure you'll be getting a shit load of action soon." Maybe if I
like anal I can get some action on Friday. Maybe I should get some condoms
just in case.

"Thanks." Even with my shy, nervousness, watching Troy playing with his
cock has my own dick fully hard.

"Okay, so watch what I do first and then copy me, okay?" Troy gets the lube
bottle again. Standing up, Troy's head goes out of view as he puts a dollop
of lube in his right index finger. I can't help notice his pubes are pretty
much buzz shaved back. Not completely smooth, he still has a slight
stubble.

Turning around, I get a clear view of his ass. Pretty nice. Looks soft and
very squeezable. Kneeling on his chair, he pushes his butt out towards the
camera, slightly opening up his cheeks. From the distance his crack looks
hairless like the rest of him, however, the quality isn't exactly 4K, so
I'm not able to make out any great detail.

Reaching back with his left hand, he pulls his left cheek open, giving me a
view of his pink hole; still no hints of any hair. Unable to ignore my
throbbing cock any longer, I grab it with my right hand and start
wanking. The hotness on the screen is too much for my horniness.

I swear I see his hole puff out as his lubed finger comes in from the
right. Circling his pink ring a couple of times, making it shiny, he slowly
inserts the finger in as far as he can. I can just about hear Troy give out
a moan as he starts a slow, smooth fucking motion. My own hand if flying on
my cock as I lean in closer to my laptop, trying to take in as much as I
can.

After about two minutes of playing with his hole, Troy takes his finger out
and turns back around, sitting properly on his chair. His right hand
immediately goes back to his still hard cock, wanking it faster than he was
before.

"You enjoy the demonstration?" Despite not being able to see below my
waist, it's probably obvious what I'm doing.

"Oh yeah! Very hot dude!" Watching porn never gets me this horny. I suppose
it's more personal. This guy's fingering himself for me and no one else. I
stop wanking to push my chair back and stand up, showing Troy how much I
was enjoying it.

"Fuck! You're huge!" I'm not that big! About 8 inches? Okay, I've
measured. It's 8 inches. Though, I am bigger than all the other guy's cocks
I've seen. Maybe I am big. Has too much porn warped my sense of dick size?

I can see Troy's picked up speed on his dick as I uncap the Vaseline
bottle. Sticking my right index finger in, I get a goop of the greasy gel
before kneeling on my chair, ass facing my laptop and Troy. Pushing my ass
out as he'd shown me, I feel my cheeks parting. Reaching back with my left
hand I can feel my hole without any need to hold my cheeks. Maybe I'm meant
to bottom if my ass opens up so easily. If my hole spreads as easily it
might just be a sign!

Laying my head on the back of my chair, I rest the palm of my right hand on
the small of my back, copying Troy, I start by circling my hole. The usual,
pleasurable shiver goes through me as I rub the wrinkled skin. Am I really
going to finger myself for the first time, with a stranger watching me over
the internet?

"Push out your hole like you did with the straw. Your finger should just
sink inside." Taking Troy's advice, I do as he says.

The moment I pushed out the muscle, the tip of my finger slides in past the
ring and into my hole. Stopping for a moment, I flex my ring, seeing how it
feels. At the moment it just feels like something's in my hole. Not
painful, not pleasurable, just ... a pressure I guess.

There being no pain, I push on, slowly inserting my finger until I have it
fully inside me. Still no pain or any great pleasure, just feeling a bit
full. Maybe I'm not a natural bottom after all. Though, I seem to be able
to take it well enough. Maybe I'll just let guys I'm really into fuck
me. Thinking about fucking, I start to withdraw my finger, stopping with
the tip in the entrance before sliding it back in.

With the added motion, it's starting to feel good. Not like
earth-shatteringly good, just giving me nice tingles through my
body. Especially when my finger's sliding back in. Picking up a bit of
speed, I can't help but give a small moan as the sensation from my hole
connects to my balls. Okay, maybe I can bottom. Definitely give it a go
anyways. See how it feels to have a cock fucking me and not just a finger.

After about a minute, my finger starts to ache. Pulling out, I turn back
around, sitting facing my laptop. While fingering myself had felt good, my
dick had gone down a bit, however, it quickly hardens back up when I looked
at Troy. With his legs out, stretched past his laptop, right hand's
furiously wanking his cock, while two fingers of his left hand fuck his
hole.

"How'd you enjoy fingering yourself for the first time?" Troy has a big
grin on his face.

"Wasn't bad, felt pretty nice. Curious to see what a cock feels like now!"
Pushing back my chair, I make sure Troy can see me wanking my own cock.

"Heh, glad I could help you discover the joys of your ass," putting my feet
up on my desk, I mirror Troys position, "shame I can't be there to help you
discover some more." Putting my left hand underneath my balls, I slide my
middle finger into my hole. It easily slides in, my ring still being lubed
from the Vaseline. "God, I'd love to feel your big cock fucking me right
now! Have you pound me till you cum inside me!"

Wanking my cock with the added sensation of fingering my hole is making
this the best wank I've ever had. With the added stimulation of watching
Troy doing the exact same and talking dirty, I'm getting super close, super
fast!

"Then while your cum's still drying inside me, I flip you over and fuck
your hole until you cum a second load!" Holy fuck, Troy's a dirty
bitch. All I can do is moan in return as my body tingles all over, my legs
shake uncontrollably and I feel my balls pull away from my left hand,
towards the base of my cock. "Once I shoot deep in your hole, I sit on your
face and make you eat your own cum as I suck you off to another load, deep
in my throat!"

"I'm cumming, I'm cumming, Troy, I'm cumming!" With all the pleasure my
body starts humping as my first two shots fall into my treasure trail, then
a massive wave of pleasure hits as my third, fourth and fifth shots all
clear my head or shoulder; the thin trails lining my body and face. My
sixth shot hits between my pecs before my cock simply quivers and shakes
out more pleasure, but no cum.

Troy's heavy breathing and moaning brings me back to my laptop screen just
in time to see him give out eight-strong shots; hitting between his pecs
and abs, the angle of the camera stops me from seeing more, however, once
Troy catches his breath, removes his finger from his hole and straightens
up, I can tell his cock shot even more; his stomach and pubes being covered
in his cum.

My chest going a million miles a second, I'm unable to speak or really do
much else but pant.

"Fuck, me, man! We both made one helluva mess!" I just smile, still not
able to do anything more. "Hey, was good caming with, but I'd best have a
shower before work!" Pulling my finger out of my own ass, I put my feet
back to the floor.

"Yeah, uh, thanks for everything. Really made my first time a memorable
one!" Just a shame he's on the other side of the Atlantic Ocean.

"I'm glad to be of service. Just need to get me a ticket to England!" I
can't help but laugh as my body completely relaxes, satisfied.

"Well, if you're ever in the area let me know." Chances of actually ever
meeting him? Zero. However, it's nice to dream.

"You can bet on it! If you need any more advice, just hit me up. Have a
good day, Tim." With that, the video disappears and I'm left, sitting,
alone, naked, covered in cum.

If you've enjoyed feel free to drop me a message at:
bootusrim@gmail.com. Also check out my other stories:

https://www.nifty.org/nifty/gay/adult-youth/the-morality-of-cheating

https://www.nifty.org/nifty/gay/encounters/i-aint-gay/