Date: Sat, 02 Jul 2022 05:34:16 +0000
From: Lizard69 <69lizard69@pm.me>
Subject: Wingman by Lizard69

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Wingman (adult youth, cross dress)
Lizard69


	We were on the patio.  Looking over the back yard as I paid Sam off
for the week, I couldn't help thinking it was one of the better deals I had
made.  He'd started out as, "the kid that mows the lawn".  That was more
than a year ago.  Now, if I had any reason to talk about him he was my,
"groundskeeper", and I was most likely plugging him to somebody looking for
one.  Not far into his teens, he was already thinking about hiring other
kids to do the simpler stuff so he could get some of his free time back.

	"Uh, Mr. Scott?"

	"Yes?"

	"I'm not trying to be nosy.  I won't feel bad if you tell me it's
none of my business, but you're always at home, usually sitting in front of
a computer.  What kind of job do you have?"

	"Jobs, actually, when you work free lance it's rare to have one
sort of gig that pays enough to cover the gaps between jobs.  My fall back
is copy editor, mostly for advertising, but now and then a literary agent I
know will ask me to massage a pile of dreck into something he can actually
promote without puking.  Back when I got downsized the company hit me with
a decent buyout so I do a little investment management.  Sometimes I'll be
sort of a free lance broker, hooking up people who want to buy something
really hard to find with others who have something to sell.  That one is
the most fun but it doesn't happen often enough to make a living that way."

	"So you don't have to go out and work in an office somewhere?
That's really chill."

	"Sometimes.  You see that workstation in the corner of my living
room?  Sometimes it's like my job moved into my home and I have to wrestle
with it to make it leave me alone long enough to have a life.  That's just
the way it is.  All you can do is try to make the good times longer and
keep the bad times short."

	A few weeks later he had finished the spring clean up and school
was letting out just in time for his heavy work season.  He was hanging
back instead of doing the normal kid thing where you take your pay and run.

	"Is there something on your mind?"

	"Uh, Mr. Scott..."

	"Joe.  If you're off the clock and not discussing work there's no
need to be formal."

	"Ok, Joe.  You spend so much time working online, do you ever get
into, like, online chats?"

	"Some work related stuff, I prefer email because it lets me fit it
into breaks in other work instead of dropping everything else to go one on
one.  I'm not overly social but when I hang out I'd rather do it in person.
You have something going?"

	Sam started to blush.  Life sucks a little bit when you're a
redheaded kid who hasn't had enough summer to start building up a tan.  My
own hair had darkened with age but I still remembered those days.  It
didn't help that he had that other thing going.  There aren't a lot of
redheads that fall near the physical average.  They tend to be either
chunky couch lumps or like Sam.  I knew the kid worked harder than just
about anyone close to his size but he was more "whipcord and rawhide" than
the usual idea of muscular.

	"Sort of?  maybe?  I was in this online group where some of us hang
out and a guy invited me into a private chat.  I didn't even realize it was
a guy at first.  He had one of those chat handles that could go either way.
I don't know why, but when he asked if Sam was short for Samantha I played
along.  Maybe I was thinking that I could get to know a girl without her
automatically thinking I wanted to get her pants off."

	"You like girls?"

	"Yeah, but they get scared if I'm, like, tripping over my dick."

	"Man, do I ever know what that's like!  Half the time it seems like
they only want you to be interested so they can put you down for being
interested.  The good news is once you start getting laid fairly often you
can flip it the other way.  Most girls are a lot more eager to get their
pants off if they think it's the best way to keep you from fucking their
friends instead.  Like nobody wants you until somebody wants you, then
everybody wants you."

	"For real?"

	"Real.  So how did this guy take it when he found out?"

	"Uh..."

	"You haven't told him yet.  So, you're getting into kind of a role
play thing?"

	"Creepy, huh?"

	"Maybe.  It's not that unusual.  I mean it happens so often that
nobody believes people in online chats really are whatever they say they
are.  It's kind of a running joke that 97% of all twelve year old girls
doing online chat are really thirty year old creeps in a sweat stained wife
beater living in their moms basement."

	"The other 3% are really girls?"

	"No, they're cops pretending to be girls so the creeps will come
out and get busted."

	"I guess I should stop."

	"I don't know.  Any time *I* say something that starts with, 'I
guess I should...' I usually end up doing the exact opposite.  Right now
you're just clowning around online, having some fun, not hurting anybody.
Personally I wouldn't waste a lot of time worrying about it."

	Next payday I just had to ask.  "How's it going?"

	I have to give the kid credit.  Even though it was plain that he
wasn't comfortable with the topic he didn't try to pretend that he didn't
know what I was asking about.

	"He started asking me to send pictures.  My sister is always
sending selfies to everybody.  Maybe I can swipe a couple off her phone or
FB page."

	"Uh-uh, not good.  There's always the chance he'll see her
somewhere and go after her thinking she's you.  I might be able to help you
out.  There's cold soda in the fridge.  Grab a seat in the kitchen while I
make a phone call."

	I got lucky. The woman I called had some free time and thought it
might be fun.  That left me pitching the idea to Sam.

	"A girl I used to date is part of a local theater group.  The group
isn't very big and they often don't have the right ages and genders for the
plays they want to do.  It's nothing creepy.  Actors are always getting
made up to look younger or older, even turned into aliens.  Changing a girl
into a boy or the other way around is no big deal.  I invited her to come
over and see what she could do for you.  I won't be ticked off if you want
to bail.  We'll just forget you ever said anything about it.  I'm kind of
curious though to see what she can do."

	"You told her?  About the chats?"

	"Nah, I told her you were invited to a costume party and we were
just playing around with different ideas."

	"Uh, thanks.  I guess it isn't going to hurt to find out.  It
doesn't sound like she would give me a hard time about it."

	Liz sat down across one corner of the table from Sam.  It was still
early enough there was plenty of light coming in through the patio doors.
She lifted his chin, turned his head to a couple different angles, then
shot me a confident smile.

	"Next time try to find something challenging.  I didn't bring a
costume and if you have any girl clothes that might fit him laying around I
don't want to know about it.  Something loose and sloppy is almost as good.
See if you can dig up one of your white dress shirts and a tie, something
with a lot of brown to match his eyes."

	She had a brush and blow dryer out of the makeup case and was
telling him to soak his hair down at the kitchen sink before I got anywhere
near my closet.  She folded the cuffs back half way up his forearms, left
the shirt buttons mostly undone and knotted the tie in a open loop.  I
pulled out my phone and took a few pictures before asking what she'd done.

	"Not much of anything really.  His hair isn't very long but some
girls wear it shorter.  He's got great natural curl and I know women who
would kill for hair so easy to style.  If they're going to make a hobby out
of doing chemical warfare on their scalp that's their own tough luck.  I
hit him with a little lip gloss and a pair of plain lens glasses so I
wouldn't have to mess with his eyes.  His natural blush looks better than
anything I could do with makeup.  What do you think?"

	"He looks like a tomboy caught playing dress up in dads room."

	"Uh-huh, put him in a blouse and skirt and he could be a
secretary's daughter on take your kid to work day.  Make the blouse white,
use a tie that matches the skirt and he's a serious student at a private
girls school.  Put him back in grubby jeans and a tee and he's your yard
crew again."

	"Let me know when you're free.  I owe you lunch at least."

	"Don't worry about it but I might be back to twist your arm, or
his, the next time we're short a couple of bodies that don't need any
acting skills."

	I sent the photos to Sam's phone and forgot about it until a week
and a half later.  Suddenly Sam is at my patio doors.  It's not his usual
work day and he's in such a total panic he wouldn't have been able to do
anything useful anyway.

	"Mr. Scott? I don't know if you can help me.  If you can't I don't
know who else to ask.  He's going to tell!"

	"Slow down.  Who's going to tell?  Tell what?  Tell who?"

	"The chat guy, he's gonna tell everybody everything!"

	"Ohhh-kay the light begins to shine.  You sent him more photos?"

	"Sis went shopping with mom at the mall a couple towns over.  I
knew she'd be gone most of the day so I got into her closet, borrowed a
blouse and skirt.  Uh it didn't look right with boxers."

	"So you went commando?"

	He stood there staring at the carpet, blushing like a beet, and
shook his head.

	"You dug out a pair of panties too."

	I stuck out a hand.  He backed away like I was trying to tear off
his 'nads.

	"I can't help much with damage control if I don't know how bad it
is.  Give me your phone.  Unlocked.  It will speed things up if you open
the chat where things started going wrong."

	I automatically backed it up a couple pages figuring we'd have
different ideas of where it went wrong.  I was right.

	"Ok, he's aware you're not actually a girl.  He's also not going to
let minor details get in the way of fucking you.  You know, little things
like you being under age or having better things to do with your time.
Right now he's pushing for more pics or a cam show but you can be pretty
sure that if you follow the program it'll get physical sooner or later."

	"Oh my God!  What am I gonna do?  I'll fuckin' DIE if everybody
sees those pics."

	"You just did the most important things.  When you find out you're
in a hole, stop digging.  When you don't know what to do, get help.  I've
got more respect for you now than I did a week ago and I already thought
pretty highly of you then."

	"But... The selfies?"

	"What about them?  I saw a couple that might qualify as soft core,
only one where the end of your hardon was poking up past the waistband.  If
the whole load went public we could say Liz and I talked with you about
getting involved in her theater group.  You started clowning around and got
a little carried away.  I'm sure Liz would back me up."

	"He's still got the chat log."

	"Who cares?  Give me five minutes with a text editor and I can
dummy up any conversation you want.  I'm sure that's what his lawyer would
be saying if the cops were questioning him right now."

	"But..."

	"From what I can see he never actually came out with an 'or else'.
You want to make sure you're in the clear?  Send him another text.  Tell
him chat's over.  If he wants to meet up you'll think about it but you're
not going to get anywhere near the kind of jerk who would try to blackmail
a kid.  I'd say the odds are around sixty forty he either starts
apologizing all over himself or disappears, less than one in a hundred he
tries to make some trouble.  If he does I'll help you teach him about how
miserable his own life can get if he messes with the wrong people."

	A few days later everything seemed back to normal.

	"Chat's over?  No more selfies?"

	"No more selfies."

	I almost let it go at that.

	"But you're still chatting.  Let me guess.  He apologized for
making you uncomfortable.  He never wanted to push you into anything.  He's
not really queer and knows you aren't either.  You're just doing a role
play where he's a total horndog and you're maybe kinda thinking about it."

	"Er...  Uh..."

	"Let's get something clear, I'm not your mother.  I pay you to do
yard work.  You don't pay me to be a life coach.  Once upon a time, long,
long, ago, I was a teenage boy.  I'm not even sure how much I remember from
back then is real and how much is my own mind trying to put the best face
on something that was pretty awful at the time.  If you want a sympathetic
ear, I'll listen.  If you want somebody to watch your back while you get
stupid, I'll try to talk you out of it first, but I won't leave you
hanging."

	"You really mean that?  Like if he wanted to...  You wouldn't call
the cops?"

	"You think you're the only kid who's going to have his first time
with an old guy?  You think most of them get dragged off the street?
You're a good kid.  I don't want you to get hurt.  But I can't lock you in
a padded cell either.  Nobody can.  Legally, you're still a kid.  I've
heard some people make it to the age of consent before they have sex.  I've
never heard anyone claim that they waited that long because of the law.  I
can more or less make my own hours.  So...  Yeah...  if you need a wingman
let me know."

	Mid morning a few days later rain was pounding down while I was
trying to convince myself I really didn't want a second pot of coffee.  The
sound of the doorbell was almost drowned by thunder.  Fitting really,
standing outside my door was my almost drowned groundskeeper.  I left him
dripping in the kitchen, returning shortly with a huge towel and a small
shopping bag.

	"I don't give my employees birthday gifts.  Call it a delayed
Christmas bonus.  I was going to hold it in case you decided to drop the
idea.  But you need something to change into and I can't think of any other
reason you'd be out in this weather."

	The white blouse and charcoal skirt didn't surprise him but Sam
couldn't help blushing as he went deeper into the bag.

	"The outer stuff is from a thrift store but I washed it.  The black
scarf matches the stockings and garter belt.  The pants are what the girls
call boy shorts.  Don't put them on first if you think you'll be taking
them off.  Most girls look hotter if they're still wearing stockings when
they're ready to play.  The shoe size was a guess but they're pretty close
to open toe flats and the heel strap has a lot of take up.  You'd need
practice to go anywhere in heels without breaking your neck."

	I left him to dress while I threw his wet clothes in the dryer,
then tracked him by sound to the blow dryer in the bath.  Watching him
stand there in girls underwear working on his hair was... interesting.  I
didn't have to wait long before the silence was too much for him.

	"There's no way I'm doing any yard work in this weather.  I started
texting with...  He calls himself Bob.  I don't know if that's his real
name.  I don't really know if anything he told me is true.  He said he's
'around thirty'."

	"That means he's probably somewhere between 35 and 45.  Thirty is
kind of a break point for people.  If he was under it he's say 'almost' or
'getting close to'.  If he wants to meet you he has to keep it somewhere
close to real and most guys who stay in shape can pass for ten years
younger."

	"So, we're texting, then sexting, then he's asking me to meet him,
and it isn't really pressure..."

	"...but it's sort of getting down to, like, get busy or get lost?"

	He gestured to the phone laying next to the sink.  While there
wasn't much info about Bob himself, there wasn't any doubt about how he
expected his 'date' to go.

	"Ok, he wants to meet you at a mall around lunch time.  I can give
you a lift, no problem.  Let's say he shows up and you don't see anything
that's an instant deal breaker.  We'll sit down and I'll lay out some
ground rules and conditions.  If either of you can't handle that, I'm out.
He's not going to bend you over a planter in the middle of the mall, so
you're either leaving with me or we go with him.  That much is
non-negotiable."

	"Ok."

	"So, let's say neither of you thinks my terms are unreasonable.
Then what?  You want me to hang around in case you change your mind and
decide you really can't do that?  How close is 'around'?  If all you need
is a ride home I could be tipping a cold one six blocks away.  If you're
worried he might not pay attention when you say no, I'd almost have to be
in the same room to do anything useful soon enough to matter."

	"I... Uh... I guess I didn't think it through.  If you're going to
be life guard you have to be somewhere near the pool.  We need to get
rolling.  Dressing like a girl is weird enough.  I don't want to be late
because I spent too much time messing with my hair."

***

	"Are you mad at me?"

	The question startled and even embarrassed me a little.  I'd been
silent through most of the drive to the mall.  While it normally wouldn't
have been a problem, this time we weren't going to the nearest or even the
larger one most people used for a better selection.  Sam and Bob had agreed
on a town about that far in a different direction to cut down on the chance
of meeting anyone who knew them.

	"Not really, and that kind of bothers me.  I should be mad at you.
What you're doing is kind of creepy and not too bright but it's your
choice.  If I try to talk you out of it you'll probably agree then sneak
out and do it anyway.  The best I can do is watch your back.  Honestly, I
should be mad at you for putting me in that position."

	"If you're not mad..."

	"It's a whole bunch of things but swirling around in there with
everything else I'm just a little bit jealous.  Does that creep you out?"

	"You want to...?"

	"For me it's always been like one of the old jokes.  When sex is
good it's really great and when it's not great, it's still pretty good.
I've never been with a boy.  Never seriously thought about it.  Now I'm
helping you set it up and can't avoid thinking about what he'll be doing."

	"I'm sorry."

	"Don't worry about it.  It's not important.  Looks like we're here.
Let's grab something so they won't kick us out of the food court and see
how long it takes him to show."

	For his first time in public dressed as a girl Sam handled it well.
At least to a casual acquaintance. It helped that he had more of a tomboy
look going.  The girls acted like he was invisible while the few guys that
noticed him picked up kind of an anti-flirt vibe.  We hardly had a chance
to grab a shake and sit down before he got a text.

	"Who's the guy?"

	"A friend.  He's ok.  Where are you?"

	Instead of an answer we got Bob dropping into a vacant chair.  He
was what I expected only because I had no expectations.  A guy, probably
under forty but I wouldn't have bet my lunch money.  Otherwise so average
you could pass a hundred of them on the street before you realized you were
seeing the same guy over and over.

	"Before this goes any further, I need to see some ID."

	"What?  Why?  Who are you?"

	"Call me Joe.  I guess you could say I'm Sam's responsible person.
An adult is presumed competent to manage his own problems.  A baby needs
somebody there 24/7.  A baby doesn't magically turn into an adult when
somebody throws a switch on the right birthday.  Most parents have enough
sense to back off and let the world slap their kid around until he learns
how to deal with it, while staying close enough to keep him alive.  Then
one day puberty hits.  All of a sudden he's getting into some adult level
shit where he'd rather crap broken beer bottles than get his parents
involved."

	"Ok, makes sense, but why the ID?"

	"Insurance.  You told Sam to call you Bob.  He's ok with that.  Sam
knows me well enough to ask me to cover his back, but to you I'm Joe.  If I
don't know who you are and where to find you I can't let Sam get into a
situation that might go sideways.  No hard feelings, just the way it is."

	He wasn't exactly thrilled but had sense enough to accept that it
wasn't negotiable.  It wouldn't have been a deal killer if he used a fake
name.  Still, my comfort level went up as I confirmed that he actually was
Robert somebody and a year short of his 40th birthday.  It went up some
more when he volunteered that he'd reserved a nearby condo via air-bnb.  An
audit trail if things got ugly but no desk clerk from the nearest no-tel
calling the cops over something suspicious.  Things didn't get awkward
again until we were standing in the living room watching Bob lock the front
door.  They both turned to me.

	"So, how are we going to do this?"

	"Hey, we're not playing 'Mother may I'.  I'm just here to make sure
Sam can leave anytime he wants to exercise that option.  One other thing,
both of you can leave your phones on the counter.  If you want photos, I'll
take them, but neither of you gets a copy of anything unless both of you
agree you should have it."

	Pulling out my own phone I started recording video.

	"This is just to cover my ass.  Sam?  How far you take it is up to
you but I need something to show that you know why you're here and nobody
is twisting your arm."

	I hadn't suggested anything specific.  All I knew for sure was that
I didn't want it to look like one of those hostage videos where the
terrified victim is obviously reading off of cue cards.  It turned out Sam
had his own ideas.  He smiled, turned towards Bob, and, well, flowed up
against him sounds so "romance novel".  He wasn't moving like some
experienced seductress.  It was more like a tomboy getting into her first
real make out session.  Zero experience but completely on board with
wherever it would take her.  Sam wrapped his arms around Bob's neck and
they kissed, not a sloppy, hungry, fuck me now thing but open mouth.  When
they came up for air it was Sam who said, "Play with me."

	I decided I'd keep recording until they took it into the bedroom,
then settle down and see if there was anything good on TV while they had
their fun.  Only they didn't.  Soon Bob had Sam's blouse unbuttoned and
panties shoved half way down his thighs.  Sam had somehow managed to get
Bob's whole package, balls and all, pulled out through his open fly.  As he
lifted the boys skirt and began kneading Sam's naked ass while lightly
bumping their hardons together I realized I was already past the point
where I should have stopped recording.  The thought of me standing there
catching all this on video was creepy and embarrassing afterwards.  At the
time though, I was watching them on the screen of my phone, which gave it
sort of a mental distance, along with the two of them giving each other so
much attention there didn't seem to be any left over for me.  I wasn't
directing the action.  It was more like being a Chinese stage hand.

	Sam decided it was time to move on to a more intimate kiss,
continuing to make eye contact while dropping to his knees.  Bob's cock
wasn't any longer than average and not very thick.  Maybe it's my
imagination but Sam looked disappointed that he couldn't get more of it in
his mouth without gagging.

	"I won't get upset if you cum in my mouth, but I thought you wanted
me all the way."

	"Can you do that?"

	"I've only tried it with my fingers but if you go slow and don't do
it too long I think we can."

	I followed Bob leading, almost dragging Sam into the kitchen.
Rummaging in the cupboards he found a tub of vegetable grease, Crisco or
something like it.  Bob pulled out one of the chairs, moving it to the
side, and had Sam bend over, grabbing the edge of the table.  He'd lost his
panties on the way and had no trouble spreading his stockinged legs.  Bob
spotted them on the floor as he was getting Sam slippery and open.  Picking
them up, he turned to wedge the head of his dick firmly against Sam's hole
then reached around, resting his forearm against the back of the chair with
the boys hardon in a wad of loosely crumpled panties.

	"There's too much chance I'll hurt you if I do it.  I'm going to
hold still and let you push your ass onto me as you hump my hand.  I'll
wear a condom if you want, but as far as I know I'm clean and I'm sure that
I'll cum faster without a cover.  I want to drive it into you like a wild
bull but it's safer for you to set the pace and decide how much you can
take."

	For a while it didn't seem like anything was happening.  Then I
noticed the way his thighs trembled while he slowly increased the backwards
push until Bob's cock could open him up enough to slip inside.  Bob was
hardly in past the head when Sam, well, he didn't so much pull back as
reverse the pressure before pushing again.  Before long Sam started rocking
his hips in a way that let him get a longer stroke into Bobs hand without
moving his ass that much.  There weren't any porn star vocals.  Bob was
panting and gasping.  Sam was starting to let out low whimpers and moans
that tried to lift the hair on the back of my neck.  It was the kind of
sounds that could have been pain or pleasure but were probably a weird
blend of both.

	They picked up a little speed but still weren't very fast or deep
when Sam sort of yelped as his hips made several short, sharp, jerks while
he shot his load.  Bob pushed him forward onto the table as his arms gave
out, then pulled back until just the head of his cock was trapped by the
tight ring of Sam's asshole.  Instead of battering a kid too far gone to
object, he reached down between them and finished by hand, leaving his hot
load inside the boy.  Without a word he left for the bathroom, I guess to
clean up.  Almost as an afterthought I finally quit recording.

	"Are you all right?"

	"I...  I need to leave, right now."

	"Ok.  Do what you can to pull yourself together while I let Bob
know.  He might panic if we just run out."

	As expected, I found him in the bathroom.

	"Sam isn't coping very well and needs to leave.  No hard feelings.
It's all just a little overwhelming.  This is only a suggestion, but it
might be better if you wait for him to call before you try to contact him.
At least give him a couple weeks to sort things out for himself."

	"Uh, sounds like a plan, thanks."

	Sam was dressed and ready to leave when I got back to the front
door.  A few minutes later we were rolling towards the edge of town.

	"I think I'm gonna be sick."

	I pulled over just in case, but his stomach settled a little.

	"Try not to hate me."

	"Why would I hate you?"

	"You gotta think I'm some kind of crazy freak!"

	He was sitting there, looking a little rumpled, kind of hunched in
on himself, and about as miserable as a human being can get.  He flinched
as I slipped an arm around his shoulders then relaxed, or maybe just went
limp.

	"Everybody has a first time.  For a lot of boys it's a girl not
much more experienced than they are, laying there like a starfish on the
beach while they get their dick wet.  For some it's force or blackmail to
do things they don't want, with somebody they don't like.  No matter how
much you want it, the first time is a little like rape.  It can't be
anything else.  There is no way you can give informed consent to something
you've never done.  You don't know what you're consenting to."

	"I knew."

	"You knew about it.  You intended to let him do things to you.  Now
you know what it's like to cum while a man is fucking you."

	"Oh God!  I feel like such a perv."

	"Welcome to the club.  All men are pervs, most women too.  Some are
nicer about it than others.  Some do a better job of hiding it.  Right now
I'm feeling really creepy about recording your first time, but not quite
creepy enough to delete it and try to forget I was there.  What about you?"

	"What about me?"

	"When we get back to my place, you can get out of the girl clothes,
clean up, and go back to doing yard work and jerking off like any other
adolescent boy.  Today can be that wild thing you tried once, just to find
out what it was like.  Or..."

	"Or what?"

	"Or you can leave the girl stuff at my place, so your mom won't
blow a fuse if she finds it in your closet.  You can set something up with
Bob again, or find somebody closer.  Best would be some middle aged
straight guy who cares about his reputation enough to keep your secret, but
gets so damn horny sometimes he doesn't care if he's fucking a boy."

	While I was talking, my free hand was sliding up his thigh.  Don't
ask me why.  I wasn't thinking about it.  It's like the thing had a life of
its own.  Past the top of his stocking, over skin as smooth and soft as any
girl, until...

	"What the hell?!  You put them back on?  Soaked with your own cum?"

	"Yeah, it's... really nasty, but I didn't have anything else so it
was that or go bare assed.  But you know what?  In some weird way it feels
right.  Like, letting him do that to me was so messed up, I *should* be
sitting in a sticky mess when he's done with me.  I, uh... I hope it isn't
soaking through the skirt.  I don't want to mess up your car seat."

	My fingers had traveled a little higher.

	"You're hard again.  Is it... from remembering what happened, or,
well, thinking about the next time?"

	Sam didn't answer, unless you count the way he blushed.  I quit
molesting him long enough to start the car and got back out in traffic.

	"You must think I'm the worlds creepiest pervo."

	"A straight kid who lets himself get raped by an older, straight,
man?  Then after the guy uses you for a cunt substitute, you decide that
isn't degrading enough and leave with your freshly fucked ass wrapped in a
cum soaked catch rag?  Yeah, I'd say that's about as perverted as it gets.
So what?  Am I supposed to cry or cheer?  If your parents knew they'd
probably lock you in a closet and slide pizza under the door until you're
old enough to throw out of the house."

	"Oh my God!  You can't tell them!  Please?!  I...  I'll do
anything."

	"You probably will, and the fact that I'm getting hard right now
says something about me I would have been happier not knowing.  I can't
un-see it, or scrub my eyeballs and pretend I wasn't there.  Even if I
could, I wouldn't.  I *LIKED* it, watching him turn you out, getting you to
cooperate, to participate in what he was doing to you.  If that means I'm a
creep too, I guess I'll have to get used to it."

	For quite a while neither of us had anything to say.  I was
watching the road while Sam did the same or checked out passing scenery.
Eventually, I felt fingers on my wrist and allowed him to guide my hand
back to his thigh.  Once again I was caught by the contrast.  His hand
matched his slender, almost girlish frame, while the palm was callused from
all the yard work he did.  Soon his fingertips were touching, teasing, the
back of my hand on his leg while my own were doing the same to his inner
thigh.  At my place, I snatched an item off a garage storage shelf then
followed him through a door into the kitchen.  He stopped when I touched
his shoulder, allowing me to turn him and lift his chin until we were
making eye contact.  Sam jumped a little when the thick rubber kneeling pad
made a loud "thwock" as I dropped it.  He normally used it pulling weeds or
working in the flower beds.  It was going to work just as well keeping his
knees off the kitchen linoleum.

	"I would never use the video from today to blackmail you into doing
things.  You can't know that.  You can believe it, but there isn't any way
for you to look inside my head and know it's true.  It works the other way
too.  As long as I have that video I can't do anything with you and be
completely sure it's ok, that you aren't feeling pressured.  I don't want
to delete it.  It's just about the hottest thing I've ever seen."

	I pulled up an encryption app I used quite a bit and set it up to
save the video as a compressed, locked, file before handing him the phone.

	"Pick a key, some string of words that means something special to
you and then some numbers.  It could be a date, a locker combination, a
friends phone number, whatever."

	As soon as that was done I sent it to a digital lockbox I have.

	"So, now I have the only copy but you have the key that is the only
way anybody can watch it.  Nobody sees it unless we both think they're ok.
If you decide to let me have you I can be sure that you're not afraid I
might show somebody the video if I'm not happy.  Is that what you want?  To
let me have you?"

	"You mean like...?  My poor ass is going to be totally wrecked."

	"Letting me use the playground doesn't mean it's ok to break the
toys.  Lose the blouse and skirt.  Keep the pants on for now."

	If you've ever been someplace "clothing optional" you know that
skin is just skin, not especially sexy.  If I walked in on Sam showering at
the gym he'd be just another body in the room.  A couple ounces of sheer
nylon and lace changed that completely.  Knowing he just had his first
experience with a man and was, uh, up for more sealed the deal.  This
wasn't some hot young girl in front of me but my dick sure as hell wasn't
thinking "yard crew".

	"Kneel down and start giving my cock some lip love.  You told Bob
it was ok to cum in your mouth.  That's a good place to start.  Only, when
I blow my load, don't swallow, just let it ooze out around my dick and
dribble off your chin.  You can use one hand to jerk me while you're
sucking.  Use the other to massage your own dick through that sticky catch
rag you're wearing.  Take it slow.  If you pop your load before you get me
off I'm going to finish in your ass.  I might anyway.  The idea of stale
grease and spunk seeping out around my cock while I fuck you is so nasty
it's a weird sort of hot."

	He must have already been close enough that it was a serious
threat.  Sam started frantically jerking me with his lips wrapped around
the head.  I guess I was pretty close as well.  It brought the expected
results sooner than I would have liked.  He looked up at me as if he was
worried that maybe he hadn't done it right.  What else could I do but help
him to his feet, wrap my arms around him, and give him a deep wet kiss?

	"Almost done, slip one hand in the back of your panties and use a
fingertip to play with your asshole.  You don't have to fuck yourself if
it's too sore.  I want you to get used to having something going on back
there any time you cum.  Keep the other on your cock.  Don't get it out.  I
want you to cum in your panties and squeeze the juice through the fabric
until it's trickling down your thigh."

	Honestly, I think it took less time to do it than say it.  He kind
of slumped as he finished, might have fallen if I wasn't holding him up.

	"You're my mine now?"

	"Yes."

	"Willing to fuck, anywhere, anytime, any way I want you?"

	"Oh God, YES!  Just promise you won't tell anyone."

	"No.  You won't tell anyone.  Letting me have you completely
includes letting me decide who knows about it.  I felt Sam shiver slightly
before he nodded, silently agreeing to my terms."

	The rain had stopped and while I stood there holding him the sun
started breaking through the clouds, sending shafts of light into the fresh
scrubbed greenery of my backyard.  I don't believe in omens, but few
moments of my life have ever seemed so loaded with possibilities.

The End?