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Down In A Hole
by Dim (dimitri69@fastmail.fm)

***

A mostly-true story. The details have been exaggerated 
(this story is much more extreme than the real events), 
and the names and parties involved have been changed. 
But the basic story elements are true. A party LIKE 
this really happened, and I really was subjected to 
treatment SIMILAR to this. I've merely taken a bit of 
artistic license. (F+/M, nc, v, tor, mast, bd)

***

As parties go it really didn't seem that outrageous. My 
wife was out of town on a business trip and her sister 
Wendy had invited me to a party with some of her 
friends and co-workers. I'm not much of a "party 
animal", but Wendy has always seemed pretty innocent 
and harmless, so I figured this party wouldn't be that 
big of a deal anyways. And at first I thought I'd been 
right. It was basically a bunch of young men and women, 
most of them teachers at the local high school, sitting 
around chatting and drinking. 

I'm not really sure when it all turned on me, but 
looking back it's easy to imagine that everyone there 
had been paying particular attention to me from the 
moment I walked in. I kept catching people watching me 
out of the corner of my eye, but when I'd turn to look 
at them they'd go back to talking to someone else. I 
can remember thinking once or twice that there were 
some hushed conversations going on, conversations that 
would quickly end or be redirected whenever I'd walk 
over to introduce myself. 

And of course there was the alcohol. There's always 
alcohol, right? It seemed I was never allowed to have 
an empty glass or beer bottle. Some "thoughtful" person 
would always top me off or bring me a new beer without 
me even having to ask. And so it was inevitable that I 
got a bit of a buzz on.

At some point a game of Truth or Dare apparently 
materialized out of nowhere. One minute it was just a 
casual get together, and the next there was a room full 
of hot young women (and a few boyfriends) laughing and 
giggling and talking about sex and fantasies and 
embarrassing moments. Wendy, my normally shy and 
unassuming sister-in-law was among them, and eventually 
she convinced me to join in.

Most everyone there were friends already, and so I was 
sort of the new kid on the block. Naturally that meant 
the game began to focus on me. I answered truth after 
truth, describing my first sexual experience, 
confessing the last time I'd masturbated, hinting at 
some of my more forbidden fantasies. That lead one of 
the girls there to confess that SHE had always 
fantasized about glory holes. 

Wendy asked what that was and Meghan, the woman who 
owned the home we were in explained that a glory hole 
lets a man put his cock through a hole in a wall and 
get hand jobs and blow jobs from women without knowing 
who it is. Wendy was intrigued, as were several other 
women there. So the truth portion of the Truth or Dare 
game then focused on who in the room would seriously 
consider doing something like that. Given how young and 
hot (and drunk) everyone was by that point it's not 
surprising that pretty much everyone, myself included, 
admitted that we would.

It's a bit fuzzy after that. I remember having a few 
more drinks. I remember Wendy taking a couple of dares 
that lead to her getting partially naked and kissing 
another woman. And I remember her coming over and 
encouraging ME to take a dare. I was expecting 
something involving stripping or making out with 
someone, hopefully my nearly nude and extremely sexy 
sister-in-law. So with that in mind I agreed and on my 
next turn, when Wendy asked me, "Truth or dare", I 
answered... dare.

There was a little cheer and some clapping around the 
room, and Wendy took me by the hand and lead me down 
some stairs into the finished basement of the house. 
She took me into a dimly lit room and the first thing I 
noticed was another man, a boyfriend of one of the 
other teachers at the party I'd met earlier in the 
evening, stepping away from the far wall. He was naked 
and his cock was hard and wet. He was flushed and out 
of breath, and I finally noticed that the wall he'd 
just stepped back from had a fist-sized hole right at 
crotch level. 

Without saying a word, Wendy lead me over to the wall 
and began to undress me. I can't quite remember what my 
reaction was at that point, it's all sort of a blur. 
The man dressed and left and Wendy managed to get me 
completely naked, apparently without me putting up too 
much resistance. She stood next to me then and looked 
at me.

"Can you guess what your dare is yet," she asked with a 
smile.

As I stepped up to the wall and put my quickly-
hardening cock through the hole presented to me, Wendy 
immediately stepped up behind me and guided my hands up 
to two cuffs mounted at about shoulder height. 

I imagine the thrill of the situation, and the 
loosening affect of the alcohol kept me from 
questioning too much at that point. I simply stood 
still as my beautiful and "innocent" little sister-in-
law secured my wrists into the leather cuffs. Then she 
moved up against me, her bra-covered breasts pressing 
into my back as she stood up on her tip-toes to breath 
into my ear.

"I dare you to stay here and enjoy the rest of the 
night." She kissed my cheek and left the room.

I stood there for some time before I felt the first 
touch on my cock. I jumped at the unexpected contact, 
but my cock quickly grew completely rigid as the warm, 
delicate fingers of some unknown woman began stroking 
up and down it's length. Instantly I understood the 
turn on of the anonymity factor. Not knowing who was 
touching me allowed me to think back over the entire 
night and imagine that it was any one of the beautiful 
young women I'd seen, even Wendy herself. And when a 
second, and then a THIRD hand began touching and 
stroking and teasing me I began to fantasize that it 
could be ALL of the beautiful young women. 

The hands on my cock began jacking me off faster and 
faster. Whoever it was touching me clearly knew what 
they were doing, as my arousal grew faster than I would 
have thought possible. Within minutes I was ready to 
explode. But just before I came the hands pulled away 
and left my cock unfulfilled. 

I moaned in frustration and thrust my hips against the 
wall, pumping my cock in and out of the hole as much as 
I could, trying to continue the sensation. I thought I 
could barely make out some muffled voices and laughter 
from the other side of the wall, but no one touched me 
and my own efforts were useless. I stood there for 
several minutes as my near-orgasm faded and my erection 
began to relax.

And suddenly there was another touch, another feminine 
hand gripping me, stroking me. I grew completely hard 
again in an instant and thrust as far as possible into 
the hole, offering every inch of my cock to the 
ministrations of whichever gorgeous young stranger was 
now taking her turn. Whoever it was stroked me hard and 
fast for a minute or so before I felt the first warm, 
wet caress of a tongue across the head of my cock. 

I held my breath as the strange mouth completely 
engulfed me, lips stretching around the shaft and 
moving up and down it's length. I felt her tongue 
cradle the head, the rough roof of her mouth abrading 
it as she sucked me deep into her throat. Again I felt 
my orgasm build...

And again I was denied at the last possible second. The 
hand and mouth pulled away just as I was about to cum, 
leaving my cock bobbing in the cool air of the next 
room. I tried to picture what it must look like from 
their side of the wall. I imagined what my cock must 
look like protruding from a hole in the wall, wet and 
red and engorged, waiting desperately for release. 

It turned me on even more to realize that there were 
likely dozens of women waiting to take turns using and 
teasing my cock. And I realized how turned on I was by 
the idea that those women were in complete control of 
when (or even IF) I came tonight. They could touch and 
stroke and lick and suck as much or as little as they 
wanted, and there was nothing that guaranteed I would 
even be allowed to get off.

And so it went for quite some time. I'm not really 
sure, but I'd guess that I was brought to the edge of 
orgasm maybe fifteen times. By that point it was not 
only frustrating but actually almost painful. I was 
desperately thrusting my hips against the wall as hard 
as I could, frantically trying to get off every single 
time someone would touch me. I was pulling at the 
restraints on my wrists, hoping to free myself so I 
could at least get MYSELF off. And I was starting to 
yell at the women in the next room every time they'd 
tease me and pull away. 

At one point I tried a different tactic and tried to 
hold completely still. I hoped that I could mask how 
close I was to cumming long enough to keep whoever was 
sucking my cock this time to get me off without meaning 
to. But it was no use. Someone over there was clearly 
an expert at teasing, somehow knowing exactly the last 
possible second to pull away and leave me as close yet 
unsatisfied as possible time and time again.

Finally I heard the door behind me open and Wendy 
entered the room. She walked up behind me and ran her 
hands from my shoulders down my back to my ass. 

"You're moving too much, darling," she said, pushing my 
hips tight against the wall in front of me. Suddenly 
she reaches between my legs and I feel the cool, 
delicate fingers of my sexy, forbidden fantasy girl cup 
my balls and feed them gently through the hole and into 
the other room. She then quickly took another leather 
strap and fastened it to the wall and around my ass, 
binding me tightly in place and preventing me from 
moving or thrusting back and forth even the slightest 
bit.

Next she bound my ankles in place, securing them with 
cuffs identical to the ones at my wrists. And when she 
was satisfied that I was held completely immobile she 
stood up and fastened a ball gag into my mouth.

"There, that's better," she says. "Is that comfortable? 
I hope so, 'cause you're going to be stuck like that 
for a really, really long time." I hear Wendy take out 
a cell phone and start dialing. Then she clicks it over 
to speaker so I can hear both sides of the call. After 
a couple of rings I hear a familiar voice.

"Hello," my wife says.

"Hey, it's me," Wendy says. "I hope you were serious 
about what we talked about, 'cause we've got him."

"Already? Wow, that didn't take long."

"Yeah, he was pretty easy. A few beers and me in my bra 
and panties kissing another girl was all it took."

My wife laughs. "I'm sure. So where is he right now?"

"We're in that room at Meghan's place I told you about. 
He's tied in place, gagged and ready." Wendy smacks my 
ass sharply. "So... were you serious?"

"Oh absolutely," my wife says. "Completely."

"Well he's here listening right now, if you want to 
tell him yourself."

"Hey baby, how's your night going?" They both laugh. 
"Well just so you know, Wendy and I have been talking 
about what to do with you for a couple of months now, 
and I've agreed to let her have you for the weekend. We 
both know that you THINK you've been "secretly" lusting 
after her ever since I introduced the two of you, but 
trust me, you haven't really been very secret about it. 
And Wendy has been dying to try out some of her extreme 
fantasies, but didn't want to risk her relationship 
with her boyfriend. So we talked about how extreme your 
own fantasies are and it seemed like a perfect fit."

I try to mumble through my gag and pull on my 
restraints, but it's no good. My wife continues.

"I've told Wendy that she can do absolutely anything at 
all she wants to you for the next three days. Now just 
to be clear, we talked in detail about what her 
fantasies really are, and I know just exactly how 
severe this is going to be for you. She's spelled 
everything out for me and given me a very clear picture 
of what she'll be doing to you, and it's really, REALLY 
extreme. And I've agreed completely. I have given her 
my enthusiastic blessing to do all of it. Remember that 
when it all starts, baby. Wendy told me weeks ago what 
would be happening to you and I've given her my 
approval. And so, Wendy, so he understands what I'm 
talking about, why don't you remind me of what you're 
going to do to my husband."

"Well, I've got him tied to that wall I told you about, 
with his cock and balls passed through that glory hole 
and exposed in the other room. He's already been teased 
about a dozen times or so. The girls are having a good 
time with him. But when I go back over there we're 
going to start the REAL show.

"I've told everyone that the teasing is just the 
appetizer. What everyone is really here for is the 
chance to whip him. What I want to see is all of my 
friends taking turns using various belts and crops and 
lashes to whip every last inch of Paul's exposed cock. 
As soon as I get off the phone with you I'm going to go 
back over and tie his cock and balls like we discussed, 
tight at the base of the shaft to keep his cock rock 
hard no matter what we do to it, and then looped around 
his balls to squeeze them tight and hold them up into 
view."

Wendy moves close to me as she continues, talking close 
to my ear now as she describes what is about to happen.

"Once he's prepared I'll tease him a few times myself. 
And then I'll start the party off with the first 
whipping. I've decided to use a leather belt because I 
think it will be flexible enough to get all those hard 
to reach spots but easy enough to control that I can 
focus on specific areas. It's that brown braided 
leather one I showed you the other day. I think the 
braided leather will hurt a bit more than just the flat 
belt would."

"Good," my wife interrupts. "I mean if we're going to 
all this trouble than I at least want you to hurt him 
as much as possible."

"Exactly," Wendy says. "So, I'll whip his cock for a 
little while and then I'll turn him over to the girls. 
I want to watch what the others do to him. There are 
nineteen women here tonight that have agreed to whip 
and torture him, so I'm interested to see how they all 
go about it. Someone's bound to come up with something 
I haven't thought of yet. And I'm thinking about prizes 
for some things, like maybe 'most imaginative torture' 
and 'most painful torture', things like that.

"Anyways, after an hour or two of that I'll do the wax 
thing. I'll take a candle and drip hot molten wax all 
over his cock. You and I experimented with that the 
other day, putting wax just on our fingers and the 
backs of our hands just to see how hot it really was, 
so we know how much that hurt. Well I can only imagine 
how much more painful it will be on his cock, 
especially after it's been brutally whipped for a 
couple of hours."

"God, that sounds great," my wife moans. "Please tell 
me you're filming all of this for me Wendy."

"Of course. We've got three video cameras going and 
several of the girls brought their digital cameras and 
cell phone cameras. There'll be plenty of film to look 
at after this, trust me."

"Awesome. Hey, I was thinking. Why don't you shave him 
before you do all of this. I've heard that shaving a 
man's privates makes them more sensitive. And it'll be 
easier to get the wax everywhere if he's bare."

"Oh, good idea," Wendy says. She walks to the door and 
yells to the others. "Hey Meghan, go upstairs and get a 
couple of razors and shaving gel please!"

Wendy comes back over to me and continues.

"Okay, so I'll cover every single centimeter of your 
husband's tortured cock with hot wax, paying particular 
attention to the sensitive head. Then, once it's cooled 
and hardened I'll peel it all off and let the girls 
start whipping him again. Hopefully the hot wax will 
have left him even more tender than he already was and 
the whips will hurt even more. I want to see how red we 
can make his cock. I want everyone to whip him really, 
really hard. Every once in awhile I'll come back in 
here to see how he's reacting to the pain, and to check 
on the camera I'll have set up in here recording. But 
most of the time I'll be sitting right up close, 
watching his cock get redder and redder. I think his 
cock head will actually turn deep purple while we're 
doing all of this."

"Yeah, probably," my wife says. "I told you he likes 
for me to slap the head of his cock while I'm jacking 
him off, and even that gentle little punishment gets it 
deep red. I imagine all the things you're going to do 
to it will be a thousand times worse."

"Well I may have to do the whip-wax-whip thing a few 
times to get the pain and redness I'm hoping for. But 
that's okay. We've got time.

"When I've finally had enough of that I'm going to 
reach in and hold his sore, raw cock up out of the way 
and watch while each and ever person in that room takes 
turns whipping his cleanly shaven balls."

When I hear Wendy say that, and listen to my wife moan 
in satisfaction on the other end of the line, I cry 
out. I start struggling with all my strength to get 
free.

"Ooh, I think that finally scared him," Wendy says. She 
holds the phone closer to me so my wife can hear the 
sounds I'm making.

"Oh baby, yes. That's right, you should be scared. God, 
you have no idea how much I wish I was there to help my 
sister whip your balls, baby. Wendy, promise me you'll 
go first. I want to know you will be the first person 
to bring a real whip down hard on his balls. You can 
let everyone take a turn, but I want to know you'll be 
the first."

Wendy presses against my body and whispers directly 
into my ear, still holding the phone close so my wife 
can hear.

"You have my word, I will be the first woman to whip 
Paul's balls."

I scream into the gag, desperately trying to make 
myself heard. Wendy reaches up and loosens the gag just 
barely enough to pull it aside and let me mumble around 
it.

"Oh god, please don't do this. Honey, god this is too 
much. Wendy, please, PLEASE! I'm begging you, I'll do 
anything you want. You can do anything you want, just 
please not my balls. Do anything you want, but my 
balls... that's too much. God Wendy, please not that. 
That's too much. I can't stand that. You've no idea..."

Wendy is moaning, obviously turned on listening to me 
beg. My wife is turned on too, as she continues.

"Oh Paul," she says, "yes, that's it baby. Beg. Mmm, 
yes. We KNOW it's too much. We have a very good idea 
how bad it will be, and we don't care. Actually that's 
not true, is it Wendy? We do care. We care because we 
both WANT it to be too much. You'll stand whatever my 
sister and her friends decide to do to you because you 
don't have a choice. You have no choice but to stand 
there and take everything Wendy does to you."

"No... no please," I beg. "Baby please don't let her do 
this."

"Let her? No Paul I WANT her to do this to you. Wendy?"

"Yeah," Wendy replies.

"Wendy, promise me you'll whip his balls HARD. I 
really, really want you to whip those balls as hard as 
you can. I want your word that you'll torture and 
punish him more than he can possibly, possibly bear."

"Oh yeah, trust me. I promise. I will whip his cock 
till he wishes he didn't even have one. And then I'll 
spend hours, you hear me Paul, HOURS savagely whipping 
his tied balls. And when I've finally worn myself out, 
when my arm is too tired to whip him any more, every 
single woman here, all nineteen of them, will each 
repeat the process."

"Dammit Wendy, no, please, please, please don't do 
this. God! I can't take it. You don't understand... do 
anything you want to my cock. Please, just whip my 
cock. Burn it with wax and whip it again. Please, just 
please torture my cock. But not my balls... god, 
there's no way... you don't understand, I can't take 
that. I can't..."

Wendy shoves the ball gag back into my mouth and 
tightens it.

"You WILL take it, Paul," she says. "You will take it. 
Everything I've just told you will happen, and you'll 
just have to stand here and take it. It's not your 
choice. Begging is fun but it won't help you. Nothing 
at all is going to stop any of this. It's already been 
decided. It will happen and it will be too much for you 
and that's just too damn bad."

I hear my wife laugh on the phone.

"God Wendy, is it wrong for me to be turned on 
listening to my sister talk like that? It's wrong for 
me to be so turned on I could cum just listening to my 
sister whip and torture my husband."

"Well," Wendy says, "hurry back and you can join in."

"Yeah, I think I will. I think I'll try and head back 
early so I can help you guys. Can you occupy yourself 
with him for a couple of days till I get there?"

"Oh yeah. Most of the girls will be going home tonight 
or tomorrow morning. But I'LL be spending at least the 
next couple of days with Paul here. I know a guy that's 
curious and would probably be willing to fuck his ass 
for us if you'd like. Maybe I can get a guy or two to 
fuck his ass while you and I whip his cock and balls. 
Would you like that?"

"Wendy, you're a genius. You have a gift for this. Are 
you sure Paul is your first victim," she asks jokingly.

"Afraid so. That just means he gets to be my guinea 
pig. All the things I've always wanted to try I'll try 
out on him. Thanks for this by the way. This is the 
best present anyone's ever given me."

"Any time, sis. Any time. Now, I've got to get back to 
work, and so do you. Don't want the other girls to get 
bored and wander off before the fun starts. Just make 
sure you're the first to whip his balls, and make sure 
all the cameras are working. I'm going to want to watch 
and re-watch all of this."

"You've got it. Talk to you soon."

"Bye Paul," my wife says in a mock-innocent, sing-song 
voice. "Be good to my sister. I'll be back soon."

With that she hangs up and Wendy heads for the door.

"Okay, enough warm up. I'm going back in the other room 
and we'll get started. Are you ready, Paul? Just wait 
there, you'll know when it's time to begin."

She laughs and closes the door behind her, leaving me 
helpless in the dark with no idea of what's happening 
on the other side of the wall. But I know what's 
coming...

End

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life.

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