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K R I S T E N' S C O L L E C T I O N
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Exploration
by Ed Rider (edrider73@gmail.com)
***
Lester and Mandy get into "anal-play" against Lester's
better judgment. Although he has to admit that he cums
harder with Mandy's finger in his ass. What he hadn't
figured on was that this all might lead to "fisting",
while being videotaped by one of Mandy's girlfriends.
(MF, anal-play, reluc)
***
"What are you doing?" said Lester
"What does it feel like I'm doing?" said Mandy.
"It feels like you've stuck a finger into me," he
said. "Why did you do that?"
"No reason," she said. "I just wanted to see what
would happen. Carol told me it would arouse you."
"Have you changed your mind?" he said. "Didn't I try
that a couple of times when we first met and you got
really upset."
"You're right," she said. "And I still wouldn't like
that. The idea of your finger in my ass is disgusting
and the idea of you touching me anywhere with it after
it's been in there makes me feel like throwing up."
"What about your finger inside me?" he said. "Aren't
you afraid it will get dirty and disgusting?"
"Right," she said, "and as soon as I pull it out, I'm
going to wash it off in the bathroom. How do you feel
now?"
"I feel like you're moving it around inside me," he
said.
"Does it feel good?" she said.
"I haven't decided," he said.
"But Carol was right," she said. "Look at your penis.
A few minutes ago, it was exhausted, and I knew you
weren't going to be any more fun tonight. Now I'm not
so sure. Why are you squirming like that?"
"I don't know, but all of a sudden, your finger is
really getting me worked up, and it makes me want to
do this."
"No! No! Don't do that, Lester," she yelled.
"You're doing it to me, so I'm doing it to you," he
said. "You're squirming, too, so you must feel
something when I do that."
"If you take your finger out, I'll make you very glad
you did," she said, "No! Don't move it like that!"
"OK," he said, "but you need to take your finger out
first."
"It's a deal," she said, "when I count three, we'll
take them out -- but slowly -- and then we'll both go
to the bathroom and wash our hands and then we'll both
come back to bed, and then I'll make you glad."
"So this is all for me?" he said. "You're not going to
get anything out of it at all, are you?"
She laughed. "One-two-three!" she said.
***
"Are you exploring again?" said Lester.
"You know you like it," said Mandy. "No, wait, stop!"
"I told you," said Lester. "If you can do it to me, I
can do it to you."
"But that's not fair," she said. "You like it, but it
bothers me."
"I didn't ask you to do it," he said. "You aren't
doing it for me. So I'm not doing this for you."
"OK," she said, "but please be careful."
"Just as careful as you," he said.
"You're already responding," she said. "If you tell me
you don't like this, you're lying."
"Do you want to pull out now and wash your hands?" he
said.
"No," she said, "this time I want to leave it in while
we're making love. Let me work it out. I promise you,
you'll love it."
"OK," he said, "but mine stays in, too."
"What if the position doesn't work out that way?" she
said.
"You're going to make it work," he said.
She pushed and pulled him and shifted her body various
ways until she was satisfied. Then she began moving
against him. Her lower body was moving away from him
and back, pulling his penis into her and then out of
her. Meanwhile, her finger was moving in and out of
him with the same rhythm.
His finger was inside of her, but his arm was trapped
by her body, so he couldn't move it. When her body
moved, his finger moved with it. And then the double
rhythm of her finger and her pelvis got to him, and he
began moving his hips and thrusting back at her.
When he did, she started coming. He could tell right
away because of her anal spasms around his finger, and
that made him lose control and slam his body into her
in a wild orgasm of his own.
As he was pounding her, he suddenly felt something
strange distracting him, but only for an instant. He
was lost in convulsions and didn't realize what had
happened until he fell back exhausted.
"Hey!" he yelled as he jerked away from her. "What's
the idea?"
She was trying to catch her breath and didn't respond.
He looked at her, and she had a satisfied smile on her
face. He waited for her to respond, and when she
didn't after a few minutes, he was irritated.
"That was a dirty trick to pull on me while I was
coming," he said. "I never said you could stick a
second finger in me. You almost spoiled it for me."
"I think I made you come harder," she said, "because
you were so surprised. And there was plenty of room
inside you. It went in easily."
He didn't say anything after that, but when she looked
at him, she saw he was angry. She found out how angry
two nights later, when they were in bed and stroking
each other.
"Ow!" she yelled. "What are you doing? That hurts.
Please stop now!"
"Not on your life," he said. "I'm just catching up. I
didn't have a chance to put two fingers into you the
other night when you did that to me."
"But your fingers are a lot larger than mine, and my
anus is smaller than yours," she said as she tried to
move away from him.
"You should have thought of that," he said as he kept
his fingers inside her and moved his arm with her so
they stayed inside.
She stopped moving and turned to look at him. "OK, you
win," she said, "but take them out for a second and
let me do something. I promise you, I'll let you put
them back in. Please, Lester!"
He slowly pulled his two fingers out of her anus, and
when he did, she grabbed them and squeezed something
out of a plastic bottle over them and then massaged
the greasy fluid all over the fingers. Then she let
them go.
"OK," she said. "I covered your fingers with lube. Go
ahead, but slowly, please. Ow! It still hurts, but at
least it's better than before. I'll put some lube on
my fingers, too."
In a few seconds, she had two fingers moving inside of
him. He began moving his fingers inside her. Both of
them began squirming involuntarily a few moments
later. He was silent, but she was talking.
"This isn't fair, because I'm uncomfortable and you're
getting excited," she said.
"Then just take your fingers out," he said.
She didn't respond, but began maneuvering their bodies
again. This time he made sure she didn't get him into
a position where his arm was locked, and as they began
moving together, their fingers were going at the same
tempo. Both of them had massive orgasms, and as their
bodies went crazy, he once more felt something
different in his anus. She had pulled the same trick
again.
He didn't say anything while they were recovering, but
when she came back from the bathroom, he said, "You
know what's going to happen next time, don't you,
Mandy? Now I know why you brought the lube to bed.
Don't forget it next time because you're getting three
fingers, just like you put in me just now."
She didn't say anything.
***
The next couple of days, they didn't talk much. Then
Lester told her at breakfast, "This is crazy. I'm not
going to be in a bad mood for no reason. If you want
to be, that's up to you."
Usually, either Mandy or Lester initiated sex two or
three times a week, but neither made any attempts for
the next 10 days.
One night they were looking at each other, and they
could each tell what the other wanted. "What I don't
understand is that even though you say my fingers
bother you and disgust you and even hurt you, you
won't stop with your fingers," he said. "It's like
self-destructive behavior. Why are you doing it?"
"It's over tonight," she said. "All I know that
pushing my fingers into you gives me an incredible
feeling. I don't know why, but I feel powerful. I feel
like I'm in control, like I'm the man, and I'm putting
my thing in you like you put your thing in me.
"And the fact that you aren't happy about it, that you
don't want it but I'm doing it anyway, that makes it
even more exciting. I've never had orgasms before like
I had the last couple of times.
"But you're right, the price is getting too big," she
said. "Tonight, I'll let you put three fingers in me,
and I promise I won't put four into you, even though
I'm dying to and I know you can take them. I just hope
if I go hysterical with your three fingers, you'll
have a little compassion. I am so scared right now
that I feel like I might faint."
"OK," he said. "You win. It really bothered me when
you used three fingers last time. I'll admit that one
or two fingers were stimulating and even felt good.
But three didn't do anything except make me feel
uncomfortable and angry.
"So even though you owe me three fingers, I'll let you
win while you're ahead. If you want to forget about
this whole thing starting tonight, I'll let it go."
"No," she said. "I'm not ready to totally give up on
this, even though I know three fingers is going to be
horrible for me. But I am going to ask you to go along
with some things that I thought of."
"What do you mean?"
"Let's start with this," she said. "Look at my three
middle fingers. See how they're lined up side by side.
Now watch. I'm putting my middle finger behind the
other two fingers and squeezing all three together. It
makes them take up less space. Would you do that for
me?"
"Sure," he said.
"Thank you," she said, and she leaned over and kissed
him. "Please do it now for practice."
When he put his fingers together and then pointed to
show her, she reached under her pillow and pulled out
a cloth tape measure and wrapped it tightly around his
fingers. She looked at the numbers, and then she took
it off.
"OK," she said. "Now I want both of us to prepare."
"What do you mean?" he said.
"Before we stick our fingers in, I want us to be
clean," she said.
"Are you saying what I think you're saying?" he said.
"Yes, I'll go first," she said. "I've got all the
stuff in the bathroom. After I finish and wash myself
off, you'll go in and do the same thing. I'm hoping
that if I know you're clean inside and I am, too, I
won't think that I'm smelling anything and become
nauseous."
***
When he came back to bed 15 minutes later, he felt
empty inside and not aroused at all. As soon as he lay
down, he felt something go into his anus. "You're not
wasting any time, are you?" he said.
"That's not my finger," she said. "It's a bulb syringe
with a very tiny nozzle, so don't complain. I did it
to myself already. I'm squeezing a lot of lube into
you, so my fingers will move so smoothly inside you
that it won't hurt at all."
"Sure," he said. "Whatever you say."
After she filled him up with the slippery liquid, she
smiled at him and then got between his legs. He drew
his breath in sharply as her mouth began working on
him. Maybe because they hadn't had sex in so long, he
became hard instantly, despite the slimy feeling
inside him. She continued to stimulate him with her
mouth and her tongue and then she pulled her head up
and grabbed his penis with one hand and the cloth tape
measure in the other. She wrapped it around him and
looked at it, then took it off and tossed it aside.
As he felt her fingers enter him, he followed her
lead. Her third finger made him jerk as it entered.
Even with all the lube, it didn't feel good. It
stretched his anus and caused a stab of pain, but as
she began moving it, his anus enlarged, and it wasn't
painful anymore, even though it still felt intrusive.
He had to resist the impulse to move his body away to
get this uncomfortable foreign object out of his
insides.
When his third finger entered Mandy, she began shaking
uncontrollably and shouted out, "Stop! Stop, please!"
He pulled his fingers out.
"That was horrible," she said. "I don't know if I can
do this. Wait a minute." He noticed that her fingers
were still working inside him.
She stopped shaking and said, "OK, but very slowly
please. Oh no, oh no. Go ahead. Don't stop now."
He slowly inserted his fingers. When they were all in,
she took a deep breath and held it in for a while
before slowly exhaling. Meanwhile, her fingers were
going in and out of him and increasing their tempo. He
began doing the same thing, but much slower.
"What are you doing?" she yelled, and he stopped. She
breathed deeply a few times and said softly, "OK, I'm
sorry. Do it. I'll try not to stop you again."
As he increased his tempo slowly until it matched
hers, she made horrible little noises. She was crying
and shrieking and moaning in agony, but her fingers
never stopped inside him. They were plunging in
violently now, and they began hurting him again, but
he resisted the urge to do the same to her. He just
kept the same pace and tried to move his fingers
smoothly, like a machine.
She slowed down and began adjusting their bodies. He
was amazed that she was doing this because she was in
such obvious pain, and he wondered if he could even
get aroused enough for insertion.
But she must have thought of that, because he felt her
inhaling his limp penis and using all her oral magic
to get him hard. It worked, and when she lifted her
head, she quickly placed him at the right spot and
pulled him to her. She was under him and partially
sideways to him, and one arm pulled him and guided him
as their bodies began moving together, while the other
arm was reaching behind him and working her three
fingers inside his anus. They were tormenting him now,
pulling at the opening, stretching it, pushing in as
far as they could go and ripping into the soft tissue
inside him.
He had buried his fingers deep inside her, but she had
moved and was now she was lying on his arm, and his
hand was trapped, so all he could do was try to wiggle
his fingers. He noticed that when their two bodies
slammed together, his fingers were driven deeper into
her, and each time that happened, she screamed in
pain. But she didn't slow down.
He began crying and screaming, too, as his insides
were assaulted, and that's when he noticed her body
started to lose control. As he felt her shake with her
first orgasm, he was nearly over the edge himself, and
when she came for the third time, he slammed into her
so hard that he was afraid he might send her body
through the mattress. His screaming and crying never
stopped during his powerful orgasm. The pleasure of
his release was not enough to overcome the pain of her
torture.
After he came, she continued bucking underneath him,
and drove herself to two more orgasms before she
finally fell back and seemed to shrink into a lump of
flesh that was engulfed in gasping and sobbing beneath
him. Her fingers were still in him, and his were still
trapped in her as his full body weight was pressing on
her.
After a few minutes, she began trying to push him off
with her free hand. "I'm not moving until you take
those fingers out," he said, and his voice was so weak
it was barely a whisper.
"Sorry," she said. "I forgot." She slowly withdrew her
fingers, and then he rolled off her and slowly pulled
his out. They lay side by side breathing heavily for
almost 10 minutes, and then she got up and went to the
bathroom.
***
The next morning after each hobbled into the kitchen
and sat down painfully at the table, she looked at him
mournfully and then burst into laughter. He began
laughing, too, more in relief than anything else.
"We are crazy," she said, "and I admit it. I'm crazier
than you. I should have stopped last night when I
couldn't stand the pain anymore, but I was so turned
on by what I was doing to you that I had to keep
going. The more I could see you getting desperate and
breaking down, the wilder I felt. And when I came, it
was so incredible that I forgot about the pain you
were causing me for a while.
"But after that, the pleasure was over, and the pain
hasn't stopped yet. So in a way I'm glad we did it,
but I also know I'll never let you do that to me
again. It's just not worth it."
"So you're finally done with this," he said.
"I didn't say that," she said. "I just said, I won't
ever let you put more than two of your thick, long
fingers inside me again. But I still want to ravage
you with four of my slender fingers and then five and
then my whole hand. It won't hurt you nearly as much
as you hurt me last night."
"But that's not going to happen," he said. "I told you
the rule, a finger for a finger."
"I'm not agreeing to that anymore," she said, "but
I've got another idea I'm working on. Right now, we're
not in shape for anything, but once we're healed and
horny again, I'll tell you about it. I think you'll go
for it. So let's drop this for now. I can see you are
getting angry before you even know what I'm going to
say, so let's let everything cool down, especially the
burning inside my ass."
***
When they were recovered enough to have sex again, she
didn't bring up her idea, and he decided she had
thought better of suggesting it. At first, they
avoided their anuses completely, but after a while,
she began inserting a finger into him occasionally.
Each time, he followed her example, and that's as far
as it went.
One day, she said she'd like to work him with two
fingers again, and would he mind if they cleaned
themselves out once more. He went along, and after
that, they did the cleaning and fingering about once a
month. She attacked him hard, and he was sore after
each time, but she was, too, because he continued to
copy her.
After one of these sessions, when she had recovered
from multiple orgasms and both of them were tired and
sore, she said, "Will you listen with an open mind if
I tell you my idea?"
"What idea?" he said. "Oh, is this your idea for
sticking your whole hand inside my anus while I don't
do anything to you? Go ahead. I'm curious about how
you think I'd ever agree to that."
"OK," she said, "please hear me out and don't
interrupt me. And promise me you won't make a quick
decision and you'll think about it."
"I promise," he said with a laugh.
"Remember the night of the insane pain?" she said.
"Remember when I measured the width of your three
fingers before we started, and then when I got you
hard, I measured the width of your penis?"
"That's right," he said. "I wondered what you were
doing. What was that all about?"
"You know your big, thick, long hose?" she said. "I
adore it when you fill my vagina, but I freaked out
when you asked me once if I would ever consider taking
it in my ass. Do you remember? It was a long time
ago."
"I'll never forget that," he said. "You were so scared
that you were almost hysterical. I thought I'd have to
call a nurse to give you a sedative. I knew better
than to ever bring that up again."
"Well the other night, I found out that as big as it
is, it's barely bigger than three of your thick
fingers squeezed together. That got me to thinking
about what I want and what you want. So here's why
you'll let me put my hand inside you. If you do, I
will let you have anal sex with me. It would have to
be two different nights, because I wouldn't be in any
shape to do anything after you destroyed my ass. Yes,
I'd let you go first.
"OK, give me your first reaction. I'm sure it's
negative, but I'm prepared to persuade you. And
remember, you promised that you'd think about it, so I
don't want any final answer today."
"All right," he said. "First of all, I've managed to
do without anal for years. Yes, I liked it when I did
it with a few girls before I met you, even though none
of them liked it. Usually, that turns me off, but I
guess it's just like you getting excited when I'm in
pain from your three fingers, because somehow their
discomfort didn't bother me. I never tried to
humiliate and hurt them like you did me. But still, I
could tell they were having a hard time with it, and I
got excited anyway. So I suppose the same thing would
happen if I did anal with you.
"But I don't need it, and even if I did, I wouldn't
let you put your hand up my ass for that. I felt like
I was dying the night you ripped into me with three
fingers, so the pleasure of making love to your ass
wouldn't make up for the pain you would inflict on me.
"If you look at it logically, it doesn't make sense.
You said that my penis is about as thick as the three
fingers I put in your anus the other night. So if we
had anal sex, it would like the night of insanity for
you. But you really hurt me with your three fingers,
and you'd be putting your whole hand in. Why would I
agree to that?"
"You aren't looking at this right," she said. "Forget
about numbers of fingers. Just think in terms of
discomfort, humiliation and pain. My anus is much
smaller than yours, and your hard thick penis would
really hurt me, especially since the experience would
be a lot different than just sticking fingers into me.
"First of all, you're so long that you'd go halfway up
my intestines. Your fingers barely go a few inches in,
and that's enough to cause incredible pain. This would
be many times worse.
"And the motion of that gigantic thick thing --
especially when you work up a head of steam and start
pounding me into the mattress -- well, I get the
chills even thinking about it. I'm much softer and
more fragile than you. I would use as much lube as I
could, but I know you would still rip my insides to
shreds. There's no way I could hurt you as much as you
could hurt me."
"That all sounds great, Mandy," he said with a laugh.
"But you know you're exaggerating what I would do to
you and downplaying what you would do to me with a
hand that's much wider than my penis, or my three
fingers or even four fingers."
"I bet it's not as wide as four of your fingers," she
said. "I can measure right now. If I win, will you do
it?"
"No," he said. "And my final answer is no, too,
because it comes down to the fact that when you see me
humiliated and turned into a pathetic wreck from the
pain, it gives you tremendous orgasms. But I just
can't get as excited about hurting and degrading you.
Isn't that the bottom line?"
She ignored his question. "You promised to think about
it, Lester," she said. "Take your time. I can wait."
"You may be waiting for a long time," he said.
***
He pretended that he was giving it consideration. Then
he got worried that he might be raising her hopes, so
he told her three days later.
She was angry. "So that's your final answer," she
said. "You wimped out. I've seen lots of guys on the
Internet letting women do that to them. It isn't the
end of the world. And I'm not any woman. You know
you'd be safe with me because I would never do
anything that could cause you real injury. I'd be
careful.
"You know how much I want this because of what I'd be
willing to sacrifice to get it, and you still won't
give it to me. I'm just not that important to you.
"I could do it to you anyway if I wanted, but instead
I agreed to experience the horrible pain of anal sex
so you'd agree. But even that didn't get me anywhere,
did it? OK. I need to get out of the apartment. I
can't look at you."
He didn't say anything as she left, but he thought to
himself, if she leaves me over this, I guess I don't
know her as well as I thought I did.
When she came home a few hours later, she had calmed
down, and the first thing she did was embrace him and
kiss him for a long time. "I'm sorry," she said
finally. "I was so disappointed that I said some
things I didn't mean. You know I love you, and nothing
like this disagreement is ever going to change that."
"So are you telling me you're finally giving up?" he
said.
"I didn't say that," she said. "But I promise you
there won't be any more scenes like today. I still
want to do this, and I'm going to try to persuade you.
I can see that logic won't work and neither will
telling you how much it means to me. But there are
other methods."
He wondered what they were, and he didn't have to wait
long to find out. The first email arrived a couple of
weeks later. The messages were always unsigned and
short, along the lines of "I think you'll find this
interesting" or "Take a look at this one" or "Do you
think she's enjoying this?" With each message there
was a link.
He finally realized she must have subscribed to
several websites specializing in anal porn. The links
were to videos on the sites, and the ones she selected
all had one thing in common. The girls seemed to be
petite, with bodies similar to Mandy's, and the men
had huge equipment, most of it larger than Lester's.
And when the men began having anal sex with the girls,
it was obvious that the girls were in extreme pain.
Some of them tried to blink away the pain, some
furrowed their brows and some of them tried to breathe
fast or blow out air to lessen the pain, but by the
end, all of them were screaming, and most of them had
their eye makeup washed out on their faces from
crying.
Lester knew there were other sex videos with
professionals who laughed and smiled all the way
through anal sex, but these weren't the ones Mandy
chose. All of the ones she sent him made it look like
the woman was in extreme pain while the man merrily
pounded her until he came.
At first, Lester was embarrassed that he was
responding to the videos. He noticed that while
watching them, he was getting hot in his face and
aroused. One time, she walked into his home office
while he was watching one of them, and he quickly shut
off the video. But he couldn't hide how flush and
jumpy he was. She smiled at him and didn't say
anything.
After a while, he decided that there wasn't anything
wrong with his reaction. That's what the videos were
made for, to turn men on. He enjoyed them and at times
even looked forward to what bizarre video Mandy would
send him next. He deleted most of her emails with the
links, but there were a few that he really liked, and
he kept those and would watch them again at times. A
couple of times, when she was out for the evening at a
business meeting and he knew she would be too tired
for sex when she came home, he even masturbated while
watching a video.
But if the intention was to whet his appetite for
having anal sex with Mandy, it didn't work. Yes, he
thought about anal sex more now and sometimes
fantasized that he was doing it with one of the
actresses in the videos or maybe a stranger, but never
with Mandy, because as soon as he thought of that, he
thought about what it would cost him.
One day at dinner, she finally mentioned the videos.
"I know you are really into them, Lester," she said.
"And you know why I'm sending them. I want to work up
your appetite for having anal sex with me so you'll
agree to what I want. But I have to give you a
warning, too.
"I'm not waiting for you to tell me one day that you
give up and agree to my proposition. Here's how I
expect it to happen. One of the nights when we are
both cleaned out and using a couple of fingers on each
other, you're going to take the next step and aim your
penis at my anus. When you do that, I'll go along with
whatever horrible things you want to do to me, because
I'll know the deal is sealed, and I'm going to get my
end, so to speak, whether you have second thoughts or
not."
"Wait a second," he said. "You said that before, that
you could force me against my will. How are you going
to do that? Are you going to drug me? Don't you think
that's sick?"
"Of course that would be sick," she said. "And there's
an even better reason why I would never do that. The
whole point of my sticking my hand up you is for me to
watch you experience the pain and humiliation. I want
to see you blubbering like a baby. I want to watch
your face as your mind is reeling and you can't
control your muscles and turn into an imbecile. I want
to see your body squirm and twitch and shake
uncontrollably. If you were drugged out and didn't
even know what was going on, what would be the point?
"No, I worked out a way that I can do it to you, and
when I do, you'll be totally awake but unable to stop
me. Some other woman might just go ahead and do it
anyway, but I'm not like that. Everything's going to
be fair. You get your anal first.
"But you didn't let me finish my warning. There's
another way you can seal the deal, and I can get my
reward without you even touching me. The reason I send
you the videos are so that you'll want anal sex with
me, but you may be thinking you might be able to do it
with someone else. No, Lester, that won't work. As
soon as I find out, it means the deal is just as
sealed as if you had anal with me. And then I'll take
what you owe me.
"I've given you fair warning. If you don't want me to
get you more obsessed with anal sex, you can always
delete the links I send you before you open them. It's
up to you. You know I'm trying to condition you to
need anal sex like a drug addict has to have his fix.
If you have anal with someone else, even a prostitute,
I'm not going to be angry. It just means that my plan
worked. It would be different if you had regular sex
with another woman. That would be betrayal and
cheating, and it would mean the end of our
relationship.
"No, if you have anal sex with another woman, I'll be
happy, because whatever you do to her, I won't have to
endure any of it, and I get my end of the bargain
anyway. So I'm warning you again, Lester. If you have
anal sex with someone else and I find out, the deal is
sealed. But you know you don't need to do that because
when you want to have anal, I'm ready for it."
***
She didn't mention her warning again, and Lester
forgot about it, because he had never cheated on
Mandy, although he had many opportunities since both
of them traveled on business.
One of the opportunities was Carol, who lived on the
floor above them and was wild. They enjoyed going to
her parties, because they always met strange and
unusual people that they would never ordinarily come
in contact with. Occasionally, Carol would come over
to see Mandy. If he was around when that happened, he
had to be careful that his eyes didn't bug out.
Carol didn't just like to wear next to no clothes. She
wore clothes that pointed to all the best parts of her
geography. Her large breasts always looked like they
were falling out of whatever she was wearing, and her
shorts were tight and skimpy over her firm round butt.
She always flirted with Lester, and when she did, she
used graphic language so strong that Lester wondered
if she was really joking. He pretended that she was
and tried to stay away from her. When he told Mandy
about his run-ins with her -- especially the ones
where she grabbed his rear or groped for his testicles
or penis -- Mandy made light of his stories. He was
surprised, because usually, Mandy was extremely
protective and jealous. Finally, he decided that Mandy
liked Carol to come on to him, because Carol probably
reported every detail to her. For Mandy, it was a way
to test his loyalty.
It was probably because he was watching too much anal
porn, Lester thought, but lately Mandy's ass was
really catching his attention. She usually wore tiny
denim shorts that were plenty tight, but she had
switched to some thin, elastic fabric that looked like
she was naked and someone had painted her skin.
Whenever he saw her, whether it was her occasional
visits to Mandy or on the stairs or in laundry room,
it always seemed as though Carol was bent over with
her legs wide. A couple of times, he could have sworn
he saw her anus spread open beneath the fabric. One
time, she was wearing some yellow pants that were so
sheer that he thought her anus was winking at him.
It's saying come and get me, he thought. He finally
shook his head to snap out of it and hoped Carol
didn't notice him staring. It made him decide not to
watch the video links that Mandy was sending him, but
he didn't keep that resolution for long.
***
"I'm sorry, Lester, I found out this morning," said
Mandy. "We'll just postpone our plans to next weekend.
The weather is supposed to stay good."
"How could they make you do this at the last moment,"
he said. "I should call Franny. Maybe I can ask her to
let you off when I tell her how it's wrecking our
getaway."
"No!" said Mandy in a loud voice. "No, I don't want
you calling her. Just because she's been your best
buddy since you were 3 doesn't make it right. She
can't let me off, and if she could, everyone at the
office would hate me. Don't you dare call her or ever
mention this up with her."
"OK, OK," he said. "I didn't realize how upset that
would get you. Is everything all right? You seem
really on edge?"
"I'm fine, but I've got to pack, so I can leave first
thing in the morning," she said. "It will be over late
tomorrow night, so I'll drive back Sunday morning. I
should be home by noon. What are you going to do?"
"I don't know," he said. "The whole weekend's shot to
hell."
"Well, I know Carol's having one of her parties," she
said. "We were invited, but I didn't bother to tell
you because we had plans. If you end up going, please
don't drink yourself under the table just because
you're angry."
***
Friday night two weeks later, Lester was still in a
good mood from the previous weekend. They had taken
their postponed trip, and it couldn't have been more
perfect. The lodge was wonderful, the food was great
and the grounds were beautiful, but the best thing
about it had been Mandy. She had stopped being
irritable and peevish like she had been for the
previous few months.
All of a sudden, she was relaxed and warm and tender
and eager to do whatever he wanted. All her attention
was on taking care of him, even though he had planned
the trip to please her.
In bed she was like a rabbit. She always liked to make
him feel good during sex, but for the whole weekend,
she didn't even think about herself, although he
noticed that the more excited she made him, the more
excited she became. And that in turn aroused him even
more, so it was a spiral of lust that ended with both
of them exhausted by the time they got home late
Sunday night.
The afterglow hadn't warn off, and even though he
would have preferred some more wrestling in the
sheets, it was one of their scheduled finger pushing
sessions, and he knew they meant a lot to Mandy. She
had been smiling broadly all through dinner, and he
was sure it was because she was anticipating bedtime.
Her two fingers were working away inside him, and his
were doing the same inside her for a while, and he was
waiting for her to move their bodies into whatever
position she wanted to for them to consummate when he
felt it. "Hey!" he shouted. "Stop that!" But it didn't
stop. He felt a third finger sliding into him. It
didn't hurt too much because his anus had been
loosened from the pushing and pulling of her two
fingers, but it bothered him anyway.
"You told me you never wanted to use three fingers
again," he said, turning his head to toward her. He
didn't see her face because her upper body was down by
his crotch, but he could hear her reply.
"I didn't say that, Lester," she said. "What I said
was that I would never let you put three of your thick
fingers inside me again."
"But that's what I'm going to do, Mandy," he said,
"right now. I told you before, a finger for a finger."
"Not anymore," she said, "and this is why."
"Ow!" he said as he doubled up in pain. "What was
that? You've never done that before. That was cruel."
"I'm sorry, Lester," she said. "Please be quiet for a
minute and listen to me. I don't want to do that
again, but I will if I have to. Will you listen to me
for a minute? After that, you can say anything you
want.
"I said you weren't going to put another finger in me,
and you just found out the reason why. My right hand
has three fingers in your nice, clean anus. There's a
ton of lube in there. Do you hear the squishy sounds
of the lube as they go in and out and how I'm slowly
increasing the pace?
"The reason I can do that is my left hand has a good
grip on your balls. The grip is snug, so I hope your
balls feel comfortably warm, and maybe you will even
get aroused. But right now, you need to take both
fingers out of my anus, and you are not going to put
any of them back for tonight.
"Did you understand what I said, Lester. Take those
fingers out now, because I'm starting to make my snug
grip even snugger, and soon I'll be squeezing your
balls as tight as I did a second ago, when you nearly
passed out. If you do pass out, though, don't worry.
I've got some smelling salts handy, and you'll soon be
awake again, because I want you involved with me as I
put my hand into your anus tonight."
"No!" he screamed. "Are you crazy? Why are you doing
this?"
"It's not time for you to talk yet, Lester, because
your fingers are still in my anus," she said. "If you
don't remove them slowly right now, get ready for some
real pain. That's it. Slowly glide them free. Now
we're all set.
"I see your body is starting to react to my three
fingers, Lester. You're shifting around from the
discomfort. I just slowed the pace, and now I'm
working in my fourth finger. Did you feel any
difference? The four fingers are all going in and out
now, just as smoothly as the three did. I told you
that you could take four.
"OK, as I slowly increase the speed again, I'll answer
your question that you asked a few seconds ago. Why am
I doing this? The answer is because I said I would do
this, I warned you I would do this, and I promised you
I would do this. You sealed the deal, and now I'm
doing what I promised I would do.
"Do you have anything to say, Lester, any questions?
Are you thinking about telling me any lies? Are you
going to say it's your word against hers? You can save
your breath, because I know for certain what you did.
Oh, did you see all those lights go on? And here she
is, the beautiful Carol.
"She is such a slut. Look, she even took all her
clothes off because she's so excited by this. No,
we're not having a threesome. She's holding that video
camera because she's been shooting us from across the
room since we got into bed. But now she can come out
of hiding and turn on all the extra lights I rented,
so the video is bright and crystal clear. Everything
is being shot in slo-mo as well as regular speed, so
I'll be able to watch my hand going in you inch by
inch and seeing what each inch makes you do with your
body and your face.
"Yes, I know all about Carol's party, and how drunk
you got and how you were lying on her couch when
everyone else left and how she danced her slutty dance
and shook her butt for you. The lights were low for
the party, but then she turned them all on, and as she
waved her ass in front of your face, you could see she
wasn't wearing panties and her thin white shorts were
so stretched that it looked like she wasn't wearing
anything. Despite all the drinks, you were as hard as
a rock, and you ripped off your pants and grabbed her
and pulled off her pants and plunged right into her
ass. You were so excited that it was less than a
minute before you gushed into her guts.
"Do you want to deny it, Lester? Do you want to say
something besides those moans. I wish I had you inside
me right now, because your responses are getting me so
turned on that I think I could come in a second. But I
couldn't figure out a way to do that and get my hand
into you at the same time, so that will have to wait.
"Did you forget about how you sealed the deal? Maybe
you thought you had imagined it. But it was real, and
so is this, my thumb. I slowed down again, and I'm
tucking it behind the other fingers and moving it into
you slowly and carefully now. You'll see on the video,
I'm all the way up to the second knuckles.
"For now, we're going in and out slowly and carefully.
I like the way you're working hard to handle it,
Lester. Yes, try those breathing things. Maybe they'll
help. I'm going slower and slower, and now I'm
stopping with my fingers inside as far as they will
go. No more in and out now. It's all one way --in. I'm
gently pushing all the fingers into you. You're very
tight all of a sudden, because the largest part of my
hand is at the opening and can't get any further.
"But I'm going to be patient, like I've been patient
with you for months now. You are resisting my hand,
just like you resisted what I wanted to do. We could
have done this a long time ago with your cooperation.
You could have used my anus any way you wanted to and
really made me earn this, instead of sealing the deal
in less than a minute during your drunken night with
Carol. But you made your choice, and like I told you,
I'm not angry. At least I know Carol didn't give you
some disease.
"I think I felt something, Lester, and I definitely
hear something. You're starting to howl like a dying
animal, and I think your ass is going to cave soon and
let me in. Let me help it by twisting like this. Oh,
that was some scream. I'm all wet between my legs. I
think I may have come once already without knowing it.
"Oh, oh, oh. There it goes. Thanks for that scream as
your ass swallowed my hand up to the wrist. It was the
best one of all. Oh, Lester, you're crying now. You're
just bellowing and the tears are coming in a flood.
You're just a little boy who wants his mommy to make
his boo-boo go away. You sound pathetic, and I feel
sorry for you, and that feeling is getting me even
more excited. Did you feel that through my hand inside
you? I just came two more times.
"OK, I think we rested enough. Now I'm going to pull
my hand gently out of you. I'll push the fingers
together and glide out like this through all the lube
and watch your anus open up, and there, we're all out,
and now we glide right back in. See, it didn't hurt as
much the second time. I could tell by your groan.
"Let's pull it out a little faster now, and put it in
a little faster. That looked fantastic, especially the
way your body jerked as my hand pushed in to the wrist
and then was ripped completely free.
"Let's increase the speed now. Oh my, look at you jerk
like you're in the electric chair. I wonder if that
hurts more than this. I don't think so. Oh, I just
came again. I think I could keep coming all night if
we kept this up, but I don't want to turn you into a
vegetable. So let's just do a few more times, and then
we're going to try something so hot that I came the
other day when I just thought about it.
"When you accused me of getting off on watching your
humiliation and pain, you were right, Lester, but only
partly right. What really makes me go out of my mind
is when you are humiliated and in pain and you come
anyway. Because you're trying to deal with what's
going on inside your ass, you resist the pleasure, but
then you can't anymore, and the pleasure ends up
causing more pain and mortification, and you have this
great orgasm, but it feels horrible at the same time.
When I see that, I almost explode with orgasms.
"So now that I've got a good rhythm going in and out
of your ass with my right hand, I'm going to lean over
and do this for a while. Mmmmmmm.
"Boy, I had to really suck hard and stroke your balls,
but I finally got you aroused. I think I could bring
you off quickly with my mouth, but then Carol wouldn't
see anything with her camera. So I'm going to use my
hand to pump you. There's a lot of lube over
everything now, so the pumping is easy. I'm gliding up
and down your big, thick penis even while you're
trying to move away from me and whimpering.
"You got a little slack there again. I need to get my
mouth back to work and suck you hard. There, it didn't
take as long this time. And now I feel you starting to
respond to my hand, even while my other hand is making
you grimace and moan. I don't think it will be long
now.
"It's coming, I can feel it. Now I'm raising your
penis straight into the air while I pump it, and there
you go. Yes, go Lester, thrust your pelvis and get it
all out. Are you crying tears of joy while you're
screaming so loud? I just came three more times.
"We're almost done. I'm going to let you rest up a
minute for the last part, because it's going to hurt
the most of all. OK, I'm starting. See what I'm doing?
I'm pulling out of you just as slowly and persistently
as I pushed into you, but I made my hand into a big
fist inside you, so coming out is going to be
difficult and raise the bar to a new level of pain and
mortification. I see you feel the strain already. Your
head is turning in all directions, or rather, it's
jerking. I don't think you are even a human being
right now. The pain has clouded your brain, and you're
just reacting like a bug would react if I tried to
squash it.
"What's that you say? Are you saying 'Mommy?' Yes you
are. You've regressed all the way to infancy. Now
you're screaming like a maniac because you feel the
fist starting to move toward the opening. I see part
of it, and it's coming this way. Oh my god! Did you
hear the sound as it popped out? Like a gun. And look
at the hole. I think I could stick two hands into it,
it's so big. You'll see on the video. Now let's watch
what happens.
"It's staying open like a manhole -- it is a manhole -
- but now I see it's starting to slowly close up. As
soon as it closes all the way, Carol will turn off the
cameras and lights and go back upstairs, and call her
new boyfriend over to service her, because I can tell
she's about to burst with excitement. If he's not
available, she'll have to use her fingers or go mad. I
would loan you to her, but I don't think you'd be able
to help her the way you look now.
"I'm sorry. I take that back. I'm not loaning you out
to anyone. That was a feeble joke. You are one amazing
man, Lester, and I'm going to work just as hard to
make this up to you as I did to destroy you today. It
will start tomorrow when you wake up. For now, let me
get you as comfortable in bed as I can. Yes, don't try
to keep your eyes open. Sleep, Lester. Sleep."
***
He slept until Saturday afternoon. When he woke up,
she was sitting in a chair next to the bed, and he
glowered at her. She got up and pointed to some fruit
and water on his nightstand and left. He ate a few
things and then fell asleep again, waking up Sunday
morning at 5 a.m. She wasn't in bed next to him, and
it felt strange. He made a move to get up, but it was
so painful that he just lay there staring at the
ceiling and thinking about Mandy and how they met and
the great life they had had together and the wonderful
weekend last weekend, and how it was all over now and
how horribly it ended.
When he woke up about noon, she was sitting next to
him again. She began speaking to him, but he waved his
hand at her and painfully sat up. Then he got up and
went to the bathroom, where he screamed loudly while
he was on the toilet. He was exhausted when he came
back, but he sat down in an easy chair. When he
attempted to talk, his voice was weak, and he felt
tired, so he soon gave up and glared at her.
She smiled at him. "I'm not going to try to soften
your anger, Lester," she said. "I was determined to
experience what happened two days ago. You may not
believe me, but I'm even more determined that we get
past this. I want us to as happy as we were last
weekend.
"You're going to be angry, because I'm not going to
lie to you. I respect you for not lying to me. You
know what you did with Carol, and you didn't make
excuses. You know that she didn't offer you one drink.
She wasn't allowed to. You got roaring drunk all by
yourself, and that made you forget the deal.
"She also wasn't allowed to touch you. If you hadn't
pulled off her pants and been the aggressor, nothing
would have happened. So I had every right to do what I
did. But I admit that I set up the opportunity for you
to make the bad decisions, and I was hoping really
hard that you would so that I could achieve my goal.
"The office didn't ask me to go on that business trip
at the last minute. There was no trip. I hung out at a
friend's house the whole day, and then I snuck back
after dark and hid out at Carol's getting things
ready. That's how I know exactly what you and Carol
did. I was hiding in the same room and watched it
happen, and I filmed it, too, just in case you were
going to deny it.
"Carol was excited when I told her my plan, and that's
why she was displaying her ass for you whenever she
could for the last few weeks. I was worried that you
might hurt her, but she told me she would be heavily
lubed, and she was sure she could get you so aroused
that you wouldn't last long. And she was right.
"When I was watching you, I found myself thinking
about what I'd do if you didn't go after her. Would I
give up, or would I keep looking for a way to get what
I wanted? But then I didn't need to wonder anymore.
"I've watched the video of us twice already, and Carol
did a great job of capturing all the pain and
humiliation. The best part is at the end where the
pain and pleasure were so intense that you went insane
for a while. I came at least twice each time I saw
that. So I got what I wanted.
"But now that my goal has been achieved, I can see
things more clearly. You knew exactly what I was doing
when I sent you those videos, and you had the choice
of not watching them, but I was the one who sent them,
and I'm sure nothing would have happened if I hadn't
done that.
"What I'm telling you is that you have the right to be
angry. I think there's a difference between entrapment
and creating circumstances that make something
possible, and I didn't cross that line. On the other
hand, if I were you, I might disagree. That's why I'm
not going to count what you and Carol did for the
other part of the deal.
"Yes, I'm still going to give you my ass. I'll wait
until you are all healed and healthy, and as I said,
I'm not going to do anything that will make you less
angry at me. I'm dreading it, because I know you'll
take out all your anger on my anus and I won't be able
to handle it anywhere near as well as you did. But at
the same time, I'm anxious to do this, because knowing
you, I think after you destroy me and you see my body
in the kind of pain you're experiencing now, you'll be
as sympathetic as I am right now, and it will begin
our mutual healing.
"So I'm going to keep sending you links of painful
anal scenes, even though I know they will be teaching
you some horrible things that you will do to me. In a
month or so, when you aren't hurting anymore and are
back to full strength, you'll select a night, and I'll
be cleaned out and lubed up and ready to suffer.
"And Carol will shoot a video of you destroying my ass
for you to watch later, because I think that's fair.
I'm sure you'll never agree to do anything like this
again. That's why I wanted the video to preserve it.
Whenever I feel excited about humiliating and hurting
you, I'll watch the Lester on the video. But I won't
ever hurt the real Lester again.
"You told me how happy I made you last weekend and how
I seemed like I was glowing. Now you know I was
glowing because I was thinking about what I was going
to do to you on Friday. I hope that makes you angry,
not sad. But I promise you that from now on, I'm going
to make even better memories for us, and my happiness
will come from the joy of pleasuring you, not because
I'm looking forward to degrading and hurting you.
"That's all I've got to say, except I hope you give me
a chance to show you I'm telling the truth."
END
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Please keep this story, and all erotic stories out of
the hands of children. They should be outside playing
in the sunshine, not thinking about adult situations.
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Kristen's collection - Directory 78