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From: Mike Chambers <mikechamberswrites@hotmail.co.uk>
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Subject: {ASSM} To Take Advantage Of A Friend (MF, reluc) by Mike Chambers
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Date: Sat, 13 Dec 2008 11:10:03 -0500
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To Take Advantage Of A Friend (MF, reluc) by Mike Chambers



I would never have thought it. I had known Jane eight years,
and although she was cute-pretty - five nine, blonde, with a narrow boyish
figure - we had never moved beyond low key flirting. Truth be told, despite her
niceish looks she wasn't that sexy. Too cold. So the possibility that, for a
week, she would submit herself to my every whim and fancy, well it wasn't even
fantasy, because I had never considered the details of fucking her.



Then she screwed me over big time, a monstrous piece of selfish shitty behavior,
that cost me money and even risked my career. A groveling e-mail followed, but
my fury and disappointment led me to simply ignore it. For several months
silence, then this e-mail:



"I miss our friendship. I'm so sorry for what I did. I would do anything
to put it right. Please reply. Jane."



I deleted the mail, my anger still burning too brightly. But a little later in
the day I remembered Jane bending across a table and the way her jeans had
pulled a little into her ass crack. A boyish figure, yes, but not a bad ass.



And she'd just said she'd do anything.



I felt a rush, a burst of excitement. My whole body tingled with just the
possibility. Anything? I couldn't, could I?



I checked frantically for her deleted mail, and thank heavens it was still
lurking in the system. If nothing else happened, it could still form the basis
of many a happy fantasy.



"Anything?" I clicked Send. I felt so powerful, because I didn't
care. If she reacted the way I expected, then I could go back to how I'd been
before, with Jane receding into that part of my memory devoted to former
friends.



And yet it was all to evident I really did care. The next hour and a half was a
high tension waste of time, as I waited for her reply. We were both at work,
she was usually in her office, so there was no reason for a delay. Each ping of
a new mail caused my cock to stir, only to be disappointed when I found out it
was not Jane.



Then "Sender: Jane Re: I'm Sorry". Her message was brief, and
something of an anticlimax. "What do you mean?"



I wondered briefly what to say, but the momentum of my excitement wouldn't let
me think too long about my reply.



"I mean will you do ANYTHING to put things right?" I clicked Send,
the awkward throb of my cock pulsing in my suit pants telling me this was one
of the most exciting games I'd ever played.



Jane's reply was almost immediate. "I'm sorry Mike, I'm not really sure
what you mean but yes I do want to be your friend, and if you tell me what I
have to do to make up to you then I'll try to do it."



I still wasn't sure that Jane totally understood exactly what I was implying.
It was time to make the final pitch.



"If you want us to be friends, Jane, you have to agree to do ANYTHING I
want for the next week. ANYTHING. If you don't agree, then this e-mail is the
last thing that you will ever hear from me. If you do agree but then refuse to
do something that I ask, then you will never hear from me again. But if you do
anything I want for a week we will be friends." Given some of the ideas I
already had in mind this last sentence seemed a little inaccurate, but that
didn't matter for now.



There was a longer pause now, which was agonizing. I felt as if I was so close
to the most extraordinary thing, but I knew that surely Jane must say No.



Then: "I'm really not trying to be difficult, Mike, and I so want us to be
friends again, but I do want to know what I'm getting myself into! Can you
please give me an example of what you mean by ANYTHING?!?"



Surely she didn't think I was expecting her to cook cordon bleu meals for me
every evening? Or to rob a bank?



By now the pressure of my cock was almost unbearable. Being at my desk in my
office (at least I had my own room, as did Jane), made my discomfort even
sweeter.



I took a deep breath. This really was it. "Okay. At the very tamest end of
what I mean by ANYTHING, tell me what color panties you're wearing."



The reply was swift. "I see. Navy."



"When did you last make yourself come?"



"Sunday morning."



"Have you ever had a cock in your ass?"



"No. Is that what you want to do to me?"



I looked at my watch. Four thirty. I couldn't possible leave for another hour.
How beautiful and agonizing that would be. "You'll see. I'll be at your
apartment by six."



++



I got to Jane's apartment block early. Partly it was sheer excitement and need
- that first day I was in a daze. But I also wanted to catch her off guard, to
stop her having any time to prepare herself or to divert me from anything I
might want.



Jane was dressed casually - a career in the media - and walking quickly as she
made her way to the entrance to the block. Jeans, a pale cream sweater, all
setting off her tall skinny figure well. She was so absorbed in her thoughts -
now what were they I wonder - that she was almost on me before she saw me.



"Hi." I decided not to smile. It wasn't appropriate for our new
relationship.



"Hi." Before we'd kissed when we met, but this was very definitely
not before any more. Her uncertainty was both exciting and slightly scary.
Having got her here I didn't want her walking out.



We didn't kiss. "Shall we go up?" Her tone was brusque but I guessed
that was nerves.



Up in her apartment she poured us both a glass of an expensive little Chablis.
I sat on a chair, studiedly alone, and she was on the couch, sipping nervously.



"Listen, Mike, I really am sorry about..."



I cut in quickly. "Forget it. We're resolving things a different way. But
I will say I really hope this next week works out okay."



"Yes. So do I." Now that she was there, in the flesh, my friend Jane,
it was so difficult to start. I'd sat here so many times, talking about
anything, could I really start issuing sexual orders? I was so close to blowing
it, to giving up, when I found a way to get started.



"So, navy panties." Jane nodded. "Do you ever wear other
colors?" Another nod. "What colors?"



"White. Gray. Sometimes red. I don't really think about it."



"Do you ever wear thongs?" I was easing us into intimacy.



"Sometimes. Usually if I'm wearing a skirt."



"But you're wearing panties now."



"Yes."



"Navy blue panties."



"Yes."



"Show me your navy blue panties Jane."



She put down her wine glass and stood up. Was she walking out? "Do you
want me to take my jeans off?"



"No. Just pull them down so I can see your panties."



Jane fiddled with the metal stud, her hands shaking, then the zipper was
sliding down and a vee of blue material was visible before she pulled the rest
of the jeans down to her thighs.



"Come here." She walked awkwardly with her jeans like that, but then
she was standing so close. "Show me your titties." It was a conscious
decision to be coarse - I wanted the brutality of our respective positions to
be explicit.



Jane raised her eyes a little - what had she got herself into? - but then she
reached to the bottom hem of her sweater and lifted it up and over, tugging up
her bra as she went.



I had always thought that Jane was a little "light" up top, and sure
enough her poor little breasts didn't stand out too much, but what she lacked
there she made up for in the length of her nipples. They must have been an inch
long, chewy brown pencils just aching to be bitten and tugged. It was also the
first sign she was turned on by what we were doing or, rather, what she was
doing for me.



"Your nipples are stiff Jane."



"Yes."



"Are you turned on?" She shrugged. I could feel a little battle of
wills coming on, and I was determined to win it. "Are you turned on, Jane?
I want to know. I want you to tell me."



"I guess. Maybe a little."



But her feeble little act of resistance had worked against her, spurring me on
to more.



"Is your cunt wet?" Again Jane raised her eyebrows. I knew she didn't
like the C-word, even in a social context, let alone when it was referring to
her own genitals. "Answer me. I'm going to find out in a second
anyway."



"Yes. I guess. A little."



"Show me your wet cunt, Jane." Again the eyebrows raised, then Jane
slipped her hand into the elastic waist of her much-discussed navy panties and
pulled them down to join her jeans at the top of her thighs.



I was intrigued to see that Jane had a neat but full triangle of mid-brown
hair, a clear but pleasing contrast to her straw blonde head hair.



"Show me your wet cunt properly, Jane." She paused, wondering how to
comply, then thrust her hips forward, bringing her pussy even closer to my
face.



I could now see clearly that Jane's labia were swollen and puffy with her
excitement. "Your cunt is soaking Jane. Tell me your cunt is
soaking."



"I'm soaking Mike."



"Tell me properly. Tell me your cunt is soaking."



"I... Mike, please, you know how I hate that word." How weird, that she
could expose her naked body to me but she balked at saying something.



"Tell me your cunt is soaking."



"I...my c-c-cunt is soaking."



"Good. Now show me your ass."



Jane turned slowly around. From what she'd replied in her mail and from what I
knew of her personality anyway, I guessed she'd always been more of a front end
girl. Well that was about to change.



Jane had a lovely rounded bum, a slightly surprising contrast to her flat
chest. "Pull your ass cheeks apart for me. I want to see your
asshole."



She reached around, maybe a little shocked at the level of intimacy I expected,
and separated her cheeks a little.



"More." She pulled again and her tight little anus winked at me. Her
virgin anus. I reached out and gently pressed a fingertip against it. Jane
jumped a mile - it was, after all, our first physical contact. I gently stroked
her grimy little hole. "So you've never been fucked up there?" She
shook her head. "Never had anything up there?"



"No."



"But you're going to let me fuck you there?"



"I...I suppose so."



"I'm going to fuck your asshole?"



"Yes."



"Say it."



"You're going to fuck my asshole."



"Good. Now kneel between my legs. Facing me. That's good. Now pull out my
cock." Even the touch of Jane's hands on my zipper was nearly enough to
send me over the edge - it had been a long few hours. And it was the most
exquisite release as she sprung me free just inches from her nervous face.
"Okay Jane, for our first time you're going to bring me off over your
face. Later on I'm going to fuck you in each of your holes, but for now we're
taking it simple."



Jane reached up, without even being asked, and began stroking her fingers
around the shaft of my cock. Her grip was a little hesitant at first, but that
almost increased the delicacy. "Tell me what we're going to do later
Jane."



"You're going to fuck each of my holes."



"Tell me about what I'm going to do to your virgin ass Jane."



"You're going to fuck it."



"Say everything properly, Jane."



"You're going to fuck my virgin ass."



"Am I going to come inside your tight virgin asshole Jane?"



"If you want to." 



"Then say it."



"You can come inside my tight virgin asshole if you want to, Mike."
The look on Jane's face was positively coquettish as she said this, and it was
all too much as I boiled over, shooting thick white gobbets of sperm onto her
face, Jane still stroking carefully and slowly, obediently keeping her face in
position as I shot my come all over her.



I flopped back, briefly totally spent. But the sight of Jane - my friend Jane -
still kneeling dutifully between my legs, her face spattered with my come and
her nipples poking out even more stiffly, started an almost immediate reaction
in my cock. I looked at my watch. "Six days, twenty three hours and thirty
minutes to go." Would you believe it, she almost smiled?



++



In fact I didn't take Jane's anal cherry that evening. It seemed far more
piquant to allow her to anticipate it for a while, and so I told her that she
would be ass-fucked the following evening.



All through that next day I sent her e-mails, reminding her what was going to
happen, forcing her to describe in ever more detail and using ever filthier
words to tell me what would be done that evening. It was tempting to get her to
start doing things to herself while at work, but reminded myself that drawing
things out would be more fun.



Once again I beat Jane to her apartment, and although once again she was
walking quickly as she walked around the corner, I thought this time maybe the
motivation was excitement, not fear.



For just a few minutes upstairs the same "being face-to-face"
awkwardness surfaced, but then Jane fetched us some Chablis and we seemed to
fit back into the previous night's roles.



I told her to strip, kneel on all fours on the bed, and pull her ass cheeks
apart for me. I spent a little time pointedly and carefully inspecting her ass,
knowing that such an intimate exposure would be embarrassing and maybe exciting
for her.



Maybe for some people in my position and with my control over Jane the obvious
thing would have been to simple fuck her ass straight away, driving hard into
her tender hole regardless. But I was far more interested in cold hard Jane
discovering that she loved to be ass-fucked, just like she'd found - so I
believed - that she got turned on being subjugated to my will. Far more
exciting for me to see coming and coming from the sordid pleasures of
ass-fucking than the simple buzz of her face contorted with pain. And the pain
would happen anyway, I knew that.



I told Jane to ask me to lick her asshole. Starting cold, so as to speak, she
struggled to begin with but soon managed the request. She actually gasped as
she felt my tongue press against her hole, and quickly she was pushing herself
back against me, loving the firm wet sensation as I probed her sphincter.



"Feels good, huh?" I asked, momentarily pulling away, and her nodded
response persuaded me to try a little diversion from the main task at hand.
"Lick my asshole then Jane." She rolled over onto her side, looking
at me warily. She hadn't expected that.



I lay back on the bed, lifting my knees up to my chest, exposing my asshole to
her. She looked away. As I'd figured, doing my asshole was a whole different
proposition.



"Come over here slut." It was the first time I'd used an abusive
term, and Jane flinched. I could see she was calculating whether to give up on
the whole deal. Slowly, reluctantly, she crawled across the bed. When she was
close enough I grabbed her hair, and she flinched more than before, expecting a
strike. But instead I coaxed gently, drawing her face ever closer to my ass.
The look on her face was so repelled by what I wanted that I could almost hear
her whimpering. As she got close to my ass she began to resist, holding herself
away. But my grip was firm and impassive and she found herself just inches from
my bare ass. Her eyes were closed.



"Open your eyes, slut." Nothing. "Open your eyes and look at my
asshole." I gave a gentle tug on her hair and her eyes opened. "Look
at it." Her gaze turned. There, it wasn't so bad. "Okay now lick
it." I drew her in, she wasn't so much resisting now, then at first Jane
was kissing my anus with her lips and then as I held her tightly in position I
felt her tongue poking against it too. "Good little asslicker," I
murmured, "now open your eyes and look at me," and then our gazes met
as my friend Jane tongued my asshole for me.



++



Because I wanted to see Jane's face as I penetrated her asshole for the first
time, I told her to lie on her back. She seemed confused, maybe relieved, as if
this meant she wasn't going to experience the unavoidable agony of being
assfucked.



I told her to put her knees up and realization dawned. To prepare her properly,
I rubbed around her anus with my fingers, slicking up my fingers with her
juices (yes she was soaking). I pressed a fingertip against her asshole and she
tensed, sensing what would follow, and I moved my mouth to her clit to lick and
relax her. As my finger slid into Jane's asshole I could hear her breath in,
but I was confident that the combination of a finger in her ass and my tongue
on her pussy would quickly be delicious. Sure enough she soon relaxed, and I
could hear her moan each time I poked my pinky up her butt.



The sensation for me, too, was exquisite, Jane's anal canal so tight and hot
around my finger. Once she was comfortably into me finger fucking her ass I
repeated the same slow delicate procedure with two fingers. This time her
tension took much longer to subside a little, and I could feel that she was
struggling to cope with such an alien presence in her bottom. But as I
continued to lick her clit while my fingers poked in and out I could sense that
she was beginning to understand how delicious her discomfort could be.



As I slid my fingers out the look on Jane's face turned to true apprehension,
sensing that the time had come for the preparations to end. I experienced a
strange mixture of emotions, the part of me that remembered my friend Jane
concerned and tender, but another, far greater emotion was pleasure that I was about
to do this to her poor innocent behind.



I slicked my cock in Jane's cunt juices then rested it right up against the
entrance to her most private hole. Her eyes were wide open now, looking
directly at me, wanting somehow to connect with me as we shared what was about
to be done to her. As I began to press into her asshole Jane's eyes opened
wider, as nothing that my fingers had done had prepared her for the monstrosity
of what was entering her bottom.



I moved quickly, knowing that that first penetration is the worst part, but
relishing the extraordinary sensation of the walls of Jane's tight sphincter
gripping my cock. I began to slide slowly in and out, Jane's mouth making a
permanent "aaah" shape, her eyes never leaving mine. I lent down to
chew on those extraordinary nipples, providing Jane with an entirely new set of
sensations. I reached to stroke her clit, which I found was throbbing away at
this multiple assault.



Still chewing Jane's nipples, I began to urge Jane on. "Come for me slut.
Come for me with my cock in your asshole. I want you to have an assfucking
orgasm. Come on my cock, slut." Looking up I could see that Jane was in an
amazing place, overwhelmed by the intensity of her first experience of anal
sex. Then she was bucking and thrusting, her face contorted with the pain and
pleasure of her violation. That was enough for me, and I released too,
shuddering at each explosion, releasing my sperm deep into Jane's bottom. Our
eyes were locked, and I knew from her expression that I had just taken Jane to
a dark and wonderful place.



++



Although the physical and mental sensations of assfucking Jane were exquisite,
the nature of our relationship and the time limit on it encouraged me to be
ever more adventurous with her tasks.



The next incident worth recording was inspired by some idle chat while we had
been eating. Jane mentioned that her sister Anne had got into a new job. I had
only met Anne once, about a year back, and she had struck me then as almost the
other side of the coin to her sister- laid back, sexy, always fun. Oh, and
nineteen years old.



Later that same evening, Jane was tied to her bedposts, a slim vibrator buzzing
away in her asshole and clamps on her nipples. I had been teasing her for over
an hour already, and her skinny body was sheened with sweat. I knew that she
was turned on enough for anything. Anything? Well we would see.



"I bet Anne's a hot fuck," I whispered softly, my fingers making lazy
patterns around Jane's cute pubic thatch. I could feel her tense at the
unexpected turn the conversation had taken. "Quite a body too." Where
Jane was skinny and boyish, Anne was all voluptuous curves. "Wouldn't you
love to see Anne on all fours, Jane, those beautiful titties hanging down as I
fucked her from behind." I brushed Jane's clit. Still slick and throbbing.
"Maybe I'd titty-fuck her for a bit, she could do that, couldn't she, with
her beautiful titties?" There was no reply. "Couldn't she, Jane?"

 

"Mike, she's my little sister."



"Mm, but your clit gets wet at the thought of me fucking her."



"I know, but..."



"I could titty-fuck Anne, couldn't I Jane?"



"Yes." I could tell she was desperate not to respond erotically to
what I was doing, but the wetness of my fingers told me her body was betraying
her.



"Best of all though Jane would be to fuck Anne's ass. Wouldn't it? Just
imagine my cock sliding in and out of that tight little asshole." This
time a moan betrayed Jane's thoughts. I knew that in some ways she resented her
glamorous little sister, and I wondered if the thought of Anne's ass being
ravaged gave Jane some wicked satisfaction. "But I wouldn't just come in
her ass, Jane, would I? I'd pull out before I came, and then what would we make
her do?"



I could see Jane was in the finest dilemma, appalled at fantasizing about her
sister but also hugely turned on by it.



"I don't know."



"You could make her suck my cock out of her ass, couldn't you Jane?"



"Yes."



"Say it."



"I could make her suck your cock out of her ass."



"Make who?"



"Anne."



"Say it all."



Jane shook her head, weary and disgusted and desperate. "I could make Anne
suck your cock out of her ass." I touched her clit. "Please
don't." She was wetter than I had ever known.



I reached over to a dresser where Jane had some pictures, and rested one of
Anne in front of her face. "You want me to fuck Anne's ass?"



Jane nodded. She wanted it over.



"You want Anne to suck me after I've been in her asshole?" Another
nod. "Or maybe you want to suck my cock after it's been in Anne's
asshole?" As I was saying it I stroked Jane's clit quite deliberately, and
she exploded into the most unwilling but violent orgasm. After maybe twenty
seconds she began to stop twitching, but not before I'd heard her mutter
"Bastard".



++



The last night of our deal, we paid a quick visit to Anne's apartment, arranged
by Jane at my instruction. For a brief while Jane paid a visit to the bathroom,
through Anne's bedroom, while I chatted to Anne in the kitchen. Ten minutes later
we were on the way home, but we left with more than we brought.



"How many pairs did you get?" I asked.



"Three. She shouldn't notice they're gone."



"Used ones, from the laundry?"



"Yes. You sick bastard."



"Colors?"



"One white, one pale blue, one pink. Oh and the pink one's a thong. I
thought you'd like that." I did.



A little later Jane was once again tied to her bed, her asshole full of my
come, her nipples stiff with anticipation as she waited for her own release.



I reached to the side of the bed, and lifted up Anne's panties. "You
thought these were for me, didn't you?" I asked.



Jane stared blankly at her sister's underwear. Who else were they for, she
seemed to be thinking.



"But you see, little slut, it's you I'm always thinking of." I dropped
the panties on Jane's nipples, and she flinched as realization came.



"You fucking can't!" It was the most rebellious I'd seen her.



"I fucking can," I said, lifting the sky blue panties, turning them
inside out and then pressing the crotch against Jane's mouth. "Can you
smell your sister's cunt, Jane? Mm? I bet you can." I picked up the pink
thong, sought out the "tail" and draped it across Jane's nose.
"That's pretty much where it would have been tight up against Anne's asshole,
isn't it Jane?" I poked the final pair inside Jane's soaking cunt, and
focused on rearranging Anne's panties as Jane moved her face from side to side
trying to rid herself of the hateful items.



But it was an impossible struggle, and I pressed the ass of Anne's thong tight
against Jane's nose, the cunt of the panties into her mouth. "Smell Anne's
ass, Jane, taste her cunt, and come for me now."



There was nothing Jane could do, nothing, and she screamed the most sensational
obscenities as the smell and taste of her own sister's genitals gave her a
final, terrible, wonderful orgasm.



++



No of course we didn't stop after seven days.


++

Thanks for reading. If you liked my story, then please tell me what you think by emailing mikechamberswrites@hotmail.co.uk

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