She liked to use the nickname "Sky "and even though I
knew her real name, Sky is what I called her. She was
not a full-time prostitute although she did accept money
for her services on occasion. We had been introduced by
a friend of mine who knew about my sexual preferences
and had thought that Sky might be willing to give it a
try. That first meeting was two years ago and though we
only meet a few times in a year, I like to think that
our relationship involves more than just money.
I arranged to meet her for lunch and we spent a pleasant
couple of hours getting reacquainted. Sky always made
me feel as if we had never been apart and we were soon
chatting and laughing like old friends. Our
conversation soon moved on to matters sexual.
' I have thought of something new that you might like
to try ' said Sky with a mischievous grin.
' Something painful I hope ' I replied.
Sky pouted. ' I know that you can't wait to hurt me, you
horrible sadist ' she said, throwing a napkin at me.
I hesitated for a moment. I wanted to do something that
I knew would annoy her and her words gave me the opening
that I needed to bring it up.
' Actually I always worry that I will get carried away
and really hurt you, especially when it's been a long
time since I have had sex. That's why I want to do
something a little different this time ' I said.
' What's that? ' asked Sky suspiciously.
Taking a deep breath, I told her that I would like to
pick up another girl. Sky's face darkened and I
hastened to explain that I had no intention of having
sex with this girl and only wanted to work off some of
the sadistic tension that had built up within me.
Naturally, Sky objected, fearing a threat to our
relationship. She resisted as much as she could, but in
the end she agreed to go along with my plan, sensing
both my determination and my very real concern for her
We caught a taxi which I directed to a nearby piano bar
which I knew to be a good place to pick up the kind of
woman I was looking for. At first glance the place
looked like any other upscale singles bar, until you
noticed the unusually high proportion of attractive
female patrons. I selected a quiet booth towards the
back and ordered drinks, a beer for me and an orange
juice for Sky who didn't drink. I caught the eye of the
attractive dark haired woman seated at the bar and gave
her a nod. Anna was the "business manager "for the
working girls who were only available through
recommendation and after she had thoroughly checked the
client's background. This was not the first time that I
had come to her, so we got right down to business. I
told her that I wanted a girl who would be willing to
take a beating for the right fee, but not an S&M
professional. She frowned in concentration for a moment
and then pointed out several girls whom she thought
might be interested.
I took a sip of my beer and at the same time briefly
examined each of the girls that she had indicated.
Finally my eyes settled on a tall, slim, serious looking
girl. My instincts and many years of experience told me
that she might be interesting. I informed Anna of my
choice. Anna nodded and told me that the girl's name
was Natalie. She whispered a price in my ear and when I
agreed she got up and walked over to talk to Natalie.
Sky tapped me on the arm and said ' Let me talk to her '
. I agreed and when Natalie came over to our table I
indicated that she should sit next to Sky. Natalie
looked slightly surprised but obediently moved to slide
into the booth at the side away from me. The music
drowned out most of their conversation although I saw
Natalie glance speculatively at me several times as Sky
presumably explained my desires. After nearly five
minutes of whispered discussion Natalie looked up at me
and said ' O. K. ' . I looked at Sky who nodded and
said ' She can do it ' . There seemed to be nothing
else to say, so I settled the bill and the three of us
got into another taxi which took us back to my hotel.
There is always an awkward moment when you find yourself
sitting next to a woman whom you have never met before
even though you know that she has agreed to have sex
with you. In this case it was even more difficult
because I had no intention of getting intimate with her.
' Hello Natalie ' I said.
' Hello ' she replied, smiling.
I could see that she was a bit uncertain about what was
expected of her. I had made no attempt to hug or kiss
her and she did not know whether I would welcome any
approach on her part. I put my hand on her's and smiled
' I want to apologise if I seem unfriendly, but as you
can see I already have a companion for the night ' I
said, with a nod towards Sky. ' I know that she has
explained what I want, but I want to be sure that you
' You want to hit me ' said Natalie.
' That's right. I want to whip you here ' I said,
pointing between her legs. ' This is going to hurt. Are
you sure you're all right with this? Once we start I
won't pay you unless you finish the session '
Natalie replied that she understood and that she was
willing to continue. I had done my best to give her
fair warning, so I shrugged and asked her to undress.
She asked to go to the bathroom so I pointed the way and
sat down on the couch. In the meantime, Sky had been
pacing around in the bedroom, obviously still annoyed at
A few minutes later Natalie returned wearing nothing but
a large towel and showing an impressive length of leg.
I reached into my pocket and produced the short length
of flexible nylon tubing that I intended to use as a
whip. I showed this to Natalie, who eyed it
apprehensively. It was obvious that she had little or
no experience with such paraphernalia and was therefore
uncertain whether to be relieved or fearful. I
indicated with my fingers that she should remove the
towel which she did, spreading it over the seat of the
couch like a blanket. I took the opportunity to study
her naked body and was fairly pleased with what I saw.
She was slim but not to the point of emaciation, with
pleasantly firm breasts. She did not trim her pubic
hair, which was fairly sparse and straight, leaving her
labia clearly in view. She stood patiently allowing me
to enjoy the view, although her hands fluttered about
nervously betraying her desire to protect her modesty.
I smiled a silent "thank you "and indicated that she
should lie down. Her long sleek body was even more
impressive when stretched out on the couch and I could
not resist running the tips of my fingers up the length
of her thigh. I held up the whip and said ' Spread your
legs please ' .
It finally dawned on Natalie that I intended to use the
whip on her pussy. Despite all the explanations it had
never occurred to her that her sex could be used in such
a manner, and she must have assumed that she was to be
beaten on her thighs and buttocks. She pointed between
her legs and mimed a whipping motion, her eyes wide and
slightly frightened. I nodded solemnly in reply.
Natalie turned her head to look at Sky appealingly.
After a moment Sky sighed and went to kneel beside
' It's all right. Just do as he tells you and spread
your legs ' she said in a sympathetic tone.
' But I'm not sure if I can bear to let him hit me
there ' said Natalie.
' Look, you agreed to this. Why don't you try it first
and you might find that it's not as bad as you think '
Natalie gulped and then turned to me. She flashed two
fingers quickly, like a victory sign and said ' Can I
try two? '.
' Sure ' I replied. I tapped the inside of her knee
with my finger and she gingerly spread her thighs a
hands breath apart.
' Wider ' I said gently. Sky nodded in encouragement
and Natalie finally took the plunge and spread her legs
wide apart, placing one foot on the carpet. I slowly
moved the whip between her thighs, allowing it to brush
lightly across the bulge of her sex. Natalie clenched
her fists and lifted her head to watch. I lifted my
hand, took aim and hit her pussy twice in quick
' Ow! ' gasped Natalie. Her thighs closed and her
hands came up to cup her sex protectively. ' That really
hurt ' she said accusingly to Sky.
' Of course it did. That's the whole point isn't it '
replied Sky. ' But you're still alive and you're not
bleeding. I promised that he would not injure you, but
you did agree to let him hurt you in any way that he
liked didn't you? '
I knew from experience that it was much easier to face a
punishment that had a definite limit no matter how
painful, rather than an unspecified quantity, so I said
' Natalie, all you have to do is take 50 strokes between
your legs and it will be all over. You can then go home
with the money in your pocket ' .
' Fifty? ' squeaked Natalie.
' It's O.K. I've taken that many before ' said Sky
with a sly grin. She was clearly beginning to enjoy
herself at Natalie's expense.
Looking trapped, Natalie agreed. I told her that I
would let her determine the timing of each stroke. This
was actually a subtle cruelty as this meant that she
would have to order every stroke of her own punishment.
Sky glanced at me in amusement as she was familiar with
this tactic, having had it used on her many times.
Natalie gingerly spread her thighs again. She turned to
Sky and asked her to help keep count. Sky solemnly
promised to count every stroke. Natalie held up a
quivering finger. ' One ' she said, meaning one stroke.
Her hips bounced on the couch as the whip bit into the
soft skin of her pussy. A moment later her finger rose
again and my whip slapped into her crotch once more.
' Two ' said Sky. ' Forty-eight to go '
I gave Natalie a moment to feel the sting of the whip
and to contemplate the prospect of another forty-eight
strokes. I then said ' If you like I can offer you an
alternative. I will reduce the number of strokes to
twenty on the condition that you spread your pussy wide
apart and let me hit the inside of your sex. That means
that you have to expose your clit and the opening of
your vagina to the whip ' .
Sky nodded enthusiastically and said ' Take the offer.
Twenty is much better than fifty, even if it hurts a
little bit more ' . Naturally Sky knew that it had been
my intention all along to whip the inside of Natalie's
pussy, and that it was all part of the game to make the
victim actually grateful for the opportunity to have the
sensitive inner parts of her pussy whipped. Sky dashed
into the bathroom and returned with a small hand towel
which she handed to the bemused Natalie.
' Bite on this. It will help you bear the pain '
After Natalie had obediently placed the folded towel
between her teeth, Sky pointed at Natalie's pussy and
nodded at me to continue. As to be expected Natalie's
thighs had closed and I had to coax them apart once
more. Her knees trembled noticeably as she slowly and
reluctantly exposed her cunt. I made a spreading motion
with my fingers and said ' Now open this up for me
please ' , pointing at her crotch. Natalie reached one
hand down between her legs and gently peeled apart her
labia with the middle and index fingers. Of course
anyone who knows me or has read any of my previous
narratives will know that this was totally unacceptable
as the back of the hand and the fingers serve more to
protect rather than expose the target. I shook my head
and took hold of her free hand. I folded the fingers of
her hand to form a fist and then unfolded the index
finger, the tip of which I placed on her labia just
below the tip of her clitoris. Natalie quickly realised
what I wanted and duplicated the move with her other
hand. Unfortunately she then made an exceedingly timid
effort at spreading open her sex, revealing little more
Sky sighed in exasperation and leaned forward to whisper
into Natalie's ear. After a moment Natalie's fingers
began to move, presumably in response to Sky's
instructions, first moving apart to either side until
the inner labia were taut and clearly exposed. More
whispers followed and Natalie's fingers slowly moved
upwards in the direction of her chest. This slight
adjustment served to peel the protective hood of skin
back from her clitoris, ensuring that it was fully
exposed to my whip. It was obvious that Sky was
determined that Natalie should earn every cent of her
fee. I smiled and raised an eyebrow at Sky, who looked
back at me innocently and pointed at Natalie's pussy.
However before I could start, Sky decided to add one
' Take my advice and let him hit you in batches of five
strokes at a time. That way it will be all over much
more quickly ' urged Sky earnestly. Natalie's eyes open
wide and she mumbled "Five?" around the towel that was
still gripped between her teeth. Sky nodded firmly and
then turned to me and said "Five".
I turned my attention back to Natalie's pussy. The
touch of her manipulating fingers combined with her
excitement and fear had brought her inner labia to a
stiff and throbbing state of erection. They provided an
irresistible target and without further hesitation I
brought the whip cracking down five times in quick
succession. I had aimed the tip of the whip at the
inviting, moist opening of her vagina and each of the
strokes had expended their venom along the inner length
of the labia or the stretch of moist tissue between
Natalie's urethra and vaginal mouth.
Natalie uttered a soft, high pitched scream, which was
discreetly muffled by the towel clenched between her
teeth. She cupped her hands protectively over her
wounded sex as she writhed and bounced on the couch.
' Only four more ' said Sky encouragingly. From where
I stood I could see her eyes gleaming mischievously.
After a moment Natalie reached up and removed the towel
from her mouth and signaled for Sky to come closer.
There was another whispered conversation and then the
towel went back between her teeth.
' Open her up yourself ' said Sky. She explained that
Natalie could not bear to hold her own sex open to be
whipped, even though she was willing to let me do it. I
was in two minds about this development. On one hand it
meant that I would have to use the one-handed spread
which I disliked, but on the other hand it gave me an
excuse to touch and play with Natalie's pussy.
I moved slightly closer to Natalie's hips and turned my
body towards her feet. Her thighs trembled visibly as
she spread them apart once more. I bent over and slid my
fingers into the crevice of her cunt, moving them over
and around the moist crinkled flesh of her labia. I
pressed down hard and spread her sex lips as wide as I
could and pulled the skin between my fingers taut.
Since the angle was not ideal I took special care to aim
the whip by resting the last three centimeters over the
spot where her labia met, making her clitoris the
primary target. I raised the whip and brought it down
sharply. The flexible black nylon cracked against her
cunt flesh with commendable accuracy and I heard Sky
count "one " as I raised the whip for the next stroke.
Being freed from the necessity of pausing between
strokes, I could fully enjoy the feel of Natalie's pussy
under my hand, the sharp satisfying feeling of the whip
striking home and the vision of her clit and labia
straining upwards to meet their tormentor.
The last ten strokes passed in a sensual blur and I had
to restrain myself from hitting Natalie just one more
time. I am sure that she would have agreed, albeit
reluctantly, if I had insisted on a few more strokes.
However I am a man of my word and Natalie had actually
done very well, so I dropped the whip and thanked her
for her efforts. Natalie smiled and hurried thankfully
to the bathroom to get dressed. A moment later she
reappeared fully dressed and I handed her the agreed
fee. Sky accompanied Natalie to the door and I heard
them exchange words before she left.
' She asked me to tell you that she would be willing to
come back again so long as you did not hit her any
harder than today ' said Sky with a grin.
' It's surprising how many women seem to be able to
accept the idea of having their pussies beaten once they
get over the initial fear '
' It still hurts though '
I grinned. ' I believe that's the whole idea '
' Horrible sadist ' said Sky, sticking her tongue out
I went into the bedroom where I undressed. ' I'm going
to take a shower. Join me '. I held out my hand and
waited. I knew that Sky was still upset, but she was
not my girlfriend or my wife and it was up to her to
adapt. After a long moment she reached out and took my
hand and we walked into the bathroom together. The
relaxing spray of hot water and the comforting ritual of
the bath help to restore a feeling of intimacy between
us. By the time we had toweled ourselves dry and slipped
under the sheets, we were giggling and touching each
other like newlyweds. The brief session with Natalie
had eased some of the accumulated tension but at the
same time had got my juices flowing. After the
appetizer I was now ready for the main course.
I dimmed the lights a little bit and joined Sky under
the sheets. I gathered her in my arms and kissed her
gently on the forehead. The feel of her warm naked body
moving against mine and the touch of her silky skin
under my fingers made me sigh with contentment. As
always, I felt obliged to ask. ' Are you sure? ' . Sky
pressed her lips against mine as if to silence my
' Don't worry darling. Just do what ever you want. I
will tell you if it hurts too much '
My fingertips had found their way to her nipple and I
gently stroked over and around it until I felt it
stiffen and rise under my touch. Then I gently gripped
it between finger and thumb. I looked into her eyes and
waited. Sky gave a tiny smile and nodded her head
quickly. I watched her face as my fingers gradually
tightened, applying more and more pressure until a sharp
intake of breath let me know that she was starting to
feel real pain. I continued to squeeze and I felt her
nipple flatten under my grip. In response, Sky's hand
reached over and her fingers wrapped themselves around
my shaft and began to softly slide up and down. I
increased the pressure even more, crushing her flesh so
hard that I feared that I might injure her, but still
she remained silent and in the end it was I who decided
to stop. I kissed her nipple and then her cheek. Even
though she was being paid to accept the mistreatment, I
felt that it was only right that I should demonstrate my
appreciation of her sacrifice and strength of will.
I drew her closer to me and stroked my hand down the
front of her body. Sky is very ticklish so I carefully
avoided her armpit and sides. I slid my hand up and
over the curve of her hip and down the side of her thigh
before bringing it around and up to cup the bulge of her
pussy. The tip of my finger dipped into a small slick
puddle and she giggled with embarrassment. Despite the
fact that she was in no way a masochist, her pussy
always seemed to be wet and welcoming to the touch even
after I had hurt her. I moved my finger carefully
between her labia and pushed it into her hole. As usual
her strong vaginal muscles squeezed down hard in
reaction to the intrusion and it required a fair amount
of effort to get my finger inside her up to the second
' My favorite virgin ' I quipped.
' Once upon a time maybe ' replied Sky with a soft
I jabbed my finger into her harder, deliberately rough.
Sky twitched slightly but made no objection to my
digital ****. After I had thoroughly explored her
vagina I withdrew my finger and let my palm rest on her
pussy. Sky knew me well enough to anticipate what came
next and she lifted her upper thigh so as to give me
more room to work. I smoothed my palm over the hair
covered bulge of her cunt, mentally mapping her sexual
terrain under the blankets. Sky stroked her fingers
down my arm and across my chest, silently letting me
know that she was comfortable with what I was doing and
what I was about to do.
' It's funny '
' What's funny? ' I responded, still preoccupied with
the feel of her sexual flesh under my hand.
' It still hurts the same when you do these things to
me, but somehow I think that I am kind of getting used
to it and it almost seems natural now. I get really
horny when you touch me like this and when you hurt me
it doesn't make the good feelings go away. Maybe I am
becoming a masochist? '
' Do you like being hurt by other people? '
Sky shook her head emphatically. ' No way '
' Then it must be love ' I said with a smile.
Sky giggled softly. ' Do it ' she said, giving me a peck
on the lips.
I shifted slightly to brace myself and then slapped her
hard between her legs. Sky quivered as the muffled '
smack ' filtered through the blankets. Her thighs
closed, trapping my hand in a velvet vice for a second
before opening again. She twitched her hips, rubbing
her pussy against my palm as I kissed her.
The blankets rippled like a sheet of storm tossed water
as I slapped her pussy again and again, savouring the
feel of her cunt against my palm and the subtle tensing
and movements of her body in reaction to each blow.
' Tell me how that feels. Where does that hurt the
' Well, it hurts my pussy of course, all over, but not
just on the outside. When you hit me like that I feel
it all the way inside here ' she replied, pulling my
hand to touch her belly midway between her belly button
and her pussy.
This revelation raised a concern in my mind that I could
be causing her an internal injury. But when I raised the
possibility Sky quickly reassured me that she was not
being seriously hurt. ' It's sort of like the muscles of
my tummy cramp up ' she explained. ' I told you not to
worry. I will tell you if I am having problems. Just
enjoy yourself '
Despite her assurances I decided not to spank her any
more. Of course this did not mean that I was going to
stop hurting her pussy. ' I want to play with your clit
for a while ' I whispered. ' Spread open the top of your
pussy so that your clit sticks out '
I felt her hands move down between her legs. Her
fingertips traced the edges of her labia, and for a
moment it felt as if she was masturbating as she
manipulated her own flesh in order to expose her
clitoris in the manner that I had requested. Her hands
stopped moving and she gave me a tiny nod. ' O.K '
Using her fingers as a guide I carefully slid my fingers
into position around her helplessly exposed clit. Very
gently I traced the tip of my finger around her delicate
little bud, enjoying the porcelain smooth feel of her
skin and the knowledge that my touch was sending
electrical sparks of sensation shooting through the
tightly packed nerves that filled her unlubricated clit.
I sensed Sky's toes move as she clenched and unclenched
them in reaction.
' That tickles '
' You mean this? ' I asked innocently, circling her
' Yes ' she gasped. ' It makes me want to pee '
Mercilessly I continued to tickle her clit until Sky
shivered and begged me to stop. ' Please do something
else. This is worse than any torture or whipping.
You're killing me ' she gasped.
I stopped tickling her clit and Sky sighed with relief.
' I'm going to hurt you now ' I said, taking hold of her
clit between finger and thumb. ' I want you to tell me
when to stop. All you have to do is to stop kissing me
' . I kissed her lips and then pulled back in
demonstration. ' Do you understand? '
Sky nodded and pressed her lips against mine. After a
brief moment of fumbling I managed to get a good grip on
her clit and I began to squeeze, steadily increasing the
pressure of my fingers like the closing jaws of a vice.
I felt her muscles tense as the pain grew in intensity
and her lips pressed even harder against mine. Soon her
clit had flattened under the crushing f***e of my grip
and I knew that she must be feeling intense agony, but
she stubbornly clung on to our kiss as if content to let
me rip her clitoris from her body. The intimate torture
seemed to flow like a current from her clit to her lips
to mine and down to my fingers, filling all of my senses
with the touch, taste, smell and feel of her pain. In
the end, it was I who ended the torture for fear of
injuring her. I pulled my head back and looked into her
eyes. She never failed to amaze me with her fortitude
and determination. I kissed her forehead and whispered
' Thank you ' . She smiled and lightly stroked my
swollen cock as if to tell me that she understood the
pleasure that she had just given me.
Sky threw her thigh over my hip and wrapped her arms
around me. We cuddled and played, and I thrust the tip
of my cock through her pubic hair in a parody of
fucking. Sky played along, moaning and gasping as if I
were actually plunging into her vagina. I threw the
blankets aside and kissed my way down her body. I
licked her breasts and nipples, her belly button, her
inner thighs and finally her clit. The last drew loud
squeals from Sky who always found cunnilingus more
ticklish than pleasurable. After she had convinced me
to stop my lingual activities, Sky reached into the
drawer at her side of the bed. She turned back to me
and said ' I have a gift for you ' .
' What's that? '
' I had an idea. A new way for you to hurt my pussy '
' Oh? '
Sky held up a small, slim brown rubber band, the size
that would fit comfortably around a rolled up magazine.
' I remembered how these used to sting in school and I
thought that you might like to try it '
I was both touched and excited by the thought that she
had actually devised a new pussy torture for me to use
on her. I took the rubber band from her hand and
stretched it thoughtfully between my fingers. Then I
placed it against my inner thigh, looped around my
finger and thumb. With the other hand I pulled one
strand taut, stretching it about two inches above the
surface of my thigh . When released, the elastic strand
snapped against my skin with a satisfying ' crack ' . I
examined my skin and found a clear red mark under the
rubber band. I turned to see Sky watching me intently .
She grimaced theatrically and said ' Maybe it wasn't
such a good idea after all ' . I kissed her hand and
told her that I thought it was a wonderful idea, and
then I set it aside for later use .
I was getting tired from leaning over her, so I decided
that a change of pace was in order . Lying down on my
back, I asked Sky to climb on top with her knees to
either side of my head and facing my feet . I told her
that I wanted to just play around with her pussy for a
while and for her to suck me while I was doing so . For
the next 10 minutes I pulled and stretched and twisted
her pussy lips while her mouth and tongue gently worked
on the head and shaft of my cock. One of the things that
I loved about Sky was her patience and willingness to
humour my fascination with her pussy . I told her to
stop when I felt that she was tiring and she dropped
back on to the bed with a sigh of relief . Fellatio was
not one of her favorite activities and it had taken me
quite a while before she could be convinced to let me
cum in her mouth . At first she would only let me cum on
her closed lips and on her face; but when I accidentally
squirted my semen up her nose she finally agreed that
she might as well let me ejaculate into her mouth .
' I would like to whip your cunt a few times '
' I thought that you had gotten enough of that with
' But only you know how to do it properly . I just want
to hit you a few times hard '
Sky spread her legs . ' I don't know how many hard ones
that I can take . You'll stop if I tell you won't you? '
' Of course . Just give the word and I'll stop '
Using both hands, Sky spread her outer pussy lips wide
apart, stretching the pink and red insides of her cunt
taut, opening her sex totally to my whip . I planted a
gentle kiss on the centre of her wide spread pussy and
then brought the whip whistling down . Sky groaned
softly and her legs kicked out as if to ward away the
burning pain. I placed my hand on her inner thigh to
steady her hips and swung the whip again, slashing its
short, flexible length diagonally across her labia .
This time her legs clamped together and she rolled onto
her side moaning in pain . She shook her head . ' I'm
sorry, I can't take any more like that ' she apologised
' Nonsense. You did wonderfully ' I said, cuddling her
in my arms . She sighed happily and said shyly ' Please
make love to me now '
' Are you sure that you are O.K.? ' I asked, touching
her pussy . She nodded and spread her legs in welcome.
I was not ready to cum yet, but I knew that Sky could
only achieve an orgasm by being fucked hard . No amount
of licking, sucking or fingering could bring her off . I
was fairly good at eating pussy and usually had no
problem in giving my partner an orgasm or two with my
tongue, but Sky only screamed with laughter when I went
down on her . I knelt down between her wide spread
thighs and placed the tip of my cock into position. Her
warm soft labia wrapped themselves around my shaft in a
gentle embrace as I slowly sank into the slippery moist
depths of her cunt hole . Her vaginal muscles vigorously
resisted my penetration, and it almost seemed like I was
taking her maidenhead. In my mind I re-created the image
of her widespread cunt quivering under my whip, and this
added extra stiffness to my member as, very slowly, I
eased my way into her body . Finally, after what felt
like an hour of pushing and twisting, I felt her
buttocks and pubic hair press against my groin . I put
my hands under her knees and lifted her legs up on to my
shoulders. Using short even strokes I began to fuck her
. Skin slid it against skin as her thighs rubbed against
my torso and the slick inner walls of her vagina rubbed
against the tautly stretched skin of my cock . The scent
of her filled my senses . The smell of her skin merged
with the scents of her hair, her sweat and her cunt to
form a perfume that was unmistakably woman . I leaned
forward and braced myself with an arm to either side of
her head. Sky's hands grabbed my wrists as I started to
pump harder in and out of her hole . The bed and
mattress began to squeak and groan in time with the
bouncing of our joined bodies . Sky closed her eyes and
turned her head to one side as if to deny her
participation in this primal act, but she was unable to
resist the mind numbing waves of sensation that emanated
from her pussy . She gritted her teeth as if suffering a
pain greater than any that my whip had ever inflicted on
her . Her gasps and moans could easily have been
interpreted as being the result of incredible agony
instead of overwhelming pleasure . I thrust even harder
and even faster, virtually pounding my hips into her
buttocks. Sky pressed her lips against my forearm and,
vampire like, started to suck on my skin and I knew that
I would have a mark there that would last several days .
I felt her body vibrate as the flames of orgasm raced
through her nerves, but I did not slow down and in
moments she came again. The tendons in her neck
tightened into steel cables and her head shook rapidly
from side to side . She slapped her palms against my
shoulders as she gasped for me to stop .
' Enough '
' Are you sure ' I panted.
' Yes, yes, please stop ' she pleaded.
I carefully slid my slime covered cock out of her sheath
and flopped down on to the bed beside her.
Sky knew me well enough not to be surprised at the fact
that I had not come inside her pussy. She put her hand
on mine and gave it a squeeze . ' Give me a moment and I
will take care of this ' she said, with a nod towards my
still rigid cock . ' I came twice you know . I'm all
' Enjoy yourself? '
She pouted and wriggled on the bed . ' You know that I
don't like to talk about it. I'm very shy and modest
you know ' she said as she spread her legs wide to show
me her moist and swollen pussy .
' Oh yes, shy . That describes you perfectly ' I
replied solemnly .
' Come here ' she said, crooking her finger at me . I
took that to mean that she had sufficiently recovered
from her orgasmic exertions and climbed across the bed
to kneel astride her chest . I felt her stiff nipples
press into my buttocks as I lowered my cock to her mouth
. She took hold of it gently and began to lick the
underside of the glans with the flickering tip of her
tongue . I sighed in contentment as she licked and
kissed my cock . Sky looked up at me with a raised
' You still haven't used my gift '
I nodded in agreement . ' I think that it's about time
that we try it out ' . I reached out and picked up the
small rubber band . Then I scooted down the bed until my
head was just below her pussy .
' Open up '
Once again Sky spread her labia apart with her fingers
and I gazed upon my favorite plaything .
' Hmm, let me see how we are going to do this ' I
muttered as I studied the rubber band . Finally I
decided to loop the elastic band over the finger and
thumb of my left hand . Then I used those same digits to
spread apart the opening of her vagina, which had the
effect of stretching the rubber band across the wet pink
' How many do you want? ' asked Sky .
I thought for a moment. Since this was something new, I
was not sure how much damage I would be causing, so I
decided to be generous . ' How about two in the hole and
two on your clit '
' O.K. I'll try my best '
Using my other hand I lifted one of the strands that
bisected the mouth of her cunt, stretching it about
three inches above her flesh . I took careful aim and
then released it . The elastic whipped down to strike
her pussy with a sharp ' snap ' and I felt Sky's body
jump . I heard a sudden intake of breath and I saw her
fingers claw into the blankets, her knuckles going white
' Are you all right? '
' Just do the other one ' she gasped.
With exquisite care I took aim and whipped her cunt hole
again with the rubber band . This time I removed my hand
and Sky immediately rolled onto her side in a fetal
position with her hands pressed tightly against her
tortured cunt . I stroked her back, and soothed her
until I felt her relax.
' Let me see '
Obediently she spread her legs. I peeled her labia
apart and leaned close to examine the damage . I was
intrigued to see a dark red horizontal line swelling up
from the inner surfaces of her labia to either side of
her vaginal opening . It was obvious that most of the
f***e of the striking elastic band had been expended on
her labia rather than on the opening of her hole as I
had intended . I gently kissed the wounded areas and
then moved up to lie beside her . I drew her into my
arms and hugged her for a while . I kissed her lips and
face and told her how brave and wonderful she was .
I told her what I had seen between her legs . ' The next
time I do that I shall have to try a different position
for the rubber band . I really want to try and hurt you
right inside the hole ' . Once again, Sky displayed the
amazing ability to discuss her own torture objectively
as if it were another woman's pussy that I was planning
' Maybe you can just loop the rubber band over the tip
of one finger as if you were trying to shoot it had to
me and then push your fingertip into the hole '
' Yes . That might work . I have this obsession with
hurting the inside of your vagina . I imagine putting
something like a toothbrush inside and scratching you
with it or something like that '
' That sounds good . If you had long fingernails you
could put them inside and scratch me that way . All the
bruises and red marks would be inside and your cock
would rub against them when you make love to me '
I was amazed that she understood and even agreed . ' Yes
. Just imagine . You would be smooth and perfect outside
and only have the marks of my torture deep inside your
cunt . No one could tell by looking at you that anything
had been done to you at all '
She nodded enthusiastically . ' Yes, I like that idea .
Hey, if the toothbrush had a hole at the end of it's
handle you could attach the rubber band to it and push
it inside me . Then if I open up the hole really wide
with my fingers you could snap the rubber band against
the inside parts of my vagina '
All this talk had brought my cock to full attention and
Sky noticed my condition with amusement . ' Would you
like to do my clit now? ' she said, giving my cock a
prod with her finger .
' How about one now and one when I'm ready to come? '
' Sure '
' O.K, get your clit ready '
' Is this all right? '
' Move your fingers a little higher and further apart.
That's good, keep it sticking out just like that '
I stretched the rubber band across her pussy once again,
but this time with one of the strands carefully placed
over her clit . With the hood of her clitoris peeled
well back and the lips of her pussy tightly stretched
apart by both her fingers and mine, there was nothing to
prevent the full f***e of the catapulting elastic from
inflicting itself on her tiny sex bud . I took a grip on
the centre of the rubber band and pulled it up and away
from her body like an archer drawing on a tiny bow . '
Get ready ' I warned her . I focused my eyes on her
unsuspecting clit and paused to savor the moment.
Images, sounds and words flashed through my mind .
' Don't touch me there, it's very sensitive ' chorused
a multitude of women .
' The clitoris is extremely sensitive and should not be
touched with an unlubricated finger . . . '
' Only another woman really knows how to treat a
woman's clitoris ... '
I gave the imaginary crowd of sex counselors, authors,
women's magazines editors and hookers a mental finger .
After taking precise name, I released the taut elastic,
which struck squarely across Sky's clit with a sharp '
whap ' . This was followed by a short, high pitched
scream which she quickly muffled by covering her face
with a pillow . I pressed my arms across her thighs to
hold her bucking, twisting body on the bed and then
quickly climbed up to sit astride her chest . Once I was
in position, I began to slide my hand up and down the
length of my cock, all the while rubbing the tip over
her face and lips . Her tongue lapped at my cock as it
passed over her mouth and her hands ran caressingly over
my thighs and buttocks, urging me on . The warm breath
from her nostrils tickled my cock as I felt my orgasm
' I'm nearly there ' I gasped .
Sky picked up the rubber band from the bed and handed it
to me as I scrambled down to sit astride her thigh .
This time Sky spread her pussy with the fingers of one
hand while she used the other to keep my cock at the
brink of orgasm . I applied the rubber band to her
reddened and swollen clit, and without ceremony,
tortured it one last time . The sound of the rubber
striking her flesh coupled with the tightening of her
grip around my cock was sufficient to bring on my climax
. In a second I was astride her chest once more . Sky
placed her hands on my buttocks and lifted her head so
that I could place the very tip of my cock between her
lips . Moments later my cum spurted again and again into
her waiting mouth . She sucked gently at the tip,
patiently waiting for every last drop of sperm to flow
on to her tongue before using its tip to clean off the
last traces of fluid seeping from my glans . When the
final spasm had come and gone, I carefully climbed off
of her and dropped bonelessly onto the bed .
Sky smiled at me . ' Was that O.K? ' she asked .
Drained and contented, I slid my arm under her head and
kissed her forehead and her lips .
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