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First Anal off a Street Corner

7/16/2010

...............................................
It was dark. It was raining. I was tired.


I was also nervous. I considered calling the whole thing
off, but it was too late now.


She was waiting.


I peered through the rain spattered windshield, between
the squeaking wipers in a vain attempt to make out the names
written on the overhead street signs.


"I really should get some glasses, " I muttered
to myself as my eyes squinted to see through the driving
rain.


This was the first time I would be meeting a girl off the internet.
And although we had been exchanging emails regularly and
even talked on the phone a few times, I was more than a little
surprised when she called me earlier that evening, asking
me to pick her up. Of course, a sex invite is a difficult thing
to pass up, even if I was tired.


My car rolled along cautiously as I scanned the sidewalks
for any sign of her. I glanced at my watch. I was late. Maybe
she had become tired of waiting and left? I think deep down
inside that's what I was hoping for. I looked at my cell
phone.


No messages.


I was about to turn down a side street and head home when I
saw her.


She exactly as she had described. Purple coat. Black Boots.
Standing on the corner of Georgia and 4th.


As I pulled the car over to the side, I began to feel a bit creepy.
I'm sure any bystanders would be thinking I was picking
up a hooker. As I rolled down the window, she took a few tentative
steps towards me, huddling under a large, black umbrella.



"Damon?" she called out through the sounds
of the falling rain.


"Hi, " I answered back with a smile. It was imperative
to smile. I don't want to scare her off now.


With no further hesitation, she hurried towards the car,
her high heeled black boots clacking against the wet pavement.
She seemed awkward and uncomfortable, as if she was not
used to wearing such footwear.


"Sorry I'm late, " I apologized as she
opened the passenger door. "I had a hard time finding
the right street.


"Oh that's okay, " she answered as she
folded her umbrella and climbed into the seat.


With a close of the door we were soon on our way back to my apartment.



"So, " she began, looking over at me with a smile.
"We finally meet."


I nodded. I was checking her out, without trying to be obvious.
She was tall for an Asian girl, standing somewhere around
5'10. With her boots on she most likely cleared 6 feet
easily. She wasn't as attractive as her pictures had
made her seem but that was to be expected. She probably felt
the same way about me.


Her tall black boots, slick with moisture from the rain
came up to her knees, giving way to a pair of black stockings
that ended at mid thigh. I was immediately turned on.


Although her long, purple coat hung down well below her
waist, I could tell she was wearing a very small skirt. From
the glimpses I could catch it appeared to be purple as well,
although a different shade. Her black hair was tied back
neatly, allowing me a clear view of her round, cute face
of which her pouty, pink lips were the most recognizable
feature.


Her name was Michelle.


"So am I what you expected?" she asked, with
a smile.


My eyes scanned her from head to toe, before I answered.



"My expectations have been exceeded, " I fibbed.



Michelle let out a soft giggle.


It only took about 30 seconds for the topic of conversation
to turn to sex.


"So how long has it been since you last got laid?"
she asked, swiping a long strand of dark hair from her eyes.



I furrowed my brow in contemplation as I thought about the
question.


"About two weeks, I guess. Why?"


"Just wondering, " Michelle spoke softly
as she turned her head to look out the window.


A few seconds of silence followed before I spoke again.



"How long has it been for you?" I asked.


"Honestly?"


"Yeah."


"About thirty minutes."


I turned my head in surprise.


"Are you serious?"


Michelle nodded, an embarrassed smile spreading across
her face. I immediately felt a rush of blood to my dick.


"You little slut, " I said with a laugh. "And
one guy wasn't enough for you?"


"Nope, " she countered back with a satisfied
grin. "After he fucked me, all I could think about
was calling you."


"You know..." I began. "You could have
called me before you fucked him."


"Does it bother you?" Michelle asked, a bit
of shame starting to show on her face.


"Not at all actually, " I answered back, assuaging
any fears she may have had of me thinking negatively of her.



Twenty minutes of awkward small talk later, we arrived
at my apartment. I parked the car and we headed inside, rushing
to avoid the falling rain. As I opened my apartment door,
Michelle strode in without any sign of discomfort.


"Wow, this is small, " she exclaimed, bending
down to unzip her large black boots.


"Yeah, " I concurred, tossing my keys on the
table.


Michelle strode across the room and made herself at home
by sitting on the small black couch as she pulled off her
coat.


"Can I get you anything to drink?" I offered,
my eyes drawn to her stocking clad legs.


"Water's fine."


I handed her a bottle of water before fixing myself something
stronger. I felt like a little bit of vodka would be useful
in overcoming my inhibitions. In fact, I was a little unsure
about how to proceed. Should I make small talk first? Or
was she expecting to just get right to it?


After a moment of contemplation I decided on a tactic that
might ease the night along.


"How about I put on a porn?"


Michelle smiled and nodded enthusiastically. I knew from
our various emails and chats that she was a big fan of dirty
movies.


"Any requests?" I asked, sitting down at my
computer.


"Just something you think I'll like."



"Wow, " I said, tossing my hands up in jest.
"That's helpful."


Michelle giggled as she took a sip of water


"Ok, " I reiterated. "Do you want something
really dirty...or something a little more...vanilla."



"Dirty!" she beamed. "As long as it has
anal in it."


I smiled. Although Michelle had never tried anal sex before,
she had shown great interest in the subject during our many
conversations.


"No problem, " I responded, browsing through
the various porn titles on my computer. "I think every
movie I have on here has anal in it."


After choosing an appropriate title I started the movie
on my computer which fed into the big screen TV in the corner
of the room. As the images came into view I climbed onto my
bed while Michelle remained seated on the couch.


"Aren't you going to sit beside me?" she
asked, patting the place beside her.


"Actually, I'd rather you came over here, "
I answered back, sipping at my drink. "The bed is much
more comfortable."


Immediately, she stood up and walked over to sit on the edge
of the bed.


"Wow, " she exclaimed, sinking down onto the
soft mattress. "This is really, really soft!"



I nodded in agreement as Michelle climbed onto the bed,
lying on her stomach facing the TV with her head resting
in her hands like a small child watching Saturday morning
cartoons. As we continued to watch, I found my eyes torn
between the pornographic images on the TV screen and Michelle.
With the way she was lying, her skirt was riding high up her
legs giving me a view of her cute little ass being cupped
by a pair of little yellow cotton panties. The panties were
riding quite high as well, clinging to the area between
her perfectly round cheeks, and then giving way to symmetrical
areas of smooth looking skin that formed a crease, separating
her legs and ass. I could also see the tops of her black stockings,
which were beginning to cause a tingle in my pants as my dick
slowly began to come to life.


Was she teasing me? She seemed to be completely transfixed
on the movie, totally unaware of the view was having on me.
It was time. I gulped down the rest of my drink and set the
glass on the bedside table. I then crawled down the bed head-first,
moving closer and closer to my ultimate destination. My
had touched the soft fabric of her stockings as I lowered
my head and pressed my lips against the back of her thigh.



"Hehe, " Michelle giggled, glancing back
over her shoulder. "I knew you wouldn't be able
to resist for long."


"Oh yeah?" I returned, flicking my tongue out
to lick at her inner thigh. "Is that what you were trying
to do? Tease me?"


"Ummm, more like...entice you."


"Well, consider me 'enticed.'"


With that I continued exploring Michelle's backside
as she spread her legs a little farther apart. My lips kissed
their way up the back of her legs as I pushed her skirt up a
little farther. I could hear her let out subtle moans as
my tongue teased her by flickering along the crease between
her butt cheek and leg. My hand caressed her smooth, round
ass, running gently over her bare skin and panty covered
cleft. I gave her taut cheek a squeeze as I kissed my way along.
My busy hand then moved to her other cheek giving it a short,
slow squeeze before tucking my fingers under the elastic
band of her underwear and pulling them aside. The tight
fabric stretched easily, slowly uncovering her tiny asshole
to my prying eyes. My lips followed, trailing a route directly
between her firm cheeks before parting and allowing my
tongue to lash out at her exposed hole.


"Mmmmm, " she purred, feeling my hot, wet tongue
gliding over her virgin hole. "You have no idea how
long I've waited for that."


I responded to her admiration by pulling her panties farther
and nestling my face in between her cheeks, planting a long,
loving kiss on her tight little star. Again she moaned and
again I was encouraged as I stabbed my tongue out, poking
and prodding the tiny smooth opening with growing lust.



"I want to sit on your face, " she blurted out
unexpectedly.


"Uhhhh, " I stammered, removing my face from
her ass. "Sure."


Without so much as a word, I obediently laid back on the bed,
as Michelle rolled over and began to remove her underwear.
My heart was beating with anticipation as she crawled over
to me, smiling. As she came closer, she pulled her skirt
up around her hips unveiling a pussy completely free of
hair, with the exception of a small leaf-shaped patch above
her crotch. With a single, smooth movement, Michelle swung
a leg over my head and lowered her pussy down onto my mouth.
She wiggled her hips a little as her soft pussy lips came
into contact with my mouth. Immediately, my tongue shot
out, parting her soft folds and burying itself in her wet
hole.


I moaned in enjoyment as I tasted her, my lips sucking her
pussy as my tongue wiggled its way inside her. She reached
down and grabbed lustfully at my hair, her hips rocking
slowly as she began to grind herself into my face. My hands
grasped her ass cheeks firmly as I tried my best to shove
my tongue as far as possible inside her.


Suddenly, she lifted herself off my face as I stared up at
her with curiosity. Without a word, Michelle reversed
her position so that she was now facing my feet. She moved
her body down a bit before reaching back, pulling her ass
cheeks apart and lowering her exposed asshole down onto
my waiting mouth.


I moaned in approval at Michelle's lewd act as my lips
once again came in contact with her perfectly smooth butthole.
My tongue again shot out, this time dancing around the puckered
opening, teasing her with quick, wet licks.


"Mmmm, " she moaned, leaning forward and causing
me to lift my head in order to keep my warm tongue in contact
with her asshole.


Then I felt her hands on my pants. My breathing quickened,
as Michelle popped open the buttons on my jeans and slid
the zipper down. Her hand slipped into my pants, cupping
my straining cock outside my underwear, giving it intermittent
squeezes as if testing it for size and firmness. My tongue
continued lashing at her butt while she started pushing
both my jeans and underwear down over my hips. I lifted my
ass in assistance and Michelle finally freed my throbbing
dick which sprang forth to come slapping against my stomach.
Her delicate fingers found their way to my shaft, wrapping
around it and lifting it to point upwards.


"Mmmmm, Damon!" she exclaimed. "You
have a very nice dick!"


"Thanks, "I responded in between licks of her
pussy and asshole.


After giving it a few slow strokes, Michelle leaned forward
and sucked the head into her mouth. I could feel her tongue
ring circling the tip as she sucked softly, coating it with
wet, warm saliva. Gradually, she worked her lips all the
way down my shaft, taking more of my cock into her hungry
mouth.


"Suck my clit, " she ordered firmly, settling
down into a stable 69 position.


I responded obediently, sucking her tiny, fleshy button
into my mouth as Michelle slipped my dick into hers. I locked
my lips around her clit, suckling it as she moaned around
my cock. Her hand soon found its way to my balls, which were
soon being gently squeezed and caressed as her lips slid
up and down my shaft. Her ass cheeks were being pried apart
by my eager hands as I continued working on her clit with
adamant diligence. I could feel her tongue-ring running
along my dick when she reached back and guided one of my hands
to her asshole. Michelle moaned again as my fingertip touched
her sensitive ring, wet from my tongue, and slipped easily
inside. Her tight little butt clenched around my knuckle
and she gave my balls a particularly forceful squeeze.
I started pushing my finger in and out as I sucked her clit
causing her to respond by taking my cock deep into her throat.



"Uuuugggghhhhhh, " she groaned in an unintelligible,
high-pitched squeal as she pushed herself back onto my
face.


My hand became trapped between her ass and my face, and I
was forced to withdraw my finger from its tight little prison.
Michelle's body began to shake and she pushed back
even farther, completely cutting off my air supply. I struggled
to take a breath, but her pussy was covering my mouth completely.
Squealed once more, before the strange sound soon gave
way to a relaxed contented sigh and she moved her ass down
my face, allowing me to breathe once again.


"Mmmmm, " she moaned with satisfaction as
she began gliding her asshole across my lips. "That
was nice."


My tongue once again shot out, stabbing her tiny orifice
with perverse enthusiasm, as she slowly stoked her hand
along my aching cock. She even pushed her ass back against
my face in an effort to receive more of my hot, wet tongue
into her insatiable asshole.


"I want you to fuck me so bad, " she spoke softly
but firmly in between licks of my cock.


"MmmmmHmmmm, " I responded in agreement,
moaning into her ass. "I want to fuck you so bad."



"How do you want me?" Michelle asked, pulling
her backside away from my busy tongue.


"Get on your hands and knees, " I stated simply,
more as an order than a suggestion.


Obediently, she assumed the position. Her back arched
into a sexy, slutty pose with her miniskirt bunched around
her waist. Her slit was glistening with arousal as I removed
the rest of my clothes, tossing them with undo care onto
the bedroom floor. I then grabbed a condom from the bedside
table.


As I moved closer I couldn't help but lean down and running
my tongue up her wet pussy before stabbing back into her
asshole.


"Sorry, " I apologized, rising to my knees
behind her. "I just couldn't resist. I fucking
love licking your pussy."


"Oh that's okay, " she said with a giggle,
as I rolled the condom onto my cock. "It seems like
you like my ass as well."


"Yep, " I agreed emphatically before spitting
into my hand and rubbing over the shaft of my dick.


I moved into position and used one hand to spread Michelle's
engorged pussy lips as I placed my tip at the entrance, pushing
slowly. Easily, it slid in, her pussy walls slick with fluids.
I gave a few short, gentle thrusts before forcing it in all
the way, my hips pressing firmly against her ass as I buried
my length inside her.


"Ooooh yeah, " she cooed. "That's
what I've been waiting for."


"Oh yeah, " I retorted. "Is this all you've
been waiting for?"


"Hehe....Noooo."


I began fucking Michelle, holding her hips firmly in my
hands as I moved in and out with slow, steady strokes.


"What else are you looking forward to, " I pressed,
splaying her ass cheeks apart to get a view of her enticing
little rosebud.


Again she giggled.


"You know...."


"Say it. I want to hear you say it."


"I..." she began, her voice interrupted by
subtle gasps of pleasure. "I want...you...to...fuck...my...ass."



I smiled.


Maintaining a steady rhythm, I licked my thumb and placed
it against her tiny little dark hole.


"Yeah?" I continued. "You want my dick
in here?"


As I spoke I press my thumb into her ass, wiggling it past
her constricting ring of muscle.


"Yes!" she gasped. "It's all I've
been thinking about."


"Okay...., " I said, sliding my thumb deeper
inside. "Maybe if you're good."


Michelle groaned with exaggerated disappointment as
I gave her a playful slap on the ass.


"Okay, " she conceded, perked up suddenly
by the feeling of my bare hand striking her naked skin. "I'll
do anything you want."


Again I smiled. It was going to be a good night after all.



I continued to increase the pace as Michelle urged me on.



"Harder!" she moaned after about 10 minutes
of solid fucking. "I like feeling your balls slapping
against me."


I complied without a word, driving into her pussy with increasing
force as she continued moaning with approval. As a bead
of sweat began to form on my forehead, I knew I couldn't
last much longer.


"I want to cum in your mouth!" I blurted out,
overcome with sexual energy.


"Okay, " she said, glancing back over her shoulder.
"I want you to come in my mouth!"


A few more thrusts and the time had come. Frantically, I
pulled my dick from her lusciously wet pussy and scrambled
to roll the tight fitting condom off my dick. Struggling
to prevent my cum from blasting forth prematurely, I tightened
my fingers around the base of my dick as I tore the condom
away. Michelle spun around immediately, opening her mouth
as she gazed lustfully into my eyes. Just as the first drop
of cum began to ooze out, I pushed my hips forward and contracted
my pelvic muscles, sending a hard shot of creamy white fluid
directly into her mouth. Before I could do anything else,
she wrapped her lips around my cock as I continued stroking,
sending wave after wave of cum past her sucking lips. Overcome
by the climax I grabbed the back of her head, holding her
in place as my fist pumped with fury, even smacking against
her mouth occasionally as she struggled to take in the entirety
of my constant, streaming load.


As my orgasm subsided, the increased sensitivity in my
dick caused me to pull away abruptly as Michelle looked
up, letting some of the cum run down her chin and down onto
the bed. She continued holding eye contact as she held her
mouth open, forcing me to see my juices collected on her
tongue before locking her lips and swallowing down the
entire load.


I collapsed back onto the bed, a sweaty, tired mess, as Michelle
curled up beside me. As the room became filled with only
the sounds of our breathing and the faint sounds of fucking
emanation from the TV, I realize just how loud the porn was.



"I think I better turn that down, " I said, reaching
for the remote


control. "The neighbours are going to think we're
having an orgy in here or something."


Michelle laughed as she began to remove the rest of her clothing.



"Whoa, " I said, turning to acknowledge her
actions. "Just what do you think you're doing?"



She cast me a perturbed look, as she tossed her shirt into
my face.


"Oh we're not done yet, " she stated adamantly.
"I think there's something else you promised
me tonight?"


"I don't know..." I droned comically.
"It's already past my bedtime..."


Michelle smiled and punched me playfully in the arm.


"Well, " she began. "I guess if you really
need to get some sleep I can let you. I guess you are a lot older
than me, and old men need their rest."


I laughed back at her teasing comments. In a sense it was
somewhat true. With Michelle being 21, I was almost 9 years
older than her. I decided to play along.


"Yeah, " I said, faking a yawn. "I think
I do need to get some sleep. Maybe you can call another one
of your 'internet friends' to pick you up."



"Oh yeah?" she said, moving a little closer.
"And then maybe I'll let one of my other 'internet
friends' be the first one to fuck my tight little virgin
ass?"


I stared at the ceiling for a brief moment before turning
my head to face her.


"Well, okay..." I began. "If you really
want me to.... then I guess....we can do it."


Michelle could sense the playfulness in my voice and she
smiled in response.


"Really?" she asked hopefully.


"Yes. However, I will need a little bit of time to...recover."



"Oh, that's okay, " she countered back
with a smile. "I'm actually keeping myself pretty
entertained at the moment anyways."


After she glanced downward, I followed her line of vision
to see her fingers busy at work between her legs. I let out
a short laugh before speaking again.


"Wow, " I exclaimed. "You are...one...horny...girl."



Michelle just shrugged and cast me a bashful smile. That's
when I noticed her other arm behind her body.


"Hey, " I said, narrowing my eyes suspiciously.
"What are you doing back there?"


"Nothing, " she answered with a giggle, unable
to maintain a straight face. I sat up and peered down at her
body to see the fingers of her right hand tucked in between
her ass cheeks. I moved down the bed to get a better look as
she continued shamelessly fingering her own ass and pussy
in unison.


"You...dirty...little...girl, " I said
with amazement as I pulled back one of her fleshy cheeks
to give myself a clear view of her slender finger sliding
in and out of her tight little asshole.


"So, " she said, giggling. "Are you ready
yet?"


"Oh, I'm getting there."


As I continued to take in Michelle's sexy display,
my hand drifted downwards to grasp my growing cock which
was already beginning to stiffen once again. She smiled
back at me before rolling over onto her stomach and then
rising up onto all fours. As I felt my dick grow larger in
my hand, my eyes remained locked on Michelle as her fingers
continued to penetrate her own pussy and ass in tandem.



"Hold that thought, " I said, reaching over
to the night table.


I slid open the drawer and retrieved a bottle of lube that
I had stashed inside. As Michelle caught sight of the bottle
she smiled in response.


"Are you sure you're ready for this?" I
asked, moving back into position behind her.


"Yes!" she answered emphatically, dispelling
any doubt in my mind.


I grinned as I flipped the bottle open. Holding it up, I then
began to drizzle the clear liquid down onto Michelle's
ass at the bottom of her tailbone. She let out a faint giggle
as the lube started a slow trickle down between her cheeks,
making its way to her finger which was still buried knuckle
deep in her own ass. As she began to withdraw her finger,
the fluid collected around the digit, coating it as she
pushed it back inside.


"Oooooohhhh, " she purred, sliding her lube-coated
digit in and out of her virgin asshole.


I watched with fascination as I squirted some of the lubricant
into my hand and began stroking my shaft, covering it with
the slippery substance. I moved closer, my cock now throbbing
in my hand, aching to enter Michelle's irresistible
little orifice. I peered down at her finger, glistening
with lube, sliding in and out, forcing itself deeper with
every thrust.


I reached down and took hold of her hand, gently prompting
her to withdraw. Reluctantly she did so, pulling her finger
free with ease. I could almost sense the anticipation building
in her body as she waiting. After months of dirty emails
and phone sex conversations it was about to happen. I was
going to fuck Michelle's ass.


Gripping my dick firmly, I slid the head up and down her wet
crack before finding her tight little star. Slowly, I began
to push.


"Shit, " I cursed, as my cock slipped down towards
her pussy. "I think I used too much lube."


Again I tried, only to have my dick slide up in between her
ass cheeks eliciting an amused laugh from both of us.


"Okay, " I stated with firm resolution. "Third
time's the charm."


Holding my clenched fist against her asshole, I slowly
pushed forward, butting the head of my cock against her
willing but difficult ass. I bit my lower lip with dedicated
concentration as I felt her tight hole gradually give way
and allow my dick to penetrate her most private of body cavities.



"Uhhhhhhhggggg, " Michelle moaned, as my
head slipped inside her ass. I couldn't tell it the
moan was from pleasure or discomfort.


"Play with you pussy, " I suggested, pausing
only briefly before pushing more of my cock into her asshole.



She took my advice, but I could sense something was wrong.
Her body seemed tense and apprehensive.


"Are you okay?" I asked, briefly halting my
cock's anal invasion.


"Yeah, " she answered back meekly and unconvincingly.
"Keep going."


Again I resumed, using one hand to slowly guide my dick deeper
into Michelle's clenched butthole. Perhaps I was
a bit overzealous, or maybe she just wasn't ready,
but after a few seconds more, she crawled forward off my
cock holding her hand gingerly against her recently reamed
hole.


"Ahhhhgggg, " she cursed in frustration.
"I can't...It's...too painful."



Although I was disappointed, I tried to hide it in my concern
for Michelle's well-being.


"That's okay, " I offered in condolence.
"Girls usually have a hard time when they try it for
the first time."


Michelle let out a bit of an histrionic whine as she glanced
back over her shoulder with a timid, puppy-dog expression.



"But I want to do it sooo bad, " she pleaded,
beating her hand against the mattress in frustration.
"And it...did feel...good. It's just that...."



"I know, " I said, offering comfort. "It's
okay. In fact, let's try something else."


Michelle's interest seemed to be peaked as I once again
returned to the night table beside my bed. This time I rummaged
a little deeper to find what I was looking for. Behind the
condoms, handcuffs, and blindfolds and other paraphernalia,
I found what I was looking for.


"Stay there, " I told Michelle, who was now
in a side-lying position facing away from me.


From the drawer I pulled a 5 inch long, pink butt plug that
I had purchased off the internet some time before. I had
bought it for use with a previous female 'friend'
although it had arrived too late for us to make use of it.
I set it on the bed, as Michelle remained lying on her side,
obviously curious about what I had in mind. I then retrieved
another condom tore open the package. I noticed that it
smelled like oranges. 'It must be from the tropical
variety pack I had bought last month, ' I thought to
myself as I rolled it onto my dick. I applied the lube liberally
to both the plug and to my rubber-covered cock before inching
back to Michelle's waiting body. As my slippery fingers
began to explore her pussy and ass, she sighed contentedly.
I coaxed her to roll over a bit in order to gain access to her
pussy, which I penetrated with my fingers before replacing
them with my dick. Once Michelle's pussy had swallowed
my entire length five of six times with slow methodical
plunging, I picked up the pink, rubber plug and placed the
narrow tip against her noncompliant asshole.


"Oooh, " she blurted out as she felt the tapered
point poke past her wet, muscular rim.


With my cock completely buried inside her, I began rotating
the plug as I slowly pushed it up her ass. As the plastic toy
was much more streamlined and quite a bit smaller than my
dick, it slid it with little effort. Michelle shifted her
body and sighed with pleasure, obviously enjoying the
sensation of having both holes filled.


As my hips began to rock with short, quick thrusts, I forced
the plug deeper causing her asshole to stretch wider and
wider. It was almost completely inside her now as she squealed
in ecstasy. The widest portion of the toy soon passed her
tight, muscular ring allowing it to clamp down around the
much narrower base that then followed. I smiled with satisfaction,
seeing the pink, rubber toy completely embedded in Michelle's
asshole with only the flat base visible.


"How does that feel?" I asked, rotating the
plug around inside her ass. "Mmmmm, " she purred
lustfully. "So fucking good!"


As I tugged on the buttplug, I began fucking her pussy with
increased vitality, pausing every now and then to wiggle
the plastic toy around insider her ass.


"Oh yeah!" she called out. "Fuck me! Fuck
me hard!"


Again I complied, holding the plug firmly buried inside
her as I slammed my hips into her ass.


"Uh! Uh! Uh! Uh! Uh!" she blurted out with each
thrust, until I felt her body tense once again.


And it was then that I felt the strangest sexual sensation
that I had ever felt. Her pussy clamped down around my cock
like a vice. The force was so strong I felt as though she might
actually sever my dick from my body. I tried to pull out,
but the iron grip of her cunt held me in place until her orgasm
subsided. It was only then that I could resume my thrusting,
bringing me closer to my second climax of the night.


A few more forceful thrusts, and I slammed my body into hers,
groaning uncontrollably as I spilled a thick load of cum
into the condom. 'Fuck, I hate condoms, ' I thought
to myself, as I caught my breath, my dick still buried inside
Michelle's ravaged pussy.


Slowly, I extracted the plug from her ass, followed by my
dick from her pussy. Michelle rolled over smiling, eyes
closed in contentment. I laid back on the bed, leaving the
condom on my dick, but setting the buttplug on the night
table beside me.


I was now officially tired.


I hoped Michelle, felt the same way, because there was no
way I was going to go another round, and I definitely was
in no mood to drive her half way across the city to take her
home. Luckily, she curled up beside me and closed her eyes.



Soon we were both asleep.


* * * * * * * * * * * * * * When I awoke it was still dark outside.
I rubbed my eyes drearily as I glanced over at the clock.



"5:38, " I groaned, rolling back over only
to find myself blocked by Michelle's sleeping body.



I cursed silently to myself as I struggled to find a comfortable
position. As much as I loved "sleeping" with
girls, I hated actually sleeping with them. I rolled over
and closed my eyes again, vowing to buy a bigger bed.


* * * * * * * * * * * * *


When I awoke next, it was light outside. I could hear the
birds chirping. Beams of light were shining through the
open spaces in my blinds as I buried my head under the covers
to escape back to my isolated world of comforting darkness.



Then I felt a body shift next to me and I remembered that there
was someone else in bed with me. I groaned silently to myself,
not wanting to engage in the menial small talk that often
follows nights of sensuality. For a moment I thought that
if I just pretended I was sleeping then she would call a cab
and go home.


Ten minutes passed.


Then twenty minutes passed.


Then thirty.


Then an hour. I was growing restless.


I rolled over and looked at Michelle. She seemed restless
but sill sleeping. Drearily, I hauled myself out of bed
and went to the bathroom, hoping that after a long shower
I could return to find her gone with a nice succinct note
in her place.


No such luck.


As I came out of the bathroom, a towel around my waist, I was
caught by a sudden rush of cold air that reminded me to close
the windows before going to sleep. As I made my way down the
hall back to the main room, I saw Michelle curled up in the
blankets with her head poking out from above the covers,
smiling with a sleepy expression.


"Good morning, " I said, climbing back into
the bed, still a bit damp from the shower.


"Mmmm, Morning, " she replied, stretching
her arms out in a prolonged yawn.


About 30 minutes of casual conversation then ensued, with
neither of us mentioning the events of the previous evening.



"So...." I began, sitting up in bed. "Do
you want a ride home?"


Michelle groaned and cast me a pouty expression.


"What?" I asked, furrowing my brow with fake
concern.


I knew what she wanted. For some reason girls seem to love
morning sex, and I knew right then that I was going to have
to give her at least one more orgasm before I could take her
home.


"Oh?" I continued playfully. "Is there
something else you would like before you go?"


"Maybeeeee...., " she replied sheepishly,
pulling the covers up to half cover her blushing face.


"And just what would that be?" I asked, crossing
my arms over my chest. "I...want to...try it again."



"Huh?" I stammered, completely caught off
guard by her response.


"I want to try it again, " she reiterated, this
time answering with more conviction.


"You mean...?"


"Yes."


"In your...?"


"Yes!"


"Wow, " I exclaimed, shaking my head in disbelief.
"Umm, okay. Yeah, I guess we can try it again..."



"Oh? So what? Now you don't want to fuck my ass?"



I laughed as I waved off her insinuating comment.


"No, no, no. Of course I want to. It's just that...If
you couldn't handle it last night then..."


"Well I want to try, " she stated firmly, cutting
me off.


I could tell Michelle was used to getting her own way. I tossed
my hands up in resignation.


"Okay, then. Let's do it. But first....."



"What?" she asked, her eyes widening with curiosity.



"I think..., " I continued, smiling. "I
really want you to put my dick in your mouth."


Michelle smiled back. I knew she liked my idea.


Without a word, she moved down the bed, pushing the covers
off my naked body. Just the thought of having Michelle's
pouty lips wrapped around me once again had already started
the familiar rush of blood into my dick. As I settled back
into a comfortable position, she placed herself between
my legs, lying on her stomach and taking my growing cock
in her hand. She gave it a few slow strokes as she glanced
up at my expecting face. I placed my hands behind my head,
settling back with a contented smile as I watched her plant
a soft kiss right on the end of my dick. Michelle let her lips
linger there for a moment before slowly allowing them to
spread, taking my head into her warm, wet mouth. She finally
broke eye contact as her lips descended down my shaft, her
tongue sliding down the underside. As she reached the base,
where her fingers were wrapped around my cock I could feel
her tongue-ring flicking around inside her mouth.


"Play with my balls, " I suggested as I watched
her pouty, pink lips gliding up and down my wet shaft.


With her other hand, she reached down and cupped my sensitive
balls, stroking her fingers along the underside before
giving them a gentle squeeze. I winced as she kept squeezing,
perhaps a little bit too hard. I was about to ask her to stop
when she lowered her head and ran her tongue over my balls,
sending a pleasurable shiver throughout my body. I moaned
in approval as lips and tongue covered them with soft licks
and kisses before returning her attention to my dick.


"Mmmm, you're pretty good at this, " I
said softly as her lips once again wrapped around my cock.



"Hehe, " she giggled, her cute voice muffled
by my dick in her mouth. "Thank you."


As she started to compliment her sucking lips with slow,
long strokes of her hand I could feel myself swelling in
her mouth. I reached down to move a few strands of hair out
of her face, giving me a better view.


"I like to see, " I explained when she cast her
eyes up at me with curiosity.


After about ten straight minutes of Michelle's oral
handiwork, I was sufficiently worked up to escalate the
situation.


"Okay, " said, grabbing a condom from the night
table. "I want you to get on top."


Compliantly, Michelle gave my dick a few more strokes before
rising up to her knees.


"Which way do you want me to face?" she asked
as I rolled the condom onto my throbbing, wet cock.


"That way." I ordered, referring to the end
of the bed.


She gave me one more amorous smile before throwing a leg
over my body, holding herself in a squatting position directly
above my waiting dick. As I held it pointing upwards, Michelle
reached down to guide the head into her moist, little hole,
slowly lowering her body downwards. Her pussy gripped
my cock as I watched her lips sliding down my length. Once
she had fully descended and my cock was firmly embedded
inside her, I tentatively released my hold on my shaft.



Placing her hands on my thighs for balance, Michelle started
moving herself up and down on my dick, showing a remarkable
display of leg muscle endurance. The feeling was amazing,
as I watched her little round ass repeatedly ascend and
descend, her pussy gliding up and down with ease. I noticed
her breathing getting quicker as she increased the pace.



"Will you play with my ass?" she gasped, looking
back half-way over her shoulder.


"Maybe..." I answered, although I was already
licking my fingers in preparation. "...if you say
please."


"Please, " she shot back with hesitation.
"Please play with my asshole."


Those few words turned me on even more and I quickly removed
my wet fingers from my mouth and placed them over her tight,
anal opening. Michelle purred with gratitude as massaged
her tiny little butthole with slow, circular motions of
my thumb.


"Inside, " she gasped again. "Put it
inside."


Again I complied, replacing my thumb with my middle finger,
wriggling it past Michelle's tight muscular ring.
She tossed her head back in lustful bliss as she felt my finger
sliding smoothly into her asshole.


"Oh yeah, " she moaned, leaning forward to
allow me to go deeper. "That's what I like!"



As Michelle continued bouncing up and down my cock, I held
my hand stationary allowing her asshole to slide and down
my finger as well.


"Mmmmm, " she purred, growing more aroused
by the second. "I can't wait to have your dick
in my ass."


I felt myself getting close to orgasm.


I'm going to cum soon, " I warned, nearing climaxing
due to Michelle's twitching butthole tensing around
my finger.


"Noooooo, " she cried out, stopping all movement.
"Not yet."


I was on the brink. I felt as if anymore movement at all would
send me over the edge.


"Okay, " I gasped, trying with all my willpower
not to cum. "Get off. Slowly."


I took a deep breath as Michelle cautiously lifted herself
off my cock. As I slipped free, my dick fell to my stomach
with a wet "slap". She sat kneeling in front
of me impatiently as I waited for my impending climax to
subside.


"Okay, " I said with relief. "I think
we're good."


"Yeah, " Michelle said, laughing. "That
was a close one."


"Yeah, sorry about that. Now...where were we?"



"I think..." Michelle began, as a mischievous
smile appeared on her face. "You were about to bend
me over."


"Oh was I?" I retorted in a teasing manor.


"Yep!" she piped out cheerfully before a shy
expression once again her. "And..."


"What?" I prompted.


"Could you use the buttplug on me again?"


"Of course! So I take it you enjoyed that last night?"



"I loved it! Although...I still want to try your dick
in my ass again."


"No problem, " I stated, reaching over to grab
the pink, rubber plug and the bottle of lube. "I'll
use the plug first though. It should help you relax and get
used to the feeling. It'll make it easier when I actually
fuck you in the ass."


Michelle could not hide her enthusiasm.


"How do you want me?" she asked, her face beaming
with excitement.


"On your hands and knees, " I replied simply,
flipping open the cap on the lubricant.


As Michelle assumed my favourite position, I covered toy
with lube in preparation. A few seconds later we were engaged
in a replay of the previous night with my dick in her pussy
and the pink, rubber plug buried snugly in her tight little
ass.


"Mmmmm, " she moaned, as my cock plunged in
and out. "I love this!"


"Oh yeah? You like having both your holes filled?"



"Mmmm, I love it."


I gave her a firm slap on the ass, eliciting a surprised squeal
from Michelle's mouth.


"I bet you wish this was a cock in your ass don't
you?"


Again, I brought my hand down on her ass.


"Yes!" she blurted out as I smiled to myself.



I continued fucking her holes as she fingered herself through
two successive orgasms. It was then time to try again.


"Are you ready?" I asked, rotating the plug
around in her asshole.


"Yes, " she answered firmly. "Let's
do it."


Slowly, I withdrew the rubber toy, watching her pink butthole
close back up into a tight little knot. As I pulled my dick
out of her soaking wet pussy, I peeled the condom off and
tossed it aside. After applying a generous amount of lube
to my bare cock, I rose back up to my knees behind her.


Clutching my shaft firmly in my hand, I guided the head to
Michelle's tightly closed opening. Pushing slowly
but forcefully, her asshole gradually began to give way,
accepting my pulsing cock into her tight depths.


"Uhhhhhhhhhh, " she moaned as my dick slowly
disappeared into her hungry butt.


"Are you okay, " I asked, stopping my anal penetration
to check on her status.


"Yes, " she replied confidently. "Keep
going."


I smiled with relief and resumed stretching her asshole
with my invading cock. After a few minutes of cautious thrusting
I was able to fill her ass completely as she continued moaning
with increasing enjoyment. Slowly and methodically,
I began fucking Michelle's virgin ass.


"How does my ass feel?" she asked, her voice
slightly muffled by the blankets her face was buried in.



"So fucking good!" I exclaimed, building up
increasing speed. My arousal was beginning to peak. I slapped
Michelle's ass a couple more times as she purred in
approval.


"How does my cock feel in your ass?" I then asked,
craving to hear her voice some dirty words of her own.


"So good!" she gasped, her breath growing shallow
and laboured. "I love having my ass fucked!"



"Yeah? Does it make you feel dirty?"


"Yes!"


"Does it make you feel like a slut?"


"Yes!" she cried out again as I plunged repeatedly
into her tiny opening. "I feel so slutty when you fuck
my ass!"


"Are you going to let me fuck it whenever I want?"



"Yes! My ass is yours! I want to be your dirty little
ass-whore!"


That was exactly the type of talk I was hoping to hear.


"Good, " I hissed, reaching down to grab a handful
of her hair. "Keep talking like that until I cum in
your ass."


"Fuck yes!" she cried out, her voice growing
ragged and unstable. "I want you to fuck me like a dirty
little slut and cum in my asshole!"


I slapped her ass again and pulled her hair, encouraging
her to continue.


"Oh yes!" she exclaimed, obviously enjoying
the rough treatment. "Fuck like a whore! Use me! Use
my tight little asshole and then fill me full of cum!"



That was it. I could no longer hold back the tide.


With one final groan, my dick slipped deep into Michelle's
ass, spraying her insides with cum. I just held it there,
completely buried, as my cock continued to pulse, spilling
an unending flood of creamy fluid into her well-fucked
hole. Michelle moaned pleasurably as my body twitched
one last time and my slippery pole slid back out of her ass.



As we both collapsed into the bed, I felt a wave of fatigue
sweep over my body. My arousal soon dissipated, only to
be replaced with the post-coital disinterest that men
generally feel following sex.


"Well, " I said, finally rising from my drowsy
state. "I guess I should take you home now before I
fall asleep again."


"Ok, " she replied timidly.


She seemed disappointed.


After a lengthy search, we were able to locate all of our
scattered clothing and seen headed out on our way. The drive
was long, but since it was early Sunday morning there was
very little traffic to contend with. As I dropped her off
at her house, we said a couple awkward goodbyes and she closed
the door.


I shook my head with amazement as I drove away. I had just
met Michelle. Since last night I had licked her pussy, licked
her ass, fucked her pussy, fucked her ass and came in her
mouth.


We hadn't even kissed once.


"Wow, " I said to myself, as I reached for my
sunglasses. "This internet dating thing might be
useful after all.

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Member Responses Post Your Comment

Members can vote on this response!

mmmmmmmmmmmmmmmm, absolutely great story, I love asian
women, they are so sexy to play with. Love to hear more, cheers.

7/17/2010

Members can vote on this response!

That was awesome and erotic as hell

8/1/2017