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
"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.
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
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
"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.
"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
"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
"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
"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.
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
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
"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
"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
"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
"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
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
"Get on your hands and knees," I stated simply, more as an order than a
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?"
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.
"Say it. I want to hear you say it."
"I..." she began, her voice interrupted by subtle gasps of pleasure. "I
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
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
"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
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
"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
"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
"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
"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
"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
"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
"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
"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
"I know," I said, offering comfort. "It's okay. In fact, let's try
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,
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
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
"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 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
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
"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.
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
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
"Will you play with my ass?" she gasped, looking back half-way over her
"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.
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.
"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
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
"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
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
"Uhhhhhhhhhh," she moaned as my dick slowly disappeared into her hungry
"Are you okay," I asked, stopping my anal penetration to check on her
"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?"
"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
"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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