Andrew to Ashleigh Part 1 The Change
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Andrew To Ashleigh - Part 5: One Hell Of A First Date free porn video
The rest of the weekend was pretty quiet - but then it would have been
hard to top Friday night. I woke up early Saturday afternoon, splayed out
on my bed, still wearing my dress and heels from the night before. I had
a hell of a hangover, but I didn't care - Alex's beautiful face
immediately filled my mind and I found I didn't really care about
anything else. As I lay there, I mentally played back the events of the
previous night and found myself feeling warm again. I got up from bed and
stripped off my outfit from the prior evening, then stumbled into the
bathroom and cleaned off all of my makeup (I had to stop falling asleep
with it on!). I put on a bathrobe and went out into the kitchen to get a
glass of water (fortunately Brendan and Tay were either still passed out,
or had gone somewhere), then retreated back into my bedroom. I drank
several glasses of water, along with a couple of Advil, then took a long
hot shower. As the water caressed me, I imagined being back in Alex's
strong arms. My hand slid between my legs, and I fingered myself, cumming
quickly (too quickly!). After I finished my shower, I spent the rest of
the afternoon on Saturday recovering, and I stayed in Saturday night
scrolling through Pinterest and Instagram and watching tons of makeup
videos on YouTube.
I found I couldn't stop thinking about Alex - I was totally smitten. As I
thought ahead to our date the following weekend, I knew that I wanted to
keep up my all-out assault to win him over. Since he was so tall, I knew
I wanted to take advantage and wear super tall, "fuck-me" heels, and I
knew that I didn't have any, or any idea how to walk in them. That meant
I had to figure out my whole outfit quickly to give me enough time to buy
the shoes and practice not falling on my face! On Sunday I enlisted
Taylor to come around to the boutiques to see what we could find. After
some searching, I found a sexy black dress with a low-V neckline and a
lacy skirt that flared out just below mid-thigh, before ending at the
knee. Taylor found the perfect shoes to go with - black patent peep toe
pumps with a five-inch stiletto heel and a thin ankle strap. They were
super intimidating and super erotic at the same time.
I spent the rest of the day learning to walk in my new heels (thanks
again, YouTube!). I was slowly getting the hang of it, and I was
pleasantly surprised to find they weren't much harder than the three-inch
heels I'd be wearing (though definitely more tiring!). I'm sure our
neighbors downstairs loved hearing me click back and forth around the
apartment as I did laundry and straightened up! I was lucky that I didn't
fall at all, but I had pretty good balance, I guess. The biggest thing I
noticed was that I had to be slow and deliberate with my movement, and to
take small steps. So long as I paid attention to that, walking was
actually pretty easy.
Monday was a pretty normal day at work, and on Tuesday, I woke up to a
text from Alex: "Can't get you out of my head. Saturday night, Otheroom
in the Village for drinks at 9:30?"
Of course, I immediately wrote back yes! I couldn't stop thinking about
Alex either, and it got even harder after that text. I couldn't wait to
make him hard too. It was difficult to stop thinking about seeing him
naked and taking his big cock inside me. It was going to be a long week!
Wednesday, I noticed my nails had grown out enough to have a noticeable
gap below the gel polish, so I asked Taylor if she wanted to go get manis
on Saturday (which of course she did, it's Taylor!). I wanted to get
longer nails this time, so I spent a few hours on Thursday down the
Pinterest rabbit hole searching for just the right look. I decided on
half-inch long gel ballerina nails in a French ombre - sexy and super-
feminine; I think Taylor literally squealed when I told her.
On Saturday morning, I drove Taylor and me to the salon. Taylor told me
on the way that she'd decided to go for the same look - we'd be mani-
twins!
In the salon, I told the nail tech the look I wanted, and I showed her a
picture of the look that was my inspiration, and pointed to Taylor's
tips. "I'd love for my nails to be the same length as hers."
The tech laid everything out and got to work. My mani was much more
elaborate this time around (Taylor had it easy since she was just getting
a fill and recolor).
First, she wrapped my fingertips in foil and soaked off my current gel
polish with acetone. Bye burgundy nails! Then she cleaned up my cuticles,
then filed, buffed, and prepped my nails with the gel base coat. After
that, she sized the tips and glued on each nail. Before she cut them
down, they extended nearly an inch and a half past my fingertips! That
would be interesting to try some time, I thought. She then cut and filed
the tips to the right length and shape, then proceeded with the layers of
pink and white gel interspersed with UV curing.
When she was done, I looked at my hands and wanted to cry. They were so
beautiful! Never in my wildest dreams had I imagined having this
experience. My long, slender fingers were each tipped with a pale pink
nail that faded to white at the tip, in a shape that mimicked a ballet
slipper. The tips extended a little bit further than half an inch past my
fingertips; I had never before felt so delicate and feminine than in that
moment. As I admired them, wiggling them in the air, I was in love. I
knew that I'd never want to wear anything shorter than this again.
As I reached in my Coach tote for my phone and my wristlet to tip the
tech, I quickly discovered that I needed to recalibrate how I used my
hands! The nails were hot, but they made my fingers just that much longer
than I was familiar with. Just like with the stilettos, the trick seemed
to be slow, deliberate movements. As I opened my wristlet, shifting the
contents around with my nails, I realized that I'd never get tired of
that view. I loved seeing my ultra-girly hands doing even simple things,
like handing a $20 to the tech, or paying with my Amex gold card up
front. Even hearing the click when the nails met a hard surface turned me
on. I was smitten!
Taylor and I left and decided to stop for lunch at a new Cuban restaurant
uptown on the way home. I think the waiter was checking out my nails, so
I made sure to flaunt them the entire meal. It was super fun. I had a
delish arugula salad with shrimp and jicama. I made extra sure no garlic
- that would be a disaster for later! After we paid, we went home.
As we were dropping our stuff, I said to Taylor, "Girl, as hot as our
nails are, we have to Insta that shit."
"Um, fuck yes. I am totally in love with the new you, Ash. Like I would
seriously go fuck you now, you've got me so hot with your new attitude."
I was intrigued at the thought, but only said "You slut, I'd show you
such a good time too. Bring your hand over here!"
She came over to where I was standing and we both held out hands out over
the marble countertop. I snapped a few pictures of our matching manis
with my iPhone and posted on Instagram: "#Datenight means #superfemme,
#fresh #gelnails. Loving the #frenchombre with my mani-twin, @TayTay1996.
Love you girl! #nailgoals #nailsofinstagram", again bookended by fire
emoji and nail emoji.
I figured if the night went well I'd want plenty of energy later, so I
took a long nap. Around 6, I had a light dinner and a glass of sauvignon
blanc to calm my nerves. At 7, I started getting ready; I laid out my
dress, my shoes, a black clutch from my closet, and I picked several
silver rings and a small silver pendant. I also added a cute silver cuff
bracelet for good measure. My nerves were going crazy, and at the same
time, I couldn't wait to see Alex.
At 8, I began my makeup, starting with my foundation. From there, I did
my eyes in a blend of brown and gold shadow, with a dramatic slash of
black eyeliner on each lid, followed by a light shimmery layer on top. I
added a healthy dose of mascara to each eye. Next was a subtle rose blush
under my cheekbones. Last was a dramatic glossy red lip. I wanted Alex
thinking about kissing those lips all night long. I also wanted him
thinking about having them wrapped around his cock. What better way to do
that than with classic fuck-me red? I wanted the rest of my makeup to be
subtle enough to not steal any attention.
By now, it was time to get dressed. I put on a tiny black silk thong and
a lacy black push-up bra, then stepped into my dress, pulling it up and
slipping the thin straps over my shoulders before zipping it up. It felt
amazing to be wearing such a beautiful, feminine dress; I wanted to twirl
in joy. Since it was late September, I figured it shouldn't be too cold,
so I grabbed a filmy linen scarf, that I draped around my shoulders as a
shawl (while it seemed a shame to cover my breasts, I had to admit it was
a cute look). Lastly, I buckled into my new heels. My nails made it a
little slow to do the tiny buckles on the ankle straps, but I got there
(and seeing my long nails right next to my new stilettos was so hot!).
When I finished, it was 9 pm, so I headed out. Taylor was getting ready
to go over to Brendan's, and she blew me a kiss.
"Good luck, baby! Go wrap that man around your little finger."
"I plan to do just that, Tay. Hope Brendan shows you a good time too!" I
winked and blew a kiss as I walked out the door. Walking anywhere in
these heels was out, so I took an Uber to the PATH station, then a train
to Christopher Street. As I rode the PATH, I caught a guy checking me
out, which really turned me on. I deliberately shifted my shawl so that
my cleavage was exposed, and held my phone so that my nails were
impossible to miss. The ride was short though, and I got off at the first
stop. I forgot how much I hated the Christopher Street stairs, but it
wasn't noticeably worse in my heels. Otheroom was only a couple of blocks
from the PATH station, so I decided to just walk; I got to the bar just
after 9:30. I saw Alex sitting at the corner of the bar with an empty
high-backed bar stool catty corner to him. It took most of my willpower
not to go jump on him, because he looked super yummy in his adorable
preppy way. He was wearing jeans and a blazer again, this time with a
light blue and pink tattersall shirt and a pink and baby blue polka-
dotted handkerchief in his jacket pocket. He was wearing a cool pair of
Chelsea boots this time, I noticed. God, he was so handsome.
He looked up and noticed me as I walked across from the door, and his
eyes lit up as he smiled. He stood up and said, "Hey Ash - great to see
you! I'm so glad you could come."
I put my hand on his chest and leaned up to give him a quick kiss on the
lips. My goal for drinks was to leave him wanting more the entire time,
so that by the time we got back to his apartment (hopefully, anyway!),
he'd be wild with lust. It seemed to be working, as he looked like he was
hoping for more when I broke off the kiss. I didn't want to deflate him,
so I said, "Me too, Alex. I've been thinking about you all week - I
enjoyed last Friday night a lot! I'm hoping we can have even more fun
tonight." I gave a sultry smile at that.
His eyes brightened and we sat down. Just like the prior week,
conversation came easily, and flowed naturally back and forth between us.
His trip had gone well, and they had a number of encouraging meetings
with potential clients. I suggested we get some Taittinger to celebrate,
which we did. After toasting his success, we switched over to wine; I had
a delicious Cotes du Rhone, and he opted for a Sangiovese, and we talked
about wine for a while.
Based on the way we were seated, I had optimal position for some serious
flirty touching. As the night went on, I made sure to take every possible
opportunity to touch his leg or hand for emphasis, and I made sure to let
my hand linger longer than strictly necessary. I also used my new nails
to great effect, softly raking the skin on the back of his hand several
times as I drew my hand away. These always seemed to elicit a shiver from
him, which was a great sign.
On one of the times I had rested my hand on his, and was surreptitiously
tilting my hand so the nails were against his skin, he said, "I love your
new manicure!"
I replied, "I'm surprised you noticed! Guys don't usually pick up on that
sort of thing."
"Nah, they're really sexy. I like 'em a lot!"
"I'm glad to hear that - I'm a big fan too. They're super girly, which I
like, obvi - um, have you met me? - and so flirty. I've heard they're
good at other things too." At that, I pulled my hand away, drawing the
nails a bit more forcefully across his hand. I saw him smile and shudder
at that. Bingo.
From here, the flirtation took a more overt turn, as I said, "Maybe you
can help me figure out what sorts of things those are?"
He replied, "I'd love to. I bet you'd love that too."
"I bet you'd make sure I loved it, wouldn't you? I know you'd love it"
"You have no idea."
I uncrossed my legs and re-crossed them at that point, drawing one of my
feet slowly up the side of his leg as I did so. "What sort of things did
you have in mind?"
He leaned in toward me, and I mirrored him. He rested his hand on my
thigh, and slid it ever so slightly up my leg, which sent a shiver of
delight through my body. "Do you want to get out of here? I'd love to
show you."
"I thought you'd never ask."
"My place? We can catch an Uber and be there in less than 10."
"Mmm, yes please."
Alex settled up, and the Uber came just as we were leaving the bar. The
whole ride to his place, he had his hand on my inner thigh and was softly
rubbing while we talked, like it was the most natural thing in the world.
I took revenge by tracing one of my nails up and down the inside of his
forearm at the same time. I'd like to think the driver didn't notice, but
I'm sure he did. I figured, hey, at least we weren't drunks throwing up
in the back!
When we got to Alex's building, he offered me his arm when I got out.
"Careful in those shoes, the street's cobblestone. Don't want you to
break an ankle."
I gladly slipped my hand inside his arm, and stepped carefully on my tip-
toes to avoid tripping on the cobblestones. His building was an old
converted warehouse. We went into the elevator from the lobby, and he
swiped a key fob over a sensor before pressing the button for the 5th
floor - the top floor. As soon as the doors closed, we attacked each
other, kissing deeply and forcefully. Alex bent down slightly and picked
me up, pressing me into the side of the elevator; I wrapped my legs
tightly around his ass, and draped my hands around his neck. I ran one
hand through his hair, raking my nails across his scalp, and with the
other, I drew my nails across his shoulder and the side of his neck. That
made him kiss me even more deeply, which (of course!) was exactly what I
was hoping for.
When the doors opened, he didn't put me down, as I expected; he carried
me out of the elevator, which exited directly into his loft. He had the
entire top floor of the building. We were in a wide-open
living/dining/kitchen area (at least I think - it was tough to pay
attention to anything other than Alex at that point). He set me down on
the kitchen counter and drew back from our kiss. We both paused to catch
our breath.
Alex spoke first. "You are one hell of a kisser."
"You're pretty good yourself."
"I think we found one of those things your nails are good for. What you
were doing to my head and neck while we kissed was incredible."
"I thought you'd like that." I put my hand on his cheek and drew the
backs of my nails seductively down his cheek, and then the side of his
neck to his chest, eliciting a moan of pleasure from Alex. At the same
time, I drew my other hand upward, where they met at the top button of
his shirt, which I quickly undid, followed by the second and third
buttons.
As I leaned in to kiss him, I slid my hands inside his shirt and onto his
chest, which was rock hard. I paused with my lips an inch from his,
gently drawing my nails up and down his chest inside his shirt. I
playfully said, "Would you like to play some more?" His only response was
to grab the back of my head with his hand and to pull my lips to his,
where he greedily sucked on my lower lip, then practically attacked my
mouth with his tongue. All the while, I was gently scratching at his
chest and shoulders with my nails; it was clearly driving him mad with
lust as he kissed me with an almost animal ferocity. It turned me on so
much to see him so turned on.
He shifted and began kissing and nibbling at my neck. I left one hand
inside his shirt, toying with his muscular shoulder, and drew the other
one up to scratch his scalp. At the same time, he began to lick and suck
at the nape of my neck and collarbone, freeing me to whisper in his ear,
"Mmm, baby, you're making me so wet."
He drew away from licking at my neck and with a look of primal passion,
again picked me up, carrying me to the bedroom. He had a king bed with
soft dark sheets; in the moment, I only noticed when he gently lowered me
onto it. He kissed me fiercely. At the same time, I slid my hands inside
his jacket and shoved it off his shoulders. I then undid the rest of the
buttons on his shirt, exposing his tight, sexy six-pack. He slid his
shirt off and picked up my hips, then shifted the skirt of my dress up
above my pussy. He pulled my thong down, past my shoes and tossed it on
the floor, then pulled his jeans off and knelt on the floor at the foot
of the bed. He again slid his hands under my legs and, grabbing my hips,
pulled my pussy into his waiting face. It was so fucking hot, it took all
of my focus to slide one hand down, and with my long-nailed fingers right
in front of his eyes, spread apart my lips to better expose my clitty to
his tongue. My other hand gripped the back of his head, my long nails
digging into his scalp, and held it tight to my wet slot. His tongue was
amazing, and he was so delicious that (despite my efforts to ride the
growing wave of pleasure) I quickly came, moaning in ecstasy.
I reluctantly pushed him away from my pussy and stood up to unzip my
dress. I let it fall off my shoulders, then undid my bra. I was naked
except for my stilettos, which I found super-hot. I pulled his face down
into a kiss and could feel and taste my wetness on his cheeks and mouth.
From inside his boxers, I could feel his cock pressing insistently
against my leg. I drew one hand down from his face, dragging my nails
down his chest and over his yummy abs. I sensuously slid one nail under
the band of his boxers, and drew it across his body, eliciting a moan of
pleasure from Alex.
I slipped my hand down and grabbed his massive cock. I pretended a gasp,
and put my other hand in front of my mouth, saying, "What do you have
down there? I'd better take a closer look." I licked his lips and began
kissing my way down his amazing body. When I got to his abs, I raked the
nails of my left hand down to the waistband of his boxers, and with both
hands slid them off. In that moment, I had my first up close view of
another man's cock. It was like a dam burst in my brain, and I was
completely overcome with a powerful desire for his cock. The sight was
magnificent and I wanted nothing more than to worship it, to ravish it
with my mouth, to take it deep in my throat and devour it whole. I forced
myself to move more slowly, to draw out the pleasure for both of us.
I sank to my knees, murmuring sexily, "You've had this delicious present
for me in your pants the whole night and didn't say anything? Tsk - what
a naughty boy!" To punctuate, in one motion I grasped his dick gently at
the head, slid my hand down to rest where his penis rose out of his pubic
hair, fingers splayed, nails gently digging into the skin of his crotch,
and seductively licked the tip. I tasted a drop of salty precum, which
was an interesting sensation for the first time (but one with which I'd
become intimately familiar in very short order).
I swirled my tongue around the tip of his cock, then licked it from base
to tip with my tongue, like a lollipop. It was about 8" long, and very
thick. I licked the tip several more times, looking up at Alex through my
eyelashes, saying between licks, "Do you like seeing my cherry red lips
on your cock? Does it make you as hot as it's making me?" Then I moaned
and brought my hand around it again, so he would see my nails on it. "Do
you like seeing my sexy nails around your cock?" Lick, lick, lick.
"Oh Ash, oh god yes, oh fuck yes. Please don't stop."
"Well. Since you asked nicely..." I closed my mouth tightly around the
tip of his cock for the first time, licking and sucking in equal measure.
I gently raked my nails up and down his cock, first the smooth fronts,
then the tips. I bobbed my head as I sucked, each bob pushing him further
into my hungry mouth. The whole time, I swirled my tongue forcefully
against his skin as I sucked on him. A little less than halfway down, I
felt his cock hit the back of my mouth. Feeling no gag reflex, I pressed
on, slowly taking him into my throat, bobbing gently up and down until my
face was nestled in his pubic hair. After a moment, I slowly moved my
head up and down in place, his cock filling my throat and mouth utterly.
I gradually brought my head up until he was back in just my mouth, then
proceeded to suck hard as I moved him in and out of my mouth. His breath
turned quicker and more shallow, and I felt his body tense and heard him
say, "Oh god - oh fuck - I'm about to come!" . I sucked hard on the head
of his cock, taking him about two inches into my mouth, and gently worked
at the head with my tongue. After a moment, his cock jerked upward and I
felt a gout of warm, salty cum hit the back of my mouth and tongue. Out
of instinct, I swallowed and kept sucking and licking, swallowing again
and again as he shot repeatedly into me. I slowed and grew gentler as the
cum lessened. I took him in my hand again, slid my mouth off of him with
a popping sound, and licked at the head to get any cum that remained. A
small amount dribbled out of the top, and I gently squeezed his cock,
milking what was left out as well. I looked Alex in the eyes, and with
one languorous stroke of my tongue, I removed the last and swallowed it.
A small amount had gotten on my index finger and thumb, so I drew them to
my mouth and licked them off one by one, letting the nail of my index
finger hang seductively on my lip.
He helped me to stand up, and, with his hand in the small of my back,
pulled me tight against his body. We were each covered with a thin sheen
of sweat, which mingled together in our embrace. I caressed his cheek and
pulled his lips to mine for a tender kiss. After a long moment, he said,
"That was the most amazing blowjob I've ever had - you are incredible."
"I came much more quickly than I wanted to, so you're no slouch either,
Alex." I playfully nipped at his lips. "Next time, don't make me get so
wet or cum so quickly."
He smiled and said, "I'll do my best. It's tough not to get carried away
with how incredible you look, and how much fun you are, and how much I
enjoy being with you."
I blushed. "I think I could cum just looking at your naked body, so I'm
right with you there. And I've had a lot fun with you too. I've really
enjoyed getting to know you so far." I kissed him on the lips, gently.
He nodded toward the bed. "Want to join me?"
"I'd love to. Let me just get cleaned up a little first." I took my shoes
off and went into his bathroom, which was nearly the size of my
bedroom(!), and washed off all of my makeup. I also gargled with his
mouthwash for good measure, before heading back out into the bedroom.
Alex was walking back into the room, rubbing his face with a damp cloth.
God, his body was magnificent. His torso was a super-hot V-shape from his
chest down to his waist, and his back was similarly proportioned, leading
down his tight, fine ass. He walked over to the bed and sat down, naked,
and patted his lap. I climbed up on the bed and crawled over and sat on
his lap, draping my left arm around his back. He took my cheek in his
hand and kissed me tenderly, then, using his hands, guided my body into
the space on the bed between his outstretched legs.
I was facing away from him, and felt him place his strong hands on my
upper back. He began massaging my shoulder blades, which felt divine.
After a few minutes of rubbing my shoulder blades, his hands came up and
began to rub my shoulders. I rested my arms on his legs, my nails idly
tickling his thighs. After a moment, he slid his arms around my waist and
held me tight against him. I moved my hands up over his. He held me for
several minutes in silence, my head resting against his shoulder. He
raised one of his hands and turned my face up to his, and he leaned
forward and kissed me, first gently, then with increasing passion. As he
did, he shifted that hand down to cup my breast, and brought the other
hand down to my crotch, where he began to gently run his hand around my
upper thighs.
After a moment of teasing, I placed my hand on top of his and moved it
firmly over my pussy. I shifted my fingers between his, and began
fingering my clit. He followed suit, with long, gentle strokes. The
combined effect of the kiss, his fingers teasing my nipple, and our
mutual fingers on my clitty was intoxicating. My body began to shudder as
I felt a wave of pleasure rise within, and then suddenly abate. I
realized he had stopped fingering me. I opened my eyes to see his looking
into mine, and he said, "I figured I'd try to not make you cum so quickly
this time."
"Mmm, you tease."
He began fingering me again, taking me through several rising and falling
cycles, repeatedly just up to the edge of climax. Finally, I said, "I
can't take much more."
"Do you want me to make you cum?"
"Oh yes"
"Are you sure?"
"Fuck yes."
"I want to hear you say it."
"Mmm, you naughty boy, make me cum."
"I dunno, I'm having a pretty good time this way.", he said with a smile.
"Alex, please, I need you to make me cum. It feels so good."
His finger, which had been lightly stroking the outside of my lips
returned to my clit, with long, slow strokes. As my body approached sweet
release, he quickened his pace in time with my accelerating breaths. Just
then, I came, hard, and kept coming for what felt like half a minute, my
body stiffening, my toes curling. I let out a long, low moan of absolute
pleasure, before falling limp in his arms, where he held me silently,
gently caressing my skin. After several minutes, I shifted out from
between his legs, over to his side, where I kissed him on the lips and
said, "Well you're certainly a good listener!"
"I love a good challenge, and I loved seeing you squirm like that." He
kissed me then. "You tired? I'm pretty beat."
I kissed him gently. "You've taken what energy I had left. I don't think
I could move."
"Then don't," he said, lowering my head to his chest, his arm cradling my
back and resting on my hip. I drowsily placed my left hand on his chest
and fell asleep, the sound of his slow, steady breaths in my ear.
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