Anal Affair

The New England autumn rain had stopped by the time I
drove the rental south on Route 95 back toward my
hotel. It was late and the taillights of the few cars
on the highway shone on the wet pavement ahead of me.
I had traveled back to my home town to visit family.
Not a particularly happy visit. A funeral, in fact.
Despite the sadness that brought us together, it was
good to see people who I hadn’t seen in so long. It
was over though, and I would fly home the next
morning.

Those thoughts occupied my mind as I drove, and I
guess I wasn’t paying close enough attention as I got
a little too close to a black BMW in front of me
before swinging around to go by. As I slowly passed I
looked over, the bright overhead highway lights
illuminating the woman behind the wheel. She looked
over, too. I thought she’d be annoyed at my close
approach to her back bumper, but she seemed to smile
as I accelerated away. I pulled back into her lane
with her headlights in my mirror.

My mind drifted off again until I got to the Airport
exit and eased off the interstate. As I waited at the
light at the bottom of the off ramp, I noticed that
the Beamer had pulled up behind me. When I made the
left onto Post Road, so did she. And she followed me
onto the street next to the hotel. And then into the
parking lot, pulling into a space about fifty feet
away. Kind of a coincidence, I thought.

I gathered up a few things, got out of the car, and
walked across the wet asphalt to the entrance to my
wing of the hotel. I heard the clicking of the Beamer
Woman’s boots following me, and as I opened the door
to enter the hotel, she broke into a little jog to
catch up. I held the door for her and walked down the
corridor to the elevator.

She was still right behind me.

The elevator door opened immediately and we both
entered. I hit the button for the third floor and
asked, “Which floor would you like?”

“I’m going to three, also.”

As the car rose, I glanced over at a fairly stunning
woman. Early thirties, I’d say. Younger than me by a
ways. Wearing glasses, a very stylish overcoat, and
shiny black boots. She stared straight ahead until
the door opened at the third floor.

“Have a nice evening.” I said, and turned down the
hall to my room.

When I stuck the card in the slot and opened the
door, Beamer Woman was about ten feet behind me.
Before I let the door close, I turned to sneak one
last look as she went by.

She didn’t go by.

She stopped right in front of the door. We stared at
each other silently for about five seconds. Her
overcoat was open at the top, and I didn’t see
anything underneath. I stood aside and allowed her to
brush right by me as she walked slowly into my suite.

She turned to face me in the semi-darkness, her hands
in the pockets of her coat. I felt a moment of
stupidity as I thought about what could be in her
hand. But her hands were empty when she took them out
of her pockets, removed her glasses, and untied the
belt which closed her coat at the waist.

My tie was loose and my jacket unbuttoned, but I was
starting to feel a bit overdressed as the soft street
light streamed through the window and revealed the
lovely, naked woman under the overcoat. Her nipples
were like pink Hershey’s Kisses on her cute little
boobs.

“My name is Ben.” I said.

“Good evening, Ben.”

“And you?” I asked.

“When I do this, my name is Shayla.”

“Why me, Shayla?”

She looked me in the eyes and said, “The why of this
is none of your business. It’s about me.” She stepped
close to me and whispered, “I think you’re gonna like
it though.”

Shayla gently put her hands on my chest and leaned in
for a kiss. It was the sweetest kiss I’d had for a
long time.

When our lips parted, she ran her hands down my body,
pressing her fingers into my abs before unbuckling my
belt and opening my pants. As my cock flopped out she
looked up at me again and slowly went to her knees.

Two strokes and I was stiff in her hand. Shayla
smiled, took me in her mouth and started a beautiful,
wet blowjob. I threw off my jacket, lost the tie and
shirt, and stood there with my hands resting on the
sides of Shayla’s head as she bobbed on my dick.

She squeezed her breasts and massaged her clit as she
no-handed the blowjob, all the while staring straight
up at me. She came up for air, and murmured,
“So�fucking�hard.”

I pulled her up to her feet, and kissed her again. No
sweetness this time, our tongues fighting for
possession of the other’s mouth. Shayla broke away,
breathing hard now, and shrugged off her coat as I
kicked off my shoes and socks and jumped out of my
pants.

When I glanced at her legs she said, “The boots stay
on. I’m not gonna be here that long anyway.”

Shayla turned and climbed onto the bed, and I got my
first look at her gorgeous, perfect ass. I reached
out and gave her a playful smack, and she spun around
quickly and said, “I hope you can hit harder than
that, Ben.”

I pushed her onto her back with the intention of
spearing her sweet, bald pussy with my tongue, but
before I could get there, Shayla grabbed me by the
hair and said, “Uhn-uh. Lie down. I want you in me.
Right�fucking�now.” In the blink of an eye she had
straddled me and slid my cock into her very wet
pussy. Shayla wiggled slowly down my dick, sinking
all the way onto me. She leaned forward, dug her
nails into my chest, and started a hard, grinding
fuck. Her hair swished across her pretty face as she
moved on me. Shayla looked so good riding my cock. I
thought that her nipples were hard when she first
opened her coat, but now when I reached up and
pinched them between my fingertips they felt like
little bullets.

Then, for the first time since she stopped in front
of my hotel room door, Shayla closed her eyes, losing
herself in the fucking. I remembered what she had
said minutes before, and gave her a very sharp spank
on the ass. Her eyes jumped open and her pussy
clenched my cock. “Fuck.” she breathed, “You were
paying attention, weren’t you?”

She smiled and kept right on fucking me. Her body
shuddered every time my hand fell and the crack of my
palm on her sweet ass echoed through the suite. She
was moving with purpose now, and the only purpose in
either of our minds was Shayla getting off.

“You’re gonna come, aren’t you Shayla?”

WHACK!

“You’re gonna fuck me ’til you come on my hard cock.”

SMACK!

Shayla’s clit was glued to my pubic bone as she
squirmed on my dick. I grabbed her by both of her
wrists and held them tightly. She suddenly sat
straight up on my cock as her body rocked with the
beginning of her orgasm.

“FfffffffffffffuuuuuuuuuUUUUCK!” I let go of her
wrists and held her tits roughly. Shayla’s awesome
ass was moving in thirteen different directions as
she came�and came�and came.

After things settled down, Shayla was resting her
body on my chest. My cock was still hard inside her.

“I’ve done this before. Three times.” she said. “It’s
never worked out quite right. Not the way I want it
to. Something always made it less than perfect.”She
put her face nose-to-nose with mine. “But this was
fucking perfect.”

Shayla climbed off my cock. I figured that it was
over. She looked at me. “Hey, you didn’t come, did
you?”

“You said that this was about you.” I reminded her.

She paused. “Yeah, well. Listen, I’ve gotta go soon,
but here’s the deal.” She walked over to her coat and
took something out of the pocket. “After I get lubed
up, you’ve got five minutes, okay?” Shayla oozed some
lube onto her palm and smiled at me as she started
working it into her little butthole. “You’re a good
boy, Ben. And good boys get to fuck me in the ass.”

Well, I almost came right there when she said that.
Shayla tossed the little bottle aside and hopped back
onto the bed. She slathered the last of the lube on
my cock. “Whoa, be careful girl.” I said.

She laughed and got on all fours. She tossed her hair
back and smiled over her shoulder. “Remember, in five
minutes I’m putting on my coat and walking out of
here.”

Now it was my turn to laugh. “No problem.”

I turned my attention to Shayla’s ass. Her wonderful,
glorious, magnificent ass. And the cute puckered hole
right in the center. I put my hard cock against her
butt, and after the head popped through, I pushed.
Not fast. Not slow. Steady. All the way in. Then all
the way back out�almost. Then in again.

Shayla moved back into my hips as I grabbed a handful
of her hair and fucked her sweet ass relentlessly.
The fingers of her right hand curled into her pussy,
my balls bouncing on her knuckles as we both went for
it. “I’m gonna fucking come again.” she moaned.

“How much time have I got?”

“One minute.”

I twisted her hair firmly and slammed my cock into
her, hard. “How much?”

“Okay! Two minutes!”

I laughed again. I was right on the edge, and all I
wanted was for Shayla to come with me.

She didn’t make me wait.

Shayla arched her back and started a low howl. I
cracked my hand on her ass again, and she kept
howling softly as her whole body shook like an
earthquake was hitting the hotel. Her perfect
butthole clenched on my cock as her second orgasm hit
us both. My balls exploded and I unloaded inside her
like a fire hose.

As promised, in two minutes Shayla had her coat on.
She gave me one last sweet kiss and walked toward the
door. She looked back and said, “See, Ben? I told you
that you were gonna like it.”

Standing by the window in the darkness, I watched as
minutes later the black BMW rolled out of the parking
lot, took a right on Post Road and headed back to the
highway, her taillights shining on the wet pavement
just like when I first saw her. Shayla never did
answer my question, “Why me?” I guess it didn’t
matter after all.

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