The Hots for a Hooker

 

Wednesday night. Class was over, dinner was done. The only
thing left to do was lie on the bed and surf through the channels
until I felt tired enough to fall asleep. Another boring night
in my hotel room. I loved my job, but, God, I hated these trips.
I was a year, maybe two, from partnership, handling
administrative and training projects, and some PR, for a major
chain of restaurants. It was a great job. But three or four
times a year, when we opened a new restaurant, I had to go out to
the site for two weeks, training managers, assistant managers,
accountants, chefs, waiters and waitresses, hostesses and all the
other employees. I taught the company policy, procedures and
requirements — a “PPR” trip. I had flown in on Sunday and would
be here for another week and a half.
I wasn’t opposed to going out and having a little fun, but
the subject matter for the first week was the more strenuous and
structured, and I preferred holding the fun off to the second
week. Besides, I was happily married and “partying” consisted of
just having a few drinks with some of the new (and anxious)
employees, but it beat sitting alone in a hotel room,
channel-surfing. Oh, there was always any number of “sweet young
things” among my students, but I was no Tom Cruise, and none of
the young women ever appealed to me the way my wife did.
Besides, what kind of example would I be setting — I taught the
sexual harassment awareness course!
My wife, Laura… Now that was a nice thought. I let my
mind drift…
Happily married almost thirteen years and the passion
between us was still so strong.
My wife and I had made sweet love most of Sunday, until it
was time for me to go to the airport. The kids were at Granma’s
for the weekend and I woke up Sunday morning with Laura curled in
my arm, her long blond hair splashed across my chest. She
smelled so good. I turned enough to bring my other hand around
and I cupped her warm breast — the skin was taut and the nipple
began to wrinkle and harden. Without saying a word, Laura’s hand
found its way to my hardening cock and began stroking it slowly.
I was rock-hard in seconds. I nibbled on her ear and brought my
other hand down to her thick patch of curly light-brown pussy
hair, caressing her clit with my finger. Laura let out a long,
low moan. She gripped my cock a little tighter and—
KNOCK! KNOCK! KNOCK!
I was shocked out of my sexy reverie! Someone was at the
door and I had no idea who it could be. Maybe it was
housekeeping to deliver the mint for my pillow.
I was a little embarrassed with the tent in my pants, so I
stood behind the door and put my face at the opening.
“Yes?” Expecting a maid, the woman standing at my door was
anything but. “What are you doing here?”
“Hi, I’m Tiffany.”
“Tiffany” was one hot looking woman. She was short —
couldn’t have been over 5’3″ but was well-rounded. I don’t mean
fat — she had all her curves where they belonged — large, round
breasts, nice hips and breathtaking legs. She was wearing black
highheels and a shiny black dress that buttoned from the neck to
the hem, with more than a button or two open on both ends. The
neckline was open enough to reveal a generous show of creamy,
white cleavage, and the hem was just high enough to show an
interesting amount of thigh. She was very cute — not beautiful,
but very, very cute. Her short hair was that popular artificial
color that’s not quite red, brown or maroon, and softly spiked
Her lipstick and lightly-applied eyeshadow matched the hair. All
and all, quite an attractive — and very sexy — young lady.
I must have been standing there with my dumb look on as I
studied her.
She tilted her head to the side, slightly (and charmingly).
“Tiffany? From the TipTop Escort Service?”
“Yes? And you want me?”
She smiled a bright white smile — beautiful white teeth
framed by that dark lipstick on her sexy, full lips. “I thought
*YOU* wanted *ME*! Didn’t you call the service?”
My brain wasn’t working and I was having no trouble
maintaining my blank look.
She tried again, very slow and gentle. “You’re not Steve,
are you?”
I knew the answer to that one. “No. Mike.”
“This is room 332, right?”
Another one I knew! “Uh, yeah, 332.” I was on a roll.
Tiffany had a little puzzled expression on her pretty face.
“Can I use your phone for a sec?” she asked.
I opened the door and pointed to the phone. If she had
asked me to pay for the pleasure of watching her walk to the
phone, I would have. She dialed a number and talked for a few
minutes. As she stood there, I had to again admire the way she
was put together — she had an exquisite body. All the better
when I looked at her face and saw that she may not have been as
young as she first appeared. I had no idea about “escorts” but
from TV drama shows I assumed they were mostly poor college girls
or bored housewives, and from the “reality” shows, they looked
like skanky old whores. Tiffany looked like she was definitely
out of school and not bored and she was as far as you could get
from skanky. She was a sexy, attractive, desirable woman.
She hung up, looked at me and said, “Idiot!”
“Problem?”
“Yeah, sorry for the trouble. It’s room 323. Thanks for
letting me use the phone.”
“Sure.”
She walked that walk to the door and was just about to
close it when my mouth began talking without any input from my
brain. “Ah, Tiffany?”
“Yeah?” She stopped and turned around. She had a hand on
her hip and her hip cocked to the side. She had this wry kind of
smile on her painted lips. Her dress was open at her legs and
her chest was sticking out. God, she was hot!
My mouth kept on going. “Ah, um, you said escort service?”
She smiled again.
I knew I was out of my league and I began to feel like a
canary at a cat convention.
“Yeah, I work for an escort service.”
“Does that mean you, ah…” I was quite the cool dude.
“That’s what it means, babe. You ain’t a cop, are you?” I
shook my head. “I didn’t think so. What would be the odds of me
coming to the wrong room and there being a cop there? So,
anyways, you interested in a little party, Mike?”
Was I? Married almost thirteen years, I had never “partied”
with anyone. Was I ready to step over the line after all those
years, because this sexy, little prostitute happened to hit all
my “turn-on” buttons at once?
“Mike? You want to party? It’s as easy as 1-2-3. A super
massage is a hundred. Great french is two, and anything you want
is three an hour. Two and three are with condom, only. Tips are
graciously accepted. What do you say? I gotta be down the hall
soon — Steve’s waiting — so you’ll have to decide quick.”
“Okay.” Did I really say that? Was I going through with
it? I guess I was. I knew I had less than two hundred in my
wallet, so my choice was easy. “I’ll take the massage.”
“Good choice, Mike. Gimme the hundred and then strip off
your clothes and lay on the bed. You won’t be sorry.”
I counted out four twenties and two tens, then I stripped
off my undershirt, socks, slacks and boxers as Tiffany watched.
I was embarrassed undressing in front of a woman who was holding
my cash in her hand, but, at the same time, I was kind of proud
of my erection — I couldn’t remember being harder than I was at
that moment.
Once on the bed, Tiffany sat down beside me and gently
wrapped her fingers around my hard dick. Her dark nail polish
made the sight even that much more sexy.
“Ooo… I see you’re all nice and hard for me, already!”
“Um… are you staying dressed?” I asked her.
“Well, maybe I can open a few more buttons, or, for another
twenty, I’ll take the dress off.”
“I’ll pay.” And I was glad I did. She stood and opened the
rest of the buttons and took the dress off. She stood there in
her heels, thigh-high stockings with a dark band at the top, a
small, lacy pair of black panties, and a matching bra, with her
boobs bursting out of the top. It was a vision I would have in
my head in my dying moment.
She knelt on the bed, with her hand on my cock and her
cleavage towards my face. She was cooing in her low, deep voice,
talking dirty. I loved it.
“Ohh… You have such a nice cock, Mike. It’s so hard and
hot. Umm… So smooth and thick. Did I make it like this? Do
you like looking at my big tits, Mike? Do you like what my hand
is doing?”
I could only moan.
I knew I wasn’t going to last long. Tiffany stopped jerking
me off and reached behind her on the bed. She looked like she
was ripping open a little squeeze pack of ketchup — like you get
at a carry-out — but it wasn’t ketchup, it was K-Y. She
squeezed the contents into the palm of her hand and then she
wrapped that hand around my cock. I almost screamed with the
pleasure. I was quickly building up to a major orgasm, and her
warm, lubricated hand had me there in seconds.
“Oh, yeah, baby. Come for Tiffany. Tiffany loves to see
your cum shooting out of your pretty cock…” on and on she
talked, until I melted into the bed.
She got off the bed and went into the bathroom. I heard her
wash in the sink and then she brought a fresh towel and cleaned
me up. Had I been a little younger, I would have had another
erection as I watched her breasts jiggle as she bent over me.
I managed to sit up as she dressed. I reached my wallet and
pulled out two more tens. “For your dress. It was worth it.”
“I aim to please, Mike.”
“You do. Where are you going?”
“I told you. I have a client waiting for me, down the
hall.”
“You really do?”
She smiled and nodded, “I really do.”
“But that was over so fast!”
She laughed out loud. “What am I supposed to do about
that?”
“Um… Nothing, I guess. I just really enjoyed it and… I
donno… Maybe I could call the escort service?”
“Sure, but how long will you be in town?”
“Ten more days, why?”
“‘Cause I’ll be freelancing this hotel on my own for a
couple of weeks. Tomorrow, a convention for doctors starts and
runs through the weekend. And next week will be engineers from
all over the country. So I’ll be around. Look for me in the
lounge — that’s where I’ll be when I’m not busy. And, here,
it’s my number, in case of emergency.”
“Oh,” I knew what she meant by ‘busy,’ and it kind of took
me aback for a moment. “Really? You’ll be working the hotel’s
lounge?”
“That’s right. Can you think of a reason not to?”
“Well… No, I guess not.”
“Well, I’m off to poor Steve in room 323. I sure hope he
wasn’t in a hurry!”
“Wait.” I took my last ten and my last three fives and
handed them to her. “You deserve a tip.”
“Thanks, sweetie.” She pocketed the money and gave me a
little wave over her shoulder as she walked out the door. I
opened the door and watched her walk down the long hall and
wished I had more cash on me.

* * * * *

When Tiffany left, I collapsed on the bed and slept until
the alarm woke me. I thought I’d be up all night, unable to
sleep, thinking about what I had just done <'had I really paid for sex?'>, but I fell asleep immediately.

THURSDAY, JUNE 20, 1996

Thinking about Tiffany stroking me and then casually running
off to “service” another client, I stroked myself to orgasm in
the shower in the morning. All day, I had fleeting thoughts of
Tiffany on the bed, her tits swaying, cooing her sexy talk and
stroking me off. To say I was distracted was an understatement.
Of course, I was blocking out the other side of this whole
Tiffany business — its possible affect on my marriage.
During one of my breaks in class, I ran to a bank and got a
five hundred dollar advance on my travel money and another three
hundred from my own account. I wasn’t going to be caught
cash-short, again. Damn the consequences, I wanted this woman
again!
That evening, back at the hotel, I grabbed a burger at the
short-order cafe, showered, changed into my best suit, and took
the elevator back down to the lounge.
The lounge was small but it was “happy hour” and the place
was packed. The bar and the tables were full. I didn’t see
Tiffany anywhere. Maybe I was too early.
I got a drink by squeezing between two guys at the bar and
found a spot against a wall and watched the room. The doctors
were in town. The ages ranged from ancient to looking too young
to be in med school. There were men in suits, but even more in
polos and khakis. There was just a sprinkling of women
throughout the room, and none of them was alone. The snatches of
conversation I heard were more often about the stock market and
golf than medicine.
I finished that drink and fought for another. I was getting
nervous that I wouldn’t see Tiffany while I still had the nerve
to approach her.
I could understand why she was “freelancing the hotel.” It
was full of men with money. I began to wonder how much money she
would make during the week; and, then, my mind moved to how she
would earn that money. How many hand-jobs, blow-jobs, fucks?
How many men? And, why did I want to be one of them so badly?

Happy hour ended and dinner time arrived. The lounge began
emptying out. I took a seat at a small table and indulged in one
of my favorite hobbies — people watching. I began wondering if
all the women were doctors or wives, or were some of them hookers
like Tiffany? Almost all of them were attractive and
well-dressed, obviously enjoying all the attention the men with
them were showing them. Occasionally, the whole table would rise
and leave the lounge, headed for dinner (or a gangbang? my mind
inquired).
By nine o’clock I had had my fill of scotch and my fill of
listening to the red-faced, bull-necked doctor sitting at the
bar. He was loud and very much in love with himself, repeatedly
telling his two companions that he was a genius in the operating
room and a better golfer than the club pro; how he made better
stock choices than his broker, and how he’s nailed every nurse in
two hospitals. What an ass.
Tired, a little buzzed, and a lot disappointed, I was just
about to stand to leave.
“Ah… There she is.” It was the braggart and he was
looking at the entrance.
Tiffany stood there in an emerald green dress that didn’t
just hug every curve, but made love to every curve of her body.
Her make-up was more subdued than the night before. She was in
lower heels and nude stockings. She exuded a professional air,
but was still so sexy, you know she couldn’t hold a job too long
without the boss begging to fuck her.
The asshole raised his voice, even louder, “Tiffany.”
Tiffany saw him, smiled and gave him a little wave as she
walked towards him.
“You’re late,” said the asshole, as Tiffany walked up to
him.
“You said nine o’clock.”
“It’s nine-fifteen.”
Tiffany batted her eyelids and let her hand stroke his arm
from the elbow up. “Gosh, I didn’t know you meant boy-time. I’m
on girl-time. I better adjust my watch. How will I ever be able
to make that up to you?”
Even the asshole was charmed, “Eh, ha ha… I’ll think of
something.”
Tiffany smiled a brilliant smile at him, “Hmm… I bet you
will!”
The asshole put his arm around Tiffany’s waist. I didn’t
miss his hand dropping down to squeeze her ass cheek. “Well,
gentlemen, it looks like I have some important business to take
care of, so, until tomorrow…”
The asshole and Tiffany turned towards the door. I got up
and stepped past a couple of tables; and, as they passed me, I
smiled at Tiffany and said, “Uh, hi, Tiffany.”
She gave me a smile and a brief glance, “Hello.” And she
and the asshole were by me. His hand now rested on Tiffany’s
ass, obviously squeezing it as they walked to the elevators. She
was leaning against him and I heard her laugh. She was going to
fuck that asshole!
God, she was such a slut!
What was I saying, she was a whore! Did I think she acted
like Mother Teresa when she wasn’t in my bed? What a rube I was!

* * * * *

I had a fitful night of sleep. The night before, I had
acted like some hormone-crazed teenager when I got back to my
room, jerking-off into the sheets.

FRIDAY, JUNE 21, 1996

That last glimpse of Tiffany leaning close to the asshole as
he grabbed his hand full of her ass… It was enough to get me
hot in the morning, and I jerked-off in the shower, again.
I went through the rest of the day by rote. I knew my
teacher evaluation marks were going down the drain, but I didn’t
care. I let the class out early, it being Friday afternoon, and
I rushed back to the hotel.
I showered and dressed in record time. I walked into the
lounge before happy hour — it was empty. She wasn’t there. The
bartender came out of a door behind the bar and asked for my
order.
Before I was half finished, Tiffany stepped out of the
women’s room and walked to the bar. My throat tightened. She
was so pretty and so sexy.
She was wearing a blue pin-striped suit with a white silk
blouse, low, dark heels, white hose, subtle make-up, and a string
of pearls. The bartender brought her a drink without her asking
for it. She looked at me across the bar and smiled.
I almost spilled the scotch out of a half-empty glass as I
rushed around the bar to sit next to her. “Hi, Tiffany.”
“Hello, how are you?”
“Good. I… ugh… I was hoping I’d see you, again.”
“Again?”
Shit! She didn’t even remember what we had done! How many
dicks were there after mine? What was I doing? Why didn’t I
drain my scotch and walk away?
“It’s not important, but, yes, we have, ah… met.”
She looked so innocent as she pursed her full lips and said
“Ohh, I remember — room 332. I like repeat clients.”
“Just so you know I know. So, like we won’t have to figure
out who everybody is. You know?” I sounded like the village
idiot’s dumb brother.
Tiffany smiled and nodded. Her hand reached out and patted
mine, “Relax, ah..?”
“Michael.”
“Sure… Mike. I knew that. Well, relax, Mike, I’m not
gonna bite you… unless you want me to.”
I smiled. I was calming down. Yeah, right — I wanted to
fuck her right there on top of the bar!
If they had replaced my blood with freon, I could not have
acted cool at that moment. “Ah, Tiffany? I’d like to see you,
again — now, as a matter of fact.”
“Okay, Mike.” She chuckled softly as she took my hand, “I
can see where you might be in need of some relief.”
I threw more than enough money on the bar for the two drinks
and we walked to the elevators. The ride up was slower and the
corridor to my room was longer than I remembered. Finally we
were there.
Inside the room, I handed Tiffany three mint-crisp hundreds.
“Anything I want, right?”
She smiled and slipped the money into her small purse.
“Well, maybe not ‘ANYthing.’ We may have to negotiate on some
things.”
I was already taking my shirt off. “Like what?”
She had kicked off her shoes and was hanging her jacket in
the closet. Her white blouse had a demur, high-necked front but
was open down the sides and in the back. The profile of her
large, bra-less tits was obvious.
“Well, I’m not all that fond of watersports — they’re
extra. Same with spanking or getting a little rough. It’s okay
to play tie-up for the regular price, though.”
I unzipped my trousers. “You do all those things?”
“Everything has a price.”
She stepped out of her skirt and placed it carefully on a
chair. She was wearing her half-a-blouse, white lace panties, a
matching garterbelt and white stockings. I could have shot my
load just looking at her and talking to her. I have never seen a
sexier woman in my life!
I dropped my underwear.
She stood there with her hands on her hips. “How much more
do you want me to take off? A lot of guys like the heels,
stockings and garterbelt look.”
That was easy to answer. “I want you as naked as the day
you were born!”
She laughed a good, loud laugh. She undid the blouse and
let it fall. Her tits were magnificent — high, firm and round!
As she bent over to unhook the garters and lower her garterbelt
and panties, her tits hung down and jiggled with her movement. I
had to grab my dick and pinch it closed.
“Forget the stockings — leave them on!”
She laughed again. Then she did a sexy pose for me. She
was a fantastic tease. She moved her shoulders as she walked
toward me and her breasts jiggled. On her right tit she had a
red and black rose tatooed a fraction of an inch above the
areola. When she dropped her panties I could see that her pussy
was completely shaved and I was amazed to see that she had a
matching tatoo there, too, just above and to the right of her
pussylips.
It was a night of firsts for me. Other than videos, I had
never seen a woman with a shaved-naked snatch and never saw one
tatooed where she was tatooed and it only added to my sensory
overload. I was afraid I was going to shoot before she even
touched me and I’d get nothing for my three hundred.
She knelt between my legs and wrapped that sexy mouth around
my cock.
“I thought you said condom, Tiffany.”
She looked up, but continued to stroke my hardness. “Let’s
just say that my intuition says you don’t do this a lot. I don’t
think I’m going too far out on a limb to say you’re safe. Are
you safe, Mike? Do you fuck around a lot on your wife?” And she
lowered her mouth around me, again.
“I’ve never cheated on my wife, Tiffany. I swear. Thirteen
years. I never cheated on Laura. Ohh! Ohh! Ohhhhhhhhh!
Ahhhhh!”
Her hand and mouth milked my cock until I was dry. She
didn’t lose a drop.
She climbed up on the bed beside me. “Okay, now with that
out of the way, maybe we can enjoy your three hundred.”
And we did.

* * * * *

Tiffany removed the condom and tied the top off.
“Why did we use a condom to do this, but not before?”
“Because it makes my clean-up so much simpler.
Unfortunately, the hour’s up. I have to get back to work!”
“Tiffany, what would it cost to have you spend the night?”
She rolled close and gently kissed my chin. “It’s a
convention weekend, Mike. More than you have.”
“Yeah, I guess. Don’t you take a break? Need a rest?”
She laughed a warm, throaty laugh. “Are you worried about
me, Mike? Afraid I’ll wear my pussy out?”
“You could do a lot of other things, Tiffany. You’re
beautiful and smart and charming. Why are you doing this?”
“Whoa, Mike! You’re getting the dreaded, and all too common
‘John’s disease.’ You want to make an honest woman out of me.
Been there, done that. I like what I’m doing, for right now.
I’ll work this hotel for a while and then I’ll take a well
deserved rest. But there’s money to be made between now and
then. That’s why I better get dressed.”
I felt like a fool, but I couldn’t stop talking, and I
couldn’t take the pathetic whine out of my voice. “You like
fucking assholes?”
“You play with the cards dealt, Mike. I’m an equal
opportunity hooker. Anyone in particular that you characterize
as an ‘asshole?'”
“That guy last night.”
“Which one?”
“Oh, shit!”
She chuckled. “I’m teasing you. Of course I know which one
was the asshole. For him, I adjusted my prices up. He wasn’t so
terrific — except he was a pretty good pussy-eater! — but he
paid me an outrageous amount in cash. Of course, what he was
really paying me for was hearing a pro, who’s been with hundreds
of men, tell him that he’s the best she ever had. Now, I have to
get dressed, happy hour will be over before I get there.”
“Did you tell him he was the best?”
“Of course!”
“Did you mean it?”
“Mike, I’m a hooker. Lying is in the job description.”
She used the bathroom to freshen up and then dressed. I was
sorry to see that tight little, bald pussy and those wonderful
tits disappear behind her clothes. As she was leaving, I handed
her another hundred.
“Thanks, Mike. You’re very generous.”
“You’re worth it. I don’t trust myself to go near my
checkbook until you’re out of the room.”
She smiled and stood on her tiptoes and gave me a soft, dry
kiss on my lips. “Bye, Mike. You’re sweet.”
Did I feel guilty? I guess I did. What would it do to
Laura if she ever found out that during the last hour, I just had
the hottest sex in my life?

* * * * *

After Tiffany left, I showered and dressed as quickly as I
could. She was at the bar, talking to an older man when I got
there. I took a seat nearby and watched them. I realized that I
was beginning to obsess on this woman — a hooker! God help me!
She was so damned pretty. She talked and laughed, and I
could tell she was making the guy think he was the only man in
the room. They took their drinks to a dark booth and sat close
together. There was some kissing and a lot of shoulder and arm
rubbing going on. At one point, the guy pulled his head away and
listened to something Tiffany was saying. When she stopped
talking, the man was still for a moment and then nodded. My
guess was that she had just explained that his charm alone wasn’t
going to get her into bed. Sure enough, they finished their
drinks and made their way out of the lounge and toward the
elevator.
My stomach did a little flip as I watched the elevator doors
close on the happy couple. She was a ‘working girl,’ and I was
just another roll in the sheets, but I was jealous of the men
with her. I had a lovely, loving wife, who was the mother of our
children and a respected high school English teacher, and I was
getting jealous of the men a whore in a hotel lounge was fucking.
How’s that for weird?
Another scotch settled my stomach, and another soothed my
brain. People were in and out in the lounge. It was Friday
night and everybody looked happy. The D-J was keeping the music
pretty mellow and low enough not to discourage talking. I had
another scotch.
A little after ten, Tiffany walked into the lounge. She had
spent well over an hour with me and two hours with her last
‘client,’ and she looked as fresh and as sexy as ever. She sat
at the bar and the bartender brought her a drink and said a few
words to her. She nodded and the bartender jerked his head in
the direction of a small man, sitting alone at the end of the
bar. Tiffany nodded again and the bartender walked over to the
sad-looking guy and said a few words to him. The guy looked at
Tiffany and nodded enthusiastically. Within minutes, Tiffany and
the guy were going up in the elevator.
Fuming to myself, I went up to my room and crawled into bed.

* * * * *

SATURDAY, JUNE 22, 1996

It was Saturday. I slept late and took my time getting
going in the morning. I checked in with a call to Laura — I
needed to tell her I loved her. To no one’s surprise, Tiffany
didn’t come up in the conversation. So, after I checked on the
family, I had the day to myself, with no obligations.
I was hungry, so I went to the hotel cafe for the breakfast
buffet. The place was empty — all the classes and seminars and
demos and tee times for the conventioneers were already in full
swing. I breezed through the paper over coffee and was on my
third cup when I heard a woman ask, “Mike? Do you mind if I sit
here with you?”
It was Tiffany! She was standing there with her full
platter, waiting for my answer. I stood and pulled the chair out
for her. As usual, she looked terrific. She was wearing one of
those curve-fitting cotton, flowered dresses. Hers came down to
almost her ankles, and she was wearing little white socks and
sneakers. Her hair was short and a pretty chestnut — I guess
she had washed the red/purple/maroon out. She looked like she
was the Pastor’s young wife!
She smiled and sat down and signaled the waiter for coffee.
“Thanks, I prefer not to eat alone. Are you a talker in the
morning, or should I keep quiet?”
“I like to talk. I especially like to talk to you.”
We talked about the weather and the hotel and the town —
nothing personal. I told her how my classes were going and she
seemed impressed, but I knew she had a talent for that.
She got up and came back with a second full platter. “I’ve
really been burning up the calories. I need a recharge.”
I knew how those calories had been burned.
After breakfast, she returned to the table with a plate of
strawberries and a scoop of whipped cream. I commented that they
looked good (her biting into the red berry looked very, very
good!) and she reached over to feed me one. I picked one up and
dragged it through the cream and held it close to her lips. She
locked her eyes into mine and watched me as she licked the
whipped cream off, before biting the strawberry.
Wow! Was she so seductive in everything she did? Who was
this exquisitely sexy creature?
A few more berries and we were both laughing. I felt that
it was a real moment between us.
Tiffany got her things together and was about to leave.
“Ah, can you wait a minute or two?” I asked.
She leaned across the table conspiratorially, “Why?”
“Because I don’t want to stand up, right now!”
She laughed that deep laugh of hers. “I know a cure for
that!”
“I’ll be here for another week. I don’t think I can afford
the ‘cure,’ today.” I wanted her to say, “Let’s just go to your
room for the fun of it!” but she didn’t.
“Just as well, Mike, I’m in the mood to shop.”
Crestfallen, I quickly decided that I didn’t want her to
disappear for the day. “Want company?”
“Do you like to shop?”
“Well, I haven’t picked-up any souvenirs for my wife and
kids, yet. Maybe you can show me the good spots.”
That was one of the happiest days of my life.
We shopped and walked and talked and lunched; and, the whole
time, I had this beautiful, sexy, vivacious woman at my side.
She drew stares from every man we were near. I think just to
tease me, we went into a fancy lingerie shop and she bought a
couple hundred dollars worth of sexy underthings, asking me what
I thought of each of them.
It was a pretty, early-Summer day, and before we headed back
to the hotel, we decided to take a boatride on the river. The
crowd was sparse and we had the back of the boat to ourselves.
Tiffany leaned her head on my shoulder. I put my arm around her.
It was cooler on the water, and we were cuddled together under a
blanket.
“This has been really nice, Mike. You made shopping for
lingerie a lot more fun than it is alone.”
“Glad I could help, Tiffany. It was fun for me, too.”
“After you got into it.”
“Yeah, I was a little embarrassed, at first.”
“If you want to get together this week, let me know in
advance, and I’ll wear your favorites.”
“That would be nice, but I don’t remember them being on long
the last time.”
She laughed. “Maybe I should make you keep your hands
behind your back and you undress me with your teeth. That way
you could appreciate the undies. You know, now that I think of
it, I should be allowed to deduct the costs for them as ‘work’
clothes on my tax form.”
I looked her deeply in her gray eyes, “You’re very casual
about it.”
She held my hand. “It’s what I do. Don’t get all bent over
it, I don’t.”
“I know, Tiffany, but when I look at you, I see a woman who
should be doing something else… something you could be really
good at.”
She shook her head, “I’m really good at fuckin’. You said
so yourself.”
“I know, I know. It’s none of my business. Sorry.”
“Don’t worry about it.”
We were quiet for a while. The boat turned around. Our
perfect day was soon to end.
I couldn’t help myself. I didn’t want to pry. I didn’t
want to piss her off, but I couldn’t help it. “How… how did
you get started, Tiffany?”
“Oh, no! The most-asked ‘John’s disease’ question. But, in
my case, that’s a good story, Mike. Do you like good stories?”
“Sure. Of course.”
Under the blanket, her hand expertly lowered my zipper and
disappeared inside my pants. Everyone else on the boat was up
front, looking at the approaching city.
“Well, actually, it was my decision. I hit puberty pretty
early, so I had a nice body from a young age. When I was twelve,
I had an unbearable crush on my cousin, who was in college — he
was twenty. On Christmas break, I let him seduce me. He was
sweet and patient and considerate, and I loved sex from that
first time. We fucked whenever we could for years — even after
he married.”
My dick was hard and sticking out of my fly and Tiffany was
stroking it very slowly.
“I got on the pill, and there was a lot of regular boy-girl
sex over the next few years.”
“A lot?”
“Yeah, a lot! Other girls my age were still giggling about
sex or experimenting with hand-jobs — I had been taught by a
wonderful lover, and the word soon got around. When I was
fifteen, my best friend’s father propositioned me. He said he
would give me one hundred dollars every time we had sex. Money
at that time wasn’t really an issue for me, but I got really
turned-on by the idea of being paid to have sex with an older
man. What could be more depraved and naughty than that?”
My breathing had changed and Tiffany noticed it, squeezing
my cock as she continued.
“Not yet, Mike!
“Anyway, I thought about it for a day or so — I didn’t want
to seem like a slut! — but, of course I agreed to do it. My
friend’s daddy was very happy. He loved my body. We screwed as
much as he could afford. A few weeks after we started, he told
me he was going out of town for a few weeks, then asked me if I
would mind if he gave my number to a friend or two of his. I
said, ‘no, I wouldn’t mind.’
“By the time I was ready to go off to college a coupla years
later, I had a shoebox filled with one hundred dollar bills and
knew almost every man at my father’s country club on an intimate
basis. What I know now, though, is that I shoulda charged those
horny old men a lot more for my underage pussy!”
She knew what she was doing. Her grip tightened and her
stroke increased. I was ready to blow.
To my surprise, Tiffany lifted the blanket and dove her head
under it! It made me so excited, she almost didn’t make it. I
started shooting my cum just as she wrapped her lips over the
head of my dick.
When I regained a little composure, I smiled at Tiffany.
“That was unbelievable! You tell one hell of a story! I
especially liked the special effects!”
She laughed as I zippered up. “You couldn’t get off the
boat with cum all over your lap.”
I looked at her. “I don’t have that kind of cash on me,
Tiffany. I can get it back at the hotel.”
She patted my cheek, “That’s okay. I had a nice day. It
was my idea, anyway. You’ll just owe me.”
As we disembarked, I asked, “What happened after you went
away to college?”
She shrugged, “Just college stuff. Then I met a guy and we
got married young. No pregnancies. No more hooking until
recently. Now, no more questions.”
We took a cab from the dock, and it dropped me off at the
hotel. I bent down to pay the fare, with enough to pay for
Tiffany.
“I had a really great time, Mike. Thanks for the company.”
“My pleasure. I had fun, too.”
She smiled that wicked smile of hers, “I hope so! Well, see
you around.” And the cab pulled away from the curb. I watched
as it made a left at the next street.

* * * * *

Back in my room, I showered and dressed and turned the TV
on. I didn’t feel like sitting in the room, so I went down to
the lounge. It was empty. I sat at the bar and ordered a beer.
I was watching a game on the TV and the two bartenders were
talking when Tiffany walked in.
She was definitely dressed for a Saturday night on the town.
She was wearing black highheels, dark stockings and a black
leather mini-skirt. On top of that was a gray, silky blouse and
a small black vest. Her hair had that punky look and color,
again, and her make-up was heavy (but flattering). She may as
well have tatooed “FUCK ME” on her forehead, because that was the
only thing a man could think about when he looked at her.
One of the bartenders disappeared into the back. Tiffany
walked down the corridor where the rest rooms were situated.
Twenty minutes later, the bartender reappeared and the other
one went through the door at the back of the bar. He came out
fifteen minutes later and gave the other bartender a discrete
high-five. A few minutes later, Tiffany walked over to the bar.
The first bartender had a drink waiting for her.
“Thanks, Brian,” she smiled.
I picked up my beer and walked around to sit next to
Tiffany. “I just wanted to thank you, again, for such a nice
day, Tiffany.”
Tiffany lit a cigarette and exhaled a long stream of smoke
— I almost wished I smoked, again — Laura and I had quit
smoking on our honeymoon.
“I had fun, too, Mike, and I don’t want to hurt your
feelings, but that was off the clock and now I’m on the clock. I
don’t want you sittin’ here and we’re gabbin’ like two old
friends. It would give the wrong impression. So, unless you’re
makin’ me an offer I can’t refuse, I’ll see you later.”
“Sure, Tiffany, I wasn’t thinking.” As I was about to
leave, I noticed something glinting between Tiffany’s breasts.
Her blouse was sheer, but nowhere near see-through, but there was
something gleaming under there.
Tiffany saw me staring and laughed. “Haven’t you ever seen
tit jewelry before?”
Stupidly, I shook my head.
Tiffany opened one button and pulled out a fine gold chain.
“Do you know what holds it up, Mike?” I shook my head. “My
nipples. An end tightens over each nipple. It’s very erotic, if
you’re in the mood.”
Just then, four guys, obviously just off the golf course,
walked into the lounge and ordered single malt scotches.
I looked at Tiffany again, and walked over to a small table,
to nurse my beer. Within ten minutes, Tiffany had been invited
over to the table with the four golfers. She joined them,
laughing and drinking.
The lounge filled up slowly. Two of the men at Tiffany’s
table left and I was making a mental bet on which of the
remaining two would go upstairs with Tiffany. I would have been
wrong either way. The three of them left the lounge and went up
in the elevator together!
I could feel the stab of cold jealousy in my chest. Why did
I care what, or who, or how many whos she did? Why did I care
about a woman who repeatedly proved to me she was the slutiest of
whores?
I left the lounge and went for a walk. I stopped in a dark,
little tavern and had a burger. I spent two hours wandering
around one of the super bookstores. And the whole time, Tiffany
was never out of my mind.
Later in the lounge, the band was playing slow numbers and I
was finishing another beer and was about to settle-up when
Tiffany walked into the room. There was a good crowd, but it
wasn’t crowded. There were a lot of couples. I guessed most of
the doctors had already caught flights out. The weekend crowd
looked like locals and tourists. I was curious if Tiffany could
lure another victim from the relatively few unattached men in the
place. I ordered another beer and sat down to watch. Maybe in
the back of my mind I had the fleeting thought that if she
couldn’t drum up any more business for the night, I’d have a
chance of a nightcap with her.
I shouldn’t have worried about her ability to lure men. A
guy at the bar lit her cigarette and they talked. He asked her
to dance. She stood up and removed her vest. As she walked to
the small dance floor, it was obvious this woman had a set of big
tits, and at that moment they were bra-free. Dancing only
emphasized that point.
They returned to the bar and another man asked her to dance.
Then another. Finally, after a slow number, the original dance
partner and Tiffany walked out of the lounge and toward the
elevators. I had to get out of there!