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K R I S T E N' S C O L L E C T I O N
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My Wager with Vanessa
by Harry Ogre (oagre7@hotmail.com)
***
An older guy wagers his gorgeous sugar baby that she
can't get a certain handsome stud to fuck her three
times. The results are quite interesting. (MF, mast,
oral, voy, cuck, huml)
***
Part One
I'm a guy in his 50's. I'm still in reasonably good
shape and like to have sex once or twice a week. Since
I'm a bachelor and live in a fairly tolerant city, I
have been seeing escorts for the last few years. And
that's where I met Vanessa. Vanessa works at one of the
city's most upscale escort agencies.
She's in her mid-30's and still has a tight body with a
delicious ass and firm little tits topped with eraser
nipples. She models professionally in fashion shows once
in a while and still draws stares and appreciative
smiles from any guy lucky enough to catch the runway
display. She's about 5'9" with legs for days, sultry
good looks and thick dark hair that falls to her
shoulders. She also has expensive tastes and that's
where I come in, I guess.
She and I hit it off from the first time I booked her.
Her photos on the escort website were mouth-watering. I
expected to be disappointed when I saw her in person.
But in fact, she looked even hotter than her gallery.
Couple that with a charming laugh and one of the most
flirtatious smiles I had ever seen and I was smitten big
time.
Even better, she seemed to like me back. We found it
easy to make each other chuckle. Shared many of the same
opinions. And we seemed to be made for each other in the
bedroom. After I saw her a couple of times through the
agency, she wrote out her cell number and email address
on a slip of paper and told me that she would like to
see me outside the business.
Of course, there was a catch. She made it clear that if
I wanted to take her out on the town, I would have to
cover the bills and our destinations would be only the
city's priciest and toniest clubs, bars and restaurants.
"After all," she purred, "quality costs money and I'm a
lot better than any of those other girls." And she was
clear that I would still pay her regular charge every
time I wanted to see her undressed or have sex with her.
"Does this mean that you'll be giving up sleeping with
all those other clients?" I naively asked.
"Don't be silly." she giggled. "You don't have enough
money to afford me full time. And besides, I'm too much
of a slut to stay with one guy. Unless he was very, very
rich and a total stud, that is." I guess a prouder man
would have turned down her offer. But I was hooked. Deep
down, I believed that I could make her care for me so
much that she would quit the escort business and end up
in a relationship with me. And to tell the truth, a part
of me actually dug the fact that she was so sexual and
such a firebrand in the bedroom.
It was difficult to ignore what she did for a living.
She often discussed her services explicitly over the
phone with her regular clients. She once explained in
exquisite detail how she was going to suck one rich
doctor's cock and swallow every drop of his semen – for
an extra hundred bucks of course. When she ended the
call, she smiled over at me and told me I was going to
have to cancel our luncheon date and drive her right
over to her client's apartment.
"But I made reservations at the restaurant two days
ago!" I objected.
"Well, I'm going to make four hundred dollars sucking
this guy's cock and swallowing his load," she replied.
"Those reservations are going to have to wait. But I'll
make it up to you. You know how you usually have to pay
twenty dollars for me to flash you? This time, I'll let
you watch me change and get ready to see my client and I
won't charge you a cent."
I hesitated for a few seconds, then accepted the
inevitable. Four hundred bucks was four hundred bucks
after all. "Okay," I shrugged. "It's a deal."
"Good." she smiled. "But no touching. You just get to
look this time. Otherwise, I'll have to charge you." I
winced and she laughed a little. "Start running my bath,
honey. Then I'll let you see me in it getting all wet
and soapy."
Vanessa was as good as her word. She slipped out of her
jeans and top and shed her bra and thong and stepped
into the bath I had run her. Then we selected a new set
of scanty lace underwear for her and I watched as she
put on a dress and heels and did her face and hair. It
took us about twenty minutes to drive to her client's
house. She kissed me briefly on the cheek and opened the
car door. "I'll be back in an hour or so." she said.
"See you then."
Funny thing, as I watched her walk in her expensive
heels into the doctor's hi rise lobby and imagined what
they were about to do together, I had a raging boner in
my pants. I parked in a side street a few blocks away
and fought down the urge to take out my dick and get
myself off.
I turned the radio on and off a few times and went over
some work assignments I needed to do. After almost an
hour, I drove back around to the doctor's condo. A
minute or so later, Vanessa walked out of the lobby and
got into my car. She had a Cheshire Cat smile on her
face and ruffled four bills in my face.
"See what your bad little girl just got paid?" she
asked. "I had to suck Doctor Goldman off twice and both
times he shot quite a large amount of semen into my
pretty mouth and down into my tight little tummy. He
also wanted to fuck me, you know. But I told him that
would cost extra and he settled for getting oral."
I was a little at a loss as to how to carry on this
conversation and fumbled. "Did you have an okay time?" I
asked finally.
"Mm-hmm," she replied. "Actually I quite liked his cock.
It was nice and thick with a big purple head. And I
didn't even mind taking his load. I washed it down with
some expensive Beaujolais."
I realized that she was looking down at my crotch as I
drove. "Harry, did I just give you a boner?" she smiled.
There wasn't too much I could say to deny her
allegation. I had another massive woody. I decided to
throw my pride away. "Do you think you can take care of
it, honey?" I asked.
"Oh my God, no!" Vanessa replied. I need you to take me
out and buy me a nice bottle of wine. I still have the
taste of Dr Goldman's cum in my mouth! You're going to
have to wait for me to get in the mood some other time."
I nodded and drove her downtown. My dick didn't subside.
If anything, it got bigger and harder. We parked
opposite an upscale bar. I was wearing dress pants and a
shirt and my wood was all too visible.
"If you think I'm going to march into a respectable bar
next to a pervert with a hard-on, you're quite
mistaken." scolded Vanessa. "Take your dick out and jerk
it for me right now. I'm going to sit here and watch. No
charge. Just don't expect me to help you out."
It was a helpless feeling. There was no way in hell my
dick was going to go down by itself. So I unzipped my
fly and took my stiff prick out and started to jerk it.
I glanced over at Vanessa. She had a smug, little grin
on her face. "Are you sure you aren't going to help me?"
I begged.
"Dr Goldman gave me all the dick I feel like handling
tonight." Vanessa said. "Your cock is your job, not
mine." I kept on stroking my dick. It was starting to
throb and I knew it wouldn't be long till I shot my
load.
Vanessa glanced at her watch. "You almost there, baby?"
she asked. "I'm starting to get a little bored. Can you
jerk faster?"
She handed me a box of Kleenex as I quickly creamed in a
massive sticky wad. I gasped and relaxed and mopped at
my sopping dong as it became flaccid. Vanessa clutched
her purse and swung her gorgeous legs out of the
passenger side door.
I stuffed my dick and a sheet of Kleenex back into my
shorts and zipped up my pants and joined Vanessa walking
into the bar.
As I put my arm around her waist, she commented, "I
guess you really like thinking about how I get it on
with other guys, don't you?"
***
Vanessa and I hung out a few more times over the next
couple of weeks. Her favorite way of spending an
afternoon was to tour the pricier, snootier shops in the
center of the city and try her luck at getting me to
open my wallet. It was Friday afternoon and I had bought
her a $100.00 oyster lunch at a patio place.
We headed over to an expensive woman's clothing store
and browsed through the departments. Finally Vanessa led
me into an alcove of fur coats. "Now for instance, I
don't expect you to buy me this," she purred. She
stroked her pretty nails over a mink price-tagged at
over $30,000.00. "I know that you don't have it in you
to gift a lady something of this value. But this...
now?"
A little fur jacket was price tagged at just one
thousand dollars. Vanessa tried it on and looked cute
and fuckable. I fantasized about seeing her just dressed
in the little jacket and nothing else and shagging her
and almost weakened. "But Honey," I recovered "I just
bought you oysters in the most expensive patio place in
town."
"I guess..." she sighed. "Well, I'll just have to fuck
some more johns, I suppose. That way, I'll be able to
afford that little jacket for sure."
She smiled at the cute sales attendant. "Maybe next
time."
***
The following Wednesday, Vanessa and I made a date to go
chill at an upscale penthouse bar downtown – at my
expense of course. It was the new "in" place for the
stockbroker set and was notorious for its high prices
and spoiled yuppie clientele.
So Vanessa had made a point of asking to be taken there.
I picked her up first at a sushi place where she had
gone for a meal with a couple of her escort stablemates.
By the time I arrived, she was already buzzed and giggly
and the leering maître d' and waiters were comping her
generously with cocktails. She waved and grinned as I
came in.
"Do you like what I'm wearing?" she asked standing up.
Her outfit consisted of a pair of thousand dollar
designer shoes and a stretchy, skin tight red mini-dress
that barely covered her pussy and perfect ass. As she
turned around, I looked for panty lines and saw none.
"Are you wearing underwear?" I queried discreetly.
"Uh-uh." She smiled. Panty lines are for losers. I just
have to sit carefully and keep my legs close together
and I'll be fine." Every guy in the restaurant must have
been eyeing her ass as we walked out together. We caught
a cab and hit the pricey penthouse bar.
It was pretty much as I expected - full of overpriced
suits and ties and testosterone. There seemed to be 4 or
5 guys for each of the women executives there. Vanessa
drew glances from almost every guy as we parked
ourselves at the standup bar. She ordered an expensive
cocktail while I bought a domestic beer.
After some sipping and chatting, she excused herself and
headed off to the ladies' room. It took her about ten
minutes for her to arrive back.
"Get lost on the way to the john?" I asked.
"No, I found the ladies room just fine," she responded.
"I got lost on the way back. But a very good looking guy
was kind enough to stop and help me find my way into the
bar room again."
She glanced across the room to a window table where 4
guys were sitting. Three of them were nondescript junior
exec types. The fourth however was clearly very tall –
about 6'4" – and athletically built. He was about 30
years old and had a strikingly handsome face. I gulped
and looked away. Even across the bar room, he exuded an
arrogant male sexuality.
"He even told me his name," Vanessa narrated. "Tony
Collins."
"How long did you two chat?" I asked.
"Only a few seconds," she pouted. "Unfortunately."
I stole another look over at Collins's table and
couldn't help thinking of him naked and powerful,
mounting Vanessa's naked cunt and fucking it hard and
deep with what was almost certainly a huge, thick cock.
I was surprised to feel my own dick getting slightly
erect at the thought. I couldn't believe what crossed my
mind next.
"Honey," I said to Vanessa "I have a little wager for
you."
"Wager?" she asked.
"You know that little fur jacket you wanted a few days
back?" I said. Vanessa frowned a little and pursed her
lips as she recalled the jacket and my refusal to
purchase it for her. "Do you think that this Tony
Collins guy would want to fuck you?"
"Oh my god!" she laughed. "He could barely keep his eyes
off my ass while we chatted. I was afraid he'd try and
grope me right there!"
"Care to put some money on it?" I asked.
"Like how?" she said cautiously.
I took a deep breath. She was going to think I was a
total pervert when she heard what I had in mind. I
hesitated. In my pants, my dick was now rock hard and I
decided to take the plunge. "If you can get Tony Collins
into bed with you three times, I'll spring for the fur
jacket. I promise."
Vanessa giggled. "And if I can't? Not that that would
ever happen. What then?"
"I fuck you three times for free," I said.
Vanessa arched her eyebrows thoughtfully. After all, it
wasn't as if she would be losing any real money if she
lost. And she appeared confident that she would easily
win in any event.
"But I have to have proof that he actually bedded you,"
I continued. "IPhone photos and video recordings. And
whatever else."
"Okay," she finally answered. "Game on. I'll give you
all the proof you need and then some."
"And if Tony Collins just walks out of the bar, you
lose. Those are the rules," I said.
"That's not going to happen." Vanessa said. She glanced
over at Collins' table and smiled slightly for a few
seconds. Then she looked at me. "Looks like you've
already lost," she said.
I caught a glance of Collins' group through the mirror
behind the bar. Collins' three bar buddies were getting
up and heading out. But Collins didn't join them. He
just stretched himself out a little and sipped his
drink.
Vanessa took my hand. "Grab your beer." She told me. I
picked up my drink and followed as she led me across the
bar towards Collins' table. He looked up at us. "Hi,
Tony," Vanessa said. "This is Harry my friend. I told
him you wouldn't mind if we sat here and checked out the
view of the city skyline. You can't see it from the bar
worth shit."
Tony shrugged and grinned. "Make yourself at home," he
said.
Vanessa scrunched in beside him and I sat across the
table. She leaned closely against Collins and pretended
to look out through the window past him.
"Wow! What an amazing view!" she said.
I nodded. "Tony must have the best seat in the house!"
Her hand disappeared under the table. I pretended not to
notice and stared rigidly at the buildings outside the
window. I was breathing heavily and my dick had suddenly
gotten hard again. Collins was looking out the window
too, avoiding any interaction with me.
"Harry," purred Vanessa "Don't you have to make a phone
call? The reception's pretty lousy in here," I'm told.
"You should call from the elevator foyer."
I hesitated. I was getting involved in the whole drama
of guessing what Vanessa was doing with her hand. It
took me a second to get up and head away.
Once out of the bar room, I stood around wondering what
Vanessa had in mind. After about 30 seconds, I felt my
phone vibrate and picked it up. There was a text from
Vanessa on the screen.
"Tony's feeling my thigh." She wrote. "What should I do
about it? Should I let him put his hand on my bare,
shaved, little pink pussy?"
I gasped with shock and sexual excitement. "Yes." I
texted back. "Does Collins know who you're texting?"
After another 30 seconds, I got the response. "Of course
he doesn't." Vanessa wrote. "Tony thinks you're too much
of a loser for me to contact right now. He doesn't know
about our little bet... He's getting so horny, Harry.
He's getting quite frantic," she added.
I figured Collins must have had as much wood as I had.
"What do you want me to do next?" Vanessa texted.
I bit my lip. I was tempted to head into the gent's to
take care of my raging erection, but there was an even
better idea in my mind. I drew a deep breath and texted,
"Can you jerk him off?"
She replied, "Would that count as one of my three fucks
with him?"
"No," I texted "I'll pay you an extra $100 if you can
get him off in the bar. I have to have proof though."
There was a pause of several seconds and then Vanessa
responded. "You're a disgusting sick pervert," she
wrote. "I need you to pay me $200 to do what you want."
"Okay, whatever," I wrote. My hand was shaking.
"You better come into the bar then, asshole," Vanessa
replied "or you'll miss the show."
I put the phone away and walked back into the bar and
over to Collins' window table. Vanessa was leaning even
more closely against him, still pretending to study the
outside scenery. Collins was staring intently outside as
well. He didn't even look over when I came in. I slid
back into my spot right opposite him.
Vanessa smiled. Her right hand was under the table and
seemed to be moving subtly and repeatedly.
"Have a nice time with your phone?" she teased.
"Yes, fine," I answered. I noticed that Collins' face
was flushed and he was trying to keep his breathing
under control. He squirmed a little in his seat. All at
once, he gasped and lurched slightly. I felt something
hit my shirt with a wet splat and run down my belly. A
piece of food from the table, I wondered. After a
second, it occurred to me that Vanessa had shot Tony
Collins' load all over my chest and stomach.
Vanessa put her hand back on the table and wiped it with
a napkin. "I guess we should be going," she said. "Harry
and I are so glad we met you, Tony."
Collins was no longer breathing heavily. He smiled at
Vanessa and pretty much ignored me. "Nice making your
acquaintance, Vanessa," he said.
As I got up, I realized that Collins had ejaculated
perhaps the biggest, thickest load I had ever seen in my
life. It had soiled almost my entire shirt front and
trickled down onto my pants. I folded my arms over my
chest and walked quickly away.
"Harry," Vanessa remarked. "For god's sake, you're an
even bigger cum bucket than I am! And your dick is still
hard."
I dropped one hand in front of my pants. Luckily no one
else was in the elevator with us. I rushed out and
hustled Vanessa across the building lobby and out and
down the street to my car. As soon as we got in, Vanessa
reached over and squeezed my dick through my pants. I
groaned and gasped and shot my load into my underwear.
"I guess you're going to need a trip to the laundry
tomorrow, Pervert," Vanessa scolded. "You're pretty
disgusting when all's said and done. And don't forget
about that $200. We're going to stop at a bank machine
on the way so you don't try and wriggle out of your
little promise," she added.
My dick was still trailing cum down my pants as we drove
away. I was starting to feel embarrassed about the whole
thing and wishing that I had never laid eyes on Collins
or that bar. As we turned into the next street, I heard
Vanessa's phone ring. She took it out of her purse and
smiled at me as she answered it.
"Oh my god, Tony!" she smiled. "Oh no. Harry's such a
loser, he didn't even notice what we got up to.
Tomorrow? ... Sure, I'd love to."
END
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than a
trusted partner. 4-million people around the world
contract HIV every year. You only have one body per
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 82