Romantic date or cheap whore fuck?

It hadn’t taken long to organise... A little chatting, fingers busy on the keyboard, flirtations exchanged, confidences built on the chat screen before moving to the telephone. Then it happened, she hesitantly said “I’ve always wanted to be a whore.” Quite out of the blue when we were considering a meeting.

“Really,” I said. “You just want to be used, paid for raw and base sexual services.”

A moment’s silence then hesitantly “Yes I’ve always wanted that. I want it to be real. I want to be used like a cheap tart. Simply someone who is fucked, fucked hard, used without caring just to satisfy animalistic urges” all came tumbling into my ear.

“Then simples...” I said mimicking the TV meerkat “We have been working up to meeting. You want that and so do I. You want to be a whore and I fantasise about picking up a cheap, no limits prostitute, to use for extremes without caring how she feels. To take what I want. To get myself off and more than once. We have this chance now, this very weekend, before we get to know each other better, to live that fantasy, make it a reality, in comparatively safely and..” I hesitated before saying slowly and deliberately “... and so wantonly depraved and raw.”

“Don’t say anything.” I rattled out before she could reply. “I’m going to ask you some questions about your favourite drinks, work, mundane things to distract you whilst your mind races through the possibilities. When I’m done you can agree or disagree. We can still proceed with a normal date... Do you understand?”

The silence was perhaps four or five seconds but it seemed like an eternity. “Okay then... Yes.” Was her surprisingly soft and hesitant reply

I rambled on for a few minutes. Found that she liked very dry martinis, chilled Chardonnay, was fed up with work, needed more challenges, was tired of petty disputes over car parking spaces under her building and a few other trivial inconsequential minutiae of her daily life.

We knew that our thoughts were elsewhere. Our voices were somewhat monotone, low-key, clearly enunciated. We knew that we were both weighing up the risks, rewards and sheer perversity of what I suggested. Would Friday bring a simple light-hearted, flirtatious date? Slowly building up to tenderness, slow kisses, tentative touching and then, if the gods of happenstance and chemistry shone down upon us, fumbling, exploring and sex. Like millions of other first daters all over the world.

We hadn’t even exchanged photographs. We knew each other’s ages, approximate heights, general look, obviously shared a sense of humour, were skittish, openly flirtatious and both felt very comfortable with all the exchanges we had revelled in up to that moment. We knew we both craved extremes and had vibrant, active and indulgent pasts.

I drew breath and finished my anecdote about a friend and his neighbour who acted like a parking warden, living his life chastising people who parked incorrectly, not in the assigned spaces or didn’t display the residents parking permit correctly on the windscreen. Mindless words that served only to give us both time to consider what we are about to do.

I hesitated for a moment, drew an audible breath and said slowly and deliberately. “It’s decision time... Friday night will be ours regardless. It will be Henry’s bar. You know it and so do I. You have the choice. Either come as you are, the Dottie I have felt so comfortable with over these past two weeks, or embrace our fantasy and become Chloe who will sell herself, without restrictions or limitations, for half a bottle of shared champagne and a £50 note.” I paused wondering how this had all snapped into place in my mind so quickly, so precisely, so fully formed. “Just listen to what I say... Think hard; this is a step into reality not fantasy and when I finish tell me who you will be at 8:30 on Friday in Henry’s."

"It won’t be set in stone, although we both know it is unlikely either will change our minds, back down or shy away." I drew another breath, amazed at the fluency with which the idea was forming unrehearsed. “I want you to know that at any time over the next 70 odd hours you can change your mind. I’ll never refer to this conversation again and we will have a laughter filled, outrageous, warm and intimate evening. All you have to say it’s who you will be, Dottie or Chloe.”

“Text me on Friday morning with the details of something that will make you distinctive so I can pick you out from the throng. I will have a small silver aeroplane in my lapel. The back bar in Henry’s is a great place for an excellent dry martini. When I see you, I will ask if you would enjoy one with me. Look me straight in the eye, tell me you want it stirred, not shaken and diluted like that idiot bond, and I will agree. Tell you what good taste you have, then ask you the question that will steal your fate for the evening.”

“Up to that very instant, that fork in the roads, you’re free to choose the path you will follow. Both routes will be delightful, both will be exciting. One darker, twisting, demanding and deliciously perverted the other broader, easily followed, though still flirtatious and full of adventure. You choose by telling me your name for the night.”

“I will happily share an evening, night, or even the weekend with whoever you choose to be. Dottie will get my full, head on, attention, flirtation and charm. Chloe will be treated like the £50 whore she has always dreamt of being.”

“So... My frolicsome, flirtatious new friend, who do you hope to be on Friday?” The phone fell silent. Only our synchronous laboured breathing troubled the airwaves between us. Seconds ticked past, the silence, in itself, was charged with eroticism and tension.

I heard a slight clearing of the throat, a deeper sharp intake of breath and then the single word “Chloe.”

The exhalation, the relaxation, the sudden rush I felt appeared to come bouncing back at me through the ether, almost a climactic moment. I steadied myself, cleared my throat, and said. “There is nothing more to say... I look forward to Friday, 8:30, Henry’s back bar... I relish buying Chloe but would be delighted if Dottie turned up. I know I can’t lose. So I leave it to you?”

“Yes... Chloe will text you on Friday morning.” She replied, her voice slightly shriller and quicker than before. “She will have thought of something appropriate to wear by then. If nothing else the next 70 hours will be filled with speculation and anticipation... Wait for my text.”

“I will. I most certainly will” I replied, my mind racing through the possibilities. “My phone will never leave me on Friday.” My brain had frozen in the sudden realisation of the pact we had made, but not quite sealed. My thoughts were racing but my tongue was tied. I lamely added “Good night, sleep well.”

“Good night.” Was all I heard as the phone clicked over to that empty, vacant sound of a disconnected call.

What a way to start!

Regardless of who turned up, Dottie or Chloe, I knew that this was going to be the firing up of something incredibly different and truly exciting.

Maybe I’ll write down how it went another day. Truth is often stranger than fiction.

Heather

Heather got a ride home from her friend's mom after the
football game. The junior varsity cheerleader said goodbye to
her friend and walked down the driveway toward the back door of
her house.
She was a vibrant, budding young lady, innocent but curious
about boys. Standing about 5'5", the high school sophomore had
long brunette hair that she was wearing in two pigtails, with
bangs swept down over her forehead. Her eyes were brown, and she
had a sweet smile.
Her 34-24-30 "B"-cup measurements made her a prized commodity
among the boys at school, but she had remained pure to this point
and hung out with a friend who had similar standards.
Heather was wearing her cool-weather cheerleading uniform
that evening, which consisted of a kelly green shell top with the
word "Lions" in white script. The shell had two thin white
stripes across the shoulders and down the sides, and it was
fitted over a tight, thin white turtleneck top with an elastic
band at the midriff.
Her skirt was also kelly green, with sixteen inverted white
pleats. On her lovely, shapely legs she wore a pair of matching
kelly green kneesocks with three thin white rings around the top.
White cheerleading shoes completed the attractive outfit.
Heather walked into the house and found her mom sitting in
the living room, reading a magazine.
"Hi, mom," Heather greeted her.
"Hey, Heather, how was the game?" her mom asked.
"We won, 24-14," she responded, sitting on the nearby
loveseat.
"Good," her mom nodded. "Oh, and Greg is supposed to stop by
in just a few minutes."
Heather smiled at her mom. Greg was the man her mom had been
dating for quite a while. He was a single, wealthy doctor from
across town, handsome in Heather's eyes and almost forty.
Heather had felt it was simply a matter of time before he asked
her mom to marry him.
"You do like Greg, don't you?" her mom asked.
"Uh huh," Heather answered. "He's nice."
"Do you think he's cute?"
"Yeah, I guess so."
"You know," said her mom, "he keeps telling me how cute he
thinks you are."
"Really?" Heather was rather surprised.
"Yes, he thinks you would be the perfect stepdaughter."
"Wow," said Heather. "It sounds like he wants to marry you."
"Yes, I think so, too," said her smiling mom.
"In fact," added her mom, "I was thinking about what would
help him propose to me sooner. You know - seal the deal."
Heather grinned.
"Well," her mom said, "since he thinks you're cute, maybe you
could tease him a little. You know - show off your body for
him."
"What?" asked Heather, quite surprised to be hearing this
from her mom, even though she knew her mom was quite liberal in
her attitude toward sex.
"Like looking sexy for him when he stops by. He'd like that.
And if a man is horny, he'll do almost anything. Like asking me
to marry him."
"How should I look sexy?" Heather asked, somewhat
embarrassed.
"Well, when he comes over, maybe you could sit a bit
carelessly and show him your cheerleading panties," her mom
plotted. "Maybe even rub against him a little, too."
Heather thought about it.
"It just seems so weird," Heather blurted. "You know,
putting the moves on my mom's boyfriend."
Her mom smiled and nodded.
"Heather, I can share a man, especially when he's very
wealthy."
"Well, if you think it would help, then okay," Heather
consented, just a bit uneasy about the idea.
Heather changed the conversation, but within minutes, both
she and her mom heard the slam of a car door.
"Greg's here," her mom said, as she looked out the front
window and walked to the door.
As Greg walked in and sat on the sofa next to Heather's mom,
he spotted Heather on the love seat.
"Hi, Heather," Gary said. His tie was loosened around his
neck, having come straight from his office.
"Hi," Heather responded coyly.
"You must have had a game today, huh?" he asked.
Heather simply nodded. She raised one of her kneesocked legs
and put her foot on the edge of the loveseat, as she scooted her
little cheerleading skirt higher on her thighs. She was sure
Gary could see her tight white cheerleading panties from where he
was sitting.
She noticed his eyes as he looked back at her a few seconds
later, and sure enough, they were riveted on the soft fabric
covering her teenaged pussy.
Heather smiled at him. Even though he was talking to her
mom, he was enamored by the young lady teasing him. Heather's
mom was also quick to notice his attention to her daughter.
"You like Heather, don't you?" her mom asked.
"Why, yes," he answered, trying to act professionally.
"It's okay, Gary, you can relax," her mom told him. "As a
matter of fact, I'll bet you'd even like to fuck her too, huh?"
Gary just looked at her mom, knowing what he wanted to say,
but didn't dare.
"It's okay, Gary," her mom said. "I'd wonder what was wrong
with you if you didn't."
"Well, I guess," he stammered uneasily.
"Go ahead," her mom cajoled. "Say it."
Gary gulped as he stared at the cheerleader before him.
"I'd like to fuck your daughter," he admitted.
Heather's mom looked at her daughter.
"Heather, would you like Gary to fuck you?" her mom asked.
Heather could only nod.
"And you're still a virgin, aren't you?"
Again, Heather simply nodded, somewhat embarrassed.
"Go sit next to her, Gary, and show Heather what it's like to
be a woman," her mom instructed.
Gary stood up and walked over toward Heather. His hard-on
jutted outward through his dress slacks, and both women
immediately noticed his erection for Heather.
He sat next to the high school cheerleader and put one arm
around her, while the other pulled her raised leg even further to
the side, fully exposing her white briefs.
Gary stroked her kelly green kneesock with the three white
stripes playfully, then rubbed down the length of Heather's
thigh.
"That's it," said her mom. "You can rub her pussy through
her panties, too."
Heather watched as his fingertips slid from her thigh to the
thin fabric over her mound and began caressing her soft pussy.
Heather purred softly as his fingers worked their magic on her.
They kissed softly at first, then more passionately as their
tongues intertwined.
Heather could feel his fingertips reach under the elastic
legband of her white cheerleading briefs, finding the hood of her
soft clitoris. He stroked it softly, varying the direction of
his rubbing pattern.
"Oh, Gary," Heather moaned, between kisses.
In the meantime, Heather's mom smiled. She knew there was no
way Gary could resist Heather's virginal charms.
"I think we should go up to Heather's room, don't you?" her
mom asked. "You'd be much more comfortable on the bed."
Heather smiled at Gary and slowly stood up, then took Gary's
hand and led him up the stairs to her bedroom, with her mom in
the lead.
Heather's mom pulled off the bedspread from her daughter's
bed, and then sat in Heather's chair at her school desk, just a
few feet away.
The two forbidden lovers stood next to the bed. As they
kissed again, Gary reached up under Heather's little green
cheerleading skirt.
The sixteen soft white pleats fanned out as he grasped her
cheerleading briefs and the panties beneath by the waistband and
tugged them down until they fell to Heather's ankles. She
stepped out of them, and he pushed the teenager down onto her
bed.
Surrounded by her stuffed animals, Heather watched as Gary's
head disappeared beneath the pleats of her little skirt. She
raised her knees and spread her legs apart as her mom's boyfriend
spread her pink pussy lips with his fingers and nestled his mouth
into her soft mound of pubic hair. His tongue lapped at her
clit.
Heather moaned as the friction of his taste buds glided over
her sensitive love trigger.
"Do you like it when he licks your pussy like that?" asked
her mom.
"Uh huh," Heather gasped.
"Then tell him."
"Oh, Gary," groaned Heather. "Keep licking my pussy."
Gary was only too happy to comply. After a few minutes of
tongue swirls and strokes, he slowly slid a finger between
Heather's pussy lips and gently pushed it inside.
"Oh, God!" gasped Heather. "That feels so good!"
Gary could feel the membrane of Heather's cherry with his
fingertip, and he carefully pushed it through. Heather grunted
as she felt him penetrate her, but the discomfort was minimal,
and soon he was pushing the full length of his finger in and out
of her love nest while licking and sucking her clit.
Suddenly, Heather's legs began trembling uncontrollably. Her
breathing intensified and she felt her body react like it never
had before.
"Oh, God!" Heather gasped. "What's happening to me?"
"Relax, dear," her mom assured. "He's giving you an orgasm.
Feels good, huh?"
Heather just smiled as a warm sensation rushed through her.
She sighed softly as Gary pulled his head back out from under her
skirt.
In the meantime, Gary's half-erect penis had grown soft.
Heather's mom was the first to notice.
"But first, Heather, before he fucks you, his cock has to get
hard. You can do that in one of two ways - you can either
massage it by stroking it with your hand, or you can give him a
blowjob. And every guy I've ever known prefers a blowjob to a
handjob."
"A blowjob, huh?" asked Heather.
"Yeah, you just put your lips around it and suck on it while
you push it back and forth in your mouth. It's just like your
mouth is acting like your pussy, except that you can use your
hand, too, while you do it."
"How do I know when to stop?" Heather inquired.
"Well, let him tell you. You want him to get nice and hard,
but if you go too long, he'll get too excited and cum in your
mouth instead."
"Cum?" Heather asked. "You mean when he shoots that gooey
white cream out of his cock?"
"Yes, dear."
Heather smiled at Gary.
"Would you like me to give you my first blowjob?" Heather
asked.
"Why, I'd be honored," he smiled.
Gary lied on the bed while Heather rolled over and positioned
herself between his legs, just as he had done to her.
Heather lifted his cock with her hand and put her lips around
it, then started her first blowjob, as her mom coached her from
the nearby chair. It took less than a minute for his cock to
harden in her sweet mouth, as her brunette pigtails bounced while
she fucked him orally. Her cheeks dimpled inward as she sucked
him stiff.
"Here's a tip, Heather," her mom suggested. "Wiggle the tip
of your tongue against the underside of his cock's head. It's
the most sensitive spot, and it drives most guys wild."
Heather pulled it out for a moment.
"Like this?" she asked, looking at Gary.
She put the head back into her mouth and flicked her tongue
all around the underside of the tip, while she stroked the length
of his prick with her hand.
"Oh, God, Heather, yeah..." Gary moaned.
"Okay, Heather, you'd better stop before you make me cum,"
Gary told her. "I'm gonna fuck you now, okay? First, I'll do it
doggy-style."
Heather laughed.
"Doggy-style?" she asked.
"Yes, just get on your hands and knees, and I'll fuck you
from behind."
Heather obeyed as he crawled in from behind her. She spread
her kneesocked legs about shoulder-width and looked back over her
shoulder as he pushed her green cheerleading skirt up high on her
tight little ass.
Gary nestled the tip of his cock against her moist pussy lips
and slowly pushed it in. The young cheerleader was able to only
take a few inches at first, but he slowly worked on her until he
was driving a full six inches into the girl.
"Your pussy is so tight, Heather," he noted. "I like that."
Heather smiled back at him, proud of herself. She looked
over at her mom, who nodded her approval as she watched her
boyfriend and intended husband fuck her teenaged cheerleader
daughter.
"How are you doing, sweetheart?" her mom asked.
"Just fine, mom."
"So how does it feel to have a guy's cock in your pussy?"
Heather just grinned.
"Really good," she simply answered, as her pigtails swayed
forward and back while Gary fucked her in her little uniform.
"Just remember, Gary," her mom said. "I don't want you
shooting off in my daughter's pussy. She isn't on birth control
yet."
"I won't," Gary promised. "Can I do it on Heather's face,
instead?"
"That's up to her," said her mom. "Heather, do you mind if
he squirts it on your face?"
Heather giggled.
"No, that's okay, I guess."
Heather loved the feeling of his cock filling her little
snatch. After several more minutes of thrusting, though, he
pulled out of her.
"Okay, Heather," he said. "Now I'm gonna do you in the
missionary position and finish off on your face, okay?"
Heather nodded.
"Just lie on your back and spread your legs wide for me," he
told her.
Heather rolled over and assumed the position. Gary lifted
her knees and kissed his way up one of her kelly green kneesocks,
then down her thigh to her pussy. Heather smiled as he pushed
her little green skirt up on her belly, fanning out the white
pleats.
As he lowered himself onto her, Heather felt his cock find
its mark, nestling between her virginal pink pussy lips. She
looked over at her smiling mom, then up at Gary.
"I'm gonna put it in, now," he told Heather.
Heather nodded, and he slowly popped the head into the
cheerleader's moist cunt. He paused briefly, then drove it in a
solid five inches, backed it out again, and then back in. With
each thrust, Gary put just a bit more into the young girl until
she was able to receive all seven inches.
As he supported himself with his strong arms, Heather looked
down and watched his fleshy spear drill into her wetness. She
had looked forward to this moment for a while, but never thought
she'd be fucking her mom's boyfriend, let alone doing it in front
of her.
"God, Heather, you're so fucking tight," he groaned.
"Is that okay?" asked the cheerleader.
"It's perfect," he told her.
The two lovers shook the bedposts as Gary drilled the girl.
Heather looked so good, decked out in her sweet uniform, as he
deflowered her. Fully dressed in her uniform without her
panties, the white pleats of her little green skirt rumpled up on
her tummy, her green kneesocks cocked wide apart with her spread
legs.
Heather could feel and hear his balls slapping her ass, as
well as the sounds of wetness from her sopping cunt. She
wondered what it would be like when he had his own orgasm.
"Aw, baby!" he exclaimed. "I'm gonna cum!"
Gary quickly pulled out and shimmied up to Heather's face.
With her pigtails spread out on the bed sheet, she smiled as she
watched him jerk his cock above her face.
"Shit!" he muttered, as he came. Spurt after spurt of frothy
white jizz geysered onto Heather's pretty face, as she closed her
eyes to keep the gooey substance out of them. Still, with her
eyes closed, she could feel his warm essence decorating her face
until it was pretty well coated. The cheerleader giggled as he
bathed her with his semen.
When she couldn't feel any more raining down on her, Heather
opened her eyes again and looked over at her mom.
"Heather, your face is a mess!" her mom teased. "How did you
like that?"
"I liked it," Heather answered.
"Open your mouth and let him feed a little of it to you. See
how it tastes," her mom suggested.
Heather opened her mouth, as Gary scooped some of the jizz
from around her lips onto the head of his cock and put in onto
her tongue, in addition to squeezing out another sticky strand of
his fluid.
It tasted quite strange to her. Not bad, but kind of a
starchy taste. She swallowed it down.
"How does it taste?" her mom inquired.
"Not bad," Heather told her. "Just different, that's all."
Gary smiled.
"Then maybe I can squirt the whole load into your mouth next
time," he said.
Heather's mom looked at him.
"What makes you think there will be a next time?" she asked.
"Because I'm gonna marry you," he said matter-of-factly.
Heather's mom grinned from ear to ear.
"Of course, you will let me fuck Heather from time to time,
won't you?" he pleaded.
"Yes, dear," her mom said. "But only if Heather wants you
to. And I'd have to get her on birth control, too."
Gary looked down at Heather, who just smiled with her face
frosted in the doctor's jizz.
"What do you think?" he asked the young cheerleader.
"I'd like that," Heather responded, with a big smile. "You
can even squirt your stuff in my mouth next time, if you'd like."

I must confess that my grandmother is a 75 year old cumslut. She tells me that a daily dose of my father's or my brother's cum....swallowed or liberally rubbed into her face keeps her young and vibrant. I think it's true. I've seen her fuck men half her age to exhaustion. Go Granny!

I made a transition, from a vibrant sexual life, to marriage, some ten years ago. It was time, I was going into my 30's, and my, now husband, is a decent man I respect, and love. Our home is filled with love and kindness, our kids are nice and well behaved, we have no financial problems whatsoever, and everything is just fine, as it is.

Now, since I am here, you would say, that there might be some dissatisfaction, and that might be true to some extent, but first, I have visited this and similar place before I even met him, and in general, there is no problem with sex, he is still a very good and generous lover, and frequency of our love making didn't slow down (maybe it did, just a bit, but that is normal).

My confession is, that recently, he asked me about my previous relationship, and I answered that I had a few. He told me than, that he had been with three women before me, and kind of went into detail of their relationships, not the sex part, and I guess he is expecting me to do the same, but I evaded the subject.

Now, he didn't say anything, but I felt he was a bit angry because I kept quiet, and now is even more pushing in that direction, and I am laughing it off with "lady never tells", but he won't stop. And, I am a lady, if you saw me on the street, the way I dress, the way I behave, talk, you would think - that is one fine lady.

The thing is, I am in a dilemma, what should I say to him, that he is my third or forth man, so, to lie, or to tell him the truth? I do not want to keep anything from him, we have a wonderful relationship with mutual trust, but this thing just made a dent in that trust, will he believe me if I lie, and will he think low of me, if I tell him the truth?

The other night, I tried to make some account, and it was a surprise to me as well, for some ten years that I was sexually active, before meeting him, I had sex with 54 different men, and I am not even sure that I haven't forgot some, plus, this number doesn't include pettings and few occasional blow jobs which never went past that.

At the time, it didn't feel as much, when you think of it, it is like, 5 guys per year on average, but added up, makes me look really, really bad, and I am not bad, I was just having fun, and I never cheated on him, and I don't intend to, nor I have the urge to do so.

If I tell him, will this shatter my image of a "lady wife"? What should I think of, first, honesty, or his image of me?

Told this to my therapist, she told me to keep my mouth shut, that such a thing can destroy a marriage, since men are egoistic and vain, so, some help guys, what would you like me to do, if you were in my husband's shoes?