Emily's Dilemma (6 page)

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The envelope sat in Emily's desk drawer
untouched for three weeks. She didn't want to look at it. She
wanted to forget about it but couldn't. Each time she went to class
in the same fraying jeans she thought of it. When she needed an
additional book she thought of it. When her friends wanted her to
join them on a Friday night it was on her mind. But when she called
her mom to learn that she lost her job at the mill was the moment
of her decision. She called Laura to let her know.

"Special Occasions, this is Laura. How can we
be of service to you today?"

"Hi. This is Emily. You deserve an answer. My
answer is no. I have to leave school and go home to take care of my
mom. She's sick and just lost her job." Emily's voice trailed off.
"I appreciate your kindness and generosity. I want to return the
money." Laura was understanding and did not try to persuade Emily.
She listened and asked questions about her mom's situation and her
voice soothed Emily's sadness. What a woman, Emily thought. She was
sincere and compassionate.

Laura finally spoke up. "Please keep the
money. You need it to get back home. It'll help with your
mother."

The next afternoon, as Emily was packing her
lone piece of luggage, she got a phone call. It was her mom,
telling her that someone had dropped off an envelope full of money.
Emily sat in silence, stunned.

"How much, mom?" Emily asked.

"Two thousand five hundred!" Her mom
exclaimed. Her mom was crying.

"Who is it from?" Emily asked.

"It only says 'From a friend' on the
envelope," she sobbed through her tears. Her mom's sobbing
increased in intensity. They were tears of release. Her mom was
letting out all the pain she had been holding onto.

"Oh, God bless that angel! God bless them!
Whoever it is, God bless them and keep them!" she exclaimed through
her tears.

While her mom sobbed, Emily's thoughts turned
to Laura. She would call Laura. She slowly closed the top of her
suitcase. Without any sign of emotion, she softly put it away for
good. She walked over to the mirror. For some reason unknown to
her, she wanted to see her own face. In the future, she thought,
she might not recognize the Emily she thought she knew.

Emily's phone rang. It was Laura. "Emily,
it's time. Your first job. One of my top clients. Write down this
information," she said. "Remember what we talked about. Follow what
I said and you'll be fine. Don't forget; your working name is
Kimber. Just Kimber. Let me know how it goes."

She showered and dressed. She was as nervous
as she's ever been. She tried to keep Laura's words of advice and
encouragement in her mind. The money that Laura provided allowed
her to buy new clothes. Laura even sent Christina to go shopping
with her. Christina knew exactly what to get and where to get it.
They got to know each other, and became friends. They talked about
everything, including their mothers. They talked about the
business, and the men in their business. Christina was a font of
knowledge, kindness, and support to Emily. Christina calmed Emily's
nerves.

The cab was waiting outside her door to take
her to her destination. She got in and didn't have to speak a word.
The driver knew beforehand. As she stared out the window of passing
brownstones, she understood she was losing her virginity tonight in
more ways than one.

She rang the doorbell of the large house.
Mitch Jr. opened the door and looked at Emily from head to toe,
saying, "You must be Kimber. Hello, I'm Mitch, Jr." Emily forced a
wan smile, shook hands, and crossed the threshold of the
entryway.

"How about a drink? I just made a gin and
tonic for myself," he offered. Emily thought it might not be a bad
idea. She had to loosen up.

"Red wine. Cabernet if you have it," Emily
responded.

"Sure do. Give me a second," Mitch Jr.
answered. He found a bottle in the immense kitchen area, pulling a
bottle out of the wine closet. Through the sliding glass doors next
to the kitchen was an opulent pool and spa area, with its own pool
house. It was very private, being surrounded by evergreens on all
three sides. She wondered where they were going to do it. He poured
a glass of the cabernet and handed it to her. He clinked her glass
with his gin and tonic.

"Here's to having fun," he said with a sly
smile. "Let's go out back." Although still early spring and chilly,
there were outdoor heaters spreading warmth. He saw her eyes had
found the hot tub with its underwater lights that changed colors
every few seconds.

"Here, let's put our stuff in the pool house.
Then a little hot tub first to relax, okay?" he said with a smile.
They walked into the pool house. It was lavishly furnished and the
lights were low. "Put your stuff here. I'll meet you in the tub,
okay?" He pulled off his t-shirt and dropped his shorts, revealing
a growing member with an unusually sized mushroom-capped head.
"Bring your wine," he added. He opened the sliding door and walked
out and into the hot tub.

Emily slowly took off her top, undid her lacy
bra, and laid them over one of the rattan chairs. She then pulled
down her pants and laid them gently over the chair. Next, she
slipped off her lacy underwear. Taking a long drink from her
cabernet, she slowly walked out through the open sliding doors and
to the hot tub. Mitch Jr. was already in the hot tub and was
positioned to watch her entrance. His eyes went up and down her
fit, naked body.

"Ohmigod," he said under his breath. He had a
full erection now that she could see as the underwater lights
highlighted his enormous penis head. "Please join me," he said. She
walked down the steps into the bubbling warm water as Mitch's eyes
took in her body at close range. The warm water felt good on her
skin. Her nipples hardened in the cool air, but relaxed in the
water. The hot tub was large, designed for a dozen people, and was
deeper than the everyday type. Mitch was standing in the middle of
the tub, the water level coming to his chest.

"Cheers," Mitch said as he clinked her glass
again. Her breasts bulged above the roiling water line. He moved
closer to her, taking one last deep gulp of his gin and tonic, and
put it on the stone tiled decking around the tub and pool. She knew
he was coming close to touch her, so she did the same–a long last
drink of her cabernet. Here we go, she thought to herself. Hands
now free, he approached her and grabbed her full breasts in his
hands, squeezing them and moving them around. Her hands, also free,
were kept out to each side, suspended at the water line. He moved
his hands around to her firm buttocks and squeezed them. His erect
penis was touching her lower belly. Its large head was out of
proportion to its shaft. He pulled her close and kissed her hard.
Mitch's hold on her buttocks became a grip. He sucked her breasts
hard. He reached down between her legs and inserted two of his
fingers. She winced. He noticed it wasn't a reaction of pleasure
but of pain. This was going to be fun, he thought to himself, and
thanked his father in his mind for this extraordinary gift.

"Let's go into the pool house and dry off,"
he commanded. She got out first and as she climbed the steps he
took in her wet, beautiful buttocks with his eyes. He followed, his
erection bouncing with each step. He handed her a towel and grabbed
one for himself. They toweled themselves off until dry. She turned
to him with an emotionless face. Her look excited him. He noticed
she kept a mental distance that excited him. He would change that
look to one of appreciation. He had had plenty of tramps and cheap
hookers who had big smiles on their faces because they were getting
fucked for money. Here was a girl who obviously didn't share the
same attitudes. He guessed she was fresh to the business and that
further excited him. How fresh, he didn't know. He was going to
find out.

He sat her down on a rattan chair with
expensive upholstered cushions. At the perfect level to her mouth,
he brought his unusual erection to it, and forced it into her
mouth. She took it with a gulping sound. She's never sucked cock
before, Mitch Jr. realized. Oh, this was going to be good. His
mushroom-capped penis stretched her virgin lips wide. He rammed his
penis in as far as he could. Emily choked and pulled back. He
entered her mouth again, forcing it into the back of her mouth.
Again she choked. He grabbed her blonde hair together and moved her
head back and forth. Her warm, wet mouth felt so good on his
member. The thought of this beautiful, young novice was
exhilarating to him and his penis grew that much harder. The sounds
of her slurping him made him moan. He was in control of her. All
she had to do was keep her mouth full of him. His moving her head
increased in speed as his moaning rose. He hadn't decided what he
wanted to do with his orgasm; he just loved this feeling. He
watched as his erect penis slid in and out of her mouth. Believing
that this Kimber had never sucked a penis before, she would then
never have had experienced the taste of semen. He thought he would
give her that education. He continued sliding his funny-looking
member in and out of her wet mouth. Each slide heightened his
pleasure. His eyes gradually closed and his head tilted up as he
approached his climax. He pulled out, grabbed his erection and
furiously stroked it. He forced his eyes open to watch himself.
With a deep, guttural groan, he released his first pump of his
thick, white cream into her face, splashing it with such force that
it sprayed in all directions. His next pumps found other parts of
her head and hair, creating different patterns. His final few pumps
were aimed intentionally at her young, firm breasts, where he
coated them with his milky emission.

He was satisfied with his work. He watched
her face for any trace of emotion. She offered none. She was trying
to breathe through the thick coat of white semen that enveloped her
face. He pushed his purplish member back into her mouth so she
could taste it. He looked closely for any sign of disgust on her
face. He saw none.

"Suck me until I'm clean, Kimber. Now," he
commanded. No longer did he want to move her head and do the work
for her. He was adamant about her doing it. It excited him. He
waited for her to move along his shaft. She eventually did, much to
his enjoyment. This is what you have to learn, he thought. I'm
teaching you how to suck cock. They should be paying me
instead.

He waited to see what she would do next. He
felt a power he never felt before. He was with a beautiful young
girl who has never had a cock in her mouth. Sure, he was as turned
on about the idea as he was ever before. He enjoyed being in the
dominant role. It was new to him. His previous sexual experiences
were usually with seasoned hookers, of which he had many. He didn't
have to teach them; in fact, he learned quite a bit from them, and
wondered how they learned. This Kimber was different, and he
realized his dad bought her for a reason. Mitch Sr. knew what he
was doing, and always watched out for Junior. Mitch Jr. couldn't
thank his father enough. He would have to tell him later, when he
got home. Or call him the next day. His father set it up so they
could be at the Senior's house. Mitch Jr. didn't know why exactly,
and wasn't about to question it. After all, it was a spectacular
house and the pool and spa area were ideal for such a tryst. There
was another reason why Senior wanted it there, but it was unknown
to Junior. Mitch Jr. led Emily to an outdoor shower where he turned
on the water until it got to a warm temperature.

"Shower off here. Here's some shampoo. Towels
over here. I'll be in the poolhouse making another drink. You want
another red wine?" he asked.

"Yes," was all she said. She had so much of
him on her face she couldn't wait to wash it off, but she refused
to appear disgusted. In fact, she remembered what Laura had told
her: "Do not let him know you're disgusted, but also don't act like
you actually like it. That then defines you as a cheap hooker. And
they will know. And your price will drop like a rock. Show no
emotion at this stage, and you will make enough money for a
lifetime. And your career does not have to be long." She loved
Laura, and thought she was one of the smartest and kindest women
she ever knew.

She returned to the pool house and Mitch Jr.
with the towel around her. She knew this would be an opportunity
for Mitch to undress her. Always look virginal or chaste whenever
you can, Laura told her. A white terry cloth towel covering her
breasts and buttocks had the desired effect on Mitch. He offered
her the cabernet, clinked glasses together again, and leaned on the
bar. She leaned too. She was a bit more comfortable now, even after
the first erect penis in her mouth, and after the first ejaculation
on her face in her lifetime. Laura showed her videos of cocksucking
and facial ejaculations. Laura wanted Emily to know what happened,
so as not to be surprised and react in a negative way. Laura taught
her how to handle when a man wants to ejaculate on a woman's face.
She taught her to close her eyes while it happened. Laura taught
her how to breathe through it. She got through this experience, as
disgusting and humiliating as it was. But now, she knew that a
funny-looking penis was going to penetrate her, and although
Laura's videos helped prepare her, she had no idea of how it was
going to feel.

Mitch Jr. spent time making idle conversation
with Emily. In fact, all he was doing was recovering from his
mind-blowing orgasm and letting his body refill whatever bodily
receptacles needed refilling so he could do it again. Mitch asked a
lot of questions, to which the trained Emily had answers or
non-answers for: where do you live, do you go to college, where do
you come from, does your parents know what you're doing, etc. Emily
offered enough to call it conversation, but no more. This kept
Mitch interested, as he was realizing this Kimber was unlike anyone
he ever met. She was young and inexperienced, but almost on
purpose. As if designed that way to meet a special need at a
special time, never to be really the same again. He began to think
he might want to see her again, but that would mean paying what
probably was a premium price, and he was still in school. He knew
his father spent a ton on her, but didn't know how much, and
probably wouldn't do it again. His curiosity with her led to a
frustration that he might never have the opportunity again with
her. He asked the kind of questions designed to skirt around the
business and privacy rules of her current career, to see where she
lived, or what school she went to, so he could see her outside of
her job and maybe make something–anything–happen with the two of
them. But such are the dreams of young males in heat.