Kassie's Service (3 page)

Kassie vigorously shook her head. She was a little scared
now. “No. Never. I’m only eighteen.”

“That’s right you are. It’s high time you really explored
your sexuality. Get down on your elbows. That’ll force your ass up in the air a
bit more. It’ll be easier to put in that way.”

She nodded and lowered herself down. Her fingers were
trembling again. She grasped the sheet and tried to calm herself. Joseph went
into a monologue. “It won’t hurt. It looks big, but you’ll find it goes in
smoothly with just a bit of lubricant. Which will be cold, of course. Brace
yourself.”

She did so and felt a cold dollop of the thick gel on her
anus. Joseph’s fingers probed gently at her, pushing slightly against her tight
sphincter. When he penetrated into her anus, she clenched up. “Relax,” he
ordered. “You’ll enjoy this. Most women do. All of my slaves do.” He withdrew
his finger. She glanced over her shoulder and saw him smearing more lube on the
plug. She took deep breaths and readied herself.

“This is all about relaxation. The more you fight it, the
more it hurts. Don’t fight it. Give yourself up to me like a good slave. Can
you do that Kassie?”

“Yes,” she said and hoped she could.

“Okay, here we go.” The rounded tip of the butt plug
pressed against her anus for a moment, then Joseph started pressing it into
her. It hurt for a moment. She felt her ass opening up. It felt wrong…oh so
very wrong. It hurt. He had lied to her. He kept pushing and she tried to keep
herself from freaking out or pushing back. Just as the pain level reached the
point where she was about to start begging for him to stop, the pain was
suddenly gone and the stretching sensation stopped as well.

“Did you pull it out?” she asked.

He laughed at her. “No, of course not. It’s right in
place where it should be. Don’t you feel it?”

For a moment she didn’t. The lingering pain and stretched
sensation overpowered everything else. Then she concentrated and realized something
was in her ass, like she needed to go to the bathroom. Her anus was being held
open by the stem of the plug.

“Give me your hand,” Joseph said. He guided her fingers
to explore the object in her ass. She felt the fancy green jewel covering up
her asshole. She slipped a finger under the jewel to feel the stem and the way
it was inside her.

“Oh,” was her reaction.

“It’s very pretty on you,” he said. “Let me get a few
pictures.” Out came the camera again and a few more pictures of her intimate
areas were recorded for his pleasure. “Okay, roll over and open up your legs,”
he said. “I’m going to fuck you now.”

She moved carefully, not wanting to unexpectedly expel
the plug, but it seemed to be firmly in place. She opened her legs and looked
between her legs to see Joseph taking off his clothes. For an older man he had
a nice body.

He didn’t say anything as he slipped onto the bed. She
half-expected him to shove his cock to her face, but he was already erect. A
warm-up blowjob wasn’t necessary. And then he was on her, and then he was in
her. His cock nudged open her pussy and filled her inner sheath, stretching her
nicely.

“Oh,” she moaned, not realizing she was making any noise.

“Am I hurting you?” he asked before he truly started
fucking her.

“No, no,” she assured him quickly. “I’m just so…full.
Your cock and the plug are so much.”

His face was only inches from her. He smiled. His teeth
were white with one lower incisor being just a little bit crooked. It was
charming. “Good. I’m sure you’ll find having a butt plug in while being fucked
enhances every sensation.”

“Uh-huh,” she vaguely agreed as he pushed all the way
inside her, bringing his pubic bone in contact with hers. He wasn’t shaved at
all. That was okay, she liked the way his hair tickled her cunt.

And he was right. She was full and it intensified
everything. At that moment she realized this is what it must feel like to be
fucked by two men at once: one in her pussy and one in her ass. Kassie wanted
to push out but she was certain that expelling the plug would be frowned on to
say the least. She lay there and enjoyed his fucking. His cock going in and out
of her cunt; her hands roamed his back going down far enough to clutch his ass;
he unexpectedly kissed her neck and when she turned her head he kissed her lips
and invaded her mouth with his tongue.

Her first orgasm was small and unexpected. Maybe it was
because of the plug. She knew there was a lot more going down around her pussy
and ass than normal. It was nice. Then Joseph increased the pace of his thrusts
and she felt the need to clamp down on the plug to hold it in place. She didn’t
want it to slip out. That in itself was almost enough to make her cum but she
held off another minute until Joseph grunted and emptied his balls into her
pussy. That pushed her over the edge and she shook and cried with the shivers
of pleasure that nearly paralyzed her body.

“Oh, thank you,” she whispered. Kassie didn’t want Joseph
to hear, but he did.

“You’re welcome.” Joseph pushed himself off her body and
ordered her to turn over on all fours. She did so, presenting him with her ass.
She could feel his fingers digging around her anus and once he firmly gripped
the jeweled base of the plug he pulled and eased it out of her ass.

At first it didn’t want to move. She clamped down on it
again, but Joseph was insistent and eventually the toy came out. She half
expected it to emerge with a little pop, but that wasn’t the case. Its
reemergence was silent. It hurt a bit coming out, but even in that there was a
little pleasure.

“Take it,” he said to her. “Go to the bathroom and clean
it and yourself.”

Kassie was a bit squeamish when she accepted the toy into
her hand. To her relief it wasn’t covered in shit, but just the lube with a
light amber tone. Moving quickly she did as he ordered in the bathroom. Her ass
felt oddly empty and stretched. That was good she decided.

When she returned with her pussy, ass, and butt plug
clean he asked her if she enjoyed the little torment he had put her through.

Kassie nodded her head. “Yes. It felt weird, but in a
good way.”

“Very good. We’ll have to try anal beads on you as well.
Be sure to arrive early tomorrow morning. We leave from here at eight a.m.
Remember to dress professionally.”

The next morning Kassie presented herself at Joseph’s
front door in her neatest skirt, modest heels, and button down shirt that
showed absolutely no cleavage. Her mother said she was the epitome of a
professional woman. Kassie let pass the reference that some prostitutes referred
to themselves as professionals.

“On time,” Joseph said upon answering the door. “Good.
Come inside.” She didn’t know what to expect once inside so she so started to
take off her clothes but he immediately stopped her. “No time for fun, just
lift up your skirt and drop your panties.” He closed the front door. No need to
advertise to the distance neighbors what was happening in his house.

Kassie followed his instructions and pulled her skirt up
to her waist and then lowered her pretty blue silky panties to the floor. When
she looked up he was holding her cardboard box with the “11” on the side. She
dropped her panties in the box and he then handed her a small bottle of lube
and the same butt plug she had worn the previous day.

“Put this in,” he told her with a wicked smile. “Squat down.
It’ll be easier to insert that way.”

Nervously Kassie fell to her haunches, smeared a good
amount of lube on the bulbous plug and reached down between her legs. It took
her a second to find the right hole and right angle, but then it slipped up
easily inside her anus. She stayed squatted for a minute to make sure it was
firmly in place, probing around the edge of the jewel wondering exactly what it
looked like. She realized Joseph had pictures from last night, but she wasn’t
bold enough to ask him to see them.

“Ready?” he asked her. She was still squatting pondering
her position when she realized she wasn’t wearing any panties.

“Do I get to wear any…?” Then she noticed her tiny
uniform g-string dangling off his fingers. Today it was black. Classy.

She stood up and took the scrap of cloth from Joseph and
pulled the tiny panties into place. It was large enough to just cover the jewel
of the butt plug and when she settled it into place and dropped her skirt
Joseph handed her the bottle of lube. “Put this in your purse. You might need
it.” He opened the front door. “Let’s go. Lots to do today.”

“Where are we going?” she asked. He indicated her to get
in the passenger seat of his very fancy sedan. Once he put the car in gear they
drove quickly from his suburban home into the city.

“Lots of meetings,” he informed her along the way.
“You’ll be my personal assistant today.”

She arched an eyebrow at him and he shook his head.
“Sorry. No time to play today. Serious meetings. You’ll be fetching papers,
running around being a general help to whomever has a need. None of it will be
sexual, sadly.”

“So why am I wearing a butt plug?” she asked, shifting
uncomfortably in the seat. It was one thing to have a steel plug in her ass, it
was another entirely to have it being forced deeper by sitting on it.

“Because you are my slave,” he told her.

That was reason enough apparently. Once in the city they
parked in one of the many garages, walked directly to a nearby hotel—for a
moment Kassie thought he had been teasing about the no sex need for her
today—but they went to a meeting suite and proceeded to go through a whirlwind
series of meetings that made no sense to Kassie. As far as she could determine
he was some type of financial advisor. If his business was legal or not Kassie
hadn’t a clue.

She was sent to get papers, coffee, other drinks, food,
pens, a bottle of hand lotion for a client with dry skin, extra binders from
the hotel supply closet, directions to the closest vegetarian restaurant, extra
napkins, graph paper, a custodian to empty the trash, and a hundred other minor
tasks. She had never been so busy in her life. The butt plug went from being an
annoyance to a sexual stimulant to nothing more than a vague feeling filling
her bottom. When she stopped in the middle of the day to pee after lunch it
threatened to slip out, so she removed it, finished peeing, then reinserted it
without a problem. Kassie took an odd bit of pride in that successful maneuver,
then shook her head at her strange, twisted outlook on what she should take
pride in.

The clients Joseph met with barely noticed her. She
wasn’t sure if she should be offended that older men didn’t give the pretty
girl waiting on them a second glance or relieved they didn’t give her more
pressing problems to solve.

When it was all over and Joseph drove her home to his
place he told her no further services would be needed that day. She was
disappointed. She wanted to have sex again. The butt plug had worked as a mild
stimulant all day and she felt randier than ever. Except for the exhaustion.

“Should I take out the plug?” she asked him when they
arrived at his house. She now had a twenty minute drive home in her decrepit
vehicle.

Joseph shook his head. “Wear it home. Take it out when
you get there. Leave it out overnight. You’re expected back here tomorrow
morning at nine a.m. Put it in before you leave your house.”

She nodded, got in her car, and drove home. It was just
after she reached the halfway point did she realize her panties were still in
the box in Joseph’s house.

Seeing as she was an adult Kassie’s parents gave her a
bit more privacy than before. She hoped they didn’t realize she was using that
privacy for the care and maintenance of sex toys. Once the plug was out Kassie
couldn’t resist and put herself to sleep with a nice masturbation session.

In the morning Kassie arrived on time at Joseph’s door.
The hidden key was missing so she was reduced to ringing the bell. Instead of
Joseph answering the door was opened by a woman wearing nothing more than a
small, semi-sheer bathrobe. Kassie gawked at her in surprise.

“You must be Kassie,” the other woman said. “I’m Joanie. Come
on in.”

“Where’s Joseph?” she asked. The door remained open but
Kassie didn’t move. She was in the right place, but this woman wasn’t supposed to
be here.

“He’s not here today. That’s good. We can play. Come on
in,” she said again, encouraging Kassie with a little come here gesture. She
stepped back from the door, leaving it wide, opened the closet door where the
cardboard boxes were stored. Joanie stripped off her robe and hung it on a peg
inside the closet. What little the robe had been concealing was now fully on
display. Joanie was older that Kassie, she figured that out right away. She had
a head of beautiful flame-red hair that fell below her shoulders. While all her
skin was on display Kassie’s eyes were drawn to the number of freckles over
Joanie’s shoulders, arms, and chest. The freckles went very low on Joanie’s
chest, just above her pink nipples.

The only clothing she wore was a tiny g-string like
Kassie’s. Joanie’s was green and barely hid her slit.

Reluctantly Kassie stepped inside. Joanie shut the door
and waited. “You are going to strip, aren’t you?” Joanie prompted.

“Oh. Right.” Kassie went to the closet, opened up her
box, and slowly took off her clothes. She was decidedly uncomfortable getting
naked in front of a woman she didn’t know, but since Joanie was already naked
and expected the same of her, she saw little room to argue. When she removed
her panties and plucked the pink g-string that Joseph had left for her—did he
buy them in bulk? she wondered—Joanie stopped her. “Wait. I need to inspect you
first,” she said.

“What?”

“Bend over so I can see your butt plug.  Joseph wants
confirmation you’ve followed orders.”