Teaching Bailey (6 page)

             
“Do I look like I am joking?”

             
No he didn’t.  He looked very serious.

             
“No, Sir.”

             
“Good.  Now stand and strip.”

             
She stood undressing slowly.  It wasn’t like he hadn’t seen her last night, or this morning.  But the fact was, it didn’t make it any easier.  She let each article of clothing drop to the floor until she wore nothing but the color red on her cheeks and red thong.

             
“When you begin your formal training, your attire will be much like here.  You should get used to exposing your body.”

             
“Yes, Sir.”  She knew that.  Or did she?

             
“We are having company tomorrow and you will need to be prepared for that.  Come to the table and lay your chest flat against the wood.”

             
She kept her eyes down as she made her way to the table.  She leaned over, pressing herself to the coolness.  She shivered as she laid flat.

             
“Tomorrow will be a trying day for you.  I feel that it is important to start with this soon, as you will experience it daily starting tomorrow.  I want you to be accustomed to it.”

             
“Accustomed to what, Sir?”

             
“You will see.  Spread your legs and push your ass in the air.”

             
She was hesitant but did as he wished.  She felt completely at his will. 

             
His fingertips caressed along her back, drawing little circles around and around.  First between her shoulder blades then to her sides, and stopping at the small of her back. 

             
“You have flawless skin.  You should show it off more.”

             
“Yes, Sir.”  She worked hard at trying to keep her breath steady, confused as to why his touch was stimulating responses to her pussy.  She should be irritated at the way he was ordering her around, but she wasn’t.  Not now anyways.  Irritation seemed to leave her the minute he touched her.

             
“I want you to close your eyes and relax.  Trust me.  Open yourself to me.  Let me give you the pleasure that I want to.”

             
“Yes, Sir.”  She whispered.

             
It was then she heard the pop of a tube, and the coolness to her anus.  She stiffened.

             
“Relax.  I am not going to fuck your ass.  Not yet.  But it will happen and soon.”

             
She willed her body to let go of its restraint.  To take what he was offering her and to trust him.

             
His finger smoothed the cool gel over her anus, pressing in slightly, each time allowing more of his finger to enter her, and pushing the get easily inside.

             
“When I push in, I want you to blow out and bear down a little.  It will make it easier on you.”

             
“Yes, Sir.”  She felt her body begin to tighten, then she felt something cold and hard against her, and she blew out her air, and did exactly what he had instructed her to do.  The object slipped easily inside her, making her gasp at its sudden invasion.

             
“It doesn’t have a romantic name, but it will be handy.  It’s called a butt plug.”

             
She didn’t say anything.  She was still wrapping her mind around what was in her ass.  It didn’t exactly hurt, but it wasn’t exactly comfortable either.

             
“I want you to be ready when I take that ass later, as for right now.”  His finger dipped down low, running over her drenched pussy.  “Your body likes it so far.”  He teased.

             
She closed her eyes as he showed her his finger and the excitement from her cunt.  She couldn’t believe it.  Her body betrayed her no matter how wrong she felt this was.  She felt like a prostitute in a sense.  After all, she would pay for the school, which in turn would teach her about sex. 

             
“What is that wheel in your head spinning for?”  He asked, full of concern.

             
“Nothing I can’t handle, Sir.”

             
Could she handle this?  She wanted to.  She wanted to be able to have a life.  She wanted to have the life that her friend has, and if this was the way she was going to have to do it, so be it.  For now anyways.

             
“I won’t make you answer me, but just so you know, I am a more lenient instructor.  There are those that will make you answer them.  Trust and believe there are ways.”

             
He thrust a finger inside her cunt then, pressing down exactly where she craved the most.  Her g-spot.  Her clit began to throb, her pussy began to contract and just like that she felt her orgasm burst free.  Her pussy clamped down on his finger as she cried out in pure erotic bliss.

             
“You get that one for free, but now it is my turn.”

             
She heard the zipper of his jeans and then the tearing of a wrapper.  She felt him slowly begin pressing in to her.  She gasped at the fullness she was filling.  Between his huge cock, his thick girth, and the butt plug, she felt as though she were stretched to her limits.

             
“I want to hear your pleasure.  Don’t bite your lip, or muffle your cries.  It pleasures me knowing that I am pleasuring you.”

             
“Yes, Sir.” 

             
She moaned as he began thrusting.  She could feel the circular motions of his hips and his cock rubbed her inside walls, bringing her to another orgasm.  Her pussy began to tighten.

             
“No.”  He pulled out of her.  “You will not come this time.  In the future, you will ask my permission first.”

             
“Oh, Jesus!  What is it with you leaving a girl hanging?”

             
He laughed.  “Hanging isn’t something you have felt yet.  But I will work that in to our plans, that way in the future you know exactly what ‘hanging’ is.”

             
“Yes, Sir.” 

             
Shit, she thought.  Now she had done it.  She could almost hear anger in his voice.  Sure he had laughed, but even that had sounded strained.             

             
He quickly thrust back inside her, not taking any tenderness to it at all.  He was rough with her as he thrust inside, filling her with himself until he was balls deep and coming deep inside her and moaning through his release.

             
She heard his breathing become more steady and soft.  His grip on her hips, softened from the tight grip he had. 

             
“Now, I could leave you as you are, or I can do this.”  His finger snaked down between her legs and with a tight pinch, she came.  Gasping as the unexpected hit her. 

             
“Ah….  Oh. My. God.”  She could hear his chuckle, but her body remained tense.

             
Slowly he slipped from her, but remained behind her.  His hands messaged her back and she felt herself relaxing and taking deep breaths now.  “You hold your breath when you orgasm.  We have to be careful with that.”

             
“Mm-hm.”  She didn’t care about being careful now.  The only thing she cared about now was soaking in tub and taking a nap.  Something in her told her, he had other plans though.

             
She heard him walk away, and then the zipper on his pants again. 

             
“Let me help you up.”  He offered.

             
“I don’t think I can move.”  She didn’t think she could.  She lay on the table now like a limp noodle. 

             
Quickly, he scooped her in his arms and held her against his chest.  “You don’t have to move for what is next.”

             
She didn’t say anything as he carried through the house and out the front door.  Horror struck her as she thought about someone coming up.

             
“Don’t worry.  No one will disturb us.”

             
It was as if he had read her mind.  Like he already knew her body responses, her thoughts, everything.  She laid her head then against his chest as he continued to carry her to the side of the house.

             
“I thought we would enjoy a swim now and get to know each other better.”  With that being said, not another word came out of his mouth, before he jumped in the pool, still holding her.

             
She screamed the minute she picked up on his intentions, but it was too late.  She came up gasping for air.

             
“You jack ass.  What if I didn’t know how to swim?”  She stared angrily at him.

             
He smiled.  “Guess it’s a good thing I can.”  He skimmed his hand across the water, splashing the water in her face.

             
“Oh. My. God. You are such a child.”

             
“You weren’t thinking that a minute ago.  Besides, needed something to wake you up.”  He chuckled.  “There won’t be any day time naps around here.  There is too much to do, and not nearly enough time to do it in.”

             
She swam down the length of the pool to the steps and sat down.  She watched as he made laps.  Like that in the kitchen hadn’t been a good enough workout.  After losing count, she called out to him.

             
“Did you bring me out here to watch you?”

             
“Yes and no.”  He said as he continued his swim.  “It would do you good to take a few laps yourself.”

             
She immediately placed her hands on her abdomen.  She wasn’t fat by any means, but the small pooch that would never leave, gnawed at her confidence.

             
“That wasn’t what I meant.  You’re going to need to build up your stamina to keep up with me.  Or any instructor for that matter.”             

             
“Oh.”  She felt herself relax.

             
She watched as he swam towards her, taking a seat next to her.

             
“Tell me why you were emancipated at sixteen.”

             
Her eyes grew and snapped in his direction.  “How do you know about that?”

             
“It’s public knowledge.  We do back ground screenings on everyone who enrolls in to our program.”

             
“Well then you should know why?”  She snapped.

             
“If I knew why, I wouldn’t have asked.  What I do know is that you’re richer than anyone I know, and you work a low paying job and barely make ends meat.  Why is that?”

             
“Well you just think you know everything now.  Yeah, I’m rich.  Only because my father is dead.  I don’t want his money, and I will never use it.”

             
“Why?”

             
“Look it up why don’t you.  You seem to find out about everything else.  I am assuming that the information you do have is confidential.  I don’t want anyone knowing anything.”

             
“You can get rid of that smart mouth.  Your record is more confidential with us than it is on the internet or even in the court system.  However, I want to hear it from your mouth.”

             
“No.”  She turned her head away from him.

             
“Hmm.”

             
“What was that about?  You going to spank me because I won’t talk about it with you?”  She didn’t even try to hide the way she was feeling now.

             
“No.  You would like that too much.”  He grinned, wiggling his eyebrows at her. 

             
“Ha.  You wanna talk, tell me something about you.”  She was still angry as hell, but she felt like this would be her only chance to change the subject.

             
“I’m very good and getting people to tell me what I want to know.”

             
“Was that a threat?”  She bit out.

             
“No.  Merely a piece of information that I am sharing with you.”

             
“Fine.  Tell me about your sister.”

             
“Well she is an author.  You noticed her work as you were coming down.”

             
“Those are hers, then?”  She almost felt relieved.  She didn’t know why, but she almost assumed that the woman was either his lover, or ex-lover.  Either way, she assumed they had an intimate relationship.