Teaching Bailey

by Smith, Crystal G.

She gasped as cock filled her, first from the soreness, then from the burning deep inside. “Please, Sir.” She begged. She felt like she was already walking the thin line of orgasm bliss.

  “Not yet.” He chuckled.

  She groaned. She couldn’t take waiting. It was right there. She could almost feel it wanting to burst free.

  “Please, Sir. I’m begging.”

  “Mm-mm, you know what I want?”

  “No, but I sure and the hell know what I want!”

  “I’m hungry.” He pulled his cock free from her, stepping of the bed, he walked naked out the door.

  Bailey laid there wondering what in the hell had just happened. How could he start something like that and then just walk away like it was no big deal?

  Grumbling she rolled out of bed, and headed for the shower. She was going to need a cold one if she intended on leaving the room today.

  Showering quickly, she stood looking at her suitcase. What in the hell was she supposed to wear today? He hadn’t told her she should dress a certain way or anything, so she opted for of course the sexy underwear she now had, and a pair of jeans with a t-shirt.

  Dressing quickly, she went back in to the bathroom and began looking at herself in the mirror. She shook her head. There was no way she would be able to do what they had done yesterday. She didn’t even know where to begin.

  She reached inside the makeup bag and starting pulling stuff out. She knew the basics, but it was the eye shadow that had her stumped. She put everything on to the best of her ability, minus the eye shadow, blow dried her hair, and then brushed it out.

  To her amazement, her hair was just as beautiful as it was yesterday. And she hadn’t done a bad job on her makeup either.

  “What do you see?”

  Bailey jumped, turning around to see Cole standing there. “I see me, but not me.”

  “Oh, it’s you alright. You are beautiful and sexy and you will tell yourself that every time you look in the mirror, starting now.”

  “You want me to look in the mirror, and talk to myself?” Her brows arched. Is this guy crazy?

  “Yes. I am not in the habit of repeating myself, do it.”

  Her eyes fell to his lips that were tense. His jaw was tight, his eyes were serious. Slowly she turned looking in the mirror, she felt totally ridiculous.

  “I am beautiful and sexy.” She mumbled.

  “No. Tell yourself like you mean it.”

  She growled. “I am beautiful and sexy and I mean it.” She hadn’t intended on it to come out as sarcastic as it sounded.

  “One. Now do it again.”

  She spun around quickly. “I don’t feel sexy and beautiful. I don’t look like that.”

  His face tightened. “You do look exactly like that. You are very sexy. The most beautiful woman I have ever seen and you will quit thinking of yourself as anything other.”

  “You think I am the most beautiful woman you have ever seen?” She hadn’t intended on the burn of tears, but no man had ever said those words to her. No person had ever told her she was beautiful.

  “I am not in the habit of lieing. Now you can turn around and repeat those words to yourself and then meet me downstairs for breakfast.”

  “Yes, Sir.” A smile spread across her lips and she thought she had seen a hint of a smile on his before he turned and left.

  Taking a few deep breaths, she turned back to the mirror. “Ok. You are beautiful and sexy. You are beautiful and sexy. You are beautiful and sexy. Not convinced but he thinks so.”

  She chuckled before heading downstairs and for the first time taking in her surroundings. She hadn’t noticed the stair case curve before. Slowly she walked down, feeling the smoothness of the dark wooden rail.

  She stopped, looking at the multiple pictures on the wall. They were that of book covers. All personally autographed by a Susan Shelton. The covers were sexy the characters on them were just as attractive as the cover. Sensual and beautiful at the same time. If she were a reader, the cover alone would have been enough to get her to purchase them.

  As she rounded the corner, she saw her then. Susan Shelton was a beautiful woman. An autographed picture hung there.

  Cole with all my love, Susan

  She stopped looking at her long red hair, pale complexion and absolutely beautiful, and breath taking emerald eyes. The woman was amazing.

  “Now that is beautiful.” Bailey whispered.

  “I couldn’t agree with you more.”

  Bailey looked down at the foot of the stairs where Cole now stood.

  “Come.” Cole said before turning and heading off around the staircase, in the direction of the kitchen. Or so Bailey assumed.

  She followed quickly, not wanting to get busted looking around again. As she walked in, the kitchen was spectacular. State of the art appliances, all sterling silver and shining brightly.

  She felt completely out of place here. This was nothing like she had ever seen in person, much less ever cooked on.

  “I eat breakfast every morning between 8 and 8:30. I expect it to be ready by then. I drink my coffee black, and I never have the same thing twice in one week. Now, with that being said, I eat simple. I don’t expect a five course meal, but I do expect it to be edible.”

  “Wait, I’m sorry. Why are you telling me this?” She really didn’t care how he ate. Obviously by his appearance, he worked out and ate right or he only genes that people dreamed about.

  “Because you will be cooking my breakfast, lunch and supper each and every day. I am not a picky man. I am allergic to blueberries, so we can’t have that. Keep in mind, what you fix me, will be your meal as well.”

  Her jaw dropped. What was next, dusting and laundry?

  “I’m sorry, how is this part of it?” She watched his brow raise.

  “Two. Because you are here to learn to please your Dom. It would please me greatly if you were to cook for me. Not to mention, if you don’t know how to cook, then I need to teach you, so that your next Dom will be pleased.”

  “I know how to cook. I don’t understand what this has to do with it, but ok. So are you ready for your breakfast now.”

  “Three. Yes.”

  “Three what?!” She was irritated and left high and dry and not in the mood for games.

  “Four. I do believe you are forgetting something.” His lips turned.

  “Fuck!” Her hand came crashing down over her lips. She had never in her life said a curse word out loud before now. Her cheeks heated as embarrassment filled her. She didn’t know what to say next, so she walked over to the fridge, opened it quickly, reached in and grabbed two Greek yogurts and placed them on the table.

  Not chancing a look at him, she kept her eyes down and asked, “Spoons, Sir?”

  “In the drawer directly in front of the coffee pot.”

  She could hear the amusement in his voice. She grabbed two spoons and quickly took her place at the table, sitting down. She didn’t touch her yogurt yet. She waited for him to sit and then she opened it. She ate quickly, hoping the sooner she got out of the kitchen, the quicker she could get her foot out of her mouth.

  When she finished her yogurt, it was then that she noticed that he hadn’t touched his. Still not daring a look, she asked, “Is something wrong?”

  “Do you wish me dead?” His tone was flat.

  Her head jerked up, “No! Why would you say that?”

  “Blueberries.”

  She looked over at his yogurt and low and behold, it was blueberry.

  “Oh! My! God! I am so sorry.” She jumped up feeling even more embarrassed now and went back to the fridge, taking the yogurt back. She opened and looked through them. Then it hit her.

  “If you are allergic, why do you have all blueberry flavored?” She turned, questioning him.

  “My sister visit’s often, it is her favorite. I myself don’t eat yogurt of any kind.”

  “Oh.” She turned looking back in the fridge. “What would you like then?”

  “Luc
ky for you, I think a bowl of corn flakes with banana slices will do this morning.”

  After he showed her where everything was, she sat waiting him to finish. He stood taking his bowl to the sink, rinsing it, he took his dishes and her spoon and placed them in the dishwasher.

  “So, let’s talk about what you are doing wrong this morning all ready, shall we?”

  She groaned. “Yes, Sir.”

  “One, that is the first time you have addressed me correctly. Two, you didn’t listen to what I was saying. Three you have on entirely way to much clothing.”

  Her head popped up, eyes shocked. “What?”

  “All of that sexy lingerie that you brought with you, appealing as it is, won’t be in use while you are here. You can wear panties, but that is it. There is a pair of black high heels in the closet in your room. You will wear them while you are not sleeping or I say otherwise.”

  She smiled. “You’re joking right?”

  “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.”