My head was pounding. My body was aching. I knew at any moment the contents of my stomach were going to come rushing out. I jumped up realizing where I was but I wasn't in the right state of mind to start questioning it. I was more focused on finding the toilet.
"Ughh." I groaned while kneeling in front of the toilet bowl. I stood in that position for a good five minutes before resting my head on the seat. Don't judge me, it was cool and kinda felt good on my head. I took a deep breath not wanting to open my eyes.
"You do know that's very unsanitary." A familiar voice spoke. It wasn't a surprise that I ended up here because he was the last one I seen before blacking out my only question was how did he know I was there and why was he there. Barely opening my eyes I seen Mr.August standing in the door way. He looked like he just came from a business meeting or something. He wore navy blue dress pants (I'm starting to believe that's his favorite color just saying) work shoes and a nicely fitted button up shirt that was tucked in complimented with a navy blue tie and navy blue diamond cufflinks with his initials.
I cleared my throat sitting up placing my hand over my forehead. He shook his head. He looked disappointed. I frowned remembering yesterday's events. "Mr.August I'm so-" He held out his head and shook his head. I closed my mouth feeling as if I was about to cry. Not sure why I felt emotional I quickly wiped my eyes attempting to stand. It's this hangover it's fucking with my head.
Mr.August had given me a toothbrush, aspirin and a cup of tea.
I climbed back into the spot I was in and pulled my knees up to my chest. Mr.August stood at the edge of the bed removing his tie not saying a word. I could tell he was angry and I wanted to explain to him what happened but I don't think he wants to hear it. "Not only did you stand me up when I specifically told you I would have a car waiting for you, you did without letting me know. I'm confused Jacob I really am I would ask why but I honestly do not care to hear what you have to say. I don't think you fully understand how this is supposed to work out between us, what you did actually calls for a punishment." He turned around and in one quick motion he pulled me to the edge of the bed. I bit my lip holding in a whimper.
He placed his hands on both sides of me and bent down so his face was leveled with mine. His seemly cool minty breath lingered around my nose. He examined my face licking his perfectly pink plum lips. "Maybe this wasn't a good idea." He whispered sending chills down my spine. "Maybe you're not ready." He added on frowning in disappointment.
I shook my head. "No!" I exclaimed "Mr.August I want to do this, I am ready." I said trying not to sound like a little kid pleading with his parent. I'm not sure what has gotten into me but it was something about this man that made me feel this way.
He pulled away and stood up straight. "I want this to work Jacob I really do so we're going out to dinner and from there we will get more into the details of how this is gunna go. I do recommend you get comfortable Jacob because you will be staying here for awhile seeing how I can't let you out of my sight without you going awol. I will have Justine go out and buy you something to wear right after she finishes making breakfast." Making his way to the door to exit the room he turned around briefly "You don't mind cross dressing do you?" I shook my head without actually thinking it through. A smile formed on his lips showing his sharp white canines. "Very well then, get some rest so that headache can go away. I'll be in my office if you need me." I nodded watching him walk out of the room closing the door behind him.
I threw my head back into the pillow which exactly wasn't the best idea. "ough" I mumbled rubbing my finger tips against my temples. This headache was going to be the death of me. I closed my eyes hoping once I wake up this headache will be gone.
. . .
"Jacob." My eyes fluttered open to the sound of Justines voice as she entered the room holding acouple different bags from places like Chanel , Macy, Aldo. All stores I don't typically shop at. She placed the bags on the bed next to me. I sat up against the headboard. luckily my headache was gone and I felt some what better then I did a few hours ago.
"Mr.August had given me a few tips on what I should get you but they weren't very detailed so I figured- If that's okay with you- I added some of my ideas into the clothes." She said smiling as she started to put everything she bought out of each of the bags. "He told me he was bringing you to a fancy restaurant so I figured why not get Jacob a cute little dress, some heels and a purse maybe even makeup- Once again only if that's ok-"
"Justine it's fine I'm sure I'll like whatever you got me." I said smiling at her. She was very pretty about the same height as me. She had the most flawless chocolate skin. Her body shape was amazing and her hair had so many similarities to mine except it was a bright purple. She looked about 20 so I was trying to figure out how a beautiful woman like her ended up serving Mr.August his meals and how Mr.August has gone all these years without making her his submissive. Well who's to say she wasn't at one point. The thought actually led me to want to ask how she ended up here.
"Can I ask you something?" She smiled and nodded as she started to place everything she bought onto the desk that was in the room. "How did you end up here?" I asked. She shrugged.
"How do you think?" She questioned pulling out a tiny bag from mac.
"Well were you his sub-"
"Heavens no." She laughed out loud shaking her head returning her attention back onto me. "Chresanto or as you know him as Mr.August is my cousin. He helped me in so many ways one being he paid for me to get into one of the best culinary arts colleges in the big apple since cooking was a passion of mine, he was like the brother I never had and I was like the sister he never had. After graduating I wanted to pay him back because once I got out I had been asked to become one of the head chefs in londons high class restaurants and later was asked to take over it as the owner had decided to retire. I offered to pay him back but Chresanto being so hard headed refused so I suggested since the man works so much as a way to pay him back I would come over whenever I have the day off or right before or after I got out of work and help him. Do laundry, clean, cook, go run errands just basic stuff." She explained. I nodded in shocked looking at the two I would have never guessed they were related.
"I seen my cousin probably introduced herself to you." Both our heads turned into the direction of Chres- I mean- Mr.August as he stood in the door way. This time he wasn't wearing anything businesslike. He was barely wearing anything at all to be quite honest with you. He stood leaning against the door frame with his arms folded across his bare chest. He had on grey sweatpants, and grey nike slides. Looked like he's been chilling which I didn't think he knew how to do.
Justine quickly turned around blocking what she had bought. "Yes seeing the boy was going to be staying here I figured he would want a friend." She cheesed making Mr.August laughed.
"Very well." He said trying to see what Justine was hiding.
"Stop tryna be nosey. You will see him later on. I made you lunch it's sitting on the island go eat and get cleaned up you look like you just woke up." He shrugged and stretched causing his sweats to drop just a little below his well cut out v line. I bit my lip as my cheeks started to feel warm.
"Alright child."
"You're like 4 years older than me." Justine said.
"You just turned 21 so technically 5 since my birthday is coming up." He teased. So he was 25 years old? Wow they wasn't kidding about him being young. I smiled though because the few times I been around Mr.August he's always kept a very tight posture seeing him talk to Justine was like seeing him act like a normal 25 year old.
"Very well I'm going to eat then go shower, Justine please make sure Jacob eats a full plate before getting into the shower aswell." She nodded as he walked out. He let out a loud breathe.
"He's so annoying." She laughed. "Once you get to know Chresanto you'll see there's so much more to him than what he shows. My cousin is very uptight and controlling but he has his reason."
"Like?"
"That really isn't my place to tell Jacob but I'm sure the longer you stick around the more you'll find out." I nodded respectfully understanding why Justine wouldn't tell me.
"So are you this friendly with Chres- Mr.August, submissive?" I asked curious.
She shook her head, "Before you Chresanto had one who actually lasted a few years. So I can't really say yes because before you I've only seen and talked to one." I nodded.
"Can I straighten your hair?"
What a way to change the subject I thought to myself. Whatever could she I thought , I had my hair straightened once when I was in high school but after that I never found a reason to straighten it again. Mr.August had wanted me to cross dress which I didn't really mind because I use to love dressing up in my mothers clothes as a child and even sometimes I would find my self wearing Nala's clothes. I had the body for it to besides being flat chested. I had the big ass, thick thighs, curvy waist and wide hips. I kinda was excited to see how everything would come together so I agreed to let her straighten my hair.
. . .
I was now sitting in the bathroom as Justine finished applying makeup to my face. I was dressed in a olive green column dress with cut-outs down the sides, with black lace-up pointed toe heels. I also had a Chanel hand bag. "Look." She said smiling pulling me from the stool and over to the full body mirror.
I was in shock.
I didn't even recognize myself.
Justine had truly outdone herself. The entire outfit was beautiful. She had made it so it wasn't even noticeable that I was actually a boy. The dress seemed to be meant for girls with a small chest so I wasn't really insecure about it because it was all around perfect. I felt beautiful. "You like it?" She said breaking me out of my thoughts I nodded and turned around hugging her. She chuckled hugging me back for a few seconds before pulling away to stare at me.
"Chresanto is going to fall inlove once he sees you Jay. You look beautiful and better than his last submissive. I swear Chresanto would be foolish to let you slip away." I couldn't help but blush. "I almost forgot hold on." She ran out into the room and back holding a long black velvet box. "Chresanto bought this for you." I took the box from her and opened it.
It was a solid gold chocker necklace and in the middle were the letters C.A in gold also but had really tiny diamonds in both the C and A.
Chresanto August.
I took it out of the box and put it on. Is this his way of letting the world know I'm his? I mentality shrugged.
"Now follow me." I followed Justine out of the room taking a quick glance out the window I noticed it was dark. The only light was the lights from the buildings and the moon it looked beautiful outside.
I followed behind Justine noticing the heels I had on made me a couple inches taller than her. Walking into the living area I seen Mr.August standing in front of the wall sized window starring outside with his hands in his suit pockets.
I bit my lip nervously as Justine walked over to him and tapped his shoulder they exchanged words and then Mr.August slowly turned around. The way he looked at me made me weak in the knees. I looked down as I tightly clutched the Chanel hand bag in front of me. I heard his heavy foot steps approach. I knew he was towering over me because I seen his black shiny dress shoes in front if my feet which was covered by the dress. Also I could smell his colon.
I felt his finger hook under my chin. He picked up my face so I was now looking up at him. He wasn't dressed in his usual navy blue suit this time he wore a black blazer slightly buttoned up, a black dress shirt, a black tie, black dress pants and black diamond cufflinks with his initials, he also had this black diamond clip on his tie. I looked at his face and it looked better then ever. His smooth honey brown eyes, honey kissed skin, his bright white sharp canines, his glossy plump lips and his little small curls on his head. If sex had to have a face Mr.August would be it.
"You look.. Breathe taking." He whispered while planting a gentle kiss on the top of my hand.
"Well my job here is done." With that being said Justine exited the room leaving me and Mr.August alone.
"You look vey handsome." I returned the compliment lowly.
"Your hair." He mumbled still star struck while running his hand through my hair. His hand further travel from my hair to the curve of my back to my ass. "The way you fill out this dress is amazing. Kinda makes me want to quickly get you out of it." I bit my lip and tucked a loose hair behind my hair. I felt his thumb on my lip. "I want to bite that lip of yours."
Is it possible we can skip the dinner and go right for dessert?
He chuckled, "Almost forgot I was upset with you." He wrapped his arm around my waste and lead us out.
. . .
Taking our seats at the restaurant Me and Mr.August sat across from one another. He had a big yellow envelope sitting in front of him. He looked at me and placed his hand on top of it sliding it over to me. "This is contract followed by rules, an agreement and a packet in which we will go over your hard and soft limits. This will help me understand what you're comfortable doing, what you're not comfortable doing and what you're willing to try. After that we will create a safe word which will let me know to stop during any of the activities. You typically use it if you're in a position where something I'm doing is hurting you in anyway. So are you ready to go over everything?" I nodded. He nodded his head. "Let's begin open it up to page 1. The rules."
I read over the rules listed on the paper.
1. I will serve to obey and please my dominant.
2. As a submissive I must trust that my dominant knows what's best for me.
3. I will not hesitate when responding to my dominant.
4. I will not touch my dominant without permission.
And the list went on. They didn't seem hard to follow. They were basically telling me as a submissive there was things I couldn't do and I had to at all times obey Mr.August. After reading my rules as a submissive underneath were Mr.August rules as a dominant.
It explained how as my dominant he had to take care of me and be there for me, help make me into a better submissive as well as never putting himself before my education, job or family.
"Any comments?" I shook my head taking a sip of my water. "Okay turn to page 5. The agreement. This is basically a submissive pledge and a dominant pledge. After it's read we both sign." He explained. "Read yours and I'll read mines." I nodded looking around. I cleared my voice and began to read the words from the paper in my hand. Loud but not too loud so only Mr.August was able to hear me.
"I will communicate with complete honesty my needs, desires, limits and experience. I realize that failing to do so will not only prevent my Dominant and I from having the best experience possible, but it can also lead to physical and emotional harm. I will keep an open mind about trying things that I am not comfortable with and on expanding my limits. I will continue to grow as a submissive and as a human being. I will accept the responsibility for discovering what pleases my Dominant and will do my best to fulfil Their wishes and desires. I will not allow myself to be harmed or abused. I know that being a submissive does not mean being a doormat. I will be responsive to my Dominant. I will not try to hide what my mind and both are feeling so that I may assist Them in their responsibilities as my Authority. I know Dominants are not telepaths and I will not expect my Dominant to know thoughts or feelings which I do not share. I will be obedient to my Dominant even if I disagree with what They are requesting. I realize They have my best interests at heart and often know better than I what I need in a particular situation. Above all, I will wear my title of submissive with honour. I will never cause others to think that being submissive means to be weak or sub-human. I will take pride in who I am and will never show myself in a negative way." I finished off signing my name on the dotted line like instructed to do so. I looked at Mr.August it was now his turn to read of the words from the paper he held. Although I had a copy of his I wanted to hear him say it.
"Above all else, a Dominant cherishes their submissive in the knowledge that the gift the submissive gives is the greatest gift of all. A Dominant is demanding and takes full advantage of the power they hold, but knows how to share the pleasure that comes from such power over another. In times of trouble, a Dominant will leave the roles behind and be a supportive friend and partner, never forgetting that this is still a loving relationship between two individuals. A Dominant is quick to understand the differences between fantasy and reality. A Dominant will never ask a submissive to put them before the submissive's career or family just to satisfy their own pleasure. To win a submissive's mind, body, spirit, soul and love, a Dominant knows they must first win the submissive's trust. A Dominant must always show their submissive that their guidance and tutoring in knowledgeable and deserving of the submissive's attention, that the Dominant is a person they can learn from in in whom they can trust their direction. A Dominant proves to their submissive that they are someone who can be leaned upon and depended upon. Never does a Dominant use discipline without good reason. When they punish their submissive it is always with a knowledgeable and careful hand. A Dominant is always open to communication and discussion; always ready to hear their submissive's wants and needs. A Dominant is patient, taking time to learn their submissive's limits and knowing that as the submissive's trust in them grows, so to will they grow. A Dominant understand the fragile nature of mind and body and never violates the trust given to them." After finishing he reached over the table and signed his name beside mine.
He sat up straight and clapped his hands together smirking. "Now that the boring part is out of the way time to have some fun. Take out the other packet that Says Limits on the cover." I did as told. "Now this is mostly going to be about what you like, what you don't like and what you're willing to try I will be taking notes as we go along. You may read out loud what actives and decide what's your soft limit meaning what you're willing to do and try and what your hard limits are meaning what you do not want to do."
I nodded flipping my hair from my shoulders onto my back.
"Okay, flogging is definitely a hard limit." I said making Mr.August laugh.
"Okay." He chuckled writing it down.
"Choking? Hard limit."
"Never really liked that anyway, continue."
"Bondage, eh soft limit. Being restrained doesn't seem so harsh." I said shrugging.
"Okay."
"Caning, Hard limit. Collaring Soft limit. Fisting, Hard limit. Hair pulling, Soft limit. Golden showers, Super Hard limit. That's just nasty." I said shaking my head. Spanking, Soft limit. Paddling, Soft limit. Knife play, Another super Hard Limit right next to Fire play. Anal beeds, Soft limit. Butt plug, Soft limit. Nipple clamps, Soft limit. Cock ring, Soft limit. Suspension, Soft limit." After going over about 50 more I've seem to be pretty open to more than half of what was on the paper.
"So now that we know your hard and soft limits lets go over a safe word. The most common one is Red. Usually if I was to ask how are you you would tell me Green you're good, Yellow It's tolerable or Red you want me to stop. Red is the main color you should remember because if it ever gets to that point you need to use it in order to let me know you want me to stop because if you just cry or scream without using the safe word I will not know you want me to stop understand?" I quickly nodded.
He nodded gathering the papers and putting it back into the envelope. "I'm going to bring these to my lawyer, from there a copy will be made for you along with a copy of the disclosure agreement you signed."
"Okay Mr.August."
"You can call me Chresanto, Jacob. You may refer to me as Mr.August and Sir while we are engaging in activities. Speaking of activities now that we've closed of this deal we can start visiting my playroom. There's actually rules for the play room but we'll discuss them later on." He said finally picking up the food menu. He motioned for a waiter to come. I looked at my menu and didn't know what half of the stuff here was. As the waiter approached us he took out a note pad and gave up both a smile.
"Good evening Mr.August and friend." He said knowing Mr-Chresanto! right off the back- Ima really have to get use to call him Chresanto now.
"Hello Charlie , I have the steamed vegetables with the mashed red potatoes, and seasoned chicken breast and uh a glass of whatever wine you recommend me and my partner." Chresanto said smiling at the boy who stood in front of us. His pale cheeks started to turn red which kinda made me upset. It's like every where we go someone has a crush on this man.
"I'll have the same thing he's having but instead of mash potatoes I'll like the 4 cheese macaroni." I said forcing a smile. Chresanto covered his mouth while holding in a chuckle.
Once the boy walked away Chresanto leaned against the table and licked his lips. "You really look great." He complemented. Suddenly I felt a cold firm had press against my thigh. I jumped a little at the touch. "Don't think a forgotten the stunt you pulled yesterday." I bit my lip as he rubbed his thumb on my inner thigh. My toes curled at the pleasure I was feeling.
"What are you going to do Mr.August?" I asked flirtatiously.
"Bend you over my knee and spank you 10 times." I bit my lip remembering it was a soft limit of mines.
. . .
Barely making in side Chresanto pulled me over to the couch and had my over his knees. He lifted my dress so my ass was in the open. He pulled off my underwear and thew it across the floor. "Remember the safe word Jacob?" I nodded. "What is it?"
"Red."
"Okay." He said rubbing his hand over my cheeks. "You must count. You mess up or you don't say it loud enough you get one added on. Understand?" I nodded. "If it gets overwhelming please Jacob please use the safe word I do not want to scare you off." I shook my head and looked back at him.
"I'm going to be fine." I said reinsuring him. He nodded.
"Okay."
In a quick sudden motion his soft touch turned into a hard smack. I gripped the couch cushion. "One!" I said loudly. It stung, it really stung.
After rubbing it for like a second he cocked his hand back once again, "Two!" I said a bit louder this time as his hand cane into contact with my bare ass which I felt was glowing red at his hard impact.
It was really fucking stung but it wasn't like I couldn't handle it. Chresanto was counting on me to be a good submissive and I didn't want to let him down.
The slaps came faster, back to back before I knew it I was crying out the number 10. My legs were shaking my ass was sensitive and my face was covered in tears. Chresanto pulled me up and sat me in his lap making me wince in pain. He wiped the tears from under my eyes. He softly peck my lips. "You did good. You'll get use to it I promise." I nodded.
He stood up still holding me in his arms. "Lets go put you in a warm bath."
"Are we going to do this again?" I whispered. My voice was nearly gone.
"What punishment?" I shook my head.
"Me dressing up like a girl." He shrugged.
"I don't know, you looked beautiful today but you looked most beautiful when you are yourself. Like the first time I seen you in your work uniform you looked beautiful, you even looked beautiful when you tripped over your own two feet and got my order all over you." He joked. I covered my face.
"You still remember that." He chuckled.
"Yeah I do." He said walking into the room and closed the door behind him.
. . .
This is probably the longest chapter i wrote. Kinda wonder if I still have readers considering last chapter didn't get much comments compared to the previous ones but if I did lose readers hopefully they start to come back as I continue to up date this book. I hope you guys enjoyed the chapter. If you have any ideas , thoughts or commentary regarding the story be sure to comment.
Now that the business portion is out of the way time to get to the fun stuff. *smirks*