Kylie's New Life: The Day After

I was disappointed the next morning, when I woke up Jacob was not there I got up and looked around for him. He was not in the bathroom as the door stood open and it was dark. It took me a moment to realize I was naked. I quickly went to the closet and grabbed a robe, I found my dress from the night before hanging fully cleaned. I finally looked at the clock. It was just past 11am, I was shocked I had slept so late. I kept looking around, and I finally found a note on the table next to the phone.

Kylie. I had to go into work, I did not know I would have to do so, but they had some silly emergency. Please order what you would like for breakfast and have it charged to the room. If you would like to leave please call the desk and ask them to send package A up to the room. They will deliver some fairly mundane mens clothing to you and you can leave without any fuss and you may keep the clothing. If you want to stay however and really give being a girl a go have the hotel deliver package B. I believe you will find this to be more interesting. You are under no obligation to stay if you get package B and change your mind. I would rather you be willing to be with me than not. I am not sure what time I will be back so if you stay please feel free to eat lunch here as well and dinner if I am too late. I do hope I get to see you when I get back baby girl.

Jacob

XOXO

I admit I was not totally sure what to do, should I stay? Or should I go? I did not think there would be any trouble if I left, but could I go back to my normal life? Did I want to? I threw myself back down on the bed and put my hands over my eyes. What to do, what to do?! My stomach growled and I laughed. I decided to get some food and saw that they were still serving brunch. I ordered some chicken and waffles and a bowl of fruit. When it came I sat at the table and ate. It was quite tasty. As I ate I thought, I had deffinatly enjoyed the sex feeling like a woman in the arms of a man had been amazing and his cock, oh his cock so huge. He did say I could change my mind what would it hurt to ask for package B? I made my decision. I called the front desk and asked them to send you package B.

A bellhop handed me an envelope and a laptop. When he came to the door he tipped his hat and left before I could even offer a tip. Which I thought was weird as the server had waved away a tip as well. I opened the envelope first inside was a black metal credit card. I had heard of these but never seen one in person. I gulped realizing exactly how rich Jacob must be. There was another note, this one much shorter, telling me to order what I wanted, anything I wanted and it would be delivered on the same day.

So I started shopping, keeping myself to Amazon alone for now. I had never had a chance to buy whatever I wanted so I went a bit crazy. By the time I was done I had bought nearly two thousand dollars worth of clothing. I checked out and clicked the same day delivery. The package would be ready in two hours it seemed. So I had time to kill. I took a shower and shaved all my hair off again making sure I was smooth. I sat and watched some TV and tried to relax. I thought about Jacob. He seemed to be very rich, but this was a somewhat standard hotel room. Bigger than usual but nothing special. Maybe it was because it was a sudden trip, or maybe he did not like a bigger room? Maybe he was lying? I did not know and had know way to know he did seem nice though.

The knock at the door two hours later was a surprise and I was handed all of my stuff. And I mean all of it. Which needless to say surprised me yet again. I had just started going through it all when the phone rang. I picked it up and in my best girly voice said hello.

"Hello baby girl are you having a good day so far?" I gulped as I heard Jacobs baritone voice on the phone.

"Uh... I mean yes! Yes! Daddy, I am having a good day. Thank you for leaving your card for me!" Was that really me saying that I wondered.

"I'm glad you are happy baby girl, sorry I got called away, emergency at work. A CEOs life is always exciting." I had not known he was a CEO, did that make me feel differently about him? "Listen baby girl, I'm going to be back in about five hours. I know it's a long time, but if you want to stay, I would not mind if you were wearing something nice when I get there."

"Do you want me to wear lingerie, or a nice dress Daddy." He chuckled, and I smiled, feeling my knees go weak, and my cheeks getting hot. I could not believe I had just asked that.

"Why don't you just find a nice dress for me Baby Girl. I am not sure if I'll be in the mood as soon as I get back." I sighed in disappointment. And he chuckled again. "Oh don't worry Baby Girl, you are going to be taking my cock again soon. Just be ready for me when you get back. I'll have a nice dinner delivered for the two of us."

"That sounds lovely Jacob, I'll make sure to find a nice dress for you."

"See, that you do baby girl I have to go now have a good day, see you tonight." We hung up and I looked at the clock, five hours to figure out what to wear.

Five hours later I had fixed my wig and done my makeup. I was wearing a tight black, thigh length club dress. I had a black thong under the dress the top was high necked and covered most of my chest but the dress was sleeveless so I had a lacy black bra under it. A pair of strappy black heels with gold buckles completed the look.

Right on time the door opener and Jacob walked in he smiled as he saw me. Giving a low wolf whistle as he looked me up and down. He walked across the room and took me in his arms, kissing me deeply passionately. I felt myself pressing against him kissing back. He pulled back after what felt like hours but was only a couple of minutes.

"You look, very pretty baby girl, bit different from last night, that's for sure." He smiled and I felt myself blushing. "Let me go ahead and order dinner for us and we can sit and talk, maybe enjoy a bottle of wine. I am sure you have questions for me." He flashed his perfect smile at me and I blushed again.

Two perfectly cooked steaks with mushrooms and a nice salad were sent up to the room and he had the waiter place them on a table so we could both sit and enjoy the turned the lights down low and I even pulled the chair out for me letting me sit down first. Jacob poured us each a glass of wine, we clicked the glasses together and I sipped the wine slowly. We ate in silence for a bit until he finally broke it.

"So what do you want to know about me?" I thought about it for a minute or two.

"So what do you do for a living?" He smiled

"I am the CEO of a tech company but that is not all we do, I have been gaining a lot of popularity recently as I insist on paying my employees a proper living wage with actual pension plan as well as a 401k and full insurance coverage sick days and generous vacation packages with a full year of paid maternity leave for both parents." I was shocked. I had actually heard of this company and they were making waves. I had even seen him on a magazine cover more than once now that I thought about it.

"This is a rather modest hotel room for a man such as yourself" he smiled again.

"I am not a picky man and I don't need anything fancy to be satisfied plus they had already given away the penthouse to another guest before I booked. I was not going to make them move."

"How did you end up at the ball last night?" He chuckled.

"I have always been pansexual and I saw it in the adverised by the hotel and managed to get a last minute ticket." He smiled looking, me over again as he did. "And I am glad I did" I blushed again.

"What do you want with me?" He smiled.

"What any other man wants, a girl, a woman at home for him, someone to love and support me when I need it and I can love and support in return. I want that in general mind you, that could be you if you want it to be." He smiled but got more serious. "You can try it for a while, see if you like it, and leave. I will be disappointed but I will be understanding. I will never force you to do anything you don't want to do. All you need to say is No." He sighed. "To be with me though I would expect you to present as female at all times you don't have to get any surgeries or hormones or anything like that if you don't want to. But all your pronouns would be female and I would help you legally change your name if you want."

"So it could have been anyone that you took back to your room last night?" He shook his head no.

"No you were the only one wearing a gown like that, like you wanted to stand out and show off your feminine side. No one else there struck me like you did. You stood out, you are special." I blushed. I did not know what to say.

"How ummm old are you?" He again chuckled.

"I'm 42, 43 in about two months and you?"

"I am 32." I was happy I preferred older men though he did not look ten years older than me.

"You don't have to decide what you want right this second." He stood up and walked around to the other side of the table. We had finished eating. He stopped next to me and I stood up. "Let's enjoy tonight and see where things take us." He took me in his arms and kissed me passionately! The hot feminine feeling washed over me and my knees went weak and my head swirled. His hands slowly started to roam my body his hand found my ass squeezing it slowly kneading it gently. I moaned softly.

His hand found the zipper of my dress and slowly unzipped me letting the dress fall to the floor while kissing my neck, he kissed up to my ear and whispered how beautiful I was. He picked me up and carried me over to the bed, he was so strong! He lay me down and undid my bra he pressed his lips to one of my nipples sucking on it gently teasing it with his tongue and teeth. I moaned his big hand found my clit barely contained under my lacy thong. He rubbed me stroking my shaft gently through my panties. I felt him slip the thong to the side gripping it in his hand and rubbing just the tip with his thumb kissing my lips again as he did, slipping his tongue into my mouth.

"Am I your first man?" He asked as he slowly broke the kiss, I nodded. He grinned that perfect smile again. He started taking off his clothing letting me help finally his hot hard twelve inch long three inch wide cock. He pressed it against my much much smaller, more average seven incher and smiled down at me. "So baby girl are you a man or a woman?" I was confused by the question, not because I knew the answer but because the answer was not what I expected.

"Daddy I am a girl! I reached up putting my arms around the back of his neck. "I want to feel like this all the time Daddy! Please Daddy if you will have me I want to be your girl full time!" He grinned again.

"Turn over for me Baby Girl!" I did, turning over under him he slipped my panties off me, running his hand down my smooth legs as he did. He kissed slowly down my back to my ass he spread my cheeks gently and pressed his lips slowly to my ass pussy. I felt his tongue reach out and lick my tight hole. Slowly he started to eat me out making me moan in pleasure. I noticed a mirror on the wall nearby. I could see him eating me out and it just made me hotter.

"Oh Daddy please put your cock in me!" He pulled away from me and grinned looking in the mirror as he did. I smiled at him over my shoulder. He spread my legs a bit further and got me up on my knees as he did. He pulled some lube out of a drawer, and I felt him start to press a finger into my pussy. I moaned, closing my eyes enjoying his touch. He lubed me up first with one finger then two and slowly pulled out. He got on his knees behind me letting his cock slap against my ass. I could see it so huge in the mirror my body practically quivered with anticipation.

"That's right Baby Girl, Daddy is gonna put this monster cock deep in that tight pussy of yours." He lubed himself up taking his time before pressing the head against my hole. I could feel it just sitting there. I started to wonder why but I heard him speak. "You are gonna make a wonderful girlfriend, Baby Girl, and maybe someday an even better wife!" Could I be, could I be a wife someday? I could not think long though as I felt his cock start to stretch my pussy pressing into it. With a pop the head was inside me stretching me. It did not feel painful though, just big. He started to slide his cock deeper into me and surprisingly he did not take long to press all twelve inches into me. His balls were slapping against me.

"You see that Baby Girl!" I turned my face to the mirror again. I saw myself on my stomach back arched down my butt upwards, his hands on my hip, his cock pressed deep in me. Our skin color contrasting his dark mine pale. He started to thrust my eyes crossed. I gasped and moaned. Part of me wanted to reach for my clit but I found I could not.

Jacob reached over my back and took my neck around my throat pulling me up onto my hands gently not choking me but getting me onto my hands and knees thrusting harder making me watch as he did. I was gasping and moaning when he suddenly pulled all the way out of me. I looked at him pleadingly wanting his cock back inside of me. He got me to sit up as he sat on the edge of the bed facing the mirror. I moved to him kissing him as I did. He kissed back and motioned me to face the mirror as well and put my legs around his. I did as he asked my back against his chest. I looked in the mirror.

There I was though my hairless but still unmistakably masculine body my clit hard as a rock pointing upwards my legs spread and Jacobs hard black cock under my ass. He positioned his cock slowly against my hole again. And I watched as I pressed that still masculine body down against a real man's cock. My face as I did so was a face I had only seen on women before. I never felt more alive. I started to ride his cock so deep inside me pressing against my G-spot.

"Oh God Daddy I'm not gonna last long I'm gonna cum from your cock!" He pressed my body up and started to thrust hard into me rather than letting me ride him. I watched all of this, my clit bouncing, my voice sounding so girly as I moaned in pure pleasure above him. I started to cum hard, my whole body feeling pleasure flow through me in waves. With a final thrust pressing his own cock deep into me I felt him start to orgasm deep inside of my pussy flooding me with his cum. His moans of pleasure mixing with mine.

Slowly he slipped his cock out of me and lay me down on the bed slipping his arms around me holding me against him he kissed me. I kissed back feeling fulfilled and for the first time in my life I felt complete.