Jack's Gurl

The second thing. His cock. It was hard and large. Not very large like all the stories I hear about, but much larger than my own. I had no idea how big, but I felt it. It was not the diameter of a pop can but it could not have been too much smaller than that. And the length, I am guessing since I had no tape measure it was greater than seven inches, but probably not nine inches. Certainly somewhere in between. In the end, to me, it was very large.

I do not know how long we were kissing, but suddenly the door opened and I noticed it was my floor. Jack released me and I began to walk out of the elevator. Once outside I looked back and stared at Jack. The doors started to close, he reached out to offer me his hand but I did not take it and watched the doors close. My heart was pounding. What was I doing? Quickly, as fast as I could think and move, I reached for and press the elevator up button. I pressed many, many times over and over as fast as I could. But the doors did not appear to be going to open.

I started to turn to walk away when I heard the ding. I turned around only to crash right into Jack. He grabbed me, pulled me to him, stepped back into the elevator. He started kissing me again. This time all over my face, mouth, lips, neck, and ears. My arms began to reach back up as I did before. He stopped my one arm and directed my hand to his crotch.

"BABY GIRL, Daddy is going to make you feel so good. I am going to make you the prettiest girl in the building," he whispered into my ear as my hand landed on his bulge.

I wasn't sure at that time what that meant. I did not care. I just wanted to feel the strength of his arms holding me, his hands cupping my ass cheeks, his rock-hard cock in my hand and his warm mouth pressed against mine.

I was lost in his touches, his kisses, his voice whispering things into my ear between nibbles. I was lost in every moment. So lost that I had not even noticed the elevator stopped and the doors were open until I heard Linda's voice.

"I knew it," she said as she chuckled and winked at me. "I am sure you're about to have a wonderful experience, I hope you will truly enjoy it the way it is meant to be."

"Good night you two," she said as departed and she entered the elevator.

As the doors closed, Jack took me by the hand and lead me down the hall and to the door of his room. I cannot explain the feelings that were running through me but they were amazing.

As he used his key card to open the door to his room, I felt so nervous, so scared and all warm and tingling at the same time. I was just as confused as I was excited. Part of me on the inside was screaming to me, go, turn around, walk away. But another side of me was shocked at how wonderful it felt to have him groping me, touching me, controlling me. On the inside, I felt terrified about what was happening and or going to happen. But, on the outside, I felt safe and warm because I somehow knew that Jack was going to take care of me and protect me from anything bad happening to me.

The hotel room door closed behind us, Jack pressed me to the wall. He kissed me even harder than before. He slipped his hand into the waistline of my pants, wiggling his hand while pushing down on my belt, trying to force my pants to drop. He worked my belt and pants until they fell to my ankles. His hands then started working on removing my shirt. Once he worked my shirt off me he told me to finish getting naked. As I took my shoes off and began removing my pants and underwear from my ankles he turned to walk away.

"Get completely naked and sit on the bed until I get back," he said as he walked towards the bathroom.

I sat on the bed, naked. Embarrassed and nervous, I tried to cover myself up with only my arms and hands. Jack came from the bathroom carrying a small duffle bag and tossed it to me.

"Here put these on," he demanded.

I opened the bag to see it had several pieces of women's clothing. First, I pulled out a black silky lace teddy, and then some stockings, and then a garter, and a pair of panties and a bra. I looked at Jack confused.

"Come on sweetie, hurry up and get sexy for daddy," Jack demanded. "I want to see how pretty you really are."

I wasn't sure where to start but I thought the stockings would be the first to try. Not sure why. But at the same time how would I know where to start. I had never done this before so I have an idea if there was a right or wrong way. And it was just clothing so is there an incorrect way to get dressed.

It took me a few minutes to get everything on. Jack sat in a chair and watched me very carefully with every stitch of clothing I put on. And every time I put a piece of clothing on he would direct me to turn around and model the clothing for him. As he watched with excitement he ground his hand into his crotch rubbing his now hard cock. Once I was in everything he gave me, he ordered me to come closer to him. Once I was within his reach he reached over to attach the garter straps to the stockings. Afterward, he again instructed me to spin, slowly so he could see how pretty I was. As I twirled he spanked me on the ass several times.

He began commenting, "You are one sexy bitch baby girl, daddy is going to make you feel so good. Daddy is going to take you and you are going to love the new sexy whore you are about to become."

With that, he stood, pulled me to him, kissed me again, groped my tits and then my ass.

He whispered into my ear, "Are you ready baby, are you ready to be Daddy's little whore?"

I stared into his eyes and nodded my head yes. Almost as if I were in a trance, hypnotized. His hands came to rest on my shoulders and he gently started to apply pressure signaling to me he wanted me on my knees.

Once to the ground he unbuckled his pants and pulled his cock out. OH MY GOD. It was fucking huge. I knew he wanted me to suck it but I thought there was no way that it is going to fit into my mouth. He noticed my hesitation and chuckled.

"Don't worry baby girl, we are going to start slow and gentle but we are going to get it all in your mouth and all down your throat. You are going to make a fine cock sucker and before you know it you are going to always want daddy's big cock in your mouth. Now be a good girl and just start by kissing and licking the head of my dick baby."

I did as Daddy instructed me to. I pressed my lips against the large fat head of his cock kissing it ever so gently with the same excitement and enthusiasm as earlier when I was kissing Jack on the mouth.

"That's it, baby, that's a good girl, kiss Daddy's cock."

I kissed more and started licking his dick. Swirling my tongue up and around his shaft and head. He seemed to be enjoying it because he was moaning pretty good and kept commenting about what a great job I was doing.

"Okay baby, get ready, we're going to slide it into your mouth. Be careful with your teeth. Try to wrap your lips tightly over your teeth and remember to take deep breaths through your nose and you will be just fine."

I opened my mouth, he reached for the back of my head and gently applied pressure pushing himself deeper into my mouth. I suddenly realized I had to open my mouth much wider.

"Don't worry sissy girl you are doing a great job, just stay relaxed and let daddy works his dick into your throat," Jack said with a moan. "That's it, sweetie, deep breaths through your nose, you are doing just fine. Pretty soon you are going to have all of Daddy's cock down your throat."

I felt like I should be suffocating. I could feel his cock enter my throat but I kept taking the deep breaths through my nose and it seemed to be working. It was an odd uncomfortable feeling, this foreign object entering my throat. I even tried to swallow a couple of times because the sensation was like I was trying to swallow a bite from a meal.

Daddy seems to enjoy it when I did the swallowing attempts.

"Oh yes baby that's it, suck and swallow Daddy's cock, oh my god your throat feels good. You are going to be a great cock sucker when Daddy is done with you."

I felt like he was being more kind about my performance than the job I was actually doing because most of what I was doing was nothing. Nothing except trying not to choke or expose my teeth to his cock. It dawned on me that I did not want to disappoint Daddy. I did not want to be a bad girl. I wanted to be a good girl and I wanted Daddy to be pleased with me.

But still, it was Jack that was doing all the real work as he continued to slide his cock deeper into my mouth and suddenly he had his entire cock in my mouth. Every inch of his monster dick was in my mouth and down my throat. I could feel my throat swelled to accommodate his size. I felt a certain pride, a certain level of accomplishment. I had Daddy's whole dick in my mouth. I thought what a good girl Daddy must think I am. Daddy must be very proud of his baby girl, whore cock sucker.

But it was a little too early to celebrate.

Jack moaned in a deep tone, "Okay, darling now is when the fun starts. I am going to pull my cock out slowly and once it is nearly all out I will gently and slowly push it back into your throat. I'll do this a few times at a slow pace at first but after I that see you have it under control Daddy is going to pick up the pace a little more with each stroke. In a couple of minutes I am going to be pounding your mouth with my cock the same way I fuck my wife's pussy. I am going to make your mouth a pussy, a fuck toy. Are you ready, princess? Are you ready to have your mouth fucked?"

I stared upward, unable to say anything or even move because of the intruder in my mouth had me completely captured. Unable to do anything more than what Daddy wanted me to do, I merely tried to nod yes to confirm I was ready. With that, he started to pull his cock out, and then slowly push it back in. All the way in. And then pulled out again. Each stroke pulling further out until each stroke resulted in his cock completely leaving my mouth and then re-entering again and burying it all the way to his balls against my chin.

It was no easy task to accept his intrusion but I did not want Daddy to be disappointed with his baby girl. So, I just did my best to let him keep fucking my mouth. His strokes started to gain speed now and his hand started to guide my head more aggressively as well. It seemed like an eternity and his pace was much more aggressive now. His balls slapping me hard with each stroke. Both his hands now pulling on the back of my head while his dick fucked my face.

And then his legs started to tense up.

"Yes baby girl that's it, keep swallowing, keep sucking, you almost have it. That's it, baby, work that mouths on Daddy's cock, come get Daddy's cum, you almost have it, that's it, baby, be a good cock sucker and come get Daddy's cum."

I had no idea what to expect. I could tell he was getting even further now into my throat. Each stroke now was reaching further which really surprised me because I could've never imagined he could get deeper into my throat.

"Here it comes, baby girl, here it comes. That's it, princess, that's it, get ready-yyyyyyyyyyyyyyyyyyyyyy. OH FUCK YES BABY GIRL, FUCK YES, FUCK YES."

I could not feel or taste his cum because his dick was so far down my throat, but I could feel his cock swell up even more in my throat. And that was when I panicked. I freaked out and thought his cock was stuck in my throat. I tried with all my strength to pull my mouth off his cock. But his hands, his strength was too much for me to fight. He held my head tightly and with greater force, to the point that it was nearly painful the amount of force he was applying to my head.

I started to gag and could not catch my breath, but he pushed harder and deeper as he unloaded his cum into my throat. I could not breathe, I struggled to try to pull away. He finally released his grip. My mouth came off his cock so quickly. And that is when I could taste his cum. He was still having small eruptions of cum. Cum that he shot into my mouth as his dick popped out of my throat and mouth. Cum that landed on my face once he was all out of my mouth. His cock still hard, still spewing small blasts of cum.

"Be a good cock sucker baby, get all of daddy's cum," he said.

I started to take him back into my mouth. Just the head this time, and suck the rest of the cum from his cock. His body jerked a couple of times as I sucked on his big round cock head. His hands came to my shoulders again. Only to push me back, away from his cock. His dick flopped out of my mouth. One hand still on my shoulder, keeping me pinned to the ground, on my knees, his free hand grabbing the bottom of my chin and lift my face upward until our eyes met. I was still in a complete fog of what just happened. But a good fog. A weird uncertain feeling of doing a good job and being pleased I performed well for Daddy.

"You were a very good girl baby. Daddy is very pleased with his little sissy. You did a great job with your mouth and should know you are a very good cock sucker. I am going to enjoy turning you into the sexiest little whore, but not as much as you are going to enjoy being Daddy's whore," he said, staring down at me. Have you enjoyed being a good girl so far baby?"

"Yes Daddy it was really nice," I obediently replied.

"Get up sissy, we have some work to do before I put you down for bed," He said with a big smile on his face.

He instructed me to get naked, handed me a bottle of some type and told me to go into the shower and rub the cream all of my body with hair. Everywhere even my head. I was curious what it was for. So I asked.

"Baby if you still want to be Daddy's sissy you have to trust Daddy and just do as you are told. Daddy won't hurt you. Daddy is going to make you feel really good."

So, I step into the shower and started rubbing the cream all over my body, my head, arms, chest, legs, etc. Every inch of my body was covered. Head to toe. Jack stepped into the bathroom and began to run his hands all over my body, rub the cream in deeper with his firm hands. He gave special attention to my genitals and my ass cheeks. It was really turning me on. A lot. He stopped rubbing me. He pulled his hands away and reached for the showerhead and the faucet knobs. Once he had the water warm be begun spraying me down.

The next thing I see was a lot of hair in the tub. The hair from my body falling to the tub floor. It was only a matter of minutes and my entire body was smooth. I could not help but notice how soft my skin was as well.

He asked me to step out of the shower onto the towel on the floor. I did. He handed me a bottle of body lotion and instructed me to apply a generous amount of the lotion to my whole body. Once again I followed his command. After a couple of minutes of spreading the cream and working it in he reached for me again, pulling me by the hand and spinning me so my ass was towards him. He placed both his hands on my ass with what felt like more cream.

"Don't forget to add extra cream to your pretty ass baby."

He rubbed and kneaded my ass like he was working a bread loaf before baking. He was groping my ass very forcefully just before I felt it. That initial sting from his firm hand coming down sharply on my ass cheek. It stung for a second or two but was long forgotten when there was another sharp slap causing an increase in the stinging, now burning sensation. Suddenly I noticed my eyes were welling up and starting to tear up. And just as suddenly as the second came to a third and fourth and fifth slap. My ass was on fire. My eyes were no longer watering, I was crying, begging.

"Please Daddy, please I will be a good girl," I cried.

" I know you will darling, I know you are going to be a good girl, you are going to be Daddy's little sissy princess. But you have to know what happens to bad girls when they forget. Don't worry princess, Daddy loves you and will help you be the good girl you were meant to be."

He applied a little more cream to his hand and that's when I felt the cold lube being pressed against my virgin butthole, or should I say "my pussy" like daddy calls it.

"Now be a good girl and push your pussy back onto Daddy's finger princess," Jack passionately ordered , "Press back as gentle as you have to but don't stop until you have it all inside you."

I pushed back like I was told. First, the tip slipped in, it hurt. I stopped, waited for the pain to stop. Once it finally disappeared I began to push back again. Daddy grabbed me around the waist and firmly pulled me back to him at the same time he thrust his finger all the way deep inside me. I screamed out in pain. Oh, it hurt so bad. Daddy held me tight, leaning over until I felt his chest on me. He pulled tight and hard. The pain was overwhelming. It gradually began to go away. It was far from gone but just as it became bearable Daddy pulled his finger completely out and shoved it all in again and then again remained motionless. But not for long this time, he did it again, and after a second, again.

The next thing I had a complete sense of, was being slightly bent, Daddy's hand holding my waist, his chest to my back, his finger firmly wedged deep inside me. And then out of nowhere, even before the pain was completely gone, it hit me. A wave shot through me, a wave of pleasure. I whimpered and quiet little groan.

Daddy said, "there's my girl, welcome to womanhood princess, you are now ready."

And with that, he added another finger. I was moaning loudly now, he was pushing his fingers so deep into me and with such force, he was lifting me nearly off the ground. With each thrust, I was guided to my tiptoes. And with each thrust, I let out a soft moan, a feminine moan. And unmistakable moan of pleasure.

Daddy knew. He knew he had turned me. I don't know how I missed it but he was using 3 fingers now. It was nearly more than I could stand. It was so difficult to determine if it was pain or pleasure I was feeling with each final depth of his stroke. He was so far in me and had me opened up so much I felt so helpless. I did not want it to stop. I was no longer moaning at each stroke. I was moaning continuously in a more whimpered state. I noticed as I was whimpering and moaning and suddenly crying. Crying with a level of pleasure, not the same as earlier from the spanking. A spanking that I could still feel. But it was not the same feeling as earlier.

I am not sure how long he worked my "pussy" over but all of a sudden it was over, he pulled his fingers out. Weakened, I dropped to my knees leaned over the tub edge using my hands to try to gain my balance and composure. I felt empty. I could feel the cold draft. I could feel myself closing. I could not, at that moment feel or remember anything else, at all.

Jack's voice startled me, "You are a ready princess. You are ready to continue your path into womanhood. I am going to take you to a place where you are going to feel so much pleasure there will be no return. Once you feel what is coming next you will forget you were ever a man at all. You will only want my fat hard cock inside you.But before we can take the next step we have a couple more adjustments to make. Stand up baby girl, stand up and come to Daddy."

As I stood he embraced me, wrapping his arms around me and holding me tight. It is unexplainable how just hours ago I was a man. Masculine acting, woman loving, pussy eating man. And now here I am, being held by a bigger man. Feeling so weak, so soft, so fragile and so used for manly pleasures. I was now enjoying being held and didn't want him to let go. He lifted my chin once again, lowering his lips to mine, pressing his lips hard against my mouth, shoving his tongue deep into my mouth. His hand held my head firmly as he pressed himself to me.

There was a sudden clinking noise. I tried to turn to see the source but he held me firmly. I could feel his hand sliding up my thigh. I could feel something cold as well but I couldn't look. I did feel it when it slid over my own penis (or clit as it is now known). When I tried to speak Daddy shushed me.