tagTransgender & CrossdressersKitten's Adventure Ch. 01

Kitten's Adventure Ch. 01


Edited by: DrBisensual

Authors Note: This story is written from perspectives that alternate between Kitten, a young crossdresser from Denmark, and her Daddy, an older dominant man from America. Both characters are based on real people, but the story is fiction, at least for now...


Chapter 1 - Kitten Meets Her Daddy

I couldn't believe this was about to happen. I was finally going to meet my Daddy in person. After months of chatting online, detailed planning to pick a date that fit both our busy schedules, and saving up my Euros for a plane ticket, the day had finally come. To say that I was nervous was an understatement. I turned around twice on the way to the airport, but my curiosity, desire, and the fact that I had already purchased an expensive airline ticket saw to it that I boarded a plane and made the long flight from Copenhagen to Chicago where we were to meet and spend a long weekend together.

While Daddy had kept most of his plans for me a secret, he made two things certain: 1) when I was with him, I would be dressed fully and act as a girl, and 2) I would be expected to do everything he asked. We had discussed my limits and I trusted him to not ask me to do anything that I didn't want to do, but I secretly couldn't wait to be under his control and to finally lose my sissy virginity. I had been dreaming this for months.

As I got off the plane, I could feel my heart pounding in my chest. I had to stop in the first restroom I could find to calm my nerves and attempt to make myself presentable. I was very nervous about meeting him in my normal androgynous mode. I checked myself in the mirror – it definitely looked like I had just been on an over nine-hour flight. My shoulder length blond hair was in a tight ponytail and didn't look feminine at all and my usually bright blue eyes were bloodshot. I took the band holding my ponytail out and brushed out my hair into a more feminine look - much better. A few drops of Visine cleared my eyes. After straightening the collar my gray cardigan and smoothing the wrinkles in the pale pink t-shirt I was wearing underneath, I did a quick half-turn, slightly lifting my sweater to see how my behind looked in my dark blue skinny jeans. At least my backside still looked good, and if I looked close I could even make out the line from the lacy low-rise pink panties I was wearing. I got a couple of strange looks from the men in the restroom, but I didn't care. Dressed like this, no one would mistake me for a girl, but at only 173 cm (5'8") and only 59 kg (130 lbs.), I certainly didn't exude much masculinity. I reached into my carry-on and got out my strawberry lip gloss and perfume. I applied a thick coat of gloss to my lips and dabbed some perfume on my neck and behind my ears. An older man at the sink to my left scowled at me, clearly disgusted at my feminine actions. As he finished washing his hands I heard him mutter "faggot" under his breath as he exited the rest room. A guy about my age at the sink to my right saw my discomfort and gave me a reassuring smile and wink, saying, "Don't worry about him Hun. I think you look great." I thanked him and popped a piece of mint-flavored gum in my mouth (I really wanted a cigarette). With my nearly empty ca.rry-on in tow I exited the rest room feeling refreshed, but still very nervous about what the next few days would bring..

My hands shaking, I sent a message to Daddy to let him know that I had arrived safely and was making my way towards the baggage claim area where we had agreed to meet. He messaged back right away that he was waiting for me. The butterflies in my tummy started fluttering again. This was really happening! Each step seemed to take an eternity. As I descended the escalator to baggage claim, our eyes met at the same time. I immediately recognized the handsome salt-and-pepper bearded face, He was wearing a gray collared shirt and navy blue blazer, blue jeans, and brown leather oxfords. As he peered at me with his steel blue eyes over the top of his glasses, I noticed his eyes slightly widen and a faint smile appear on his face, assuring me that he was happy to see me. As I closed the distance toward his beefy 6'4" frame I could feel my pulse quicken and my legs start to go wobbly. I can't fully explain the way he made me feel, other than to say that when we chatted online, he made me feel completely feminine. Besides the obvious age difference (he was in his mid-forties compared to my young 22 years) he was everything I wasn't: rugged, masculine, and ready to take control of any situation. I had been attracted to these qualities since the first time we chatted. As I took the last few steps to him, he recognized my condition and took my hand, steadying me and reminding me how small I was compared to him.

His hands were large and rough to the touch, reminding me that he was a man who enjoyed being outside and working with his hands .Even though there were hundreds of people coming and going in the busy airport, it felt like we were the only two people on earth. If anyone was staring at us, I didn't notice. All of his attention was focused on me, making me feel safe and willing to do anything he asked, he looked me over from head to toe and slowly spun me around, finally settling his gaze directly into my eyes. His delicious cologne, musky and masculine, caused my thoughts and my eyes to drift toward his crotch, until I felt his strong hand lift my chin up, causing our eyes to meet again.

He leaned close and whispered in my ear, "There will plenty of time for that later kitten." His warm breath sent shivers down my spine.

"I-I'm sorry Daddy, I couldn't help myself" I sputtered, barely able to get the words out of my mouth. The anxiety I was feeling was only matched by my excitement for what the next few hours would bring.

"Let's go." he said as he relieved me of my carry -on and led me by the hand toward the exit.

We walked outside and toward the short-term parking garage, exchanging some small talk about the flight, the weather, and the enormity of the Chicago-O'Hare airport along the way. As we stepped outside into the cool autumn air, I moved closer to him, pretending I was cold. He wrapped a hand around my waist, pulling me close to him and allowing me to enjoy the ample heat radiating from his large chest. As each moment passed, my anxiety slowly faded.

By the time we reached his car, a shiny and black American make, I was only feeling excitement and anticipation of what was to come. He opened the trunk and stowed my carry on, then turned to face me. Before I knew it, his strong hands were in the small of my back, pulling me close. I wrapped my arms around his broad shoulders, let out a breathless sigh, and moved my lips eagerly toward his. As his lips pressed firmly to mine I was happy that I remembered to put on my lip gloss, and that I had remembered to remove my lip piercing. His forceful lips parted mine and his warm tongue explored my mouth and teased my tongue, causing my knees to weaken again. I had never been kissed by man before, and no girl had ever kissed me with this intensity. My "clit" immediately stirred in my panties. I tried to separate my hips from Daddy so he wouldn't notice, but he just lowered a hand to my bottom and pulled me closer, forcing me to grind my growing bulge against his strong upper thigh. I could feel the heat from his manhood radiating against my belly. I suddenly felt completely helpless and was loving every second. Our lips finally parted but he still held my body tight to his, our foreheads touching. I tried desperately to catch my breath as Daddy spoke.

"Do you trust me kitten?"

"Yes Daddy, I trust you", I said, still trying to catch my breath.

"Are you ready to do anything I tell you to for the next 48 hours, without question or hesitation?"

"Yes Daddy, I want to be a good girl for you and make you happy." I panted.

"Then I think we are going to have a wonderful weekend." he said as he loosened his grip and opened the passenger side door for me.

I made my way to the door and stepped the car. Daddy got in and retrieved and envelope from his jacket, which he handed to me before starting the car. I opened it as we made our way from the parking garage. It was full of Euros. I frowned and looked at daddy curiously.

"Reimbursement for your plane ticket." he said matter-of-factly. I still must have had a puzzled look on my face so he continued.

"I could have bought your ticket for you in advance, but I wanted you to be committed to making the trip. I thought that if you had spent your own hard-earned money on it, you would be less likely to back out."

"I understand. Thank you Daddy" I said, leaning over to place a soft kiss on his cheek.

"Thank you for trusting me and for making the long trip. I'm really proud of you baby girl", Daddy said as he gently caressed my knee. It made me feel so good to hear him say he was proud of me.

"I've always wanted to visit America. You just gave me a reason." I said with a mischievous grin.

Daddy returned my smile and maneuvered the car expertly through busy traffic as we exited the airport. I looked out the window in awe of all the planes landing and taking off. I had heard that O'Hare was one of the busiest airports in the world and it certainly appeared that way.

"I got us a hotel room near the airport for this evening and it will only take a few minutes to get there. I want you to become a beautiful girl as soon as possible. We'll head into the city tomorrow." Daddy said.

I suddenly felt ashamed about how I must look to him. I had completely forgot that I was still dressed as and looked mostly like a boy, albeit an androgynous one. I wanted to get out of these clothes as soon as possible.

"That sounds fine." I said, staring down at my boring sweater and jeans. As if reading my thoughts, Daddy spoke.

"I think you'll enjoy what I picked out for you to wear tonight."

"Thank you Daddy, I'm sure that I will." I replied, feeling relieved that I would soon be able to shed all traces of masculinity from my appearance.

We quickly arrived at the hotel. It was just after 3pm, so the parking lot was mostly empty. Daddy grabbed my suitcase from the trunk and escorted me, resting his hand and my hip. . It was a large suite-style hotel with rooms designed for well-to-do business travelers. Daddy must have already checked into the room, because he directed me to the glass elevator opposite the lobby, facing a large central atrium. Once in the elevator, he pressed the button for the seventh floor. Just before the doors closed, a young couple got on the elevator with us and pressed the button for the tenth floor.

As the elevator rose I felt Daddy's hand begin to caress my bottom and gently reach between my legs to my most sensitive area, causing me to purr, spread my legs slightly, and lean back into him. I knew the other couple was watching us, but I didn't care. I only wished that I was wearing a dress or skirt to give him easier access. I was so horny that I would have let him fuck me right there in front of the other couple and in plain sight of anyone in the hotel atrium. When we finally arrived at our floor, Daddy took my hand and guided me toward the door. I exchanged a quick glance with the woman as we exited the elevator and she gave me a knowing smile and wink. As the elevator doors closed behind us I heard her say "Have fun you two."

We made our way to our room. Daddy opened the door and held it for me, telling me to have a look around and get comfortable as I entered. The suite was made up of two large rooms. The front room faced the atrium and had a sofa, television, a small bar and kitchenette, and a small attached rest room with a sink and toilet. The room in the back contained a large bed, closet, and another attached bathroom with a bathtub and shower, and glass doors leading to a balcony. A vase full of red roses was on the dresser. I stepped on to the balcony and noticed. Daddy followed me onto the balcony.

"Nice view isn't it?" he said, as we looked out at the Chicago skyline.

"Yes it's beautiful." I replied as I turned to look at him.

"Let's go back inside, we'll have plenty of time to see the city tomorrow." He said as he led me back inside.

Daddy went to the front room and closed the curtains on the windows that looked out into the atrium. Then turned to me with a very serious look on his face.

"Remove your clothes and give them to me.", he instructed.

I was a little shocked at his abruptness, but quickly regained my senses and removed my sweater, t-shirt, shoes, and socks, then shimmied out of my tight jeans. I picked them up, handed them to Daddy and faced him wearing only my pink and white floral-patterned panties. My hands covered the bulge in the front of my panties made by my small cock and balls. I stared at the floor, feeling ashamed, embarrassed, and extremely turned on all at the same time.

"The panties too." Daddy said.

I gave a quick pleading glance at Daddy, but his stern look told me that I didn't have a choice. I removed my panties and handed them to him, quickly moving my hands back to cover myself. He placed the clothes in my suitcase and approached me.

"Hands at your sides and keep them there." he ordered.

"Yes Daddy." I replied. I have never been more embarrassed. The humiliation I was feeling made my clitty shrink, and it felt as if my tiny balls had retreated into my body. Daddy moved close to me and placed his large hand over my hairless genitals, completely covering them. The warmth from his hand felt wonderful, and strangely, I began to feel more comfortable being completely exposed to this strong and confident man. His other hand moved up my back until it reached my hair, which he firmly grasped and used to direct my face to his. Looking me straight in the eyes, he spoke to me in a firm but calm tone.

"Never be ashamed of your body around me. Everything about you is feminine and beautiful. Your sparkling blue eyes, your soft, smooth skin, your luscious, kissable lips, your cute round ass, and even this. " he said as he gave the tiny shaft of my penis a firm squeeze.

"Yes Daddy. Thank you Daddy." I whispered in reply. I was lost in a whirlwind of emotions and was finding it hard to concentrate.

Releasing his grip of my hair and genitals, Daddy spoke again, "Now go into the bathroom and follow the instructions I've left for you. When you've completed everything on the list, come back out to see me. I'm going to pour myself a drink and catch up on some reading. Would you like a glass of wine?"

"No thank you Daddy, maybe a little later." I said. I was already a little drunk from the rush of emotions and was afraid that alcohol might make it worse. As if in a trance, I turned and went into the bathroom.

I found a note listing what I was supposed to do taped to the mirror. There was also a large pink gift bag on the floor but I couldn't see what was in it. I was a relieved to find that the list wasn't that long. It read:

1.Take a shower. Use ALL of the products I have placed in the shower for you.

2. After showering, open the bag and use and/or put on all of the items.

3.When finished, put on the robe hanging on the back of the door and come back to see me.

I opened the shower curtain and found multiple items waiting for me. Female body wash, shampoo, hair conditioner, and one of those fancy women's razors with the ring of soap around the top. I turned on the water and got into the shower. I lathered up with the fragrant body wash, then used razor to remove any stubble from my face, legs, underarms, and bikini area. I am blessed to have very little body or facial hair and what little I have grows very slowly, so it didn't take very long. After I shampooed, conditioned, and rinsed my hair, I stepped out of the shower and wrapped a towel around my chest and another around my head.

I went to the sink and found a large bottle of body lotion, two brand new toothbrushes (a pink one that was obviously for me and blue one for Daddy), toothpaste, a few different types of hairbands, a woman's hairbrush, and a small bottle of Lacoste "Touch of Pink" perfume. As I brushed my teeth I applied the lotion to my legs and arms, leaving them feeling silky smooth. I then brushed my hair straight and dried it using the hair dryer. I then picked up the gift bag and started removing the items in it.

The first item was a makeup kit that included foundation, mascara, a few different shades of eyeliner, blush, tweezers and a makeup brush. There were also a couple different shades of lipstick, a light pink and a bright red, along with a lip liner pen. Daddy had asked about the brands of makeup that I liked and must have been taking notes, because they were all the brands that I mentioned. I started by touching up my eyebrows with the tweezers. I then applied a little foundation and blush to highlight my cheeks, and did my eyes with the eyeliner, a light pink eyeshadow and mascara, making sure to include my signature "cat eye" that Daddy loved. I had spent countless hours watching YouTube videos and practicing applying makeup, and felt I was better at it than most girls. I finished off with the lip liner and pink lipstick, and sprayed a little perfume on my neck, wrists and just above my clitty. I must admit I looked and smelled pretty good and hoped Daddy would be pleased.

The next item in the bag was a large black box, which I opened to find a pair of very realistic-looking silicone breasts forms. I was super excited because I had always wanted these, but could never afford them. They appeared to be about a C-cup size, which would look rather large on my small frame. They also had very realistic looking light pink nipples. Inside the box were detailed instructions for attaching them, a tube of body adhesive, and a small tube of concealer to make the edge of the forms blend in to my skin. I followed the instructions to attach them and used the concealer help blend them into the skin on my chest. They looked amazing and I loved the fell off of them on my chest. With the makeup and breast forms, I couldn't believe how much I looked and felt like a beautiful and very sexy woman. After a few minutes of admiring myself in the mirror, I realized that I needed to finish getting ready for Daddy.

I reached back into the bag and found a 6-pack of saline enemas. This made me a little nervous. I had been reading and watching instructional videos about enemas and Daddy had told me that I would be expected to give them to myself, but I hadn't tried it yet. I know Daddy would be disappointed if I didn't use them, so I decided I should try. Fortunately, detailed instructions were included and it wasn't as bad as I thought. I'll save you all the details, but will say that by the time I was on the second enema, I was getting pretty turned on. I imagined that it might feel a little like it will feel when Daddy finally takes my virginity.

The next item in the bag was a small box. I opened it to find a small metal butt plug with a pink jewel on the end, along with a bottle of water-based lube. The plug wasn't very long, but the wide end that goes inside me did look a little intimidating. I used a generous amount of lube both on my bottom and the plug. After taking a little time to loosen myself up with my fingers, I slowly began to work the plug inside me. It was a little painful and I must have been making some noises as I tried to work it in, because Daddy knocked on the door and asked if everything was OK. I replied that I was fine and was almost ready. I was finally able to push the widest part into me, and quickly the pain began to subside. I leaned on the sink taking deep breaths and tried to get used to the feeling of the plug inside me. I was also trying to control my own erection, because by now I was getting really turned on. I ran some cold water over a wash cloth and placed it over my genitals. This seemed to work, causing my erection to deflate and my balls to shrink back inside of me.

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byMasterThomas79© 4 comments/ 7957 views/ 7 favorites

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