New School, New Life

I sat down to start my makeup, but I was so excited, I couldn't even hold a brush steady. I looked around, and found that thankfully, Daddy hadn't finished the bottle last night. I poured an inch of whiskey into a glass, and slugged it back.

I sat back down and looked at the makeup booklet again.

"OK, foundation..." Well, I had better skin than anybody I knew of my age. "I think, at least today, I can skip that."

"Powder..., right that's this stuff. Not too bad..."

"A little light blush... OK, cheeks look alright."

"Now, they say I can use an eyeshadow to darken my eyebrows. Just a little darker than my hair... This brush... Not too much, though... Ugh! American Goth. Too much." I used one of the makeup remover pads to clean it off, and tried again with the lightest shade. "Much better."

"Now the really tricky bit -- eyeshadow. How on earth are you supposed to know when you have it right, if you can't see your eyelids with your eyes open? Oh, well, there's only one way to learn."

Eventually, after three attempts, I had one eye approximately the way I thought it should be. The other eye was a lot easier. I thought they matched close enough -- I guess that would be the most important part!

"No eyeliner or lipliner -- that seems like far too much work!"

The booklet said I should use a brown mascara with my light hair, but the kit only had black, so black it was. "Ugh. I hate sticking things in my eyes." I wasn't even sure if I was supposed to try to put mascara on my lower eyelashes, but I could barely find them myself, so I wasn't going to bother this time. Finally, I thought I'd got that alright.

"Last but not least -- lipstick." The kit only had two colors, a light pink and a deep red. Maybe one day I'd have the nerve for the red, but this time the pink would do.

Once again, the remover pads got a workout before I got it right. I definitely needed more of those!

I looked at myself with the light at different angles. I could see problems -- my cheekbones weren't quite level and one eyelid seemed to be larger than the other -- but I'd seen girls my age with years of experience who did a worse job. I patted myself on the back, literally, and picked up my phone to text Daddy.

As I waited for him, I realized I should have messaged him before I was quite finished. Now, I had far too much time to worry about what he'd think. I was almost ready to pour myself another drink when I heard the knock on the room door.

"Daddy?"

"Yes, hon -- I just didn't want to barge in on you." I heard him key the door, and waited anxiously for him to come in.

"Hands, what do I do with my hands?" Right -- I pulled nervously on the hem of my dress.

"Jamie..." He trailed off.

He was just staring at me. I started to shake. "You don't like it." I was almost in tears.

"No, honey, no -- you look incredible!"

"Really? You mean it."

"God, yes!" He took me in his arms, and kissed me. I swayed on my new heels, but with his arms around me, I knew I couldn't fall. I leaned into him and gave myself up to his kiss. Our tongues danced and his hands roamed across my dress, down my thighs, and back up under the skirt.

"ohhhh." I moaned into his mouth.

Eventually, he broke the clinch, and stepped back.

"Thank you, Daddy. I needed that. I was so nervous."

"Don't be. Nobody will ever know you're not a woman. You're perfect."

"Well, you'd better not have ruined my makeup!" I bent to look in the mirror, and Daddy stroked my ass. I grinned at him over my shoulder. "Men!"

"Women! - first thing they have to do whenever they see a mirror is check their makeup."

"I love the dress, Daddy, and the shoes. I hope I can walk in them."

"Just take small steps and hold onto me."

"Let's go shopping!" I exclaimed, but then I hesitated -- "oh! I guess the first thing I need is a purse. I have nowhere to keep my wallet, my phone, my lipstick..."

"OK, kiddo. Leave all those behind for now, and we'll get you a purse."

"...And more lingerie, a couple of dresses, something to sleep in -- maybe long flannel nighties, like Mom wears," I joked.

"I don't know how you're going to get flannel nighties if you can't take your own credit card with you."

"What? Don't you like them, Daddy?"

"I think you're going to be sleeping in something much more sexy, tonight."

"OK, you're the boss!"

"Yes, I am..."

* * *

Shopping was hell. I thought it would be fun, and it really should have been, but I was desperately horny, and Daddy was teasing me. I'd brush up against him at ever chance. I'd stroke his cock when we couldn't be seen, and eventually even when we could. Apparently, though, the fact that he'd come three times more in the past day than in the past two years had given him more staying power than I now had. He knew what I wanted, and he was dragging it out. We had to go to a dozen stores, we bought two more dresses, a pair of skirts, half a dozen tops, two pairs of shoes, stockings (holdups and the type that needed suspenders), suspenders, a corset, panties and bras, and a couple of baby doll nighties.

I finally had an idea.

"Daddy?"

"Yes, sweetie."

"You know you told me that I couldn't get myself off?"

"I had to to get my clitty back in my panties this morning."

"You disobeyed me?"

"Yes Daddy."

That was the end of shopping. He dragged me back to the car and we made it back to the hotel in record time.

In our room, he dropped all the bags on the floor, and ordered me: "Come here."

"Take off my belt."

I did, fumbling at the buckle.

"Give it to me." I did. "Now turn around and put your hands on the bed."

I obeyed, and he moved up behind me. "Straighten your legs." He started to stroke my ass.

"You disobeyed me."

"Yes, Daddy."

"You need to be taught a lesson."

"Yes, Daddy."

"I'm going to strap you, and I expect you to count the strokes."

"Yes, Daddy."

He peeled my dress upwards over my hips, and exposed my ass in its thong.

"One!" That wasn't so bad, it stung, but I could handle it.

"Two!" The other cheek.

"Three!" Back to the first side.

"Four!" Frig -- it was starting to burn.

"Five! Daddy, please!"

"What, baby?"

"Six! Please, stop, Daddy, I'll be good."

"You need to learn your lesson."

"Seven." I whimpered.

"Eight. Ohhhhhh."

"Nine! Oh, Daddy, fuuuuuck!"

"What?"

"Ten! Daddy, please fuck me NOW!"

I heard the belt drop to the floor, then the sound of his zipper and a cool liquid on my ass, his fingers massaging it into my rosebud as he moved the thong aside.

"Please, Daddy," I begged again.

"Now, baby." I felt his cock press against me, then suddenly he was in. I thought it would hurt, but my ass was already on fire, and his cock just felt so right. He began to push slowly into me.

"Oh, God, Daddy, it feels so good. Fuck me Daddy!"

"I'm so full Daddy. Oh, fuck. Ohhhhhhhh. Harder Daddy, fuck me!"

Daddy was panting, now, and pounding me as hard as he could. "God, baby, your mother was never this good a fuck!"

"Jesus, Daddy, yessss! Fuck me!"

"Come for me baby, come!"

And I did, feeling my balls release their load into my panties. Daddy came right behind me, and I felt his hot seed spewing into my ass. It felt like we both came forever, but all good things must end, and I collapsed on the bed, as Daddy pulled out of me.

"Turn around."

I did, in a daze.

"I expect you to clean my cock after you make me cum. Do it!"

I slipped to my knees in front of him, taking his dirty shaft in my hands, and sliding my lips around it. It tasted different, but surprisingly, I didn't mind it. I slurped it hungrily making sure I got every drop of his come.

"Thank you, Daddy," I breathed.

"You're welcome, baby. Straighten, your dress, it's time for dinner."