Chapter 2

I woke in the morning to Jennifer sucking my cock. She had pulled the sheets off the bed and was kneeling between my legs, licking up and down the shaft. Every few passes she would let it slide into her mouth and wash the head with her tongue. Her other hand was busy teasing at my anus, sliding a little in to massage my prostate. I sighed in pleasure and Jennifer lifted her mouth off my dick.

"Good, you're finally awake. It's almost noon and we have lots to do today."

"What about the blowjob?" I asked gesturing towards my hard dick that she had left.

"Oh don't worry about that, there will be plenty of that later, we have to get going now. I have everything ready in the bathroom for you so get up and get in there," she said, pulling on my hands, struggling to get me out of bed. I reluctantly rolled out and stumbled sleepily after her.

"Here babe, sit down on the toilet. If you are gonna pretend to be a girl you might as well start peeing like one too," she teased, smiled as I flushed red with embarrassment.

"Look Jennifer, I know we had fun last night but I don't really think we should, you know, continue with this," I stammered. Sure last night had thrilled me and I'm pretty sure it was the biggest orgasm of my life but I wasn't at all sure I wanted to be a girl for her.

"Ahh, is Tiffany having second thoughts?" she taunted. "Well I took care of that for you already. If you didn't notice last night I recorded everything we did on video and uploaded it to my computer this morning while you were still sleeping. So, unless you want your friends to see you spreading your ass for me and loving every second of it, you better do as I say. Besides, I was there too and I know you had the biggest orgasm of your life. I did too after all!" she patted my face as I sat there in stunned silence, my mouth hanging open. I was shocked that she would use anything like blackmail to get what she wanted. Especially from me, her boyfriend!

"That's, that's ... blackmail!" I squeaked out at her.

"Hmm, I guess technically it is, but it's not like I'm forcing you to do anything you don't want to do baby," she said, as if that made it all right. I suppose in her mind it probably did. "Now quit your complaining and spread this cream over your legs. It's a hair removal cream and will make you slick and smooth like girls should be.

"Fine," I said, defeated.

"I think you meant to say, "Yes Mistress"," she scolded me. "Or would you like me to squeeze these?" Her hand was cradling my balls. I winced as I remembered the little squeeze she had given me last night.

"Yes Mistress," I said, looking dejectedly down at the floor. Jennifer's eyes were filled with laughter as she watched my humiliation.

She helped me spread the cream over my legs, getting all the places I missed. Then she made me bend over as she spread it around my asshole and butt. Lastly, she used a pair of scissors to trim my pubic hair down before spreading a little bit of the cream around my dick and balls. I sat on the toilet as instructed and waited for the tingling sensation she assured me would come.

"We are gonna have so much fun today," she said excitedly. "Let's hit up the department store at the mall first. Well, I'm kinda hungry so I guess lunch, then we get to shop for some clothes." She glanced at her watch. "Three minutes left."

"Jennifer, can we..." I started to say.

"Mistress"

"Hmm?"

"You said Jennifer, not Mistress. You will address me as Mistress when we are in private from now on or I will punish you," she spoke matter-of-factly.

I paused for a second, considering what she said. "Mistress, we can eat at the food court in the mall if you would like.

"Sure!" Jennifer said. "Oh, also, after the department store, I have a surprise for you!" she giggled excitedly, hopping up and down.

"Mistress, my body is all tingling now."

"Alright, wait another minute."

After a minute had past I jumped into the shower and sat under the spray, watching all the hair on my body wash down the drain. Then Jennifer handed me a bottle of shaving cream and a razor and told me to shave my armpits and face. When I was done I got out of the shower and dried off. I went back to her bedroom where I found her lying some clothes out on the bed.

"Since this is your first time, I think we will go a little easy on you. I got some stylish sneakers for you so you won't be wearing heels yet. Also, I bought you a nice pair of tight jeans. I know you secretly want to wear skirts but I think it's a little too cold out there right now for that. Here, put these panties on." She handed me a pair of pink panties.

I was shocked at how they felt as I pulled them up my smooth legs. They clung tightly to my butt and encased my dick in their soft, smooth fabric. I was embarrassed to find myself rock hard already.

"Hmm, we can't have that now, can we? Let me see if I can do something to help you," Jennifer said as she knelt in front of me. She pulled my panties down and licked the tip of my cock teasingly. Then, before I knew what was happening, she wrapped her hand around my balls, squeezing them slightly while holding a bag of freezing cold ice up to my crotch. I admit I let out a most unmanly screech as she did this but I guess it was in keeping with character now.

With her grip around my balls I couldn't do much more than whimper as she held the ice to my dick. When my dick was as soft and limp as it was gonna get, Jennifer pulled out a plastic device I had never seen before. It was shaped like a limp penis and structured like a cage.

"This is a chastity device, my sweet Tiffany. I got it for you because I know that little sluts can't be trusted to keep from touching themselves every moment they can," she said as she slipped it over my limp penis, adjusted the rings so it was tight behind my balls and locked the cage with a little lock. "There, now we won't have any unsightly bumps showing up in your jeans and you won't get all hard whenever you see cute guys walking by."

She stood up and kissed me on the mouth. "Mistress, I don't get hard when I see guys," I protested. "This is hurting me, do I really need to have this on?" I asked her.

She stroked my face lovingly. "Yes Tiffany, we need to keep your little dicklet safe in there. Plus we wouldn't want anyone accidentally mistaking you for a man," she laughed as she said the last part.

"Jennifer, I don't like you calling my dick a dicklet or clit, it really hurts my feelings," I told her. I was still that thinking this was all just a game and I didn't want her to know I secretly got a thrill every time she belittled me like that.

Slap.

I whimpered in pain, shocked that she had just slapped me. "MISTRESS," she yelled. "Next time it will be your balls and don't forget about the video." For a second I thought should was going to do it anyways but she suddenly seemed to relax. She smiled and I felt as if she had forgiven me and all was right in the world.

"Baby, if I didn't care about your feelings I wouldn't have put you in my panties with a cock cage on! Now, if you want to ever have any pleasure from that little thing you call a cock again you better be on your best behavior from now on, I have the only key after all!" She giggled, gesturing to a key that was dangling on a chain around her neck.

My pulse raced and my dick lurched, sending a wave of pain through me as it pushed against its confining cage, as I looked at the shining key nestled between the gentle swell of her breasts. I gazed down at the floor as she turned away and walked over to the bed. The last wall of resistance had fallen and I was now her slave. She picked up the jeans and threw them to me. I caught them and put them on, wiggling a bit to get them over my hips. They were very tight and really made my ass pop out. I looked down and sure enough, the chastity belt kept my cock from showing more than a slight bump.

Next Jennifer brought over a bra for me. It was a pink push-up bra with little black polka dots all over and a little black bow in the center. I put it on over my flat chest, struggling to do the clasp in the back. Jennifer giggled at my attempt before helping me out.

She brought over two objects next. They were flesh colored and sort of cone shaped. I realized they were breast forms when she pulled my bra out and slipped them inside.

"These should give you a nice little slut rack you can tease all the boys with."

After a few adjustments she stepped back and I looked down at my chest. The forms gave me nice B-cup sized breasts. I was oddly aroused at the sight of them even though I knew they were fake.

I knew Jennifer was still in control of my whole life from now on and I was starting to feel better about my predicament now. Though I still had my private reservations about dressing as a woman, I had to admit that the clothes did feel great on me. Jennifer handed me a shirt to put on.

"This shirt will go great with your jeans and really make your boobs stick out! What do you think?"

It was a black shirt with a sparkly rose decal on the front in a very Goth/Punk Hot Topic style. The back of the shirt had slits cut horizontally down it and I knew anyone walking behind me would be able to see the straps of the bra I was wearing and my smooth back all the way down to the pink panties peeking out above my jeans.

"It looks hot Mistress," I smiled shyly.