Date: Mon, 12 Nov 2007 19:45:58 -0800 (PST)
From: Kara Brown <kara_cd412@yahoo.com>
Subject: College Crossdressing Slut 22:  Roleplaying with Daddy

			College Crossdressing Slut
		    Chapter 22: Role-playing with Daddy

	I got home a lot earlier than I had planned that night but I
definitely didn't feel like doing anything.  When I arrived at my
apartment, the first thing I did was go check out the mirror.  I felt like
such a naughty girl since I had taken off my panties and entered my
apartment holding them in my hand.  As I looked in the mirror, my mascara
stained face was a mess but that's not what I wanted to see.  I immediately
checked out my ass.  It was bright red!  The ice had numbed it
significantly but my ass was fire truck red all the way around.
	I went to my bed and lied down on my tummy.  I felt a little sick
to my stomach.  I had such a crush on Robert but he was really mad now and
I didn't know how long he would be mad for.  I really wanted to be with
Robert but I also wanted to have my wild times with other guys.  Plus, I
didn't even know how Robert felt about me.  Sometimes he seemed to like me
a lot and sometimes he seemed like he just wanted to use me for a warm hole
to stick his cock.  I fell asleep with a stinging ass and a nauseous
stomach.
	When I woke up in the morning, I called Robert right away.  It was
pretty early but I really wanted to talk to him.  I got his voicemail so I
tried to explain everything but my message was too long so I had to call
back and leave a second message.  I really didn't feel like going to school
so I skipped class and waited for Robert to call back.  Unfortunately, he
never called that day.  I spent the rest of the day upset and lounging
around in a tank top and gray sweats.  I called again on Friday but Robert
still wouldn't answer.  In fact, pretty much nobody was calling and I felt
pretty lonely.  Finally on Saturday I got a call, only it wasn't Robert, it
was Gary.

	"Hi beautiful, I was hoping you were back but I didn't hear from
you."  Gary said.

	"Hi Daddy."  I was actually pretty happy to hear his voice even
though I wished it was Robert.  "Sorry I didn't call, I've been busy."

	"That's OK.  What are you doing tonight sweetie?"  He asked.  I
really didn't feel like doing much that night and told him so.  "Are you
sure baby, I have a present for you."  He informed me.

	I was intrigued.  "What kind of present?"  I asked coyly.

	"One you will look really hot in."  Gary replied.

	I thought it over.  I wasn't in the mood for romance or to be with
a guy but I was always in the mood to try a new outfit on.  Besides, I
hadn't been out of the house in days.  Finally I relented, "OK Daddy, I'll
see you in a couple hours."

	I somberly took a shower, careful not to damage my fake tattoo, and
got ready.  Here I was trying not to be such a slut and now I was going
over to let an older guy fuck me just so I could get some free clothes.  It
was sad but I couldn't help myself.  It wasn't going to make me happy but I
wanted to be near someone that night.  I put on my makeup and dressed
fairly conservatively since I knew Gary would have something for me to
wear.  I had on a white top and some tight black pants and a thong so no
panty lines would show.  I then headed out to visit my Daddy.

	When I arrived at his house I didn't get quite as turned on as last
time.  Last time I had been there, his long driveway and expensive looking
house had been a turn on.  I guess that was just my bratty, gold digging
side.  This time, those feelings just made me feel guilty.  I made my way
up the walk and knocked on the door.  Gary greeted me with a kiss.  He was
looking good, but I wasn't turned on that much for some reason.

	My "blah" feelings must have come through because he
asked,"Anything wrong my little girl?"

	"No Daddy, I'm fine."  I replied and tried to smile.

	"Good girl." He replied.  "Now let's have some dinner and then I'll
show you what I got you."  We sat down and had dinner he had just pulled
out of the oven.  It was pretty good; Gary really was a good cook.  The
only thing was I wasn't really in the mood to eat.  My stomach was still a
little nauseous from think about Robert being mad at me.

	After dinner, Gary said "Now it's time for your present."

	"Goodie."  I replied and tried to look excited as he led me
upstairs to his room.

	When we got there I saw an entire outfit laid out on his bed.  It
was really hot and slutty looking too.  It was a tiny little black, vinyl
looking miniskirt with a way to lace it that went all the way up the side
and a tube top that laced up as well.  There was also a pair of boots that
looked like hooker boots and black fishnet stockings.

	"You said you wanted to role play so I had that in mind for the
night."  Gary informed me.

	"Uhh, what kind of role-playing did you want to do?"  I asked, not
sure I wanted to play.

	"Why Hooker and John of course."  He replied.

	"That's great," I thought to myself.  Here I was feeling like a
total hooker and now I got to actually pretend to be one.  "OK."  I said
with a sigh, I'll get dressed and meet you downstairs.

	"One more thing, I got you something else too."  He told me and
went to his dresser and pulled out two fake looking breasts.  "These are
for you too; I want you to fill out the tube top."

	"Wow, he really spent a lot of money on me."  I thought to myself.
"How much money does he actually make?"

	Gary turned around to leave but added "Don't meet me downstairs,
meet me by my mailbox.  I'm going to pick you up in my Lexus."

	"OK Daddy."  I replied and began to get dressed.  I started out by
undressing and then feeling the breast forms.  They felt pretty
interesting, kind of how I imagined real breasts would feel, kind of like a
jelly type feeling.  "No wonder guys like these" I thought to myself.  The
rest of the getting dressed was awkward.  I got the skirt on first but it
was really tight.  If I had had big girl hips I might not have been able to
squeeze it on.  I then put on the tube top and inserted the new fake
breast.  They felt way better than my old fake breasts which were more like
soft Styrofoam.  These must have been expensive.  The problem was then
getting the boots on.  I'm pretty flexible and stretch every morning, but
the boots were nearly impossible to get on with my skirt on so I had to
take that off.  It then turned out that the boots were just too small so I
unfortunately had to settle for just the black fishnets to cover my legs.
I then had to lace up my skirt again and check myself out in the mirror.
My thong looked stupid since you could see the band through where I laced
up my skirt so I peeled it down my legs and reexamined myself.  I really
did look like a hooker!  A spin around to do a quick butt check reminded me
of my tattoo on my lower back.  I hope Gary liked it!

	I made my way down the stairs and outside to meet him by his
mailbox.  It felt exciting but definitely scary to walk outside in an
unknown neighborhood looking like a prostitute.  Luckily it was dark by
then and it was a pretty quite street.  I had never role-played like this
before so I didn't know exactly how it worked but I figured I should just
wait for him to show up.  I felt really hot in these clothes but for some
reason I didn't feel like getting fucked.  I felt sick knowing Robert was
mad at me and this whole night just confirmed I was a whore.  "I guess it
makes it more realistic that I am playing a whore and I don't actually want
to get fucked," I thought to myself.
      I waited outside for about five minutes when I saw a pair of
headlights speeding down the street.  I walked closer to the street until I
noticed the headlights were kind of high up and it wasn't a car but a
pickup truck or SUV coming towards me.  I panicked a little and hurried
back up Gary's driveway (which was hard in the tight skirt and fishnet
stockinged feet).  I heard what turned out to be an SUV slow down so I
turned around and sure enough, it wasn't Gary but just some asshole slowing
down to see what he probably thought was a hooker.  I moved towards Gary's
front door and the SUV slowly moved on.
	I waited there another five minutes or so when I finally saw
another car make its way down the street.  I slowly walked down to get a
better view and when I saw it was a silver Lexus with tinted windows, I
moved a little faster.  The window rolled down and sure enough it was Gary.
"How are you doing tonight sexy?"  He asked

	"Not bad mister, how are you?  Looking for a good time?"

	"Always.  How much is a good time?"

	I had no idea how much prostitutes charged so I paused and said "20
bucks for oral and 40 if you want to fuck my pussy."

	"How much to fuck your hot ass?"  Gary asked.

	"Ummm, a hundred?"  I almost asked.  I really had no idea what to
answer but it was fake anyway.

	Gary reached in his wallet and handed me a $100 bill and told me to
get in the car.  I put the bill in my tube top which was the only place it
would fit and scurried to the passenger seat to take my seat.  Gary then
drove past his driveway and said "I know a discreet park we can go to.  Get
me hard baby."

	I was a little nervous so I started "Ummm, I don't..."

	"Don't worry, we're just going back to my place but get me hard."
He informed me.  I obeyed and took his cock out and rubbed his cock which
was already kind of hard and had precum.  He was really prepared as I saw a
couple Trojan ribbed condoms and a bottle of lube in the drink holder.  We
just drove around the block once and minutes later we pulled into his
garage.  "Nobody comes to this park."  He said, he was really getting into
the role-playing thing.  We exited his car and I grabbed the condoms and
lube and scampered back to his side of the car in my short skirt.

	"How do you want to do it?"  I asked.

	"I want you bent over the hood of the car."  He replied.

	"It's your money mister."  I replied and then dropped to my knees
and added, "Just let me get a condom on you."  I figured a real hooker
wouldn't suck without a condom so I told him to take his pants down and
rubbed him till he got hard.  I then put the condom in my mouth to roll
down his cock.  I withstood the disgusting taste of the pre-lubed condom
and then proceeded to flick his balls with my tongue as I worked some lube
in my ass.  I didn't know if hookers actually licked balls, but I had to
keep him hard as I lubed my ass.  Surprisingly, my clittie barely moved as
I did this.

	When I was ready to go I put my hands up so he could help me up and
then bent over hood of his car.  "OK, let's do this" I said.

	"Wow, when did you get the tattoo?"  He asked in a surprised tone.

	"It's a temp, do you want to fuck or not?"  I was trying to act
like a little bit of a bitchy hooker, but honestly, I kind of just wanted
to get it over with.  This was a hot situation, but I couldn't enjoy it
with what had happened the last week.

	"Alright, let's fuck."  He said and tried to roll my tight skirt up
my hips.

	"Just unlace it."  I told him over my shoulder.

	He loosened the laces, rolled it up my back and lined up his cock.
I gritted my teeth as he worked it in very quickly and started fucking me.
He fucked me like a hooker, without passion.  It totally reminded me of the
way Trevor fucked me and that made me sad again as I thought of what a
hooker I really was.  When I was used to his cock again I started saying
generic phrases without any passion like "That's right, fuck me.", "You
feel so big," and "Cum for me stud."  I basically said these in a monotone
voice like I imagined a hooker might, but plus, I really wasn't that into
it.

	"How many guys have been in your ass today?"  Gary asked.

	"You're the first one this month big spender."  I informed him as I
stay bent over the hood looking straight ahead.  I fixated on the power
drill he had hanging on the wall across from me as he continued to slowly
and rhythmically fuck me.  He wasn't bad at all but my clittie stayed soft
against the warmness of the hood of his expensive car.  "You ready to cum
yet?"  I asked.

	"Hold on."  He replied and reached over my back to get his hands on
the fake breast forms he had bought me.

	"Watch the hands."  I informed him.  "On my hips only."  That was
kind of bitchy of me but I didn't think hookers let you ogle their breasts
and I tried to stay in character.  His hands moved back to my hips and
minutes later he was cumming in the condom.  I just stayed bent over the
hood with my elbows on the hood and told him "Good job stud."  Gary pulled
out and I immediately stood up and took the condom off his cock and tossed
it in the trash can.  "You were the best tonight mister."  I told him.

	"You were great Kara.  You should be an actress."  He informed me.

	"You mean I make a great whore?"  I asked, half kidding.  I was in
a bad mood tonight.

	"That's not what I meant sweetie," He said, "Now give me a kiss."
We kissed and his hands went straight for my boobs.  "These feel great."
He told me.

	"I'm glad you bought them for me Daddy."  I thanked him.

	"Good, let's go upstairs and cuddle."  He said as he led me
upstairs by the hand.  I really didn't feel like it, plus I wasn't really
dressed for cuddling.  He had spent so much money on me though; I didn't
feel like I could say no.

	I lay next to him in bed and he groped me and held me.  He really
liked playing with the fake boobies which I couldn't blame him.  We talked
for a little bit but I really didn't feel like staying.  Nothing against
Gary, I just didn't feel like being with anyone but Robert right then.
Gary started to fall asleep so I whispered to him that I had to go.  He
woke up and said "Awww, so soon baby girl?"

	"Yes Daddy, I have to go.  Can I take these new clothes with me?"

	"Why don't you leave them here.  Then you always have some clothes
if you spend the night."

	I really wanted to take them with me.  If Robert ever called I'm
sure he would love to see me in these, but I didn't make a big deal of it.
I just began taking my clothes off.  The $100 bill I had put in my tube top
came out as I undressed.  I still owed my dad the $200 bucks so I really
wanted to keep it.  I asked Gary coyly, "Oh, here is the money you gave me,
do you want me to leave it somewhere?"

	"You can keep it sweetie.  You earned it."

	"Yayyy!"  I thought to myself and then tried to push my luck.
"Thanks Daddy, I can use this to pay off some bills."

	Gary took the bait.  "Do you have money problems sweetie?"

	"A little Daddy.  My parents are making me pay them back some money
and won't let me use my credit card to buy clothes anymore."  I said in a
little girl voice.

	"Did you spend a lot of money?"  Gary asked.

	"Oh no Daddy, just a couple hundred.  I just had to buy a few
clothes to look good for you.  Now I just have to pay them back is all.
Now I'm halfway there."  I felt a little guilty hitting him up for money
but money didn't seem to mean much to him at all.  Besides, I really didn't
feel like getting a job quite yet.

	"That's nothing."  He replied.  "I don't carry much cash but if you
come over next Saturday I'll take care of the rest of it for you.  I can't
have my little girl worrying about money."

	"Ooh thanks Daddy!  Maybe we can play another game like we did
today."  I said, continuing to talk in my little girl voice.

	"Of course.  What do you want to do?"

	"You pick Daddy.  Just as long as it's not icky."  I giggled as I
continued dressing.

	"What's icky?"  He smiled.

	I laughed, "You probably know Daddy.  Just make sure its fun."

	"OK sweetie, it will be fun."

	I had finished dressing by then so I climbed on the bed and started
sucking Gary's cock.  He was so good to me; I don't know why I had not had
that good of time getting fucked earlier.  I sucked my Daddy's yummy cock
as he watched.

	"Oh Daddy, the boots were too small for me."  I informed him as I
let his cock slip out of my mouth.

	"OK sweetie, I'll return them."  He moaned.

	"Yay!"  I replied and got back to slurping on his cock.  Soon I was
rewarded by the cum in my mouth which of course I swallowed for him.  "OK
Daddy, I have to go.  I'll see you on Saturday."

	"OK sweetie, drive safe."  He told me as I left the room.  I still
hadn't cum so I went home and played with my clittie till I came thinking
about being fucked over the hood of Gary's Lexus.