Date: Tue, 23 Apr 2013 15:16:54 GMT
From: Check It Out <i_wanna_be_a_slut@webtv.net>
Subject: Dressed As A Girl-37

I'm Jimmy James and this is a story of cross dressing and sexual submission
at the hands of my girlfriends father.

============================
Tuesday

All night, I dreamed about what my friends cocks looked like as they stuck
them through the hole. How good it felt when they came in my mouth. How
good their cum tasted and the satisfaction I got from swallowing for
them. Mostly I dreamed about the look on their faces while I laid on my
back with my legs spread. How good it made me feel to have them on top of
me while they fucked me. When I woke up, my pussy was soaking wet and my
cock was straining to get out of it's prison. I needed to cum so bad, that
I wished there was a man there to fuck me.

With no other options, I spread my legs wide, rubbed my pussy frantically
and fingered myself hard, while I fantasized that my friends were
there. Taking turns at giving me what I needed, while the others
watched. When I finally came, I basked in the warm glow of my fantasies. I
reflected on how sexy it made me feel to have all five of them fuck me in
one night. How much I enjoyed spreading my legs and letting my best friends
fuck me like a girl. How good it made me feel to wrap my legs around them
while they laid on top of me, grunted in my ear and filled my pussy with
cum.

When I started to get turned on again, I blushed, got a quick douche, and
went to make coffee. I opened the curtains and got the coffee maker
ready. No sooner did I turn it on and get my cup out than I heard a light
tapping at the door. I turned to see Ed standing there with his robe
open. I giggled, admired his swinging meat and slid the door open to let
him in.

"Good Morning, Come on in." I said with a bright chipper smile while
stroking his cock.

"Good morning. Don't mind if I do." he said as he reached down and caressed
my pussy.

He walked in, took a seat, spread his legs and opened his robe with a big
smile. I smiled back, got to my knees and started sucking. After everything
that had happened yesterday. Having a thick piece of man meat in my mouth
was making me hot. I could feel my pussy twitching with excitement. Without
thinking, I reached down and began to finger myself again.

I sucked his cock slow and easy. I eased it down my throat, pressed his
balls against my chin and looked up at him. He had such a big smile as I
eased the head in and out of my throat while stroking the shaft with my
tongue. Seeing the look in his eye made me feel so good. I continued to
suck it slow and easy. Luxuriating in the way it made me feel to look up
and see a man that appreciated what I was doing for him. It made me think
of Jake and the guys telling me how much they enjoyed my services at the
hole.

Without thinking, I began to suck his cock faster while rubbing my pussy
harder. I began to think about how much I enjoyed sucking his half hard
cock. How good it felt in my mouth. How effortless it was to slide it down
my throat. It made it easy for me to work the whole shaft instead of just
the head.

It didn't take Ed long to respond to what I was doing either. After only a
couple of minutes of that, he groaned with pleasure and filled my mouth
with cum. I deep throated for him as quick as I could. I looked up at him
again while his cock throbbed in my mouth and throat. Between the look on
his face and feeling cum shooting down my throat, I felt a small orgasm
ripple through me. My pussy squeezed, pulled and sucked at my fingers. It
was amazing.

I sucked the head for a little while longer while I watched him relax and
smile down at me. Then I got up and poured us both a cup of coffee with a
big smile. When I was done, I sat down and made a show of squeezing and
massaging my tits for him. He smiled back and watched me closely the whole
time.

"Wow.... This really is fun for you isn't it?" he asked as he reached out
and began playing with my tits.

"It sure is. This is the best thing I've ever done. It really makes my day
to know that I can have so much fun, making so many men feel so good." I
said as I pushed out my chest for him.

"Well I'm happy hear it. It makes my day to know that you enjoy being here
to make me feel this good every morning." he said as he sat back, raised
his cup to me and took a sip.

I blushed brightly, looked down at his cock then looked back at him and
raised my cup to him. "Thanks"

He chuckled at my reaction. "So.... Tell me what you did yesterday. Did you
do anything fun?"

I smiled brightly and began my tale. I told him how excited I was after he
fucked me yesterday. How it made me want to go to work as soon as he
left. How when I did finally get to work, Jimmies friends were there
waiting for me to start my shift at the hole. That they had flashed their
ID's through the hole before letting me suck it for them. What a turn on it
was for me to know who's cock I was sucking. How good it made me feel to
swallow for them.

I told him about going to the club and getting fucked by Buddy first
thing. Then waiting tables in the nude. How excited I was to be nude in a
room full of horny men. How good it was for business and how much I made in
tips.

When I saw his cock begin to get stiff again, I reached out and began to
stroke it gently. I stared at it mesmerized by the way it looked and felt
in my hand. As I told him about Bob stopping by with Jimmies friends after
work. He put a hand on my head and began gently pulling me toward his
cock. By the time I finished telling him how sexy it made me feel to know
that all five of them wanted to fuck me. I was on my knees sucking his cock
while he whispered about how good it felt. I was so encouraged by hearing
it, I cheerfully sucked his cock hard and fast until he blew his load a
second time.

"God, that was good. It's hard to believe such a pretty girl could have so
much fun sucking my cock." he said with a grin as he watched me suck the
head.

"Thanks. Want some more coffee?" I giggled as I stood in front of him nude.

"No, I need to take my wife out shopping." he said as he got up and stood
by the door.

"Ok. Have a nice day." I giggled.

"Well, thanks to you, it's off to a good start." he chuckled as he walked
out.

I blushed as I felt that warm satisfied feeling wash through me and went to
take a shower. Becoming a girl was the most sexually satisfying thing I had
ever done and making men cum was the best part of being a girl. While I
showered, I thought about how good I felt about myself as a girl. How
natural it had become for me to let men use me like a girl. How much fun it
was to be able to have sex with so many men without them knowing. How sexy
it made me feel to have sex with the men I knew from work. How special it
made me feel to be able to provide those services to my best friends and my
neighbor. How happy I was to be getting along with Bob because of it.

I squealed with delight and watched my tits bounce wildly while I jumped
around. I luxuriated in how good it felt to have tits and how feminine they
made me feel. I soaped up and caressed my pussy lovingly while thinking
about how much fun it was to have a pussy. The satisfaction I got from
letting men use me like a girl. How good it made me feel to spread my legs
and provide them with the pleasures of being with a girl. I shuttered,
jerked my hips and almost fell over when an orgasm swept through me. I had
a big smile as I pictured my friends faces while I sucked their cocks at
the glory hole.

When my orgasm ended, I cheerfully finished my shower thinking of Ed, Bob,
Buddy, Jake, the guys from work and all the things I had done for them.

While I dried off in front of the mirror, I blushed at how happy it made me
to do it. How sexy it made me feel to be able to do it. How much I enjoyed
being a girl because of it. How satisfying it was for me to let them use me
like that. How anxious I was to get to work so I could do it again.

Thinking about it made my pussy so wet, I had to do something. I quickly
headed to the dressing room. Strapped in the hula vibe. Turned it on
high. Put in the video of me at Milo's bar.

I sat on the arm of the sofa and began grinding my pussy against it. I
watched how hard I got while sucking cock under the bar. I watched while I
was strapped into the buffet table. I watched as men lined up to fuck
me. But the real turn on was watching the biker 'girl' pull out her cock
and start fucking me. No sooner had it started than I came so hard, I
almost blacked out. My whole world lit up with pleasure. Next thing I knew,
I was on the floor kicking and squealing about how good it felt. It had to
be the best orgasm I ever had.

After that, I put the hula vibe on random. Drank coffee and cleaned the
house with a big smile. I couldn't wait to get to work so I could suck my
friends cocks again. The thought of them and all of the other guys at the
restaurant sticking their cocks through a hole in the wall so I could suck
on them was electrifying. I had never imagined giving men that kind of
pleasure could be so satisfying for me, but it was. In fact, giving men sex
is what made dressing like a girl so much fun. While I got dressed for
work, I couldn't help but to think about how much I was going to miss it
when Cindy and her mom got back.

On the way to work, I turned the hula vibe on high and smiled as I thought
of the days I had ahead of me. What a turn on it was to feel my tits
bouncing all the time. How much fun it was to flash my pussy and spread my
legs for horny men. How many times I was going to get fucked. How many
cocks I was going to suck. The gallons of cum I was going to swallow. Being
a girl was so much fun, I didn't want it to end.

When I got to work, I strutted in with a big smile. Bob met me at the door
and ushered me over to a table. He stood me in front of my friends while I
stood quietly and blushed. He stood behind me, pulled up my skirt and
exposed my pussy to my smiling friends.

"Kitty, Jimmies friends want to thank you personally for seeing them last
night and tell you how much they enjoyed it." Bob said.

They all mumbled their agreement and said how good I was. I could feel my
pussy twitching while the hula vibe was dancing inside me. I just smiled
and gratefully soaked in the praise.

"Well, Thank you. I enjoyed it too. I can't tell you how glad I was that
you stopped by. It was just what I needed." I replied graciously while
pulling up my top and shaking my tits at them.

They all chuckled and thanked me again. I giggled, pulled my top back into
place while Bob chuckled and let go of my skirt. While we walked away, Bob
pulled up the back of my skirt and smiled at me.

"I can see why you like doing that. It was fun. I wish I could be there
when they tell Jimmy what you did." Bob chuckled.

I giggled and blushed. "I know. I can't wait."

"Good Girl. Now get to work." Bob said as he watched me go into the ladies
room.

I waited for the girl at the hole to finish. I quickly stripped down and
took my place at the hole, eagerly sucking cock. Jake and the guys showed
their company ID's. So did a bunch of other guys. I recognized all of them
and eagerly swallowed for all of them. Once again about half the guys that
used the hole were guys from the office. It was such a turn on for me to
suck their cocks. That between that and the hula vibe. I came four
times. It was awesome.

When I was done with my shift. I quickly cleaned up the hula vibe. Put it
in my purse. Fixed my makeup. Went to the club and begged Buddy to fuck me
before I got started. He of course, eagerly agreed and fucked the hell out
of me. I had so much fun giving lap dances and getting fucked in the back
rooms. That the whole afternoon just flew by. Next thing I knew I was nude
at the hole under the stage, happily sucking cock like there was no
tomorrow. I began to think about how nice it was of Bob to help me satisfy
my new found need for cock now that I was a girl. The special thrill I got
from sucking his cock and giving him sex.

Just like the rest of the day. The two hours I spent sucking cock at the
hole was over before I knew it. No sooner had I gotten into a good rhythm,
than Gloria was there to take my place. She was wearing a short skirt. Lace
panties. A form fitting floral top and 3 inch heels. Her face still looked
vaguely masculine, but all in all, she was quite sexy. I continued to suck
cock while watching her get undressed. Once she was nude, she was all
woman. She wasn't very pretty, but her tits and pussy looked so real. It
was amazing. She watched closely as the cock I was sucking throbbed in my
mouth while I gulped down the cum.

When I was done, we said hello. I told her how nice she looked and asked
why she was walking funny. She smiled at me and blushed brightly.

"Well, I got here early so Buddy took me to a room and now my pussy is
sore." she explained.

"Yeah, he does that. You'll get used to it. He's great isn't he?" I giggled
back.

"He sure is. He says you and I are his special snake handlers. He says good
pussies are hard to find and it's not often you find girls that can handle
a cock the way we do." she said with a big bright smile.

"Yeah, we're quite the pair." I giggled.

Just then, a cock poked through the hole. Gloria smiled, put in the soft
tooth guards and eagerly started sucking. I watched her closely while I got
dressed. I watched her tits bouncing wildly as she greedily sucked
cock. She was obviously enjoying what she was doing. It was hard to believe
that I knew a guy that liked being a girl as much as I did.

I walked behind her and looked closely at her pussy. It was sloppy wet and
I could see cum drooling out of it. I reached out and stuck two fingers
deep inside her. It was so tight, juicy and velvety soft that I wished I
had a cock so I could fuck her and find out if it was as good as real
pussy. It was the first time since Cindy left that I missed having a cock.

On the way out, Buddy flagged me down and told me Bob was at my house
waiting for me. I smiled, thanked him and cheerfully headed home. When I
got home, Bob was sitting on the couch watching my videos and greeted me
warmly. I stripped nude, put all my clothes and the hula vibe away. By the
time I was done, Bob had his cock out and smiled at me. I smiled back, got
to my knees and started sucking.

"Good Girl. I see you wore the hula vibe to work today. Did you like it?"
he asked.

I groaned to the affirmative around his cock and smiled up at him.

"Good, I'm glad. That's Mary's favorite toy. She gave it to Cindy for
Christmas. It's good to see you're putting it to good use." he said as he
smiled back.

I was sucking his cock hard and fast when he grabbed my head and began
fucking my mouth. He forced his cock down my throat with every
thrust. After only a few seconds, he mashed my face against his belly and
blew his load deep in my throat while groaning about what a good girl I
was. Once his cock stopped throbbing, he let go of my head and breathed
heavily while smiling down at me. I continued to look up at him and suck
his cock slowly while it softened in my mouth.

"God, you're good at that. You were always good, but all the practice you
got sucking cock at the hole really paid off. Having you at the hole has
been really good for business. Plus I'm getting the best blowjobs I've ever
had." he said while caressing my cheek gently.

I licked and kissed the head of his cock playfully while blushing
brightly. It was hard to believe that hearing how much he liked the
blowjobs I was giving him could mean so much to me. But it was the most
rewarding thing he had ever said to me.

"That's why I'm the best pussy in town." I giggled while licking his balls.

"It sure is. Now go take off the wig, makeup and tits. We've got things to
do." he chuckled back.

I sprang up, did as he asked and walked back in wearing nothing but my
pussy panties. Bob snapped a picture and smile real big at me. Then he had
me turn around, bend over and smile. When I did, he snapped another
picture.

"Perfect. There's some stuff sitting on your bed. Go put it on. We're going
out." he boomed.

I went to my bedroom and on my bed was a full Scottish outfit. Kilt, shirt,
sash, knee high socks, shoes. Everything. I quickly put it on and walked
back to the living room. Bob had me walk around a little and pull up my
kilt to flash my pussy. Which I did without question. He cheerfully snapped
a few pictures while I did.

Then he ushered me out the door and we were off to town. We went to dinner
where he took a few upskirt/upkilt pictures while at the table. He took a
few of me with my legs spread and kilt pulled up. A few more at the bar
flashing my pussy while people stood behind me unaware of what was going
on.

Then we walked around town and he took pictures of me flashing my pussy on
the street. In the park. On the bus. Always making sure there were people
in the background. He had me spread my legs or bend over while people
looked at my pussy and fingered me in public. Then he talked me into
sucking a guys cock in an alley while he took pictures. Always making sure
that my pussy was in plain sight while I did it. He took me to the library
and had me pose for him wearing nothing but shoes and socks. When a guy
stumbled onto us, Bob talked him into taking pictures while Bob and I
fucked. Then I gave the guy a blowjob for helping us and we went back home.

On the way home, we talked about how much fun we had. Bob told me he had
always pictured me as a guy with a pussy and doing all the things we had
just done. He also told me how hot it was to see it for real and thanked me
for helping to make one of his fantasies come true. I giggled and told him
it was my pleasure. After all he had made a good many of my fantasies come
true.

Bob told me since I had been such a good girl, that when we got back to my
house I was to take off the pussy and put on a suit like a real man. That
Buddy and Gloria were going to stop by and he was going to let me help the
two of them get her broken in as a girl. That way she could make some extra
money at the club. I just about squealed with excitement and eagerly
agreed. The thought of fucking her and finding out how good my pussy was,
made my pussy wet.

The instant we got to my house, I ran to the changing room, stripped nude
and took off my pussy like I was told. Bob had me strut around in the nude
while asking if I was going to be ready to fuck 'Glory Hole Gloria'. He
watched my cock get hard while I told him how anxious I was to fuck a girl
like me so I could find out how good my pussy was. Bob laughed, looked at
my cock, called me a good girl and told me to put on a suit. I smiled ran
to the bedroom and got dressed as quick as I could.

When I walked back into the living room, Bob was putting in a new video of
me called 'My Best Friends Girl'. It started with Jimmy standing nude in
the changing room. Putting on everything I needed to become Kitty. Then
getting dressed and walking into the restaurant. Then Jake pulling his cock
out while standing in front of a hole in he wall. Then a side by side of me
kneeling in front of the hole with a smile. Him standing in front of me
separated by a thin black line. It was cut so well it looked like there was
nothing between us. He pressed tight against the thin black line. He poked
a business card at me, I took it, smiled real big and started sucking his
cock furiously. I continued sucking until his cock began to throb in my
mouth while he groaned and humped at the thin black line. Then I watched as
he smiled down at me, put his cock away and walked off.

Watching it made me so hard, I could hardly stand it. It was the first time
I had sucked his cock and it was an amazing thing to watch. It looked like
Kitty was kneeling in front of him sucking his cock and swallowing his cum
with nothing between them. When she was done sucking his cock, the look on
his face is what really got me going. In the whole time I've known him, I
had never seen him look so happy. It was incredible.

Next came the same side by side scene of me sucking his cock at the
club. There was a girl dancing over my head. Grinding her pussy into his
face while I sucked his cock. Just about the time his cock started to throb
in my mouth, there was a knock at the door and in walked Buddy and
Gloria. Bob introduced us, told her to strip and get us some beer from the
kitchen. Without question, she stripped nude while the three of us
watched. Then he had me follow her and show her where everything was.

While we walked I examined everything about the way she looked. The way she
walked and talked. The way her tits and ass jiggled while she walked. How
nice her pussy looked. When she bent over to get the beer, I began
fingering her from behind. Then I asked if she enjoyed working at the
club. I could feel her pussy start to twitch as she told me how much fun
she was having. She said Buddy only let her work the hole for now but that
she loved doing it. As far as she was concerned, it was the best job she
ever had. I just smiled as I took the beer and followed her back to the
living room.

When we got back, Bob and Buddy were sitting on the couch smiling at
us. They took their beers and had me sit between them. Then they told
Gloria to suck my cock. I watched as she smiled, got to her knees, pulled
my pants down and started sucking. It was hard to believe, but she was
almost as good at sucking cock as Cindy was. When I looked up at the TV,
there was Kitty sucking cock at the hole while Jake pulled his pants down
and started fucking her from behind.

I watched him fuck the hell out of me while I sucked cock. I thought about
how good it felt while he was doing me like that. What a turn on it was
when Bob told me that I had sucked off and been fucked by my best
friend. While that was going on, Gloria was giving me a great blowjob and I
blew my load in no time. I pumped my cock into her mouth and groaned about
how good it felt while she faithfully gulped down my cum. When I was done,
I smiled down at her while she smiled back and sucked the head of my cock.

"Good Girl.... You should be proud of yourself." I told her.

"Thanks." she said as she smiled up at me.

Then Bob had me strip nude while Buddy had Gloria get on her back so he
could fuck her. I watched in fascination as he got on top of her and fucked
the hell out of her while Bob and I watched. When he was done dumping his
load deep inside her, she laid there with her legs spread and a big smile
while cum drooled out of her pussy. Then it was Bobs turn. He got on top of
her and fucked the hell out of her while telling her what a good whore she
was. By the time he was done I was rock hard and on her in a heartbeat.

When I stuffed my cock into her, it was so tight and juicy, that it was
hard to believe it wasn't real pussy. I instantly began to fantasize that I
was her and that this is how good it felt while Jake and the guys fucked
me. I dreamed about how good it felt while they fucked me. How good it made
me feel to know that I was giving them pussy that was this good. It's no
wonder they thought I was a girl when they were done fucking me. I looked,
felt, sucked cock and had a pussy just like a real girl. Thinking about it
was such a turn on, that I blew my load after only a minute or so.

"Holy Fuck! That's good pussy." I groaned as I collapsed on top of her.

Bob and Buddy laughed while Gloria giggled.

"You're not done yet ass wipe. Lick that pussy clean." Bob boomed.

I smiled and watched as cum drooled out as my cock pulled out of her
pussy. Then eagerly began licking it clean. I licked and slurped at her
pussy as I gulped down as much cum as I could. I could feel the tip of her
cock poking out of the pee hole of her pussy and I licked and sucked on it
extra hard. When she came, I slurped up and swallowed her cum too.

Bob and Buddy couldn't seem to get enough of watching us. No sooner had she
started to relax then Bob grabbed my ass and started fucking me hard. Then
I heard Buddy tell Gloria to get out of the way while he grabbed my ears
and started fucking my mouth. He hammered his cock down my throat while Bob
slapped my ass and told me what a cock loving faggot I was. Gloria gasped
and giggled when she saw my cock getting hard while they abused my mouth
and ass in tandem.

When they were done, Bob told me I was the biggest faggot/pussy he had ever
seen. Then he told me to get changed so Kitty could suck his cock before he
went home. I smiled and headed for the changing room. Buddy told Gloria to
follow me and give me a hand. When we got to the changing room, I was still
rock hard. Without a word, Gloria got to her knees and started sucking it
furiously. While I watched her, I thought about how good she was at sucking
cock and how good it must have felt for Jake and the guys when they watched
Kitty suck their cocks. Again it was such a turn on for me that I blew my
load in no time.

While I got changed, Gloria and I talked about how much fun we were having
as girls. She told me she had been sucking cock off and on since she was 15
but hardly ever got the chance as a guy. Now that she could get dressed up
and suck cock at the glory hole every night. She was in heaven.

I told her that I started sucking my own cock at 13. I told her how, until
I was 18, I would jerk off until I was about to cum. Then bend over, suck
the head to finish myself off, then swallow, but had never sucked anybody
else's until last week. I also told her about Steve Carver. How he used to
let all the guys in the neighborhood fuck him and how I always wondered why
he did it. Then I told her about finding the pussy panties. Getting dressed
like a girl. Bob catching me. Fucking me until I could hardly walk. Taking
me to the restaurant, then the club and me going wild for cock.

We both giggled about how well things had turned out for both of us. When I
was done getting changed, we looked in the mirror at the two nude girls and
smiled. When we walked back into the living room, Bob and Buddy both smiled
at us.

"Well it's about time! Why don't you bitches get over here and make
yourselves useful?" Bob barked as he and Buddy pulled out their cocks and
smiled at us.

Gloria and I smiled at each other. Got to our knees and started sucking. As
soon as we were done, Buddy told Gloria to get dressed and off they went.

"Did you have fun?" Bob asked.

"I had a great time. Thank you." I giggled.

"Good Girl, I'm glad you liked it." he smiled warmly.

Then he handed me a video disc that had "Jimmy Joins The Chain Gang"
written on it and went home. I smiled went to my bedroom, put in the disc
and drifted off to sleep while watching Jimmy getting fucked by the prison
gang.