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                 K R I S T E N' S    C O L L E C T I O N
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This work is copyrighted to the author © 1999.  Please
don't remove the author information or make any changes
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My Dad, My Pimp 
by PRose1222 (prose1222@prodigy.net)

***

His parents catch a teenage boy cross-dressing and their 
solution to the problem is to make his body conform to 
his choice of clothing. Since the family make the money 
by prostituting the daughter, now they had another child 
they could offer gay johns. (Mm-teen, underage, 1st-gay-
expr, inc, cd, tg, huml, prost)

***

I was fifteen when I got caught wearing my sister's 
clothes. My father was furious seeing his son dressed as 
a girl and he read me the riot act. He put me across his 
knee, lifted the skirt I was wearing, pulled down the 
pink lace panties, and spanked me as hard as he could 
with his hand. When he was done my ass was a bright 
crimson and it hurt to sit even on soft cushions. 

Following a brief discussion with my mother, they 
decided to keep me dressed as a girl and send me to a 
school dance that night with my sister. "If you wanted 
to see what it is like to dress as a girl then you 
should have to let others see you too and experience 
what it really means to be a girl." 

Mother insisted on curling my hair and applying a full 
array of makeup to my face as well as painting my 
fingernails and toenails a bright red. 

It was also decided that I needed to make the necessary 
alterations to my body to conform with my choice of 
clothing. This meant shaving my leg s, underarms, and 
chest. They debated having me pierce my ears, but chose 
not to since there were some clip-on type earrings for 
me to wear. They had me wear a control top pantyhose to 
help hide the bulge between my legs. They insisted that 
I had to wear the highest heeled shoe they could find in 
my sister's closet. I could not believe the reflection I 
saw in the mirror when they were done with my 
transformation. They had seemingly eliminated the boy 
and turned me into a fairly attractive girl. 

My appearance was that of a female, but my movements and 
mannerisms were distinctly male. The rest of the 
afternoon was then spent on lessons in being feminine. I 
learned to walk in the four inch high heels using short 
feminine steps and letting my ass sway freely. I managed 
to master sitting in a short skirt and cross and uncross 
my legs without showing anyone my panties. 

Other lessons included gestures such as tossing my head 
and brushing the hair out of my eyes, as well as wrist 
movements, holding my hands in my lap, and speaking 
utilizing feminine phrases and participating in "girl 
talk" including how to flirt with boys. In spite of all 
the lessons, I was convinced that when my sister and I 
left for the dance that I was going to get caught. I was 
a nervous wreck when I accepted my first dance. 

As he led me to the dance floor, I was sure that this is 
what was going to give me away. I thought about how I 
had pleaded for a reprieve from my punishment, how they 
laughed at me and said, "You sealed your own fate by 
putting on a dress in the first place. You should be 
glad that we don't make you do more as a girl than just 
go to a school dance. Would you prefer we sent you on a 
date with a specific boy? Perhaps you would rather join 
your mother and sister on the street as a prostitute 
where you could suck cocks and get fucked all night?" 

Their threats were real ones. Mother was the main source 
of income working as a prostitute. That was how she had 
met my father and he has been her pimp ever since. He 
also pimps for my sister on weekends. They could just as 
easily put me on the street instead of having me go to 
the dance. As humiliated as I felt I knew it was not the 
worst they could do t o me as punishment. I wasn't 
really sure what made me try on my sister 's clothes in 
the first place. I guess it was just a bit of curiosity. 

I would watch her and mother and notice how pretty they 
were in their skimpy but sexy outfits as they headed out 
to work the streets. I was amazed at all the attention 
my father gave them and how little of his attention that 
I got. Their clothes were different from mine. They were 
softer and brighter. 

I wondered what they would feel like to wear. I also 
wondered if I would as pretty as my sister and mother in 
them. I also wondered if I could get some of my father's 
attention if I wore them. As I tried them on, new 
sensations overwhelmed me. I began to fantasize. I was 
lost in my new dream world and lost track of time as I 
enjoyed the id ea of being a girl. 

I was on the sofa watching a soap opera as I had often 
seen mother and Sandy do, when my father walked in on 
me. He immediately called for my mother and sister to 
come see the little "sissy" as he began punishing me. I 
had wanted his attention, and I was getting it -- full 
force! As a result, here I was walking onto the dance 
floor with another boy, while wearing my sister's party 
dress. It was very awkward in many ways. 

I found it kind of exciting to have them believe I was 
the pretty girl t hey thought I was. It was nice to be 
asked to dance and I was even asked to go on a date by a 
couple of them. I was flattered and even a little 
interested, but knew better than to accept a date with 
any of them. I was in enough trouble at home already. I 
didn't need to invite any more. 

The more time I spent in the female role, the more I 
liked being a girl... I think it was because of all the 
attention I was receiving. The kids in school basically 
ignored me as a boy. I was also turned on by the feeling 
of the female clothing against my body. I knew I would 
spend more time as a girl, but I would have to try to do 
it in secret. 

The hours passed quickly and soon the dance came to an 
end. My father was there to pick us up. "How did it feel 
being a girl, Sissy Boy? Did you have fun dancing with 
the real boys? Anybody ask you out on a date? Your 
mother and I have had a talk while you were here at the 
dance. We have surprise for you when we get home." 

I tried to lie to him and not let him know how much fun 
I really had. My sister told him how everyone had hung 
around me and that I danced almost every dance. She even 
told him that I had been asked out by a few of the boys. 
I was forced to admit that some of it had been fun, but 
said I was glad that it was over. I wasn't, but I 
thought that is what he wanted to hear. "It is not over 
yet, sissy boy. I think you'll enjoy the surprise we 
have for you. We'll see then when it will be over." 

I walked in the door and was led into my parents room. 
Mother was sitting with her camera in hand. I had to 
pose fully clothed and then strip to my underwear for 
some "bedroom photos". Then it was time for the ultimate 
humiliation. 

"Well, sissy boy, you wanted to be a girl, and a girl is 
what you shall be. Women are here to please men and 
provide a sex outlet for them. Your sister was fifteen 
when I changed her from a girl into a woman and now I am 
about to do the same for you. The only difference from 
being a girl to being a woman is experience. A girl has 
not yet fulfilled her place with a man where a woman 
has. 

"Once a girl has shared a bed and been fucked by a man 
then she becomes a woman. Tonight you are going to 
become a woman. When you put on that dress and stepped 
out of being a boy, you told the world to treat you as a 
girl and asked to become a woman to please men and all 
that goes with it. Now kneel before me and pay homage to 
my manhood." 

I knelt as instructed in shock and horror as he undid 
his belt and zip per, letting his pants fall to the 
floor. His penis was released and staring me face to 
face. He was huge! I was terrified. My cock was 
virtually nonexistent compared to his. I begged them not 
to make me go any further and release me from my 
punishment but they just laughed. 

"See how magnificent a cock your father has, sissy boy? 
have you ever seen another one so gorgeous? I have seen 
many, but your father's is the best I have ever seen. It 
is something to be admired and worshipped. Just relax, 
honey, and go with the flow. This is the tool of a real 
man. It is not like that puny thing between your legs. 

"I wouldn't even call what you have a penis. It is more 
like a girl's clitoris and I do know a few women that 
have clitorises larger than you. If you had developed a 
penis then I would have made a man out of you on your 
fifteenth birthday, but instead you are about to become 
a woman and learn how to satisfy a real man. I guess 
that under the circumstances this is more fitting for a 
sissy boy like you. Go ahead and honor a real cock by 
starting with a kiss. 

"Take it in your hand. Fondle it. Explore it. Make love 
to it. Kiss and tickle his balls. Use your tongue to 
lick that big thick lollipop. Open your mouth and let it 
slide inside. Tilt your head a little more and relax 
your throat. You are learning to be a good cock sucker, 
sissy boy. It is easy to see that you are enjoying this. 
Wait until later when he fucks you with it and then 
we'll talk about real enjoyment." 

I swallowed hard and then went to work sucking my 
father's cock. Mother was right. His cock was something 
to be admired and I wanted to be the girl. I wanted him 
to be pleased with the way I sucked his cock. I did the 
best I could and my mouth went up and down his thick 
juicy piece of meat. 

When I started I thought that it was going to taste 
terrible, but I was pleasantly surprised. It was salty 
and yet it had a sweetness to it. I couldn't wait to get 
the load of cum from him. I continued to do as mother 
instructed and I noticed dad begin moaning and soon I 
felt spurt after spurt of his rich cream filling my 
mouth and I struggled to g et every drop of it. I 
continued to suck even after he softened. I wanted more. 
I actually got excited when he became hard again. 

"Now lay on your back and we will complete your 
transition from a girl to a woman. I'll be as gentle as 
I can, but I am afraid there is always a little pain in 
every first time. It soon turns into a pleasure you will 
want repeated over and over." 

I removed my panties and lay upon the bed. My legs were 
raised high into the air and placed over my father's 
shoulders. They were spread wi de for him. I was nervous 
as he began pushing his cock into my asshole. 

I felt it tear open for him. The pain was incredible and 
I screamed in both terror and pain. He inched it in a 
little at a time, pausing each time I screamed so I 
could catch my breath and get used to it. I don't know 
how he managed, but after only a few minutes he had 
worked it all the way in. 

He paused briefly for me to relax and then began to ease 
it out. He repeated this process slowly several times 
until it no longer hurt... Just as I had been told, it 
had become pleasurable. He picked up the pace, fucking 
me hard and fast. I cried out for him to go faster and 
harder. "It feels so wonderful inside me. Faster, dad, 
stuff me with that cock of yours! I need it so badly. I 
want to be a woman tonight. Fuck me harder! Cum inside 
me and fill me with your manhood." 

I continued to beg him to go deeper. He continued to 
drive his cock into me until he was ready to shoot his 
load. He grabbed my hips and made one final plunge, 
shoving it as deep as it would go. He held it there. 

I felt every spasm as his cock emptied his warm cream 
into my bowels. I was in a state of ecstasy as he 
collapsed on top of me. We lay there together until he 
softened and slipped out of me. My father then rolled on 
to his back to relax. I still wanted more so I lifted 
myself up and crawled between his legs to lick any 
residue that I could find. To my amazement and his, he 
began to get hard a third time. 

It was mother who interrupted us from going at it once 
again. She brought us back to reality that I was being 
punished and humiliated. She made me beg my father to 
fuck me again and she had me agree to remain a girl for 
the entire weekend in return for his favor. I had 
enjoyed being fucked so much and wanted it so badly that 
I would have agreed to anything to have him fill me once 
again. 

"Since you will be a woman for the rest of the weekend, 
your father can have his sexual needs met by you 
tomorrow night while your sister and I are out turning 
tricks. As a final degradation, sissy boy, you will have 
to eat all the cum from our pussies when we get home in 
the morning. 

"We told you that you would want to get fucked again 
once you experienced a real man's cock. There is nothing 
like a good hard cock inside you is there? It is every 
woman's dream to be with a real man. Considering that 
puny thing between your legs you will probably be better 
off remaining as a woman. Especially since you enjoy 
being fucked so much you are willing to beg for it and 
trade away your manhood to get it. 

"When this weekend is over, I know you are going to have 
such a satisfied ass from the fuckings that you'll be 
receiving and I know you are going to dress up again. 
Just a word of warning, don't let us catch you doing 
it." 

My father again laid me upon my back, raised and spread 
my legs and wasted no time plunging deep into my ass. 
His cock slid in easily and we soon fell into a rhythm 
as my hips moved to meet his thrusts. I felt no pain and 
experienced nothing but pure pleasure. He fucked me 
hard, fast and long. My own cock had not been touched at 
all that night, but as he continued to pump in and out 
it ejaculated all over my legs. I shuddered from the 
climax. 

My father took no notice and continued to work his cock 
in and out of my ass. When he finally exploded inside of 
me, I shuddered once again as another load escaped from 
my own cock. We collapsed together and remained in an 
embrace until he softened and slipped out of my a ss. He 
rolled on his back and I deftly moved down to clean his 
cock. I had hoped to get him hard once more, but it was 
not to be. 

"Let your father rest now, honey. There will be plenty 
more for you tomorrow and Sunday. Let's get you cleaned 
up and ready for bed. We can have a little girl talk at 
the same time." 

She took me into my sister's room after having me shower 
and use a douche in my ass to clean out my father's 
semen. She whispered something to my sister which caused 
Karen to giggle. Karen went to her nightstand and got 
something out of the drawer. "Here you go little sister. 
It is called, 'the satisfier'. 

It was the present mother gave to me on the night Daddy 
took my cherry. Now I am passing it onto you on the 
night he has taken yours. it is not the same as having a 
real one fill you, but it sure can fill in the gaps when 
one is not available. Let me show you how it works." 

She had me lay on my back, grip it at its base, and work 
it in and out of my ass. it felt good and I got into a 
nice rhythm with it. My sister and mother laughed at me 
for wanting to be fucked so badly. They looked at each 
other and acknowledged there was a new girl in the 
family. They knew I would be using the dildo all the 
time and dressing as a girl again. My sister decided to 
show me another little trick with the dildo before 
having me dress in a pink satin baby-doll nightie and 
going off to bed. 

"I sleep like a baby and wake up horny when I do this, 
Sissy. Push it in as deep into your pussy as it will go. 
Now turn on the switch at the bottom. I love the 
vibrations. It feels wild, doesn't it? Leave it there 
all night and enjoy the feeling. Here is a nightie for 
you to wear that should make you feel a bit sexy, 
Cecilia. In the morning I'll help you choose an outfit 
to do chores in and one for later that will please 
Daddy." 

"Goodnight girls. Sweet dreams, sissy boy. I hope that 
dildo keeps you satisfied and I can't wait until we 
catch you dressed again. We'll be waiting and watching. 
I've got some ideas for your next excursion into 
womanhood. Be prepared for total humiliation." 

I took my sister's advice and left the dildo in my ass 
with the vibrator turned on. I was surprised how relaxed 
it made me feel. She was right I slept like a baby all 
night long, but in the morning I was horny as hell and 
wanted desperately to be fucked. I didn't have the urge 
to jack off like most other mornings. This feeling was 
different. I wanted my ass filled with a cock. I wanted 
to be a woman and be filled, not do the filling. 

I really couldn't believe how strong the urge was. I 
went into my sister's room to get dressed and we began 
to talk. I told he r how I felt and soon we were 
discussing why I dressed in her clothes in the first 
place. I opened up to her like I've never done with 
anyone i n the past. she seemed so sincere and friendly 
that I told her everything including wanting Daddy's 
attention. 

"Well, Sissy, how much would it be worth to you if I 
arrange for you to get fucked right now? Would you be 
willing to do my chores as well as yours? How about 
going on a double date to the senior prom attending as a 
girl? That means your date would be a guy." 

I wanted it so bad that I agreed to anything she wanted 
without even thinking about the consequences. She put an 
agreement down in writing that I would do her chores and 
go to the prom as a girl and with a date. I signed it 
and she went into her nightstand as she had the night 
before pulling out another dildo. This one was attached 
to a harness which she quickly strapped to her body. 

I was in amazement as I stared at the cock between her 
legs. She made me lubricate it with my saliva wanting to 
see how good a cocksucker I had become. When I had made 
it good and moist, s he announced that it was time for 
me to get the fucking that was coming t o me. I laid on 
my back and spread my legs as I had done for my father. 

"You're a bitch in heat, Sissy, so I want to treat you 
as one and do you doggy style. I am going to fuck your 
ass until you have an orgasm, bitch. That should take 
care of your need for a while. I wonder what mot her is 
going to do when she sees you in a prom gown next 
Friday? Remember her warning? We have an agreement and 
I'm not letting you out of it. I like having a sister 
instead of a brother. 

"Knowing mother, she'll keep you as a girl all next 
weekend too. I also think she'll give you permission to 
go to the all night beach party with us after the prom. 
I know she'll make sure you get a good fucking and I 
think she mentioned that next time she would take you to 
get a perm. That will give you a girl's hairdo for a 
month or two. What do you think she will do, Sissy?" 

I felt so humiliated as she continues taunting me as she 
fucked me hard and fast. I was extremely surprised as I 
ejaculated all over her sheet s without being touched. 
She made me lick up my cum before helping me clean up 
and dress in a halter top, red satin hot pants, and high 
heeled sandals. She pulled my hair into a pony tail and 
escorted me down to breakfast. She immediately showed 
mother the agreement that I had signed and I saw a 
wicked smile come across mother's face. 

She then told me that once I put on the dress to go to 
the prom I was going to be fair game for her and my 
father's wrath. I just hung my he ad and acknowledged 
that there was no way out of it and wondered what they 
had turned me into, or did we just find out together 
that this was my true identity all along? I asked what 
they were going to do to me after the prom and if there 
was any chance of a reprieve? My father walked into the 
room as I asked the question and demanded to know what 
was going on. 

He was shown the signed agreement and he nearly flew off 
the handle as he stated that if I went through with 
going to the prom, and since there was a signed 
agreement that I would not be let out of, that I would 
spend the weekend as a girl and this time I not only 
would satisfy my father sexually but my date as well. I 
was also informed that I would share in all the "woman's 
work" around the house as well as dress as a girl to go 
buy my prom gown and that I would have to wear girl's 
underclothes all week even under my male outer clothes 
and that I must wear only dresses at home. 

I protested when they extended my punishment to include 
the entire week. They just laughed and said I should 
have been a bit more discreet in my agreements, but that 
by signing such an agreement I made myself available for 
whatever punishment they decided upon and that if I 
didn't stop arguing they would dress me as a girl the 
entire time and not allow me male outer clothing at any 
time including school. 

They also said that if I didn't watch myself I would 
find myself out on the streets with my mother and sister 
turning tricks. What could I do? I shut up immediately. 
It then became my duty to wash the breakfast dishes and 
begin doing the laundry. 

I did all the household duties assigned to me that day. 
Basically I was treated as a hired maid and even had to 
serve them as they made requests for soda, coffee or 
snacks. I didn't dare complain as I knew they were just 
looking for a reason to increase my punishment. 

My father also used me sexually several times during the 
day, and I definitely wouldn't complain about that as he 
fully satisfied me and I hoped that I had satisfied him. 
That evening my mother and sister headed out to make 
some money on the streets and I was left with my father 
to be his for the evening. 

They did ask me if I would like to turn a few tricks of 
my own, but I was afraid of what would happen if anyone 
out there found out that I was not a real woman. Street 
queens have been known to turn up injured or dead. I did 
not want to be amongst them. "Don't worry dear you will 
get your turn on the street and we'll make sure you are 
safe, well trained and satisfied. You two have a good 
night." 

As soon as they drove off, father wasted no time and 
took me straight to the bedroom. 

END

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The author does not condone child abuse, this story is 
meant as an erotic fantasy not depicting anything in 
real life. Anyone acting out such scenarios in "real 
life" can look forward to many unproductive years 
getting it up the butt by a fellow convict in their 
local prison system.
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Kristen's collection - Directory 69