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HALLOWEEN
I started dressing as a girl for Halloween when I was ten.
It has become a tradition since. It was my sister's idea to
start with. We are twins and she told mother that it would be
fun for the two of us to dress as twins on Halloween. Since I
am a boy, it was not normal for me to wear female clothing, but
somehow Mother went along with her idea and asked what costume
we could both wear. I wanted to be an Indian. My sister wanted
to be a mother with a child. Mother compromised and had us both
be Indian squaws with papooses. I protested having to be a
girl, but mother said that if I continued to argue she would
make me be a girl all day, rather than just go trick-or-treating
and to the school party as one. I was the laughing stock of the
neighborhood and it took weeks before my friends stopped teasing
me. Mother thought it was great to have us dressed as twins so
when next year came around, I found myself dressed as a
princess. The years that passed since each found me in a
different female costume which matched my sister's. The
sequence of costumes was as follows: 1.) Indian squaw; 2.)
princess; 3.) harem girl; 4.) ballerina; 5.) cowgirl; 6.)
southern belle; 7.) French maid; and 8.) nun.
The most I had to endure was some mild teasing at school and
a little embarrassment while dressed, until this year. It was
our senior year at school and Michelle decided to get me to
agree to going to the school party as a prostitute with her. We
dressed in tight sweaters, short skirts, and very high heels.
She used a lot of makeup on us and gold chain jewelry to
complete our outfits. I even let her pierce my ears to get the
full effect. we wore long blonde wigs and fake furs. We
arrived at the party and her boyfriend greeted us at the door.
He complimented both of us on how pretty we were and asked if we
wanted him to be our pimp. We jokingly told him yes. He knew
how we were going to dress for the party and came appropriately
dressed as a pimp. I knew girls weren't interested in guys
prettier than them, so I just kind of excused myself and headed
toward a corner seat to be a wall flower for the night. I sat
in a chair near the buffet table. A few minutes later, the
captain of the football team comes over to me and tells me that
he has paid my pimp fifteen dollars for a blow job from me. I
laughed it off as a joke, when he starts to get a little angry
with me. My sister and her boyfriend come over to see what the
problem is. They told me that they were only having a little
fun at my expense. They apologized to the football captain and
offered him his money back. He refused and demanded that I go
with him into the boys' room and give him what he had paid for.
We explained that I was really a boy and that it was just a
costume not a profession. He said he knew and that he was tired
of seeing me come to these parties as a girl every year. "If
you want to be a girl so badly then you are going to have to put
out like a girl. I'm not letting you off the hook this time.
In fact, I think I'll have you do the entire football team
tonight, slut! You are her pimp, how much for the whole night
with her and a gang bang?"
We tried once again to get him to back off, but he was
determined to go through with it. I finally agreed to go
through with the original deal to just suck him off, so as not
to cause a scene or be forced into any more. I walked with him
to the boys' room. My sister and her boyfriend follow right
behind. They wait outside while I go into a stall with him. He
immediately drops his pants and orders me to get on my knees and
suck him dry. I feel so ashamed, but know that I have to do it
or face the consequences which are much more severe and painful.
I drop to my knees, take a deep breath and a hard swallow as
I come face to face with his cock. I lick it at first as I try
to figure out its taste and how bad I expect it to be. The
texture is soft and smooth. The white pre-cum is salty and yet
it also has a sweetness to it. I let it in between my lips and
I start taking as much of it into my mouth as I possibly can. I
am surprised to find that I could take it all in and that it was
not as offensive as I thought it was going to be. I still
wanted it over with so I quickly began sucking on it and sliding
it in and out of my mouth. I'm not sure how long it actually
took, but I soon received the rewards of my effort as he began
shooting spurt after spurt of his warm liquid down my throat. I
had to swallow or choke. He went on for minutes and when he
finished he made sure that I licked him clean with my tongue.
"That was the best damn blow job I have ever received. You are
better than any girl in this school. Come along , cunt, lets go
back to the dance and I'll see about getting you some more
customers. Anything that good has to be shared. Don't give me
any argument. I know now that you are nothing but a little
pussy. A man would never do this without a fight. As far as
I'm concerned you've sealed your fate as a slut. You are the
best cocksucker I have ever met. You really get your money's
worth with you. In fact I want some more of you later. I want
to see if you fuck as good as you suck. Your pimp said it was
fifteen for a blow job and thirty for a fuck. The way you serve
your men he is charging too little. You've come as a girl once
too often and now you are going to pay for it, or rather I
should say I'm going to pay for it and you are going to show us
what type of whore you really are."
He walked out, leaving me in a heap of tears and disarray.
My sister's boyfriend came in to see if I was okay and to get me
out of there as he had been told to get ready for a lot of
business to come my way. He helped me out to my sister who
quickly brought me into the girls' room to clean me up. She
said her boyfriend was going to get his car and we were all
leaving the party. I just continued to cry and tell her how
dirty I felt and what he had said to me about being the best he
had ever seen and how he did not want to just let me go but
wanted more of me and to tell others about what we had done.
she finally got me to stop crying and we headed out the door.
Her boyfriend had brought his car right to the front door. she
slid in next to him and I slid in next to her and then we drove
off. They asked if I wanted to go home and face mother or just
go somewhere to talk for a while. I was not ready to face
Mother, so we drove to Kenny's house. The only one home was his
older sister. His parents had gone away for the weekend. She
overheard our conversation and offered to leave us alone for
which we were grateful. She called one of her girlfriends and
left the house. My sister got me to describe the blow job and
how I felt. She was surprised to find out that I liked it while
I was doing it, but understood how I felt when he was done. She
then surprised me by asking if I would ever want to do it again?
"It is an honest question. You said you liked the taste of it,
and that having a cock in your mouth gave you a strange
sensation in your own, that you found pleasure in. You also
said you felt like you were getting a reward for your efforts
when you were able to make him cum in your mouth. So tell us
the truth, would you want to suck another cock?"
"Being honest with you, I think it would depend on the
circumstances. I might." I can't believe those words came out
of my mouth. It was true I probably would suck another cock if
the opportunity was there. I then went even further as I asked
her if she had ever done it? She told me she had and described
how she had sucked Kenny off the night before. she also
admitted that she and Kenny had fucked a few times. This peaked
my curiosity and I asked her to tell me how it felt. I found
myself wondering what it would be like to be a girl and get
fucked by a guy. What was happening to me? Was I turning gay?
Did I really want to be a girl? I didn't know. I was feeling
confused and overwhelmed. I also wondered what was going to
happen when I went back to school and had to face the boy I had
sucked off. Would it be just mild teasing this year? My sister
tried to comfort me and ease my thoughts and so did her
boyfriend. He reached out and put his arm around me and let me
cry on his shoulder. He said that under the circumstances, he
saw my crying as that of a girl and that I had the needs of a
girl at that time to be held and loved. He said that he got
caught up in the moment and forgot that I was really a male. My
sister laughed a bit and said he was right, that I was acting
more girlish than masculine. Even I had to laugh with them. It
was true. I was feeling like a girl and I wanted to be treated
like one. I apologized to my sister for stealing her
boyfriend's attention.
Kenny said it was kind of nice to have two beautiful girls to
fuss over. He then suggested that we each get on one side of
him and hug him. My sister looked at me and said, "Go with it,
Jennifer, let the girl in you come out and lets explore her
together. I can handle sharing Kenny with you for tonight
anyway. We'll show him some gratitude for being there for us,
okay?"
"Okay, that sounds fun."
We each put our arms around his neck and gave him a kiss. I
followed her lead and just copied everything that she did. It
wasn't long before we were loosening his belt and pulling down
his pants. My sister offered me the choice of sucking on his
cock first and I just dropped to my knees and didn't think twice
about it. I licked it to see if it tasted any different from
the other cock I had tasted earlier, and was surprised to find
it a bit sweeter, maybe it was because I wanted to suck this one
and was forced to do the other one. I don't know why, but I
liked it even more. I quickly let it slide into my mouth, and
gobbled up every bit of it that I could. Kenny was much thicker
and a little longer than the football captain's was. I still
managed to get it all in but it was stuffed and I had to fight
off a gag reflex to do it. I continued to suck until it filled
me with the warm sweet milk of my desire. I licked him clean
trying to get every drop of his cum that I could. I found
myself wanting more. My sister watched how I had attacked his
manhood and she could see that I had enjoyed it. "We're not
through yet, by a long shot. I haven't had my fill yet. What
do you say Kenny, are you willing to satisfy two women tonight.
Lets move to your bedroom and have another round."
We gathered up his clothes and carried them to his room.
Michelle had Kenny sit on the bed as she took a turn sucking his
cock. I was amazed at how quickly it became hard again. She
then decided that I should do a striptease for his entertainment
while she continued to suck his cock. I tried to do my best
dancing and to be as sexy as I could as I removed my clothes. I
was caught up in the emotions and desires of the scene and I was
having a good time. I stripped all the way to my bra and
panties. I didn't dare go any further as I was afraid it would
spoil the effect of my masquerade. I was enjoying being a girl
at this point and I did not want my masculinity coming out. My
sister then stopped sucking his cock long enough to tell me to
remove the bra. She reminded me that the breast forms were
glued on and looked quite natural just hanging there by
themselves. She also reminded me that my penis had been taped
and tucked in such a way that it could not be seen without
actually getting between my legs. I took off the rest of my
clothes as she instructed and then she told Kenny, "I think it
is time my sister became a complete woman. Don't you? she has
seen what it is like to suck a cock, but the difference between
being a girl and being a woman is having been fucked by one.
Kenny are you willing to fuck my sister and make her a woman
tonight?"
"Jennifer, are you willing to let me fuck you? I don't want
to do anything against your wishes. I'll be as gentle as I can
with you, but there is still going to be some pain involved.
There always is for anyone's first time. Do you wish to
experience what it is like to be a woman or remain a girl?"
I could not believe my ears when I told him, "I love being a
girl, but I want you to make me a woman. Yes, Kenny, please
fuck me. My cunt-hole aches to be filled by you. Michelle,
thank you for this."
With that Kenny pulled me onto the bed and drew me close to
him and kissed me passionately. He rolled me onto my back and
began to let his hands roam all over my body. I wish I could
have felt the way he was fondling my breasts. I could only
imagine the true sensations, but just thinking about it was
sending shock waves through my system. He worked his way down
my body to my legs. he ignored my trapped cock and went
straight for the only open hole I had down there. He began
working his fingers in and out of me. First one finger then two
then three. I felt a little tinge of pain but he was so loving
and gentle that it quickly turned to pleasure. He wasted no
effort removing his fingers and filling me with his cock. He
entered me slowly at first and worked it deep inside me an inch
at a time. Once he got it all the way inside me he began to
back it out, just as slowly as it went in. It felt wonderful.
He began to pick up his rhythm with each subsequent thrust.
Finally he was working it in and out hard and fast and it was
giving me sensations inside that were putting me over the edge.
My whole body was responding to him with desire and satisfaction
all at the same time. I was shivering with delight as his body
tensed and he gave one hard thrust and held himself deep inside
me. I felt every pulse as he filled me with his seed. I
thought it felt good having him cum in my throat, but nothing
could compare with the way I felt at that moment as he gave me
his cream in my ass. I simply clamped onto him with my legs and
squeezed as tight as I could hoping to trap this moment in
eternity. I did not want it to end. He collapsed on top of me
as his spasm subsided leaving his cock inside me, he kissed me
and then lay there holding me with my legs still in the air.
I was in the throes of ecstasy. I knew that I had received
something that would change me forever. I felt I really had
become a woman at that moment. I felt joy and release. I
wondered if I could remain in this state forever. The moment
ended as he softened and slipped out of my hole. My sister told
me to clean his cock off with my mouth and then let her take my
place. She had me continue to suck him until he became hard for
a third time. It was now her turn to share the bed with him. I
watched as she spread her legs and he drove his penis into her.
As they fucked I was remembering every moment I was in her
place. Even the memory sent shivers through me. He emptied
himself one last time into her. When they recovered from their
orgasms we saw that it was time to go home. We cleaned up and
Michelle helped me to redo my makeup and dress. Kenny drove us
home and walked us to the door. Surprisingly he gave us each a
kiss goodnight. I didn't mind the kiss, but wished I could have
more of his cock instead. We knew that we could not tell mother
about what we did so I let my sister tell her about the dance
and how boys were trying to get me to dance with them and asking
us how much for sexual favors. She laughed, and asked how I
liked being kissed. I didn't know what to say in response. I
didn't even know how she knew, until I noticed Michelle's
lipstick had been smudged and knew that mine must be too.
Michelle answered her, "We played a little trick on Kenny and
wouldn't tell him which of us was me at the door to say
goodnight. He grabbed a hold of Johnny and kissed him before we
had a chance to say anything or stop him. It was all in fun. I
like having a twin sister. I wish Halloween came around more
often. Come along, Jennifer and I will help you remove your
makeup. I'll also loan you a nightgown if you'd like to be a
girl tomorrow too. Can't blame me for trying."
I did want to be a girl again, but that would have to be a
secret that I could not tell to mother or anyone else for that
matter. I did tell my sister and she said we would discuss it
in private some time. I did wear one of her nightgowns to bed
that night. I liked the feel of women's clothing a lot more
than I liked male clothing. There were changes coming in my
life but I didn't know what, how, or when. I thought about all
that had taken place as I fell asleep that night. I was
confused, because I know I shouldn't have done it, but I enjoyed
it with Kenny and Michelle. I enjoyed sucking the other cock
but not being forced into it or left open for public ridicule.
I still wondered what was going to happen when I went back to
school on Monday. I had one day to go through first before I
would find out. Mother had planned to visit Grandmother at the
nursing home and taking her shopping. She left Michelle and I
at home. I waited until she left before getting out of bed. I
wore the nightgown down to the kitchen to have some breakfast.
"Good morning, Jennifer. How did you sleep?"
"I slept fine, Michelle. This nightgown is so soft. How did
you sleep?"
"I had a good night's rest. I always do after having sex
with Kenny and last night was even more fun with you being
there. I see by the fact that you are still wearing the
nightgown that you do want to spend more time as Jennifer, don't
you?"
"Yes, I do. I liked last night in spite of all that took
place and it is hard to go back to being a boy under the
circumstances. What am I going to do about it? I can't stay a
girl, and I certainly should not have liked doing what we did
last night, but I want more. I am so confused. How do you feel
about your brother becoming your sister? Tell me what you are
thinking about last night and what might take place in the
future."
"I wish you had been born a girl. I always have. It would
have been nice to have someone to share intimate things with and
go shopping with. I realize that last night presents a somewhat
awkward situation for us, but I'm glad you are not angry about
it. I also am glad that you want to be my sister some more. I
like having talks like we are having right now. It is too bad
that we can't do this in front of mother but she would never
understand it. She is gone for the day and won't be back until
late. How about dressing up as Jennifer and going shopping with
me at the mall?"
"Do you really think I could get away with it? What if we
ran into people that we know?"
"We'll just tell them that we made a bet and you lost and had
to remain as a girl for today. It will be fun and I don't think
we would run into anyone. What do you say?"
"How are we going to get there? I don't want to walk that
far and we can't drive, because Mom has the car."
"I could give Kenny a call or I could ask Priscilla if she
wanted to go? Maybe we could just take the bus?"
"The bus sounds okay as long as you are sure I can pass as a
girl even in the daylight."
"We are twins aren't we? You look as much like a girl as I
do. We can even wear matching outfits. We don't need to dress
up, we'll wear jeans and sweatshirts. I'll wear blue jeans and
you wear my pink ones. We'll wear some high heels for the fun
of it. Let's get dressed and be on our way."
She helped me tuck my cock between my legs and tape it in
place. I wore pink panties and a matching bra. We glued the
false breasts on my chest to fill out the bra cups. I also wore
pantyhose, pink jeans and a white sweatshirt. She gave me her
red spiked heeled shoes. The heels were four inches high and
took a little practice before I could walk gracefully in them.
I had to take short little steps or I would lose my balance.
She gave me a purse and a school jacket to wear. She wore the
same type of outfit, except that her jeans were blue and her
heels were also blue and had only three inch heels. She put on
her rabbit fur jacket and led the way out the door to the bus
stop. A few cars passed by as we waited, but the only thing
that happened was one carload of boys whistled at us as they
passed. The bus ride was uneventful and we got out at the mall
entrance. I didn't know what I had agreed to until we went in
the first dress shop and my sister started holding up dresses
for me to try on. She was not going to let me get out of going
into a dressing room and model some clothes for her. She even
got me to agree that before we left we would each buy a matching
outfit. She decided that the outfit would be a party dress with
all the matching accessories. We even purchased earrings that
matched. We could not find any clip-on type so we had to buy
them for pierced ears. We agreed to have that conversation
later. We also bought matching aerobic outfits and sneakers.
It was fun and we kept shopping into the afternoon. We had
lunch in the food area of the mall.
The afternoon turned a bit scary when I noticed the football
captain and a few of his friends going into one of the sports
stores. I was sure we were going to run into them and I begged
my sister to get us out of there. I was thankful that she
agreed and we headed toward the bus stop. The bus took its time
getting there and I felt fear every minute that passed. I knew
that I would probably be safe, but I couldn't help but worry.
The worst possible thing happened when the bus arrived. The
football captain and his friends also got on the bus. They
walked to the back of the bus and did not say a word to us, but
I saw each of them eye us over once or twice. They got off
before we did and I thought that we had got by without an
incident, but it turned out they had decided to take a shortcut
through the park and were waiting for us when we got off at our
stop. We started walking towards home when they caught up with
us and asked why we had left the party so early the night
before. "I see you are a sissy faggot just as I thought you
were. You dress as a girl even when it is not Halloween. I
still think you need to be taught a lesson, and I still think
you give the best blow jobs around. What do you say, I won't
kick the shit out of you for being a fucking queer provided you
agree to blow me and my friends this afternoon. You either go
down on your knees voluntarily or we'll beat you and then we'll
still have you serve us sexually. How do you want it?"
I looked to my sister for some sort of reassurance or
alternative. I knew there was no other choice but to go with
them and do as they asked. I gave my packages to my sister and
told her not to worry about it and that I would get home as soon
as I could. They were content to have me and let her go home.
They took me into the park and behind a clump of trees and there
I was told to kneel and to open my mouth. One by one they
dropped their pants and I sucked their penises. I swallowed a
few gallons of cum that afternoon . A couple of them used me
twice. I was thankful that they didn't decide to fuck me. They
were content with blow jobs. They warned me that in the future
they may want to use me again and that I shouldn't run from them
or they would do even more to me. I walked home with tears
flowing. They laughed at me saying, "Look at the little sissy
crying just like a real girl. Maybe we should keep her as a
girl when we go back to school. She could even be a cheerleader
and be ready to serve us even on the road."
They walked with me to the bus stop and continued to tease
me. I was glad when they left me alone and I headed straight
home. I would have run home but I was still wearing those four
inch high heels. As I approached the house I had another shock
to deal with. Mother had come home early. There was nothing I
could do but walk into the house and hope that I could get to my
room before she saw me. It was no use. she saw me as soon as I
walked into the house. She made me tell her why I was dressed
in my sister's clothes and where I had been. I tried to lie to
her that I had been at the mall with Michelle, but that just
before the bus came I had a need to pee and ran to the ladies'
room. I told her that I missed the bus and walked home.
Michelle tried to back up my story, but mother saw through our
cover up and demanded the truth. Michelle tried to take the
blame for me dressing as a girl, but eventually the whole truth
came out and Michelle and I were both in serious trouble.
Mother disapproved of premarital sex and was angry to find out
that we were both guilty of it. I was in more trouble because I
was doing it as a girl and I was still dressed as a girl that
day. She said being a rape victim was one thing, but doing it
without a fight was not rape. "You are nothing but a whore.
You deserve everything they do to you. Its not bad enough that
you let yourself get forced to do it with them, but you let your
sister's boyfriend fuck you also. What were you thinking?"
There was no way of dodging her anger. She decided that
since both of us were the equivalent of whores, and since I had
seemed to want to be a woman instead of a man that the
punishment for each of us would be two months of voluntary duty
at the hospital as candy stripers. We would have to wear
matching uniforms and I would also have to dress as a girl at
home each day after school and on weekends. We were both going
to have to get a prescription for birth control pills and take
them regularly. She then asked to see what we had bought at the
mall. Michelle brought the bags downstairs. She showed mother
the party dresses and the aerobics outfits that we had bought
and then she showed her the accessories and she noticed that
there were two pair of matching earrings. There was no way to
convince her that I was not planning to pierce my ears. In
fact, even if she had believed me, I think she still would have
pierced them and made me wear earrings as punishment anyway.
The worst part was that she was going to make me wear earrings
to school and twenty-four hours a day to keep the holes from
closing. how would I explain that to my classmates or anyone
else making fun of me. She made us dress up in our new clothes
and called a photographer friend of hers. She was making us get
our portraits done and she threatened to use them as this year's
Christmas card. She also threatened to have them submitted as
our senior class pictures. My sister had no objection, but I
did not want to be seen in my senior year book as a girl. I
hoped that mother was just making idle threats about that.
After the photo session, she insisted on taking us across the
state line to a night club. "Since the two of you are into guys
and sex, I thought the three of us could have a good time
dancing and pick up some guys together. We had to come here
because the drinking age is only eighteen. In our state it is
twenty-one. The two of you are nineteen so there will be no
problem and I have made sure that your licenses are in your
purses. By the way, Michelle, what name have you given Johnny
as a girl. We both need to be calling him by the same name and
Johnny just doesn't seem to fit him as a girl? Oh, I like that!
Jennifer is a good choice and he looks like a Jennifer. Well,
Jenny, I don't want to hear any arguments. You are going in
here as a girl and you will behave as one. You can dance with
any of the guys you want, but no girls. In fact, I don't want
to see you looking at the girls the way we are going to be
looking at the guys. In keeping with your status as a whore,
and I'm speaking to you as well, Michelle, I expect each of you
to be able to attract a guy and get him to go home with us. I'm
sure you know what that means for later and tomorrow morning.
You will suck and fuck him and do whatever it takes to please
him. Are my instructions clear?"
I begged her not to make me go through that and was told that
if I could suck off the football team and be fucked by Kenny,
that I should find enjoyment in being with a man of my own
choice. She would not listen to any of the objections that I
offered. Michelle tried to tell her that she needed to be
faithful to Kenny, but that idea was refused because she said
Kenny was unfaithful to her and that she helped make him that
way by encouraging him to fuck me. She also told her that it
was an indication that she was just using him for sex and that
is all any guy we picked up at the night club would be. She
said that if we did not find guys on our own then she would
choose guys for us. What choice did she leave us. The next
question I asked had to do with my true gender. She said that
we would not tell anyone until we were back at our house. The
only one who would know was the bouncer at the door when he
checked my ID. "And I will bet the only thing he notices is
your date of birth and not your sex."
She was right he never gave my license a second glance and
let us in without questioning my gender. Inside was a bit dark
and smoky. There were guys asking us to dance from the moment
we walked in the door. They bribed us with drinks, tried to use
pick-up lines on us and there was one that just tried to grab us
and drag us to the dance floor. I was glad that mother made
short work of him. She was masterful to watch as she showed us
how to handle the crowd and find the type of guy that fits your
mood. Michelle told me that she had never seen mother so
determined in her punishment before and set about finding a man
to take home with her as we had been instructed to do. She
advised me to do the same. I accepted many dance offers, but
could not get myself to get over the hurdle of actually choosing
a sex partner for the night. Mother issued a final warning as
the hour grew late. She gave me a time limit, before she would
make the choice for me. The time passed and she introduced me
to a man of her choice inviting him to come home with us at the
same time. She left no option for me but to remain his
companion for the rest of the evening. He certainly had a
physical quality that was attractive to any woman, and the bulge
in his tight pants showed a penis of some size. His attitude
was what turned me off though. He knew that women found him
attractive and he expected them to cater to his every whim and
admire him as a god. He was extremely arrogant and rude.
Mother told me in the ladies' room just before he left that I
needed to be exposed to this type of treatment as a sex object,
so that I could truly understand what women put up with and go
through.
I was in a state of shock, knowing that she was going to make
me spend the night with this guy, if he stayed after my secret
was revealed to him at our house. I was sure he would kill me
when he found out that he was attracted to a boy and not a girl.
The inevitable moment came when it was time to leave the
nightclub and return home. Mother took her man in our car,
while Michelle and I had to ride home with our dates to show
them the way. I was having to avoid being discovered in the car
as he continuously tried to slide his hand under my skirt. To
divert him, I put my hand in his lap and began to rub his penis
through his pants. It was all he could do to keep us on the
road. I was actually glad when we reached our house and feel a
little safer. His cock had got even bigger under my gentle
touch. Mother made everyone a nightcap and began the
introductions promising the men a night of sex they would not
forget. She then exposed the secret of my identity and told
everyone why I was being punished and she asked them if they
were willing to help her do it and if they had any other
suggestions for additional treatments. All three of them
commended her on the way she was treating me and volunteered to
assist her in her endeavors. Tony, the guy she had picked for
me at the club also suggested that since the football team had
only gone one at a time that it might be proper for me to see
what it was like to take on two guys at the same time from each
end. Mother had a smile come across her face as she considered
his suggestion. They all agreed that since I wanted to dress as
a woman and have sex as a woman that I needed to be treated like
the whore I had become. They also suggested that since my
sister had a boyfriend and although she forced him to cheat on
her that it really was not any different than what the mother
had done herself by picking up a guy at the club to have sex
with, and that Michelle should be given a reprieve from having
sex with anyone but Kenny. They agreed that she should have to
take birth control pills to prevent pregnancy, but that sex was
okay for her under those circumstances. Mother thought about it
and then agreed with them.
Michelle was off the hook somewhat, but my punishment had
been increased. The man that had come home with Michelle came
over to my side along with the man that I had brought. They
each put their arm around my waist and led me to the couch.
"Well, Jennifer, now that the introductions and the decisions
are out of the way, lets see if you are half the woman you
appear to be. One began kissing me as the other began unzipping
my dress. The dress fell to the floor and then they began
removing their own clothes. I dropped to my knees and started
sucking one cock while fondling the other with my hand. I could
not fight my situation nor ignore that I wanted to suck a cock
or two. I slipped the cock from my mouth and took in the other
one. As I did, I could feel my body being pushed forward and a
hand exploring my rear end. First one finger probed my ass and
then two. It was not my first penetration, and I was looking
forward to the thrills I had felt as Kenny fucked me the other
night. I was not disappointed as his cock finally entered me.
The three of us got into a rhythm that launched us toward
heaven. They came at the same time and what a thrill it was to
have their warm fluid filling both ends. This was the finest
moment of the entire weekend, though I tried not to let anyone
know about it. Who am I kidding? You cannot hide the feeling
of ecstasy that flooded my inner being. You cannot cover over
the smile or the happy tears or the sighs of enjoyment. They
were there for all to witness. My fate had been sealed.
I cleaned each cock and began anew to get them hard again.
In only a few minutes they were ready to go. This time they
took opposite ends. The session lasted longer, but the results
were exactly the same. I was thoroughly satisfied by them.
They each said they were quite happy with my performance as
well. The man that had come home with Mother had fucked her
while the others were doing me, but he decided that he also
liked the looks of my ass and wanted a shot at me. Mother
helped guide him in after watching me suck his cock until it was
hard enough. She was amazed at just how skillful I had become
as a cocksucker. She continued to watch as he pumped me hard
and fast with his cock. He was thicker and longer than anyone I
had ever done before and it felt wonderful as it slid in and
out. It was filling me deeper and deeper with each stroke. He
was moaning with the pleasure my hole was providing him. I
could feel him tense and his cock began to spasm. Spurt upon
spurt of his warm white cream filled my bowels. I squeezed my
ass cheeks together trying to not let a drop get away and draw
him deeper still. My body shuddered as I felt a release from
within. My cock had not been touched, in fact, it had not even
been released from its taped prison. The pressure of it was
just too much and had to join all the emotions and sensations
flowing through me at that moment. We all collapsed in a heap
with the final blast of cum from his cock. Following a time of
rest, we cleaned ourselves off and prepared for bed. The man
that came home with Michelle said his farewells and left. The
man that came home with mother went to sleep with her while the
man I had brought shared my bed that night. Michelle not to be
left out had called Kenny to come over and be with her. Each of
us slept happily.
The next morning I was awaken early by Tony's erection poking
me in the leg. Having enjoyed the night before, I slipped my
head down and began to suck it. I wanted some more of his cream
for breakfast. He awakened to my touch on his cock. It did not
take long for him to come and then he suggested we shower
together. It was fun having someone wash my back and playing
with his penis in the shower. Not knowing how I should dress I
just threw on a robe and went to prepare him some breakfast.
Mother was up and already had most of it prepared. She and
Marty were having a cup of coffee as I entered the room. I
asked mother how I was supposed to go to school looking like I
do. I was referring to the false breast forms that were glued
to my body, and the earrings I was being forced to wear. She
just laughed and said I should dress any way I wanted to, but
that the breasts and earrings were a part of my punishment and I
would have to live with them. She reminded me that I had to
dress as a girl when I got home and that Michelle and I would be
going to the gynecologist to get our prescriptions for birth
control pills and to the hospital to sign up for volunteer duty
as candy stripers. I poured Tony a cup of coffee and gave it to
him as I went back upstairs to dress for school. I wore my male
clothing. I chose the loosest fitting sweater I could find and
a pair of jeans. I knew that I was going to get comments about
the way I had dressed at the party, and the football team could
subject me to further humiliation, but I did not wish to
advertise that I was also being punished by having my body
feminized. I combed my hair over my ears hoping to hide the
earrings. I looked in the mirror and knew that I might as well
be wearing a dress, everything was that obvious.
I returned to the kitchen and kissed Tony good-bye as he left
for work. Mother told him as he was going out the door that he
was welcome to return anytime and gave him our phone number. I
was shocked when he asked if I would go on a date with him on
the coming Friday night. He said he would take me to a dinner
and a movie and then we would go back to his place for some sex
and I could spend the night there if I wanted and my mother
approved. Mother told me she had no objections, and said the
choice was mine to make. I hesitated and told him to call me
during the week for my decision. There was a part of me that
wanted to say yes, but I knew that could get me into deeper
trouble with mother and I wasn't sure how I would feel after
thinking about things for a day or two. A discussion with
mother when I got home from school would also affect my answer.
He was satisfied with waiting and promised to call me every day.
He said how much he had enjoyed my company and the sex we had
and was interested in me only as a girl, but that he wanted to
spend as much time with me as he could. I thanked him and told
him how much I had enjoyed his company and being able to talk to
him so easily. I also told him how arrogant I thought he was
when we were first introduced, but that after getting to know
him better, I could see that was just an act he used in public
and that inwardly he was a really great person. I couldn't
believe I found myself saying these things and expressing a
desire to be with him openly. I said good-bye with a kiss and
then he drove off and I went to school with Michelle and Kenny.
My fears were realized as we approached the entrance to the
school. The captain of the football team was waiting for us
with a few of his friends and a couple of the cheerleaders.
"I'm surprised you had the guts to show up this morning sissy!
I thought you would try to take a few days off after the other
day. even in boys clothes you look more like a girl with your
long hair and small body. We took a vote after you left the
other day and decided that since you obviously prefer to be a
girl, you should come to school as one, and we have elected you
as a member of the cheerleading squad. Practices are held every
day after school in the girl's gym. These girls have agreed to
help you dress since you didn't come dressed on your own. Your
sister can help them also if she would like. To be sure that
you continue to dress as a girl and show up for cheerleading
practice, one of us is going to accompany you. Today it is my
turn to be your escort. As payment for my protection during the
day, you will be required to blow me later. You will be given a
cheerleader's uniform following practice. You must keep the
uniform clean and wear it to all our games. You will also
perform with the other cheerleaders and ride the bus with us to
our away games. During those bus rides your mouth will be at
our disposal just like the other girls do. We are not going to
let you out of this, so get used to being a girl and a slut.
Don't worry about what the teachers are going to say, we will
clear it with them and show you just how much clout we really
have around here."
They walked us into the school and stood outside as the girls
took me into the girls' bathroom. My sister came in with them
and asked what they were going to do to me. They told us that
they had brought some extra clothes that they thought would fit
me and were going to do as the boys had asked them to dress me
as a girl complete from the skin out and including makeup and
jewelry. They were told to make me look like one of the sexiest
girls in school and to deliver any male clothing to the boys for
them to destroy on me. Michelle told them to dress me for
today, but she would save them the trouble the rest of the week
by dressing me at home. I was stripped and they had a good
laugh when they saw the breast forms I was being forced to wear.
They laughed as Michelle explained how mother was punishing me
and joked about being able to save their tissues. It also
turned out that one of the girls was a hospital volunteer and
said she would put in a word for us. They dressed me in red
lace bra and panties, a pair of pantyhose, a red minidress, red
heels and gave me a red purse to carry. My fingernails were
painted a bright red to match the lipstick they had used. My
hair was pulled back into a ponytail and tied with a big red
bow. They added a dab of perfume and then took me out to the
boys. They told the boys what my sister had told them and how
she had promised to make sure I dressed at home every day from
this day on. This delighted them greatly. It was now time to go
to class. The football captain escorted me and even explained
to the teacher why I was dressed as a girl and that they were
going to keep me as one. The teacher instead of arguing with
them, commended them for their actions. I knew I was in real
trouble at this point. He asked what female name I go by and
immediately crossed off Richard and wrote Jennifer on the
attendance sheet.
In each class the story was basically the same. Not one
teacher argued about my treatment, or even hesitated from using
the name Jennifer to call on me. My fate was sealed and I
wondered how mother was going to react to the news. I also had
to wonder what I was going to have to do as a cheerleader. I
could not picture myself in a skirt and sweater waving pom poms
all about and saying stuff like, "Peter! Peter! He's our man..."
I knew that as much as I dreaded it I was going to have to do
it. After school, I was escorted to the girls' locker room
where I was met by the girls that had dressed me up that
morning. They led me inside and introduced me to the girls' gym
teacher. They told her the complete story of my transformation
and how I was there to be a cheerleader and would be a girl in
school from then on. She laughed and said that it was a fitting
punishment and reminded me that I would even have to take my gym
classes with the girls in the future. I was issued a gym
uniform to practice in and a cheerleader's uniform to wear at
the games. Michelle had also decided to become a cheerleader
and was welcomed to the squad as well. We practiced the entire
repertoire of cheers and went over several dance sequences to be
used at halftime. I was surprised at how easily I learned the
routines. I thought it would be much more awkward than it
turned out. It even seemed like fun to me. Following practice,
I was walked home by the football captain. He invited himself
into the house and demanded that I give him a blow job as
dictated that morning.
I dropped to my knees in the living room with my sister
looking on and went straight to work on him. He climaxed
quickly and went on his way reminding my sister and I that I was
to come to school as a girl from then on. I was a whore and I
knew it and had somehow slipped into a mindset where it seemed a
natural part of me. I can't explain why or how, but I knew it
was true and I wanted to be a girl in every way. I had to tell
someone and my sister was willing to listen. We talked clear
through to the time mother arrived home. Michelle helped me
explain what I was going through to her and we continued the
conversation about me getting the operation and remaining as a
girl forever. Mother was crying since she knew she was losing
her son, but she was willing to help me go through with it. She
said we could consult the gynecologist when we got to our
appointment. She also said it would have no effect on her
punishment and we would still have to do volunteer work. She
did say that having me go to school as a girl would make things
a bit easier as I would live full time as a girl and get to know
if I really wanted that life. I finished my senior year as a
female and had my penis removed that summer. I received breast
implants the week after my first visit to mother's gynecologist.
she had suggested a plastic surgeon who was very willing to do
it for me and also did the penis removal and vaginal
construction. The usual psychological testing was waved under
the circumstances and they never really asked questions. It is
amazing what can be done if one has the money to do it. All my
records including my birth certificate and driver's license were
changed to reflect my gender change. I still enjoy being sexual
active and now having three holes which each give me pleasure
when penetrated by a cock. I make quite a bit of money each
night as I have followed the course mother set me on in the
oldest profession in the world. I wouldn't change a thing as I
am very happy as a female and a prostitute.
THE END
(A fictional work by "Jennifer Lynn Daniels")