Prom Princess
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A Prom Princess
By Sammy
I had never been that masculine a guy in the way acted and the way I
looked, but had never wanted to look like a girl. None-the-less here I
was driving to my friend Stacy's house to be transformed into a girl. I
had no one but myself to blame since I'm the one that accepted the bet
with Roy and I hadn't been totally clear of the details at the time.
Roy's bet was that I wouldn't be able to find my own date for the prom
and when I didn't, as he put it, find one within a week of the prom then
he would find one for me. At first I said no, I wouldn't be apart of
something like that. Then Roy said the only reason that I wouldn't, was
because the only girl that I could possibly get to go with me was Stacy.
I tried to ignore him, but he just kept at me and taunted me into going
along with him bet.
So I reluctantly agreed, even knowing at the time that I would surely
regret it in the end. All that Roy said was that I had to go with
whomever he picked no question asked and I was to go along with
everything that was need to make the evening work. Looking back, an
alarm should have gone up right there, it should have been obvious that
Roy was up too no good. He always seemed to have nothing better to do
then to torment me even in our early school days. I shouldn't have
agreed without all the details of what was needed.
So here I was ringing my best friend's doorbell getting ready to be
transformed into a girl. I was going to be the date of my childhood
bully at my senior prom. The Only reason that Stacy was involved at all
was that she was my best friend and the only one I trusted to help me
with this. The fact that she was a wiz at cutting hair and applying
make-up made it all the better.
The door flew open. "Come on in," said Stacy as she pulled me in, "you
are late. We have got a lot to do. Take this into the bathroom and put
it all over your body, except your crotch," she handed me a bottle of
depilatory cream and pink satin panties. "When in the shower use the
shampoo and the body-wash that are in there. After you are done with
that, shave your face and put on the panties. Then gather up all your
things and come to my room."
So I went to the bathroom, removed at my clothes and started smearing
the smelly cream all over my body. I wondered why I would have to go to
these measures, but just followed the direction. Roy had given Stacy a
detail list of all that was to be done to me, if anything was found not
be just right the deal was off. He had assured me that the remainder of
the school year would be hell if that were to happen. So it seemed I
would have to do everything he asked.
After waiting ten minutes I showered off the cream and with it what
little hair I had on my body. Then I took my long hair out of the
ponytail it was in and I used the shampoo then the body-wash which made
smell very feminine.
After toweling dry I proceeded to the sink to shave the fuzz I called a
beard. Then I looked at the pink panties on the counter. I was going
to have to wear them all night long and there was much more to come. So
I just picked them up quickly to get it over with, placing one leg in
then the other. The feeling of them against my bare legs had unexpected
results as I now had an erection from this simple action.
I tried to tuck my penis between my legs as best I could, but it was not
easy in those panties with it fully erect. I looked in the mirror to
find it bulged out a bit and couldn't figure out what to do. Luckily,
it went a little limp after a minute or so which allowed me to once
again try tucking it away. It was good enough this time.
So I picked up my clothes and went to Stacy's room. It felt so weird to
walk the hall of her house like this even though her parents weren't
going to be back until the next night. The thought of them coming home
and finding me like this was terrifying yet strangely exciting at the
same time. My little friend came back to life again as I entered
Stacy's room.
"You look to be enjoying this a little to much there," she said smiling.
"This is not funny and it isn't enjoyable."
"Okay come here." She then glued on a pair of large silicon breast
forms to my chest and then had me hold them in place as she got the bra.
The soft feeling of them in my hand didn't help my erection one bit.
"You can let go now." As I did, I could feel a pull on my chest, which
felt very strange.
"How big are these?" I asked as she placed a strapless bra over them?
"You are now a C cup."
"Why this big?" I looked down to see that they look real in the bra.
"If I were you, I would be happy he didn't go bigger. Okay sit." She
was now standing behind a chair with a cape in her hands. As I sat
down, she placed the cape around my neck so as she could now cut and
style my hair. The night before, she had dyed my hair a very light
blonde and tomorrow it was back to brown. Since my parents were away for
three days, they would never know about it.
After cutting my hair she combed it out and blow-dyed it straight. She
then left it all down except for the front which she pulled back
securing it in the back with a flower-covered hair clip. She then took
off the cape and had me stand back up.
It was now time for a garter belt and stockings. She placed the garter
belt on and placed the garters down though panties. Then she pulled
each stocking up my leg attaching them to the garters. I found the
feeling of the stockings running up my legs even better then the
panties. My penis was once again was fully erect and now just the
feeling of the stocking on my legs didn't help it go away.
As Stacy had me go across the room, to put on the three inch heels I was
to wear, I look at myself in the mirror on the back of her closet door.
I was shocked to see myself dressed all in pink lingerie and that all I
could see was a beautiful eighteen year old girl. I wondered how could
I look so passable when we weren't even done.
"Come on prom princess," Stacy said. "We've got to finish you."
"What have I got myself into?"
"You can still back out," she said as I sat back down. She started to
apply long artificial nails to my figures.
"This is my best chance, because if I back out Roy will make my life a
living-hell."
"Well then look at it like this, you can use this to learn a little bit
about girls. Just relax and try to enjoy it since you're going to be
dressed like this for the whole night. It will go faster that way."
I looked down to see that Stacy had given me a French manicure which
excited me even more since my hands now looked perfectly feminine. As
she started my make-up, I got lost in my thoughts. Maybe she was right
if tried to enjoy myself the night would probably go faster. Roy was
only doing this to humiliate me and if I acted as if I didn't care he
wouldn't get his satisfaction.
"Tim," Stacy said, "wake up cutie."
"Okay what's next."
"Just the dress."
She pulled it out of the closet and I should have guessed, was so very
pretty and pink. Stacy held it low to the ground as I placed my feet in
it. She then pulled it up closing the back which made me feel a little
closed in. The top looked like a corset and was tightly pressing on the
breast forms making what little flesh on my chest press up to form
cleavage. I looked down to see that I had great cleavage for really
being a boy. The bottom was long and flowing, coming nearly to the
floor. As one last detail she sprayed several squirts of perfume into
the air then had me walk immediately though. Then she sprayed more on
my waists, neck and chest which now made me smell completely feminine.
"Is all this perfume really necessary?" I asked.
"It is what Roy asked for."
"Well then I guess I'll have to do it."
"Okay, here is your purse," she said at she pushed me to the door. "I
put some lipstick, powder, and your keys in there. You will also find a
note from Roy in there with more instructions. Now get out so I can get
ready."
I stood there in the hallway wearing a pink prom dress and holding a
purse with the hardest dick possible. Why was this turning me on so
much? I want a date that looked like this, not too looked this way
myself. Something had to be done about my penis if I was to make it
though this. So even though I really didn't want to dress like this, I
went to the bathroom to masturbate.
I looked into the mirror and found my makeup was flawless with pink eye
shadow, pink lips, a little blush, eyeliner and mascara. It was
gorgeous even though I hardly looked made up. I was looking at a dream
girl and wondering how could I look so perfect as a girl.
I got started by pulling up my dress and pulled down my panties. I
found that as I stroked myself with long nails on my figure tips it made
the whole thing feel better. I had never satisfied myself so fast in my
life, but it did the trick and my penis was limp in seconds. I then
cleaned up and pulled my panties back up, tucking my package away.
I then went to the living room and went over all the stuff I practiced
over the last week with Stacy. Like how to walk, sit, talk and anything
else in between that would help make me appear to be female this
evening. I was lucky that my voice never changed that much and making
it sound like a girl was easy. Now that I had seen the way I looked
though, I wasn't so worried about being found out.
After going over everything in my mind I took out Roy's note:
Dear Tabitha,
That is what I will be calling you tonight. Remember it
is your choice to do this tonight and you will do
everything that is asked of you. If I'm satisfied with
your job, you will have nothing to worry about. If not,
you will regret it.
Yours truly, Roy
Just then Stacy came out in her gown. She was just as beautiful as I
was as she twilled around for me to see. "How do I look?"
"Gorgeous," I said as Tabitha and twill around myself, "and me?"
"You are going to turn heads."
"I don't think that will happen."
"Trust me. The boys will lust over you and the girls will be jealous of
you."
"Do you really think?" I said very nervously.
"Oh yea, but just have fun with it. Tomorrow you will be back to normal
no harm done. Besides you will now know what it is like to have men
looking at you with lust filled eyes, like you do all the time."
If I didn't have makeup on, I'm sure that Stacy would see me go beet-
red. "I never thought it was that bad until you explain it like that."
"Oh, it's not all bad. It feels nice sometimes, but it can be creepy
also." She could see I was nervous so held out her arms to give me a
hug. "Come here," as she gave me a hug. Just then the doorbell rang
and it had to be Roy. My night of torture was just about to start.
Stacy let Roy in and I could see he was dress in a very smart tux. He
would have been any girl's dream date the way he looked, just not my
choice. He had in his hands a pink corsage which he moved forward to
handed me. I turn Tabitha on getting into the role that I would be
playing for the night. I took the corsage and then, standing on my
tippytoe's, I gave him a kiss on the cheek.
"How sweet," I said, "thank you Roy."
I could tell that Roy was a bit taken back by my preferments. I felt I
had turned the tides a little, but he still had the upper hand.
"Shall we go," he said as he held out his arm for me to take hold of?
Without hesitation I took hold just like any girl would as Roy escorted
outside to a limo. He was really playing the perfect gentleman as I
walked on his arm to the car. Once there the driver opened the door for
us as Roy helped me in.
I got in, slid over on the seat then Roy got in next to me. The driver
got in and it only took Roy a few minutes to make me feel uncomfortable
by putting his arm around my shoulders. In response I leaned toward him
and rested my head on his chest as I trying to think if there was
anything else I could do in my role.
So I moved my left hand to his knee and then that was when I notice that
Roy's penis was pressing again his pants. How could he be aroused by
the way I looked, I wasn't really a girl and he knew it? This couldn't
be happening, he was just attracted to idea of me as a girl, that was
what I told myself. He wanted Tabitha and she didn't exist, you aren't
her.
Then Roy sat up and turned toward me. He pushed me back into the seat,
leaning over me, then leaned in closer and kissed me. At first I fought
a little, but I just let go for my own good. If I fought, he would be
anger and in the end I would pay and since it was just a kiss there
would be no harm.
Roy's tongue entered my mouth and I let Tabitha take over, probed my
tongue into his mouth. I could feel his hands explore my body as we
made out, so I placed my hand on his back and lost my self in the
moment. Roy was in control and I strangely found this exciting and
horrible at the same time. Every time I had made out with a girl it was
me who seemed to be in control and just sitting there with Roy in
control of me was strangely arousing. It was also scaring me that I was
letting go so much, almost enjoying it.
As we pulled up to the prom, Roy sat back in the seat. I sat there in a
daze for a minute. Then I thought to my self what if my makeup was
messed up. I pulled out the compact that Stacy had put in there and
looked to see if I looked all right. I didn't want to look like a mess,
but I looked fine.
As the driver opened the door, Roy got out then held out his hand for
me. He helped me out and offer his arm again so he could escort me in.
Then I started notice that Stacey was right about the guys, as they did
look at me. I was pleased at first, but when I though about it beyond
the fog of Tabitha it just crept me out, I'm a guy.
Then I noticed that some girls looked at me with a look of 'you bitch'.
They were mostly girls whose guys looked my way to long, but a few just
looked to be simply jealous of my looks. I soon felt that too many
people were looking at me.
After we ate, I asked Roy to dance. I then asked again and again
figuring he wouldn't want to do it, since I knew I didn't. Whenever we
slow danced, I would place my head on his chest, which was easy since I
was about five inches short then him even in the heels. His hands would
tend to migrate to my ass as we danced and I would move it back up every
time.
When Roy left me for a little bit of time that night, I needed to use
the bathroom. Without thinking I walked into the men's room and when I
enter there was no one in there. Still not think I went straight up to
the urinal, but when I tried to undo my pants and found none, I looked
down and all I could see was my cleavage. Everything came back.
"Shit, I'm in the wrong bathroom."
I turn and went for the door just as a guy came in. He looked straight
at me as I went for the door, but blocked the way as he tried to put his
arms around me.
"If you were looking for a man," he said to me as he tried to kiss me on
the neck, "you didn't have to come in here. No one would ever turn you
down."
Trying to get away, "I am sorry I came in the wrong door."
"You have nothing to be sorry about, baby." He was getting more
aggressive as he gave me a squeeze on the ass.
"Leave me alone," I said trying to get out of his grip.
"Just calm down and it will all be over soon." Then with little thought
I kneed him in the crotch as hard as I could. He went down onto the
floor and I cringed as I thought of the pain he was in now. I
immediately existed and went to the woman's bathroom, getting in and out
as quick as possible.
I went to find Roy and asked him if we could leave, so he escorted me
out and down the street. I walked for a few minutes on Roy's arm until
we came to a motel. He lead me in, but for the first time I hesitated
as I thought what is he up to now.
"It is just for appearances," he whispered to me. "Just a few hours in
the room and them I take you back to Stacy's house." With that I
relaxed and went along.
As we made it to our room, I saw many couples from the prom in the hall.
It was the most awkward I felt all night, but I got through it by
telling myself that I had nothing to worry about since no one knew it
was me. It would be over in a few hours and all behind me.
We got to the room and I sat on the bed. Roy shut the door, but didn't
lock it. Watching him walk around the bed and started to take his
clothes off. This was now getting really strange.
"What are you doing?" I said for the first time that night in a male
voice. I immediately got up and moved away from the bed, back against
the wall. Roy was totally naked and had a raging hard-on.
"Well you see I had planned on it being just the two of us, but since
you looked to be enjoying yourself as a girl as much, I figure I would
complete your night with a bang. When I left you at the prom for ten
minute you see, I was arraigning for some eager gentlemen to join us.
They know you are a guy pretending to be a girl. I told them you were
eager to be pleasured by men. Now you will be a good little girl and
take your medicine."
"You can't be serious. This was not part of the agreement."
"Oh, it was though. You see you agreed to do what I asked tonight. I
will do as I said, if you finish out the night with me and be the girl
you seem so willing to be. If you talk back to me again, the deal is off
and I will tell everyone that you tricked me into believing you were a
girl and got me to take you to the prom. If Tabitha comes back, I will
never tell a soul. If not there is the door you are free to walk home
and think about how the rest of the year will be if I tell."
He had me I knew he would do it if I didn't go along. If I did he still
might, but I felt it was my only choice. So I mustered up everything I
had and put on my best girl act. I ran over to Roy placed my arms
around his neck and looked into his eyes as I could feel his hard cock
press up against me.
"I'm so sorry," I said softly in Tabitha's voice, "you know that all I
want is for you to be happy. So what do you want me to do."
"Much better. You stay in character until I drop you off and you will
be safe." He went and lay on the bed. "Well for starter you need to
take off that dress, let me see if you wore everything you were suppose
to."
"I am sure you will be pleased." This couldn't be happening. I reached
behind myself to undo the dress and then I slowly pull it down taking
one leg out then the other.
"You look just as beautiful out of that dress. Now come over here." He
patted the bed next to him. I walked over to the bed and kneeled on the
bed. Then I figured I should make it good and I leaned over Roy with
one hand on his chest and the other on the bed next to him. I raked my
long figure nails though his chest hair which seemed to make him more
aroused.
With little thought I leaned in and kissed him. I felt his tongue enter
my mouth as mind entered his, which lasted a few minutes as we make out.
I just told myself again that it was Tabitha that was doing this and
you're not in control. I couldn't keep it up if I didn't tell myself
this.
"Well," Roy said to me as we finished. I knew what he was pointing to
with his eyes. He wanted me to suck his dick, so with one more kiss, my
mouth and hands slowly made their way down his body. I thought about
what I would like a girl to do to me and tried to disconnect myself from
the room. Tabitha was in control.
After about a minute or so of delaying I was there on my hand and knees
between Roy's legs. I wrapped my right hand around the base of his cock
and just placed my mouth over his rod. My head was bobbing up and down
as I stuck on it with what seemed like a ravenous appetite. I just
wanted this over with.
"You're a great cock-sucking bitch," he said will a moan.
I just ignored the comment since Tabitha was the one in control, not me.
It will be over soon, but then the door opened and I remembered that he
had other guys coming. This was going to become worst.
"Roy you weren't kidding when you said she was willing to go," the first
guy said as he came in.
"Yes she is just get...," then came what seemed like an explosion of cum
in my mouth, "...ting started."
I tried to keep from gagging as I swallowed the salty goo. I turned to
see nine eager guys standing at the foot of the bed, all trying too
quickly undressing.
"Well want are you boys waiting for," I said seductively as Tabitha. I
just kept the act going as I wanted it over with as quick as possible.
"Who's next, I'm getting bored?" And in seconds Roy moved to be
replaced by another guy replaced him.
As I got started on the next guy, I got my next surprise. Someone pulled
down my panties and then grabbed my ass cheeks spreading them apart. I
trying to brace for what I knew was coming, but didn't have time. I
felt a searing pain in my ass, it was one of the most horrible things I
had ever felt. I felt like I was being impaled by a baseball bat. I
trying to put the pain out of my mind and concentrate on the cock in
front of me. Another load in my mouth and shortly after the first in my
ass.
Went one guy was done another took his place. I found the second cock
in my ass was not as bad. I was surprised to find it started to become
a little pleasurable. This turn out to be my last blow job though, which
my stomach was glad of since I felt sick. I could even swallow what was
in my mouth so it ended up oozing down my chine.
Though I was done sucking-cock, the guys took turns ramming my ass.
After several times I could feel cum running down my legs. I was
starting to find the feeling of my ass being stuffed quite enjoyable.
What was happening to me? I was moaning with pleasure and rolling my
hips into the guys' thrusts. I was intoxicated with pleasure. I was
immersing my self fully into Tabitha.
I had lost all track of time and how many times I had been fucked. I
was sure that more guys came in and I was getting tired. Slowly one by
one they left to leave only Roy screwing me with all he had. I was
still moaning only half aware of what I was doing, totally lost in
pleasure. As Roy came for the last time and pulled out, I just waited
for the next dick. After a few seconds with no more cock to coming I
collapsed forward on the bed.
"Well that was great," Roy said as he was dressing. "You are a fine
piece of ass. Once you get cleaned up, I'll take you back to Stacy's."
"What time is it?" I said still as Tabitha.
"You didn't seem to be worry about time when you were moaning with
pleasant and yelling for more. I never thought you had it in you to go
to the prom with me, let alone take that much dick. You should be
ashamed to call your self a man. You're just a blonde prom slut." I
wanted to yell and scream at him for doing that to me, but I wanted this
over more. Roy was buttoning up his shirt, "I'll be in my car out
front, don't take long."
I looked at the clock on the table beside the bed. It had lasted for
almost an hour and a half. I was so humiliated, how could I do that?
More importantly how could I enjoy it and get into it? I asked for more
and more, then when it was over for a few seconds I wanted even more. I
was disgusted.
The insides of my legs were dipping in cum. As I got up, I felt more
run out my ass. I looked at the mess I had never seen this much cum
ever. I went to the bathroom and filled the tub. I took off the now
drenched panties and stockings. What was I to wear now? Then to my
surprise there were new panties and stockings on the counter.
Roy thought of everything, So I got in the tub and clean my bottom half.
After toweling off and placing the new panties and stocking on I went to
the mirror. I cleaned the dried cum off my chine and fixed my make-up.
I then retrieved my dress from the room, put it back on and headed out
the door. I looked back and though what a mess.
As I came out of the motel Roy came around and opened the door for me.
He helped me in and shut the door. Still acting the gentleman, but why.
Neither one of us said a thing the whole way to Stacy's house. I felt
humiliated and felt used knowing that this night would leave me changed
for life. I looked back at the night and wondered how I could have
acted the way I did.
When we got to Stacy's house, I found that her parents were home which
meant that I would have to go home like this. As I moved to get out of
the car, Roy grabbed my shoulder. I turned to receive a kiss from Roy.
I was totally surprised and I found this kiss to be enjoyable unlike the
earlier two. I looked at Roy for a second.
"I started out this evening to humiliate you," Roy said, "and was more
determined after the way you acted. When we kiss earlier and then you
pleasured me I felt something for you." No way Roy was attracted to
Tabitha. "I now wish I had not asked those guys to come. I am sorry to
have put you through that, but I really wish that I could get to know
you better Tabitha."
"Tabitha doesn't exist," I was Tim again. I no long care if he was
angry and used this night against me. "It was all an act. You
succeeded in humiliating me. You used me and degraded me. I don't
really care if you are sorry or if you tell everyone about tonight."
I got out of his car and walked to my car which was parked a little way
down from Stacy's house. I opened my purse, took out my keys and got
into my car. I immediately started to cry as Roy's car went by. Stacy
told me that I could learn something from this, but little did she know
what. I had never felt so weak and vulnerable as I wondered how anyone
could treat someone like that.
After a few minutes of crying I was ready to go home, but when I got
there I had another problem. My parents where home a day early and I
only had the cloths I was wearing, how could I go in like this. There
were only lights on in their living room so they were still up. So I
drove around for a while hoping they would go to bed.
About an hour later I pull up in the drive way as the house was now
dark. I got out of my car as quietly as I could and walked for the
front door. I hurried up the stairs and to my room as fast as I could.
I hoped I wouldn't wake my parents as I shut the door. I just curled up
on my bed and cried my self to sleep not removing anything.
Aftermath
Luckily I woke up before my parents that morning and got out of
everything except the bra. I couldn't remove the breast or the nails
and I would need Stacy help. So I called her and luckily her parents
would be going for a little bit today. That meant that I could go over
there before they return.
When I returned to school on Monday, things seemed to be normal. I had
not had time to have my hair dyed back to brown or cut. A few people
said me why I had gone blonde, but most didn't say anything. The hair
cut went pretty much unnoticed as I usually pulled my hair back in a
ponytail. Stacy said she would dye it brown again as soon as she could,
but I really didn't want to. High school would be soon over and I would
be off to college in a few months, so it didn't matter.
Nothing was said after that and I tried to get back to normal. Roy
never told anyone as far as I know and he didn't say anything to me the
rest of the year. I would see him now and then, but he barely even
looked at me.
I was at graduation and figure that I would never hear for Roy again.
But after the ceremony, he came up to me with a large envelope. He just
handed it to me and said nothing, then walked off.
Later at home I opened the envelope and took out a letter.
Dear Tabitha,
Here is the picture of us at the prom and a video tape
of us in the motel room. I promise you these are the
only copies and there is nothing else from that night.
I am sorry for everything I did to you and if I could
I would take it all back. I am sure you could never
forgive me and that I now know that I can never
forgive myself. I know that nothing can give you your
dignity back, but if there is ever anything you need
from me just get in touch. You probably don't want to
hear this, but I can't stop thinking of you. I will
always see you as Tabitha. I hope you have a good
life after this and this is not something that scars
you for the future.
Sincerely, Roy
End
Dottie
- 13.12.2021
- 9
- 0
