VIOLA'S DEAL ? by: Curtis Lemmon
Part One: The Crisis
I was desperate.
It wasn't easy, being the man of the house at age 18. When Dad died so
unexpectedly, Mom should have been the one to straighten everything
out. But she was such a pampered butterfly - the privileged daughter of
a rich man and the privileged wife of an even richer man - that she
couldn't even recognize, much less cope with the disaster which had
befallen our family. Don't get me wrong -- I love her and she's always
been a sweet, nurturing mother... just one unable to face unpleasant
situations.
I only learned of the problem by chance, going through Dad's papers a
couple of weeks after the funeral. I found the loan applications and
the business statements that showed what a terrible businessman my
father had been. Oh, it was bad enough that he had run the family's
100-year-old financial management firm into the ground... but he had
also put up Mom's trust fund, my trust fund, Martha and Danny's trust
funds, what was left of the company, our family estate and all our
personal property (including Mom's family jewels) as collateral for
secondary loans to service his primary debt.
And, I learned, it was all in default. I found a notice from a Samuel
Hamilton, director of Hamilton and Associates, Ltd. that he would begin
foreclosure proceedings in... well, the date turned out to be two days
before Dad's funeral, unless the debt was paid in full. I went to Mom
and tried to discuss the problem, but she just couldn't comprehend what
was happening. I didn't tell Martha, my 16-year-old sister, or Danny,
my 14-year-old brother, because I didn't want to worry them.
I didn't know whom to turn to. Grandpa Hill (my mother's father) was
the rock we all leaned on in the family until his death three years
earlier. Stephen Parker, my father's partner and best friend, committed
suicide less than six months ago. Now I knew why.
Who would help me?
I finally realized I would have to help myself.
Let me tell you about myself. I've always been a pretty smart guy. I
graduated third at my class in Andover Prep and was waiting to enter
Harvard as a freshman in a little over a month.
My intelligence helped me survive growing up as an undersized, feminine
-looking 'pretty boy'. I could have endured some tough times in prep
school, but I was smart enough to protect myself, usually by developing
a friendship with one of the older, more popular, more athletic boys.
I'd help him with his studies and he'd befriend me, providing
protection in the shark's nest that an all-boy's prep school really is.
I decided to use my intelligence now, spending a week investigating
this Mr. Hamilton before setting up an appointment to meet with him.
What I learned didn't encourage me. He was one of the business world's
hot young stars, a multi-millionaire before he was 30. He was known as
a ruthless, heartless loner, who made his fortune by absorbing small
less stable, less-well-run financial institutions (such as my Dad's). I
picked up a few tidbits of gossip that I thought might or might not
help me, then made preparations for an appeal of last resort.
I figured I was as ready as I could be that August morning when I rode
the elevator up to his office suite on the 49th floor. His secretary, a
charming middle-aged woman of about my Mom's age, was very nice to me
before showing me in to Mr. Hamilton's office. I walked in confidently,
carrying my little briefcase at my side.
I had seen pictures of him in the financial magazines I had studied. I
knew what to expect - he was about medium height, a trifle overweight
and just starting to loose his hair. But I was surprised by his
friendly smile and his graciousness as he greeted me and ushered me,
not to the chair across from his desk, but to the comfortable sofa that
afforded a magnificent view of Boston from a floor-length picture
window.
He plopped down at the other end of the couch, like an old friend.
"Matt, can I call you Matt? I'm so sorry about you father," he said.
I didn't believe his sincerity and almost sneered at him, but I
couldn't see where that would help me, so I thanked him and asked about
the foreclosure notice.
"Oh, that," he said, looking a trifle sheepish. "I'm not a monster,
Matt. I knew you and your family were grieving. I couldn't hit you with
that so soon after your father's death."
I asked him when he was planning to hit us with it?
"I don't know," he shrugged. "I guess now is as good a time to settle
this as ever."
He explained that the debt, with interest, had now topped $8 million.
"Even if I foreclose, I won't reap half that," he said. "I'd love to
work something out with you."
I told him there was simply no way I could come up with the money to
make a substantial payment on the loan. I offered a counter proposal.
"Look... I'm going to become a lawyer," I said, modestly detailing my
academic record. "Eventually, I'm going to be making a fortune. What if
I sign over a substantial portion of my future earnings... say 25
percent, in return for not foreclosing on the debt, I can almost
guarantee you'll get more than $4 million out of the deal."
He smiled.
"I'm sure I would," he said. "But you're talking four years of college
and three years of law school... not to mention several years as an
associate, making peanuts before you start to make the big money. Let's
be generous and suggest you start to bring in serious money 10 years
from now. Do you know what the interest on your principal would add up
to in 10 years?"
He hopped up and walked to his desk. He pounded out some numbers on an
old-fashioned calculator, then tore off the printout and showed it to
me.
I swallowed.
"Mr. Hamilton, there's got to be something I can do," I said, fighting
back the tears. "I mean, I'm young... I'll find a way to survive, but
this will kill my Mom. And Martha and Danny. They're too young. I just
don't know what they'd do."
I turned away so he wouldn't see my tears. While I got control of
myself, he was thoughtfully turned away himself, standing by the
window, looking out. I cleared my throat and he turned around.
"Matt, I'm sorry," he said. "I honestly feel for you and your family,
but I don't know what I can do. I have a responsibility to my
investors. I can assure you they won't allow me to write off a debt of
this size. I mean, personally, if there's any way I can help you or
your family out..."
"I don't want your charity," I spat out.
He shrugged and turned back to look out the window.
I had another card to play. I hated to play it, but I was desperate.
"Mr. Hamilton?" I said, stuttering in my disgust at what I was about to
do.
"What is it Matt?" he asked, turning back to face me.
"It's just that I heard some rumors about you."
"Oh?" he smiled and his eyebrows went up.
"I heard you might prefer boys to girls," I said.
He looked amused.
"If this is an attempt to blackmail me, let me say that secret isn't
worth $8 million," he said. "I'm single, of age, I've never done
anything illegal and my investors don't give a damn about my sexual
proclivities."
"No, I'm not talking about blackmail," I said.
"Then what?"
"It's just that... well, when I was in school... there were a lot of
guys who wanted to... I mean, they tell me I'm a pretty boy," I finally
managed to stammer.
He laughed and shook his head.
"Am I to understand you are offering yourself to me as payment of
you're father's debt?"
Hearing it out loud like that made me blush. But I nodded.
"Well, to be honest with you, Matt, you are a very pretty boy," he
said. "But let me show you something..."
He went around his desk and punched up something on his computer. He
waved me over and I stood and walked to a spot where I could see the
screen.
I could tell he was on the Internet. What appeared were a series of
thumbnail pictures of young men in various stages of undress.
"Now, this is probably on the fringe of legality," he said. "Not enough
to get me in real trouble, still... the truth is, I just go here and
look. I'm never availed myself of the service."
He clicked on one picture of a boy who appeared to be about 16. The
thumbnail picture was replaced by a picture, that took up over half the
screen, beside it was a notation with the boy's name (Lawrence), his
age (19... yeah, right) and, oh my god, a list of prices, ranging from
$1,000 a night to $5,000 a week to $12,000 a month. He was, I had to
admit, younger looking and far prettier than me.
"While I appreciate your generous offer," Mr. Hamilton said. "As you
can see, I don't think you're worth $8 million on the open market."
I returned to the couch and picked up my briefcase. There was just one
option left. The only question was whether I had the courage to do it.
I reached into the briefcase and felt my fingers curl around the grip
of my father's .38 police special.
It took me two hands to hold it up and to pull back the hammer. When I
looked down the barrel at Mr. Hamilton, he wasn't smiling any more.
"You leave me no choice," I said. "I'd do anything..."
I thought he'd be afraid or contemptuous. Thinking back, if he had
laughed at me, I think I would have pulled the trigger.
Instead, he looked very sad.
"What will that accomplish, Matt?" he said in a soft voice. "You can
kill me, yes, but the debt will still be there and you will be a
murderer."
"I don't care..." I said, starting to cry.
"Think about your family," he said. "Your father just left them... how
will they feel when you go to prison for the rest of your life? Will
that help them?"
My hand wavered and my vision clouded as the tears came faster.
"I don't know what else to do," I whined, lowering the gun.
"Not that, Matt," he said. "Give me the gun, son."
For a fleeting instant, I thought about turning it on myself. Before I
could make up my mind, Mr. Hamilton was at my side. He gently, but
firmly took the gun away from me. He handed me a handkerchief, then
walked to his desk and locked the gun in one of his drawers. Then he
went to the little bar beside his desk and pour me a stiff drink - I
think it was brandy.
"Here, drink this," he said.
It burned when it went down my throat.
Then he turned away, staring out the window as I got control of myself.
I don't know how long that was... five or 10 minutes, maybe. All I know
is when I finished bawling, I laid his handkerchief on the coffee table
and took a deep breath.
"Mr. Hamilton, I'm sorry for that," I said. "If you want to call the
police, I understand."
He didn't respond. Instead, he stood there looking out the window.
Without turning around, he said. "There's no need for that."
I started to get up. There was nothing else I could do. But as I rose
he turned back toward me and gave me a strange look.
"Matt, you really love your family, don't you?" he asked.
I nodded.
"Before, you said you would do anything to help your family... did you
mean that?"
"I'd give my life, if it would help them out of this mess," I answered.
"Well, in that case..." he fumbled for the words. "There might be a
way."
Part Two: The Offer
Mr. Hamilton walked over to the bar and poured himself a stiff drink.
I sat back down on the couch, willing to listen to any proposal. He
walked back to the picture window and stared at the view, slowly
sipping his drink. I could see that he was trying to get things
straight in his head. Finally, he turned around and looked at me.
"Okay, here's the deal," he said. "I'm going to make you a proposal...
I want you to sit there and listen without saying a word. This is going
to be hard for me to get out, so I don't want to be interrupted. When I
finish, you can ask questions. Then I'm going to walk out of the office
and leave you alone for 10 minutes... again, I don't want you to say a
word. I'll walk back in and you give me your answer, yes, or no...
"If it's no, that's fine... you can leave and although I'd rather you
not tell anybody about the offer, I know I can't stop you, but..."
"Mr. Hamilton," I interrupted, "I'll listen to your offer. You don't
have to worry about me talking about it. I'll give you my word to keep
it quiet."
He smiled, but it was a nervous little smile.
"Great," he said. "Okay, here goes... again, let me get this out
without interruption."
Still thinking hard, he began to pace in front of where I was sitting
on the couch. He made two or three circuits before he started talking.
"Okay, here's the deal," he said, finally. "You were right... I am gay.
But I haven't had very much time to do anything about it. I've been too
busy making money, building my business to find... well, I've had a few
brief affairs. I've tried a few of the really expensive male
prostitutes ... it's not what I'm looking for."
He paused in his pacing and looked right at me.
"Matt, what I really want is love, the love of a very special, very
unusual person. I know you're not that person and I know you won't ever
love me, but at this point, I'm willing to settle for an illusion of
what I want. I think you can provide that illusion."
He let out a deep breath, then resumed pacing.
"Here's what you get - I'll still have to take over the company... my
investors will insist on that... but I can protect your family trust
funds and personal property. Your mother, your brother and your sister
can keep their home. I'll cover that part of the debt from my own
pocket. Furthermore, I'll pay your mother a stipend of $100,000 a year
over the length of this deal... we'll tell her it's a settlement on the
sale of your father's firm."
I wanted to ask what he meant by the length of the deal, but I
remembered his injunction about interrupting. Then he told me.
"You said you'd give your life... I'm not asking for that," he said. "I
want... let's see - in eight years, your younger brother will have
finished college. Your sister will be two years out of school and
probably married. They'll be in position to take care of your mother.
So let's say this deal is for eight years.
"That means you'll still be a young man - 26 years old - when it's
over."
I told myself I could live with that. I'd still have most of my life
left to live. Only... what was it he wanted me to do for those eight
years?
"I know what you're thinking," he said, smiling. "You want to know what
I want you to do for eight years, right? Okay, here's the part you
won't like."
He paused, as if expecting me to say something. But I was determined to
follow his instructions to the letter.
"I want you to become the person I've dreamed of," he said. "I'm not
talking about sex - although sex is involved. What I've always wanted
is this... a feminine-looking boy, who would be willing to dress and
act as a girl in public, yet would be a boy in my bed. More than that,
I want someone who loves that lifestyle and loves me and wants to be
with me and is passionate and happy and..."
He paused, shaking his head to clear the fantasy that was consuming
him. He turned to me with an embarrassed little smile.
"What I'd want is for you to pretend to be that person. Not pretend for
eight hours a day... but 24 hours a day, seven days a week - for eight
years. The change would be real. You'd have to announce to your family
and friends that you were gay and that we were lovers and that you were
going to adopt a feminine lifestyle. "
He paused to let that sink in.
"We might decide to make a few physical alterations - hormones or
breast implants that would make you look more feminine. Nothing
permanent and at the end of our agreement, I'll pay to restore your
male physique."
He nodded as if to himself.
"I think that's about it," he said. "Basically, you'd be agreeing to be
mine, body AND soul for a period of eight years. What you have to ask
yourself is whether you can submit, not only physically, but
emotionally... if you can act enthusiastic and loving about it all.
That's a big part of the deal. As I told you before, I can find
somebody to have sex with a lot cheaper than this... I want the love
and the affection too... or at least the illusion of it. Now... any
questions."
I was silent for a moment, almost overcome with conflicting emotions.
There was one thing I had to ask.
"You said I have to tell people that I'm gay and I'm doing this because
I want to?"
He nodded.
"That's important," he said. "Nobody will know of our deal, no secret
letters or private conversations, but let me ask you... do you think it
would make your family happy to know that you're submitting to me to
save their lifestyle?"
"They won't be happy to see me become a gay cross-dresser."
"Not at first... but if they think you're happy in your new life..."
He was right. If I could convince them I was doing this because I
wanted to, they would eventually accept me. If they thought I was
prostituting myself to save them, they would either reject the deal or
be miserable with guilt. No, he was right, it was better that they not
know.
"I haven't really thought this out, but obviously once our deal is
done, I couldn't prevent you from telling the world the truth," he
said. "I still think it would be better for everyone if you didn't...
maybe you could say you had decided you were not gay after all and I
seduced you or mesmerized you... whatever makes you comfortable."
I shrugged that was a detail we could get to at a future date - if I
accepted the deal in the first place.
I didn't see how I could do that.
Part Three: The Decision
Mr. Hamilton, as he promised, left the office to let me think about my
decision.
I stood up and walked to the picture window. Looking out at the
magnificent view of downtown Boston from the 49th floor, I wrestled
with my emotions.
You know what scared me?
It wasn't the horror of giving up eight years of my life. Hell, I was
ready to kill and die in the electric chair... I would have done it if
only that would have helped. I wasn't even afraid of doing all the
disgusting sexual things Mr. Hamilton would want me to do.
No, what I was really afraid of was that I'd like it too much.
God, how do I explain this? I guess I have been worried about my
sexuality as long as I can remember. Obviously, as a 'pretty boy'
growing up in a series of boarding schools, I had opportunities to
surrender to male-male sex. There were plenty of classmates (and more
than a few teachers) who would have liked to use me. I always resisted,
not because the idea of homosexual sex repulsed me, but because it
intrigued me. Don't get me wrong... I was attracted to girls. I think,
had this offer not come, I would have been able to stifle my homosexual
curiosity and live a perfectly normal heterosexual lifestyle.
The problem with Mr. Hamilton's offer was my fear that I wouldn't be
able to separate the act from the reality. God, I didn't want to end up
a sissy fag. But what if I couldn't resist the temptation? What if at
the end of eight years I couldn't go back to a normal lifestyle?
I stood there, looking out the window, trying to make up my mind. In
the end, I knew I didn't have a choice. Accepting his offer was the
only way out for my family. In a way, I was like so many society girls
in the old days, marrying money to help my impoverished, but
distinguished family survive.
Oh, well, I told myself... if I found that after eight years as a sissy
whore, I couldn't return to a normal lifestyle, I could always kill
myself then. My life was forfeit, whatever I decided. This way I could
save my family with my sacrifice.
I had made up my mind when Mr. Hamilton returned to his office. He
closed the door behind him then stood there, not saying anything.
"You win," I said. "I accept your offer. I promise you I'll do my best
to live up to it."
He shook his head. For a terrible (wonderful?) moment, I thought he had
changed his mind.
"No, that's not the way it works," he said. "You're not some uptight
virgin giving yourself to a man she hates to save her family. You're my
gay lover, joyously accepting my offer to come live with me. Now I'm
going to step out of the office again. I'll give you one more chance.
You have to remember the role you're going to have to play. Think about
it and if you want to accept, I expect you to jump into the role.
Understand?"
With that he opened the door and stepped out. I waited for him to
reopen it, trying to work out in my mind how he'd want me to play it.
Finally, after about a minute, I saw the handle turn.
Action!
As soon as he was in the office, I raced across the room and threw
myself in his arms. He enfolded me, sending a slight shiver up my
spine. I didn't have time to analyze it as I made myself kiss him on
the lips.
When I pulled my lips away, I forced myself to smile.
"Oh, darling... yes," I said. "Yes, I'll come live with you and try to
make you happy."
He smiled too and gave me another kiss. I felt his tongue pressing
through my lips, so I opened my mouth and let him have his way. He
broke the kiss and pulled his face away. He looked into my eyes.
"You're very sweet, Matt," he said. "Are you sure you want to adopt a
feminine lifestyle... to act the girl for me?"
I swallowed, but kept smiling.
"Oh, yes, Sam, my darling," I said. "I want to make you happy... I want
you to guide me and help me become the girl-boy you want me to be."
His arms pressed me toward him. I felt his hard dick pushing against my
mid-drift. Part of me was disgusted, but I have to admit, another part
of me was excited. In fact, I was a little disappointed when he stepped
back and looked at me.
"I'm glad you finally decided to come live with me, honey," he said. "I
know how afraid you've been to come out of the closet and how much you
dread telling your family. I tell you what, I'll go with you and hold
your hand while you tell them."
"Oh, Sam, I don't know...," I said.
His face clouded for an instant.
"Either you're ready to do this right or maybe it's not the right time
for us to live together," he said. "Which is it, Matt?"
I knew what he was saying.
"Okay, I'll tell them," I said in a faltering voice. "I'm sorry... it's
just so hard..."
He smiled then hugged me in his arms again.
"I know, darling," he said. "It's always hard to tell the people you
love that you're... different. But if they love you - and I know your
family does - they'll come to accept it. The important thing is to let
them see you're happy. That's what they want most of all."
I knew he was right. But I also knew that telling my family was going
to be tougher than taking Mr. Hamilton's dick up my ass.
Part Four: The Transformation
Sam (he insisted that from now on I call him that) quoted Shakespeare -
"If twere done, tis well that it be done quickly" - and suggested we
leave right away to tell my family.
I told him that quote was from MacBeth and comes from when he and his
wife were discussing the murder of Banquo. I was babbling to keep from
thinking about my situation.
"It's amazing how many people quote lines from Shakespeare, thinking it
proves something, when he put the lines in the mouths of fools or
knaves," I said as we entered the elevator. "Sorry... you're not
interested in hearing this."
Sam pushed the button for the first floor, then looked up at me and
gave me a nice smile.
"Yes, I am," he said. "I've always loved Shakespeare, but I never had
much time to read him or to attend performances. You sound like you
know what you're talking about."
I shrugged and maybe blushed a little bit.
"My senior thesis at Andover was on Shakespeare," I said. "There were
times when I thought I'd rather be an actor than a lawyer."
We had reached the ground floor. As the doors slid open, he said:
"Kill all the lawyers... right?"
We were walking together through the crowded lobby.
"Now that's a perfect example of what I was saying before," I told him.
"Shakespeare wrote those words for Wat Tyler, who in the context of the
play, is a monster. He's talking about how to deprive people of their
rights... clearly, the Bard disapproved of the idea. Yet, you hear
people say it all the time to trash lawyers."
Sam was looking at me in an odd way. His limousine was waiting in a no
parking zone just outside the front door. His chauffeur was holding the
rear door opened. Before we entered, Sam introduced me.
"Matt, this is Tommy Carroll... he takes care of me," Sam said. "Tommy,
this is Matt Brewster... he's somebody really special to me - he's
coming to live with us. Say hello."
I blinked a little - people at our level never talked to servants that
way. We never introduced people to them.
"Hey, Matt... I look forward to getting to know you," Tommy said,
holding out his hand.
I was in a little bit of a daze. I shook his hand and I think smiled,
then we were in the back seat and Tommy was pulling away from the curb.
"You were saying..." Sam prompted me. "... about Shakespeare?"
It took a while to get through my head that he really did want to talk
about the Bard. My head was spinning, but it was comforting in a way to
lecture him about the way people misuse his words. How Polonious
("Neither a borrower nor a lender be") was meant to be a fatuous
bore... about how the famous declaration "My fate is not determined by
the stars" was uttered by Edmund in King Lear, one of Shakespeare's
great villains.
I had just gotten started on the Authorship Controversy when Tommy
pulled up in front of our family estate. As we negotiated the narrow,
winding driveway that I knew so well, I lost my detached academic airs
and crashed back into reality.
Sam saw the panic rising.
"Matt, I know this is going to be hard for you," he said. "I'd expect
you to be nervous and fearful. But just remember, we love each other
and have decided to live together. If you convince them that we're in
love and this is what you want, they'll accept it... and I'll be right
beside you."
He smiled as if he really was my lover offering his loving support.
Mother greeted Sam graciously when I introduced them. She was beautiful
as always... still trim and attractive at age 39. Still, desirable, I
think. In fact, the fleeting thought crossed my mind that she and Sam
were better suited to be a couple - they were closer in age. Too bad he
lusted after me and not her.
"Mother, there's something we need to talk about," I told her, forcing
myself back to reality.
"Of course, dear, you know you can talk to me about anything," she
said. "I'm sure Mr. Hamilton won't mind if we..."
"He's involved, Mother," I interrupted. "He needs to be there."
"Very well, dear," she said. "Please, you and your guest get
comfortable in the sitting room. I'll have Marie serve tea there... or
would you prefer coffee, Mr. Hamilton?"
"Tea would be fine, ma'am," he said, sounding a touch nervous - like a
real lover? Was he getting in the act that quickly?
So we gathered in the sitting room, waiting while Marie served the tea
and retired. There was nothing else I could do to delay the inevitable.
"Mother, I have something important to tell you."
"You said that, dear," she said, smiling as she sipped her tea.
"Mother!" I snapped in exasperation.
"Stay calm, Matt... tell her," Sam said, reaching over to take my right
hand with his left.
Mother's eyebrows lifted in surprise. I let out a long breath.
"Mother, what I wanted to tell you was this... I am gay and Sam and I
are lovers and I have decided to move in with him and live with him and
be his... lover," I said, rushing the words out until that last fateful
word, which brought me to a stop.
My Mother didn't blink. She slowly lowered her tea cup to the saucer
and very carefully set the saucer and cup down to the coffee table.
"I see," she said after a moment of silence.
"Ma'am, there's one more thing," Sam said, nodding to me.
"Oh, right," I said, adding, "There is one more thing. I've decided...
I mean, Sam and I have decided, that I'm going to dress and live as a
girl from now on."
My throat constricted. I couldn't say more.
"I see," my Mother repeated. "Well, Matt, that's a lot to tell me over
one cup of tea. How long have you been gay?"
I swallowed hard.
"I don't know," I managed to say. "When does a person know something
like that? All I know is that Sam is the only one I ever... the only
man I ever..."
"Oh, Matt, come to momma," she said.
I rose and walked to my mother's chair. She pulled me down in her lap
and held me as if I were a baby.
"My poor, sweet little boy," she said. "I've always suspected that you
were... that way. One only has to look at you. I was so afraid that it
would make you unhappy."
"Oh, Mom," I said, beginning to cry. "I don't want you to be ashamed of
me."
"Never, my sweet," she said. "Never."
She held me and stroked me while I cried. After a while, she used her
right hand to lift up my tear-streaked face.
"Darling, I love you," she said. "Only one thing matters to me. Are you
sure this is what you want? I so want you to be happy, my son."
I glanced at Sam and saw that he also had tears in his eyes.
"Yes, Mother," I said. "I really believe Sam will make me happy."
"Then that's what I want too," she told me, kissing me on the top of
the head.
She turned and faced my companion.
"Mr. Hamilton... or may I call you, Sam?" she giggled. "After all,
you're going to be almost like my son-in-law."
Sam smiled his best grin. It really did make him look almost handsome
when he smiled.
"Please, do call me, Sam," he said. "And feel free to think of me as
your son-in-law. I like that."
She smiled back at him. I could tell she liked him.
"You will take care of my sweet child, won't you," she said.
"Mom!" I said.
"Ma'am, please believe me," Sam said, his eyes glistening. "I love your
son. I'll do my best to make him happy. Or maybe I should say 'her'
because after all, he is going to live as a girl now."
Mother looked at me curiously.
"That's really what you want... to be a girl?" she asked me.
"I... I want to try it," I told her. "Nothing permanent you understand.
But I want to live as a girl and see if I like it."
"I see," she said, clearly thinking of something. She looked at Sam.
"Mr. Ham... I mean Sam, only one thing about this bothers me," she
said. "Matt was scheduled to enter Harvard next month. I'd hate to see
the boy giving up his education."
I had already resigned myself to that. But Sam surprised me.
"So would I," he said. "No, I think Matt should start classes on time.
Of course, while he's living with me, I'll assume all financial
obligations related to his education."
Mother brushed that away as she always did when anybody started talking
about money or financial obligations.
"Whatever... that's not what I'm worried about," she said. "Harvard
accepted him as a boy. What will they think if he shows up for classes
as a coed?"
Sam laughed.
"Who the hell cares what they think?" he said. "Oops, excuse my French.
My point is they have no say in the matter. They've accepted Matt and
if they object to his preferred manner of dress or his sexual
orientation now, I can promise you they'll be facing the biggest,
fattest lawsuit that school has ever seen."
"Fine, then it's settled," Mother said.
"Wait, a minute - nothing's settled," I said. "I'm not sure I want to
go to school now... not the way my life has changed. Sam, we didn't
talk about this."
"There's nothing to talk about," he said, sounding stern. "You're far
too smart to pass up a college education. You will start school next
month and you will get good grades. I promise you, ma'am, I'll make
sure he attends to his studies."
"Call me, Catherine, Sam," my mother said. "I can see that we're going
to be friends."
If I wasn't so angry at the way they were dictating my life, I think I
would have been amused at how quickly they were bonding.
"Matt," my mother, still holding me in her lap, "I think I'll tell your
brother and sister about this tonight an dinner. Sam, why don't you
bring Matt by for lunch Sunday after church and that way Martha and
Danny can meet their new sister... he will be their sister by then,
won't he?"
Sam nodded.
"Oh, yes... in fact, when we leave here, I suppose we should do some
shopping, don't you think so, Matt?"
Before I could answer, Mother, jumped in.
"Where are you planning to go?" she asked.
"We hadn't really thought about that," Sam said.
Mother pushed me off her lap and stood up.
"Men!" she said in an exasperated tone. She walked over to the curtain
and pulled, signaling Marie to enter. The maid appeared in less than a
minute and did a little curtsey.
"Marie, I'm going out," Mother announced. "Call Edna at Marches and
arrange a private audience. Then call Maurice and tell him I'll need
emergency service, say at 5 p.m... we'll pay his people overtime. That
won't be a problem, will it, Sam?"
"Not at all, Catherine," he said, wearing an odd smile.
"Good, then I think I'll join you this afternoon," she said. "I think
you men need my help to transform my pretty son into my beautiful
daughter."
Sam was grinning broadly. This was going better than he had ever hoped.
I gritted my teeth and pretended I was happy to have my mother's help,
but in truth, her enthusiasm for my transformation made my skin crawl.
But what could I do? Tommy drove the three of us to Marches, the
exclusive (and expensive) dress shop where Mother and Martha did most
of their shopping. I was mortified when she greeted her friend Edna,
the proprietress of the shop, with a kiss and a hug and a full
explanation of how we were there to outfit her feminine son in a full
feminine wardrobe.
I could see Edna's eyes light up as she thought about the magnitude of
the sale she would be making.
She was, I have to admit, quite nice to me, even when she made me strip
down to my underwear in order to obtain my measurements.
"Hmmm, 30-26-32," she announced. "Matt, with a little work on your
waist, you could find work as a model. You know," she turned to Sam and
my mother, "quite a few of the top models in New York and Paris are
really boys. Oh yes, they have that slim shape the designers want...
although why they want models without breasts and hips has always
baffled me."
Then she called to one of her assistants.
"Let's see if we can't improve his shape a little," she said.
An assistant approached with a rectangular white strip of elastic
material, maybe 12 inches by at least two feet long. It was positioned
long-wise with the middle on my belly and the ends were wrapped around
my waist. I saw that the outside of one end and the inside of the other
were covered in a velcro-like substance.
"In the old days, we used to use wire or cord to close the girdle,"
Edna said. "You might get it a little tighter that way, but tying off
the cords in back always left lumps that were hard to hide. With
modern, form-fitting dresses..."
As she talked, she was pulling the two ends of the girdle.
"Now take a deep breath and suck in as much as possible," she ordered.
I did as I was told. She closed the girdle with a jerk, pressing the
velco together to form a firm, slip-less seal.
"I can't breath like this," I gasped.
"Nonsense," Edith said. "Girls put up with worse that this for
centuries. It's a little uncomfortable, I grant you, but you'll get
used to it. Take shallow breaths."
I was trying, but I didn't feel like I could get any air in my lungs at
all.
"Now, let's see what we've got," she said, slipping the yellow
measuring take around me again. "32-22-33 - a much more girlish shape,
you'll admit."
I'd admit anything to get out of that device of torture.
Of course, the models who displayed the outfits she was trying to sell
us, were as slim and shapeless as I was without the girdle. None of
them had tits to speak of. But when she was talking about how
flatchested I was, Sam whispered something to her and she looked at me
and giggled.
It would be several hours before I knew what they were laughing about.
I was given no voice in the selection process - not that I wanted any.
Still, Sam and Mother discussed each outfit and decided which to buy
and which not too. They had a few disagreements, but Sam usually
deferred to her.
The few times they asked me, I tried to play my part and sound
enthusiastic, but in truth I was just a bit dazzled by it all.
I thought we had finished when they had agreed on more than a dozen
outfits - ranging from casual fun-wear to an elegant ball gown with a
low, off-the-shoulder top and a wicked slit down the side of the floor-
length shirt.
But it turned out we were far from through. Next, Edna offered a wide
variety of footwear. Sam rejected most of the comfortable-looking flats
for a variety of heels - all the way up to a ridiculous pair of five-
inch spiked sandals with a strap around the ankle.
"You're so lucky you have such small feet, honey," Edna said. "Most men
who try this are limited to a the larger sizes and the selection is
just not as good."
Next was the selection of a wide variety of lingerie - I never knew
women wore so much and such a wide variety of stuff under their
clothes. We bought panties, bras, corsets, bustierres, panty hose,
garters, stockings, slips and a few items I never have figured out.
Again I thought we were done, but Sam cleared his throat, looked at my
mother and said:
"Catherine, I don't want to embarrass you... but nighties?"
I'm afraid nothing embarrassed my mother that afternoon. She spoke to
Edna and the next thing I knew, the parade of models resumed, this time
wearing a variety of nightwear ranging from sexy to downright naughty.
"Men pay good money to see shows like this," Edna giggled.
"Don't worry, this is costing me good money," Sam replied.
Just like the very rich to complain about money, those who just have a
lot of money never talk about it - for fear of having too little of it.
Those who have a lot of money complain about the cost of everything.
Sam and mother ended up buying another dozen nighttime outfits. To my
chagrin, it was my mother who suggested the naughtiest teddies and the
sheerest nightgowns.
Finally, we were done and Sam was giving Edna our new address (which I
still didn't know) to ship our purchases to. Mother was standing with
me when she glanced at her watch and muttered a curse. She pulled a
cell phone from her purse.
"Maurice... Catherine," she said. "We're running a bit late, but we
should be there in... oh, another 20 minutes... That's sweet of you. I
assure you we'll make it worth your while... What?... Oh, the works,
we're transforming a boy into a girl... Yes, I thought that would
interest you... bye."
I must have had a quizzical look on my face.
"Oh, Maurice is like you, dear," she said. "He likes men. He used to
have a girl-boy working for him and the girls told me they dated."
Her casual acceptance of my supposed homosexuality caused me to
shudder.
So did the greeting I got from Maurice when we arrived at his shop
after normal closing hours.
"Oh, Catherine... is this the pretty boy I get to transform?" he said,
hugging me and kissing me on both cheeks.
Maurice was, how do I say it... he was flaming.
He didn't really look that feminine. He was large and middle-aged, but
he minced around the shop with the kind of limp-wristed attitude that
movie fags parody.
I was stripped then received a body-wash from one of his girls. Next,
I was laid nude on a table, where I endured a full body wax to remove
every stitch of hair from my body. I say every stitch, but there were
two exceptions - my head and...
I saw Maurice whisper to Sam, who was observing everything with a
smile. Sam nodded and whispered something back to the gay hairdresser.
I learned later that they were discussing the tuft of hair just above
my dick. Maurice had one of his girls (thank goodness, I might have
lost it if he had gotten near my organ) trim the dirty-blond hair with
a pair of scissors, then shave what was left into a small rectangular
patch about an inch wide that ran from four inches to one inch above my
dick.
Only when that was done did Maurice hand me a small rubber item that
slipped on like a pair of panties. He called it a gaff and said
professional female impersonators wore them to hide their male parts.
To my shame he told me how to fold back my dick and slip it on.
I welcomed the chance to add a little modesty, even if I resented the
implication that I was now a female impersonator. I resented it... but
couldn't deny it.
My new status was reinforced when Maurice handed me a pair of lace
panties to don. Apparently, Edna had sent a few items to the beauty
shop. I slipped the delicate undergarment over my newly smooth legs and
pulled it into place. The panties covered my gaff and gave my lower
body a distinctly feminine appearance.
Maurice took care of my upper body as two of his assistants worked on
my nails - one shaping and painting (a shocking pink!) my toes, while
another girl shaped and painted (the same shade), my fingernails.
While they were working, Maurice took a small brush and painted circles
around my nipples with that turned out to be a special cement. He then
carefully fitted false breasts on my chest. They felt heavy and
amazingly lifelike. He used a flesh-colored makeup to blend the edges
with my skin. When he was finished, it was impossible to see that they
were not real.
"I gave him 36 C cups - that's about right for his frame," Maurice
said. "Of course, if you want something larger..."
Sam shook his head.
"Those are fine... in fact, they're beautiful," he said.
"Now, you'll only want to do this on special occasions," Maurice said -
to Sam and my mother, not to me. He handed Sam (not me!) the bottle of
solvent that would remove the adhesive. "The glue will hold them in
place, even if he should go swimming or engage in [he cleared his
throat] strenuous activity. However, too much use will irritate the
skin and cause a nasty rash. I'd recommend that he not wear these more
than 10-12 hours at a time and not more than... oh, two or three times
a week should be okay. If you want something more permanent, I'm afraid
you better see a doctor."
He did provide foam inserts I could wear to fill out my bra on normal
occasions.
"Fine, but Matt probably won't need them," Sam said. "He doesn't mind
that people know he's a boy wearing girl's clothes do you, darling?"
I forced a smile and answered in the affirmative. It was a lie, of
course. If I had to dress as a girl, I would have preferred that
everyone think of me as a girl.
I must confess I was starting to look like one. Maurice fastened my
first bra around my chest, covering, yet somehow enhancing, my fake
breasts. Then he fitted that hated corset around my middle again. I
think he was a bit stronger than Edna and that allowed him to squeeze
just a shade more from my waist.
I was standing there gasping from breath when he gave me one of the
pink robes his normal customers wore and let me sit down in a
comfortable chair while he worked on my hair.
My dirty blond hair was fairly long for a boy, but not as long as a
girl might wear. At least that's what I thought until Maurice got
through with me. He cut and shaped and curled for more than an hour.
When he finished, I couldn't believe what I saw. It was a short, but
definitely girlish bob.
"Almost done," he said with growing excitement. Then he went to work on
my face, plucking eyebrows, brushing something on my cheeks, doing
something to my eyes, the finally using a small brush to paint my lips.
"For one this young and naturally beautiful, we don't want to use too
much," Maurice said as he worked. "But she will need to learn do this
for herself."
"Hmmm, that might be a problem," Sam said. "I don't suppose you
would..."
"Oh, sir... as honored as I would be... it's simply impossible with the
shop and all," he said. "However..."
"What are you thinking, Maurice?" my mother asked.
"Well, madame, I do have a friend..." he stopped abruptly and turned to
Sam. "Sir, you seem to be a man of means. I wonder if you wound
consider engaging a ladies maid to help your young lady?"
"A lady's maid?" Sam said rubbing his chin. "I take it you have someone
in mind."
Maurice smiled and gave Sam little shrug that seemed to say, "You
caught me."
"Indeed, I do," he said. "I have a friend who likes to be called Fifi
and play at being a French maid. She's been passing for years and knows
all the little tricks. She would be perfect to pass on her knowledge to
this young beauty."
I hated the way they talked over me as if I wasn't there.
"She's a bit older now and finds it harder to find positions," Maurice
said. "I'm sure she would be quite willing... if you think it a good
idea."
Sam did to my chagrin, giving Maurice his card and telling him to have
Fifi call his office to set up an appointment.
By this time Maurice was finished with my face. He wouldn't let me see
it yet, but I could tell by the looks on Sam and Mother's faces that he
had done a good job. Then he did something that I expected, but was
dreading. He took a sterilized punch and prepared to pierce my ears. He
apologized that all he had to keep the holes open were small gold
studs.
"I knew we forgot something," Sam said. "We should have bought some ear
rings!"
"Here," my mother said, pulling the large gold hoops from here ears.
"She needs them more than I do."
So Maurice fitted my mother's hoop earrings through my new holes.
Next he helped me into the dress Edna had sent over from her shop. It
was a short black number that barely covered my new breasts - now I
knew what Sam and Edna had laughed about... this number was tailored to
fit my new shape. A pair of delicate straps looped over my bare
shoulders to hold it up. The dress hugged my body to below my waist
where it suddenly flared outward, dropping to mid-thigh length.
"I think you'll need a little training before you handle a really short
dress," my Mother said. "There is a trick to it... I hope your Fifi can
show you."
"I'm sure she can," Maurice, now kneeling to roll the nude stockings up
my shaved legs, said. These sheer hose had thick, but lacy elastic at
the top to hold them up without garters. When they were up, he fitted
me with a pair of black dress sandals with three-inch heels.
"Sam, I'm not sure I'm ready to handle anything that high," I said.
"That's okay, honey," he said, smiling again. "Just take small steps
and hang onto my arm."
"You'll do fine, sweetheart," my mother said, kissing me on the cheek
and then helping me rise. I wobbled unsteadily, but found that if I
kept my weight on the balls of my feet, I could walk. Only when I
stopped and stood still could I manage a bit of rest by allowing some
of my weight down on my heels.
I still felt as if I was standing on the side of a very steep, very
slippery roof.
I was so intent on maintaining my balance that it was a moment before I
realized I was standing in front of a wrap-around, floor-length mirror
with Mother on one side of me, Sam on the other. They both had the
goofiest expression on their faces.
It wasn't until I looked - really looked -- at myself and understood
the look they shared.
I was beautiful!
I know that sounds arrogant and I don't mean in that way, but I'm
trying to be honest here. My eyes stared at the bottom, where I could
see my pink toenails showing through the open-toed sandals. Above were
as pretty and as feminine a pair of legs as I've ever seen. Above that,
my corset gave a feminine curve to my body that would have turned me on
if I hadn't known if was all foam and rubber. But what really made the
difference was the face above that. Maurice's makeup job complemented
and enhanced his hairdo in a way I didn't understand. All I know was
that the total package screamed woman... if I had met this girl at a
debutante ball or in a bar or even on the street, I would have been
attracted to her. In fact, I think I was - I hate to say it, but I felt
the stirrings of my hidden manhood beneath my gaff.
"Oh, my new daughter is so beautiful," my Mother said, "Your little
sister is going to be soooo jealous, Matt."
"Catherine... we can't keep calling this beautiful feminine creature
Matt, can we?" Sam said.
Why was he asking her?
"You're right, Sam," she said. "What shall we call her? I always
thought if I had another daughter I'd call her Elizabeth, after my dear
aunt."
Sam nodded.
"That's nice, but I've always been partial to Robin," he said. "It's
so... androgynous."
I saw the pretty face in the mirror crinkle into a pout. Damn, even
when I got mad, I looked cute!
"Don't I get a say in this?" I asked. "I'm not some doll you're
dressing up."
Sam and Mother were immediately contrite, especially Sam, who put his
arm around me and gave me a peck on the cheek.
"I'm sorry," he said. "You're right of course. You should be the one to
choose your new name. What do you like?"
Ooops, I didn't want to pick a feminine name. I was just reacting to
how they were controlling everything and acting as if I wasn't there.
But now I had put myself in a position where I had to pick out a girl's
name for myself.
Oh, well, if I must...
"Do either of you remember Shakespeare's Twelfth Night?" I asked them.
Both shook their head. That didn't surprise me. "The main character is
a young woman who disguises herself as a man to find her brother. She
saves him... and also finds herself a husband and..."
I faltered. I don't know why I had said what I did.
It had a powerful effect on Sam, who wrapped me in his arms and
squeezed me so tight it almost hurt.
"And what is the name of this cross-dressing woman?" he asked softly.
"Viola," I answered.
"Then you will be my Viola," he said, kissing my painted lips for the
first time.
I was embarrassed to be in his arms in front of my mother (not to
mention Maurice and his staff). There was another feeling, beyond the
embarrassment, but I was loathe to admit that, even to myself.
"Please, Sam, you'll muss my makeup," I said when he broke this kiss.
He laughed at that.
"She already sounds like a woman," he said to my mother.
I think Sam would have stood there holding me forever if Maurice hadn't
cleared his throat and announced that he needed to send his staff home.
"My god, is it already eight o'clock," my mother said.
"You're right... It's already past my dinner time," Sam said.
"Catherine, why don't you join us for dinner. I have a standing
reservation at Revere's. Wouldn't you like to see me show your new
daughter off in public?"
"I'd love to, Sam" she said. "But I've got two more children at home
and they'll be wondering what happened to me. I've got to get home and
break the news to them. Besides, I think you two lovebirds need some
time alone... am I right Viola, darling?"
I said nothing. But I'm afraid I blushed.
"Another time, then," Sam said.
"Of course," my mother said. "And don't forget, you two are coming to
Sunday dinner after church."
Sam agreed and offered to drive mother home. But she insisted it was
silly for us to drive all the way out, then return to town for dinner,
so we put her in a cab.
Just before she got in the back seat, she stopped.
"I just thought, if you two are going out... Viola will need these more
than I do," she said, removing the two gold bracelets she wore on her
right wrist. "They go with the ear rings anyway. And here..." She
removed the delicate woman's watch from her left wrist and fastened it
to mine. "... you'll need this too."
"Mom, I can't take your watch and bracelets," I protested.
"Consider them a loan... bring them back Sunday," she said. "I'm sure
Sam will buy you some of your own by then. Remember what they say... "
She leaned over and whispered, but loud enough for Sam to hear. "...
Diamonds are a girl's best friend."
Sam was grinning at her hint.
Mother hugged me and again started to get in the cab. Once again she
hesitated.
"I think you could use one more accessory," she said.
I looked at her curiously. She hesitated once again, then slipped off
the glove on her right hand (Mom was old school - she wore gloves
everywhere) and pulled off a small gold ring, set with a small emerald
in the center of a ring of diamond chips. It wasn't an especially
expensive piece (worth maybe a couple of thousand on the market), but
it was beautiful and I knew what it meant to her. The ring had been in
her family for five generations.
"Oh, momma, no," I said.
"Yes," she said, slipping the ring on the second finger of my right
hand. "See, a perfect fit. You don't even have to have it re-sized."
"But, momma..."
"No buts," she said, hugging me again. "It's supposed to go to the
oldest daughter when she turns 18... well, you are 18 and now you are
my daughter, my lovely Viola."
She kissed my cheek and finally got in the cab.
"See you Sunday after church!" she shouted through the window as the
cabbie peeled off.
I was a little dazed standing there on the sidewalk in my high heels,
wearing my mother's jewelry. I felt Sam put his arm around my shoulder.
"That was sweet of her," he said.
"My sister Martha will kill me," I said. "She's had her eye on this
ring since she was six years old."
Sam just chuckled. I liked the way he laughed.
"Your mother is a very special person," he said.
"I think you got along better with her than I do," I told him.
"No... she likes me, but she loves you," Sam said.
I was still thinking about that when he led me to the limousine. I was
a little shaky, but I make it by leaning on his arm.
Part Five: Viola's debut
The look on Tommy's face when he saw me was priceless.
"Boss, where did you pick up this beauty?" he asked.
Sam told him my new name and Tommy surprised me by bending over and
planting a kiss on my cheek. He then drove us to the restaurant.
We were silent during the short drive. I think I was in shock - I never
expected my mother to take it like that. Sam was, I think, lost in the
illusion he created. He was content to hold my hand. He laid his head
back on the seat and gazed at me with undisguised rapture.
Revere's is, of course, the trendy up-scale restaurant overlooking the
Charles River. The view was magnificent at night, but I had the
strangest feeling that every eye in the place was on me as Sam guided
me, hanging desperately on his arm, across the room to his table by the
window.
I was much too nervous to eat. I let Sam order for me. I barely sipped
the wine - I definitely didn't want to get drunk tonight - and merely
tasted my spinach salad. I was able to get down a couple of giant
prawns, grilled and basted in lemon butter, but I couldn't get a third
one down and let Sam finish my other three.
During the meal we talked about Shakespeare. That surprised me, but he
started it, asking me to tell him about Viola and the Twelfth Night. So
I told him the story and that led to a discussion of the Bard's other
shipwreck play, The Tempest, and a million other things and before I
knew it, Sam had finished his coffee, paid the check and was helping me
up.
I dreaded what I knew must come next. But part of me was curious and
maybe a little bit excited to. I expected him to take me to his home,
instead, Tommy drove us to the Kenmore Hotel, where a doorman was
waiting to escort us to the Bridal Suite in the penthouse. There was a
fire burning in the fireplace, a large silver bucket held two big
bottles of champagne and there was a table laid out with tasty
delicacies covered in plastic wrap.
"I thought our first night together ought to be special," Sam said,
taking me in his arms and kissing me with real passion. I didn't
resist, but I'm not sure I really responded either, although there was
again a disturbing movement beneath my gaff.
Sam pointed me to a door to one of the bedrooms.
"If my orders were carried out, Edna should have left you a selection
of nightgowns on the bed," he said. "Pick out the one you like. Oh, and
there's a bottle of the solvent in the bathroom. Go ahead and take
those things off... they don't do anything for me... and, besides, I
wouldn't want you to get a rash or anything."
He sounded almost apologetic as he said the last, so much so that it
made me stand on my tiptoes and give him a peck on the cheek.
Then I retired to prepare for my deflowering.
There were three nightgowns on the bed - one very plain cotton one, one
very naughty short teddy and one long and sheer and elegant. They were
so different I wondered if this was some kind of test.
I thought about that as I stepped in the bathroom and stripped off my
dress, my underwear, my corset and my gaff. I thought about leaving on
the hose, but decided not to. I also removed all my new jewelry, all
except my earrings and my mother's ring.
It took a few minutes to get the breasts off, even with the solvent. I
made sure I washed the area well with a soft body soap and water. I
peed, then I stared at my feminine face in the mirror, trying to think
of an excuse to stay longer in the bathroom.
"Well, Viola," I told my reflection. "I suppose it's showtime."
That was how I told myself to play it. I had always wanted to act.
Well, I was now an actor (or maybe an actress) playing a role.
I couldn't put off making a choice of nightgowns any longer. Acting
more decisive than I felt, I picked up the long, elegant nightgown and
slipped it on. There were a pair of matching panties underneath, but I
left them on the bed - Sam would just take them anyway.
I thought for a second about putting my high heels back on, but decided
against it. Instead, I took a deep breath and walked slowly back to the
living room in my bare feet. With every step they peaked out from
underneath my gown - looking so girlish with my pink painted toes.
Sam was lying on the thick rug in front of the fire, sipping a glass of
champagne. He had changed into a silk kimono that left his hairy legs
bare. I think if he would lose 10 pounds and tone up a little bit, he
would be a handsome man.
I did like the smile I saw as he looked up at me.
"I thought I was going to have to call the BPD to go looking for you,"
he said. "It always takes you women so long... but looking at you, it
was well worth the wait."
He patted the carpet beside him.
"Join me... Viola," he said with a slight hitch in his throat.
I slid beside him and tried to relax as he took me in his arms. His
lips were on mine, his tongue probing. I tried to respond, but I was
tense and terribly afraid."
Maybe he sensed my fear. I don't know. For some reason he backed off a
bit.
"Tell me something, Viola," he said. "Why did you choose that
nightgown?"
"So it was a test," I said.
"Not really," he said. "Well, maybe a little... I just wondered what
you were thinking."
Did I ever know? Could I tell him?
"I guess I was thinking about what kind of woman I wanted to be for
you," I told him honestly. "The boy in me wanted to wear the modest
cotton nightie, but I knew no real girl would wear that to bed with her
boyfriend. I wear that when I sleep alone."
"What about the teddy?" he asked.
"That's something a slut or a hooker would wear," I sniffed, as if
offended he would even think I would wear such a thing. "I'm from a
fine old Boston family and if I'm going to be your woman, I'm going to
be a lady. This is a beautiful, elegant nightgown... the kind a classy
woman would wear to sleep with her man."
He looked at me curiously.
"I see that," he said. "But I thought the nightgrown you're wearing
came with a matching pair of panties."
I was losing myself in the part I was playing.
"But Sam, darling, even a lady likes to feel a little bit like a slut
with a man she loves," Viola said... Viola, not me.
That answer delighted him and he was kissing me again, his hands
roaming my body. After the longest time, he whispered:
"Let me show you how good it can be."
Then he slid down and I felt him lift the front of my nightgown above
my waist. His first kiss was on the inside of my upper thigh. For a
minute he kissed and licked my newly shaved upper legs, always getting
closer and closer to my groin.
I was so confused - scared, excited and mesmerized all at once - that I
didn't realize my dick was hard until his mouth was on it. I don't know
how good a cocksucker Sam was... I have nothing to compare it to, but I
knew what he was doing to me was giving me incredible pleasure. He
licked and sucked and kissed, both my small (maybe five inches at full
extenuation) penis and my tiny balls.
I'm not totally naive, so I warned him before I came. He surprised me
by taking my cum in his mouth. I could taste it on his tongue and lips
when he slid back up to kiss me. I thought I would be disgusted, but it
wasn't that bad.
I knew it was my turn to do him next. Part of me was reluctant to do
it, but another part of me made me mimic his earlier moves before he
could ask or tell me to do so. I was lost in my part and my part was
that I was his gay girl-boy lover and I knew that my character would
want to suck Sam's dick.
I started as he did, kissing all around the groin, but I'm afraid I was
not as patient as Sam was. I couldn't help myself, taking his dick in
my mouth and swallowing as much of it as I could. His penis was not one
of those monsters you read about in porn novels. It was probably about
eight inches and fairly thin - not as thin as my pencil dick-but thin
enough that I could wrap my thumb and forefinger around it with my long
red fingernails just touching.
I was holding the base of his cock, sucking for all I was worth, when I
looked up at his face and our eyes locked. He smiled at me and looked
so happy I couldn't help smiling back at him, my smile distorted by the
dick in my mouth.
I wondered if I could swallow his cum as he had swallowed mine. Like a
gentleman, he warned me, but I think I could tell anyway that he was
close from the way his hips bucked. Somewhere deep inside, a voice
screamed at me not to do this, but the part of me that was playing the
part squelched the little voice and took his cum - only a small stream
drizzling out the corner of my mouth.
I used a finger to wipe it up, then looked at the cream on my finger,
wondering what to do with it. I still had the bulk of his ejaculation
in my mouth, swirling it around with my tongue like I was a wine-taster
judging a new Bordeaux. His cum actually had no flavor at all, but the
texture felt so good going down my throat that I absent-mindedly licked
the cum off my finger and swallowed that too.
"My god... you are something," Sam exclaimed and I suddenly realized
that he had been staring at me during my little taste-test.
So what, Viola said. Let him stare. Then that part of me that was her
leaned over and took his shrinking dick in my mouth and licked it
clean. Only then did I slide back up and give Sam a fierce kiss in the
mouth.
I knew I had one more test to face, but Sam wanted to take a break
first, so we snuggled on the couch - me curled up in his lap with my
arms locked around his neck while he poured champagne down my throat
and fed me little tidbits from the appetizer table between sweet
kisses.
Funny thing about the champagne, I had drunk that brand many times
before and I thought I knew the taste. This was different - could
drinking it as a chaser to cum make that much difference.
I told Sam my theory. It made him laugh. He brought my glass to my lips
and I drank it hungrily.
Earlier, I was careful not to drink too much because