Mattie: Learning to Love What You Have
By Kelly Ann Rogers
I haven't written, or, more accurately, posted anything in a while. Those
big, novel length stories I posted in the past kinda drained me OMG! I
can?t believe I wrote three novels)! Then I got really busy in RL and
worst of all, my muse fled. I'm sticking my toes in the water again with
this confection. It's a flirtation with themes that often occupy my
thinking, but which I'm not ready to directly write about. Instead, this
is a sexy little story just for the fun of it.
I love captioned images. The best can tell a story in a few lines.
Others get me thinking, sometimes, of a story I'd like to write. They
never get written, of course, until this one captured me. This story is
just for the fun we t-girls get from watching a man become an increasingly
feminine, aware, sexual being. It describes how Matt becomes "Mattie,"
though not the Mattie his wife and master would have created. Like my
other characters, Mattie creates herself.
I dedicate this story to the anonymous authors of the two captioned images
that lead it off. The images represent, respectively, its beginning and
end. I hope the journey is worthwhile for you.
And as always, thanks to the wonderful authors who volunteered to read
this for me. First, the fantastic Leeanne Montgomery, who has so
enthralled so many readers with her current exquisite sissy saga, Fall to
Grace, and also to MEPS, who gave us the brilliant Team Spirit II, a
powerful story of love and redemption, and almost certainly the best
sequel ever posted to FM. If you don't know who these two authors are, do
yourself a favor and find their stories; they?re both here on FM. But do
wait at least till you finish reading this!
"Mattie! We did it! I can't believe it! We're gonna be rich!"
Pamela jumped up and down with joy as she waved the slip of paper with her
bank account number on it.
I was a little more glum - scared too. "I don't know about we. You're the
one who just got a Swiss bank account with a million dollars in it."
"But it's for both of us. And you'll be living in the lap of luxury for a
year. You saw the pictures. Roberto has a town house in Manhattan, a
mansion in Palm Beach and apartments in Paris and Buenos Aires. And then
there's his home here. He's obviously really, really rich. I hear he's a
billionaire!" She waved the slip of paper at me again.
Then she settled down and looked at me with an arched eyebrow, a cutely
tilted head and a smile I couldn't interpret. She studied me for a
moment, and I felt like a mouse to her hawk. I'd been seeing this look
more and more recently, and it made me uneasy. It wasn't like the looks
of joy and love and admiration I used to get from her.
With a toss of her head to throw her dirty blonde hair off her face (and
that was another thing ? after years of wearing a short stacked style that
was both business-like, sophisticated and easy to care for, she was now
looking downright sultry, with long wavy hair, the ends curling
delightfully on her shoulders), brightened quickly and changed the
subject. "I'm so glad I finally decided to let you dress up and to take
you to transvestite night at the Silver Slipper. We never would have met
Roberto otherwise."
"It was about time. I'd been trying to convince you to do it for years."
"Well, that's true, but I wouldn't have done it if you hadn't improved
your look so much. Being out of work gave you the time to grow your hair,
start your little boobies and practice your feminine behaviors. I love
the way you hands flutter about your face when you talk and the sway of
your hips when you walk - Very hot!"
I wiggled my hips a little as I contemplated my walk. It never occurred
to me that it might be hot; I was just shooting for feminine. "I guess,
and it has been fun, but I don't understand why you all of a sudden
started being so supportive." I had decided quite a while ago that she
must be plotting to get rid of me.
"What's to understand? You were home doing nothing, so it only made sense
for you to take care of the house and become my little homemaker. You're
the one who always wanted to dress like a girl, and this was your perfect
opportunity, especially when we had to move because of my new job and no
one in our new neighborhood knew you as a man. You just became my female
partner, though you looked pretty much like some kind of dyke." She
frowned at the memory.
"Yeah, the neighbors weren't so cool with that at first. They weren't
quite sure what I was. But I guess they're all becoming more comfortable
with my burgeoning femininity. At least they don't see me as a freak
without a gender anymore, although they're still a little concerned about
us being lesbians."
"Yeah," she frowned again. "It had never been part of my life plan to
have everyone believe I had become a lesbian. I think I was quite generous
in allowing that just so you could indulge your tranny fantasies."
I didn't like the way she said tranny, it had too much of an edge to it.
It sounded more like a putdown than anything else. But still, she was
right, and I owed her for her generous spirit. That's why I totally threw
myself into the housewife-helpmate role. Not only was she a highly
successful businesswoman who was now our sole breadwinner, but she had
really put herself out for me.
"You're right," I agreed with her. "I can't imagine anyone being more
generous. And I've tried to do everything I can to support you in
return."
"You are a sweetheart," she replied in a throw-away sugary tone that was
simply another put down. But once your year with Roberto is over, I don't
think anyone will mistake you for a dyke again. I think by then, you'll
want your own boyfriends."
"Pamela! Don't joke like that. And I don't like that smirk on your face.
I know you're just joking, but it makes me worry. And I don't see why
you're so excited to get rid of me for a year. I never would have agreed
to that on my own. And I don't like the idea of this contract. If things
don't work out, I'm stuck with him anyway. It's so risky, why did you
force me to agree to that?"
She could tell I was getting frantic and moved to sooth me. Why was I
becoming so easily upset lately? I was supposed to be on some kind of
medicine for my anxiety that would actually calm me down, but instead I
was more irritable and had real problems controlling my emotions, even
more than when I first went on female hormones. They made my skin softer,
my hair thicker and had started to give little boobies. I was sure that
my new meds weren't simply anxiety pills, but more likely more hormones.
It was all part of her plot to get rid of me.
And now this contract - I was more than paranoid!
"Mattie, my sweet, relax. That's the difference between a business woman
like me who understands risk and reward and an old-fashioned accountant
like you, who doesn't. If you hadn't been so afraid of risk, you wouldn't
have lost your job."
That was certainly true. I had been comfortable at my job, which, because
of my skill as an analyst, came along with a nice, fat, dependable salary.
When a new start-up offered a combination of a lower salary, but
potentially more lucrative bonuses and stock options to jump ship, it just
seemed too risky. So I had stayed at my old-fashioned firm instead.
Within a year, the start-up had attracted big hedge fund stocks and driven
out of business. When I went to them looking for a job, they said that I
was too risk averse and didn't fit their company culture.
She stroked my longish, mousy brown hair (I was still trying to figure out
what color it should be) and let her hand rest on my cheek. "Everything
will be just fine; you'll see. If you hadn't lost your job, we never
would have even imagined living like this, and even if Roberto had come
along while you were still working, we certainly couldn't have agreed to
his plan."
"Just think! He's rich, and you're going to be his wife. Well, sort of
his wife, I guess. Probably more like a consort or concubine. But you
will become the ultimate femme sissy."
"Pamela! I don't want to be the ultimate femme sissy! How many times
have I told you that? I just want to be a regular girl, err... woman.
It'll be fun to be pretend to be his wife, I hope. What's a consort
anyway?"
She just shook her head, dismissively. "Google it."
And I think I heard her mutter under her breath, "Twit."
I just frowned, but continued on. "And I am looking forward to dressing in
designer clothes and having my hair and make-up done by professionals," I
put my hand on my hip and vamped for her at the thought. But don't you
think this whole thing goes way too far? A whole year? And no way out?
And I have to do whatever he says?" I was getting agitated and my hands
were flying around my face, fingers fluttering uselessly.
"Sweetie, you always worry so much. A year isn't all that long, and
giving Roberto control over you, just as an old-fashioned husband should
have over his old-fashioned wife, earned us another $500K. Really, he paid
us a cool million just to have you around as his companion for year,
promised you at least $250 thousand in clothes and jewelry, a lifestyle
that you could never have dreamed of, and then another half mil for you
to 'love, honor and obey' him. We're still married, so a contract was the
only way to make it work. And besides, let's face it: you can never get
enough sex. Whatever the male equivalent of slut is, you're it and you
know it."
I couldn't deny that; in fact, I was proud of it. I was always horny.
One thing that Pamela never lacked for was sex, although that didn't keep
her from complaining about the size of my penis. I'm not sure King Kong
would have been big enough for her. Then again, I'm not sure he could
keep up with her like I did. My dick may not have been the biggest in the
world, but I was insatiable when it came to giving organisms. My favorite
kind of sex was, "more."
She waved that slip of paper at me again. All I could think was that she
had the money, and I was going to be some rich man's toy - his wife in the
most old-fashioned way.
"Of course," she went on with a feral grin, "He is rather traditional and
will expect his '"wife"' to be the old-fashioned kind. You know, a lady
in the living room and a whore in the bedroom, which, by the way, he was
delighted to hear, you already are."
"I never agreed to sex! I'm not gay, how could I do that? The only
bedroom I'll be in will be down the hall from his, and it will lock from
the inside!"
She gave me that cocked-headed look again. But this time, it wasn't the
hawk eyeing the mouse; it was more like a cowboy sending one his steers
into the chute that leads to the slaughterhouse. I shivered slightly.
Pamela may have been the risk-taker in our family, but I was the one who
was setting off on the big adventure. A very rich man had promised us
almost two million dollars if I would live with him for a year as his
"wife." This was supposed to be a fabulous year for me ? a joyous journey
that would enhance my understanding of femininity while living a luxurious
life. The only thing was, instead of picturing Columbus setting off to
find the passageway to India to the cheers of Queen Isabella and her
subjects, I felt more like Thelma and Louise driving hell-bent for leather
off that cliff.
**
I was determined to set the right tone for Roberto at the outset so I
purposefully dressed conservatively as I set off to meet him. Pamela
almost laughed when she saw me.
"What are supposed to be, the school librarian?"
"I'm not going to give him the wrong idea," I pouted.
"Whatever," she giggled. I don't think you'll be wearing those clothes
for long anyway. I doubt if Roberto does dowdy."
Whatever.
His limo picked me up outside our home, and whisked me away to a spa. I
was a little put out because the limo driver gave me a most disparaging
look and a sarcastic little bow as he held the door for me. I mean, what
was his problem? This was a great Talbot's outfit I had worn several
times without being outed.
'Who cares what he thinks, anyway, he's only a dumb driver,' I thought as
he delivered me to the spa where I was to be pampered the whole day and
made over to suit Roberto. I was again somewhat put out when the woman in
charge of my care looked me up and down and muttered, "Oh my," as if I was
irretrievable. But that was the last bit of disparaging talk I heard.
They even listened to me as I expressed some of my own ideas about how I
should look. They just trimmed my hair slightly, creating a straight bob
that would grow out well. They also fitted me with a number of wigs, so I
could try a variety of looks. We agreed that dark was the way to go, so I
finally ditched mousy brown for lustrous brunette. I was utterly
delighted because I so worried that Roberto would want me with big blonde
curls, like some kind of bimbo! I wondered for a second just what Pamela
had told him about my behavior in bed. I didn't want him to get his hopes
up.
I was waxed, oiled, massaged, had my pores opened and closed, my eyebrows
perfectly shaped and my face cleaned three different ways. My toes and
fingernails were turned into little jewels, they had been cared for as
they were museum exhibits about to be put up for auction at Sotheby's.
First, the stunning Matisse, then the little known Gauguin, and them my
nails. I laughed at the delightful thought as I pretended to shield my
eyes from the light reflecting off my spectacular, glossy, iridescent red,
nails.
Then they did my face. Because Pamela had agreed to finance laser hair
removal when we first moved, there wasn't any hair left on my face to
worry about, and the operators were quite complimentary about my
complexion. I had used whatever Pamela did and her skin was radiant.
That, of course didn't stop them from giving me about a dozen skin
products that "you must use every day," some in the morning some at night,
just as the instruction booklet detailed. When they worked on my face, it
was as if a team of fluttery little fairies were doing my face with their
gentle little wings. My lips ended up a rich, bright red, which, I was
told is just the way Roberto always wanted to see them. Multiple tubes of
the same lipstick ended up in my bag.
Once they had finished, they cleansed the whole thing off and then guided
me as I reapplied it myself. They applauded when I was done. I had
always been good with makeup and preened with pleasure at their approval.
When all's said and done, what's the point of being a transvestite if
don't like to play with makeup?
They also had me try on an array of lingerie, most of which would have
made me come on the spot had I not been wearing a gaff. Corsets were also
on the list. They were as beautiful as the lingerie, but scarier. Could
my waist ever get that small? I had already dieted down 20 pounds since
we moved to Las Vegas. I wasn't sure I could get smaller!
At the end of the day, they fitted me out with scrumptious lingerie, a
lovely black polka dot dress, to die for heels and flawless makeup. They
fitted me with a big curly wig that gave the whole look a rather retro
feel. I could just imagine myself at the soda shop with a big ice cream
soda!
I guess the change was pretty impressive. This time the chauffer gave me
a real bow when he saw me, and said, "Madam, you look lovely. My name is
Mr. Hobbs and I it will be my pleasure to serve you."
Maybe he wasn't just a dumb driver after all. He was certainly a hunk.
His compliment, the smile on his face, and the practiced, formal manner he
adopted despite his rugged masculinity made me feel like Julia Roberts in
Pretty Woman! "Thank you Mr. Hobbs," I said as I held up my limp wrist
for him to help me into the car. Once I was settled, I looked up at him
from under my seductively thick eye lashes and said. "I do so ever look
forward to your services." I allowed my look to linger a bit too much
before I smiled and ducked my head, indicating it was time to go.
**
Although I entered his home with my heart fluttering and my mouth dry from
anxiety, Roberto couldn't have been more of a gentleman. He greeted me at
the door with a huge bow, a warm hug and an even warmer kiss on the lips.
He was so insistent, and his lips were so hot, that after a few moments I
just felt that I had to open my mouth and let his tongue in. I felt
positively risqu?! I was like, OMG; I'm playing tongue-tag with a man!
And I only reluctantly let him withdraw when he was done. I couldn't help
it. I had never been kissed like that before. He finished with little
pecks and licks. When we were quite done, and my eyes fluttered open, I
was looking dreamily up into his. I realized that I had just let my right
leg back to the ground. I had actually lifted it at the knee as he kissed
me! I almost came right there just thinking about what I must have looked
like. It was a sort of out of body experience. I sure hoped Pamela never
found out.
He was the perfect host as he showed me around his "small" Las Vegas home.
He gently guided me with his hand around my waist or shoulder. Once or
twice, he even took my hand in his, and I let him! He was so romantic! We
had drinks on the veranda as we watched the sun set, and then a long,
lingering dinner in an intimate parlor between our two bedrooms. He
regaled me with fascinating stories about his life, drew me elaborate word
pictures of his other homes and generally feel like a precious jewel.
What a man!
After dinner, he urged me to change, so we could meet again before bed, so
I selected a fabulous new set of undies, white because it was our first
night, sprayed the perfume that had been selected for me at the spa on my
wrists and neck (I wasn't ready to put it anywhere else yet), and draped
myself provocatively on a couch in my bedroom and waited for him to enter.
But he didn't show up for a while. What the fuck? I got bored waiting!
And my back started to hurt. Who knew being provocative could be so
uncomfortable? I rolled over onto my stomach to relieve the strain. Not
surprisingly, that's exactly when he decided to come in. His first look at
me was of my ass, set off by the white bows of my lingerie, pointed
towards the door, like I was some kind of gift.
He had knocked gently, but before I could react, he had stuck his head in.
He obviously didn't think he had to wait for me to give my assent. He too
had changed, and was wearing a dark blue silk dressing gown with his
initials embroidered on the left breast. He must have put on some
cologne, because he smelled amazing. His dark curly hair glistened in the
soft lights of the room and I was totally taken by his smoldering good
looks. I was trying to play my assigned role, but was actually somewhat
shocked by how easily I was falling into it. I let him charm me, and
before too long, we were again kissing, though I was intent on not letting
him go any further.
'What would my mother think,' I giggled to myself, 'if she knew her little
girl was putting out!'
I guess I needn't have worried because he stopped on his own, sat up on
the couch and began to tell me how things were going to be.
It was pretty much what we had agreed to in the contract. He was going to
pamper me as his treasured "trophy wife," and in turn, I would be
attentive to him and his needs, be his companion at home and arm candy
whenever he wanted to go out. I would be the hostess when he entertained,
and was expected to be especially lovely on such occasions. He
entertained many important guests and emphasized how important it was that
they felt cared for and valued when they were in his home.
He traveled a lot because he was a broker in some sort of import-export
business. That meant I would be home alone a good deal of the time, and
he expected me to perfect my feminine persona with the help of the staff.
Once I had mastered all the feminine arts, I would begin to socialize with
the wives of his friends and then, he predicted, I would be one of the
most popular socialites in Las Vegas!
"And finally," he said, "we will have plenty of sex. Pamela tells me you
are a total slut, and I can't wait to sample more of your charms." And he
again kissed me on the lips.
This time though, I recoiled. "What do you mean plenty of sex?" This was
getting out of hand.
"Well, of course plenty of sex," he smiled seductively. "You are my sissy
wife. All sissies love sex."
"No we don't," I replied, rather alarmed. "I never agreed to sex."
"My dear," he replied, a sarcastic edge to his voice. "Do you actually
think I agreed to take you into my home and perfect you as a woman and not
have sex with you?"
When he put it like that, no. I had been deluding myself. Worse, I knew I
had been deluding myself. My shoulders sagged and I could feel my eyes
tear up.
"Roberto, I'm not gay. I don't know how to have sex with a man, and I'm
not sure I want to. You're very handsome, but I like girls."
He looked into my eyes for a moment and then started to laugh.
"What?" I was offended.
"Did you really think I would spend all this money and make such
complicated arrangement with your wife and not expect to go to bed with
you?"
My mouth fell open as he looked at me with a bemused smile and the cutest
wrinkles in the corners of his eyes.
"Umm..." I was feeling really stupid. Could I have been so clueless? I
guess so. I had been in denial, and caught up in Pamela's excitement. She
was a great salesperson.
"Look at what you are wearing," he went on, "You presented your ass to me
in bows."
"Well, of course I did," I replied a bit huffily. "I'm a transvestite. I
love to wear fancy lingerie." 'Like Duh,' I thought.
"Of course you do," he replied delighted at my answer. "I'm a man who
loves to take fancy lingerie off his sweet sissy lovers." He smiled
confidently.
Shit. My hand reflexively went to my ass. It was bare, except for the two
beautiful, sexy bows that were basically in my crack. They were so hot I
had jerked off after I had put the outfit on and saw my ass in the mirror.
"But Roberto, I'm not gay. I can't have sex with you."
A huge smile lit up his face. "I know! And that makes it all the more
wonderful! I get to break you in! Your cherry will be mine!" He sounded
thrilled at the prospect.
"Pamela and I had the best time planning your future, and it will be as my
gay consort. Not only will you end up as the beautiful sissy you have
always longed to be, but you'll have precious little tits and a luscious
round ass. And before too long, you'll become an expert cocksucker and
crave the pleasure of a man who knows how to plow your scrumptious
bottom."
"No!" I gasped. This couldn't be. This isn't what I wanted. This isn't
what I had discussed with Pamela!
"Oh yes, my sweet Mattie," Roberto said as he moved in on me, grabbed my
arms and began to kiss my neck and shoulders. His left hand quickly began
to wander down my back to fondle my bare ass.
I started squirming, at first because the feeling of a man's hand on my
ass freaked me out. But in only a few moments, the shock turned to
something else, and I was squirming in a different way because this was so
amazingly erotic. I had never been treated this way and I was shocked to
discover liked it. This is so wrong, I thought, as I threw my head back
to give him better access to my chest. He reached up and undid my bra and
as he began to slide it down my arms, I again freaked.
"No!" I said more assertively as I sat straight up and twisted away from
him. Now we were sitting at arm's length on the couch and I was glaring
at him. He still looked amused, which made me angry. "Who do you think
you are, to take advantage of me like this? We hardly know each other."
My hands flew to my mouth as I realized my mistake. I had just implied
that if we knew each other better, this would be alright. "No, wait.
That's not what I meant. I never agreed to this. And I wrapped my arms
around my chest in the classic pose of a woman trying to hide her breasts.
Mine were not much more than an ample A-cup, thought they did have
sensitive pink nipples that expanded rapidly when I got excited
He stared at me for a few seconds, and then reached out and grabbed my
arms again. This time his grip was like iron.
"Mattie, my dear," he said, his voice almost a whisper, but hard as steel
nonetheless. "You are mine to do with as I please for a year. You signed a
contract. You will obey, or you will be punished. That was the deal you
agreed to. But it's your choice. Be my princess and I shall adore you,
or be my bitch and I shall get what I want anyway. It just won't be as
much fun for you." His eyes crinkled with delight.
We sat there staring at each other. I couldn't believe what I was
hearing, just as I knew it was the truth. Before I could really react, he
pushed me to the floor in front of him and said, "Now suck. I had
intended to seduce you slowly, but I can see that it's pointless to try,
at least for tonight."
I was stunned, overwhelmed by how fast things were moving, and feeling
totally out of control. Still, I resisted. "No."
"Fine." He grabbed me again and this time threw me over his lap. He
didn't even need to pull my beautiful panties down because my cheeks were
totally bare. The bows only hid my crack, but he untied them anyway. And
before I knew it, he was spanking my bare ass.
Hard.
I struggled to get free, but he was too strong. I felt ridiculous ? a
grown man, dressed in sexy lingerie being paddled on his bare ass like a
naughty child. But there wasn't anything I could do about. I eventually
just gave up and lay across his lap whimpering as he continued to beat me.
Through the pain, however, I was befuddled by how erotic his hard thighs
were as I bounced against them and squealed with each swat.
When he stopped, he pushed me to the floor in front of him and asked, "Are
you ready now?"
I wasn't, but I was still blubbering and couldn't talk, so I shook my
head, no.
He looked down at me, shaking his head. "Then I want you to jerk me off.
If you do, I'll leave you alone for tonight. If not, your punishments
will not only escalate, but go on for days. And each time after that you
say no, the length of your punishment will increase."
'Oh god,' I thought. 'This can't be real.' But given the effectiveness
of his spanking, I was afraid to imagine what else he might dish out. I
started having visions of dungeons and chains. So I wiped my face, got up
on my knees and reached for the tie on his pajama pants.
He put his hands on mine, and said, "Let me help, cara mia." And he undid
the knot and raised his ass so I could pull his pants all the way down.
"Take them off, please. And then sit next to me."
So there I was, on my knees, pulling a man's pants off. I may not have
been giving him a blow job, but I was surely practicing some of the steps
that lead up to one.
My first touch of his penis was electric. I mean, I knew what they felt
like, I had one. But his was so big and hot, so soft and hard. Unlike
me, Roberto wasn't circumcised, so playing with his foreskin was a new
experience. I pulled it down until the crown emerged, I couldn't believe
how alluring it was. I was almost ready to bend down and kiss it, but I
caught myself. What was happening to me?
He told me what he wanted me to do and how to do it. It took quite a few
minutes before he came and I caught his load with my hand.
"Swallow it," he instructed gently. "You'll be doing it soon enough, so
you might as well get used to the taste. All my sissies like it."
'No!' I thought, and bolted for the bathroom where I washed my hand in the
sink. I felt like Lady Macbeth trying to get that damn spot out. And
like her, I too new it was pointless. When I returned, Roberto was
sitting just as I had left him, his now turgid cock glistening with come.
"Wouldn't you like to clean it with your tongue," he offered. He was so
sweet it almost sounded reasonable.
I demurred, instead using the warm washcloth I had brought from the
bathroom. At least I was careful, and when I was done I impulsively gave
it a little pat.
He smiled and said, "Thank you my dear. I do think we made some progress
tonight, but we will still have a lot of work to do starting tomorrow.
"Oh, by the way, your room only locks from the outside," he smiled,
pulling a dark cord with a key on it from his pocket
Chapter 2
"Good morning mistress," a delightful voice with a vague Creole accent
reached into my awareness and led me to wakefulness.
"Uh, who are you?" I asked starting to sit up on my quite sore ass. A
slightly plump, but attractive woman wearing a sexy black and white dress
smiled at me.
I am Eva, Miss Mattie, and I am your maid. It is my job to see that you
have everything you wish. I will help you bathe, do your hair and makeup,
select your clothes and generally do whatever you need so that you will be
as attractive as possible for Senior Roberto.
"Really?" This seemed too good to be true.
"Of course, madam," Sr. Roberto has ordered the whole staff to see to your
every need."
Okay, I could get used to that. "Fine, what's next?"
"You will always start your day with a bath, unless you prefer to do your
exercises first."
I scrunched up my nose. I hated to exercise.
"And then, Miss Mattie, we will prepare you for your morning tryst with
Sr. Roberto. I understand that you are quite feisty and he is looking
forward to bringing you to heel."
Bringing me to heel? What was I a dog? I decided to put those thoughts
out of my mind and enjoy the pampering I had been promised. But as I got
out of bed, I wondered whether he had 'brought her to heel.' She was
kinda zaftig, way heavier than me. Is she the kind of girl Roberto liked?
Would he want me plump? No way. "Okay, how about that bath?"
Within an hour, I had been bathed, powdered, made up and my hair blown
out. I felt fabulous. She had selected some amazing black lingerie, but
I chose to wear only the sheer top and panties. I gazed at her, feeling
totally detached as she laid out my coffee and a light breakfast before
leaving.
"Don't forget to redo your lipstick when you're finished eating," she
reminded me as she left. "Sr. Roberto loves red lips. And please, put
your bra on. It's gorgeous!" As she slid out the door, she noted that,
"Sr. Roberto will be here shortly,"."
I was feeling kinda dreamy, so instead of putting on my bra right after I
finished my coffee, I took my top off and lay on the floor with my feet up
on a chair, so I could bask in the sun streaming in through the windows.
I felt like cat. A few moments later, while I was still zoned out,
Roberto knocked on the door, and like the previous night, stuck his head
in before I had a chance to answer.
I only had time to glance up before he said, "My dear, don't you look
lovely today."
"Oh!" I squeaked. He looked fabulous. Polished in that way that rich
people are and gorgeous as only he was. He came over knelt down over me,
and bent his head to kiss me gently on the lips. The sun glistened off
his hair.
"I'm delighted to see you looking so well," he nodded at me.
"Thank you," I replied shyly, shivering with delight.
"Have you thought about what we discussed last night? Are you ready to
actually behave like a proper sissy wife?"
I cringed. Reality had shattered my sweet little dream world just as
completely as a hurtling rock shatters a window. I could see his face
cloud up simply in reaction to the look on mine. Could I do it? "No," is
what I said. "Isn't there some other way?"
"You masturbated last night after I left, didn't you?"
I blushed, and looked down. How did he know?
"Ah my little sweetie, you give yourself away so easily. It was just a
guess."
I felt like a total fool while he grinned victoriously.
"Well, be that as it may, your penis will now be off limits to you until
you have learned to satisfy mine. I told you punishments can last a long
time." With that he pulled a small chastity device from his pocket.
"This is a CB 6000. You will wear it not only until you have satisfied
me, but until satisfying me brings you great pleasure."
I started to reconsider. Maybe I could suck him off.
But I was too late.
He got up and pressed the intercom by the door. "Eva, bring the ice
please, and bring Mr. Hobbs as well."
They both appeared so quickly that I knew this had been prearranged.
"Mr. Hobbs, Please help my dear Mattie to relax while Eva fits the device.
Mattie, I will see you later." With that, he turned on his heel and left.
"So," Mr. Hobbs said, "the easy way or the hard way?"
"Can I put my bra on first?"
He nodded.
Eva looked at me quizzically for a moment ant then said, "I think you can
leave now, Mr. Hobbs. Miss Mattie understands what she must do.
He looked at me to be sure she was right, gave one of his formal bows and
said. "Madam, if I can serve you again, please call on me."
His little grin made me frown, but I was happy he was leaving. I didn't
want him playing with my penis.
When he was gone, I sat down on the bed and spread my legs.
**
Later that afternoon, as I was waiting for Roberto to join me for pre-
dinner drinks, I stood glumly by the window, my penis encased in a plastic
tube, my torso encased in a lovely, though ridiculously tight black
corset. My sheer panties had a fabulous red waist band, and my new
chastity cage was clearly visible. I looked fantastic, but could not have
been less happy.
Again though, Roberto was charming and seductive. The evening was
delightful and I had never felt so feminine. The bubble burst, as I knew
it must, when he took me by the shoulders and said, "It's time." I don't
want to punish you anymore, so just fulfill your responsibilities and
let's have a lovely relationship for the next year."
"Will you let me out if I do it?" I asked, pointing to my caged cock.
"Not right away," he responded lightly. But I won't spank you."
"Oh God!"
So I did it - though not very well, apparently. Roberto was not at all
happy with my lack of enthusiasm.
"You have much to learn, my sweet," he said as I wiped my mouth with the
back of my hand. I'm not going to force you, but I am going to supply
some lessons to help you understand what you must do.
It was corsets from then on, and that horrid chastity device only came off
when I was bathing. To make sure I didn't touch myself, Eva gently tied
my wrists behind my back while she washed me. She was treating me with
the upmost deference and couldn't have been any more attentive, but I was
imprisoned nonetheless.
"I'm growing tired of your lack of enthusiasm," Roberto exclaimed after
another not so great blow job. I have given you everything: a lovely
home, a maid who attends to your every need, beautiful clothes, yet you
still resist. I'm beginning to believe you have no intention of living up
to our agreement. Your training is going to become more intense, and if
you don't learn your lesson this time..."
After another bare-assed spanking, he left me to consider what "intense"
might mean.
***
The very next day they turned me into a household pet. I was fitted with
a collar and was not allowed to stand or talk. I was whipped when I tried
to do either, so I learned fast. If I wanted something I had to get
attention by barking or crawling up to the person and, well, panting and
hanging my tongue out and begging. To beg, I sat back on my legs and
lifted my hands to face level with my wrists flopping forward. I had
never felt so demeaned in my entire life.
My trainer worked me hard to ensure my behavior was sufficiently doggie-
like. She was merciless with her crop correcting every mistake I made,
and any human behavioral traits were quickly disappearing as I did
whatever it took to avoid that crop. Pain had never been my thing. At
first, she led me around on a leash, but it didn't take long for me to
learn the hand commands she used, and I would sit, stay, lie down and heel
at her whim.
She even trained me to fetch. She had withheld dinner and then breakfast.
I barked, begged and panted furiously by my empty bowl. She hushed me. A
few hours later, with my stomach growling, my training began. She ordered
me to her side with a hand command, left hand down and in a fist, and then
tossed a leather doggie bone across the room. I looked at it and then
looked up at her. She pointed to it, but I refused to move.
"Go on, Mattie, fetch," she said. Instead I lay down on the floor. This
was just too much. Then she held out her hand. It contained a savory-
smelling piece of what looked like tender beef. I started to reach for it
with my mouth, but she withdrew her hand and said, "Fetch, Mattie."
I started to sit up to beg, but then decided that begging was even more
demeaning than learning to fetch. I got the stupid toy, picked it up in
my mouth and brought it back to her, and looking pleadingly into her eyes,
dropped it at her feet.
That little piece of meat was really delicious! I was able to satisfy my
hunger after just 15 minutes of that stupid game. But I got no dinner.
The next day, again no breakfast, so the treats became more important, but
also intermittent, and I worked all the harder to get them. Eventually
there were no treats and I was simply expected to fetch at her command.
When I balked at playing the game, she just smiled and I got no dinner.
Lesson learned. I did what I was supposed to so I could eat.
I was fed on the floor and could only use my hands to hold the outside of
the bowl so it didn't slip away from me as I tried to eat its contents.
My meals were actually quite good, prepared by our chef and then cut into
baby-sized pieces so I could eat them without using my hands.
Before every meal, there was dildo training. I was basically being taught
to suck cock and had to satisfy my mistress, who wore it in a harness
around her groin, with increasingly improved performances before I was
allowed to eat. I was expected to be enthusiastic, make all kinds of sexy
noises and perform different movements of my head and neck that I just
knew any man would adore.
Worst of all, however, was that I was led outside twice a day to go to the
bathroom. I had to do it on a special part of the lawn set aside just for
that. Any of the staff who happened to be around would stop and watch,
subjecting me to levels of humiliation I had never even imagined. Lifting
my leg to pee and squatting to move my bowels almost made me cry.
Roberto apparently still wanted me to look beautiful, however, so Eva
bathed and groomed me every day, putting my hair in two bunches over my
ears so they sort of looked like doggie ears. One night, as she brushed
my hair, Eva said, "You will be very cute tomorrow, you'll see. She
twirled her hand in the sign for me to roll over onto my back. As I lay
there, my hands up and bent forward like a dog and my legs spread, she
tickled my tummy. Despite myself, I laughed.
Still, I wished that Pamela would come and rescue me. This was just too
much to bear.
The following day, she did rescue me, though only not in a way I could
have anticipated. After grooming me, Eva shaped my hair into two tight
bunches, and then Mr. Hobbs, my trainer, and someone I had never seen
before, wrapped my arms and legs in some kind of fabric tape so that my
forearms were pulled all the way to my biceps and my calves were pulled
tight against the backs of my thighs. I could only get around by walking
on my knees and elbows, which were thankfully padded. Then, as I screamed
and protested, a circle gag was pushed into my mouth and tied behind my
head. I couldn't talk, but my tongue could be stuck out through the hole.
I feared what might be stuck in.
My trainer said, "This is an important day for you, and I want your
behavior to be perfect. Little doggies obey, or else." She glared at me,
and I shivered in fear. I was so scared I even whimpered. That drew a
sadistic laugh from her. She then began to put me through my paces, and
when I momentarily balked, she whipped my pantied ass. And it wasn't even
breakfast time yet. I was finally allowed to drink some milk from my
bowl, which, because of the gag was almost impossible.
Not long after breakfast, Pamela showed up. She looked unbelievable. Her
blonde hair was flowing behind her as she strutted into the room wearing
the sexiest, barely there outfit I had ever seen. I would have been
ecstatic, but she had my trainer's crop by her side and a very determined
look on her face. So instead of being full of lust, I began to tremble
with fear. The trainer handed her my leash, and she jerked it sharply,
leading me outside. "Go ahead, do your stuff," she ordered as we reached
my designated toilet area.
The last thing I wanted to do was go in front of her, but she was adamant.
"This is your last chance till evening," she reminded me.
I couldn't lift my leg, so I just let go with a stream of pee between
them, next to the designated tree.
When I had finished, she startled me with a hard lash from her crop.
"Now, that I've got your attention, let me see how well trained you are."
She put me through my paces and even though it was nearly impossible to
move, I hurried to complete each of her commands and finally sat in front
of her begging once I had brought my leather bone and dropped it at her
feet.
"What IS the matter with you," she shouted as she looked down at me,
slapping the crop loudly against her palm. She gave me the command to heel
and I followed along by her left hand as she started to walk around the
yard.
Suddenly, she turned, took a step to my side and slashed the crop onto my
ass. The panties offered no protection.
"Ah!" I gurgled out through my ring gag.
"Do you want to lose everything?"
The whip bit into the sole of my right foot. "Uh!"
"Roberto is talking about cancelling the contract. Do you know what that
means? If he does, I'll castrate you myself, and throw you out on your
skinny ass. Do you understand?"
"Ah, ah, ah, ah!" She punctuated her threat with a wicked series of
cracking lashes right across my butt. By the time she stopped, I was
crying uncontrollably, and almost choking because of the gag.
"Look at me she shouted." I immediately raised my head to look into her
face. "I've convinced him to give you another chance, and if you blow it
this time, you're dead meat. Do you understand?" The next time you see
him, you better convince him you want to be his sexy little plaything, or
you'll be working the streets. She slashed my ass again, threw the crop
in front of me and stalked out. I stood there, absolutely boggled by the
sway of her ass, but unable to do anything but sob.
That night, after I had been unwrapped, bathed, and fed, I did a lot of
thinking. It was pretty obvious that Pamela and Roberto were dead serious
about this contract. Roberto was willing to let me live a life of luxury
if only I would have sex with him. On the other hand, he had no qualms
about the cruelest punishments when I resisted.
Pamela was even scarier.
And I didn't even know why I was resisting. At first I had done it
because... well, because I thought I was still supposed to be a man!
Fight against anyone who tried to deman me. Avoid at all costs being
emasculated. Not let anyone put me down, or even worse, humiliate me. I
couldn?t let anyone know I was a sissy!
But, really, that was pretty stupid. I had thought I was female since I
was a kid. The day I discovered my mother's lingerie was still etched in
my mind as one of total joy. I played with it for years. And over the
past couple of years, finally with Pamela's support, I had done everything
I could to become a woman.
And what did it mean to be a man anyway? I guess it was some kind of core
identity thing that was supposed to come from having a Y chromosome. But
I didn't have that core identity. My core identity was female! It' not
just that I dressed like a woman, I reveled in it. It's not just that I
had classic female tendencies, like nurturing, nest building, and wanting
to help out, I loved doing those things. Maybe I was a ridiculously old-
fashioned stereotype, but I longed to be romantic, yielding, and demure.
I wanted to be playful, not commanding, vulnerable, not forceful,
seductive and charming and powerful and demanding. Behaving that way, at
least in my fantasies, made me feel authentic; they made me feel like me.
A man couldn't be like that.
What's more, I realized, as much as I liked sex with Pamela, and I loved
it so, Roberto made me quiver inside when he looked into my eyes and
utterly melt when he kissed me. His hard, hot thighs rippling under my
belly when he spanked me almost sent me through the roof, even though I
hated being spanked.
That's what I thought about curled in my wicker doggie bed, which had
purposefully been place at the foot of the soft, luxurious canopied bed I
had been sleeping in. They tied my leash to the bed frame so I couldn't
get up. With the real Tiffany lamps on either night stand shedding a warm
glow, I imagined myself on my knees is front of him, putting my little
hands, with their fuck-me red nails, on his thighs to pull myself up to
his crotch. Oh! I started to get hard inside my cage.
Fuck! What I wouldn't give to be out of my chastity! I forced my
breathing to slow and let my heart calm down. Getting hard inside my
little prison was not a good idea.
But my fantasy wouldn't go away. As I imagined raising myself up high
enough to see his cock, I realized that I had already sucked on it. That
just wasn't the issue anymore. I was already a cocksucker.
Me. A cocksucker. Was that some kind of big deal? I knew it was
supposed to be, but it didn't seem that way. No. Right now I was trying
to remember why the thought had bothered me so. If the thought of my
hands on Roberto's thighs had made my imprisoned penis start to harden,
the thought of his remarkable cock made me salivate! I couldn't get it
out of my mind. I wanted more of it. Lots more of it!
I realized that I had been a fool. I had allowed the little shred of
false male pride that remained within me to dominate my behavior even
though I no longer actually thought of myself as a man or even objected to
having sex with Roberto. If I was going to be a woman, having a sex with
a man was normal. And, he was actually much more attentive and passionate
than Pamela had ever been.
Right then, I made up my mind to give him what he wanted and to want it
myself. It had been my dream to become a woman that had led me here in the
first place, so why not fully express my womanly self?
I fell asleep longing to give Roberto the blow job he deserved for taking
me into his life.
The next day, my hair was again tied up in two tight bunches on top of my
head and a large sparkly jewel was put in each bunch. I was made up to
look both innocent and hot. I was led into the kitchen, where Roberto was
waiting for me. "Let's see what you have learned," he said, before
directing me using only the hand commands.
"Very good," he finally noted and he placed a bowl of milk in front of me.
I looked up at him imploringly and twisted my body into the sexiest shape
I could manage to try to convey my thanks. I did everything I could to
look sexy and beg for forgiveness at the same time.
I couldn't take it anymore. If he wouldn't give me another chance, I knew
my I was headed for a bad ending. He looked down on me for a few moments
and then smiled. He turned to go sit in a comfortable chair by a large
window overlooking his gardens and signaled me to lie by his feet.
"Now," he went on after I had settled in and was looking up at him
expectantly, my tongue hanging out as far as I could get it to go. "Are
you ready to cooperate?"
I nodded eagerly.
"Eva," he called. When she appeared a moment later, he said, "Please make
Mattie beautiful for me." And then he glanced down at me and smiled
warmly, "And for her."
My heart almost melted.
Eva, took me back to my room, undressed me, gave me a quick bath and
dressed me again in new lingerie. I loved the way the sheer cups of the
bra gently held my small breasts and made them look sooo sexy, even though
they were small.
"Something has changed,? she said. ?I can see it in your eyes.?
I nodded shyly, and she took my hand, walked me to the door and opened it.
?In you go,? she said, ?to a better life.?
I entered timidly, but as soon as Roberto saw me he smiled. "Come, my
dear. Sit by me." He again pointed to the floor by his feet.
I curled my legs under, settled down and looked up at him expectantly.
"You know what to do," he said in a kindly voice as he unbuttoned his
jeans and opened his fly.
Yes, I did know what to do. It wasn't just that I wanted to put an end to
this humiliating episode that motivated me to jump up, bury my head in his
crotch and dive onto his cock, sucking him off with as much enthusiasm and
skill as I could muster. I wanted to show him that I was ready to live up
to my part of our bargain. I wanted to show him in no uncertain terms that
I finally understood that this was something I had to do to become the
woman I had dreamed of becoming. I wanted to show him that I could be
good wife or consort or trophy sissy or whatever he wanted me to be. I
wanted him to know that I wanted to stay with him.
The humiliation of being the family pet and the fear of Pamela's threat
were now irrelevant, although they had been an important part of my
lessons. I needed to do this for myself because I knew I would regret it
forever if I threw away the chance to live the life of a rich, adored
woman just because I had some strange hang up about having sex with a man.
"Wonderful," he boomed, after I had finished licking him clean. "I'm so
pleased you have reconsidered your position. To celebrate, I have tickets
for the opera tomorrow night. You will look ravishing and I shall adore
you."
I almost fainted with joy.
A night at the opera
Eva awoke me the following morning. "Mistress, it is so nice to see you
are back. I so hated the last couple of weeks.
"Me too," I agreed glumly. "I was a fool."
"No matter," she agreed. "You will love today."
She was right. I spent it at the spa for reparative therapy. Boy did I
need it. I was massaged, steamed, cooled, anointed with oils,
depilitated, polished, painted, and made up. When I left, I felt like a
million bucks, and after a nap, was ready for my big evening out with
Roberto. I had vowed to myself that I would make it perfectly clear to
him that I adored him so much that he would never want to let me go.
It truly was a dreamy evening and I loved my exquisitely tight dress and
hair (well, wig actually) and especially my lingerie. It took a lot of
padding to make everything look right, but I was ravishing and reveled in
my over the top femininity. I posed for Roberto as we shared drinks
before getting ready to go out to dinner. While we were out, I played the
part of the trophy wife with all my heart, and hung on Roberto's arm and
exuded as much enthusiasm as I could muster.
When we got home, Eva undressed me and gave me a perfumed "douche" so I
would be ready for Roberto. She then helped me into a sheer black teddie
and let my real hair down. I was longer than it had ever been, and was
sleek and shiny. I had gone into my bathroom to admire myself in the
large mirror when all of a sudden, Roberto appeared. I looked back at him
over my shoulder, embarrassed to have been caught like that, but he gave
me a huge smile, held out his hand, and said, "Your bed or mine?"
He was attentive and passionate, and so was I, for his blow job at least.
I allowed him to seduce me, and once he had my clothes off, I was all over
him kissing, licking, rubbing and sucking. I did my best to suck his cock
right off his body. He groaned with pleasure when he came deep into my
throat.
But when he wanted to enter me, I became stiff and anxious. I desperately
wanted to please him, but I couldn't help myself. I felt more like a
middle schooler, who was losing her virginity even though she wasn't sure
she wanted to, than a fully grown woman exploring the sensual pleasures of
sex with her lover. I guess it didn't help that he wanted to take me as I
kneeled backwards on a chair. It wasn't terribly romantic, but I knew
that with my black lingerie and 5 inch fuck-me pumps, that I must have
been a sexy sight indeed.
I didn't know what to do or think. His cock, which seemed so utterly
desirable in mouth, seemed like an unwelcome intrusion in my... pussy?
No. I couldn't yet grapple with that. It was in my ass and it all seemed
wrong.
All in all, it was not a pleasant experience. I was disappointed in
myself and Roberto was not pleased with me.
"I'm so sorry," I begged him, in tears. I want to please you, but I'm
scared. Please don't punish me again. I'll do anything." I grabbed his
cock and started licking it.
He seemed genuinely moved. "That's very touching," he said, cupping my
cheek. Then he let out a big sigh, removed his semi-hard penis from my
mouth and stood up. "You need more training," is all he said before he
turned and left.
'What now?' I thought.
**
The next day I was introduced to a new trainer. It was a cock mounted on
a chair. It didn't take a genius to figure out what my training would
consist of.
As I stood there staring at it, a 30 something woman wiggled her way into
the room. She was tall, handsome rather than pretty, blonde, busty, and
had slim hips and a tight ass. After a moment, I realized she was, or
more to the point, had been, a guy.
"Mattie, honey, I'm Tiffany." Her voice was breathy and hoarse, and her
smile gigantic. As she moved in to give me air kisses on both cheeks, she
said. "I hope we can become good friends."
"Uh, I do too," I blurted out, not sure what to make of her.
"You're so pretty," she exclaimed, brushing my cheek with her hand. "I
wish I had your looks."
I looked down and blushed. I could feel the warmth suffuse my face. I
took a breath and looked up. "Thank you," I replied bashfully. Then,
nodding at the chair, I asked, "Are you going to help me learn to use
that?"
"That's right honey. I may not have your looks, but I am a great lay. Men
like Roberto pay top dollar for me."
I sighed.
A great lay. If I was lucky, that would be my future.
How many times had I heard a guy brag about what a "great lay," his date
had been? But that's exactly what I needed to become. I hadn't thought
of it like that before, but now it was perfectly clear. For a brief
moment I thought that being an accountant wouldn't have been so bad,
though that option didn't actually exist anymore. No, my future was a
great lay and a world class cocksucker, or else. I unconsciously licked
my lips at the thought.
And then it clicked into place. Pamela, I realized, wasn't that great a
lay. She was sexy as hell, but she was too selfish and narcissistic. I
had been the one who supplied the energy that kept our sex life going. She
had said it herself just before she shipped me off to Roberto - I was a
male slut.
My eyelids blinked rapidly a few times as I understood a new reality.
What man wouldn't want to be with a woman who had my sexual energy? What
I needed now were some new skills ? retraining I was unlikely to get at my
local community college, but for which I now had a private tutor. I
already wanted to please Roberto; I just needed to learn how.
"I'm ready, I said to Tiffany. I don't want you to leave until I'm as
good as you. "
She, smiled, took me by the hand, and led me over to the chair. "Let me
see you suck it; I hear you're pretty good at that. No matter, really, by
the time we're done, you'll not only be a great cocksucker, but have men
begging for your ass. You'll see."
I did learn a lot from that chair, and at the end of each day, Tiffany
fucked me, critiquing my every move as she plunged her own somewhat dainty
cock into me. Then we switched places and I got to fuck her as she again
instructed me on the fine art of using a cock to give pleasure. When we
were done, she shoved a silvery butt plug into my ever loosening anus.
Ten days later, my ass easily accommodated both her cock and the one
mounted on the chair (or the wall or floor), and I was beginning to
understand how to use my body to give both me and my lover pleasure.
As a celebration, Tiffany and I shared champagne, and then we shared a
farewell fuck. I tried to show her everything I had learned. While I may
not have been a pro yet, I was learning the joys of anal sex and was ready
to show off my new skills to Roberto. Because of my progress, she let me
out of my chastity device right before she left, but had me insert a
larger butt plug. "Roberto is larger than I am. This will help you be
comfortable when he takes you."
By now, it didn't actually feel weird to have that thing up my ass, and I
knew it was for my own good. I clenched my sphincter around it and wiggled
my butt.
**
The next night Eva, cleaned me with two douches, pampered me with oils and
perfumes and soothed me with a gentle massage. She dressed me and made me
look beautiful, producing yet another fabulous bra and panty set, advising
me that, "Your master wants to see his lovely concubine tonight."
Concubine? Maybe I liked that. It sounded sexy; being a wife was so
mundane. What did it mean though? I didn't dwell on it and instead
simply let my mind go blank as I draped myself over my favorite love seat
and waited for Roberto.
That evening I did everything I could to please him. I was attentive,
loving and exuberant in my sexual expression. I virtually devoured his
cock with my mouth, and when he mounted me, I thrust back at him and
twisted and turned and moaned in ecstasy. Actually, I had so much fun I
couldn't remember why I had resisted for so long.
He took me three times, and by the end I was so exhausted and disheveled
and sore that I could barely think straight. For the last, I just lay
back on his bed and grabbed my ankles to stretch my legs apart as he
pounded away, each thrust pushing an exhausted squeal from my lips. He had
utterly taken me.
When he came, I wrapped myself around him and held on tight as we drifted
off to sleep.
**
That night changed everything. Finally, months after arriving at his
home, Roberto and I had our honeymoon. He was a voracious lover and I was
his plaything. He showered me with wonderful lingerie and I sashayed about
like the Queen of Sheba. Some days he wanted me in my chastity, other
times I wore one of my now large collection of butt plugs. But no matter
what I wore, I lavished all my attention on him and savored his cock no
matter how he wanted to offer it to me. I thought I was starting to fall
in love.
The contract hardly mattered any more. All that mattered was Roberto and
what he wanted from me and what I could give him. He gave me so much in
return. Each time he entered me, I just stared into his eyes thinking,
'why did I fight this for so long?' One of the things I loved was that he
liked to play with my penis. It was always free now during sex, and even
though it was largely my job to pleasure him, he never failed to make me
cum.
**
Once we had become comfortable with each other, Roberto started to show me
off. I must admit that I surprised myself by becoming quite the little
exhibitionist. The mousy little librarian who had set out from home all
the months ago in her conservative Talbot's outfit, now strutted around in
clingy rayon designer gowns and too short cocktail dresses with towering
heels. I was aroused and energized by the attention I received from
others and reveled in being sexy and flirtatious. By the end of the
evening, I was usually so aroused that I simply pounced on Roberto and
devoured him. When we were home alone, I indulged myself and Roberto with
one lingerie outfit after another. It seemed I hardly ever wore clothes
except when we went out or had guests. Even though my breasts were still
small, I loved showing them off.
One evening I was staring out the window waiting for Roberto and massaging
my nipples. I had come to a decision and dressed in a sheer green dress
with no bra as part of my plan to convince Roberto to get me larger
breasts. Eva pointed out to me, however, that if I took panties off my
panties as well, my penis would also be visible hanging down between my
legs. So when I heard Roberto come upstairs, I moved to the window so
that the waning light could illuminate me. When Roberto came in the room,
he simply gasped with pleasure.
"My love," he declared. "You are the most luscious thing I have ever
seen."
Smiling with joy from his compliment, I turned slowly, pausing half way
around so the sun highlighted my breasts. I brought my hands up to
massage them as I finished the turn to fully face him.
"Come love," I offered, my voice husky, "Give me a kiss and then let's
make love." He didn't need any convincing.
As we lay in the afterglow of good sex, I broached the subject of breast
implants. "Roberto, my love, do you wish I had bigger tits?" I pulled
his hand up and placed it on my breast. "I do," I went on, suddenly
worried that he might not.
"You know I want you to remain a boy," he replied, bending his head to
suckle on a nipple, "a lovely, feminine boy. So if bigger breasts are
what you want, then you shall have them." He smiled and again ducked his
head to suckle the other breast. "I'm sure I can find a way to enjoy them
no matter no matter what size they are."
I must admit that at this point I was a little confused. Although I had
always planned to go back to being a man after our year was up, I was now
so much embedded with and so much in love with my femininity, that the
idea of staying as a woman forever was the only thing that made sense.
And I had just convinced my lover to buy me bigger breasts. By now, the
only real options were to be a very girly boy or a girl, period. So I
just put the whole thing out of my mind because it hurt my brain to think
about it. 'I'll cross that bridge when I come to it,' I decided before
reaching over to kiss Roberto and thank him for his offer.
"And we will celebrate once you are healed after your surgery. I will
throw a party and invite my friends. It will be your coming out party;
you will be my little debutante for the evening. I shall be so proud of
you!"
And a month later, the night of the party had arrived. It was a small,
but lavish affair (really, all our parties were lavish). Even Pamela was
there, though I frowned when I saw the young man she was with. At first I
wore a rather modest, though ridiculously expensive dress. After greeting
all the guests, I disappeared to change. Roberto called for everyone's
attention, and announced my return.
"My friends, my lovely wife Mattie have just acquired something she is
very proud of and that I adore. We would like to share them with you."
I pranced out onto the patio with a newly acquired model's strut. I
walked to the end, paused to pose, and then turned to come back to
Roberto's side. The crowd broke out into applause. As well they should
have. The top of my dress merely outlined my breasts, highlighting them
for all to see, and the see-through skirt emphasized my little thong. I
stood by Roberto, posing while trying to keep my heart from beating its
way out of my chest. I couldn't believe what I was doing! What must they
think? It didn't really matter because Roberto loved it, and that's all I
really cared about. I felt soooo feminine I thought I would die. Pamela
looked awe-struck.
After that, it became standard for me to wear provocative clothes that
often showed off my breasts. People looked forward to my next outfit,
enjoying my brazen exhibitionism even as I was trying to figure out where
the hell it had come from.
I was really eating up t