When they woke up the following morning they made love yet
again. She was silky softness everywhere, under his arms, against
him, surrounding him, and her thighs were warm and moist and
sticky, and her pussy was still slick with their juices from the
previous night. He hardened yet again as he felt her pressing
against him, and then this time he mounted her and plunged into
her, and came into her yet again.
When they finished, she seemed pleased. Then she commented
that there was one more thing she wanted him to do for her, and
then they could see about breakfast,
"What's that?" he asked, stretching like an enormous cat. He
had never felt better! He rolled off and looked at her. She was
stark naked. She wore her skin the way other women wore leotards,
as if her body was its own sufficient clothing. He came suddenly
aware that he hadn't himself undressed the night before. His slip
was now around his waist, and his bra had ridden up above his the
nipples. It all seemed a little silly by the morning's light.
But she had wanted him to wear them. For some reason the idea now
stirred his loins, as if he were about to begin yet another
erection. But no, he had now altogether spent himself into her.
He stayed soft.
"This!" She suddenly reversed her body and lay down on top of
him, her legs spread wide as she slid her crotch up his chest
toward his mouth until her lower lips kissed his lips. Then she
wriggled her hips slightly, seating her pussy firmly onto his face,
his nose pressed into her anus. For a moment he couldn't breath.
Then she unlimbered her legs slightly, and he opened his mouth to
take in a great gasp of air. She clamped his mouth firmly against
her crotch.
"Kiss me, Bobbi dear, my lovely, dearest girl! Suck on me!
Clean me out, my dear, precious Bobbi! Lick me! Suck me! Drink
me!"
And once again Bob went into ecstasy, drinking her juices,
mostly his own cum, nibbling and sucking on her clit until she
spasmed. Every spasm squeezed more of his precious cum out of her
cunt into his mouth. There was quite a bit of it deep in her from
the previous night, kept fresh under her mound between her legs,
inside her beautiful rosy-lipped pussy. He licked her deep inside,
and along her slit up to her curls of hair, and down the outside of
her labia, and then inside her thighs. When she allowed he licked
the crust from her belly and hips. This time, as she pressed her
pussy into his face, then away for him to lick her more delicately,
then again pressed down, this time he was sure she came. She never
made a sound, but her whole body clenched and then relaxed into
luxurious ease while he licked her again and again, kissing gently
those folds he knew now were sparkling clean, finally taking her
little clit into his pursed lips and gently, sweetly kissing it.
Then again.
"Time for a shower," Diana said suddenly. "You first, sweet
Bobbi girl. I'll lay out your clothes for the day."
"We won't shower together?" Bob asked her, a little
disappointed. He wanted to run his hands over her skin, and
between her legs, while she was all slick, wet and glistening.
"Another time, my dear girl. You first."
While Bob showered he kept grinning to himself. He felt so
good! Finally, he had gotten into her, and obviously she loved it.
But he wondered how far she meant to carry this "dear girl" thing.
He had promised, he remembered vaguely, to wear a bra and slip
today for her. So he would. And under a dress. Well, all right,
a dress. But this weekend only. All right. But then while they
were making love last night, in that so delicious moment when he
had yielded all of his soul and will to her, he had promised her
"from now on." He was her girl. What did that mean, from now on?
It meant all the time. Not just this weekend. Stretched out taut
in the ecstasy of coming, he had promised her. He had wanted to
promise her. God, how he had wanted it! Now he wasn't sure how to
deal with "from now on."
Maybe he could ignore it. He was a man. After last night and
this morning she could have no doubt of that! He decided to ask
her, casually, how she planned to have him be her girl and yet
remain her man. A man is a man, after all. He knew she couldn't
really be serious, calling him a girl. So he hadn't really
promised her anything. There was no real problem here.
But when he got back to his bedroom, still naked, his body
squeaky clean and hairless as a baby's, he was shocked!
Astonished! There in the room stood a large, stocky woman, filling
most of the space in front of Diana, who sat at ease on the edge of
the bed looking up into the woman's face and listening, then
talking, throwing her hands here and there expressively while she
talked. The woman was wearing a pale purple starched uniform of
some kind, like the kind beauty parlor operators wear, or nurses.
Bob noticed that she was listening to Diana attentively and
respectfully, every now and then nodding. Diana noticed Bob out of
the corner of her eye, completed whatever she was saying, turned to
Bob, and smiled at him.
"Bobbi my sweetheart, you adorable darling, come here. I want
you to meet Erika. Erika looks after different things for me, now
and then, and I've asked her to help me look after you now, to help
me prepare you. There's so much to do! Oh, you are going to love
being a girl, I just know it! Right now I thought you should just
see each other -- you can take the time to get acquainted later on.
That's about it for now, Erika. You might see what can be done
about breakfast before you go."
Bob was bewildered, flabbergasted! He was standing in his own
bedroom stark naked, and here was a strange woman looking him over
with a mildly attentive professional eye. He tried to cover
himself. His hands fluttered over his loins and, unaccountably,
his chest before he realized he had better just stand still on his
dignity. He finally found his voice and tried to declare his
indignation, but before a sound could come out Erika broke in and
said, "Miss Bobbi, how nice to meet you. I see you've had your
shower. Did you remember to take your enema and then your douche?"
Somehow, this seemed insulting! Bob lookled at Diana, his
lover, expecting her to intervene in such a delicately personal
matter, but Diana also seemed to be waiting for his reply.
"Erika," Bob replied, as if completing her introduction to him by
acknowledging her name, trying to grasp the initiative. "Pleased
to meet you." The two women waited patiently for this obvious
untruth to dissipate, and Bob realized he had only one more thing
to say. A moment passed in total silence. "No," he said, "I
forgot." He felt like a child asked if he had scrubbed his teeth.
"Well, shouldn't you now?" Diana asked. "Would you like Erika
to help you? Erika, would you go with Bobbi and help her clean
herself out? I'll bet with all the excitement this morning she's
even forgotten that she's still having her period, and needs to
change her tampon."
Bob suddenly realized this was true. He was still having his
period, and needed to change his tampon. No he wasn't, he tried to
tell himself. Men don't have periods. Even so, he felt like a
twelve year old . . . girl (he swallowed hard) who has been
reminded she needs lessons in personal hygiene!
"Yes Miss Diana" Erika said. "And while we're about it shall
we begin preparing Bobbi's vagina for its new responsibilities?"
"Well, no, not yet," Diana replied. "Just help her clean
herself out, then see to breakfast. I'll get dressed meanwhile.
After this weekend we'll want to move Bobbi into that spare
apartment in the your building, and then you'll be able to look
after her needs much more easily. Now that she's my special girl,
and she wants to be mine, we'll want to take especially good care
of her. She's very precious to me." Diana looked directly into
Bob's eyes, and said with no noticeable irony, "Aren't you, my
adorable girl? Aren't you? Yes. Yes, you know you want to be
mine. Don't you? Say it again. I love to hear you say it."
Bob couldn't quite grasp what was happening, and said nothing
for a moment. Erika stood there in her starched uniform and looked
at him as if preparing to move forward. "Miss Bobbi," she said.
"Shouldn't you answer?"
"Yes," Bob said, "I'm yours. I know it. I want to be yours,
I know that too!"
And for some reason the naked man felt utterly helpless.
Unaccountably, unexpectedly, he fell to his knees in the doorway,
and realized he had started to cry. It was as if somehow his old
life was over. Somehow he was saying a sorrowful goodbye to his
old self. For her! Diana came forward and knelt down, and cradled
his head in her hands, and comforted him.
"There, there, Bobbi" she said. "You'll love it. It'll be
beautiful. I promise you, this will be the loveliest thing that
will ever happen to you. But just hug me now, and cry as long as
you want to."
Stark naked and on his knees, Bob hugged her and sobbed, at
first uncontrollably, then in spasms and short bursts of tears,
then looking up to her in a kind of hopeful helplessness, gasping
now and again. Diana stroked his hair and his back, and hugged him
gently, looking over his shoulder at the wall, or at Nurse Erika,
who waited patiently for Bobbi to compose herself, at least
sufficiently to complete her toilet, her enema and douche, and to
change her tampon.
*********************
That day Bob wore all day the slip and bra he'd promised to
wear, under the dress he'd somehow promised he'd wear, a simple
purple wool with a flared collar. And panties. Then in the
afternoon another blouse, a full skirt, and a cardigan sweater.
From her large suitcases Diana fitted him out first with rather
plain three inch heels, then later in the day with four inch heels.
By mid-afternoon the wobble in his walk had disappeared and had
become a slight sway in his hips, and Diana decreed they could go
shopping. Bob was still so demoralized he raised no objection at
all, though this was his first time out in daylight while dressed
in women's clothing. He felt numb. He had no choice but to trust
her judgement that he was unmistakeably feminine, and to seek
comfort in her reassuring smile. She told him to use his pale
lipstick and only a little mascara, so he did, surprising himself
that after last night it went on so easily.
They walked into an upscale store where Diana was evidently
known, to judge by the way two saleswomen immediately came forward
to attend to her, and by their deferential smiles when Diana
introduced them to Bobbi. She then bought Bobbi a really stunning
dress, a draped red silk, sleeveless, beltless, flowing down his
figure and touching each of his hip bones on its way nearly to his
ankles.
"This style's just coming in," she commented. "It's perfect
for thin women like you. Dignified but still somehow provocative.
Sometimes you'll want to wear shiny micro-minis for stepping out,
but mostly these I think. We'll keep you thin this way, though I
think that after a while you'll be getting a little more plump here
and there, where it matters." He didn't understand what she meant
and suspected he'd better not ask. Two less dramatic dresses, fit
for posh luncheons but simple enough for every day, and they were
off to buy other things. "Remember this store when you're shopping
on your own," Diana told Bob as they were leaving. "They have
lovely things, and these two women will always take good care of
you." Bob nodded. Again he didn't dare ask what she meant, nor
ask himself how he really felt about it. He'd wait for the right
moment. He couldn't risk angering her, maybe losing her again.
Before returning home Diana stopped with him at a beauty
salon. There they both had their nails done, until Bob's fingers
extended a half-inch longer than they'd been, his nails a
near-natural pink, and he saw as he curled them that they seemed
almost graceful. Then she had Bob's hair lightened just a touch,
and trimmed so it seemed to fall gracefully onto his neck of its
own will, even without rollers. When the beautician pierced one of
his ears he worried how far this thing of Diana's would go before
it retreated, but he thought it ill-mannered and pointless to
object to his other ear also being pierced. By now he was
altogether accustomed to being thought a girl by everyone, and no
longer feared exposure. Diana gave him another tranquillizer pill,
but told him as she handed it to him that he hardly needed it.
"I'm so proud of you dear," she said that evening as they set
out for another restaurant. "You're just lovely. And learning so
quickly!"
He did look smashing when they went out that night, wearing
his new red dress and matching shoes -- four inch heels this time
-- and carrying a red clutch purse, with litttle diamond studs in
his ears, his hair beautifully set in the salon, and wearing what
Diana assured him was her own favorite real diamond necklace.
Relaxing, he realized that this could even be fun. His clothes
were lighter than his usual suits, and floated on him. His bra and
his panty girdle and stockings hugged him intimately, as if
affectionately. He loved feeling hugged. As the waiter seated the
two of them, Diana commented that he seemed positively radiant. He
really did. He didn't know why.
Except that he now felt prettier, the evening went like their
first, was it only the previous night? This time it happened that
two men across the room sent a waiter over to them with a bottle of
very fine wine, and an inquiry whether they would like company.
Diana looked up delighted, but Bob felt a sudden pang of terror.
He watched her silently, horrified she might accept. But she said
to him, "Don't worry, love. I told you, you're mine." She looked
over at the men, and smiled at them, and dipped her head and raised
her hands regretfully, as if to say "We'd love to, but . . .
circumstances . . . you know." Bob mimicked her gesture to the two
men, smiling at them, and like Diana he managed to make a charming
moue and a similarly cute shrug. He felt safe with her. She
laughed, and looked across at him affectionately. "What if I'd
said 'yes' to them? I might some day, you know." Bob had no
reply.
Later they went dancing at Sappho's, and no one approached
them at all. It was as if Diana had sent out word they were not to
be disturbed. Later still, back in Bob's apartment, they made love
again, Diana again on top of him, lifting and lowering her vagina
onto his cock while he blissed out, chanting over and over how much
she loved her darling girl. Again his sexual tension built, and at
its peak she poised herself high over him until he had completed
his catechism, confirming that he was her girl forever, that he
would always do whatever she wished. Then after an excruciating
pause she lunged down onto him and he spurted into her over and
over, near fainting in ecstasy. She asked, and he repeated that he
loved being a girl, as if a gender change had already occurred deep
in his sense of self. When he'd come into her body yet a second
time, she twisted again and immediately pressed her pussy against
his mouth, and again clamped his head between her thighs. Again he
licked her clean, swallowing gouts of his cum and her juices
together as she squeezed them out of her, orgasm by orgasm, and he
kept on slurping. It was delicious!
In the shower the next morning, cleaning himself inside and
out and douching himself, changing his tampon yet again, he
marvelled at the lengths he had gone for her, how far he had come.
As Diana requested, he applied a few small drops of perfume onto
his wrists and neck, a kind Diana assured him would cling all day
so that anyone who came near him would think of him the way she
did, as a bouquet of flowers. It didn't matter that he'd smell
flowery all day, he realized, because Diana had told him that
today, for the third day in a row, he would be wearing only
feminine clothing.
But he was now musing about a key question, wondering at first
idly, then seriously, why Diana wanted him dressed all the time as
a girl. It no longer seemed peculiar to him, but it was certainly
kinky. Was she a little afraid of men, more comfortable with one
in the aspect of a woman? No way! He felt flattered it might be
her way to misdirect her competition, other women, to steer them
away from him. But as a man he had never been overwhelmed by
hordes of designing women. Or was this her way to assure herself
he wouldn't reveal himself sooner or later to be some sort of macho
pig? She hated that kind of man, he knew, and he was glad he
wasn't one of them. But she certainly knew he wasn't one of them.
Was it her way to give him a deeper insight into the way women
feel, so he'd become more understanding of her needs and desires?
Maybe. It could also be a way for her to control him in her
absence -- the perfume he was wearing, for example, would certainly
keep him from going out on his own in male clothes when she went
out and left him to his own resources.
But that wasn't happening. She seemed to be spending the
entire weekend with him as he'd hoped she would. Maybe she was
attracted to women in some way but didn't want to admit it, and
this was how she dealt with it? Maybe she was into humiliating
men? No. She was always careful to strengthen the way he felt
when he dressed for her, to make him feel proud that he was pretty.
He was even beginning to feel deep pleasure that he could make
himself appealing in a feminine way for her, and now and then,
delighted, he felt a demure or flirtatious impulse!
He had to decide he didn't know why she wanted him dressed
this way, and in his euphoria he didn't care. Today was Sunday,
and she had allowed him stirrup pants and a frilly blouse. But
he'd found it difficult to pee while wearing pants with no fly. He
asked for and was granted permission to return to skirts, and this
time she allowed him to wear two small breast forms under his
clingy knit sweater, just enough to imply a girlish figure
underneath. He'd found he felt a little freakish without them, not
quite shaped right, and though she kept saying she preferred him
shaped as he naturally was, she was delighted when he told her he
thought his chest should hint that he had breasts underneath.
Sunday afternoon he went with her in his skirt and sweater to
look at the apartment Diana had mentioned earlier in her
conversation with Erika, It was wonderful! The building had a
burly but fatherly-looking doorman who smiled at Bob, and told him
Diana had asked him to take special care of her -- she should
freely phone down for whatever she wanted, any favor or errand at
all. The apartment itself was large, flooded with sunlight, with
a view of the river from huge living room windows high above the
traffic, and a huge pink canopied bed in the bedroom, and huge
walk-in closets.
When they stepped inside, Diana handed him the keys and told
him they were never going back to his old dingy place, not ever
again. What was there that he needed would be brought over, she
said. And none of it would be his men's clothing. The closets and
drawers here were already filled with clothes in his size, clothes
befitting the young woman he'd agreed to become. She emphasized
that last by looking straight at him again as she said it, though
her voice remained casual. He raised no objection. He wondered
when she had prepared this apartment, and felt a little flattered
that she cared so much for him, and told her so. "Bobbi," she said
to him, "You *do* love being a girl! It's obvious! So that's what
you are and that's what I want you to be from now on. You want it
too, you know it! The rent on this place is paid, and now its your
place. I want you to stop looking for work and just be yourself.
Take some time off. You can have all the fun in the world trying
out your new looks and your new life. But here is where you'll be
when I want you. Here is where I want you to be."
So from then on, there he was. That night was the nicest of
all. They went out for a pizza and a movie, nothing special, just
two girls together, chatting and giggling. Then they came home and
made love in the huge bed. Bob felt transported. As she leaned
over him, smiling, his prick buried deep inside her, he rolled his
hips to gratify her as if she were the man and he were the woman,
and he reached up and delicately wrapped his arms around her neck,
and pulled her face down to his, and kissed her closed eyelids
gently, and as she fucked him he heard his throat making a soft,
long, languorous, amorous moan, then another. He felt wonderfully
feminine, wonderfully her lover. She didn't ask him that night if
he was her darling girl. She just said it, over and over, in that
slow, sweet, dark voice that so entranced him whenever she mounted
him, as if she couldn't believe her luck and needed to reassure
herself. He kept uttering small, delicious, ecstatic squeals as
she spoke, his cock soaking itself deep inside her sweet pussy, too
enraptured to find words. They both knew he was her darling girl.
The next morning, their first in the new apartment, she patted
his cheek and told him she had to attend to things, and wouldn't be
back for a few days. She told him to wear whatever struck his
fancy in his closet, and to go anywhere to pass the time, but to
remember that he was hers, and that he needed to practice being the
girl she loved him to be. "Look how far you've come in just a few
days, my darling," she said. "While I'm away, you'll go much, much
further. Erika will see to your every need. She knows what I
want. You'll do everything she says." It was a statement, not a
request.
And he was astonished to realize it, but he had come far! A
vast distance. Last night he had felt not like a man but a woman
in love. He had crossed an invisible line in his own psyche.
Erika would look in on him and attend to things each morning, Diana
said, and she would call soon. And she hugged him, and pressed her
cheek to his, almost as if they really were girlfriends instead of
lovers. Then she was out the door.
Life in the new apartment took on its own flavor. The next
morning Erika showed up and cleaned up, and fixed his breakfast,
and saw to it that his pussy as she called it was clean,
well-douched, and gave him his tranquillizer and some shots,
medications Diana had ordered to build him up. He felt fine all
day, relaxed, even languorous. If it was one of his mornings to
soak in fragrant bath oils instead of taking a shower, Erika
prepared his bath and rubbed him with more oils afterward, and he
noticed after a few weeks that his skin was softening. Each day
she put him through his exercises, walking in high heels or holding
his arms and hands just so while bustling through the apartment.
It was as if she were a dance instructor teaching him ballet.
He read the papers, and the different women's magazines that
came in the mail almost every day. Increasingly he became
interested in hairdos and styles of makeup, because every day he
realized he would be making decisions about which were more
becoming for him. He looked carefully at the ads in magazines like
Vogue and Cosmopolitan, to see what the beautiful women there were
doing with their faces that he could emulate.
There was a beauty salon in the building, and Diana set him up
with two appointments each week. One was to set and maintain his
hair -- Diana liked it long, but it needed more lift and body, and
the beautician -- a gay man altogether uninterested in Bob's birth
gender -- was magical in the way he coaxed it to wavy fullness.
One was for his nails, complexion, and what he later learned was
electrolysis, elimination of what few hairs he had on his chin and
body. This session always finished with a rather extensive
makeover, and Bob looked so chic and well-groomed afterward that he
always went out shopping afterward -- it was a waste to carry such
an exquisite face back to his apartment, with no one to see it.
But he always looked smooth and elegant, even when out walking
casually dressed in jeans and a slouch coat. And after Erika
arranged some advanced tutorials for him in feminine movement, how
to use his hands, and also how to walk, sit, and even turn his head
like a lady, he began to look classy. It was a fun game, trying to
be a beautiful woman with so few natural endowments.
Above all, it pleased Diana. Whenever she saw him she would
comment on some new evident feminine accomplishment, and ask him
what else he had learned, and Bob would feel very proud. The dull
and mediocre Bob began to feel like a gifted and happy Bobbi,
someone very special. If he happened to wake up feeling male, as
happened now and than, he felt depressed that he was still Bob, and
he treated himself to something especially feminine to overwhelm
Bob, to remind himself that he was not Bob.
He and Diana saw each other a few times each week. They were
casual together, girlfriend and girlfriend, usually informal in
socks and sneakers and a plaid skirt, now and then more formal in
a little basic black dress she bought him, and sometimes kinky in
a leather skirt and red vest over a huge, balloon sleeved blouse.
He learned to make himself up and to move as Diana did, and he
added grace to his natural courtesy, and even a certain playful
cuteness. He looked forward to dressing for his dates with her,
because they gave him special opportunity to play with his look, to
be beautiful in a new way each time. He was her girl until they
got home. Then with unfathomable skill she rewarded him for his
willinglness to fulfill her fantasy image of him. She put her
adorable, precious girl into an erotic stupor that lasted for
hours, where all he could do was utter small squeals and plaintive
cries while she did magical things to him.
He was hopelessly enthralled. Each time they made love, she
chanted new questions at him, and he always answered "Yes! Yes!"
as he approached his climax. He scarcely noticed it when her
questions began to ask if he wanted to have breasts of his own, or
a sweet little round tush instead of a bony bottom. But after a
night when she asked him that repeatedly, and he had said "Oh, yes,
yes!" over and over, and then had come gloriously melting into her,
and had actually fainted from the exquisite intensity of it, he
noticed that the following day and from then on, Erika gave him
different kinds of shots, in his tush, and each morning a huge pill
as well as a tranquillizer.
Diana had taken to calling him "Bobbi" that first evening they
went out together as girlfriends, but he didn't know how his new
name was spelled until one morning she sent him flowers with a card
explaining why -- she had made a carelessly abrupt remark to him
the night before, and had hurt his feelings. The more feminine he
felt, the more in touch with his feelings, the more easily he felt
hurt. She respected him all the more for that, she wrote in her
note to "Bobbi". He accepted her apology and sent her back a note
(though no flowers), also signed "Bobbi." And that is what, with
each date and each passing week, he increasingly became.
One evening when he'd tried especially hard to be pretty for
her, she complimented him when he opened the door and she saw how
pretty he had made himself, and he glowed, and without thinking
curtsied for her, and said, "Thank you kind sir!" Then he wondered
why he'd said that. She was as always dressed in stylish but
distinctly feminine clothes, so there was no question of her
gender. Maybe because whenever they were together, she invariably
took charge?
Diana took due note that it meant he was a heterosexual man
beginning to think of himself as a heterosexual woman. At dinner
that night, as the two of them sat in a quiet and elegant little
restaurant -- ourageously expensive, but she always seemed to have
money enough -- she began the next phase of her assault on his mind
and heart.
"Bobbi," Diana said, "have you ever wondered whether we should
take up one of these offers gentlemen are always making, what would
happen if we did?"
Bobbi enjoyed his femininity. It was not merely a way to
feel, it was erotic, because of the way Diana tended to treat him
when he was dressed. He loved everything about it. But to cope
with a man was something else again. He felt faintly repelled.
"No," he said. "I don't want it. I've never wanted it. I
wouldn't like it. I wouldn't know what to do."
"Now Bobbi," Diana said as their salad course arrived, "Some
of those statements don't chime with others. You can't know if
you'd like it until you've tried it. And not wanting it is
different from not knowing what to do. Every girl knows what to
do. It's instinctive. Mostly, it's let the man do what he wants
to do."
Bob felt somehow driven back to a second line of defense.
"Diana, I'm not a girl."
"You're my girl," Diana told him in a tone that allowed no
disagreement whatsoever. He was her possession, her tone of voice
told him, and she did with him what she pleased. "A girl who has
never had any experience of men. A virgin. So far."
And then she added, as if it were a casual afterthought,
"We'll want to change that, I suppose, won't we? Girls do become
women."
Bob just sat there, petrified with terror. Diana saw she
might have said too much, and eased off a little.
"Don't worry, darling. I don't mean now. It's that your
sense of yourself as a woman is incomplete while you're still a
virgin. We'll do some new things starting tomorrow. That's all."
"All right," Bob got out. He was so overwhelmingly relieved,
he scarcely noticed that was still a little apprehensive.
But the next morning when he woke up Diana's comment came back
to him. Was this the way he wanted to go? No. The idea of
intimacy with a man, those hairy, muscular animals! A guy?! How
do women do it? How can they want to? Why would they want to
attract that kind of person?
Fully his former self for the first time in weeks, Bob decided
that enough was enough. He hated to, but he'd leave. He put on
jeans and a simple Oxford shirt, no one would notice it buttoned
the wrong way, and slipped moccasins on his feet, no one would
notice they were cut rather low and graceful, and he resolved to
wear no make up at all. Only a little natural shade on his lips,
and a touch of eye liner. A girl needs to look minimally decent.
He took down a flowered carryall, and was wondering which of his
pretty undies to pack to take with him when Erika came in. So he
asked her advice. In reply, she gave him double that day's dosage
of tranquillizers. He spent the day dreamy, and by the evening
when Diana arrived his mood had changed. He'd become curious what
"new things" Diana had in mind.
Diana introduced Bob to "men" that night, that is, to
vibrators and dildoes. First she pleasured herself with a six
inch, pink, cock-shaped vibrator while he watched her, a little
jealous, and as it came out of her dripping with her fluids she
held it out for him to lick, suck, tongue, and then mouth sweetly.
She smiled and fed it to him head first as if it were a lollypop
held out to a baby, her own mouth partly open, her teeth slightly
clenched, her eyelids watchful and hooded. Before the evening
ended he had learned how to deep-throat it, to swallow when he felt
his gag reflex rising. She held it out playfully and asked him to
lunge at it like a puppy, to take it in his mouth and face fuck
himself with it. He obliged.
On their next date she taught him how to use his throat like
a vagina with a ten inch vibrator, the way she'd first learned to
do it in college when she'd wanted to know everything at first
hand. She'd never ask him to do anything she hadn't done, she
assured him, so he could scarcely object when she'd turn to him
still breathing heavily from her own vibrator-induced orgasm and
say, "Your turn now, sweetheart." She strapped it onto her mound
so it rose in proud, permanent erection from her crotch. Then
thereafter each night of lovemaking began with Bobbi lovingly,
affectionately, cock sucking a penis-shaped vibrator, licking,
sucking, slurping, and deep throating it while kneeling before her
while she stood legs apart, hands on hips, looking down
magisterially at his bobbing head. Or sometimes she'd sit on the
ruffled slipper chair in Bobbi's bedroom while Bobbi sank to his
knees in front of her, kissed the tip of her dildo to salute it,
and then worked it tirelessly with his mouth and throat, while she
rested a comforting hand on his carefully coiffed head.
After only a week of this nightly routine she introduced
these instruments to his pristine ass, and he understood for the
first time why all those daily enemas and douches. First her
well-lubricated finger, then a small Dildo, then a larger one,
until he could take the full-sized ten inch strap-on pounding into
him. As she commented, the length didn't matter, since his rear
pussy was deeper than the longest prick ever made. It was the
thickness, and as his anus stretched she urged him to feel proud he
could accommodate it. She persisted until his prostate was
stimulated to paroxysms and he came spurting repeatedly into the
bedsheets. Soon he couldn't imagine climaxing any other way.
Whenever he saw her reaching for the strap-on with a wicked smile
on her face, his heart leaped up eagerly and his groin spasmed in
anticipation.
Not his cock, not any more. Around this time Bob found that
no matter how artfully Diana manipulated it, the flesh had grown
lazy. It no longer stiffened dependably. When she fucked him deep
he could still achieve delicious orgasms, and the thing leaked
jism, but only rarely could he enter and come inside her. "Never
mind, honey," she said, caressing his now-distended nipples,
excruciatingly tender on the soft mounds now growing out of his
chest. "It's just that you're getting to be more and more my girl,
aren't you. Well, I'll be the man now. It's my turn!"
Diana settled on one dildo of a particular size, not the
longest she ever used on Bob but one of the thickest, warm to the
touch and mouth, with a crowning purple helmet and distinctive
veins running up it. "I don't want you to become promiscuous," she
said. "I want you to feel faithful to one man." She paused, and
flashed him a wicked gleam, and added, "Mostly." Somehow he felt
good at that. They understood each other, as girls do, and men
never suspect.
That dildo became "Diana's cock." After a few times Bob
forgot to feel humiliated when she fucked him with it. Instead he
looked forward to it. It felt familiar, comfortable. All of the
other dildoes and vibrators went back into her box of tricks. He
began to feel affectionate toward it, it gave him so much pleasure,
and Diana was amused to see Bobbi kiss it with sincere passion when
he was asked to open his mouth and throat to it, or to lift his
rear pussy high to receive it. He loved it.
He took pride that he was Diana's special plaything, a soft
vessel of flesh whose bodily openings were hers to use as she
chose. His whole purpose in life now was to look pretty for her
and to prepare himself for her visits. When she chose to go out
with him, to a restaurant or a show, or dancing, he was rapturous.
Two months after his first date with Diana in a dress, he found
that little else was on his mind than making himself pretty and
demonstrating his devotion to whatever she asked of him. When he
finally asked her what was in Erika's injections, and Diana told
him "Female hormones, so you can be my smooth, round, soft, lovely
girl naturally, for the rest of your life," he only nodded. It
seemed natural enough. He adored it when her hand caressed the
exquisite erotic sensitivity of those conical nipples budded on his
swelling breasts.
A week after that Diana decided he was ready for the last
thing she wished personally to teach him, and made a few phone
calls. It started as an ordinary dinner in a small upscale
Restaurant coiled into the corner of a new downtown office
building. Two well-dressed men chatted with them at the bar while
they waited for their table, and for once Diana allowed them to
join with the two ladies. They turned out to be excellent company,
cultured, complimentary, and amusing by turns. Moreover, they
ordered different bottles of wine with each new course, and
insisted that each be finished before the next course was brought
forward.
Bob lost all recollection of dessert or of leaving the
resaurant. He awoke in the middle of the night to find himself in
bed naked, a naked man snoring into his ear, two strong hairy arms
wrapped around his chest, and what had to be a cock pressing into
the crease of his softly rounded rear end. Had the man...? Had
the man discovered....? When he got up to use the bathroom, he
found Diana sleeping in the spare bedroom with another man, and it
all seemed natural enough. So he returned to bed. When he awoke
at daybreak his bed partner was gone, but then he saw and felt the
crusts of dried cum on his face and his belly, and in the crack of
his ass. He felt stretched down there. No way, he realized, was
he a virgin any longer.
At breakfast Diana confirmed his surmise. She explained that
both men had done him after they'd brought them home, that neither
one seemed to mind using his ass when that was all they found under
his panties, and that he'd first deep-throated each and then
screamed joyously while they reamed him one after the other for
nearly two hours. "I expect your throat's feeling sore," she
commented in conclusion. "Mine would be. And not only my throat!"
He did feel sore, a little. He felt both pride and
humiliation that he'd been taken by a man as if he were a woman,
but he also felt resentful that somehow he'd been used. He was now
a real girl, and his ass was proven to be a workable vagina, but he
was also now a real cocksucker. Or maybe that was the same thing.
But he didn't feel different. "I don't know what it was
like," he complained to Diana. "I don't remember anything about
it."
"Aww! You feel cheated! We'll soon fix that," Diana said,
glancing up at him. "No problem, honey! I've got their number."
So she called the same men, who happened to be in town for one
more day, and they arranged another dinner. This time they had
only one glass of wine apiece, and Bob remained timorously alert to
everything that followed. His partner turned out to be as nice as
he had seemed. He joked with the two ladies during dinner and was
gentle and affectionate afterward. He admired Bob's budding
breasts when Bob took off his brassiere, and when he kissed them
Bob thought he would die with delight. After all that dildo
training his cock slipped effortlessly into Bob's pussy, no
problem, and Bob immediately felt that delicious feeling down under
begin to build up. He waited to cum until Bob's gasping climaxed
into shrieks, and then the feel of hot sperm spurting in his ass
set Bob shuddering into a second orgasm immediately on top of the
first. An hour later with a bit of sucking he was ready again, and
this time Bob went directly to heaven. He shrieked for joy through
three more orgasms, the last two dry. "Women's orgasms," Diana
explained to him later. "I told you you're a girl!"
Thereafter when they went out as a twosome they frequently
returned as a foursome, and when Diana and one of the men
disappeared into one of the bedrooms Bobbi was always ready to take
her man into the other. Diana put away that last dildo. Men were
nicer than dildos, Bobbi had to agree with Diana, even though they
were hairy and their beards scratched. It was a good feeling, he
thought when sometimes it worried him that he was being unmanly.
But he did so much enjoy feeling all that raw male cock with all
that muscle power behind it push energetically into him, and to
stroke and mouth all of that velvety nubby skin was a privilege!
After another few weeks of finding men and taking them home --
Diana never failed to attract the nicest, most virile yet decent of
them, Bob couldn't figure out how she did it -- Bob realized that
he was no longer sleeping with Diana at all. When he mentioned
this to her, she only shrugged and asked if he was unhappy. He
couldn't say he was. She asked him if he'd rather get laid by a
woman or a man, and he thought a long while before deciding on an
evasive answer. "I don't know," he said.
That was a good enough answer for Diana. A few days later she
suddenly appeared in Bobbi's apartment unannounced.
"Now Bobbi," she said. He sensed that suddenly Diana was all
business, though pleasant enough about it. "I haven't told you
before, but now you should know, because we belong to each other.
Don't we?"
"Yes," Bob said, with no idea where this remarkable woman was
now going. He was about to add, "I suppose, in a way," but he
sensed that around Diana her way was the only way.
"So listen closely, my dear. Some of this will surprise you."
He sat down, all ears.
"I'm very wealthy. Money is of no concern to me, and never
has been. I get what I want. I wanted you. I wanted you available
to do what I want you to do. To be a girl for me when I want you
to be a girl. Maybe with me, maybe with guys, maybe with one guy
I happen to have in mind. Never mind why. My reasons are my own,
and they're sufficient for me to have gone to a lot of trouble
preparing you, so I don't want you to bother your pretty little
head about them now. I know that your inheritance has nearly run
out, and soon you'll need to get back to work. If someone who
looks the way you do now can find work. Remember, you're not quite
the slim boy you were, and the clothes in your closet aren't his
clothes any more. Now you're a girl, aren't you? Pretty much
unskilled, so restricted to low paying jobs and glass ceilings,
right? Or, there's always the streets, but who knows what kinds of
men you'd find there? Or what diseases!"
"Well, if you continue to do what I say, you'll never have to
work again. You'll be free to indulge any whims that may occur to
you, within reason of course. In this purse is a whole new world
for you. To begin with, the ownership papers for this apartment --
it's really a condo. Right now it has a heavy mortgage, but if
you're happy with our arrangement, I'll pay it off month by month,
and in one year it'll be yours free and clear to live in or rent
out, whatever you like. Also a new driver's license made out to
"Bobbi," and the papers for a new BMW you'll find downstairs in
this building's underground garage. Also a few credit cards for
the best women's stores in town, and I'll expect you to use them
often.
"Women's stores, Bobbi. Because what you'll have to do for me
for all this, Bobbi, is agree to live as a woman whether I'm
supervising you or Erica, or neither of us. Just keep getting
used to it, and find out what kind of a girl you are, and live as
that kind of girl. I'll help you, of course. I'll start you out
with a few women friends who'll help you find a whole new social
life, and will see to it that you learn how to make men happy, and
also learn how to be happy despite the fact that they're men. We
all have to learn that. Then when you're ready I'll ask you to
come live on my estate. But that'll be later still, when the time
is ripe. If you don't like what I'll ask you to do then, you can
always say 'No' and at that point we'll part company, still
friends. But I think you'll love doing it. It won't be anything
I haven't done. Nor you, now, girlie."
She grinned at that, and then turned serious again. "I meant
what I just said. There will be men in your life. and one in
particular. I want you to learn how to love them, and how to want
to satisfy them, and how to become expert at making them happy and
satisfied. I will not want your affairs to include any men I
haven't chosen for you. So there is that restriction on your
social life. And the women in your life are for suitable
companionship and advice, nothing more. Your cock is useless now,
and your ass is mine! But all in all, you won't find life too
arduous."
"Will you agree to all this? Bobbi, do say yes. Please. For
me. Do take this purse. It also contains notice of your new bank
account, all yours, with a first amount in it larger than that
inheritance you were using up. And of course your makeup -- from
now on you'll never leave home without it. I'm leaving for Europe
tonight on business, but tomorrow a young woman will drop by to see
how you are. And to double date with you. You'll like her. She
started out in discos and she graduated to sex shop porn, and she's
been a model, and a street prostitute, and then she was kept by
several very influential men, so now there's nothing she doesn't
know and very little she can't teach you. She's well-educated, and
she's really quite respectable now. But I know you'll find it
amusing, learning some of the things she knows. I did."
She held out the purse, looking hopeful. A bit addled,
overwhelmed really, so choked up he was unable to say anything,
Bobbi took the purse from her, and nodded. She looked him over
closely and said "Good! It may be a while, honey, but I'll be in
touch. Enjoy yourself. That's your job from now on."
Then she got into her car, and drove off without looking back.
***************
