Date: Fri, 20 Apr 2018 00:18:40 +0930
From: Amanda Stern <astern50@gmail.com>
Subject: Saving Amy Part 3: Tiffany on Top

Please find enclosed a story for inclusion in the Transgender Control
section. It is a continuation of a story that started with Saving Amy.

- Amanda Stern


*SAVING AMY PART 3: TIFFANY ON TOP*

*There are surprises waiting for the sissified Tiffany as she undertakes
her probationary assignment for the SiFu Club. A lot more than food is on
the menu when she dines with her former boss!*

*Please think of donating to help support this wonderful site, and if you
have any feedback, please don't hesitate to email me at astern50@gmail.com
<astern50@gmail.com>.*

=======================


"Is there something wrong?" Mr Harper stood at the door, his handsome face
creased into a frown of concern.

Tiffany stared at the man who until a few months ago had been her former
boss -- or rather, Eric's boss. She had certainly never worked for him as
Tiffany. And strangely, he didn't seem to recognise her as a feminised
version of the young lawyer he'd fired for poor performance.

"No sir", she managed to say. "Just a bit nervous."

His face relaxed into a smile. "Ah yes, I gather that you're new to this
line of work?"

"Very, sir", answered Tiffany, "but I'll try to do my best." So not only
did he know what she was, but that she was on probation. Well, Nancy had
told her that he was a long serving member of the Sissyfuckers Club.

"Good girl -- I'm sure you will", he said, gesturing for her to come inside.
She stepped across the doorway, conscious both of the heels she was wearing
and the weight of the fluid that had been injected into her chest to give
her a temporary pair of breasts. She had been practising for a couple of
weeks in high-heeled shoes, but the feeling of having boobs was still
entirely novel. Combining the two was presenting a challenge, just in
keeping her balance.

He shut the door behind her, then led her down the hall and into an
elegantly furnished sitting room. "Would you like a pre-dinner drink?" he
asked, as she sat down on an attractive though not especially comfortable
couch. "Some champagne, perhaps?"

"Thank you sir, that would be lovely." He went over to a drinks cabinet,
which he opened to reveal a small refrigerated compartment. As he worked on
the cork of the champagne bottle, she studied him closely. He was slim and
clean cut, with greying hair and sparkling eyes. If she had to guess, he
would have been in his mid-forties.

He also had the ease of someone who was born into privilege rather than
ever having to work for it. Not that he didn't work hard, Tiffany thought.
There'd never been a day when she could recall Eric getting to work before
him, or leaving after him. You didn't get to be a managing partner of a law
firm if you were a slacker. But the point was, he never had to struggle to
get where he was. He wasn't especially arrogant, or dismissive of those who
came from less fortunate backgrounds. But nor did he conceal just how
comfortable he was with a life of wealth and power. Whether intentionally
or not, he projected an aura of natural superiority.

It was the same now. He'd just paid what Tiffany assumed must -- given the
sizeable fee she'd been promised -- be a very large sum of money for a night
with a pretend woman, and an inexperienced one at that. Yet there was no
trace of awkwardness or embarrassment in his manner.

"Here you go", he said, handing her a glass and sitting down next to her on
the couch. "Good health", he added, clinking her glass with his own. She
sipped the champagne, which was plainly French, and very good quality.

"Mmmm", he said, and for a minute she thought he was appreciating the
bubbly. But then she realised he was looking at her bosom. "Those are new,
I gather?"

"Yes sir", she answered, "but they're just temporary". He smiled. "What a
shame. Do you mind if I, ah, test them out?"

Tiffany bit her lip, but she was fully aware that she was not in a position
to resist the request. Not if she wanted to get paid, at any rate. Besides,
this was who she apparently now was -- just a sissy for sale. So she meekly
replied: "Of course not sir."

She sat stiffly as he reached over and felt each of her tits in turn
through the cocktail dress. "My goodness", he said approvingly, "they
certainly feel nice."

"Would you like me to get undressed sir?" she asked. Mr Harper laughed. "Oh
no. Well, not until later, at least. We'll have dinner first. And you can
forget the sir, by the way. Just call me Ryan, okay?"

"Yes sir -- sorry, I mean Ryan." He grinned at her slip, and for the first
time since she had arrived, Tiffany gave a smile of her own. At least he
was being polite, even if he had just been fondling her like a piece of
merchandise.

Somewhat to her surprise, he kept his hands off her from that point on, as
they sat, drank champagne and chatted. Tiffany found herself relaxing as
they talked about current events and the latest films and tv shows. Mr
Harper even made her laugh from time to time -- something that she couldn't
remember Eric having done since ... well, since he had been kidnapped and
tricked into working for the SiFu Club.

Their conversation was interrupted by the appearance of a very pretty young
woman dressed in what was recognisably a maid's outfit, though it was far
plainer than the fantasy uniform Tiffany had been forced to wear at Vance's
mansion. "Dinner is served, sir", she announced, the accent suggesting that
she had been born elsewhere.

"Thank you Juanita", said Mr Harper, rising to his feet and helping Tiffany
do likewise. He ushered her through the door and said: "The girl will show
you to the dining room. I'll join you there in a minute."

As he strode off, the maid gave Tiffany an encouraging smile and said "This
way please, miss." She was led into a room with a lengthy table. Sitting at
one end was a woman who Tiffany certainly recognised -- but had definitely
not expected to be present . She rose to her feet and gave a warm smile.
"Hello Tiffany, I'm Miranda Harper. Do please take a seat."

Miranda was, Tiffany knew, Ryan Harper's second wife. Eric had seen her on
a number of occasions at firm functions. Like many other young men at the
firm, he had lusted after her from afar. A former model, she was well into
her thirties now, but still turned male heads. The sparkling blue low-cut
dress she was wearing tonight was designed to emphasise her heavy boobs,
which together with her long and lustrous auburn hair had always been her
trade mark features.

What Tiffany simply couldn't understand was what Miranda was doing there.
She had assumed that her client's wife must be away, and Ryan certainly
hadn't mentioned otherwise. Yet here she was. Did this mean that she was
going to be joining in whatever sexual activities her husband had planned?

More than a little rattled, Tiffany took a seat at the place indicated,
next to Miranda. After accepting a glass of wine from the maid, she
nervously looked over at her hostess and said: "It's nice to meet you Mrs --
I mean, Miranda. But I didn't realise you were going to be joining us."

Miranda arched a perfectly manicured eyebrow. "I can't think why not.
You're not put out by my presence, I hope?"

"Oh no", said Tiffany hastily. "I just, er ..." Unable to think what to
say, she took another sip of her wine. Miranda seemed amused by this, but
made no attempt to call attention to her guest's discomfort, or indeed
increase it. To the contrary, she engaged in light conversation, which
continued when her husband joined them, and indeed throughout the dinner.

Tiffany was so out of practice at feeling relaxed and comfortable that it
took her a good hour to settle down. But eventually she realised that she
was actually enjoying herself. The food itself was of the highest quality,
though not so plentiful or heavy that it created problems for someone who
was thoroughly out of practice with big meals. The wine was delicious and
the Harpers were splendid company.

Indeed so good was Tiffany feeling that she had completely forgotten the
purpose of her visit. Until, just as Juanita was clearing away the dessert
plates, Miranda brought the subject up without any warning.

"So, Tiffany", she said brightly, "I assume your cock's in working order?"

The subject of her inquiry blinked and stared at her hostess. Her mouth
opened and closed. Then she looked round at the maid.

"Oh don't worry about Juanita", said Ryan jovially, seeing the direction of
her look. "She knows all about our little, ah, peccadilloes. Don't you
dear?"

"Oh yes sir", said the maid, shooting a smile at Tiffany, then resuming her
work.

"So", pressed Miranda, "is it?"

Tiffany swallowed. "I, um, think so ... It's just that, well, I haven't
actually used it in, er, quite a while really ..."

In fact, she couldn't remember the last time she'd even had an erection.
She'd been aroused for a good part of her night at the mansion, very much
against her will, but had been prevented from getting hard by the drugs her
captors had given her.

"Well, I'm sure you'll do just fine", said Miranda. "Perhaps we might start
by getting you, ah, up to speed. Ryan, get under the table and do something
about that."

Tiffany was shocked by the casual nature of the instruction, but even more
so by Mr Harper's reaction. "Of course dear", he said, then got down on his
knees and crawled under the table.

"Spread your legs and lift your dress up a little, please dear", said
Miranda. Her voice was still calm, as if nothing out of the ordinary was
happening. But it also had a strangely compelling tone.

Tiffany was feeling a little light-headed from all the wine she'd drunk,
not to mention the medication she'd received earlier at the clinic. In
something of a daze, she lifted her bottom and pulled her dress up so that
it bunched around her waist. She opened her legs and felt Ryan take up
position between them, though she couldn't see him. Then she gasped as she
felt him rummaging in her panties.

"Just relax dear, there's nothing to worry about", said Miranda in a
soothing voice. "But just to make things a little easier, perhaps I can
distract you a little." She rested a hand lightly on her chest, one finger
tracing her cleavage. "You've been looking at these all evening. Do you
like them?"

Tiffany blushed and nodded, then gasped again as she felt Ryan's fingers
close around her flaccid member.

"Well then, perhaps you'd like a better view", said Miranda. Without taking
her eyes off Tiffany, she called out: "Juanita!" The maid appeared behind
her. She rested her hands on the older woman's shoulders, then slid them
down her front. Working without hurry, she freed first one breast from
inside the slit in the front of the blue dress, then the other.

"Oh my god", whispered Tiffany. But whether this was because of the sight
of Miranda's large, creamy white boobs spilling free, or the wetness of
Ryan's mouth as it closed over her cock, she couldn't say. All she knew was
that she was suddenly so turned on that it hurt. Her groin was radiating
heat like a furnace. From beneath the table, she heard a choking sound as
her organ rapidly expanded to fill her host's mouth.

"That feels good, doesn't it?" remarked Miranda dreamily. "And so does
this, I can assure you", she continued, as the maid massaged her breasts.
"Mmmm", she said appreciatively. She looked up at the young girl who was
fondling her. "Come and sit on my lap."

"Yes ma'am", said Juanita. She did not look the slightest bit perturbed
about what she was being asked to do. She waited for her mistress to pull
her chair back from the table, then sat down carefully on the older and
much larger woman, allowing herself to be cradled as if she were a baby.
The impression was only increased when her head was guided to one of
Miranda's loose boobs, which she began to suckle.

Tiffany was torn between this astonishing tableau and what was happening in
her own lap. Her cock, now fully hard, was completely enveloped in Ryan's
busy mouth, so much so that she could feel his lips on her belly. And then,
incredibly, she felt him open his mouth wider still and engulf her balls as
well. Tiffany had never experienced anything like this from her (or rather
Eric's) girlfriends. The feeling of her genitals being swallowed was
amazing. How on earth he was able to breathe, she had no idea.

Lifting up the tablecloth, she looked down to see his head buried in her
groin. As she watched, he finally withdrew, gagging a little as he did so.
Streams of saliva ran down her shaft, which he quickly covered once again.
This time though he did not take it all in. Instead, he began sucking on it
vigorously, making an O with his lips and driving his mouth up and down the
top of her shaft. His eyes opened as he did so and he looked up into
Tiffany's face. As she stared back at him, he gave a brief grimace that
might have been an attempted smile, but then got back to work.

"By the look on your face, I'm guessing he did that deep throat thing?"
Tiffany swivelled her head to look back at Miranda, who was smiling at her.
"Yeah, that's a real party trick of his." She was gently stroking the cheek
of the maid, who was still busily kissing and licking one of her large
tits. "Bet you'd like to be doing this, wouldn't you Tiffany?" she asked in
a teasing voice.

"Oh yes ma'am", said Tiffany at once, her attention once again captured by
the scene across the table.

"Of course you would", answered Miranda. With the hand that was not
cradling Juanita's head, she reached down and lifted the maid's skirt. With
a thrill, Tiffany realised that the girl was not wearing any underwear.
Either she never did so, or she'd been well and truly prepared for what was
now happening. She was also completely shaven. The older woman slipped a
finger into her hairless quim and was a rewarded with a moan from both her
young companion and Tiffany.

As Tiffany watched the two women, she became aware of a rising tide within
her. All that she wanted in that moment to do was to let it roll through
and over her. But she was also aware that it wasn't up to her to make that
decision. Reluctantly, her breath shortening, she gasped: "Sir, ma'am, I
think I'm going to come ..."

Miranda's reaction was immediate. "Ryan, enough", she commanded in a firm
tone. Tiffany felt her cock being released and fought down an urge to grab
it herself and finish the job that Mr Harper had started.

"Time for bed, I think", announced Miranda. "Juanita, please take our guest
upstairs and get her ready, will you?" The girl gave the breast she was
playing with one last kiss and got to her feet, smoothing down her skirt.
"This way please miss", she said, walking over to the door.

Tiffany got up to follow her, but struggled to get her rock hard cock back
into her panties. She wasn't especially well hung, with perhaps five and a
half inches when fully erect as she was now. But even so, she simply
couldn't hide it under her dress. "Don't worry about that", laughed Miranda.

Tiffany stopped trying to smooth down her dress and followed the maid out
of the room, her cheeks burning with a mixture of embarrassment and the
strange heat that seemed to be suffusing her body. She was led upstairs to
a large bedroom.

"Okay, you take off that lovely dress", said Juanita. Tiffany obediently
turned around and allowed the maid to unzip the dress, then let it fall to
the floor. "Bra and panties too, I think", said the girl. "But leave shoes
on. And stockings of course."

Tiffany hesitated, but then removed the requested items. She was wondering
whether she should cover herself up. But when she turned around, she found
that Juanita too was stripping out of her uniform, so she didn't see the
point. The girl had a slim body, with tits so small they were scarcely
bumps on her chest. She seemed a lot more interested in Tiffany's boobs,
however.

"Oh wow", she said, reaching out tentatively to touch them, as if afraid
they'd burst. "These just ... what the word, temporary, right?" Tiffany
nodded, then shivered as the girl gently fingered her nipples. They were a
lot more sensitive than she could ever remember, though whether that was
because of the injections, the drugs she'd been given or just the fact she
was so aroused, she couldn't say.

"Well, they look strange", said the maid in a critical tone, but then
grinned. "But feel okay. And you look real pretty. This the first time you
be a girl?"

"Second", said Tiffany. Juanita nodded. "Pretty good. Just shame about
that." She indicated Tiffany's cock, which was still standing proud.

"You don't like, um, penises?" asked Tiffany.

"No", said Juanita emphatically. "And if I did, mistress not allow it."

"So you don't, I mean, sleep with Mr Harper at all?"

The maid laughed. "Oh no, only with mistress. Unless ..."

"Unless what?"

"Well..." Juanita looked around, as if afraid she might be overheard. She
lowered her voice. "Sometimes if she not happy with him, she make him stay
in bed with us while we, you know, have sex. Just make him feel bad I
guess."

"So they don't normally sleep together, even though they're husband and
wife?" asked a mystified Tiffany.

"Never. That husband wife thing just -- how you say, just for show, right?"
She looked round as there was a clanking sound outside in the hall and gave
a little giggle. "You see right now!"

If Tiffany had been shocked by the behaviour at the dinner table, she was
downright stunned by the entrance of Mr and Mrs Harper. She entered first,
wearing the same dress she had donned for dinner, with her large breasts
still hanging free. She was holding a chain, which was attached to her
naked husband. She pulled it taught, causing him to stumble into the room.

Tiffany had to look twice to work out what the chain was attached to. It
was a metal device that tightly encased Ryan's flaccid cock in a series of
rings. The one at the base was tucked behind his balls, which seemed
slightly enlarged. The whole contraption looked incredibly uncomfortable.
Yet if its wearer was suffering any distress, he wasn't showing any signs
of it. Nor, however, was he looking at Tiffany. His eyes were downcast, and
his whole attitude conveyed a submissiveness that was at odds not just with
how he had behaved at dinner, but with everything Eric had previously seen
when they worked together.

Miranda laughed. "Not quite what you were expecting?" She walked over to
her husband and unclipped the chain. "Ryan, tell our guest what this is and
why you wear it."

"Yes mistress", he said obediently. Without looking at Tiffany, he
explained: "This is my chastity cage. It stops me ... getting too excited.
Wearing it is part of the agreement I made with mistress."

"The agreement?" asked Tiffany, looking first at Ryan, then Miranda. It was
the woman who answered. "A couple of years ago, I discovered that Ryan had
been fucking his secretary. I gave him a choice. He could have an expensive
divorce, or he could agree to be my property. We'd already been playing a
lot of discipline games, so I knew he was the submissive type -- at least
where I was concerned. The cage sealed the deal, if you like. It's locked,
and only I have the key."

"So he wears that all the time?" Tiffany couldn't decide if she was
horrified or fascinated. Probably both, she thought.

"Oh yes. Except every now and again when the cage needs cleaning, and I can
assure you he is very strictly supervised on those occasions."

"But wouldn't that mean he can't ..." Tiffany trailed off, too embarrassed
to complete the question.

Miranda laughed again. It was clear she found the whole conversation hugely
entertaining. "He can't come? No, orgasms are perfectly possible ... just
very, very hard to achieve. And as enjoyable as they used to be. Especially
as he doesn't get to touch women any more. Not real ones anyway. But if
he's been good, then he's allowed to have a pretend one. He joined the Club
you work for a long time before he met me, so it's one of the few perks
he's still allowed -- though only when I permit it of course."

Tiffany still couldn't process what she was hearing. "But he wasn't like
that at all when --" Her hand flew to her mouth as she realised her mistake.

Miranda's smile was positively malicious now. "When you worked together,
you mean? Don't worry, I'm perfectly aware of your connection with Ryan. He
recognised you when the Club sent through details of possible candidates
for tonight. And like a good little slave he told his mistress all about
you and why it would have to be someone else."

She gave a delicate shrug. "So of course I told him it would have to be
you. And that not only was his former employee going to come and fuck him,
but he would have to endure the shame of having our domestic arrangement
exposed."

Miranda cocked her head sideways and gave Tiffany a piercing look. "You're
one of the few people outside this house to find out about how Ryan really
lives his life. For everyone else, we maintain the charade of being husband
and wife. But I thought it was too delicious for you not to know.
Understand this though. It remains a secret, even from your employers. Got
that?" Tiffany nodded.

"Good. Because I have my own connections with the Club and if I ever find
out you've opened your mouth, I can make your life a living hell. Now,
let's get on with this, shall we?"

"Yes ma'am", said Tiffany, but then hesitated. "It's just that ..."

"Just what? Spit it out."

"Well, I was told that Mr Harper , I mean Ryan ... that he was going to be
... I think they said a top as well as a bottom? Only I'm not sure how ..."
Tiffany gestured at her former boss' caged cock.

Mrs Harper gave a guffaw. "Oh, so that's what you're worried about! If you
like, I have a nice big strapon that Juanita could use on you. Or if you
prefer the real thing, we do have a rather, ah, rugged gardener. I could
give him a call and see if he's free?"

Tiffany swallowed. "Uh, no thank you ma'am, I'm happy to go without."

Miranda sniffed. "Well, suit yourself. Now, enough talk. Ryan, you can give
Tiffany here a kiss and a cuddle and pay some attention to those artificial
tits you seem unaccountably fond of."

"Yes mistress", intoned her husband. For the first time since entering the
bedroom, he looked up. "Tiffany", he said gently, his face strangely
serene, "would you mind joining me on the bed?" He took her unresisting
hand and led her to the large bed. Heart pounding, she lay down on it next
to him, turning on her side to face him.

She had no idea what to do next, but it didn't seem to matter. He reached
out one hand to grasp her now semi-erect cock, while simultaneously leaning
in to nuzzle and kiss the side of her neck. He worked his way slowly
downwards, lavishing attention to her smooth, perfumed skin, while
alternately fondling her shaft and running his hand over her stockinged
thigh. When he reached her breast, he ran his tongue around and under the
fluid-filled mound, until finally his lips closed on its centre.

Juanita's touch earlier had been exciting, but it was nothing compared to
the electricity that ran through Tiffany as Ryan's mouth did its work. She
felt both her nipple and her cock stiffen in response to the man's rapt
attention. As if by instinct, she reached round with her free arm and
stroked his back. He was clearly someone who kept in shape. His body was
firm, well-muscled and covered by a pelt of hair that was largely black,
except for a patch of grey in the centre of his chest.

Somewhere in her mind, she knew she should have been revolted by the idea
of caressing a man. And in truth she was. But nor could she ignore the
stimulation to her sensitive parts.

But an even bigger challenge was to come. Relinquishing her boobs, Ryan
lifted his head up and brought his mouth down on hers.

She had never been kissed by a man. On that horrible night at the mansion
she had been forced to endure all kinds of indignities at the hands (and
more especially cocks) of the guests. But none of the men had tried to kiss
her. And besides, their control over her had been absolute. She had thought
she was saving a young woman, and there had also been an implicit threat of
violence. But she had chosen to come here. She didn't have to submit to the
indignity of letting this man kiss her, even if he had once been her boss.

But in the end, it was precisely because she had chosen to be here that she
submitted. The twisted logic that had prevailed in her mind since her
violation at the mansion told her that if she allowed herself to be
sissified and prostituted, then that's what she deserved. She was a sissy
whore, so that's how she had to act -- no matter how shameful and
humiliating it felt.

So she didn't just let him kiss her. She kissed him back -- and not softly
either. The sensation was a strange one. She tried to imagine that she was
kissing a woman, but his lips -- and especially the stubble around them --
felt totally wrong. Far easier to play the part of who she feared she was --
a man who'd been paid to dress as a woman and not just kiss another man,
but fuck him too.

She felt him respond, allowing his tongue to probe her mouth. She pulled
his upper body hard against her, so that she could feel his chest hair
rubbing against her pseudo tits. But she was careful not to get in the way
of the hand that was busily stroking her rigid member.

After a few minutes of this, she heard a voice say: "Enough kissing. Get on
your knees and elbows and let me see that ass of yours." As Ryan moved to
obey, Tiffany was surprised to realise that it was she who had given the
order, not Miranda. So why had she done that? Well because she was playing
a part -- the sissy slut who was being paid to fuck her client. And because,
despite everything, she was feeling horny as hell. The need might have been
shameful, but it was real.

She found herself kneeling behind Ryan, who as instructed was down on his
knees and forearms, with his butt in the air. With a thrill, she realised
that he too had been shaved, so that his puckered asshole was fully visible.

She was wondering how to go about penetrating him, when she felt a tube
being pressed into her hand. She turned to see Juanita's grinning face.
"Lubricant", said the maid. Tiffany nodded her thanks, then took the top
off and squeezed a clear, viscous fluid into the palm of her hand. She
daubed some on her cock, then let the rest slide off her fingers and pool
around the exposed rectum beneath her. She thought for a moment about using
one of her fingers to open it up, but recoiled from the idea. Besides, she
was feeling too desperate to delay her gratification any further.

Eric had never experienced anal sex, nor even thought of suggesting it to
any of his various girlfriends. And while Tiffany had been on the receiving
end, both at the mansion and on the way back from that ordeal, this form of
it was new to her too. But she did not hesitate. Manoeuvring herself into
place, she pushed hard against Ryan's rear entrance. There was a brief
resistance, but then she slipped inside.

It was easier and less tight than she would have expected. She wondered if
Ryan was routinely forced to keep a plug in his bottom to keep it
stretched, as she had been at the mansion. Even so though, it felt
different to a woman's pussy. She was not sure she liked it, but that
wasn't the point.

"What do you want, Ryan? Nice and loud now ..." Tiffany marvelled at how
much in control she sounded, when in fact she was a prisoner to her shame.
But it seemed she could at least play at being on top. She waited for the
answer with her cock buried deep inside the man's back passage.

"I want you to fuck me. Please Tiffany, please fuck me hard!" The response
was a compelling one, but even so Tiffany looked around.. Miranda was
sitting on an armchair, idly fondling the naked maid on her lap. She smiled
and nodded her permission. So Tiffany gave Ryan what he wanted.

There was nothing remotely subtle about it. She simply pounded her pole in
and out of his behind, going as far inside as her modest length would
allow. With each smack of her pubic bone against his buttocks, he grunted.
Though whether this was pleasure, pain or discomfort she didn't know and
didn't really care.

There should have been nothing erotic about fucking a naked man. Yet
something about what she was doing turned her on, though whether it was the
physical sensation of his anal passage clenched around her inflamed glans
or the sheer wrongness of what she was doing, she couldn't say. The only
thing she was sure of was that any satisfaction did not come from the fact
that she was buggering the man who had fired her. Eric might possibly have
felt that, but not Tiffany.

Whatever was driving her, she didn't have much time to reflect on it. She
had been hurling herself down and into him for what seemed like only a few
minutes before she was overtaken by a toe-curling orgasm. Urged on by her
partner, who seemed to relish being used in this way, she sent wave after
wave of pent-up sperm into his hole, until she felt that she must be
sloshing in her own cum. Then, still locked inside, she collapsed on top of
him.

She was roused from her torpor by a slow handclap from behind. "Very nicely
done dear", commented Miranda, "that was certainly an excellent start. But
we do have a rule here -- Ryan has to swallow anything that gets put either
into or onto him. So you'll need to help with that, okay?"

Tiffany nodded, but the distaste must have shown on her face, because the
older woman laughed and continued: "Don't worry, he's perfectly clean back
there. Juanita gave him an enema herself this afternoon, didn't you?" The
maid took time out from the enjoyment of having her pussy fingered to nod
her assent.

Pulling her still hard cock from out of Ryan's ass, Tiffany thought for a
minute, then manoeuvred her head until it was underneath his bottom, her
feet pointing away from him. She then asked him to kneel upright. As he did
so, her cum began to dribble out of his rectum. There was an awful lot of
it and it took three goes to gather it all on her mouth. With each portion
she kissed Ryan and transferred her fluids into his mouth, then waited for
him to gulp it all down.

The whole process should have nauseated her. Yet the very sluttiness of
sucking her cum out of his bottom and dribbling it into his mouth seemed
perfect for the part she was playing. There was nothing enjoyable about it
-- but then, she thought, sissy whores weren't supposed to enjoy their work.
They just got on with it.

And to her surprise, she didn't lose her erection. The chemical she'd been
given at the clinic was plainly working its magic. No sooner had she
finished cleaning up her first orgasm when she began the journey to the
next. Laying back on the bed, head comfortably propped on a pillow, she
divided her attention between Ryan's enthusiastic blowjob and the sight of
Miranda sitting with her legs wide open, dress hiked up around her waist
and Juanita energetically lapping at her hairy quim.

Miranda had already come twice when Tiffany spurted into Ryan's hungry
mouth. There wasn't so much to clean up this time, fortunately, and the two
couples took the opportunity to rest and recover in each other's arms.
Tiffany felt strangely at peace lying there naked with her former boss, his
head resting on her steadily deflating boobs. It was disgusting, but also
somehow right. She knew that in the days to come, she would remember her
actions with the deepest chagrin. But she would also recall how much she
had enjoyed her orgasms. They were proof that she was indeed a slut. Maybe
she wasn't playing a role after all, just a darker and more perverted
version of herself.

Soon enough, both Ryan and Miranda wanted more. They swapped places, at the
older woman's insistence. She and her young lover lay on the bed with their
legs entwined, both fully naked now and grinding their snatches against one
another. Tiffany leant back in the armchair, with Ryan sitting on top and
lowering himself until he was impaled on the sissy's rampant cock. At his
mistress' insistence, he did the work, using both his hands and feet to
lever himself up and down.

Tiffany, although distracted by the amazing scene on the bed, noticed that
Ryan seemed to be varying the angle of her penetration of his by now
well-greased passage. A series of moans eventually suggested that he had
found what he was looking for and he increased both the speed and power of
his plunges. When Tiffany reached round and started to play with his
nipples, the volume of his cries only increased.

On the bed, Miranda and Juanita interrupted their own lovemaking to watch
the two on the chair. Tiffany could feel her own orgasm approaching and was
now pushing her pelvis upwards to meet Ryan as he took her cock. But it was
her partner, unexpectedly, who came first.

Looking down over his shoulder, Tiffany marvelled at the sight of the man's
tightly caged cock twitching and spurting, without anything touching it.
She knew from her own experience at the mansion that it was possible to
reach an orgasm purely from anal stimulation. In her case there had been no
joy whatsoever in the release and her semen had simply dribbled out of her
chemically inhibited organ. But this looked more dramatic, and Ryan's
groans of relief certainly suggested as much.

But she had little time to reflect on it, because now her own orgasm was
upon her -- and strangely, it was the most intense yet that evening. She was
left gasping as the sensations coursed through her. In the background she
could hear the women on the bed giggling, but all her thoughts were on the
hard spike that she had driven deep into her former boss, and on the feel
of his sweaty, shuddering body against her own.

As her breathing slowed, she turned his head to face her and kissed him.
They stayed there for a while, lips pressed together, tongues gently
intertwining, her twitching cock still inside him. Finally, he broke the
kiss and murmured something that at first she couldn't make out, but then
realised was simply "Thank you". A single tear ran down his cheek.

And just like that, the spell broke. Ryan climbed off her and there was cum
all over the place, which had to be cleaned up. The sense of shame had
returned, just sitting in the background to remind her that what she was
doing was disgraceful and wrong. And Miranda was berating her husband for
daring to come without asking permission and promising all kinds of
retribution. Plus, Tiffany was still hard ...

By the time morning came, she was drained and exhausted. Although unable to
come again, she had been required to fuck Mr Harper for what felt like an
eternity, in all kinds of position, before finally being allowed to grab a
few hours of sleep in a guest bedroom. The man himself had been led away,
with his mistress threatening to hang him up in chains for the night.
Tiffany had no way of knowing whether this was an idle threat, but he did
seem a little haggard in the morning.

Even so, as he walked her out to the limousine that had arrived to pick her
up, his manner was very much calm and relaxed, just as it had been when she
arrived. Looking around to make sure they could not be overheard, she
whispered the question that had been on her mind for the last several
hours: "So are you really okay with this? I mean, about being a slave when
you're at home? It seems ... pretty extreme."

She could not help but cast a glance down at his groin. There was nothing
to give it away, but she knew the cage was still there underneath his pants.

He smiled. "I've never been happier. All the stress I have to put up with
at work? None of it comes home with me now. Any decisions that matter are
taken for me. If I'm punished, I usually deserve it. And if I don't? Well,
let's just say I've done bad things before in my life, and the ledger has a
way of balancing itself."

His face turned more serious. "But what about you? When I last saw you, it
seemed things had gotten pretty desperate. Now look at you! I mean, you
could probably do with putting on a few pounds, but you make a sensational
woman ..."

Tiffany gave a sad smile and leaned in to peck him on the cheek. "That's
sweet of you. You know, I don't blame you for firing me .. and I'm really
glad we had such a good time. And as for me, well, I'm still trying to
figure out who I am and what I'm good for."

Ryan looked at her for a minute and then said: "Well, I'll certainly be
giving the Club a glowing report on how you did. I can understand if you
don't want to make a career out of this kind of work -- but you do seem to
be a natural!"

And that, Tiffany reflected as the car drove her away, was precisely her
problem. She had done "this work" twice now -- once out of a mix of
compulsion and necessity, and once through choice. It ashamed and
humiliated her ... and yet all she had to show for it was satisfied
customers. So maybe she really was what she most feared: not just a sissy
whore, but a good one ...


*To be continued in Part 4: School's Out*