Man Dating Ch. 7

By Caroline S. 

The princess was riding on her pony. The saddle, specially made for her
by the finest craftsman in the kingdom, felt good under her small bottom.
The day was already bright and the trees were singing to her in the

But then the ground started to shake. The trees trembled at the roar. It
was an earthquake, she thought. She tried to turn her horse around, but
the young mare was frightened as well and reared up suddenly, throwing
her to the ground. The thump knocked the wind out her. She tried to
stand, but the movement of the earth was now too violent, and the roar
deafening in her ears. She cried out, "Stop, please," unable to stand.
And Tuck woke with a start to the sound of pounding.

The lights were out, and the sun still had not pulled free of the
mountains to the east. The day had not started yet, but still the noise,
a hammering on his front door, would not stop.

"I'm coming, I'm coming," he said, rubbing the sleep out of his eyes,
unaware that he was pushing yesterday's mascara into a black smear under
his eye.

He stepped up to the door and peered through the spy hole, the image
blurred and for the most part unrecognizable, except as human and
potentially female, as whoever was on the other side had long blonde
hair, but had turned away at that moment so that the face was not

"Who is it?" he said through the still closed door, not terribly
concerned, but unwilling to open the door. He felt no real threat from a
single blonde haired woman, but he was only dressed in the little blue,
silk, under all, one piece that he had been give yesterday at the start
of a very strange day.

There was no answer to his question. "Just a minute, I'm not dressed."

"You don't have anything that I haven't seen. Now open the god damned
door!" and she began to beat on the door with even more ferocity and

He knew that voice... it was the witch from the club.

He saw no recourse. She was certain to continue hammering on the entrance
to his apartment, and the clamor would soon raise the attention of his
neighbors, if hadn't already, and potentially the police if he totally
ignored the situation. In either case, it was an outcome that could not
be tolerated.

He opened the door and she strode in as if she owned the place, carrying
a suit carrier and a small suitcase.

She eyed him up and down in his little blue lingerie. She smiled. "Cute."

“Thanks,” he said, making it very evident that the comment was not all
that appreciated.

“What are you doing here?” he asked, looking at the garment bag and
suitcase, afraid of the answer that he was sure to get.

“Stop asking stupid questions, we only have two hours before your
shopping date with Ms. Getty, and I’m here to get you ready. Now go get
in the shower.”

Tuck looked at her and knew that she still held all the cards. He turned
to walk back to his bedroom, wanting desperately to get back to the bed
and bury himself in the warm covers and soft pillows, but instead walked
into his custom bathroom; although today it felt more like walking into a
glass aquarium as Debbie followed right after him.

“Hurry up, we don't have all day.” She was urging him to disrobe in front
of her. Her arms were crossed, her body language demanding his prompt and
full compliance.

Resigned, he slipped the straps of the one piece off his shoulders and
then pulled the bottoms down from his behind. He turned around, facing
away from her, and slipped them completely down and off and stood naked
with his back to her. He slowly turned back around, his hand covering his
little toy, now shriveled, and afraid under the gaze of the witch.

“Put your hands over your head, I want to make sure there are no stray

Having been fully naked in front of this woman before, Tuck saw no real
reason to put any effort in resisting this morning. With trembling hands
he raised his arms revealing his small package, still not having
recovered from the previous day’s treatment. The little fleshly tube hung
just below his empty sack, his balls still pushed up and hidden, refusing
to reappear. Inwardly he was concerned with their reluctance to emerge
and take residence in their proper place.

She reached over and took hold of his baby cock, feeling for the absent
balls and pulling on his diminished member slightly to see if it would
react to her crude ministrations. There was just the slightest of
movement toward an erection. “Looks like we need to use a little more
cock cream on your little toy to keep it well under control for your
shopping expedition, but I can add that after you take a shower.” She
continued to run her hand evenly up and down his chest, the smooth bare
skin slipped easily under her delicate fingers, looking for the slightest
evidence of man hair. She pushed him this way and that, making sure she
inspected every inch if his naked body. “Still baby smooth,” she assured

Tuck shivered under the demeaning inspection, her hand rubbing his most
sensitive and denuded skin in a most rude and belittling manner.

“Bend over and pull your cheeks apart,” she commanded him, pushing him
around and bending him over at the waist. He took his hands down from
over his head and placed them as instructed on his bottom swells and
lightly pulled on them.

“Wider, now, before I get angry.”

She already sounded angry and her demeanor had not improved since she
stepped through the door.

Tuck pressed hard, and with his fingers digging into his naked and bared
cheeks, pulled each soft globe to the side. He could feel the strain on
his bottom hole, the not so virgin opening of his flower that had been
comprised most recently, and now this. Her finger traced around the
pucker, and once satisfied that no errant hair had been missed, she
pushed her way past his privacy until her long delicate finger was lodged
firmly inside. She stroked in and out several times, finger fucking Tuck,
taking full advantage of his newly opened boy cunt. She continued to do
it slowly until Tuck finally moaned aloud.

“Oh that’s precious,” she said, her finger still deep inside his boy
hole. “Feel good? Can’t wait to have the real thing, Jake’s nice fat
cock? Oh it will feel so good honey, in and out. I know it’s so thick and
huge and warm that you’ll feel so well fucked and so full.” Her words
were punctuated with her finger stoking him openly. Tuck moaned again. He
wasn’t sure if it was the erotic feeling of Debbie’s finger stroking in
such a slow and sensuousness manner, or her words that described a future
that was a dream or a nightmare. At this point he was very confused.

“Ok good, I don’t see any evidence of manliness at all, and you’re still
nicely greased and open.” Her comment meant to cut cruelly and hit the
mark square on the head. She pulled her finger free, wiping any of the
slick oil that still coated his insides across his chest and then in his
hair. “So go take a shower. I have some products I want you to use.” She
opened the bag she had carried in from the living room. “First use this
all over your skin, neck down. Don’t get any in your eyes or in your

Tuck looked at her, questioning her instructions, trying to see if the
bottle had any other instructions or, more importantly, warnings. As if
answering his unasked question, she took it away and pointed to the

“It’s a skin polisher and will get any hairs I missed yesterday. You’re
to use this every morning from now on, it will keep you girl smooth.”

She took another bottle out of the bag and handed it to Tuck. “Use this
one on your hair,” and then pushed a third bottle into his already
crowded arms, “and this to rinse.”

She was handing him different color bottles and shapes and he was sure
that it was critical to keep the uses and colors straight, or he would be
sporting a polished and very bare head.

“Use this one to wash your little toy. Make sure you leave the cream on
for at least five minutes. It’s thick, so be sure to coat it well… balls
too, if you can find them,” she laughed.

The bottles were all labeled in small, hard or impossible to read labels,
each bottle a different shape and color. The last one she handed him was
a bright pink in color. “This one is for your douche. I will make it up
for you this time, but you are to douche each morning.” She showed him
the matching pink rubber bag and wide hose with a very realistic, thick,
penis shaped nozzle attached. It reminded him of the spa’s evil toys.

“Pour a cup or more into the bag and then add hot water till the bag
bulges. Make sure you use the pink bottle. Then use this one,” she handed
him yet another bottle, this filled with a clear oil, “and use it to
flush the douche. You will find it filled with scented oils that I think
you’ll find most relaxing, I do.”

“I want you to gargle with this.” She handed him a green liquid and
another bottle. “Then finally use this soap after you finish with
everything else. I want you to smell clean and fresh for your shopping
date.” She handed him one last bottle, and it had flowers on it so he
thought he could keep that one straight.

He took the arm load of products that she had just presented and shuffled
into the shower room, juggling the various bottles and doing his best to
remember the list of instructions. The blue bottle was the skin polisher,
the only one he really had to keep in mind, and maybe the thick cream he
was supposed to use on his already frightened penis, still cowering
tightly between his hairless legs. Once in the shower he lined the
bottles up on the shelf previously laden with products of his own
choosing, the new making way for the old.

The shower had three heads on the side and two overhead. The controls
were on the wall and he was able to select temperature and spray type,
and even had favorite presets. The water temperature was also preset and
most welcomed on his newly denuded skin. He let the water fall full force
from all of the nozzles in what he called the drench mode, the water
washing away, at least for a moment, the consternation that had come to
his door this morning.

The changes were coming at him so fast. Yesterday had been like a cyclone
had hit, changing everything. And then last night his first man date. He
tried to do a quick evaluation of the evening as the water streamed down
from above.

As he fell into bed the previous evening, the thought that kept coming
back was a wave, up and down, positive and negative, going well, and
falling apart. As he let the evening unwind in his mind the wave was
real, but overall it was positive. The conversation, the food, the
wine... lots of wine; he almost didn’t remember tasting the unique desert
by the time it was served. He smiled, remembering that he had, in the
end, cut off a few pieces of the cum filled pastry and actually fed them
to Jake.

Jake had smiled and remarked on the smooth texture and sweet taste. Then
there was the door. Jake had walked him back to his apartment… had there
been more? That last bit was fuzzy. He had given the key to Jake, that
part was clear, his own hand being unsteady, not stable enough to find
the right entry. Jake had turned the lock and opened the door. Did he
come inside? No, Tuck couldn’t remember that part, but there had been a
hug at the door; a hug, a manly hug, just between friends. But was it?
Tuck remembered feeling the strength, the bulk, the difference between
the two of them, and then one other thing, the bulge. And then it was
over. The next thing he heard or remembered was the banging on the door.

“We don’t have all day… get busy.”

Her voice jolted him out his momentary solace and the remembrance of the
last evening. A new day was just starting and the cyclone was hovering

He looked at the line up again. The first bottle was the polisher,
followed by the cream she wanted on his little toy, and then the hair
wash and rinse, and then the douche.

His ablutions were over in about thirty minutes, and thankfully, due to
the endless hot water afforded by the gas on demand system he had added
and was still paying for, the water never turned cold or even changed a
degree. He ran his hand over his arm and was amazed at the smoothness,
not a hair remained. He felt his hair too and was amazed at how soft it
felt, almost like silk. But it was the thick cream and its result after
being applied to his already small penis that was the most startling. It
was almost as if it the thick paste had made his cock disappear.

The ointment had hardly poured out of the bottle, but rather oozed out in
to a stiff mound in his hand, and with Debbie’s instance from her
position outside of the glass wall, but overseeing his new morning
ritual, he carefully applied the sticky goo over his entire crotch.
Already denuded of hair, the cream, like a cold candy, coated his penis
and balls, but only with some effort and the use of both hands.
Instructed by vigorous hand signals his tormentor urged him to use more.
He poured more out and applied it thickly, almost hiding his penis under
the pink coating. The five minute wait, even with the warm water
cascading over his back, was interminable. And Debbie’s watch was the
only governor for the time, with the thick paste doing whatever job it
was going to do. The itching and burning had also started, a secondary
time element that was hard to miss.

As the water washed the coating away, he could see that his pink skin was
completely void of any hair at all, and if possible his sack had shrunk
even more and his penis had all but contracted back into his body. He
looked up at Debbie, aghast as to the result, but she just smiled and
said where it was just barely audible over the rush of the shower waters,
“What we girls won’t go through to be beautiful.” She laughed again.

Still dripping water after the shower, Tuck looked down at his bared
crotch, the last of pink candy having been washed away with the final
rinse. It was like it was gone, only the smallest nub remained. His
entire penis had retreated and was little more than a lump. He played
with it carefully, seeing if he could get his diminutive manhood to

“Stop playing with yourself and get out of there!”

She had opened the door and was smiling as she looked between his legs
and saw the expected and well received miniaturization caused by her
special cream.

“Perfect, your new jeans won’t have the slightest bulge. Come on, let’s
get you dressed, I still have to do your hair and make-up.”

There was no escape from this woman and her revenge plan. He wondered how
Mrs. Getty fit into all of this, but he felt confident that she would
share that information when it would be the most effective and beneficial
to her; almost an exact opposite as to when it would have the most
negative impact on him.

Having the last of the morning shower dampness negated by the body air
dryer, he followed Debbie back into his bedroom. On the bed, laid out as
if the invisible man was wearing it, was the ensemble for the day. On the
surface it looked, if not manly, at least not girly. He decided he could
go with a description of neutral. But he was also sure that as he put it
on and the combination was complete, the total effect would be anything
close to manly.

“Panties first,” she said as she held up a pair of blue delicates and
tossed them in his direction. He quickly put them on, hiding his
embarrassment, but the result was worse than being naked. The semi sheer
fabric and tight fit showed no bulge at his crotch. In fact, as the
panties found their place, a ‘V’ had formed showing off an almost perfect
and totally normal camel toe.

“Oh that’s perfect,” Debbie laughed. “I have to get a picture for Jake.”
She whipped her cell phone out of her purse.

“Now stand right there, hands on hip, and look at the camera. Oh Jake is
going to love this.”

She flashed her camera three times, sending each of the images off into
the web world and landing on Jake’s phone.

Only seconds later the chime on Tuck’s phone went off. The picture had
changed again, and this time it was a picture of last night’s desert as
it was presented. The picture was clear enough that you could see the
cream coating the top of the pastry.

“You had better answer that.”

Tuck, still standing in just the tight blue panties, hit the receive
button, ready to hear Jake’s voice blasting him for such an early morning

Debbie took the phone away, quickly hitting the speaker function and said
the first words, “Morning, Jake.”

“Hi, Debbie. Thanks for taking care of Marion this morning, it is much

“Think nothing of it, Mary Anne and I are becoming best of friends.”

“That’s nice. Marion, you’re not giving Debbie a hard time about anything
this morning, are you?”

Jake hadn’t said a thing about the pictures. Perhaps he hadn’t seen them,
or perhaps they weren’t really sent. “No Jake, of course not, it’s such a
joy having her here to help me get ready this morning. I’m looking
forward to shopping with Mrs. Getty.”

“That’s good to hear, as I asked Debbie as a personal favor to come over
this morning, and Lawrence picked out a special outfit for you as well. I
will expect you to give Lawrence a proper thank you next time you visit,

“Of course, Jake. It was just sweet of him to take that extra effort for
me, I will be sure to give him an extra special thank you.” Tuck was
being very careful to stay away from his usual ‘yeah sures’ and ‘gotchas’
in his responses, and was hoping his efforts were not going wasted or
ignored. He was also thinking of the special thank you that Lawrence was
sure to expect.

“I assume you are satisfied with Marion’s cooperation this morning?”

The question was to Debbie, of course. Jake’s voice was clear and
distinct over the speakerphone, filling the small room. “Yes, I have been
mostly satisfied. Some of the bath products I purchased and brought over
were a bit new to him, and there was some questioning, I’m afraid.”

Tuck looked daggers at Debbie, knowing what was to come from her response
to Jake’s question.

“Marion, I won’t tolerate this at all. Debbie has gone out her way to
help, and to have any complaints is very disappointing. We’ll talk about
your attitude, I can assure you.”

“Debbie, accept my apologies, this will not be taken lightly. Marion you
can apologize now.”

Tuck was not sure what to apologize for, but knowing that he had really
no recourse at this time, other than to make some vocal comment that
would appease Jake and negate the imaginary affront he was to have done
to Debbie.

“Debbie, please accept my apologies. I know how much you’re trying to
help me become a better person, and it was wrong of me to question your
selection of products that you so kindly brought for me to use this

He stopped, thinking that that was enough of an apology to still the
fantasy she had created and satisfy Jake’s demand.

“And it will never happen again!” boomed Jake’s voice, urging an addition
to the apology. It was barked and offered no room for compromise.

“Yes… yes…” Tuck stammered, “…sorry. I’m sorry, it will never happen
again. I won’t ever give you any back talk or argument. Please accept my
apologies. “Tuck was scared that nothing he could utter would satisfy.

There was a long pause, but then Jake’s voice came over the phone. That’s
much better, Marion, but we’re still going to have a conversation about
your attitude.”

“Of course, Jake, I understand.”

“Put Debbie on the phone.”
Tuck let Debbie have the phone and she immediately switched off the

“No Jake, really, it’s been no problem at all.” She smiled and glanced
over at Tuck wearing only the little blue piece of lingerie. She pointed
to the floor and took a seat on the bed.

Tuck cocked his head to the right and asked silently what she wanted now
and she pointed more to the floor this time and lifted her shoe off the
ground slightly.

Tuck bent down to his knees in front of her looking at the shoe in
question, wondering what she wanted him to do with it. She held it up
again, higher, pushing it into his face, and he took it in hand
inspecting the stockings for a run, or the show of some debris that
needed to be removed. He was puzzled as to what she wanted him to do with
the shoe now that he was down on the floor. He looked up at her, a silent
question on his lips. “What?”

“Yes, I can have him there a few minutes early.” She put her hand over
the phone, cupping the microphone so her voice was in whispers, keeping
Tuck unaware of the content of the continued conversation.

The shoe was still in his hand, and Tuck looked up from his position on
the floor for some level of guidance as to what he was doing there.

Debbie broke her conversation with Jake. “Excuse me for as second, Jake.
I need to give some instruction to Mary Anne,” her hand now covering the
receiver, effectively muting the call and Jake’s ability to hear her

“Mary Anne, I want you to lick my shoes clean. I want your tongue to
clean away any dust, dirt or slime that happens to be on my high heels,
and then you are going to suck on the heels until I am finished talking
with your boyfriend. Are there any questions or comments, or argument?”

Tuck looked at the shoe and then up at Debbie, still with her hand over
the phone,


Tuck put his tongue out and touched the shiny black leather.

“He is right here; I can have that conversation if that is what you would
Tuck pulled his tongue back into his mouth and steeled himself for the
additional humiliation that seemed to be more and more a part of his

“I’m waiting.”

He closed his eyes, opened his mouth and let his tongue come out flat
against the hard leather. He thought he could taste the black that was in
her heart, and took a long slow and wet lap across the toe.

“You will have to do better than that.”

He couldn’t believe her words. How could he lower himself any more than
he already was? But Jake was on the other end of that line. Again he felt
the taste of leather. He slowly licked across the toe of her black,
shiny, high heel shoe.

Debbie went back to her conversation in hushed tones, a near whisper, so
that Tuck could not hear.

His tongue glided across the smooth leather and high gloss over and over
again. He lost the battle and was now confined to an even lower position
than he thought possible. His only thought was to avoid a black mark with
Jake, so easily delivered and so easily devastating. He watched himself
as in a mirror, holding the shoe in his hands as he covered the surface
with his hot slick spit, his tongue making the surface shine through the
thin coating.

The taste and grit filled his mouth. He wanted to spit, but instead he
swallowed several times trying to remove the foreign debris that he had
collected. She presented the other shoe to him casually, as if this was
an everyday occurrence, his new position in life and his new

Without a word he started to bathe the second high heel with his tongue,
his eyes closed as he let his tongue lap across the toe.

“Jake, one second. I need to correct Mary Anne once more.” Her hand
covered the microphone pickup once again.

“Suck on the toe, like it was Jake’s cock.”

Tuck looked at her like she was crazy. She made a move to take her hand
off the microphone, letting Tuck understand her next comment would be
live and not be in Tuck’s best interest. She waited.

Tuck opened his mouth, inviting the shiny black leather to enter. She
pushed in and out with the narrow toe, advancing into his mouth more on
each new entry. The bottom of her high heel was now in Tuck’s mouth, the
taste of the world now on his tongue.

She smiled down at Tuck, watching him give such intimate pleasure to her
black pumps. Satisfied with his efforts to please, she turned back to her
conversation with Jake.

“Yes, I think for the most part it is going quite well this morning.” She
made sure Tuck could hear the words of her partial and incomplete
approval. Her voice then went back to hushed tones and Tuck was no longer
privy to the conversation.

The toe was completely saturated with his spit, and the last of the
debris had been soaked free with his efforts. She pulled it free, re-
crossing her legs so that now the other shoe was in front of his face. He
took the toe into his mouth again without argument, his eyes closed as
the biting taste filled his mouth.

She casually let the shoe slide in and out enjoying the control and
domination as she finished her conversation with Jake.

“Yes, perhaps that’s best.” Tuck listened closely, his mouth still full.
“15 minutes before 9 should be no problem, we’re getting close to having
him dressed and out the door now.” She said this while taking her free
foot and pushing it into his crotch area, the camel toe look offering a
perfect target. “Yes, I’ll see you then.” She pressed the red end button
on the phone and laid it down on the side of the bed. “I guess you’re
going to find out firsthand what happens to naughty little girls.” She
watched as Tuck continued his tongue bath on her shoes.

“The heels on these are a bit thicker than most of my collection,” she
pulled off the shoe slick with Tuck’s hot spit, “and I wore them special
for you. I call them cock heels, as the heel is almost as thick as a
man’s penis. It’s even shaped correctly. They really are quite naughty if
you get a close look at them.”

She took her foot away from Tuck’s attention, presenting him with the
heel of her shoe. “What do you think, Mary Anne, is this the size of a
man’s cock? Not yours, of course, but a real man? And I can tell you from
experience certainly not Jake’s. But it’s not a bad starting point for a
beginner. Oh I forgot, you’re not exactly a virgin, are you?” She played
with the heel, touching Tuck’s lips, teasing him with it. She would pull
it back, and then present it to him again, and then she finally pressed
it firmly against his lips, opening them and forcing him to take it

Tuck’s mouth and tongue were immediately covered with the grime and grit
from the shoes heel point, the rounded crown of the faux cock forcing its
way to the back of his throat. He gagged once as she thrust deep, and
then pulled back slightly allowing him to recover.

“Do the other one, too.” And without preamble she exchanged positions,
and the other shoes cock heel found its way into Tuck’s soft mouth. She
smiled as she pumped her foot in and out; the heel’s skin dripping Tuck’s
spit on to the rug. The ultra-naughty shoes at first looked only like
they had a stylized ivory colored heel; but up close, as Tuck was seeing
them, they had an all too real and all too familiar profile. He had no
choice but to continue to lavish his attention on them, back and forth,
as he washed away the grime and other refuse that had collected, leaving
only the smooth polished surface wet with his spit, dripping with his
attention and servitude. In and out, one shoe then the other, until she
grew tired of the game.

“Enough play for now.” She pulled the spit slick cock from his lips and
looked down at him, the drool coating his lower lip and chin. It was a
pleasant sight, Tuck still just wearing his panties, his body so smooth,
girlie, no hips no bust. Maybe she could do something about that, too.
The cock heels were soaking in his spit, and she loved seeing them slip
in and out of his mouth. One day soon she hoped she would be watching
Jake’s hard cock slip in and out of Mary Anne’s lips. Yes, that would be
a true revenge, and she would have proof of who he really was.

“Get dressed. I have to get you to the spa as Jake wants to have a few
words with you.”

Tuck didn’t like the way that sounded and resigned himself not to piss
off Debbie any more this morning. He was going to be the most compliant
he could be. He swallowed again, afraid to spit out any of the offending
remains from her shoes. He gathered enough spit to wash away most the
remaining taste.

The clothes remained on the bed, and in his normal way of getting
dressed, he always put on underwear, t-shirt and socks before anything
else. He already had the panties on, so he looked on the bed for a t-
shirt. It wasn’t there, but there was something that matched the panties

“Here, let me help,” Debbie said, picking up the garment and holding it
by the spaghetti straps in front of Tuck, who was still on the ground at
her feet. She let the silky teddie float down over his head and helped to
adjust the straps so that the bodice was in the right position. Even
without breasts, his bare nipples and little man tits puffed the garment
out in the right places.

“Stand up and look in the mirror.” She allowed Tuck to rise, and he
walked over to his closet door in which a full length mirror was

Normally the large mirror showed him in his rough state, where he quickly
could decide if there were too many holes in his jeans or if the shirt’s
food stains were acceptably not noticeable from the distance shown in the
mirror. However, this time the reflection told a noticeably different

“How adorable.” Debbie had come up behind Tuck as he looked at his
reflection. With her heels making her 4 inches taller, he looked like a
little girl standing next to her mommy. “We’ll put your hair into a nice
ponytail to keep it out of the way, it won’t look that feminine,” she
laughed, holding his hair in her hand in a makeshift band of elastic. It
was evident that she was holding his blonde hair high on his head so that
the ponytail would look anything but feminine. “See, that will look very
nice.” She used her hold on his hair to turn his head back and forth so
she could study the image. “And I have some new earrings for you today,
as well.”

Tuck was not going to let the witch get him angry as he was already
scheduled to have a conversation with Jake, and making it worse did not
seem like a good idea.

“Sockies are next,” she said, going back to the bed and picking up a pair
of white socks. They had pink ribbons around the ankle. “Don’t worry,”
she said, playing with the little bows as she handed them to Tuck, “the
jeans will hide any evidence that these are little girl socks.” She
watched him pull them on to his bare feet. “What I really want to see is
how Lawrence altered your jeans custom for you.” She handed the jeans
over to Tuck next.

Tuck took them from her and knew immediately they were going to be tight.
The legs looked impossibly skinny and the waist couldn’t possibly be his
size. He turned it this way and that trying to figure a way to put them
on. Besides the fit, something else didn’t look right. Debbie took them
from him and turned them around and handed them back, the zipper was not
in the front, it was in the back. He sat back down on the bed to draw the
pants up with Debbie snickering and enjoying the show. Having the little
white socks on made pulling the pants up easier, but it was still a
struggle and the material hardly gave at all. Finally, after much tugging
and pulling, he had them up and over his bottom and was ready to zip them
up. He couldn’t reach the tiny zipper until he stood back up.

“Here, let me help.” Debbie turned him around. “Suck it in.” He took a
deep breath, holding in his already slim stomach as Debbie zipped him up.

“Oh my god, that’s too tight,” Tuck said, letting out the air and
expanding his waist as much as the confines of the jeans allowed.

“You’ll get used to it,” she said in a matter of fact tone. “Now for this
cute blouse. Notice the buttons are on the girl’s side.”

Tuck took the blouse from her and quickly noticed that the buttons were
indeed wrong, well wrong for a guy. It was another one of Lawrence’s
creations. He had taken the darts out, well almost all out, so that only
a little pouch was left for his man boobs. It also fit snugly, but the
buttons, once he had them figured out, attached well and did not pucker;
another of Lawrence’s magic touches.

“Don’t worry about tucking it in, it’s meant to be on the outside.
Besides, if you move just right, it will show off that sexy belly of

Tuck turned back and forth in front of the mirror and it took no effort
at all to show off his bare midriff.

‘Okay, let’s do your make-up. I want you to look great for Mrs. Getty.”

Tuck was afraid of what he was going to look like but was in no position
to argue. So he just stood and followed her back into the bathroom again
and took a seat at his man vanity. It was not a woman’s vanity, it was
designed for a man.

“God, Mary Anne, you have more products on your vanity than I have at
home. But don’t worry, I have all new items for you,” as she took one
after another of the bottles that lined his vanity saying ‘just for men’
and dumped them into the waste container at the side of the table.

“Let’s start with a very light coat just to hide any imperfections,” and
she was off and running, using all of her magic to make Tuck look overtly
handsome, bordering on pretty. She provided a play by play of the
transformation, “A dusting of blush and a hint of mascara, and last but
not least, a pale pink lipstick.” The band of material that she chose for
his hair was flowered and held his now golden hair in a tight hold,
creating a flouncy ponytail high up on his head.

“I thought about braiding your hair, but not this time. Maybe another as
we need to hurry if we are going to get to the club in time for you to
chat with Jake.”

The mirror showed what could have been coined as an optical illusion. In
one way of seeing, you could easily see a young girl sitting at her
vanity, and then looking a little differently, perhaps to the side, the
image was of a handsome young man. The duality was quite disconcerting,
and he was sure that most would see a feminine persona in either case.

“Now for the last touch, and these are quite new. In fact, you will be
the first to ever wear them.” She pulled a black velvet box out her bag,
and in a flourish, she presented it in front of Tuck, opening the box to
revel the contents proudly. “Voila, my latest creation.”

Inside the box it looked like a collection of stars, until she gently
picked one up to show Tuck closely. The gold star was the stud and
hanging off of it were many different strands of smaller stars. It really
was a beautiful piece of work, and Tuck was a bit surprised that someone
like Debbie could have designed it and created such a piece of art work,
but it was certainly not anything that he would wear. The thoughts
rambled in his head as he watched her take the gold pins and thread them
though the holes in his ears, first one side then the other.

His every movement caused the stars to tinkle against each other and move
freely. He wondered if anyone else could hear the noise. And musical,

His question was quickly answered.

“Oh they look so sweet on you, and they match the stars on your fanny.”

Tuck had not noticed any design but stood again with with his back to the
mirror and twisted around to see what she was referring to.

Across his bottom, starting at each pocket, were a line of tiny gold
stars exactly matching the ones adorning his ears. The way they were
placed accented the line of his bottom in the overly tight jeans. He
turned back around to look at the whole affect. It was not him in the
mirror. He turned back and forth looking at the person he could not
identify; not girl, not man, but something in between. This person was
very attractive, but just not Tuck. He thought, ‘Well, maybe that wasn’t
such a bad thing’.

“I just love the way those look on you.”

He wasn’t sure of what item she was refereeing to, as it was all new to
him. What was most evident to him was the lack of even the slightest
bulge at his crotch. No evidence at all of his own manhood, only a little
mound exactly where it should be… for Mary Anne, but not Tuck.

“Ok, no more dawdling, we have to move now. Put on your shoes and get
your purse.”

What shoes, was he supposed to wear? The only new ones he had were what
he wore last night. And Tuck didn’t own a purse.

“I don’t have a purse.”

“Of course you do, it’s there on the bed.”

Tuck looked on the bed, having not noticed it before, but there was a
leather satchel, a man purse with a thick leather strap. It was smaller
than what he had thought a man purse should look like, and it was adorned
with the same stars in his earrings and on his pants. “You really have to
thank Lawrence; he went to a lot of extra effort to modify that purse to
match your pants and the earrings.”

“Yes, I have a lot to thank him for, I’m sure.”

“No attitude, young lady,” she laughed, using his Mary Anne sex openly
like she was. “And Mary Anne, I expect you to thank Lawrence very well.
I’ll be there to make sure you do.”

Tuck didn’t say a thing as he slipped back into the shoes from last
night, having somewhat adjusted to the slight heel, and picked up the
purse. It was heavy. “What’s in here?” he asked.

“Everything you’ll need for the day; make-up, lipstick, a condom, breath
mints, a dildo, lubricant, and assorted other things a young lady can’t
do without.” She made sure he didn’t open it and watched him sling it on
his shoulder.

“Good, we’re ready to go. Those shoes really don’t go with those jeans,
but I’m sure Mrs. Getty will make that her first stop. I’m very
interested to see just what she recommends.”

In the next five minutes they were out of the house and into Debbie’s
car, a cute little Volkswagen. Conversation was at a bare minimum, and
before it could get any more uncomfortable they had arrived at the club.

“I’ll see you later tonight at the Getty’s for dinner. Be a good girl and
don’t embarrass Jake too much.” She reached over and opened the door and
invited Tuck to leave the car.

Tucked turned and stepped out only to have his hand taken once again by
the doorman, even though he was in no danger of slipping or falling.

“Mary Anne, you look lovely this morning.”

Tuck was too tired to correct the obvious mistake and let the man lead
him to the already open doors, releasing his light grip and letting Tuck
step unassisted into the brightly lit but nearly deserted foyer.

Another young man stepped up, garbed in the same uniform, and handed him
a card with his name on it. This time it was spelled correctly.

“Thank you,” Tuck said softly, taking the card and immediately
recognizing Jake’s very crisp writing. ‘Engineer writing’ he called it,
easily read by anybody and forever logged into the countless log books
neatly cataloged in his library. It read “Marion”, then neatly below that
the number PL 14. “There is a need for an immediate conversation.” A line
was skipped and the signature was simply, “J”.

Tuck closed his eyes and was rubbing his head in thought. ‘Now what? Is
this odd experiment over, or is it the friendship that’s over.’

“Anything wrong, Miss?”

It was the voice of the young man that had given Tuck the card. Tuck
opened his eyes, looked at him and thought, ‘doesn’t anybody see me as a

“No, nothing, just tired I guess. Do you know what PL 14 is?” he asked,
showing the card to the young man, oblivious to the fact that he could
easily read the rest of the message.

“Oh yes, private lounge 14. You must be Marion.” Tuck smiled as he had
pronounced his name correctly. “Jake is waiting for you there. He said to
expect you and to help you locate the room if you had trouble, but it’s
around that corner and ise the third door on the left. They are clearly

“Thank you,” Tuck answered, glad that he could move off on his own and
meet Jake without a further audience.

The room was not hard to find, the thick carpeting muffling any sounds as
he approached the closed door. There was a card slot filled with the word
‘Private’, and a second that said ‘In Use”. He checked the number once
again on the card and the number on the door and they matched. He knocked
lightly on the door.

“Come in.” It was Jake’s voice, deep and resonant. It seemed a deeper
base through the filter of the door, but it was definitely Jake. Tuck
took hold of the brass door knob, turned it smoothly and stepped into the

It was about three or four strides long and wide. There were no windows
and the walls were covered in red drapes. The floor had a contrasting
design, but it was muted and hard to make out. There was a leather couch
on one wall and two plush wing chairs on the other end, and in the middle
was a chair that held Jake. The muted light made him look even larger,
and Tuck could see that there was no smile on his face.
“Marion, turn around.”

Tuck did a slow turn in front of Jake. He could feel Jake’s glare and
anger vibrate across the room.

Jake was in no mood to give compliments, he simply uttered a single word,

“Thank you. Debbie really…”

Jake interrupted, “You’re not here to talk, you’re here to listen.”

Tuck stopped in mid-sentence, waiting for the words of finality and

“I cannot begin to tell you how disappointed I am right now. The reports
I’ve been getting have been most disturbing. Even yesterday, here at the
spa, you were anything but gracious and cooperative. And then last night,
in the kitchen, the chef tells me you were even rude and condescending.
And then again this morning with Debbie… is there no end? I have had it!
I would tell you this little experiment is over right now.”

Tuck’s eyes began to tear up, it really was over. His body slumped at
thought of the loneliness that would be his life.

“I would, but I can’t, not right now, as you did make one good point in
all of yesterday, and that is Mrs. Getty. She really enjoyed you and,
well, I’m not going to take that away from her.”

Tuck was not sure if that was just a temporary reprieve or a way back
into Jake’s good graces.

“I just can’t condone this type of behavior. These are my friends, people
I rely on, and to have you treat them with that level of rudeness… it
just cannot be tolerated.”

“I am so sorry, Jake. I have so much to learn not to be my old me.”

“You’re a petulant child,” Jake went on as if not listening, “an
obnoxious little girl who deserves a spanking.”

“I’m so sorry, Jake. I’ll try to do better.”
“Come here.”

Tuck stepped closer, not knowing what was going to happen next.

Jake reached out, grabbed Tuck’s pants by the belt and pulled him
directly in front of him. Wordlessly, Jake undid Tuck’s belt and then
reached around and behind and pulled the zipper down. He then grabbed
hold of the pants in both hands and pulled them down. The sudden move
pulled both the pants and Tucks panties down together, leaving Tuck naked
from the waist down, the jeans now around his knees. The very small penis
was well hidden, barely peeking out from between his smooth thighs.

Jake turned Tuck around, the pants making it difficult to move, and in
one motion landed Tuck across his muscled thighs. Tuck’s naked and pink
bottom was now positioned over Jake’s lap, his legs on one side and his
head dangling down the other. Instinctively Tuck raised his hands to
protect his bottom, offering the perfect chance for Jake to capture both
wrists together in one hand, holding them tight and up towards the middle
of Tuck’s back.

“A petulant child,” Jake said again, his hand rising and coming down with
a hard finality and loud crack.

Tuck heard the noise as his bottom jiggled with the impact, and then a
split second later came the pain; it was intense and highly localized. He
gasped and yelled a guttural noise without vocabulary and before he could
get his breath to yell stop and second impact came and the pain doubled.
His arms tried to move, but the vice-like grip that Jake held them with
would allow no escape. A third time Jake’s hand came down, and Tuck could
hardly get his breath. He felt like a flaming hot poker had been laid
across his bottom. A fourth came slamming down. Tears welled up, but
still no words, just the terrible yell from deep down in the pit of his
stomach. A fifth horrible strike, and finally the first words, “Stop…”
came up from somewhere. Before he could even finish that single syllable
word, a sixth blow was administered. He struggled in vain, trying to lift
his head up off the floor, but Jake’s grip became even more tight and
painful, pressing him down on to the lap. Tuck’s bottom was aflame, his
breath coming in short pants and his eyes full of tears. There was a
pause, and Tuck thought that maybe it was over.

“Do you promise… (smack)… to be… (smack)…a good... (smack)... girl from
now on?”

“Yes Jake, I promise,” Tuck barely managed to get out between sobs.
Tuck wanted his punishment to end. He started to feel Jake’s grip lessen
and he thought he could move, but the grip tightened once again and
pressed down. And then Tuck felt what was pressing back up. Hard and
stiff pressing against his own little toy was Jake’s massive cock tight
inside his pants, excited and stiff. Jake did not loosen his grip. “I
will not tolerate this level of behavior again.”

“I promise I’ll be a good...” Tuck was not sure if he should repeat what
Jake had described him as, if that was just a slip or was it real? He
closed his eyes. Perhaps the slip would be seen for what it was, a
mistake, or perhaps the mistake would be in not repeating it, which would
translate to this position over his lap, naked… “girl. I promise to be a
good girl from now on,” Tuck’s voice clear as the spanking and the pain
were subsiding.

Jake still held Tuck down firmly, not realizing he was grinding Tuck into
his stiff and excited cock. “That pleases me,” Jake said slowly, his hand
raised high over Tuck’s naked bottom, the color now fire red with his
handprints clearly seen on the white bare skin. “I don’t want you to
forget it, either, or you will find yourself over my lap again. His words
now established the normalcy of a spanking for future misbehavior. Jake
smiled at the thought of giving a spanking for bad behavior or attitude.
It intensified the pleasure of control, and he felt the strength of his
hold mixed with the hardness of his cock and the full submission of Tuck
over his lap. He held the hand high and brought it down as hard as he
could, the sound reverberating in the room, the scream from Tuck evidence
of the skill in which it was given.

Tuck couldn’t believe the pain. He couldn’t take any more, and his voice
through choked sobs cried, “Please, no more.” And then again the hand
came down, striking between his legs, catching just below his tiny balls,
finding a new point of pain, and he howled. Twice more Jake’s hand came
crashing down, a full ten times, and then another pause. Tuck tried to
catch his breath between sobs, his breath coming in sharp sudden bursts.
But Jake still held him.

It was almost as if Jake didn’t want to let him go until Tuck had calmed
down, as if he wanted to say this was for your own good. It would happen
again, he knew that now, the rush was far too great not to feel that
power and control again. He still held Tuck, but softer now. He wanted to
feel his bottom, feel the welts he had caused. His hand came down softly,
laying on the hot naked skin, the welts rising, and the smooth skin no
longer smooth, but roughened by the swellings. Red hot was the blood
pouring into the afflicted areas, and he rubbed it softy as if his touch
could take away the pain. Pain that he had given, good measure and
strong, well deserved but now over. He could now forgive Marion, they
could now continue. It was if a magic door had opened and he stepped
through, his anger gone, his disappointment softened. He rubbed the pain
away and heard Tuck moan. He could feel that the pain was dissipating.
His grip lessened even more, but Tuck didn’t move or struggle. Jake
allowed his hand to reach between Tuck’s legs and touch his small balls,
not damaged or impacted, the blows were careful to avoid. ‘This all
belongs to me,’ he thought. His grip loosened completely allowing Tuck to
rise if he wanted, but Jake continued to feel the smooth and hairless
baby marbles, marveling at the texture and his control. He let them go
and put his hands to his side, waiting for Tuck to remove himself from
his lap.

Tuck’s bottom still burned, but the fire was rapidly diminishing. As he
felt the grip loosen completely, he stood in front of Jake still naked,
his hands at his side. He wasn’t sure if he was to say anything.

Jake stood as well and took one step toward the door. He turned back and
said, “There is a bathroom to your right, Mrs. Getty will be here in few
minutes. I will see you at dinner, have a fun day.”

The words were surreal; calm, collected, no anger, no finality. It was
like the clock had been rewound and the day was starting fresh.

“Thank you,” Tuck said standing naked in the room, his little penis still
hiding between his legs. He offered no attempt at hiding his nudity. “We
will... I look forward to dinner too.”

And Jake left the room, closing the door.

Tuck stood in the middle of the room looking back at the door and the
chair for several minutes. Then he pulled up his pants, taking care to
suck in his tummy and settle the pants over his very sore bottom. The
sudden pressure of the pants and the sharp pain quickly went away, and he
walked into the bath room to see what he needed to do to get ready for
what was going to be a very long and strange day. But he smiled in the
mirror as he opened his purse, reaching for the make-up that Debbie had
so thoughtfully provided. There was a tomorrow now, too.

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