Reservations
By Gingerfred Man
Chapter One -- Hotel Management
For many in the sprawling Wisconsin city of Fromage,
the business day was ending. Weary road warriors were
leaving their clients to the comfort of hearth and
home as they slogged off to their dreary hotels for a
couple of drinks at the hotel bar, some ogling of
fishnet-stockinged waitresses and a tussle with a
tough steak, followed by the so-called pleasures of
the hotel room -- a couple of hours watching sitcoms
and reality shows, a far-less-than satisfying wank,
then sleep.
But Norm Jordan's workday was just beginning. As
manager of Fromage's City Hotel, he was proud that his
guests could look forward to a night far superior to
the usual fare to which a traveling businessman had
been previously doomed.
The brainchild of Dick Devine, a crossdresser who
spent 150 nights a year on the road, the City Hotel
offered things that made businessmen eager to stay
there and reluctant to go home for weekends.
Norm knew very well that frequent guests had nicknamed
his hotel the "Clitty" Hotel and he was proud that
they had.
All must be in order for the guests, so he began his
daily tour of the accommodations. The guest rooms,
which were all above ground level, were a no-brainer.
Just a regular hotel with all the usual stuff. The
amenities of the "Clitty" were all in rooms below
ground. Away from peepers and the unhealthily
curious.
Norm walked the subterranean halls and drew in the
smells. Although the place had been thoroughly
cleaned from the revels of the previous night, some
smells would just never leave. Thank goodness. He
smelled the sweet perfume of sissies eager for their
men. The manly, lusty sweat of men hungry for the
soft comfort of a sissy's love. But mostly, he
smelled cum -- hot and musty -- freshly, gently squeezed
from the balls of a panting, gasping sissy at the
pinnacle of her pleasure -- teased, licked, sucked,
squeezed and rubbed from men urgently spilling their
hot loads on, in, over and around gleeful sissies.
This was Norm's world and he was proud to be part of
it.
Chapter Two -- Customers
Tom, Dick and Harry had had a rough day. They had
gotten the 6 a.m. flight from their East Coast homes
and had been working through some rough spots in a
situation their client had made sure was completely
screwed up before he asked for help. And the next few
days loomed poorly as well.
But now that the day was over, Harry and Dick seemed
to be positively joyous, eager to get to their hotel
for what Tom thought would be hours of dull talk with
two guys he had never worked with before. Did they
know something Tom didn't?
The City Hotel didn't look that special. Maybe like a
nicer Holiday Inn, but Harry and Dick always insisted
on staying there when they worked in Fromage. Which
was often.
Tom was not all that happy when he was pulled off his
current projects to assist the two guys on their big
mess.
"You'll be very happy you joined us," Harry said to
Tom.
Tom didn't see how. In his view, Fromage was a
one-horse town and the client was a pain in the ass.
Why did Harry and Dick like it so much?
Tom agreed to drop his stuff off in the room, then
meet the other guys in the bar at 6 p.m. That only
gave him 15 minutes, time enough to wash his face,
take a piss and call his wife. ("So, how was your
day? The kids all right? OK. Love you. Bye.")
With a sense of dread, Tom went downstairs and joined
his colleagues.
The bar was almost empty. Harry and Dick each had a
beer and were standing with a short, middle-aged guy
in a blue blazer, striped tie and khaki pants. He had
a nametag on that said, "Norm Jordan, Hotel Manager."
Big whoop, Tom thought. So they know the manager.
"Good evening, Mr. Echols," Norm said to Tom. "We're
so happy you decided to stay with us."
That was awfully friendly, Tom had to admit, so he
thanked Norm.
"I always give new guests a tour of our facilities.
May I?"
Tom thought, what, the video game room and the hot
tub? What a bunch of crap. But at least he wouldn't
have to talk to Harry and Dick during that time. So
he agreed.
"Right this way, sir," Norm said. Strangely, Harry
and Dick followed, smiling oddly.
They got into a secluded elevator and Tom noticed
three buttons that weren't on his room elevator -- B1,
B2 and B3. Three basements. Norm pushed B3. Tom
smirked. I'm going to see the boiler room, I guess.
No. No he wasn't.
When they stepped off the elevator, Tom smelled the
aromas that Norm had inhaled with pleasure earlier
that evening. He knew they were familiar, but he
couldn't place them. Not unpleasant. Just not
identifiable.
Then he heard the sounds. Squealing. Gasping.
Moaning. Even screaming. Were they showing a video
down there or something?
"I think the best place to begin is in the Daddy
room," Norm said. "For the pleasure of our guests who
are attracted to the notion, we've 'recruited' several
local, pretty, 18- and 19-year-old sissies who want
Daddies."
Before Tom could process the enormity of that huge
concept, Norm opened the door and Tom saw a large,
bright, clean and comfortable room with lovely
furnishings. There were at least ten deliciously
pretty, slim, young girls wearing very little except
dresses so short that they ended just below their
waists, very high heels, silky stockings, garter
belts, pink panties and bras. The girls' faces were
expertly made up and each was cute and sweet. And
randy.
And each girl had a stiff little cock either in or out
of her challenged panties.
Worse, there were several middle-aged men sitting in
different parts of the room. Each had his pants down
or off. Some of the men had a sissy on their laps and
were stroking their girls' little peenies as they
kissed them. The girls were giving their "Daddies"
world-class handjobs as they tongued their Daddies'
open mouths. One Daddy was getting a four-star
blowjob from a kneeling, worshipping sissy, whose bare
bottom and swaying little ballbag were waving at a
stunned Tom.
Seeing the men, three unattached sissies squealed
"Daddy!!!!" and minced on towering heels to the door
to greet Harry, Dick and a shocked Tom.
Norm assessed the situation. Tom knew absolutely
nothing. Why didn't his colleagues at least warn him?
Norm would never understand that aspect of
customers. They always wanted to shock their friends
when they brought them to his hotel.
"Mr. Echols, are you all right? We can leave if you
wish, sir."
Tom was in shock, but at least he knew why his
colleagues picked this place. Harry and Dick were
faggots! Tom tried to be disgusted, but the only
thing he got was hard.
"No, it's OK," he mumbled. More curious than
disgusted, he asked, "Is there more on the tour? I
mean we can come back here later if we want, right?"
"Of course, sir," Norm said.
Harry and Dick knew that there would be no exposure of
their peccadilloes to the bosses because Tom wanted to
see more. Didn't they always?
"Come back, later, Daddy!" the girls said as the
quartet moved out of the room.
They walked down the hall to a room completely unlike
the last one.
It was dark and dank. The walls were filled with
paddles, short whips and large, thick dildos.
Tom was a little scared when they went in, but Dick
acted very strangely. He was wary and nervous. Then
Tom saw why. A forty-something, very hairy, muscular
man in a black outfit emerged from an unseen door.
Dick stiffened.
"Ah, Nancy," the man said. "You come for your
well-deserved punishment. Are these new slaves?"
Dick flung himself flat on the floor, kissed the man's
feet and said, "No Master. Only this worthless sissy
is here to serve you this evening."
Well. That just about blew Tom away. More so than
the first room, even. Dick was always so butch and
self-confident. What was this "master" crap? And
"Nancy?"
"It displeases me that you show yourself to me in your
male attire, Nancy. You will receive 60 tonight
instead of your usual 50. Now go get dressed."
"Yes, Master," Dick said, then humbly crawled out of a
side door.
Dick was crying, Tom noticed. And Dick's cock was
almost ripping his pants.
Wow.
Tom followed Harry and Norm out of the room. Quickly.
"Does Dick always go to that guy?" Tom asked.
"Usually on the first night we're here," Harry said.
"He adores what that man does to him, but the welts
have to heal before he goes home."
Welts?
"Does Dick really dress up as a woman?" Tom asked.
Norm and Harry looked at Tom as if he were a space
invader. But they answered him factually. "Dick
dresses much sluttier than the girls in the Daddy
room," Harry said. "The sluttier he looks, the harder
Bruno beats his ass. Dick loves Bruno and Bruno loves
Dick. They always end up with Bruno on top of Dick
fucking his sore ass. But only on Mondays."
Yeah, right. Welts.
Tom's head was spinning. The next room loomed. Did
he want to see it or should he bolt, check out, and
head for the Motel Six? Tom was pretty sure that his
Johnson wouldn't be nearly as stiff at any other
hotel, even if they left the light on for you. Plus,
he was curious. He wasn't gay or anything like Dick
and Harry obviously were. But he was curious.
Norm continued the tour. "Gentlemen, this is our
'light bondage' room, as opposed to the 'heavy
bondage' room we just left."
Norm didn't have to say much. Tom could sort of
figure things out.
Guys in make-up and lingerie (most were in stockings,
heels and baby dolls) were tied up with satin hankies
or thin ropes. Most were on their backs, tied to
bedposts. Or on their stomachs, tied similarly.
Tom shuddered as he saw the hotel guests'
helplessness. Some had ball gags. Others had satin
gags. Some preferred no gags. The situation seemed
to be dictated by the "victim."
There were 12 beds scattered around the very large
room, as well as chains attached to walls, and even a
sawhorse or two for the truly adventurous.
Nearest to Tom was a pretty young man lying on his
back. His pink nightie was pulled up to his waist and
his thick cock and large balls were exposed and
throbbing. He had pretty pink stockings on, as well
as strappy pink sandals with a thin, five-inch heel.
He was completely restrained, so that he was only able
to move an inch or two in any direction. His mouth
was free, but he was silent. His eyes showed a
compelling combination of fear and lust.
Tom also recognized a businessman who had been in the
lobby when they were checking in, less than an hour
ago. The man looked quite different from how he had
been in the lobby. For one thing, the man was quite
naked. Tom noted absently that the man's cock was
smaller than the "girl's," but that really didn't
matter. The man was in charge.
He was driving the sissy wild by kissing "her" nipples
as he stroked her cock. She was whimpering and
struggling against her bonds. She said "No. No. Let
me go, you beast."
The man paid no attention. Instead, he produced a
small bottle of lubricant and began to rub it on three
of his fingers.
"No!!!!" she screamed. "No!!!!!! You're not going to
fingerfuck me, you brute. I won't allow it."
Of course the man proceeded to do just that, licking
her nipples as he was running his thick fingers in and
out of her tiny pootie. She cried and screamed and
begged for him to stop. Then she locked eyes with Tom
and said, "You! Please make him stop. Let me loose.
Help me, please!!!!"
Tom was moved. He looked at Norm and Harry who
weren't doing anything. Why weren't they?
Norm noted Tom's agitation. "It's all right, Mr.
Echols,' Norm said. "It's all part of the game. If
Kimberley wanted Ralph to stop, she would only have to
say her 'safe word' and Ralph would stop immediately
and untie her. Kimberley's having the time of her
life, see?"
Tom looked at "Kimberley" just in time to see her
spraying thick ropes of cum all over her stomach and
chest. Then Ralph climbed on top of her to kiss her,
then feed her his cock. Which she licked and sucked
with intense enthusiasm.
"Safe word," Tom said to Norm. "What a concept.
What's the word?"
"Everyone chooses his or her own," Norm said. "Though
most here use a word not used in polite conversation,
like 'Rumpelstiltskin.'"
Good choice, Tom thought. He wasn't sure if that
whole helplessness and submission stuff appealed to
him. But the people involved seemed to be having a
pretty good time.
"Next room?" Norm asked.
Why not? Tom decided.
Harry said, "I'm going to leave the tour. Tom. I'm
going up to B2 for a girlish makeover, then to the
lounge on B1 for some flirting. In case you didn't
notice, B3 is the unusual stuff. B2 is where we get
girlied up. B1 is a big social hall with drinks and
dancing and a lot of matchups for the night."
"True enough," Norm said. "I'll just show you one
more room and then we can talk about what you would
like to do. If anything."
"OK," Tom agreed.
The last "odd" room was, perhaps, the oddest. Seven
or eight hotel guests were dressed as young girls.
Really young girls. In party dresses, petticoats,
crinolines, bare legs, frilly socks and Mary Janes.
There were close to an equal number of guests still
dressed as men and they were showing the "little
girls" quite a good time. Some girls were sitting on
Daddy's lap, kissing him as they stroked Daddy's
exposed cock and Daddy fondled them with his hand in
their panties. Other Daddies had their "girls" on
their backs with their legs in the air. Those daddies
were plowing their girls' "pussies" quite
purposefully. And the girls were squealing out their
enjoyment.
Norm and Tom didn't stay long in that room.
As they strolled to the elevator, Norm asked a very
agitated Tom, "Any preferences?"
Tom gulped again. "Could I go back to the first
room?"
Norm smiled. "You want to be a Daddy for a pretty
young sissy?"
OH!! Did he!
"Uh?yes. Is that OK? Are there any free? I don't
mean free. I mean available. I'll pay if I need to."
Norm smiled. "Sir, there's a surcharge for
'entertainment' on the room -- $125 per day. There
are no other charges. Please, sir. Enjoy yourself at
City Hotel."
Norm led Tom to the door of the first room and opened
it for Tom.
Tom sighed and passed a door into a new life.
Chapter Three -- Staff sissy
To say that Megan Brennan was eager to please would be
like saying that Chicago Cub fans are masochists.
Megan was frantic to please and be pleased by a loving
Daddy.
At work, she was dull old Ronnie, a schmoey, male,
video-store manager. Two or three nights a week, when
she got off work, she was Megan --super sissy and
pleaser of daddies at the City Hotel.
Her own Daddy was not nice to her, ever since she was
14 and he caught her in bed with the paperboy, sucking
his cock. She was wearing one of Mom's pink nighties
and Mom's red lipstick and she looked so hot that
Jake, the paperboy, creamed his pants when he saw her.
Then twice more when she sucked out his twinkie's
cream filling. Daddy caught them just as she was
cleaning Jake's cock off tidily with her tongue.
Daddy had raged and kicked Jake in the bare bottom,
throwing the naked boy out the front door in broad
daylight. Daddy didn't care. Then Daddy beat Megan's
bare bottom hard. No pleasure to it. Just pain.
The worst was that night when Mom and Daddy had an
awful fight. Mom defended Megan and Daddy struck her.
Daddy was sorry after, but Mom kicked him out of the
house and Megan and Mom never saw him again. That was
sad, but Mom remained supportive of Megan all through
school. And her torrid, but brief love affairs with
boys and men. Megan was taking hormones now that she
was 18 and soon Ronnie would disappear forever.
The day after her 18th birthday, Megan started going
to the "Daddy" room at the City Hotel. Everyone in
Fromage knew about it. Lots of locals would stay
there overnight, especially on weekends. It was fun!
Megan was probably looking for the Daddy who rejected
her. That was what the manager, Norm Jordan, said
when he "interviewed" Megan for a "position" in the
"Daddy" room. Mr. Jordan alone was worth the
experience. He was a skilled and giving lover and
assured Megan that the Daddies she would meet at the
hotel would be cut from the same cloth as he was or
would no longer be welcome.
Mr. Jordan was right. Two or three nights a week, the
little angel would report at 3 p.m. for a thorough
salon makeover. Hair, nails, facials, make-up. Wow!
Megan looked so hot. The lingerie they lent her
excited her too. She loved the lacy training bras
they hooked over her budding breasts. The silky
fabric caressed her big, dark nipples and the
sensitive, expanding flesh under them. The panties
were incredible. The friction of pure, decadent silk
against her tiny sissy wee and her pretty, pink bag of
jewels. Megan often needed fresh panties, even
before the daddies arrived from their long workdays.
Megan adored sheer, silky stockings, especially tan
stockings with seams. Strappy sandals with "bad-girl"
five-inch stiletto heels. And a ruffly white garter
belt, the thought of which stirred her sissy
testicles.
The dresses the "girls" in the Daddy room wore were
very naughty. The kind girls wear to birthday parties
until they're ten. But much shorter. So short, they
showed a girl's entire panties, stocking tops and
garters. So short, they revealed the girl's tenting
of her panties when she saw a handsome Daddy.
Megan loved the outfit.
The Daddies loved Megan. In the four months since she
had turned 18, Megan had entertained 30 Daddies, some
more than once. Mostly she just played tickles with a
man in the Daddy room. Sitting on his naked lap.
Gasping and panting as the Daddy praised her beauty
while kissing her and wanking her popsy.
Sometimes she went upstairs and spent the evening with
a Daddy in his room, but she went home by midnight.
Once she spent the whole night with a very nice Daddy.
Right after that, his company transferred him to an
account outside of Fromage. Megan and the Daddy were
heartbroken. But Megan made new friends easily.
That Monday night, Megan worked an afternoon shift at
the video store and didn't arrive for her makeover
until 5 p.m. That meant she wouldn't get to the room
until 7, which meant that all the good daddies would
probably be gone. She almost ditched the idea,
trading the possibility of carnal ecstasy for the sure
thing of her couch, hot tea and bad sitcoms.
Later, Megan was very glad she didn't. So was Tom.
Chapter Four -- Matched
As Tom and Norm stood outside the Daddy room, Tom's
stomach fluttered. Norm understood that Tom was
having the usual thoughts of a first-timer as City
Hotel patron. Am I gay? Why did my dick petrify when
I saw what I just saw? Am I gay? How did those
sissies get to be so beautiful and feminine? And, am
I gay?
Norm empathized with Tom. He had had the same
thoughts when he first took the job. But since then,
he had been pounding sissy ass during most of his free
time -- and he had never been happier.
Norm's only concern was that the sissies in the Daddy
room, the "Pirates of the Caribbean" equivalent, at
the "theme park" that he ran, had all been spoken for.
Norm's fears were realized when he and Tom entered an
empty room.
Rats.
Tom was devastated. He had convinced himself that a
nice, girlish sissy was exactly what he needed more
than anything. Now there were none.
And then there was.
The door opened and a rushed, late Megan entered the
room and saw Norm, whom she knew, and Tom, whom she
didn't.
Tom gasped when he saw the radiant angel. All in
pink. With white bows and ribbons and lace. A dress
so short, he could see her tan stocking tops, white
garter belt and pink panties. Tom could also see a
tiny, pantied cock expanding into a little tent when
Megan met Tom.
Megan gasped when she saw Tom. He was delicious.
Middle-aged. Daddyish. Handsome. Turned on by
Megan. And obviously a first-timer.
When Tom saw Megan, he flashed back to some of the
naughty books he had read over the years, and some of
the naughtier dreams those books had engendered.
Pretty boys -- young and girlish -- scantily clad, with
sharp little "points" in their sissy panties. Boys
with full lips and long lashes, surrendering their
bodies to Tom's overwhelming masculinity. The
ultimate conquest -- another, lesser male. Submitting
fully to your superior maleness. Tom thought of
pretty boys with wet mouths, hungry for Tom's kisses
and his cock. Boys with tight little boycunts, hardly
concealed by their sheer, pink panties. Boys gasping
with lust as Tom brought them pleasure and spewed out
his own spunk again and again.
As most men do, since he was a teen, Tom had tried to
reject that lovely vision, which, nevertheless, was
deeply rooted in his masculine DNA.
But visions return. And they can make a man hard and
primal, drawing on ancient instinct as they choke him
with need. The satisfaction of a deep urge can only
be accomplished in one way. And that gorgeous one-way
was standing before him and calling him --
"Daddy!
"Oh, Daddy, I'm sorry I'm late. Please don't be mad
at your little girl, Daddy. You can spank me if you
want. I deserve it."
A spanking!!! Tom groaned internally and his cock
stirred. This perfect creampuff would even submit to
me that way, he thought. Tom shuddered with lust.
Norm stepped in lightly. "Well, Miss Megan, I
certainly agree that your daddy should spank you.
Keeping him waiting was very naughty. Perhaps you
should sit on his lap and tell him all your girlish
secrets. Maybe he'll forgive you. You could start by
giving your Daddy a nice kiss. Goodbye everyone.
Enjoy your evening, Mr. Echols. Miss Megan."
And Norm left.
Megan and Tom were alone in that big Daddy-Sissy
fetish room. Together.
Megan and Tom were both quite tall. He was six-foot
one and she was five-eleven. With her five-inch
heels, she was three inches taller than he. Though
everyone is the same size in bed.
Tom cleared his throat. He seemed about to say
something, but Megan wanted to do something less
verbal. So she stepped over and gave Tom the wettest,
tonguiest kiss of his life. Good golly. He almost
spilled his load right then.
Megan was hot! She was a fantastic kisser and Tom,
once he got the hang of the situation, was pretty good
himself.
When they broke the kiss, they were both panting and
gasping.
Tom couldn't believe his good fortune. Neither could
Megan.
Tom asked, "You're a wonderful kisser, Sweetheart.
Would you like to spend some time getting to know your
new Daddy? We could talk. Get to know each other."
Megan batted her eyes shyly and said, "OK, Daddy.
But, Daddy?"
"Yes, Kitten?"
Megan liked that. Kitten. Like "Father Knows Best"
or something. "Daddy, before we talk, I think you
need to clear things out a little. Your little girl
is worried that you'll injure yourself if you don't."
Tom knew what that meant. "OK, Pumpkin."
Megan squealed happily and seated her "Daddy" in a
nice, comfy chair.
"Why don't we get comfortable, Daddy?" Megan said.
And before Tom could say anything, Megan had her
pretty panties off.
Getting into the spirit of things, Tom took his
trousers off, then his boxers. He sat in a comfy
chair and tried to control his shaking legs. Megan
and Tom sneaked peeks at each other's below-the-waist
nakedness. Both were pleased. Megan's teeny peeny
was pink perfection and her pretty peanuts dangled
delightfully in their pink bag. Tom's manly missile
was only half erect, but gaining steadily. After a
few moments of mutual admiration, Daddy and sissy
joined each other in the chair. Shyly, Megan sat on
Tom's naked lap. She giggled when she felt his
prickly hairs against her bottom. Tom loved the feel
of warm, feminine flesh against his own. Something a
married man feels less and less frequently.
Tom drew Megan to his chest and kissed her with true
ardor. To his own surprise, Tom reached for Megan's
penis. The first penis, other than his own, that he
had ever touched. It was very exciting to do so.
Especially since Megan was enjoying Tom's penile
caresses very much.
She was still kissing Tom, but she was squirming and
squealing as Tom tickled her pricklet and testicles.
Then suddenly, her body stiffened and she began
spurting thick gobs of her fragrant, sticky cream. In
high arcs and little dribbles. Oh, it was a lovely
cumstorm.
Tom was enchanted by the whole proceedings. What had
he been missing all his life?
When Megan's chest stopped heaving, she got on her
knees and began to stroke Tom's nice, fat cock. Tom
was praying he didn't cum before this feminine angel
got his thing between those beautiful, glossed lips.
The little nancyboy surveyed her cylindrical treasure.
Mmmmm. It looked yummy. Long and red, with a big,
delicious, prominent vein. And his balls were the
size of peaches. And just as juicy. She wanted to
empty them again and again. All night long.
Megan held the big pole in her soft hand and squealed
happily.
Geez, Tom thought. What a difference a little
appreciation makes. This doll loves my cock. And
she's not afraid to show it. And she's young and
beautiful. With a cock of her own.
Why aren't there more hotels like this?
Megan pelted Tom's manly cylinder with soft, wet sissy
kisses. Tom's wife Lucy hadn't given him a blowjob in
how long? And had she ever taken the time to do it
correctly like this sweet cupcake was doing. Was she
running her tongue along that vein on the right side?
Oh -- she was! And her long, red fingernails were
digging, ever so lightly into Tom's bag of treasures.
She hadn't even touched the location of most male
brains yet, and yet, he was desperate with need for
her. Oh. Megan was kissing all over his cockhead,
flicking her tongue out to give it tiny licks. Making
eye contact with Tom.
Megan looked so darned happy, unlike Tom's wife Lucy,
who often looked at her watch during so-called
lovemaking. Tom was defenseless when Megan began
swirling her tongue around and around the mushroom's
sticky perimeter. He wanted to guard his cargo a
while longer, but he had never been so excited in his
life. Tom groaned manfully and gasped out, "I'm
cumming, Megan!"
Megan smiled and licked and sucked harder. She was
going to let him cum in her mouth? Or on her face?
Or both. Oh, baby. It was both. A joyous,
exuberant, powerful cum nor'easter. On her face. And
in her mouth, which she swallowed greedily.
As Tom endured the sweet agony of a metamorphic cum,
he thought absently how Megan had done several things
in their first 15 minutes together that Lucy, in 12
years of marriage, had disdained. Dirty things. The
best kind. The kind men adore.
Tom liked the City Hotel.
And Megan liked Tom. He seemed innocent and so?needy.
As if Megan were the answer to a question he should
have been asking all his life.
Megan loved making nice men happy.
Tom drew Megan to his lap and embraced her sweetly.
Even he was surprised when he
kissed her, right through a faceful of his own sticky
juices. He groped her privates as they kissed, a bit
roughly at first, then deliciously as he settled down
a smidge.
Megan kissed Tom back, opening her mouth, offering it
to his penetrating tongue. Tom eagerly fed her his
tongue, then gasped when she sucked it with skill and
a considerable heat.
Oh. The realization slammed into Tom again, as that
evil guy Mr. Shame gains strength after our orgasm.
Tom was kissing another man. Was he gay? He must be
because that "other man" was stroking Tom's thick cock
and he was erect and thinking nasty thoughts yet
again. He wanted to feel Megan's diddle. He wanted
to kiss it, even. And suck her testicles. How close
to the surface had those needs and feelings been all
of Tom's life? He couldn't stop himself. Megan was
so cute. And extraordinarily feminine.
Megan winced a little and made the cutest whimper when
Tom held her closely and once again began to fondle
her "little person." Sucking Tom off had excited her
so that she was stiff, wet and sticky around that
area. Tom seemed to like that.
They were kissing and stroking each other with
mounting heat. Tom had never seen a peener that
small. Not that Tom had been fishing into boys'
panties for very long.
Megan just liked the feeling of being hugged and
admired for her femininity. The peeny tickling was
nice too. Really nice. And Tom was just the kind of
guy she liked. Innocent, handsome, needy and
big-cocked.
The conclusion of such delightful activity is
inevitable. The sweet pantyboy's eyes got wide, she
squealed cutely and her sissy cream simply leaped from
her little pickle.
It was only 8:38 and Tom was having the night of his
life.
Chapter Five -- Got a Light, Sailor?
So were Dick and Harry.
Dick was on his knees, tied to a sawhorse. He was
dressed in a stereotypical hooker outfit, including
six-inch stiletto pumps, and silky, black, seamed
stockings with reinforced heels and toes. His
miniskirt was attached to the back of his blouse with
clothespins and his panties were down to his knees.
Dick's fleshy bottom was elevated and he was
completely vulnerable to a very nasty-looking wooden
paddle wielded by the aforementioned "Bruno."
It's also important to note that Dick was crying and
begging for mercy (though he did not invoke his "safe
word") and Dick's poor asscheeks were fiery red.
Bruno's face was expressionless, though he seemed
pleased when he counted off the last strokes:
"Fifty-nine?.sixty. Very good, Nancy. You took the
last ten, a just punishment for displeasing me
earlier. You took them because you love and respect
your master. You have pleased me."
Through his tears, Dick/Nancy said, "Thank you,
Master."
Bruno nodded. "Tsk, tsk. Those last ten seem to
have done things to Master's favorite plaything,
though, Nancy. Your pretty bottom is red and very
sore looking. Perhaps I won't fuck you this evening."
Nancy cried out, bawling, begging, "Oh, please fuck
me, Master. Please. I beg you. Your lordly cock in
my miserable bottom is my only reason for living."
Bruno smiled. "Very well. First I will apply the
soothing cream. Then I will fuck you until we each
cum twice. Then I will take you to my bed and tend
your wounds until morning.
Dick glowed with love for his beneficent master. And
shuddered at the thought of the intense, sexual bliss
that lay ahead of him that night.
Meanwhile, after an hour of femming up on floor B2,
Harry was walking into the lounge on B1.
Harry wouldn't scare any of the Miss America
candidates, but in a dim room, with eager admirers,
Harry, or Laurie as he preferred to be called, was a
very popular "girl." Laurie was wearing a dark-blue
cocktail dress that had, in a previous stay at the
hotel, been measured, then cut to enhance her body's
best feminine features. She was wearing black, seamed
stockings and moved easily in black, patent-leather,
four-inch-stiletto pumps.
As women had done since the discovery of tobacco,
Laurie sat on a barstool, exposed as much of her long,
nylon-encased legs as decent, and held a cigarette
near her lips.
Four male arms reached out with lighters or matches.
"A good night, indeed," Laurie thought to herself.
Quickly, before the men burned themselves, Laurie
surveyed her admirers. Three regulars and a newbie.
Hmmm. New is good. She accepted a light from the
new, hunky, young man and endured the disappointed
moans from the other gentlemen. She smiled at them
and said, "I'll be in Fromage all week, boys."
That seemed to lift the lads' spirits some, but then
Laurie turned and ignored them, concentrating on the
man who had won her heart for the evening.
Hmmm. He was dishy! Five years younger than Laurie,
perhaps. She guessed 28. Tall, blond and very
handsome. Laurie felt her knoblet stirring in her
black, lacy panties.
"Come here often?" her glib, suave suitor asked
cleverly.
"I cum every chance I get, Honey," Laurie answered. A
nice icebreaker, don't you think?
Next, they exchanged names (his was Trent, or so he
said) and astrological signs. Laurie would have been
bored by all that, but Trent had his big, masculine
hand on the inner flesh of Laurie's right thigh.
Rubbing. Teasing.
He was so forward! Laurie adored forward.
The next thing she knew, they were kissing, with
Trent's tongue halfway down Laurie's throat.
Eager was too mild a word for Trent. Laurie began to
imagine the liberties the naughty man would take with
her lingeried, perfumed body if they went to her room.
She formed a clear, picture of that. Then she
breathed, "Easy, sailor. What's the rush? Are you
double-parked? Why don't you come to my room and you
can enjoy yourself at Laurie's all-you-can-fuck
buffet?"
Trent looked as if he had been told that the Internal
Revenue Service was taking him off their rolls for
life.
As she left the bar, arm-in-arm with her new conquest,
Laurie thought, "One of these days I'm going to have
to stay in the lounge long enough to have a drink."
But who needs alcohol when you have all the
ball-exploding sex you can handle?
Chapter Six -- The First Morning After
When Tom, Dick and Harry gathered at 6:30 a.m. for
breakfast on Tuesday morning, Tom was a changed man.
He didn't even act surprised when Dick stood to eat.
"It's not the swats that made me too sore to sit,"
Dick said. "Master's huge cock was in me most of the
night. Opening me. Stretching me. Filling me with
his hot seed. I have three tampons in there and I'm
still leaking his cum. If I stand, it doesn't seem to
leak as badly. Oh, it was divine!!!!!"
Harry gave Tom a little wink, implying that he and Tom
were the normal ones.
But Tom didn't feel very normal. In fact, he
felt?dirty.
Dirty and astonished at his own sinful behavior. Tom
had sinned lustily and eagerly. He had taken that,
that pantyboy to his hotel room -- the room with the
telephone where he had called his dear wife and
inquired about his precious children. In the hotel
room he had stripped that sissyboy down to her
panties, stockings and garters and kissed every square
inch of the little pansy's soft, creamy skin. He had
kissed and licked her nipples until she screamed and
pumped thick strands of girlish sperm. Then he had
licked it all off her soft tummy. He had taken
her little knoblet into his warm, wet mouth, then
licked and sucked it until it was hard and throbbing
and -- what was her name? -- Megan -- was gasping and
panting and then cumming into his mouth.
What had come over him? Why did he lick out Megan's
"dirty place" when she eased it over his mouth? Why
did he groan and almost faint with pleasure when she
sat on his big, manly equipment, praising its length
and girth, and extolling Tom's skill as a lover.
What skill? All he did was lie there and have the
absolute, fucking time of his life as Megan squealed
and pistoned her perfect bottom up and down on his
stiff cock.
He drew Megan to him for some delicious kissing, which
was what sent him over the edge. Hot globs of manly
semen scorched Megan's inner "pussy" as she screamed
with pleasure and poured out her own tribute to Venus
and Eros.
That was when Tom started added up the sins he had
committed -- adultery, sodomy, and the capital crime of
homosexuality!
Shame swept over him, covering him in a blanket of
guilt. And it wasn't relieved in the least by the
fact that Megan had his cock in her mouth. Cleaning
it. Polishing it. Well, that sort of made a little
of the shame and guilt go away. And the shame/guilt
had all pretty much left the building when Megan's
oral skills got him stiff enough for Megan to climb on
the horsey for another ride.
And what a delightful ride it was. Thirty
libido-feeding minutes and grunts and squeaks and
kisses and licks and feel-ups. Megan, being younger
came first. Thinner and less spectacular discharges
than the last time, but the intensity almost tore her
pretty head off. Then, moments before Tom jettisoned
his own sticky cargo, Megan squealed and shook through
a dry orgasm, the tidiest, but most life-threatening
of the evening. Megan shook like a crazy person as
Tom shot wad after wad of a sissy's favorite enema
into his new friend's comely bottom.
When they collapsed, lying side-by-side, Megan flung
herself into Tom's arms. She was crying as she said,
"You drained me completely. No one's ever done that.
You milked me dry. Every pantyboy's dream and you did
that for me. You're the best Daddy ever!!!"
Well, who among us would not feel the least bit studly
when told such "truths?"
Tom felt wonderful! For about 30 seconds. Then he
started thinking about what he had done. And he felt
awful.
Lesson learned for the men out there? Don't think.
Just fuck.
It was a good thing Megan made the bad thoughts go
away by nursing on Tom's cock until they fell asleep.
When Tom awoke, around 5 a.m., he had a raging
erection. His first thought was that he knew a pretty
bottom where that stiffie would find a good home. But
Megan was gone!
Tom thought, well, that's good, I guess. I shouldn't
have done any of those awful things and I never will
again. I'll go home, confess my sins to my wife, then
join a monastery, where I can repent at leisure.
Then Tom heard the toilet flush. Megan hadn't left;
she was just making tinkle. When she came out of the
bedroom, she saw Tom lying there, awake, on his back,
big cock exposed and stiff. Megan squealed with
delight, then sissy ran to the bed and jumped in.
Seconds later, they were fucking as if their lives
depended on it. Maybe they did.
Tom and Megan had gathered some resources while they
were asleep and it was a lusty, wet and messy fuck.
Followed by another in the shower. Then long, goodbye
kisses as Megan left and Tom got ready for work.
The only time he felt guilty was when he wasn't
fucking Megan. That should have suggested a strategy
to our hero.
At breakfast, Dick and Harry were relentless in their
pursuit of details about Tom's night. He didn't give
many, but they got the drift that he had enjoyed his
first night in the Clitty Hotel much more than they
had hoped.
To draw a bit of attention from himself, Tom asked
Harry about his night.
"Oh, it was a good one," Harry said. "I got femmed
up, picked up a hunk named Trent in the lounge on B1
and took him back to my room. Or was it his room? To
tell you the truth, I swallowed so much semen that my
mind's a bit foggy."
Dick seconded that motion. "I know what you mean.
Have you guys decided what you want to do tonight?
I'd like to do another night with Bruno, but I don't
think my bottom can take more blisters. Maybe I'll
just girlie up and hit the lounge on B1."
Harry said, "I may do a turn in the fetish room
tonight. Haven't decided if I want to be one of the
men or the girls. I may just go as a man and have a
couple girls tie me up and tease me till I'm dry."
Then Dick and Harry looked at Tom. "What about you,
Tom?" Harry said.
Good question. "I don't? I mean? Maybe Megan and I?"
Dick smiled. "You can't see Miss Megan two nights in
a row, my boy. She can't participate in things at the
hotel two nights in a row. House rules. You need
variety or you dilute the experience."
Tom's heart sank. Why did it do that? No Megan?
"Maybe I'll just stay in my room and watch
pay-per-view movies," Tom told his co-workers.
Harry and Dick snorted. "Yeah, right. You're new.
You feel shame. It's natural. But you've already
done enough to shame you for two lifetimes. Why not
keep going and see where things go?"
Good point, Tom thought. Tom had little left to lose
in that department.
The pancakes came and the three co-workers ate with
enthusiasm and relatively clear consciences.
Tom was able to concentrate on his work that day, but
just barely. It was as if he had discovered the keys
to a new and magical kingdom that he could visit
anytime he wanted. And be anyone he wanted to be.
Chapter Seven -- Girlish excitement
When the three gender adventurers arrived at the hotel
at 6 p.m. that Tuesday evening, Tom sped to his room
to do his familial duty of calling his wife. The
little woman gave Tom the usual ration about how
difficult the wife had it at home without Tom around
to take out the garbage and open pickle jars. Guilt,
slathered on freely by a professional slatherer. But
in the middle of the conversation, if it could be
deemed that, Tom's wife stopped and said,
suspiciously, "Something's wrong. I don't know what
it is, but? Wait a minute. You sound?happy. That's
so unlike you. Are you doing something you shouldn't?
Who is she? Tell me!"
Well, Tom thought, it was a bit sad that his wife
would see Tom's happiness as a betrayal. And that
thought made him just unhappy enough that he was able
to convince his wife that he was enjoying the work
with Dick and Harry. He was still deeply and
appropriately miserable, just as anyone who deserted
his wife and children for four nights should be. But
he liked the guys on the trip. Plausible denial, the
only weapon a husband has in such situations, seemed
to work and, after a bit more description of how awful
her day had been and how rotten "his kids" were, his
bride released him. To what, for the moment at least,
was a far better, alternative existence.
As agreed, the trio met at the nearly empty hotel bar
at 6:30. All the real activity was below decks.
Though Tom needed no supervision or approval from his
colleagues, he smiled when they agreed with his plan
for the evening. "I'm going to be a guy and be with
Megan tomorrow night," Tom said. "But for tonight,
just to see, I'm going to go to B2 and see what I look
like, girlied-up. Just to see. That's all."
Dick and Harry were delighted at their co-worker's
newly found sense of adventure. They were reasonably
sure that the evening would hold some unforeseen
delights for young Tom.
Harry said, "Well, I'll get girlied up too and show
you around the B1 lounge. What about you, Dick?"
Dick smirked. "I'm in. Three 'girls' on the prowl.
Laurie, Nancy and ??"
Tom didn't know. What should he call himself as a
girl? Then a name flashed into his head. The name of
his first infatuation in the 8th grade -- "Cindy," Tom
blurted.
Cindy it was. But what would it mean to be Cindy?
Even for one night.
The three adventurers downed their drinks and strode
to the "recreation" elevators. Now that Tom had
decided to explore his Cindy side, he was eager to
transform.
Harry offered Tom some excellent advice. "All men
have an X chromosome, so we're all part women -- half
Ginger Rogers and half Fred Astaire -- Gingerfred men.
You can suppress it or you can let it out now and
then. Don't be afraid. Just let yourself be feminine
and submissive. You'll never regret it."
Still, Tom was reluctant to allow his emasculation to
take place.
The City Hotel staff had helped many men like Tom
explore their feminine sides. When Tom, Dick and
Harry entered the "salon" on B2, the staff transformed
Dick and Harry with easy familiarity, then treated Tom
with dignity and compassion. And they moved quickly.
The staff appeared to be female. Very female. Though
Dick and Harry had hinted to Tom that seeing didn't
always mean believing. No embarrassing,
difficult-to-explain changes like plucked eyebrows or
pierced ears. No leg-shaving, though the staff
tut-tutted when Tom refused. No pubic-hair trim
either, though they did shave Tom between his
bottom cheeks and around his anus.
Tom was very excited the whole time those feminine
treasures worked on him. His excitement was "obvious"
and the "girls'" jokes about his woodie didn't help
matters any. When they eased a pair of skimpy, pink
panties over his legs and across his most sensitive
parts, Maggie, the staff member who seemed to be in
charge of things on B2, scolded Lisa and Debbie, who
were sissying Tom up so skillfully.
"Look at that condition you've left poor Miss Cindy
in, ladies. Is that how we treat our hotel patrons?"
Knowing Maggie's scolding was part of the show, Lisa
and Debbie giggled. Then Lisa said, "No, Miss Maggie.
I'll give Miss Cindy some oral relief while Debbie
helps her with her stockings on. But even with dark,
black stockings, she's going to look funny with those
hairy legs, Miss Maggie."
Maggie said, "Miss Cindy knows her own mind about such
things. Perhaps the man she takes to bed tonight will
find that attractive."
Cindy's brain screamed at her over that one. "They
think a man ? They think I want?"
Cindy was about to protest when her senses were
assaulted along two major lines of attack. Cindy felt
warm lips and a soft, wet tongue covering her glans
(or cockhead to the vocabulary-challenged). And she
felt silky, sheer, black stockings being eased over
her right foot, then along her calf, past her knee and
onto her thigh.
Oh, the caress of nylon! The soft whispers that
played along his leg and the lavish licking of his
knob by a very skilled, pantied, perfumed and powdered
tgirl.
Where had those sensations been all his life? Why
weren't there hotels like this in every city? On
every street corner?
Lisa was such an excellent cocksucker -- on her knees
in full cocksucker mode. And Debbie was slipping the
other stocking up Cindy's other leg. Maggie was
saying something about Cindy paying attention to
Lisa's technique so she could replicate it with a man
Cindy would be sure to meet before the evening was
out.
Cindy's mind recoiled at the thought of being on her
knees, in full "girlie," licking and sucking a man's
big cock as he told her how sweet and pretty she was.
But her cock thought it was a spectacular idea. At
the City Hotel, your reservations led you to no
reservations.
Cindy's ears and face were hot as she thought about
releasing her feminine side in the femmiest way
possible. Those thoughts, the soft swish of her
nylons as she rubbed her knees and thighs together,
and Lisa's tonguing of Cindy's peehole made poor Cindy
gasp, lurch and heave her sticky cream into Lisa's
eager mouth and all over Lisa's pretty face.
Spurt after spurt was liberated from her dangling
purse as Lisa gobbled Cindy's knob and swallowed her
creamy nectar.
Through an orgasmic fog, Cindy stammered out a "Thank
you, Lisa," then shockingly to all four tgirls
present, Cindy began to sob.
Lisa was the first to speak. "I don't know why you're
crying, Honey. That was an excellent blowjob. And
you certainly needed it. I never saw so much cum form
one girl. What's the matter?"
Cindy continued her heaving sobs, then said, "I'm a
faggot! Everyone will hate me. My wife will divorce
me and my kids will disown me."
Maggie, who had seen post-orgasmic guilt before said,
"First of all, faggots, as the insensitive call them,
are males who engage in sex. I didn't see any men
here, did you, girls?"
Everyone shook their heads.
"Second," Maggie continued, "what you did with Megan
last night was as boy-girl as it gets, wasn't it,
Cindy?"
Even in her shamed state, Cindy had to agree with
that.
"Third, you're about to go to the B1 lounge, find a
man and let him make cummy love to you all night. But
it's Cindy who'll be taking that big salami in her
pussy, not Tom. It's an exploration of your feminine
side. Get it?"
Cindy got it. She nodded and stopped weeping. Though
she shuddered at the thought of a man pushing his
thing in and out of her. Maggie's logic had its
flaws, but, as they say, it's whatever gets you
through the night.
Maggie nodded. "Good. Now let's get you into this
pretty minidress, touch up your make-up, put this
long, straight, blond wig on you, show you how good
you look, and release you to the world. I'm sure you
know that you don't even have to kiss these guys.
It's up to you. They'll know you're new at this from
your one-inch heels, so they should be gentle. And
they all know that 'no' means 'no.' Anyone who
violates that is banned from the hotel, which is a
death sentence to a tgirl lover in this town."
OK then.
A little touchup, the mandatory scene where the newly
turned-out girl sees herself in the mirror for the
first time and swoons in girlish excitement, and the
games can begin.
Cindy joined Nancy and Laurie and all three ooohed and
aaaahed at each other's girlish attractiveness.
Without Nancy and Laurie's support, Cindy would have
checked out of the City Hotel and slept in a cardboard
box under an overpass. But with one pretty helper on
either side of her, Cindy entered the B1 lounge.
And looked around.
Hmmm.
It looked pretty much like any other bar that catered
to grown-ups. No wide-screen TV or foosball tables.
Cindy took a shy look at the clientele and blushed
when she realized that she was happy to see several
more men than "women."
Laurie, for whom most of her nights in the hotel began
at the lounge, knew the drill. She pulled out a
cigarette and drew an eager clutch of men with
lighters. Which was also the perfect icebreaker for
the men to introduce themselves to Laurie's pretty
companions.
Cindy was very shy, barely lifting her eyes to the men
who were chatting her up. She had to admit, though,
that it was very exciting to be the object of such
lustful attention. Her cock was stiff and drippy.
Tenting her pink panties and even her dress.
The men were too gentlemanly to mention it, but they
liked the fact that Cindy was enjoying the attention.
Cindy eased from her shell and found that she enjoyed
the conversation most with a slim, tall, handsome man
of about 35 years. The others noticed the connection
and backed off, leaving Cindy and her new swain,
Jeremy, to themselves.
Like Cindy, Jeremy Quinn was married. Unlike Cindy,
Jeremy was Fromage-born and Fromage-bred. And unlike
Cindy, Jeremy had no interest in slipping into
panties, stockings and heels. He just adored those
who did.
As a Fromage boy, Jeremy had observed the sissy
culture at close range all his life. Fromage is, of
course, the world headquarters for Panty Boy magazine
and Spermco. Its suburb, Shady Rest, is known to the
world as Panty Town. And the Shady Rest Mall is the
first in America to offer sissy milking stations, a
vital service to a critically important segment of
society.
So Jeremy had been around sissies all his life. And
each encounter stiffened his well-proportioned penis.
Like most sissy admirers, Jeremy had married a genetic
woman and procreated. But even Jeremy's wife realized
that he needed two or three nights "out" each month at
the City Hotel.
Jeremy always felt better when he emptied his
testicles into a sissy's pretty, girlish bottom. And
he was always able to resume his life as a husband and
father with no regrets and with full attention to his
"mainstream" life.
Being paired up with a man, while Laurie and Nancy
were drifting out of the lounge with their carnal
partners for the evening, was making Cindy nervous.
Jeremy did everything he could to set her at ease.
"He's being nice to me because he wants to fuck me,"
Cindy said to herself. But the more she thought about
it, it was the first time anyone had been nice to her
(or Tom) for reasons of proposed fornication. Tom had
always been the supplicant. Women had been the ones
in command of the fucking decisions.
Cindy liked being in command. And she had made her
command decision.
"I've never been with a man, Jeremy," she gulped.
"But I think I'd like to get to know you better."
For the first time, Jeremy was the one who looked
nervous. "Good," Cindy thought. "I've done my part.
I said 'yes,' or at least 'maybe.' The rest is up to
the man. What a nice feeling."
Cindy's nice feelings were only beginning.
She couldn't believe how exciting it was just to walk
with Jeremy to the elevator. She could feel her
dangling balls rubbing against the silky crotch of her
dainty panties. The front of her panties was rubbing
oh-so-sweetly against her exposed, tender knoblet,
putting her more closely "on the verge" with every
step. How did women walk around in that gear all day
without cumming constantly?
Jeremy sensed Cindy's growing excitement and
multiplied it by giving her a soft rub/pat on the
bottom as they entered the elevator. Cindy shuddered
with lust.
When the elevator door closed, Jeremy used the oldest,
yet most effective line known to man. "You're so
beautiful."
And then he kissed her.
A tidal wave of "gay guilt" slammed into Cindy, then
passed into only a bitter memory.
Jeremy laid a proper liplock on his pretty "date's"
glossed lips. And Cindy melted with every molecule of
her feminine side.
Kissing, tonguing.
So good.
Cindy and Jeremy kissed and pawed each other all the
way down the hall to Cindy's room. They somehow
managed to find the key and the fun began in earnest.
Great fun.
The kind of fun you can only have as a girl.
The fun you get from being a true sex object -- your
body a playground for a rampaging man.
Jeremy, who had been in this situation several times
before, knew what to say and do to make a "new girl"
comfortable. Comfortable enough to submit to a nice,
long pussy-fingering. Comfortable enough to suck
Jeremy's cock.
Jeremy knew that this particular "new girl" was going
to suck his cock. Surrendering her masculinity to
Jeremy. Letting Jeremy dominate her in a way a man
adores.
Some men like dominating other men in business or
athletics. But Jeremy knew that the ultimate
dominance was to put another man in panties and set
him on his stockinged knees to suck your cock.
Jeremy laid Cindy on her back on the king-sized bed.
Oh.
She was alone in her room with a man. A man who was
probably thinking about fucking her. Lubing up his
thick cock and pushing it into her. No way Cindy
wanted that. No way. She would just say "no."
Norm Johnson had made it clear to everyone that "no"
meant "no." That was very nice, Cindy thought,
because she could select the things she wanted to
experience and reject the others. Fucking was clearly
out. No man was sticking his cock in her pretty
bottom. Cindy wasn't even sure what she was doing in
bed with a man anyway. She was sort of disoriented.
The permissiveness, the "Hollywood values" of this
darned hotel, was making her consider things that, two
days earlier, she would have rejected immediately and
emphatically. "I won't suck his cock," the part of
Cindy's brain that was, at that moment, still Tom,
thought. "It's icky and humiliating. And no one is
putting his cock in my bottom. I'll let him kiss me a
little. And feel me up. It feels so good to be felt
up when you're wearing stockings and pretty panties.
And it's fun to kiss someone, even a man, when
you're wearing lipstick. But that's all! What is he
doing now? He's stroking my peeny through my panties!
Ohh. That's nice. Why is licking three of his
fingers? Why is he putting his hand into my panties?
Ohhhhh. He shouldn't be putting his fingers in me
'back there.' It's so rude and so..,emasculating to
be handled by a man like that. But it feels
so?..Uhhh. That's so nice the way he rubs those
fingers in me while he's kissing me. Oh?good golly,
Miss Molly. What's he rubbing? Why does it feel so
good? "
Cindy surrendered.
She didn't plan on it. She didn't think it would ever
happen. But she surrendered. To her new-found
femininity. To her girlish excitement. To the
incredible, erotic sensations she felt as Jeremy
kissed her as he massaged her prostate. Was such
pleasure possible? Tom had never felt anything half
as good in his intimacy with his wife. Cindy wanted
more.
Jeremy had swallowed Cindy's tongue. The poor "new
girl's" panties were down below her garter straps and
she was gasping and panting her way to a freight-train
orgasm as Jeremy wiggled his rude digits deep within
Cindy's secret place.
How did he know just the right way to rub a girl like
that? Was this what sex as a "girl" was like?
Cindy liked it.
She especially liked when Jeremy used his other hand
to unbutton Cindy's blouse and expose her right
nipple. No one had ever paid the least bit of
attention to Cindy's nipples.
Jeremy paid attention. The little nub was rock hard
and stiff as a tiny prick.
Jeremy took the pretty point between his teeth and
gave it a small lovebite. Which took Cindy completely
by surprise. And was that "little extra" that pushed
her off Cum Cliff.
Falling.
Squealing.
Pumping hot globs of cum in long arcs from her
straining pricklet.
Balls hurling their sticky treasures into free air.
Spurt after creamy spurt.
Ridding Cindy's body of its mannish toxins.
Filling her with the agony of pleasure.
Changing Cindy (and Tom) in ways she could hardly
imagine.
Cindy's chest heaved.
She was terrified of her feelings.
Vaguely regretful of what she had done.
And certain of only two things.
1) She had just had the best orgasm of her life.
2) She was not sucking Jeremy's cock.
Sucking cock was icky bad.
Something a gay man would do.
Something Tom's wife didn't do for him and Cindy
wasn't about to do for any man. Especially one she
had just met.
Even though he WAS awfully nice.
And he had made Cindy feel good.
Very good.
The best Cindy had ever felt.
Jeremy had put a lot of effort into pleasing Cindy
too.
You don't just put your fingers into ANYONE'S pootie.
That's something you do for someone you really like.
So Jeremy must really like Cindy.
Jeremy had told Cindy how beautiful she was. And he
kissed her so nicely. Jeremy was an excellent spit
swapper.
That was all very nice.
Jeremy deserved something in return.
Cindy didn't want to be rude.
A full ball bag can be very painful. And Cindy was
pretty sure that Jeremy's bag was brimming with sticky
juices.
Maybe Cindy should just take a look at Jeremy's cock.
Rub it a little. Pay Jeremy back for a good turn. No
cocksucking. Just rubbing.
But if Cindy was going to be a girl for Jeremy, there
were proprieties to observe. So she got down on her
knees, then ripped down Jeremy's zipper. Fishing for
his cock.
Cindy found it. And pulled it out. Let it breathe
free air. Admired it. Gasped at its size and girth.
Locked eyes with Jeremy. Licked her glossed lips.
Decided on the best course of action.
Perhaps Cindy would stand up, say goodnight and head
back to her room to watch the latest episode of "NYPD
Blue." Perhaps not.
The part of Tom that was still peeking out from Cindy
was humiliated. On one's knees, in stockings, with
panties down, observing and stroking a man's rampant
cock is not a very manly position. But Cindy was
enjoying herself very much.
Cindy let herself surrender to her feminine side and
kissed the drooling head of Jeremy's substantial cock.
Jeremy groaned. "Oh, Baby," he said.
Cindy glowed with pride. "He called me 'baby,'" she
thought. He thinks I'm pretty and sexy. And I'm
exciting him."
That made Cindy very, very excited. And eager to get
on with a proper cocksucking.
Once she began, it was all very easy. And enjoyable.
A lick here. A caress there. A proper bathing of the
hairy balls with one's tongue. Second nature to us
all, really. And lots of fun.
Instinct directed Cindy's fellatric activities and her
instincts were very good indeed.
Jeremy certainly thought so. "That's perfect, Baby,"
he said. "What a good cocksucker you are. The best."
Cindy glowed with self-satisfaction. "I'm a good
fellatrix," she thought. Clearly, it was a skill in
which one could take great pride. A lost art among
many cultures, but highly respected by men indigenous
to North America, Europe and other moderate climates.
"I'm making someone happy again," Cindy thought.
"Just like last night." That was two more times than
she had made anyone happy since Tom's honeymoon.
Cindy pressed on -- licking, sucking -- even making tiny
lovebites on Jeremy's retracted foreskin. Doing all
the things Tom wished his wife would do for him.
Between complaining about the children, the home and
Tom's meager paycheck.
Well, someone was going to get the accumulated wisdom
of Cindy and Tom. A big, sloppy dose of wisdom, all
over that weeping, pink glans of Jeremy's.
Just to be sure that Jeremy remembered who the
world's-least-experienced-but-nevertheless-best
cocksucker was, Cindy gave Jeremy's swollen balls a
proper tongue bath. The hairs tickled Cindy's tongue
and some got in her teeth, but it was a lot like
eating pussy, which Tom enjoyed, but his wife seemed
to never have interest in anymore.
Oh, well. One eats what's on one's plate. And
Cindy's was stuffed with a big, swollen testicle.
When Jeremy started to make those little grunts that
signal the first twinge, then the second twinge, then
the all-important twinge of no-return, she knew that
she had to make a decision. Would it be a) walk away,
leaving Jeremy's balls blue, b) stroke the erupting
meatstick as she aimed the cum at some distant object,
such as the room's television, c) commit the
horrific, emasculating act of capping the spurting
cock with her lipsticked mouth, swallowing the big
globs of manly juices -- an act of startling
degradation, or d) allow her face to be used as a
receptacle for several thick, hot strands of sticky
cream, allowing herself the ultimate humiliation as a
sex object for a man's disgusting desires.
Figuring that was an excellent set of choices, Cindy
chose both c and d. She took the first two huge
spurts in her wet mouth, gulping the creamy juices
down as quickly as she could. Then she accepted four
more hot blasts all over her pretty face.
It was a fiesta of emasculation, humiliation and
degradation.
And Cindy loved it.
Who wouldn't?
Jeremy loved it too. It was moments like that that
make the life of a sissy admirer worth living. He had
introduced a lovely, feminine person to the joys of
sexual submission to a man.
Had he been a cad, which he was not, Jeremy would have
taken further advantage of Cindy -- flipping her over
and fucking her virginal bottom raw.
He considered cadness or caddity or caddiness, or
whatever it was, but decided that he would return the
lovely favor Cindy had just given him, then leave her
to digest what had happened to her. And what she had
swallowed.
Jeremy knew that it's better for the man "instructing"
the new sissy to keep her highly excited, but not
allowing too many orgasms. Once the sissy has spurted
her gooies, or perhaps the second time she does so,
she is often beset by shame and guilt. Which is the
admirer's signal to go home to his wife and deliver
his next stiffie into the spousal vagina.
But Cindy was ready for pretty much anything when he
laid her on her back, gave her a big, cummy kiss,
entered her "pussy" once again, with two inquiring
fingers, insinuating them in all the best spots.
As Jeremy massaged her prostate, Cindy was frantic
with lust. Jeremy took her pink knoblet between his
lips, kissing it sweetly as he probed the peehole with
his tongue. Pleasure squared!!! Her little popsy was
twitching and she was pretty sure she would cum at any
moment. She was right. But as Jeremy took her places
she had never dreamed existed, Cindy considered
letting Jeremy fuck her. Then she began to worry that
Jeremy would not fuck her, as horrible and degrading
such an act would be ? to a man like Tom. A picture
formed in Cindy's mind of Jeremy on top of her,
pushing his big cock into her, heaving, grunting.
That was all it took. She squealed with a voice that
was completely unfamiliar to her. A voice from her X
chromosome. And she pumped scalding cum out of her
cock into Jeremy's welcoming mouth. It was
phenomenally good!
Then it was phenomenally bad. As the last dribbles of
cum drooled out of Cindy's peehole, she began to feel
remorse for her perversions. She was Tom! A man!
What had just happened and who was this rude,
presumptuous ?person?in bed with her?
Her eyes conveyed first discomfort, then anxiety, then
panic. Jeremy understood. He kissed her quickly on
the lips, began to dress, and said, "It's OK, honey.
You'll be fine in an hour and you'll wish I had
stayed. I'll look you up the next time I'm at the
hotel. You're very sweet and beautiful and I had a
great time. By the loo