The Upsell

The Upsell

I walked in holding the busted cable. The stupid iPod cable had a cut in
it, or something, I didn't know. All I knew is it didn't work anymore.

Adelaide's was the new department store in town. They were having an
opening-week sale and I figured it would be a good chance to replace the
cable and check out the new place. I'd left my roommate Cal on the couch
and went out to get our music situation sorted.

I headed to the electronics section and began poking around, looking for a
new cable. Before too long I felt a tap on my shoulder and turned around.

"Can I help you, sir?" he chirped. I looked up. He was tall, taller than
me at least, a broad man with a wide smile and slicked hair, stuffed into
the store uniform. I paused for a moment, caught in his intense eyes.

"Um, well, I'm just looking for a new cable," I stammered.

"Of course, sir, right this way," he said smiling. He motioned me to
follow him and I did to a rack of cables.

"Oh, thanks." I took one off of the rack and started to turn towards the

"Wait just a moment..."

I turned back to him.

"You know, sir, as long as you're here buying the cable, you may as well
revamp everything and get a new iPod!"

"What? My iPod is fine, though," I said.

"As long as you're upgrading, you may as well go all the way, don't you
think? After all, you're already spending money on that, what's an extra

I raised an eyebrow. He couldn't be serious! That's hundreds of dollars!

As I looked at him though, he took a step closer. I stayed fixated on his
eyes. I somehow couldn't look away, they were just eyes but somehow so
imposing. He put a hand on my arm and squeezed lightly, I felt as though
he was holding my whole body firm.

"Come on, treat yourself," he said. There was something very soothing
about his words.

My eyes followed his. I heard someone say "Sure, why not?" and quickly
noticed it had been me. Before I could take it back I was briskly led to
the display of iPods nearby.

"Now," he said, "I know just the one you need." He reached up to the top
rack, farther than I could have reached myself, and pulled down a new,
shiny, pink iPod.

"Pink? But... that's not what I..."

"Come on," he said. "You're getting a new iPod. You might as well have a
new color! You don't want the same color you already have."

I quickly nodded. Of course, I thought, that makes perfect sense. "Still...
pink isn't really me..."

He affirmed me vigorously, "You know, I completely agree. This doesn't
match what you've got going now at all." He passed the iPod box into my
hands. "As long as you're here, then we may as well get you the kind of
outfit that goes with that brand new iPod."

I was taken aback. "What? But I didn't come in for clothes!"

He laughed. "Of course not. But as long as you've got that new iPod,
you've got to have something to wear it with! You don't want to have an
iPod that doesn't match, of course you don't!"

I tried to argue but could only mumble as he looked at me, intensely,
waiting for a response. My head hurt a little. I could only nod weakly.

Again he grabbed my hand and led me at a fast pace over to the clothing.
He began eagerly rummaging the racks while I stood there lamely.

It took me a moment to notice where we were. "Hold on... we're in the
women's section! What are you doing?"

He thrust some clothes in my arms. "Like you said earlier, you've got to
have something that goes with that iPod! Do you think you're going to find
clothes that go with the pink iPod in the men's section? You just won't.
If you want the iPod you're just going to have to try these on!"

I looked at the iPod still in my hands, slowly adjusting downwards to see
what he'd handed me. I set down the iPod and separated the pieces.

On top was a jean skirt... but it seemed so short! Even for a woman... the
next piece looked fairly normal... a black shirt. But the hole for the head
was so large! It must have a huge... what do you call it... neckline? The last
piece in my hands was a pair of panties. "Pink," he pointed out, "to
match." But not only that, lines of white frill ringed the panties.

I looked at the outfit for a moment, confused. The only piece that matched
the iPod was the panties... and who would even see those? Wait... I wasn't
considering actually wearing this stuff, was I?! By the time I looked up I
was in front of the dressing rooms. I hadn't even remembered walking over
here! The salesman handed me a pair of black sheer pantyhose, which he
must have picked up on the way. He apparently needed both hands free as he
entered the dressing room and turned towards... the sink?

"What kind of dressing room has a sink in it?"

"Oh this is a deluxe establishment, sir, with full spa services. All
outfits are accompanied by a completely free assisted dressing and body

"Body sculpting? But... I don't..."

"You're already getting the outfit. And it's going to look terrible with
all that body hair! That outfit may as well be wasted if you don't go for
the free sculpting, sir."

He came out of the dressing room and stood very close. I looked up at him
towering over me, staring at me, his voice flowing through me. Well... I
didn't want to waste a good deal. I felt a little dizzy as I entered the
dressing room.

The salesman stood in front of me and pulled off my t-shirt, tossing it
over the dressing room door. Next he sat me down and slid off my shoes and
socks. He pulled me back up and undid my shorts and dropped them, with my
briefs to the floor. I said nothing and stepped out of them, blushing. He
picked up everything and tossed it over the door as well.

Pulling out a small bottle, he squeezed a large amount on his hands and
began spreading it over my chest, my back. He knelt down and covered my
legs. He roamed behind me and pushed me over, so my hands were on the
wall. He spread it over my ass, and between the cheeks. As my entire body
began to tingle he pulled out another, smaller bottle and rubbed it over
my balls. He looked up at me and winked. "This one's a little less harsh!"
as he snapped the bottle closed.

The attention to my balls and ass got the attention of my cock, which
began to grow. I bit my lip in embarrassment and blushed deeply as I
looked up at the salesman, who caught a solid glance at my firm five
inches standing before me.

"Very cute, sir!" he nodded. "Now just wait here a moment while the cream
does its work."

The salesman tossed open the door, to the shock of a woman a few yards
away looking at jackets. I gasped and she moved on. The salesman waved for
me not to worry and shut the door. I stood there, my whole body itching
and tingling. It must have been five minutes before he returned, bearing a
pair of four-inch pink heels. "To match!" he repeated, closing the door
behind him.

I had no time to think about the shoes as he wet a rag and began wiping
the cream off of me. He turned me to face the mirror behind me. I watched
as all of my body hair slid off in alarming volume. For some reason, my
cock remained hard. The cloth on my balls and ass didn't help. After
finishing, he washed the rag off and gave me a second going-over, to make
sure all the cream had gone.

I stood for a moment, looking at myself in the mirror. It was amazing how
different I looked with just the removal of some hair. I wasn't sure I
liked it but... it was free, wasn't it? Of course I had to let him.

He handed me the outfit and stood in a corner as I dressed. I slipped the
frilly panties up my legs, appreciating the feel of the soft fabric on my
somewhat tender skin. Looking in the mirror, I blushed. Why was I wearing
this? I'm a man but... then I remembered it was to go with the iPod. Of
course, of course. My still-hard cock was tamed by the panties a bit, and
strained against the fabric. At least it wasn't still poking out free.

I stepped into the jean skirt and fastened it around my waist. I sulked a
moment in the mirror, noticing that the bottom of my panties were still a
little visible under the short skirt. "I don't think..." I started, but was
interrupted as the salesman handed me the top. I forgot what I was going
to say and dropped it on my head. The low neckline looked a little silly,
without any tits to support it.

Thinking over the aesthetics of the outfit, I unpackaged the pantyhose and
rolled it on my feet and legs, having a little bit of difficulty but
figuring it out.

The salesman held my arms and sat me down, kneeling once again to slip the
heels on my feet. He stood me up, holding my hand for the first few wobbly
steps. I quickly figured out my gait in these new weird shoes.

"These clothes wouldn't have gone with your old shoes. It wouldn't make
any sense to get them without these heels!" nodded the salesman. I nodded
in agreement. The skirt would look ridiculous with my old sneakers.

He opened the door and I stepped out.

"Hey... where did my old clothes go?"

"You know, I just remembered. Those shoes can't be bought on their own.
They're a package deal... only five dollars above the normal price, but it
comes with a makeover package!"

I shook my head... wasn't I asking a question? I couldn't remember as he
kept talking.

"But, makeup? I..."

"It comes with it. You might as well."

Before I said anything, he started leading me in my new outfit and shoes
over to the makeup counter.

"Carol, darling, as you can tell this man here has a new themed outfit.
See the pink?" he said, briefly lifting up the skirt to reveal my lace
panties to her. "Something to go with that."

I noticed a sign next to Carol stating that makeovers were typically $60.
And here I was getting one for only five dollars extra... I supposed it only
made sense to go through with it.

I sat in the chair, leaning back. Carol smiled over me and grabbed her
tools. A few minutes of poking, prodding, and brushing, she sat me up in
the chair and held a mirror before me. I gasped. Big red lips, deep
strains of shadow running up my face, shaped and smoothed eyebrows, and a
dark eye shadow.

The salesman nodded at me, smiling. He pulled me out of the chair and took
me to a full length mirror so I could have a full view of the outfit. As I
looked, he tsked and sighed.

"You know it's a shame," he said.


"I've got to say, in that makeup you look downright feminine. But as soon
as you go home, you're not going to know how to put it on again."

"I guess that's right..."

"It would sure be a waste to not take advantage of being so feminine while
you have a chance. That free makeover would just be for nothing."

"Well I wouldn't want that..." I was catching up. Wait a minute... feminine?
How the heck did I end up completely made up like a...

"Let's just make sure to take advantage of that makeup while you have it."
the salesman grabbed me once again and led me to a door marked "employee
lounge," closing the door behind him.

My eyes went wide as he unzipped his pants and reached inside, pulling out
his cock... it must have been eight inches, and thick. I gasped and looked
up at him. "But... but I..."

"That lipstick is non-smear, sir. I just want you to get the most out of
your purchase, this is really an essential add-on. And a professional
courtesy to our guests here at Adelaide's."

I touched a finger to my lips. None of the lipstick came off. I paused,
but he stared directly at me. I looked up at him again, those dark eyes
holding my gaze until I began to sway lightly back and forth. My eyes
dropped to his cock.

"Ma'am, I really wouldn't want you to waste your purchase. You already
have the makeup on, you may as well."

Did he call me... it didn't matter, a mistake is fine as long as he's
working so hard to get me such a great deal! I smiled and dropped to my
knees. I leaned forward and parted my lips, taking the head of his cock

I licked at the head of his cock before taking it in further. His cock
throbbed in my mouth as it went in further and further. As it hit the back
of my throat I began to cough but he warmly informed me that as long as
his cock was in there, it wasn't much more to just let it go a bit
further. His words flowed through me warmly and my throat relaxed.

Soon he was holding my head and thrusting his cock down my throat with
regular rhythm. I caught myself moaning. He stood tall before me,
completely dressed except for his cock buried inside me.

He thrust deep inside one last time, holding my head, and broke his
demeanor for only a moment to gasp as he began shooting ropes of cum down
my throat. I swallowed it all, a few drops falling on my tongue as he
pulled his cock from me. I rolled it around on my tongue, enjoying the

I stayed on my knees in front of him as he stood there, his cock
deflating. When it allowed, he tucked the cock back inside his pants and
zipped up. I noticed happily that there was no lipstick on his cock. A
purchase well justified!

He helped me to my feet, immediately reaching a hand down under my skirt
and feeling my panties. My rock hard cock was straining against the
panties again, a small wet spot forming on them.

"Ma'am, I'm glad you seem to be enjoying this."

"I have to get a good value, don't I?"

"Yes, of course. And this is exactly the kind of value a sissy slut like
yourself is looking for."

I jolted back a moment. "Wait, what? What did you call me?"

"Well ma'am, you've just had sex with man whose name you don't know while
dressed in women's clothing and makeup. I can see that you've selected to
be a sissy slut. That's the term, ma'am. It's very popular, an excellent

I looked down at myself, and over at him. No way... why had I... how was I... I
blushed deeply

"No... no way... that's not who I am!"

"Ma'am I would like to point something out. Just to optimize your
experience here at Adelaide's..."

His soothing voice rocked me. I looked in his eyes and forgot again what
my objections were.

"Once men such as yourself have chosen to be sissy sluts, we do offer an
additional program which can get you cash back on your purchase."

"C... cash back?"

"Of course, ma'am. You already enjoy being fucked by strange men. You may
as well get paid for it as long as that's what you're doing."

Prostitution? But... well if I was going to be doing this anyway it only
made sense. But... wait! I wasn't planning to do this ever again! But, I'd
clearly already done it. My head began to hurt again. I put my fingers to
my forehead.

"Ma'am, I've just got to say it. When a sissy slut is fucked for free,
she's just missing out on opportunities for cash!"

I nodded, slowly. Of course, that would be silly. What if I'd gotten paid
for blowing him right now? I'd already missed out on the savings. I wasn't
about to let myself get taken advantage of again!

He smiled. "Excellent, ma'am. I'll get you started. One moment."

He led me to a back door out of the employee lounge. It opened into an
alleyway, where a van was waiting.

"Ma'am, inside there are your first two cash-back opportunities," he said.
I nodded, happily.

He opened the back doors of the van. Inside were two large men, both with
beer bellies and built upper bodies, completely nude, stroking their fat

I climbed into the van and the salesman shut the door behind me.

I paused, unsure what to do. I realized I didn't have much experience with
this... maybe I wasn't a sissy slut after all? But quickly I noticed my
eyes locked on their fat cocks and leering grins and I nearly began to

They didn't pause to introduce themselves. The bigger of the two
approached me and roughly groped my crotch. I shuddered, little jolts of
pleasure running through me. Suddenly the whole thing felt so right. I
could hear the salesman's words in my mind. This was exactly what I had
chosen, what made sense to do! After all, if a sissy slut is going to be
fucked she may as well get paid!

I moaned as the larger man rubbed my cock through the panties. "We have
ourselves a real good sissy slut here" he mumbled to his friend.

The smaller one got up and came behind me, pushing my skirt up around my
waist. He reared a hand back and gave my ass a good smack. I gasped, but
before I could make much of a noise the larger one's tongue was in my
mouth, probing it deep.

The smaller one wasted no time pulling the back of my panties down and
positioning me on my hands and knees. I could feel his precum dripping on
my ass as my cock quivered and jolted in my panties. I kissed the larger
one deeply, feeling stubble rubbing against my face.

I gasped in his mouth as I felt cool lube being squeezed from a bottle
over my ass. The man behind me rubbed his cock in the pool of lube,
collecting it.

The larger one backed off, wanting a good look as the enormous cock began
sinking into my ass. I was immediately impressed with my ability to take
it so well. I gasped and let out a feminine squeal as the cock slowly
began stretching me open. It felt like a log spreading me wide open,
coating my insides with lube and filling every inch of the inside of me.

The cock put pressure on my prostate, making me bite my lip in utter
ecstasy, hardly able to keep still, knowing that I needed to for the sake
of the strong man behind me.

As I lost focus, unable to think of anything but the overwhelming pleasure
spreading from my insides, I looked down at myself, at my new sissy,
slutty clothes. Of course this felt good. Of course this was right. What
else could someone who looked like this be? Why else would I have gotten
this outfit if I wasn't planning for this to happen?

My thoughts were cut short as the large man's impressive cock pushed at my
lips. I opened wide, moaning just at the taste of cock.

I moaned around the cock in my mouth as the one in my ass pushed all the
way home. He gave me a moment to adjust, my insides feeling like they were
shifting around to accommodate the new neighbor. The cock in my mouth
drove forward as well, down my throat.

In exact synchronization, the two pulled almost all the way out, leaving a
longing feeling in both of my holes. Then, they drove home again. I felt
nearly crushed between the weight of the two. They started fucking in
earnest, my whimpers beneath them turning to moans, turning to gurgles
around the cock in my mouth as my own cock began shooting in my panties,
totally untouched except for the soft rubbing of the panties against it.

I heard sucking sounds as the two men at each end of me began kissing each
other while thrusting into me. They parted, and started fucking faster and
harder, laughing as they pointed out my clothes, clearly amused at the
not-quite-man beneath them.

My cock had regrown after shooting, bobbing beneath me as my body was
rocked by the large men. Their weight, their scent, and their cocks were
driving me wild.

With deep growls the two men thrust forward one last time. "FUCK!" They
both began shooting ropes of cum inside me. I swallowed as quickly as I
could but still a few drops began leaking out onto my no-smear lipstick. I
felt the warm flow of cum beginning to fill my ass as the smaller of the
two shot his load. The overload of sensation had me coming a second time,
still without touching my cock once. I nearly melted. If two cocks hadn't
been holding me up I'd have probably collapsed.

The men pulled out, grinning. I lay on the floor of the van, panting,
feeling my throat and ass closing with no cock to keep them open.

I hadn't lain there too long before the smaller one got up and knocked on
the inside of the van door. The salesman, grinning wide as ever, opened
up. I dazedly watched the proceedings as the two men who had just fucked
me senseless handed over what looked like a lot of money to the salesman.
"Glad for your business, boys!" he added. He pulled me to my feet and I
tumbled out the door. The salesman shut it behind me and the men drove

"This should just about cover your purchases. It seems like you've been
enjoying your choices, ma'am?" he asked.

"I... oh god it was..." I felt cum running down my ass and realized that I
was still half-nude in the alleyway. I pulled my panties up, feeling cum
from the man and my own both rubbing against me in my panties, wobbling a
bit in my high heels.

I felt a deep sense of shame coming over me. I had just become a
prostitute! What was I doing? I looked uneasily at the salesman. He
noticed my look and frowned.

"Look, ma'am, I can tell exactly what you're thinking."

"You can?"

"That's right. You're thinking... well, this is all well and good, but if
only I didn't have to deal with doing everything one transaction at a
time! How will you ever get the best deal if you don't have something

"That's... that's what I'm thinking?"

"Oh good, I'm glad we're on the same page. Well I have some good news for
you. We have an upgrade package!"

"An upgrade package?"

"You're already a prostitute. But this whole process is inefficient.
Wouldn't it be better if you could just get paid once and never have to
deal with all that again? Only one transaction and you're set for life."

The cum inside me, the cum on me, felt warm. A soreness in my ass called
to me. I stroked absently at the feminine clothes I was wearing. I felt
uneasy, but yet one more look at those insistent dark eyes staring at me
and I could say nothing but "Yes... yes that only makes sense... as long
as I'm going to be a prostitute I should definitely be efficient..."

He nodded sagely, leading me out to the street. He unlocked a small red
sedan parked on the street and motioned me inside. I sat down, cum
spreading across my ass. He got in the driver's seat and turned it on. My
exhaustion from the incredible fucking session combined with the rumbling
of the car sent me straight to sl**p.

When I woke up, the salesman was jostling me awake and pulling me out of
the car. We were at the airport. I woke up, stumbling after him still
confused. He walked quickly.

We went through security quickly, the salesman showing the guards
everything they wanted to see. Inside we arrived at a part of the airport
I'd never been to. Small planes were outside the window. Private planes.
The salesman tapped me on the shoulder, distracting me from the sight of
the planes.

There was a toned, bearded man standing next to him, looking me up and
down, and then giving a thumbs up to the salesman. The bearded man pulled
a large roll of cash out of his pocket and handed it to the salesman.

The salesman put his hand on my shoulder and talked with his warm voice at
me again, "I'm glad you've chosen the truly elite package, ma'am. I'd like
to introduce you to this man. His name is Mr. Taunton. But of course you
won't be calling him that. He's made a one-time transaction. Save you all
those hassles of being a prostitute like you would have been otherwise. He
is your owner, for now at least, until he sells you on to a good home."

My eyes opened wide and my jaw dropped. I stammered, "Wh... what? But

Mr. Taunton shushed me. "Don't object, slut, it's unbecoming. No reason to
be rude."

I stopped. No reason to be rude, of course.

The salesman spoke again. "Now, it's been very nice serving you today,
Ms..." he looked to Mr. Taunton. "Cunt." Taunton nodded. "Ms. Cunt," the
salesman finished.

"But my name is..."

The salesman cut me off. "That never mattered. This is your new name.
Doesn't that sound like a fitting name for you?"

My mind swirled and I couldn't help but nod.

The salesman smiled and pulled up his pants, looking me up and down,
nodding, proud of a job well done. He turned around and walked away.

Mr. Taunton pulled from his pocket a small collar. I looked at him blankly
as he fastened it around my neck. He showed me a small metal pendant,
engraved loudly with my new name, and fastened it to the collar. My sense
of dread was broken by the sight of a sizeable cock pressing hard against
his jeans. He grinned and patted me on the head. "A good sissy slut is
never down for long. Isn't that right, Ms. Cunt?"

I felt the collar sitting loosely around my neck. I felt like I could
smell, and nearly taste, the cock imprisoned not far in front of me. I
felt an aching in my ass, longing to be filled. I licked my lips. "Yes Mr.
Taunton, that's right." He wagged a finger at me. "That's master, Ms.

I blushed and bowed my head. "That's right, master."

He smiled. "I hope you're ready. When we find you that new owner you'll be
quite busy. Whatever he needs - of course he'll have you fucking whenever
and whoever he wants. Cleaning the house, serving drinks, maybe he'll even
have you making him some money. And of course we offer options... he may
want some tits on you."

I didn't know what to say. It somehow felt right. I stayed silent. I could
tell Master liked that.

Mr. Taunton pointed me towards the gate. I looked up at the destination
sign and realized I didn't recognize the name listed there. Some country
I'd never heard of. He led me on board and I remembered my identification,
wallet, everything that proved who I was, left behind in my old clothes.

He sat me down and turned to me "This plane ride is important for you. All
your potential buyers will be here, and by the time we land I want you to
have a new master to take you off my hands! So impress them! You'll have
to be better than the other sluts."

"Other sluts?"

"They're coming" he nodded, and left without another nod. It was hours
before he returned. In tow were ten large, smiling men, stripping their
clothes and laughing with each other as they entered the plane, nearly
drooling at the sight of me. Behind them came three more sissy sluts just
like me. Before I could take it all in I'd been grabbed and f***ed to the
floor. I moaned just in anticipation as my panties were ripped off
entirely and an enormous cock was thrust inside me. The man on top of me
grunted and I could hear activity in the rest of the plane kicking off as
the plane took off.

I wouldn't be without a cock for hours. I couldn't keep my eyes focused.
With the plane still high in the air, my clothes drenched from cum, I
squealed happily as a man grabbed me for his third... fourth... fifth go?
He laid me next to another one of the girls, luckily with the largest cock
in the room straight up her ass.

I looked down at us, our cocks bouncing straight up, obscenely pushing out
our cum-soaked skirts. I took a moment to tear my eyes away and look up at
who was next to me.

"C... Cal?" My roommate?

"Don't call me that! My new name is FuckMe!"

I grinned wide. What a fitting name for a sissy slut like her. I spoke in
caught breaths between thrusts of huge cock in my ass. "But how...?"

"You didn't come back for so long... I went to see what was up!"

He moaned as her little cock shot ropes of cum in the air and on his
exposed belly.

"You know," he panted, "I met the nicest salesman there..."

100% (10/0)
Categories: BDSMFetishShemales
Posted by klammer
8 months ago    Views: 1,259
Comments (3)
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8 months ago
Wonderful! I hope we'll get to read what happened next
8 months ago
uhh what is the address to that store?
8 months ago
soldbtobe a slut what a life