Maid to Order — Initiation (Part 2)

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Maid to Order — Initiation (Part 2)
Maid to Order — Initiation (Part 2)

When she stepped through the door I thought “I’ve been had, this is
really a housekeeper!” She was wearing the same uniform I had seen other
housekeeping staff wearing–a short-sleeved pink polyester button-front
utility uniform with a crisp white straight-waist apron.

She didn’t seem startled to see me, however, and stepped into the room,
letting the door close behind her. When I started to speak she held up
one finger as she turned to lock and bar the door. She turned back to me
and came a few steps closer. She paused; her right hip thrust out with
her hand on it and appraised the situation. She had dark hair and dark
eyes and her skin was smooth with a dark complexion.

“Well, at least I see you can read and follow simple instructions,” she
said. Her voice was rich, with a light Latin American accent. Again, I
attempted to speak, but silenced myself when she held up her finger
again. She reached over and picked up the panties from last night still
on the end of the bed where I had dropped them.

“When I picked these up this morning I thought, oh, here’s another
businessman who likes to have a little fun while he’s out of town. I
find wadded up dirty panties all the time, but something was different
about these panties.” She held them up as she moved a few steps closer.
“All of the dried crusty spots on these are in the front, not in the
crotch.” She turned them around. “And there’s a curious stain pattern
here in the center of the waistband that smells like,” she pretended to
sniff, “anal discharge and lubricant.” She dropped the panties.

She reached behind her and untied her apron, tossing it aside. It was
then that I noticed her shoes were not the usual shoes one sees on a
hotel maid. They were black leather lace-up oxford pumps with what
looked to be a 5-inch heel. She started unbuttoning her uniform as she
continued. I was transfixed and could only listen.

“All of this was confirmed, of course, when I opened your drawers. After
all, what businessman travels with that much lingerie unless he’s wearing
it himself? That really only left one question unanswered. Were you
alone last night or was there someone else here? A quick look through
your suitcase revealed most of my answer, though it did leave some room
for doubt.”

She had finished unbuttoning her frock and I caught just a glimpse of
what was underneath–some form of sexy lingerie. She held it so it
didn’t come open.

“What is your name?”

“Uh, I, uh my name? Uh,” I started my nearly unintelligible reply.

“I know your real identity and particulars already,” she snapped, “I want
to know YOUR name.” She gestured at me.

“Stacey,” I said.

“Stacey,” she repeated. “Pretty name. Tell me Stacey, I see a ring on
your finger. Does your wife know about all this?”


“Interesting, though not unexpected. Does she ever, ummmm, participate?”

“Participate?” I asked. “What do you mean?”

She opened and removed her frock with a flourish, tossing it aside as
well. Underneath it she wore a sexy French maid outfit, but with a
delicious twist. Her ample tits were barely contained by the halter-
style bra that tied in the front. The bra cups were split and her dark
nipples were nearly visible. The “skirt”, if it could even be called
that, was actually two separate pieces–one in the front and one in the
back–in black satin with a small white lace-trimmed “apron” across the
front. The two pieces were attached, however, to a strap-on harness that
was fastened around her waist and around her legs where they met her

Sticking out from her harness was an 8-inch black dildo. It was a
realistic shaft with bulging veins and a large well-formed head (though
it didn’t have balls). It looked obscene and sexy all at the same time.
She wore black stay-up stockings to complete her look. She looked ready
for business.

“Does she “participate,” she emphasized the word by gripping her black
dildo and shaking it in my direction, “with your dressing fetish and anal

“No.” She walked around me now, looking at me from behind.

“Have you ever been fucked before? In the ass?”


“Not with a dildo on your beach ball, I mean have you ever really been
fucked in the ass by another person?”


“Have YOU ever fucked somebody in the ass?”

“Yes, but only my wife. I’m a married man.”

“Have you ever touched someone else’s cock?”


“Have you ever sucked a cock?”

“No, well yes, sort of.”

“Explain.” She walked around back in front of me.

“When I was young, maybe nine or ten. It was just us neighborhood boys
fooling around with Truth or Dare; you know, that kind of thing.”

“Go on.”

“Well there wasn’t much to it, just taking my turn putting everyone’s
dick in my mouth like we all did as part of the dare.”

“So you had your dick in their mouths, too?”


“Did you come in anyone’s mouth?”

“Do you mind if I ask a few questions here?” I was starting to get

“I have to know these things, Stacey, if this is going to work. I
promise you won’t be left with any unanswered questions. Did you come in
anyone’s mouth?”


“Did any of them come in your mouth?”

“I think so. I thought he was peeing at the time so it grossed me out,
but now that I think about it, it was probably come.”

“Just the one time?”

“Well, actually, it happened to me a lot whenever we played the Dare
game, though not always the same guy.”

“Bad odds, wouldn’t you say? You said, ‘whenever we played,’ which I
take to mean you did it more than once. How often did you play this Dare

“Well, there for awhile we did it almost every time we had a sleepover.”

“How many times?”

“Maybe a dozen over a few years’ time.”

“When did you start wearing panties?” She walked back around behind me.

“In the Air Force after . . . wait a minute. I seem to remember doing it
a couple of times when we played the Dare game now that you’ve brought
the memories back up. It was only a couple of times while we were at
Billy Swanson’s house. His Mom had the sexiest panties.”

“So you all wore them?”

“I think so, at first. Then it was just whoever lost and had to put
everyone’s dick in their mouth. Eventually it seemed like it was usually
just me. güvenilir canlı bahis siteleri Wow, I hadn’t thought about this in years.”

“So you used to put on women’s panties and take your friends’ dicks in
your mouth, even letting them come in your mouth? I think I’ve heard
enough. We can proceed.”

“Proceed?” I asked. “Proceed with what, exactly?”

“You have passed the first two tests. Now we can get on with the third.”

She reached down and picked up my bottle of Astroglide. I heard the snap
of the lid and the *splurp* as she squeezed some into her hand, followed
by the unmistakable sound of her lubing up the shaft of her dildo.

“Wait a minute,” I said. “I’m a married man! I can’t do this! I’ve
never cheated on my wife!”

“You’ve already been cheating on your wife in your mind with all your
crossdressing fantasies. Besides, you won’t be doing any cheating–
you’ll be getting used as a fuck slut. Your cock is going to stay safely
tucked in your panties. My only interest in you is the holes you have to
use. You won’t be sticking your dick into anything.”

“But,” I started to protest. I felt her hand on the handle of the dildo
in my ass. My brain was screaming “NO” while at the same time my
hardening cock in my panties was screaming an overwhelming “YES.”

She tugged on the handle and pulled the dildo from my ass. I felt the
cool head of her dildo pressed against my hole, which had not been opened
as wide as her dildo by the Anal Twist.

“My name is Marisa,” she said as her hands gripped my hips. “I am not
your mistress, so you will never address me as such.” She pushed and the
head of her black “cock” stretched my asshole and popped inside me. “I
am your pimp, and I will soon begin selling your holes to my very select
clientele.” She pushed and my ass swallowed half of her shaft. “I not
only know who you are, I will also never hesitate to sell you out if you
cross me. Do you understand?”

I nodded, dumbstruck. What the hell was happening? I was being turned
into a prostitute?

“Say it,” she said, “out loud.”

“Yes, I understand,” I said meekly, my mind still reeling at this
unexpected turn of events.

“Then push back, and show me how eager you are to accept your new role.
I want you to take the rest of my shaft–all of it!” I did as she asked,
pushing back against her, feeling the remainder of her 8-inch cock
filling my ass.

“Good girl, Stacey,” she purred. “Now let’s see how well you handle
being fucked.”

Marisa gripped my hips, pulled most of the way out of my ass, and then
rammed her dildo back inside me. She started fucking me hard and fast,
really drilling me. As she drove her cock in and out of me the sound of
her thighs slapping against my ass echoed through the room. I felt her
hands shift, and now she was gripping the rear garters of my garter belt.
She pulled me back as she lunged forward, continuing her relentless

As she tugged on my garters it pulled my garter belt tighter against my
panties and squeezed my cock. That, coupled with my being pushed against
the ottoman kept me close to the edge of orgasm. I didn’t know if she
had any attachment as part of her strap-on system that was providing her
pleasure as she fucked me, but after the first 5 minutes she started
punctuating each of her thrusts with a sexy accented “Oi.” After what
seemed like fifteen minutes of hard fucking she finally lunged forward
one final time and cried out loudly as she came, a stream of Spanish
gibbering from her mouth.

“That was pretty good, Stacey,” she said, “but you need to participate
more. Nobody likes fucking a cold fish; my clients could get that from a
sex doll. Push back against the penetration, just like you do with your
beach ball.”

She started fucking me again, this time with slow, steady strokes. She
had released my garters and now had her right hand on her hip as the
other grasped the back of my garter belt and the “t-junction” of my thong
panties and held them together in a fist.

“C’mon,” she urged me. “I know you can do this.” I started meeting her
thrusts, pushing back against her as she continued her pace. “That’s
better. Good girl. I know you have a million more questions, so let me
tell you more about how this works.” It was somewhat surreal that she
continued almost casually fucking my ass as she explained just as
casually how our future arrangement for pimping me out was going to work.

“First–and this is very important–you will be part of my unique stable
of “girls” and your well-being is one of my top priorities. My clientele
is very exclusive–judges, lawyers, politicians, business executives–all
with one thing in common. They all like sex a little more perverted than
mainstream America. In order to stay on my client list, they must submit
to regular STD and AIDS testing. I do this because most of them refuse
to wear condoms and I will not have any of them infecting my girls.”

“Some of these men like to dress as well, and like to have sex with other
“girls” while they are dressed. Some of them are otherwise normal but
like their sex with a little twist. Some of them have certain fantasies
and like their girls in specific costumes.”

“You only work for me when you are staying here in this hotel. You will
notify me as soon as possible of any upcoming stays and your itinerary.
All of your scheduled meetings will take place in your room. I set up
all of your meetings. I set up any specific requirements for the
meeting–like specific lingerie, toys or costume requests. I collect all
the money in advance and you get your percentage plus you get to keep all
the lingerie and other items.

“I will e-mail you your appointments, along with the details, and when
you get back to your room at the end of your business day, your money and
any specific outfits will be waiting for you on your bed.” She stopped
fucking me and I turned my head to look at her.

“Do you understand?” she asked.

“Yes,” I said.

“Good. You’ve passed the third test. I’ve fucked you both hard and fast
as well as slow and steady for the past 25 minutes; so I know you can
handle a good ass-fucking. Now we have just one more test, this one in
two parts.” She picked up my Anal Twist toy and applied a fresh coating
of lube. güvenilir illegal bahis siteleri She pulled her dildo out of my ass and then suddenly rammed its
entire length back in for a few more quick, hard strokes.

“You have such a nice ass,” she said, “I really hate to stop fucking it.”
She pulled out, standing up this time, and replaced the void in my ass
with my own toy. She walked around in front of me and straddled the
ottoman, leaving her dildo dangling in my face. I could plainly see that
it was covered in a gooey mixture of shit and lube. “Suck my cock,

I had only dabbled in ass-to-mouth before. Now it looked like I was in
for a full taste of it. As I opened my mouth she grabbed the back of my
head and slid her black cock into my mouth. I took the first 4 inches of
it–even with the wide head–fairly easily. She thrust it between my
lips a few times and then pulled it out.

“Lick it off,” she told me. As disgusted as I was I did what she asked,
sticking out my tongue and licking the slime from it. I slid my lips and
mouth up and down the shaft, cleaning it off. “Aren’t you a good little
cocksucker? Have you done ass-to-mouth before?”

“Mmmm-hmmm,” I mumbled around the dildo in my mouth.

“Just your dildos, though, right?”

“Yes,” I said in the brief interval between her pulling the dildo from my
lips and sticking it back into my mouth.

“Well, let’s see how you do with the length.” She grabbed the back of my
head and pulled my mouth onto her “cock.” I was taken by surprise, and
gagged at first contact with the back of my throat. “C’mon, Stacey, you
can do better than that, honey. You’ll HAVE to do better than that.” I
was prepared for her next thrust and tried to relax and open my throat.

This time I was successful, and her dildo slipped into my throat. She
pulled my head and thrust forward at the same time, giving me the full
length. As her harness mashed against my face, I could smell the strong
unmistakable scent of her wet pussy.

She pulled out and stepped away from the ottoman, moving backwards.
“Come and kneel here, Stacey,” she said. “I need to see how well you
perform on your knees.”

I slipped sideways off the ottoman, reaching around behind me to hold the
Anal Twist toy inside me as I crawled over to where Marisa stood with her
hands on her hips. I knelt, leaving my butt low enough to the ground for
the handle of the toy to help keep it inside me.

Without being asked I immediately opened my mouth and resumed sucking.
She thrust it back down my throat and started face-fucking me. The smell
of her pussy was driving me crazy and I could feel my cock get even
harder each time I caught a whiff of her sexy aroma. I reached around
her hips and grasped her firm ass in my hands, guiding her efforts now to
fuck my throat. She didn’t resist.

“That’s a good girl, Stacey,” she cooed. “Show me how much you want it.
Pull me in while you open your throat for my cock.” She stopped
thrusting and let me pull her toward me as I bobbed my head, fucking my
own mouth. I took her dildo out of my mouth and licked the shaft,
slurping up and down on it. Each time I neared the base, the smell of
her pussy drove me crazy. I finally couldn’t resist and the next time my
licking reached the bottom of the shaft I kept going.

My tongue travelled past the dildo base and slipped between the nylon web
straps where they separated to go around her thighs. Her pussy was
almost covered, but I found the very edge of it and licked it and her
perineum–basically everything I could reach. Marisa squealed a little,
but didn’t pull away.

“Well, that was a pleasant surprise,” she said. She pulled up on her
dildo and exposed more of her pussy, which I eagerly licked, trying to
fit as much of my tongue inside as this awkward angle would allow. She
grabbed the back of my head and ground her pussy against my face for a
few minutes. “It’s good to know that you have the skill and desire to
please some of my female clients, too.”

“I wish I had time for this, Stacey,” she said with a tone of finality,
“but we have one more very important test to go.” She pulled away from
me, walked over to the door that connected to the adjoining room, turned
the deadbolt and knocked on the door. I heard the door on the other side
open, and then the door to my room was being pushed open.

I had not expected this and my heart started pounding again. My mind
raced, wondering who was going to walk through that door. Would it be a
black man with a big black cock? Would it be another crossdresser?
Would it be one of her special clients? I didn’t have to wait long for
my answer.

My first glimpse was of a black patent leather high-heeled pump at the
end of a sexy leg in stockings or hose. I saw a flash of pink as the
other leg came through, and then standing before me was a gorgeous

She was wearing a gartered babydoll with a hot pink satin front with
black straps and garters. From what I could see, the sides were sheer
Lycra in the same shade of pink. It had a black bow between the
underwire bra cups and a sexy sheer lace ruffle around the hem. The top
of the garters was trimmed with similar black bows and held up her
stockings. She had long blonde hair and her eyes were made up with
earthy tones. Her lips were a silky pink shade and she was wearing a
pink Sorrelli necklace. Her body was well-toned as well as tanned.

It was immediately apparent that she wasn’t wearing any panties, because
her cock hung between her legs, its head just peeking out below the
ruffled hem.

“This is Kayla,” Marisa said. “When I first met her she was a
maintenance worker here at the hotel. I caught her in a guest room
trying on lingerie–another man’s lingerie, kind of like you. I made her
beat off in front of me that first time. It turns out that she has a
very special skill, a skill I need from time to time. We call this last
test the ‘volume’ test.”

“You see, Kayla can produce a huge amount of cum, much more so than even
guys who hold it for awhile. We have a special arrangement–she saves
her cum for a whole month at a time so that I can use her for this last
test for new girls. If I don’t have any new girls for her to test, then
she gets her pick of my girls güvenilir bahis şirketleri at the end of the month.”

“Kayla, this is Stacey.” Kayla walked over to where I was kneeling and
stood in front of me, her hands on her hips. I noticed that her
fingernails were painted with a matching hot pink polish. Her cock was
getting harder and now not only was longer than the hem of her babydoll,
but was also starting to rise.

“Stacey, I know you can suck cock, and you do pretty well with length,
but I need to make sure you know how to swallow cum as well. The average
human stomach holds just under a liter–a little smaller than the largest
cup at Starbucks. She doesn’t cum that much in one go, but she certainly
makes an impressive amount–especially when she saves it up for a month
or so.”

Without waiting for further instructions I walked on my knees the
remaining distance between us until Kayla’s cock was right in front of my
face. I reached up and grasped her cock in my right hand–my first time
touching another cock as an adult. It was warm and spongy and jumped
when I touched it, and I felt it grow harder still. I opened my mouth,
took her cock inside, and closed my lips around it. That first touch of
a warm cock against my lips and in my mouth was electric!

I felt my own cock stirring in my panties and my ass twitching around the
dildo still deep inside me. I suckled at the cock, feeling it grow to
full hardness in my mouth. It wasn’t as long as my favorite dildo, but
it was a bit thicker. I alternated between licking her shaft and sucking
the head and the first few inches of her cock as my hand stroked her.
After a few minutes of this I knew I had to have more–I was loving it!

I slathered my tongue up and down her cock, making sure it was well
lubricated. Then I took a deep breath, grasped the cheeks of her ass
(which were covered in smooth, slippery Lycra) and pulled her into my
waiting throat. I took her entire length on the first try. It was such
a sexy feeling to have the ruffled trim of her hem tickling my nose as
her balls mashed against my chin. I didn’t have much time to enjoy my
achievement, however, as Kayla placed both hands on my head and started
fucking my mouth.

It was obvious she had been waiting for this moment for a long time. She
thrust in and out of my mouth, barely giving me enough time to catch a
quick breath in between. I could tell by her pace that she wasn’t
interested in a nice slow blowjob. No, she wanted to fuck my face and
dump a big load of cum in my mouth. I wasn’t the only one who noticed.

“My, my, Kayla,” Marisa said, “somebody seems to be in a big hurry

“I can’t believe this is a new girl,” Kayla replied. She didn’t try to
feminize her voice. “She already sucks dick like a pro. She’s better
than some of the girls who have been working for you for years now.”

“Well, don’t be too hard on her. It’s still her first time sucking a
real cock.”

“You’ve got to be shitting me,” Kayla said. Carrying on a conversation
hadn’t slowed her down any–she continued to pound her cock down my

“Nope, this is one new recruit with a lot of natural talent.”

“Well, her mouth feels so good, I’m not going to last much longer. Are
you ready Stacey? I’m about to bust my nut in your mouth.”

“Mmmm-hmmm,” was all I could manage with my mouth full of cock.

“Now, Stacey,” Marisa said, “be sure to get her cock out of your throat
when she starts coming. She needs to shoot her entire load in your
mouth. I want you to hold it in your mouth so I can see it.”

“Mmmm-hmmm,” I said again.

Kayla’s thrusts became slow and deliberate; she pulled her cock nearly
out of my mouth before shoving it back down my throat. I could tell she
was close to the edge.

“Fuuuuck — your mouth — is so — fucking — sexy,” she said,
punctuating her speech with thrusts down my throat. When she said “sexy”
she pulled me in, leaving her cock down my throat and mashing her balls
against my chin. “Here it comes, Stacey! Get ready for my hot steamy

She pulled back until only the head of her cock remained in my mouth. I
caught a quick breath and closed my lips back around her cock. I used
one hand to keep stroking as much of her shaft as I could while the other
hand cupped and massaged her balls. The whole time my tongue was
swirling around her cock head. Then she erupted.

I have no idea how big the average cumshot is, but this was much, much
more than I had ever produced. The first mighty spurt hit the back of my
throat, causing me to cough a little; the second spurt was bigger than
the first, but I was ready for it. My mouth was filling up, not like my
cheeks were bursting, but it was going to be a problem soon to keep the
cum in my mouth with her cock still in there. I know when I come I
typically spurt 4-5 times. I lost count of Kayla’s, but it seemed like
it must have been 8-10 times. I felt her balls spasm with each spurt and
each one seemed to produce at least as much cum as the first. Like a
disembodied voice, I heard myself moaning as she pumped her cum into my

She finally stopped coming and pulled her cock from between my lips. It
seemed like I could feel the sperm swimming around in the puddle of cum
in my mouth. It was warm and tasted manly. I felt so utterly depraved,
kneeling as I was with a dildo shoved up my ass and a stranger’s load of
cum filling my mouth.

“Show me,” Marisa said. I opened my mouth, tipping my head back a bit to
keep it from running over my bottom lip. “Very good, now swallow it.”

I swallowed Kayla’s huge load, taking a couple of swallows to make sure
my mouth was clear. I immediately moved forward to suck Kayla’s cock
back into my mouth, trying to milk the last drops of her cum from her
balls and licking her shaft and head clean. I wanted more; so much more.

“Damn,” Kayla said, “this one sure is hungry for it.”

“Very good, Stacey,” Marisa said. “I think, no, I know you will do very

I don’t know why, but I kept sucking Kayla’s cock and soon I felt it
growing hard again. I groped her balls and rubbed her ass; I even
fondled her “breasts” through the satin cups of her babydoll. It was
such a sexy feeling knowing that her cock was responding to my touch.

“Stacey, are you hungry for more?” Kayla asked.

“I am, Kayla,” I replied, “I want to taste another load from you, but I
want to feel you in my ass first.” I looked over at Marisa. “If that’s

“Well, my work here is done,” Marisa said, “and so is yours, Kayla.
You’re both off the clock as far as I’m concerned.”

< to be continued >

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