Maid to Order mdash Initiation Part 2
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Maid To Order — Introduction (Part 1) free porn video
Maid to Order -- Introduction (Part 1)
Like many married crossdressers, I do most of my dressing when either I
am travelling for work, or when my wife is travelling with her job. She
knows I dress, but isn't thrilled with the prospect since I work for a
prominent business member of our small community. She's afraid that if
my secret is ever "discovered" that it will have consequences for both my
job and my employer. I have tried and tried to stop; to resist the urge.
I have completed the binge-purge cycle so many times I have lost count
(not to mention literally thousands of dollars in lingerie, shoes, and
sex toys).
On my most recent trip, when I arrived at the hotel I was eager to check
in and get settled. It was a hotel my company frequently used in this
particular city, and they welcomed me back. Like so many business
travelers, I hung my suits and shirts. I unpacked my other clothes--
underwear, undershirts, etc., placing them neatly into dresser drawers.
Then, unlike most businessmen, I unpacked my lingerie.
For some reason, I always lay my "girlie" things out all over the bed
before deciding where to stash them. This particular stay was going to
be nearly a full week, so I had over-packed; bringing quite an assortment
of bras, panties, garter belts, babydolls, stockings, and heels. I also
brought along some of my favorite toys--butt plugs, bigger butt plugs,
and my newest favorite, a ultra-realistic cock with balls that attached
to an inflatable ball so it could be rode.
My cock grew steadily harder as I unpacked and "inventoried" all my
things, laying matching sets together and arranging them as they might be
worn (bras above panties, etc.). My carnal desire finally got the better
of me so I grabbed a pair of crotchless panties and my Doc Johnson Medium
Pleasure Plug buttplug--basically a 4-inch cock with a wide base--and
headed for the vanity mirror.
I quickly stripped out of my mundane "boy" clothes and stood naked in
front of the mirror. My cock had softened a little and pre-cum oozed
from the tip. I squeezed it out onto my finger and licked it off,
enjoying the taste. I thrilled at the touch of the cool satin as I
pulled the panties up my legs. The panties were black satin and two thin
pink bows on the front accented the center seam and opening of the open
crotch; two more bows did the same on the back. The sides were high-cut
but still covered most of my ass; and my cock, getting hard once more,
was sticking obscenely out the front.
I squeezed the pre-cum from my cock again, this time smearing it all over
the cock head of the butt plug. I eagerly licked it off, taking the full
insertable length into my mouth and slobbering on it like a cock-hungry
slut. I smeared more pre-cum on it and sucked on it some more.
I posed and preened in front of the mirror, admiring my silhouette with
my own hard cock sticking out in front of my black panties while my
buttplug was in my mouth. I looked so nasty! I continued to lick my
pre-cum as I teased my hard cock.
When I couldn't contain my desire any longer, I pulled the bottle of
Astroglide from my shaving kit, applied a generous coating to the plug
and a few fingertips' worth to my hungry asshole and inserted the
buttplug. The realistic cockhead felt great as it opened my ass. With
the tip inside I continued to push, enjoying the sensation as the head
penetrated me deeper and the shaft stretched me just that little bit
more. When I felt the end of the tapered shaft approaching, I pulled it
all of the way out and re-inserted it slowly one more time before using
it to fuck my ass for a few minutes.
I looked over my shoulder from time to time, enjoying how I looked bent
over in the mirror as I used the buttplug like a dildo. My cock was
still hard and leaking pre-cum, which was creating a small puddle on the
floor between my feet. I finally pulled it out one last time and slid
the entire length inside me with one push, feeling my ass close on the
tapered end, seating the buttplug deliciously in place. A sudden nasty
impulse struck me and before I could talk myself out of it, I knelt on
the floor and licked the puddle of pre-cum from the tile.
I went back into the room, enjoying the feel of having a plug up my ass.
Although I didn't have a bra to match my crotchless panties, I did pull
on a pair of seamed black stay-up stockings and put on my favorite pair
of black pumps. I rearranged and puttered around with my collection of
lingerie, selecting a different outfit to wear as I continued the
evening's activities.
Just as I had finished making my initial preparations, my room phone
rang. Damn! I minced over to the phone and answered it. It was my
boss, telling me that his flight was getting in late and that I needed to
meet this week's client for drinks and dinner in less than an hour! If
my boss had only known what I was dressed like on the other end of the
phone!! Ordinarily, it would not have been a big deal, but as it was, I
had to first undress and then get dressed in my "boy" clothes again. I
assured him I would be there and hung up the phone, more than a little
disappointed at being interrupted.
I walked back to the vanity area and picked up my clothes, enjoying the
feel of the plug some more as I bent over. As I walked back into the
room a naughty and sexy idea suddenly came to me--an idea that would have
freaked out my wife if she had known.
I slipped out of the crotchless panties and selected a pair of hipster
panties from the bed. They were purple and black zebra print on the
satin center panel with micro fiber floral lace side panels. The keyhole
full-back was the same purple all in microfiber and black satin bows
accented the middles of both the front and the back. After letting it
all hang out in the crotchless panties, I loved the way the satin and
lace panties cupped and caressed my smooth cock and balls.
I left the stay-up black stockings on and slipped the camisole that
matched the panties over my head. The lined cups were the same soft
floral lace as the panty side panels with a black satin bow between them.
The front panel of the camisole was the same purple and black zebra
pattern and the back was plain purple microfiber.
I pulled my pants on over my stockings and panties, pulled socks on my
feet to cover the stockings below the pants, then slipped back into my
collared shirt and pulled a sweater on over that. I checked my
appearance in the mirror. Only I would know what I had on underneath my
boring "boy" clothes--sexy lingerie. I also thrilled at the idea of
secretly having a 4-inch cock buttplug up my ass the entire evening.
Dinner was boring, as I expected. As I rocked side-to-side or forwards
and backwards, enjoying the sensation of the buttplug with each shift of
my weight, our client seemed to think I was way more interested in the
conversation we were having than I really was. We drank quite a bit,
both in the bar before dinner, wine with dinner, and more cocktails after
dinner.
I excused myself several times to go to the bathroom, each time using a
stall so I could pull my pants half-down to admire my panties and
stocking tops. After my second trip to the head, as I was joining our
client at the table, he glanced up and said, "Hey, your fly's open." I
flushed with only slight embarrassment, but my brain immediately threw
the paranoia switch, wondering if he had glimpsed either my panties or
the hem of my camisole, which thankfully did not have lace trim. No
matter, I told myself dismissively, the most he could have seen was a
flash of purple zebra print and with some of the crazy designs men's
underwear sported today I didn't feel I had any cause to worry.
He didn't seem to make anything more out of it and our dinner concluded
without further incident. We parted ways and I grabbed a cab back to the
hotel. I wasn't stupid-drunk, but I was well on the way. I was anxious
to get back to my room and to my planned activities. As the elevator
rose, I leaned hard against the hand rail, rubbing my ass and pushing
against the buttplug, further fueling my desires.
I closed the door behind me and practically ripped my clothes off,
stripping down to the camisole, panties and stockings as I moved into the
room and leaving a trail of boring clothes behind me. I grabbed my
breast forms and slipped them into the cups of the camisole and stepped
back into my black patent leather pumps. Although it wasn't the outfit I
had planned to wear tonight, I was horny beyond belief and it would have
to do.
I grabbed a few more of my toys and went back into the vanity area. I
admired my reflection in the mirror as I bent over and pulled my panties
half-down. I reached behind and pulled the plug from my ass. As it had
been there without additional lube for the better part of three hours, it
was a little resistant, but still came out with very little effort. I
picked up another plug.
I applied a generous amount of lube to the next size plug--my Doc Johnson
Classic Thin Tool. It was twice as long as the other buttplug and had an
enlarged head. I always loved the way the extra width spread me wider--
especially how it felt opening my asshole. The insertable shaft was over
7-inches long that tapered to a thinner end but was covered with a smooth
veined texture with plenty of bumps and ridges for added sensation and
pleasure.
I placed the new buttplug against my asshole and pushed, moaning just a
little as the head opened me wide. It was smooth so it easily popped
inside. As I often did with this particular toy, I immediately pulled it
back out and inserted it again. And again. And again. Each time I
loved the way the enlarged head felt as my asshole stretched to
accommodate it. I finally pushed and shoved all seven inches inside of
me. I used it like a dildo--just as I had done with my smaller plug
earlier--for a few minutes, finally leaving it in and pulling my panties
back up.
Next, I picked up the E-Z Rider Rocker ball. I opened the valve and
started to inflate the 8-inch wide flesh-colored "beach ball." This was
my least favorite task; I prefer sucking to blowing! After several
minutes of huffing and puffing, it was finally done. I took the red Vac-
U-Loc plug base and fitted it snugly into its slot on the ball. Although
my cock had gone from soft to hard back to soft while I was getting
things ready, it was rock hard now with anticipation.
I didn't feel like taking the time to do a full makeup job, so I just
quickly applied a coat of lipstick--a light pink NARS color called Funny
Face--and some eye shadow. I knelt on the floor and held the dildo that
was going to be attached to the ball soon right at waist height against
the counter. It was another Doc Johnson product--the 7-inch Thin
Realistic cock. Overall it was 8-inches long with 7 inches to insert;
and a comfortable 1 1/2 inches wide and just over 5 inches around. The
slant of this model made it hang realistically as I held it by the balls.
It looked as real as my own aching cock, white crisscrossed with blue
veins and with a well-defined head, though it was slightly longer but
thinner.
I have never sucked a real cock before, but this one not only looked like
the real thing, but felt like I assumed a real cock would in my mouth.
It was soft but firm in all the right places. I could hardly wait to get
it in my "right place" -- balls deep in my ass!
I licked the head and then opened my mouth, taking it inside. I slurped
noisily on the head and then licked and slobbered up and down the shaft.
I licked the balls and then the shaft some more. I opened my mouth wide
and shoved the entire length down my throat. I bobbed my head up and
down, fucking my throat with it momentarily, and coughing wetly as I
finally gagged and came up for air. I always sucked on my dildos with
the fantasy in the back of my mind that one day some lucky guy (or other
t-girl) would appreciate all my practice.
I picked up my other dildo. It was yet a fourth Doc Johnson product. I
love those Doc Johnson Johnsons! It was the much-bigger Realistic 8-inch
dildo. Overall it was 9 inches long, with 8 inches of insertable length.
It was thick--over 2 inches wide and 6 1/2 inches around and always felt
great! It had a well-shaped head with a thick ridge and the shaft was
solid and meaty.
I held it at the same level as the other dildo, and now I alternated back
and forth, sucking first one, then the other. I licked both shafts,
slathered my tongue all over the balls, and back up and down all sides of
them. I deep-throated the thinner one easily, using it to fuck my
throat. I tried, as I always did, to get the bigger one down my throat--
unsuccessfully. I tried again and again and gagged and coughed each
time.
I couldn't wait to have it in both ends, so I gave my 7-inch Thin cock a
final deep-throat and a kiss before giving the attachment hole a quick
puff of the dry lubricant and attaching it to the Rocker Ball. I grabbed
the thick dildo, my Astroglide, and a towel and went into the bedroom. I
rearranged the other bed (the one without all my lingerie spread across
it) to my liking and climbed onto it. I pulled my panties down to just
below my ass and pulled the buttplug, placing it on the towel spread out
beside me.
I applied a generous amount of lube to the dildo before positioning the
ball between my feet behind me. I lined the head of the cock up with my
hole and inserted it. It went in pretty easily, but I only inserted it
about halfway. As it was longer than the buttplug and the shaft was
thicker, I enjoyed the sensation of having a bigger "dick" in my ass. I
pulled it out and inserted it again, this time humping back against the
ball, but only using half the length to fuck myself with.
This was my favorite toy for a nice slow comfortable fuck. I pulled it
out, applied more lube, and stuck it back in again, this time going a
little deeper. My hard cock, still inside the front of my half-down
panties, was leaking pre-cum and front of the panties was soaked. I
stroked my cock inside the slippery satin and lace, teasing myself as I
rocked back and forth humping the dildo inside of me. After just a few
more minutes of pleasuring myself, the need for an increased pace with
the whole dildo inside me was just too great.
I sighed as I pulled the dildo from my ass, missing it and desiring it
inside me again almost as soon as it was removed. I stood up and quickly
pulled my panties all the way down, stepping out of them and kicking them
away from me in my haste to get back on the bed. My cock bobbed free and
I stroked it a few times, licking the pre-cum off my fingers. I applied
still more lube to the dildo, generously coating the shaft from the tip
to the balls.
I re-positioned myself, tucked the ball between my feet once more, lined
the dildo up against my hungry asshole and sank back against it. As my
rubber lover opened me once more I moaned. I pushed until the entire
length was inside me and I felt its balls pressed against my own. I
ground against it for a bit, picking up the bigger dildo and licking it
as I did so. I positioned the larger dildo against the headboard and
licked and sucked on it as I started fucking myself in the ass with the
other.
Sometimes I bucked against the Rocker ball, moving my ass back and forth,
pulling the dildo almost all the way out before plunging it back inside
me in long deep strokes. Sometimes I used shorter strokes, enjoying a
quicker pace as I humped against the ball. All the while I slobbered
over and sucked the other dildo in my mouth, gagging as I continued
trying to deep throat it. I was getting it in both ends like a wanton
slut and enjoying every depraved minute of it.
I swapped hands now and held the dildo I was sucking with my left hand so
I could stroke my own cock with my right. Now I had three cocks to play
with! I knew I wasn't going to last long and a quick glance at the alarm
clock told me morning was going to come all too-soon. I quickened my
pace both with my right hand and with the dildo fucking my ass. I was
crazy with the desire to come, and impaled myself on the dildo with one
final, long tip-to-balls thrust. I dropped the large dildo I had been
sucking on and my body shook with the intensity of my orgasm.
I came hard, shooting a thick creamy load into my cupped left hand as I
felt my asshole spasm, clenching itself around the shaft of the dildo in
my ass. I heard myself groan aloud as I came, the sound seeming to come
from somewhere else in the room. I slumped forward onto my elbows,
careful not to spill a drop of the load in my left hand. The Rocker ball
was wedged against a pillow and didn't move much, leaving the dildo deep
in my ass.
I picked up the larger dildo and dipped and rubbed it in my cum-filled
hand. I licked the cum from it, and then reapplied more; using the dildo
as a utensil to eat my load with. When it was nearly gone, I stroked the
dildo with my left hand, making a sexy squishing sound as I rubbed the
rest of the cum all over it. I slapped it against my face several times,
enjoying the hefty weight as it smacked me before licking it clean.
I slumped all the way forward now, exhausted from my efforts and
completely spent from my orgasm. With my face sticky with my own cum and
the dildo still buried in my ass I closed my eyes, enjoying the
"afterglow" for a minute before getting up to clean myself off and tidy
up.
The ringing of my room phone jolted me awake.
I cursed out loud, jumping up off the bed. The dildo had obviously
slipped out at some point in time while I had slept. I answered the
phone, standing there in just my camisole, stockings and heels.
"Uh, hello?" I tried not to sound like I had just woke up.
"I'm heading downstairs for breakfast, are you coming?" It was my boss.
"There are some things we need to discuss before the meeting this
morning."
"Well, I was just going to have some coffee in my room, but, sure. Give
me 20 minutes to get myself together."
I hung up the phone and cursed again. I grabbed the toys off the bed and
took them with me to the shower, pulling the dildo off the Rocker ball as
I went. I stripped off and showered in record time, using the hotel
shampoo and soap to clean not only me but also my dildos and buttplugs.
I shaved in the shower as well, grateful that I didn't cut myself in my
haste.
I raced through the rest of my morning routine, applying deodorant and
aftershave and practically jumping into my shirt and pants. I surveyed
the bed covered with all my bras, panties, garter belts and other
lingerie. There was no time to fold them and put them all away as I
normally would, so I just grabbed it all up and started shoving it in
drawers. I hastily covered it as best as I could under my other clothes,
figuring that the odds of housekeeping rooting through my drawers were
small indeed.
I tossed all my toys into my suitcase along with the lube. I had to
leave the Rocker ball inflated and shoved it into the suitcase as well.
Back in the vanity area I shoved all my personal effects--including my
makeup--into my shaving kit and closed it, leaving it on the counter. I
went back in my room, threw my laptop and other things together in my
satchel, keeping a close eye on the clock. I had three minutes left!
I took a last quick look over the room, grabbed the towel off the bed I
had slept in, and tossed it in the pile with the other one as I headed
for the door.
Downstairs, I joined my boss in the hotel restaurant. He told me I
looked like shit, asked how I had slept; and then launched into strategy
for today's meetings with our new client. As he droned on (I knew he
would do most of the talking today anyway), I mentally checked off that I
had put everything away--lingerie, toys, makeup. Okay, I could relax a
little.
The days' meetings were as boring as I expected, but very profitable.
The boss said he was going to dinner with the CEO of our new client and
that maybe we could cut the trip short. We grabbed a few drinks in the
hotel bar when we got back. He wanted to be sure I wasn't insulted about
being left out of dinner plans. Not a chance! I assured him it was all
good and that I would find some way to entertain myself tonight.
I was anxious to get back to my room so I could get out of my suit and
into some more of my sexy lingerie. I looked forward to another night on
the Rocker ball fucking myself with my dildos; only tonight I knew I
would have enough time to use the large dildo as well. I could feel my
cock stir at the thought of opening my ass up over 2 inches wide.
I finished my drink and excused myself. As I rode the elevator up to my
floor, my mind was already wandering, thinking about what outfit I was
going to wear. I opened the door to my room and went straight to the
bathroom. As I left the toilet I was already stripping out of my suit.
As I opened the sliding mirrored door to the closet, something in the
reflection caught my eye. As I turned around, my heart leaped into my
throat.
An outfit was neatly arranged on the foot of the bed. I recognized the
blue ruffled bra, panty and garter belt set as part of my collection.
Cream colored lace-top stockings were neatly folded next to it, and my
white patent leather pumps were on the floor. Next to the lingerie was
one of my toys--the Anal Twist, one I hadn't used last night--as well as
my bottle of Astroglide.
My mind was racing, close to panic. I turned and opened my dresser
drawers. It was immediately obvious that everything had been rearranged.
My "boy" clothes were stacked to one side and my "girlie" lingerie had
been neatly folded and arranged beside it. In another drawer a towel had
been used as a liner and my toys were all laid out in an orderly manner,
including the Rocker ball which had been deflated.
I turned back to the bed, my head reeling, and then I saw it--there was a
note on the pillow with something under it. I walked over, my heart
racing, and picked up both items. It was my panties from last night!
They were kind of twisted up and the front was dried and crusty from all
of the pre-cum it had absorbed. In my haste to kick them off last night-
-and getting ready this morning--I must have missed them. Which means
they were found by... I looked at the note.
It was neatly written in feminine handwriting on hotel room stationary.
It read:
I will return to your room at 8:30pm. I expect you to be wearing the
outfit I have laid out for you. When I enter I expect to see you facing
the door and bent over the ottoman with the anal toy inserted up your ass
as deep as it is designed to go. Feel free to wear whatever makeup you
feel appropriate. Do not attempt to lock or bar your door.
M.
My mind raced; a hundred different scenarios running through my head.
Did she (I assumed "she") know who I was? Obviously, if she had any kind
of access to the hotel's computer system. Was she serious? What was she
going to do to me when she got here? What could or would she do to me if
I blew her off? Did I want to find out either way? Nothing like this
had ever happened in my 15 years as a dedicated crossdresser and I was
scared! My wife's worst fear seemed to be unfolding before me.
I looked at the clock. It was already 7:30. I didn't have a lot of time
to weigh my options. I had never cheated on my wife. I often fantasized
about contacting and meeting other crossdressers while I travelled. As I
sucked on my dildos I wondered what a real cock would feel like in my
mouth. As I fucked myself in the ass I imagined what it would feel like
to have another person behind me, gripping my hips tightly. I looked at
the clock again. It was 7:40.
Finally, I decided that I would have to see where this was going so that
I could find a way out of it--if indeed this was something I needed to
get out of. I went to the closet, stripped, and hung up my clothes;
leaving my t-shirt and underwear on the floor of the closet and closing
the door. My cock was half-hard and already oozing pre-cum, which I
wiped away and licked off my fingers.
I picked up the padded push-up bra first, placing my arms into the straps
and fastening it behind me. It was a light blue satin, with a sexy
ruffle of the same color that ran across the top of the seamed bra cups
from one strap to the other in a single piece. Two small satin bows
trimmed the other end of the bra straps on the back of the bra. I didn't
know exactly how much personal initiative she wanted me to take, but I
opened the "toy drawer" and pulled out my C-cup breast forms. I fitted
them into the bra, adjusting them and then cupping them together, taking
a moment to enjoy the way they felt, filling my bra.
I didn't know what her plans were, so I proceeded the way I normally
would. I pulled the thong panties up my legs. They were the same light
blue satin, and were plain except for a satin bow centered at the waist.
The garter belt came next. Made of the same blue satin, there was a
smooth panel of satin on the front between the garters with a satin bow
trimming the waist at the center. Five rows of ruffles ran from either
side of the front panel all the way around the hips and to the back where
the hook and eye closure fastened it.
I checked the clock again--8:00. I picked up the stockings, rolling them
up my legs with a practiced hand. I attached them to the garters, and
although they weren't seamed, I still checked to make sure they were on
straight and that my garters weren't crooked.
I stepped into my white patent leather shoes--D'orsay-style 5-inch heels
with closed toes and a sexy ankle strap. I bent over, fastening each
ankle strap and then stood. It had been awhile since I had worn these
particular heels and I minced my way to the vanity, getting used to the
height. The clicking of my heels on the tile floor gave me a certain
thrill, as it always seemed to. I had just 20 minutes to apply some
makeup, get the anal toy up my ass and "assume the position."
I applied a light coat of foundation and then applied a blend of several
colors of eye shadow. I knew I was running out of time so I skipped the
eyeliner pencil and went straight to the mascara. I dusted my cheeks
with a little blush, outlined my lips with lip pencil, and then finally
applied a generous coating of my "standby" lipstick--a rich red called
Caprice by Lancome. I went back in to the bedroom and looked at the
clock--I had just 8 minutes to finish.
I pushed the ottoman away from the chair, moving it more to the middle of
the open area in my room. I grabbed the Anal Twist and the lube and
knelt on the opposite side of the ottoman. The Anal Twist was an 11 1/2-
inch long non-realistic dildo with a 4-inch handle on one end. It was
just over an inch wide and had 8 rings that got progressively wider. I
love the way the rings provide a unique sensation as it moves in and out
of my ass.
I pulled my thong panties to one side, applied a generous amount of lube
to both my ass and the toy, lined it up against my puckered hole, and
penetrated myself. Since the toy was basically smooth with no defined
"head" like a cock and was just over an inch wide it went in with very
little effort up to the 4th or 5th ring. I pulled it out, applied more
lube, and inserted it once more, this time going up to the 6th ring. I
gripped the handle and started fucking my ass with it, going deeper with
each stroke. It's funny how I hadn't noticed how soft my cock had gotten
during all of this, but I certainly noticed it growing again, straining
against the smooth satin of the panties under the wide garter belt.
I pulled the dildo out one more time, applied one final generous coat of
lube to it, and then pushed it back in my ass until only the ring just
above the handle remained outside of my ass. I looked at the clock--
8:28, nope 8:29. Wow, I thought, that was cutting it very close. I
propped myself on my elbows, my ass sticking out behind me. I wished for
a mirror on the wall. I could only imagine how silly I looked bent over
the ottoman with a 4-inch dildo handle jutting out from my ass.
The clock turned to 8:30. I could feel my heart beating like a drum in
my chest and I felt a little nauseous. Nothing happened. I quickly
looked at the door. Had I locked it or flipped the bar when I came in?
Nope. Finally, I heard a quiet knock on the door.
"Housekeeping," a woman's voice said. I heard a keycard in the door.
< to be continued >
Like many married crossdressers, I do most of my dressing when either I
am travelling for work, or when my wife is travelling with her job. She
knows I dress, but isn't thrilled with the prospect since I work for a
prominent business member of our small community. She's afraid that if
my secret is ever "discovered" that it will have consequences for both my
job and my employer. I have tried and tried to stop; to resist the urge.
I have completed the binge-purge cycle so many times I have lost count
(not to mention literally thousands of dollars in lingerie, shoes, and
sex toys).
On my most recent trip, when I arrived at the hotel I was eager to check
in and get settled. It was a hotel my company frequently used in this
particular city, and they welcomed me back. Like so many business
travelers, I hung my suits and shirts. I unpacked my other clothes--
underwear, undershirts, etc., placing them neatly into dresser drawers.
Then, unlike most businessmen, I unpacked my lingerie.
For some reason, I always lay my "girlie" things out all over the bed
before deciding where to stash them. This particular stay was going to
be nearly a full week, so I had over-packed; bringing quite an assortment
of bras, panties, garter belts, babydolls, stockings, and heels. I also
brought along some of my favorite toys--butt plugs, bigger butt plugs,
and my newest favorite, a ultra-realistic cock with balls that attached
to an inflatable ball so it could be rode.
My cock grew steadily harder as I unpacked and "inventoried" all my
things, laying matching sets together and arranging them as they might be
worn (bras above panties, etc.). My carnal desire finally got the better
of me so I grabbed a pair of crotchless panties and my Doc Johnson Medium
Pleasure Plug buttplug--basically a 4-inch cock with a wide base--and
headed for the vanity mirror.
I quickly stripped out of my mundane "boy" clothes and stood naked in
front of the mirror. My cock had softened a little and pre-cum oozed
from the tip. I squeezed it out onto my finger and licked it off,
enjoying the taste. I thrilled at the touch of the cool satin as I
pulled the panties up my legs. The panties were black satin and two thin
pink bows on the front accented the center seam and opening of the open
crotch; two more bows did the same on the back. The sides were high-cut
but still covered most of my ass; and my cock, getting hard once more,
was sticking obscenely out the front.
I squeezed the pre-cum from my cock again, this time smearing it all over
the cock head of the butt plug. I eagerly licked it off, taking the full
insertable length into my mouth and slobbering on it like a cock-hungry
slut. I smeared more pre-cum on it and sucked on it some more.
I posed and preened in front of the mirror, admiring my silhouette with
my own hard cock sticking out in front of my black panties while my
buttplug was in my mouth. I looked so nasty! I continued to lick my
pre-cum as I teased my hard cock.
When I couldn't contain my desire any longer, I pulled the bottle of
Astroglide from my shaving kit, applied a generous coating to the plug
and a few fingertips' worth to my hungry asshole and inserted the
buttplug. The realistic cockhead felt great as it opened my ass. With
the tip inside I continued to push, enjoying the sensation as the head
penetrated me deeper and the shaft stretched me just that little bit
more. When I felt the end of the tapered shaft approaching, I pulled it
all of the way out and re-inserted it slowly one more time before using
it to fuck my ass for a few minutes.
I looked over my shoulder from time to time, enjoying how I looked bent
over in the mirror as I used the buttplug like a dildo. My cock was
still hard and leaking pre-cum, which was creating a small puddle on the
floor between my feet. I finally pulled it out one last time and slid
the entire length inside me with one push, feeling my ass close on the
tapered end, seating the buttplug deliciously in place. A sudden nasty
impulse struck me and before I could talk myself out of it, I knelt on
the floor and licked the puddle of pre-cum from the tile.
I went back into the room, enjoying the feel of having a plug up my ass.
Although I didn't have a bra to match my crotchless panties, I did pull
on a pair of seamed black stay-up stockings and put on my favorite pair
of black pumps. I rearranged and puttered around with my collection of
lingerie, selecting a different outfit to wear as I continued the
evening's activities.
Just as I had finished making my initial preparations, my room phone
rang. Damn! I minced over to the phone and answered it. It was my
boss, telling me that his flight was getting in late and that I needed to
meet this week's client for drinks and dinner in less than an hour! If
my boss had only known what I was dressed like on the other end of the
phone!! Ordinarily, it would not have been a big deal, but as it was, I
had to first undress and then get dressed in my "boy" clothes again. I
assured him I would be there and hung up the phone, more than a little
disappointed at being interrupted.
I walked back to the vanity area and picked up my clothes, enjoying the
feel of the plug some more as I bent over. As I walked back into the
room a naughty and sexy idea suddenly came to me--an idea that would have
freaked out my wife if she had known.
I slipped out of the crotchless panties and selected a pair of hipster
panties from the bed. They were purple and black zebra print on the
satin center panel with micro fiber floral lace side panels. The keyhole
full-back was the same purple all in microfiber and black satin bows
accented the middles of both the front and the back. After letting it
all hang out in the crotchless panties, I loved the way the satin and
lace panties cupped and caressed my smooth cock and balls.
I left the stay-up black stockings on and slipped the camisole that
matched the panties over my head. The lined cups were the same soft
floral lace as the panty side panels with a black satin bow between them.
The front panel of the camisole was the same purple and black zebra
pattern and the back was plain purple microfiber.
I pulled my pants on over my stockings and panties, pulled socks on my
feet to cover the stockings below the pants, then slipped back into my
collared shirt and pulled a sweater on over that. I checked my
appearance in the mirror. Only I would know what I had on underneath my
boring "boy" clothes--sexy lingerie. I also thrilled at the idea of
secretly having a 4-inch cock buttplug up my ass the entire evening.
Dinner was boring, as I expected. As I rocked side-to-side or forwards
and backwards, enjoying the sensation of the buttplug with each shift of
my weight, our client seemed to think I was way more interested in the
conversation we were having than I really was. We drank quite a bit,
both in the bar before dinner, wine with dinner, and more cocktails after
dinner.
I excused myself several times to go to the bathroom, each time using a
stall so I could pull my pants half-down to admire my panties and
stocking tops. After my second trip to the head, as I was joining our
client at the table, he glanced up and said, "Hey, your fly's open." I
flushed with only slight embarrassment, but my brain immediately threw
the paranoia switch, wondering if he had glimpsed either my panties or
the hem of my camisole, which thankfully did not have lace trim. No
matter, I told myself dismissively, the most he could have seen was a
flash of purple zebra print and with some of the crazy designs men's
underwear sported today I didn't feel I had any cause to worry.
He didn't seem to make anything more out of it and our dinner concluded
without further incident. We parted ways and I grabbed a cab back to the
hotel. I wasn't stupid-drunk, but I was well on the way. I was anxious
to get back to my room and to my planned activities. As the elevator
rose, I leaned hard against the hand rail, rubbing my ass and pushing
against the buttplug, further fueling my desires.
I closed the door behind me and practically ripped my clothes off,
stripping down to the camisole, panties and stockings as I moved into the
room and leaving a trail of boring clothes behind me. I grabbed my
breast forms and slipped them into the cups of the camisole and stepped
back into my black patent leather pumps. Although it wasn't the outfit I
had planned to wear tonight, I was horny beyond belief and it would have
to do.
I grabbed a few more of my toys and went back into the vanity area. I
admired my reflection in the mirror as I bent over and pulled my panties
half-down. I reached behind and pulled the plug from my ass. As it had
been there without additional lube for the better part of three hours, it
was a little resistant, but still came out with very little effort. I
picked up another plug.
I applied a generous amount of lube to the next size plug--my Doc Johnson
Classic Thin Tool. It was twice as long as the other buttplug and had an
enlarged head. I always loved the way the extra width spread me wider--
especially how it felt opening my asshole. The insertable shaft was over
7-inches long that tapered to a thinner end but was covered with a smooth
veined texture with plenty of bumps and ridges for added sensation and
pleasure.
I placed the new buttplug against my asshole and pushed, moaning just a
little as the head opened me wide. It was smooth so it easily popped
inside. As I often did with this particular toy, I immediately pulled it
back out and inserted it again. And again. And again. Each time I
loved the way the enlarged head felt as my asshole stretched to
accommodate it. I finally pushed and shoved all seven inches inside of
me. I used it like a dildo--just as I had done with my smaller plug
earlier--for a few minutes, finally leaving it in and pulling my panties
back up.
Next, I picked up the E-Z Rider Rocker ball. I opened the valve and
started to inflate the 8-inch wide flesh-colored "beach ball." This was
my least favorite task; I prefer sucking to blowing! After several
minutes of huffing and puffing, it was finally done. I took the red Vac-
U-Loc plug base and fitted it snugly into its slot on the ball. Although
my cock had gone from soft to hard back to soft while I was getting
things ready, it was rock hard now with anticipation.
I didn't feel like taking the time to do a full makeup job, so I just
quickly applied a coat of lipstick--a light pink NARS color called Funny
Face--and some eye shadow. I knelt on the floor and held the dildo that
was going to be attached to the ball soon right at waist height against
the counter. It was another Doc Johnson product--the 7-inch Thin
Realistic cock. Overall it was 8-inches long with 7 inches to insert;
and a comfortable 1 1/2 inches wide and just over 5 inches around. The
slant of this model made it hang realistically as I held it by the balls.
It looked as real as my own aching cock, white crisscrossed with blue
veins and with a well-defined head, though it was slightly longer but
thinner.
I have never sucked a real cock before, but this one not only looked like
the real thing, but felt like I assumed a real cock would in my mouth.
It was soft but firm in all the right places. I could hardly wait to get
it in my "right place" -- balls deep in my ass!
I licked the head and then opened my mouth, taking it inside. I slurped
noisily on the head and then licked and slobbered up and down the shaft.
I licked the balls and then the shaft some more. I opened my mouth wide
and shoved the entire length down my throat. I bobbed my head up and
down, fucking my throat with it momentarily, and coughing wetly as I
finally gagged and came up for air. I always sucked on my dildos with
the fantasy in the back of my mind that one day some lucky guy (or other
t-girl) would appreciate all my practice.
I picked up my other dildo. It was yet a fourth Doc Johnson product. I
love those Doc Johnson Johnsons! It was the much-bigger Realistic 8-inch
dildo. Overall it was 9 inches long, with 8 inches of insertable length.
It was thick--over 2 inches wide and 6 1/2 inches around and always felt
great! It had a well-shaped head with a thick ridge and the shaft was
solid and meaty.
I held it at the same level as the other dildo, and now I alternated back
and forth, sucking first one, then the other. I licked both shafts,
slathered my tongue all over the balls, and back up and down all sides of
them. I deep-throated the thinner one easily, using it to fuck my
throat. I tried, as I always did, to get the bigger one down my throat--
unsuccessfully. I tried again and again and gagged and coughed each
time.
I couldn't wait to have it in both ends, so I gave my 7-inch Thin cock a
final deep-throat and a kiss before giving the attachment hole a quick
puff of the dry lubricant and attaching it to the Rocker Ball. I grabbed
the thick dildo, my Astroglide, and a towel and went into the bedroom. I
rearranged the other bed (the one without all my lingerie spread across
it) to my liking and climbed onto it. I pulled my panties down to just
below my ass and pulled the buttplug, placing it on the towel spread out
beside me.
I applied a generous amount of lube to the dildo before positioning the
ball between my feet behind me. I lined the head of the cock up with my
hole and inserted it. It went in pretty easily, but I only inserted it
about halfway. As it was longer than the buttplug and the shaft was
thicker, I enjoyed the sensation of having a bigger "dick" in my ass. I
pulled it out and inserted it again, this time humping back against the
ball, but only using half the length to fuck myself with.
This was my favorite toy for a nice slow comfortable fuck. I pulled it
out, applied more lube, and stuck it back in again, this time going a
little deeper. My hard cock, still inside the front of my half-down
panties, was leaking pre-cum and front of the panties was soaked. I
stroked my cock inside the slippery satin and lace, teasing myself as I
rocked back and forth humping the dildo inside of me. After just a few
more minutes of pleasuring myself, the need for an increased pace with
the whole dildo inside me was just too great.
I sighed as I pulled the dildo from my ass, missing it and desiring it
inside me again almost as soon as it was removed. I stood up and quickly
pulled my panties all the way down, stepping out of them and kicking them
away from me in my haste to get back on the bed. My cock bobbed free and
I stroked it a few times, licking the pre-cum off my fingers. I applied
still more lube to the dildo, generously coating the shaft from the tip
to the balls.
I re-positioned myself, tucked the ball between my feet once more, lined
the dildo up against my hungry asshole and sank back against it. As my
rubber lover opened me once more I moaned. I pushed until the entire
length was inside me and I felt its balls pressed against my own. I
ground against it for a bit, picking up the bigger dildo and licking it
as I did so. I positioned the larger dildo against the headboard and
licked and sucked on it as I started fucking myself in the ass with the
other.
Sometimes I bucked against the Rocker ball, moving my ass back and forth,
pulling the dildo almost all the way out before plunging it back inside
me in long deep strokes. Sometimes I used shorter strokes, enjoying a
quicker pace as I humped against the ball. All the while I slobbered
over and sucked the other dildo in my mouth, gagging as I continued
trying to deep throat it. I was getting it in both ends like a wanton
slut and enjoying every depraved minute of it.
I swapped hands now and held the dildo I was sucking with my left hand so
I could stroke my own cock with my right. Now I had three cocks to play
with! I knew I wasn't going to last long and a quick glance at the alarm
clock told me morning was going to come all too-soon. I quickened my
pace both with my right hand and with the dildo fucking my ass. I was
crazy with the desire to come, and impaled myself on the dildo with one
final, long tip-to-balls thrust. I dropped the large dildo I had been
sucking on and my body shook with the intensity of my orgasm.
I came hard, shooting a thick creamy load into my cupped left hand as I
felt my asshole spasm, clenching itself around the shaft of the dildo in
my ass. I heard myself groan aloud as I came, the sound seeming to come
from somewhere else in the room. I slumped forward onto my elbows,
careful not to spill a drop of the load in my left hand. The Rocker ball
was wedged against a pillow and didn't move much, leaving the dildo deep
in my ass.
I picked up the larger dildo and dipped and rubbed it in my cum-filled
hand. I licked the cum from it, and then reapplied more; using the dildo
as a utensil to eat my load with. When it was nearly gone, I stroked the
dildo with my left hand, making a sexy squishing sound as I rubbed the
rest of the cum all over it. I slapped it against my face several times,
enjoying the hefty weight as it smacked me before licking it clean.
I slumped all the way forward now, exhausted from my efforts and
completely spent from my orgasm. With my face sticky with my own cum and
the dildo still buried in my ass I closed my eyes, enjoying the
"afterglow" for a minute before getting up to clean myself off and tidy
up.
The ringing of my room phone jolted me awake.
I cursed out loud, jumping up off the bed. The dildo had obviously
slipped out at some point in time while I had slept. I answered the
phone, standing there in just my camisole, stockings and heels.
"Uh, hello?" I tried not to sound like I had just woke up.
"I'm heading downstairs for breakfast, are you coming?" It was my boss.
"There are some things we need to discuss before the meeting this
morning."
"Well, I was just going to have some coffee in my room, but, sure. Give
me 20 minutes to get myself together."
I hung up the phone and cursed again. I grabbed the toys off the bed and
took them with me to the shower, pulling the dildo off the Rocker ball as
I went. I stripped off and showered in record time, using the hotel
shampoo and soap to clean not only me but also my dildos and buttplugs.
I shaved in the shower as well, grateful that I didn't cut myself in my
haste.
I raced through the rest of my morning routine, applying deodorant and
aftershave and practically jumping into my shirt and pants. I surveyed
the bed covered with all my bras, panties, garter belts and other
lingerie. There was no time to fold them and put them all away as I
normally would, so I just grabbed it all up and started shoving it in
drawers. I hastily covered it as best as I could under my other clothes,
figuring that the odds of housekeeping rooting through my drawers were
small indeed.
I tossed all my toys into my suitcase along with the lube. I had to
leave the Rocker ball inflated and shoved it into the suitcase as well.
Back in the vanity area I shoved all my personal effects--including my
makeup--into my shaving kit and closed it, leaving it on the counter. I
went back in my room, threw my laptop and other things together in my
satchel, keeping a close eye on the clock. I had three minutes left!
I took a last quick look over the room, grabbed the towel off the bed I
had slept in, and tossed it in the pile with the other one as I headed
for the door.
Downstairs, I joined my boss in the hotel restaurant. He told me I
looked like shit, asked how I had slept; and then launched into strategy
for today's meetings with our new client. As he droned on (I knew he
would do most of the talking today anyway), I mentally checked off that I
had put everything away--lingerie, toys, makeup. Okay, I could relax a
little.
The days' meetings were as boring as I expected, but very profitable.
The boss said he was going to dinner with the CEO of our new client and
that maybe we could cut the trip short. We grabbed a few drinks in the
hotel bar when we got back. He wanted to be sure I wasn't insulted about
being left out of dinner plans. Not a chance! I assured him it was all
good and that I would find some way to entertain myself tonight.
I was anxious to get back to my room so I could get out of my suit and
into some more of my sexy lingerie. I looked forward to another night on
the Rocker ball fucking myself with my dildos; only tonight I knew I
would have enough time to use the large dildo as well. I could feel my
cock stir at the thought of opening my ass up over 2 inches wide.
I finished my drink and excused myself. As I rode the elevator up to my
floor, my mind was already wandering, thinking about what outfit I was
going to wear. I opened the door to my room and went straight to the
bathroom. As I left the toilet I was already stripping out of my suit.
As I opened the sliding mirrored door to the closet, something in the
reflection caught my eye. As I turned around, my heart leaped into my
throat.
An outfit was neatly arranged on the foot of the bed. I recognized the
blue ruffled bra, panty and garter belt set as part of my collection.
Cream colored lace-top stockings were neatly folded next to it, and my
white patent leather pumps were on the floor. Next to the lingerie was
one of my toys--the Anal Twist, one I hadn't used last night--as well as
my bottle of Astroglide.
My mind was racing, close to panic. I turned and opened my dresser
drawers. It was immediately obvious that everything had been rearranged.
My "boy" clothes were stacked to one side and my "girlie" lingerie had
been neatly folded and arranged beside it. In another drawer a towel had
been used as a liner and my toys were all laid out in an orderly manner,
including the Rocker ball which had been deflated.
I turned back to the bed, my head reeling, and then I saw it--there was a
note on the pillow with something under it. I walked over, my heart
racing, and picked up both items. It was my panties from last night!
They were kind of twisted up and the front was dried and crusty from all
of the pre-cum it had absorbed. In my haste to kick them off last night-
-and getting ready this morning--I must have missed them. Which means
they were found by... I looked at the note.
It was neatly written in feminine handwriting on hotel room stationary.
It read:
I will return to your room at 8:30pm. I expect you to be wearing the
outfit I have laid out for you. When I enter I expect to see you facing
the door and bent over the ottoman with the anal toy inserted up your ass
as deep as it is designed to go. Feel free to wear whatever makeup you
feel appropriate. Do not attempt to lock or bar your door.
M.
My mind raced; a hundred different scenarios running through my head.
Did she (I assumed "she") know who I was? Obviously, if she had any kind
of access to the hotel's computer system. Was she serious? What was she
going to do to me when she got here? What could or would she do to me if
I blew her off? Did I want to find out either way? Nothing like this
had ever happened in my 15 years as a dedicated crossdresser and I was
scared! My wife's worst fear seemed to be unfolding before me.
I looked at the clock. It was already 7:30. I didn't have a lot of time
to weigh my options. I had never cheated on my wife. I often fantasized
about contacting and meeting other crossdressers while I travelled. As I
sucked on my dildos I wondered what a real cock would feel like in my
mouth. As I fucked myself in the ass I imagined what it would feel like
to have another person behind me, gripping my hips tightly. I looked at
the clock again. It was 7:40.
Finally, I decided that I would have to see where this was going so that
I could find a way out of it--if indeed this was something I needed to
get out of. I went to the closet, stripped, and hung up my clothes;
leaving my t-shirt and underwear on the floor of the closet and closing
the door. My cock was half-hard and already oozing pre-cum, which I
wiped away and licked off my fingers.
I picked up the padded push-up bra first, placing my arms into the straps
and fastening it behind me. It was a light blue satin, with a sexy
ruffle of the same color that ran across the top of the seamed bra cups
from one strap to the other in a single piece. Two small satin bows
trimmed the other end of the bra straps on the back of the bra. I didn't
know exactly how much personal initiative she wanted me to take, but I
opened the "toy drawer" and pulled out my C-cup breast forms. I fitted
them into the bra, adjusting them and then cupping them together, taking
a moment to enjoy the way they felt, filling my bra.
I didn't know what her plans were, so I proceeded the way I normally
would. I pulled the thong panties up my legs. They were the same light
blue satin, and were plain except for a satin bow centered at the waist.
The garter belt came next. Made of the same blue satin, there was a
smooth panel of satin on the front between the garters with a satin bow
trimming the waist at the center. Five rows of ruffles ran from either
side of the front panel all the way around the hips and to the back where
the hook and eye closure fastened it.
I checked the clock again--8:00. I picked up the stockings, rolling them
up my legs with a practiced hand. I attached them to the garters, and
although they weren't seamed, I still checked to make sure they were on
straight and that my garters weren't crooked.
I stepped into my white patent leather shoes--D'orsay-style 5-inch heels
with closed toes and a sexy ankle strap. I bent over, fastening each
ankle strap and then stood. It had been awhile since I had worn these
particular heels and I minced my way to the vanity, getting used to the
height. The clicking of my heels on the tile floor gave me a certain
thrill, as it always seemed to. I had just 20 minutes to apply some
makeup, get the anal toy up my ass and "assume the position."
I applied a light coat of foundation and then applied a blend of several
colors of eye shadow. I knew I was running out of time so I skipped the
eyeliner pencil and went straight to the mascara. I dusted my cheeks
with a little blush, outlined my lips with lip pencil, and then finally
applied a generous coating of my "standby" lipstick--a rich red called
Caprice by Lancome. I went back in to the bedroom and looked at the
clock--I had just 8 minutes to finish.
I pushed the ottoman away from the chair, moving it more to the middle of
the open area in my room. I grabbed the Anal Twist and the lube and
knelt on the opposite side of the ottoman. The Anal Twist was an 11 1/2-
inch long non-realistic dildo with a 4-inch handle on one end. It was
just over an inch wide and had 8 rings that got progressively wider. I
love the way the rings provide a unique sensation as it moves in and out
of my ass.
I pulled my thong panties to one side, applied a generous amount of lube
to both my ass and the toy, lined it up against my puckered hole, and
penetrated myself. Since the toy was basically smooth with no defined
"head" like a cock and was just over an inch wide it went in with very
little effort up to the 4th or 5th ring. I pulled it out, applied more
lube, and inserted it once more, this time going up to the 6th ring. I
gripped the handle and started fucking my ass with it, going deeper with
each stroke. It's funny how I hadn't noticed how soft my cock had gotten
during all of this, but I certainly noticed it growing again, straining
against the smooth satin of the panties under the wide garter belt.
I pulled the dildo out one more time, applied one final generous coat of
lube to it, and then pushed it back in my ass until only the ring just
above the handle remained outside of my ass. I looked at the clock--
8:28, nope 8:29. Wow, I thought, that was cutting it very close. I
propped myself on my elbows, my ass sticking out behind me. I wished for
a mirror on the wall. I could only imagine how silly I looked bent over
the ottoman with a 4-inch dildo handle jutting out from my ass.
The clock turned to 8:30. I could feel my heart beating like a drum in
my chest and I felt a little nauseous. Nothing happened. I quickly
looked at the door. Had I locked it or flipped the bar when I came in?
Nope. Finally, I heard a quiet knock on the door.
"Housekeeping," a woman's voice said. I heard a keycard in the door.
< to be continued >
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