Personalising My Personal Assistant
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The Personal Ad - Part One free porn video
The Personal Ad - Part one.
By Brandi Carlsen
It all started with a personal ad on tedslist, an anonymous online
classified ad service. I figured it was worth a shot.
"Sissy Boy iso bossy woman - 24
I am a big sissy. I enjoy dressing in women's clothing and it really
turns me on to imagine a woman forcing me to be more and more feminine.
I have two problems - I don't know shit about makeup and I don't have the
bossy woman. If you want to figuratively emasculate and humiliate a man,
I am the sissy for you."
It seemed simple enough. At first, I got several responses from men who
wanted to fuck me. I wanted a woman though - I needed someone to teach
me to be feminine. I simply wasn't interested in men. Then I got the
message:
"Dear Sissy,
You may come by my house to audition for the part of my personal servant.
I will expect you to be at my door without a stitch of male clothing. I
want you in high heels and a mini-skirt. In fact, go get yourself a
dress at the Metro. I know a sales lady there who can help you out. Her
name is Missy. You will wear the dress Missy sells you to my house. In
fact, you will leave the Metro straight for my place leaving your icky
boy stuff at the store. My address is 123 Faux Mountain road. The house
is at the end of a long driveway. Be at the Metro at 11AM Saturday, and
find missy. Tell her the following words, and do it loudly: "I am a
sissy boy, and I need a slutty dress and some fuck me pumps." Your
failure to follow these instructions to the letter will demonstrate your
unworthiness to serve me.
Lola"
My heart was in my throat and my cock was half way there it was so hard.
I jerked off, coming on my own face just reading the message. This woman
was perfect. I had two days until Saturday. I wasn't sure if I'd have
the guts to go through with it. Then, while cleaning the cum off my
chest and face, it occurred to me that I had to go through with it. I
mean, how many chances would I have to play out this fantasy?
The rest of the week dragged on. I found myself thinking about saying "I
am a sissy boy" in public almost constantly. The thought both humiliated
and excited me. Luckily, I managed to not blurt the phrase out at any
meetings! I went home on Friday and found an e-mail from Lola.
"Dear Sissy,
I want you to spend the evening ridding your body of hair. You may leave
a small patch of pubes, but any other hair below your eyebrows will be
seriously punished!
Lola"
Holy shit. This was really going to happen. I guess I thought she was
just jerking my chain. I dutifully went and shaved by body bare. It
took a while, and I paid with a couple of nicks on my ankles, but I was
silky smooth. My sheets felt good that night, and I dreamed of lace,
leather and silk.
I awoke to a start - my cat attacked my foot. He did that when he was
hungry. I got up and walked into the kitchen and filled his dish. I
glanced at the clock: 10:15. I had just enough time to shower and go. I
had no time to think about it if I was to be on time. I told myself that
I could back out and not go into the store at all if necessary. When I
got to the store, I had some trouble finding parking. That's the problem
with these Seattle neighborhoods - street parking is a bitch. By the
time I was parked it was 10:58. Now or never. I got out of the car and
walked into the store.
"Hi, my name is Missy. Welcome to the Metro, how can I help you?"
I stared like a deer in the headlights. She smiled. She knew who I was.
I knew she knew. I either had to flee or plunge in. "I am a sissy boy,
and I need a slutty dress and some fuck me pumps." I mumbled.
"I'm sorry, I didn't quite get that." Still grinning. She heard every
word. She just knew no one else had. I repeated myself loud and clear.
I got some chuckles from some of the women shopping, some of the men
looked horrified and most of the clerks just smiled knowingly.
"Okay, so you are Lola's new toy. First, we need to pick you a girl's
name. Do you have one you use?" I told her I didn't. She said she'd
give me just two minutes to decide on one, then she'd let Happy Harry the
manager give me a name. The way she said it made me think I had better
come up with something. She left me to browse panties, telling me we
should start at the bottom and work up. After what seemed like 14
seconds, she said, "time's up!" Fuck. I didn't have a name, so I
blurted the first thing I could think of: "Natasha." It was the name of
the busty internet model I'd been beating to the morning before. Oh
well, at least they didn't know where the name came from.
"Okay Natasha, first things first. You will pay for your clothes. All
the makeover stuff Lola is covering. Is that alright?" When I said it
was, she went on, "You will leave here with only women's clothing, and
only what we carry." It was then that I noticed the fact that the shop
seemed to carry nothing but clothes for strippers and prostitutes. "You
will buy two dresses, one for tonight and one for tomorrow. You will buy
a nightie and two pairs of shoes." I was getting excited. "Now, you
probably noticed we carry only clubwear and fetish clothing. I will be
choosing your garments, so don't even think you're getting the most
modest things in the store. You won't. Now, come with me."
She led me into a dressing room in the back of the store. It was nice -
it even had a sink and a toilet along with lighted mirrors. "This is our
private dressing room. You will try everything on here. Don't get too
comfortable though, you are wearing one of these outfits out the door you
little slut." She was smiling. This was clearly fun for her, and I was
guessing she knew Lola pretty well. "Strip, and I'll be back with some
underwear to try.
When she got back, I was totally naked. I was also rock hard. She said,
"Take care of that, will you?"
"How do you mean?" I asked.
She then shocked me. She slapped me across the face and said, "You will
address me as Ma'am from this moment forth. If you don't show me the
proper verbal restraint, I will stuff your mouth with a cock gag and drag
you around town wearing nothing but lacy crotchless panties and a leash."
Just then, I noticed the other sales girl who came in with Missy. She
was walking out with my men's clothes. As she got to the door she said,
"say goodbye to these."
Now I had nothing to do but obey. "How should I take care of that
Ma'am?"
"That's better. I want you to jerk off, facing the mirror." I hesitated
for half a second, she raised an eyebrow menacingly. I began to comply.
"Play with that little sissy cock Natasha. Play with it fully knowing
its pleasures are meaningless to the women you are serving. You will get
this one last orgasm to bring your erection down, and you will spend the
rest of the weekend with that nasty thing hidden away." Her sultry
whispering had me squirting all over the mirror.
"That's nasty. I don't think any of us should have to clean that up.
I'll give you a choice - you can clean it with a tissue or clean it with
your tongue. If you choose the tissue, you get a butt plug for the rest
of the night. You have two seconds to decide."
"Give me the tissue!" I'd used small butt plugs before - they really hit
the prostate well. She handed me a tissue and said she'd be back in a
moment. Just when I was done wiping it up, she came in with a man next
to her. I was guessing this was Happy Harry from the shit-eating grin he
wore. He held restraints and a blindfold.
Missy spoke: "Now, we are going to tie you up a bit, just to make sure
you don't try anything foolish." Harry strapped my hands into leather
cuffs that he then attached to each other. He then snapped a leather
strap to the buckle, and threw the strap over a beam, clasping the other
end to pull me up on my toes. I was totally stretched out. Missy came
over and lifted my feet one at a time sliding on a device she called a
gaff. "It will keep the nasty bits out of sight." This is when the
blindfold came on from behind.
"Now, Natasha, I can see from your blushing and heavy breathing that this
turns you on. That's fine. Now, it is our job to push you just a little
beyond where you are comfortable." This is when I felt the wetness
pushing at my ass. "Relax, and this won't be so bad." I did as I was
told, and I could feel Harry's arm around my hip, getting leverage for
the big thrust to come. I moaned a bit. He took that as a cue, and
pushed. This was not one of those little finger width plugs. I cried
out. "I see we are already going beyond your expectations. Get used to
that feeling - you are no longer in control. We have your wallet, your
keys, your clothes. We have your life Mr. Greg Andrews. I see you are
Director of Marketing at Leader's Mortgage. How do you think they'd
react if they knew what a whore you were?" I was actually starting to
cry. "Oh, you are a little sissy. Cry all you like, we're not
stopping."
Again, she lifted my feet, this time sliding up something lacy. "We're
going to let your hands down now, but you will not try anything foolish.
If you do, we will put you out on the street with nothing but your pretty
pink panties." As the cuffs were detached from one another, I was able
to stand normally. This caused the butt-plug to shift in an
uncomfortable, but not altogether unpleasant way. "Hold still, we need
to attach your breast forms." I felt something cold and sticky smeared
on my chest. Then, two appendages were attached over my hairless chest.
I felt their weight pull. "By the way, that adhesive is a very strong
dermal bonding agent. If you want to know what the solvent is, you'll be
very very nice."
"I'm going to do everything you say - there's no need to threaten me at
this point!" I said. I then doubled over in pain as somebody punched me
in the stomach.
"Listen you little whore, if you fail to call me ma'am one more time
you'll be pulling a train on every man in this store, starting with happy
Harry."
"I'm sorry Ma'am. What can I do to make it up to you Ma'am?"
"There, Natasha - that's the attitude we want. The first thing you can
do is stand back up, and let us put your bra on." She slipped a lacy bra
over my arms and fastened it in back. She then re-bound my hands, and
Harry hoisted me back up into the tip-toe position again. Then the
blindfold was removed. I saw myself in the mirror - still clearly a man,
but now with enormous tits - at least a D cup - and pink frilly
underwear.
"Now, standing on your toes must be uncomfortable. Let's pick some
shoes. She had several boxes in front of her. She pulled out the first
pair - some pretty simple black pumps with a four inch heel.
"I like those." Perhaps I was a bit too eager.
"Oh, they don't seem to scare you at all. Let's move on." She then
produced a similar pair to the first, but with a very painful looking six
inch heel. I winced a little. "Okay, those are in the running." The
next pair was beautiful. They were pink platforms, at least seven inches
high. The heel was a pure stiletto. I gasped. "We have a winner." I
see you like the color I've chosen for you my little pink slut."
She put the shoes on me, and only at the end did I realize they had
padlocks on the straps. I wasn't getting these off without a key. She
then dangled the key in front of me, and dropped it down her bosom.
"Don't worry - I'll be at the party tonight, and I'll pass the key to
Lola."
"Ma'am, what party?"
"Your debut, of course." She then stepped out of the room for an instant
and returned with a garment bag. She slipped it off revealing a very
small, very pink, very sexy dress. It was frilly, with lace fringes at
the neck, sleeves and hem. And the hem couldn't go much beyond the ass.
The styling looked familiar, but I couldn't make it out. My hands were
removed from the beam, and the dress placed on over my head. It was
zipped into place, and there was another ominous click. "that lock works
with the same key as your shoes." Then I saw the apron. She was tying a
lacy apron around my waist. I knew now why the style looked familiar -
it was a French maid's dress, except in pink. A long blond wig followed.
Then came the petticoat. In all my cross dressing experiments, I had
never experienced anything like it. It was full and lacy, and made the
skirt stand straight out in every direction. I knew I couldn't bend over
without showing my pink panties. "Okay, honey, have a seat. You've been
a good sport so far, so I'll give you a choice to make. Either you try
to do your own makeup here, or we take you to the mall for a makeover."
"But Ma'am, I don't know anything about makeup."
"The mall it is." She then attached a choker around my neck in pink
leather. She pointed out it could have a leash attached, and she let me
see the pink rhinestone encrusted leash in her purse. "Don't make me use
it. Follow me." To my horror, she was exiting through the front of the
store. I froze for an instant, until her hand went to the purse. I then
followed, stumbling a bit in those towering stilettos. I got looks and
laughs going out the store, and into the salon at the mall. Missy handed
me over to two seventeen year old girls telling them, "Make her as slutty
as you can." If she argues, use this." She then handed them a gag with a
three way leather strap and a three inch dildo aimed to go into the
mouth.
"I'm Stacy and this is Bev. We're going to have some fun, okay?"
"Stace, we've got to do something about those eyebrows." Bev produced
some tweezers and started to pluck as Stacy held some swatches by my face
to determine the best cosmetic colors. My eyes were watering, and I
could see Bev was doing a lot of trimming.
"Girls, please don't destroy my eyebrows!" I pleaded. I had no sooner
thought it might not have been the best idea when stacy shoved the gag in
my mouth.
"Okay, so we'll do the lips last. Give her high, pointed brows Bev.
Like something from a 30's movie!" The girls giggled as they turned my
eyebrows into a display that would make Marlene Dietrich blush.
Everything they did was big, bold and pink. I was being turned into the
biggest sissy maid ever. As much as it horrified me, I was loving every
minute of it. I already knew my next orgasm would be the biggest of my
life, assuming I ever got out of this damned gaff.
After a while, the gag came out, and the girls settled on a baby pink
color for my lips. They then started in on my nails. They buffed them,
and I figured they would polish them. Instead they smeared some kind of
glue on them and attached hot pink acrylic nails that went a full half
inch beyond my finger tips. "Oh, should we have used the dissolvable
glue Stace?" They giggled, seeing me consider wearing these pink nails
for the next few weeks.
Just then, Missy came back. "Nice job girls." She handed them each a
fifty dollar bill. Come now Natasha - you have a job tonight."
"A job, ma'am?"
"Yes. You are dressed to serve, and Lola will have many guests. You
will be serving cocktails all evening, and providing other services as
requested." Oh god. What was I getting into. "don't worry, sweetie,
she won't do anything to you that you won't enjoy. If you just decide to
trust us, your life will be much more pleasant."
I thought about that for a second. I was enjoying every minute of this.
Even the idea of serving at a party sounded hot as hell to me. Guys
groping my ass, women laughing because they knew what I was. It was
exactly what I wanted, and it hadn't even occurred to me until now.
"Missy, Ma'am, you are right. I will trust you and Lola to do what's
best for me." She smiled.
"Of course, it's not too late to invite some of your co-workers to the
party. So behave!" She gave me a wink, already knowing that I planned
to behave. "Now, the fun begins!" She then snapped on the rhinestone
leash and turned and walked fast towards the exit. I was going as fast
as I could on those heels just to keep from being dragged. It was quite
a spectacle - a leather clad dominatrix leading a pink sissy maid through
a mall on a leash. I was so busy trying to keep up, I noticed the
laughing but didn't take the time to feel humiliated until we were in the
car.
It was a short drive into Sand Point to a very nice house. Missy got
out, and led me to the door on my leash. She rang the bell, and as the
door opened, I saw a hot woman in a leather skirt, white silk blouse and
pink bra showing through. "Ahh, Natasha, we meet at last. I will take
her now missy. You did excellent work."
"Thank you Mistress" missy said with a bow. Lola handed Missy a couple
of C notes and said, "A little bonus. Buy yourself something pretty."
"You will refer to me as Mistress, or Mistress Lola. Any other form of
address will be punished. You will obey me without hesitation. I know
you get off thinking about whether to obey. Trust me, you will get yours
in time and all my commands will help you in the long run. Just obey -
don't even think about it. Now, Lick my boots."
I instinctively hesitated thinking how hot it would be. Lola produced a
riding crop seemingly from nowhere and swatted my thigh. "Lick my
boots!" I was licking before the last sound left her lips. "Now, no
matter how bizarre my orders seem to you, you will obey them." I decided
it was the only way. I was horny as shit, and I'd only just gotten to
meet the dream woman. I wasn't going to screw this up.
"Now, Natasha, we're going to have some girl talk before we start
working." I wondered how much girl talk occurred while one girl was on
her knees licking the other's boots. "First, I want to know about sex -
what is it you have women do when you're in bed with them and trying to
be a man? Do you fuck them from behind? Do you shove your cock in their
throats? Do you tell them to swallow?"
"Yes, Mistress. I've done all those things." I admitted.
"Good. We know now you're a pig as a man. We'll get that out of your
system later tonight. First, we need to do something about your figure.
Let's get you a corset." She turned on her heels and started to walk to
the stairs. I stood and hurriedly followed, not wanting to be dragged by
the leash now in her hands. "Tell me, do you drink, smoke pot or do
other drugs?"
"Mistress, I do occasionally smoke pot, and once in a while I'll drop
some acid."
She whistled. "Acid, huh? What would you say if I told you I put 5
drops of LSD 25 on the back of your neck while you licked my boots?" I
was horrified. I stopped dead in my tracks until the leash yanked me
along and Lola laughed a hearty laugh. "I'm just kidding. You'll get to
appreciate my sense of humor." We then walked into a room that looked
like a princess fairy tale had exploded. Everything was pink and lacy
and frilly. It was the kind of room that most girls grew out of by age
eight. Lola leaned over, and locked my hands together again. She then
used the leash to put me in the same predicament I was in in the store.
She then undid the lock and zipper of the dress, pulling it down to the
floor with the petticoat, leaving me standing knee deep in pink frills.
She walked to the dresser and produced a pink leather corset. It was a
below the bust style, designed to create a tight hourglass figure. "What
do you have there, a 30 inch waist? We'll have that to 26 tonight. If
you wish to stay in my service, we need to get it to 22 eventually." She
started tugging on the laces, and directing me to exhale completely as
she did. By the time she was finished, I felt like I could barely
breathe. "You'll have to breathe a little faster, because you can't
breathe as deeply." I tried, and it worked.
She undid my hands and made me pull the dress and petticoats on. As she
locked the dress back on, she said, "How would you like to have that butt
plug out?" I told her I would like that. "Here's the deal," she said,
"If I take it out, you perform oral sex on me here and now." I love
eating pussy, so I quickly agreed.
She put a blindfold on me again, and gently pushed me over onto the bed.
I heard her unzip her skirt and felt her slide into bed with me. "I know
you're a little slut, and little sluts like you love to service their
betters. Now, start slowly, and use only your mouth. Work from my tits
down."
I did as I was told. Offering licks, flicks, nibbles and gentle caresses
across her abdomen. As I got past her navel, I could feel the lace of
her panties on my chin. I grasped the front of her panties with my
teeth, and she helped from the sides. As her panties slid down I was
completely flabbergasted when a big cock hit me in the face. Lola. I
should have guessed. "Don't stop you slut, you know you want it." And I
did want it. I licked the head of her cock and took it into my lips
giving a little suckle. "Oh yeah, take it in!" I followed instructions,
both verbal and physical. As she got more and more excited, she grasped
the sides of my head. "I'm going to cum in your mouth you little sissy
whore!" As the words came, so did the spunk. Lots of it. I couldn't
even get it all in my mouth - it was running down my cheek.
Just then, the doorbell rang. Lola sprung up and said "That was nice,
now get the door. My guests are arriving." She pulled my blindfold off
and said, "don't think, GO!" And I went. As I went down the stairs she
said, "By the way, if any of my guests ask, you will provide them the
service you just did for me. You will love every minute of it!" As I
opened the door, I saw Happy Harry and Missy all dressed up. Missy
reached over and wiped some come off my cheek and shoved her finger in my
mouth. "How unladylike. We'll straighten you out yet, Natasha."
This is going to be a hell of a party.
Fawn
- 25.03.2021
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