HOUSE SITTER (Complete story)
By Lisa Lovelace
~ ~ ~
Part 1
It was summer vacation, and mom was being a pain. Making me do chores
around the house, telling me to go out and find a job instead of just
sitting at home playing games, nagging me to get a haircut. I'd just
graduated from Edina High, and I figured a guy was entitled to kick
back for a while, right? I didn't have any big college plans, we
didn't have enough money for that, but I could always enroll in
community college for a couple of years and see where that left me.
I was tired of living with mom, and I knew she was even tireder of
living with me. She divorced my dad when I was young, which is why we
had a nice house but not much money. He lived out in Arizona now and
didn't help mom at all. She'd been used to a more comfortable life
than we could lead now, and she resented it. She was finicky and high-
strung, a perfect example of what they said Edina's city name stood
for: Every Day I Need Attention.
One day she opened the door of my bedroom and barged in without
knocking. "I have a job for you, Logan."
Annoyed, I paused killing aliens. "What kind of job?"
"A fulltime job outside the house," she said.
I liked the sound of outside the house. Wasn't so sure about fulltime.
"Doing what?"
"House sitting. I know a woman who needs someone to stay at her house
and feed her cat for a week while she visits her mother."
"In Edina?"
"Minneapolis. Nice house in an older neighborhood."
"What would I have to do?"
"Make sure everything's secure. Feed and play with her cat. Keep the
house immaculate. Don't break anything."
I could do that. "I'd be paid?"
"Two hundred for the week."
"I'd be staying there? What about food?"
"Two hundred will buy you a lot of pizza. She also said you were
welcome to whatever you can find in the fridge or pantry."
"Okay, I'll do it. Can I take my laptop?"
"I don't see why not. All right, I'll tell Ms. Underbust. Pack
yourself some changes of clothing and toiletries. I'll drop you off at
her house this Friday and pick you up next Friday."
~ ~ ~
Mom drove off, and I mounted the stairs to Ms. Underbust's front door.
It was a large, handsome house, probably a hundred years old, across
the street from one of the prettier of Minnesota's ten thousand lakes.
I knocked.
A handsome woman answered. She was younger than my mom, maybe in her
thirties. "Yes?"
"I'm Logan Love, ma'am. Your house sitter."
She brightened, introduced herself as Tina Underbust and invited me
in. She wasn't wearing shoes and there was a rack of them by the door,
so I took mine off before she had to ask, and was glad I'd worn socks
without holes.
Starting in the kitchen, she showed me around the house, ending in a
guest room upstairs that she said I could use while I stayed at her
house. It looked as though it had most recently been a girl's room,
though the dominant color was baby blue instead of pink. I hauled my
backpack up to the room and rejoined Ms. Underbust in the kitchen,
where she showed me how to feed the cats and take care of their
litter.
As she showed me her household routines, I couldn't help admiring her.
She wore an old-fashioned housewife's dress, black with white polka
dots, snug above the waist and very full below it. It did a good job
of showing off her breasts, waist and legs without baring anything.
She was like if my mom had a cute younger sister. I felt myself harden
in my jeans and hoped she wouldn't notice. She probably wouldn't, as I
was not particularly well endowed.
A horn beeped outside. "Oh, there's my ride," she said. She put on her
coat and picked up her purse and suitcase. "Thank you, Logan! Text me
pictures of my kitty! See you in a week!" Her heels clattered on the
steps and faded.
She'd told me she didn't expect any deliveries or visitors while she
was gone. As far as I knew, I was on my own for the next week. Alone
with little to do.
In the house of a well-dressed woman.
A woman who appeared to be just my size.
Temptation.
I'd always been attracted to women's clothing. I couldn't help it, I
was born this way. I never had a chance to dress up at home because
mom wore plus sizes, and my short, slight figure would be lost in her
things. I wanted to check out Ms. Underbust's closet. As long as I
looked but didn't touch, she'd never know, and as long as she never
knew, there would be no harm done.
I explored her closet and chest of drawers. Looked but didn't touch.
The closet contained office wear - businesslike dresses and skirt
suits, no trousers - and softer dresses for at home or special
occasions. The latter included what almost looked like dance costumes:
three knee-length swing dresses with snug bodices and full skirts,
accompanied by white, pink and black crinoline petticoats. Perfect for
old-time dancing, a side of Ms. Underbust that I hadn't known about.
Temptation.
I looked at the nightgowns hanging from a set of hooks: ankle and
waltz- length gowns and robes and a pink baby doll. An ankle-length
baby blue nylon nightgown caught my eye. Its shirred bodice was
decorated with lace and ribbons, and it had delicate flutter sleeves.
If I was going to give in to temptation and wear a nightgown to bed,
it would be the one I'd choose.
But I wouldn't! I wouldn't touch the clothes. Just look. Don't touch.
The chest of drawers held a pretty collection of lingerie: panties,
bras, slips, camisoles, hosiery, garter belts and a variety of
foundation garments, also in white, black and pink. Nice things,
nothing sleazy.
Temptation.
I resisted. Played games on my laptop. Ordered a pizza and ate it
while watching her sixty-inch TV. Took a shower, put on the t-shirt
and boxers I'd packed instead of pajamas, and climbed into bed in the
guest room.
Woke up in the middle of the night. Could not stop thinking about the
nightgown. My boxers and t-shirt felt rough and uncomfortable. I
climbed out of bed, took off my boy clothes, fetched the nightgown
from the closet and let it slide down my body. I would wear only
clothes that could go through the washer and dryer, and would launder
them and put them back in place next Thursday. She would never notice.
Having succumbed to temptation, I slept comfortably for the rest of
the night.
Saturday morning, I got up and puttered around in the nightgown for a
while. I found some English muffins and had them toasted with butter
and blueberry jam. The coffee machine looked dangerously complex, so I
found a teakettle and made some tea.
What would I do for the day? I tried to deny that I already knew, but
it was useless. I had Ms. Underbust's entire wardrobe to play with, at
least anything washable.
In for a penny, in for a pound. I selected panties, a bra, garter belt
and stockings, a slip, a petticoat, and one of her dance dresses,
carefully noting where each item was and how it was folded or hung.
Sitting in Ms. Underbust's bedroom, I put on her clothes. The dress
had a white collar, a fitted bodice and a full skirt in an aqua and
teal floral cotton print. Under it I wore the white petticoat. I had
small feet for a man, and was able to slide into a pair of white
sandals with a two-inch heel. For the first time in my life, I was
dressed as a woman from the skin out.
Oh, I was far from a finished product. I had to do something with my
hair. I needed makeup. I had no jewelry. But looking at myself in the
mirror, I saw a reasonably attractive young person who looked more
female than male. In fact, she was rather cute. She was also stiff as
a board.
I practiced moving in the clothes, walking in the heels, feeling the
dress and petticoat swish around my hips. I watched some YouTube
videos on how to walk like a woman, and tried to place shorter steps
on a straight line, which felt totally unnatural. I crossed my legs or
kept my knees closed when I sat. I drew my arms in close to my body,
let my wrists go limp but not too much so. I practiced a curtsy, and
liked the sight so much that I did ten of them.
Wow! If I only had a dance partner! (And knew how to dance, which I
didn't.) Even so, I was wearing a sexy dance dress and all the
feminine underpinnings, and I loved the feel of them.
I spent the rest of the morning playing with my hair and experimenting
with makeup. I tried parting my hair in the middle and tying it into
pigtails with ribbons from a drawer of her vanity. It looked pervily
juvenile, but no one could see it but me, and I have to admit it
turned me on. Alas, Ms. Underbust didn't have a schoolgirl's uniform
or little girl's dress in her closet.
After an hour or so of creating makeup disasters and destroying the
evidence, I decided to settle for eye liner, eye shadow, blush and
lipstick, no mascara, and managed to achieve an acceptable result by
using less than half as much makeup as before. Ooh! It worked. I was
more than cute, I was pretty. It was an unnerving feeling. I was a
boy. I wasn't supposed to be pretty.
I had a light lunch of Greek salad with feta that I found in the
refrigerator. Afterwards, I cleaned up the kitchen, tidied up all the
rooms downstairs, emptied the trash and cleaned all the sinks and
counters in the house. I decided to save the vacuum cleaner for
tomorrow, and the mop for later. The house already looked better than
Ms. Underbust had left it. I wanted to please Ms. Underbust.
I spent the late afternoon streaming the movie of Emma, the Jane
Austen novel, and fell in love with Anya Taylor-Joy's Regency gowns. I
decided to watch it again tomorrow.
As dusk fell outside, did I think what I could make for dinner with
the ingredients on hand? I did not. I called the same pizzeria and
ordered a large pepperoni. Only after I hung up the phone did I
realize that I would have to deal with the delivery person en femme.
My heart almost stopped.
I rushed to the mirror to see what was most wrong about my image. It
was the pigtails. They made me look like an idiotic infant. I untied
the ribbons and hurriedly brushed my hair into a center part. It
looked better. Not great, but better. My makeup was okay. Damn! I
forgot nail polish. Nothing I could do about it now.
The delivery boy showed up in fifteen minutes, which I spent terrified
that he would read me as male. Finally, a knock on the door.
The delivery boy looked me up and down. "One large pepperoni pizza,
Miss," he said.
I loved him for calling me Miss. I'd paid online using a credit card
mom lent me, but gave him a five-dollar tip in cash.
I devoured three-quarters of the pizza, saving the rest for breakfast.
Oh! Life could be good here. Pizza for dinner and breakfast, something
from their larder for lunch, and then pizza again for dinner... but
pizza was messy... I'd have to be very careful not to get it on
whatever I might be wearing. Maybe I should order something tidier
than pizza...
The week passed with me blissfully dressed in lovely women's wear
during the day and a nightgown at night. I think I tried on every
dress in her closet, except one or two that were so tailored that I
was afraid of stretching them out. Ms. Underbust seemed to have a
thing for vintage designs, and I, too, found them attractive.
Thursday morning, I got fully dressed up in the morning and then
realized I hadn't brought in the mail yesterday. I didn't want to
change clothes and clean off my makeup, so... what if I just ducked
out the front door, sashayed down to the mailbox on the street,
grabbed its contents and sashayed back inside? Most folks on the
street had probably already left for work, so it was unlikely anyone
would see me. The thought of going outside en femme scared me, but I
had to be brave. I opened the door and walked down to the mailbox, my
heels clicking on the pavement.
As I scooped the mail out of the box, a black Lexus with tinted
windows pulled into the driveway, right next to me. A man sat at the
wheel. He rolled down his window. "Hi, I'm Dirk, who are you?"
I gulped, stood up straight, picked a girl's name out of thin air and
said softly, "I'm, uh, Lisa. Who are you?"
"I'm Tina's boyfriend." Oh my God. A complication I didn't need. "Is
she home?"
"Not yet. Tomorrow," I said.
"And you're staying here? You're...?"
"Oh, I, I live down the street, my mom knows her. I'm house sitting
for her."
"Yeah, she was visiting her mom," he said.
"Yes," I said. "Well, nice to meet you." I was desperate to get inside
the house and close the door. I should have changed my clothes. I
should have changed my clothes. I should have changed my clothes! Any
moment now, he's going to say, hey, wait a minute, are you...?
But he didn't. Instead, he got out of his car. He was easily six foot
two, a couple of hundred rather muscular pounds. "Hey, Lisa, I'm
really thirsty. Can I come inside and get a glass of water or
something?"
Christ, no. He thinks I'm a girl, I'll be alone with him, totally
vulnerable in my skirts and heels. "Uh..."
"I'll be quick," he said.
I sighed. "Come on in."
I felt his eyes on my ass as he followed me into the kitchen. I got
out a glass, filled it at the tap, handed it to him and retreated to
the other side of the kitchen island. He raised the glass in an ironic
toast. "Looking good, Lisa," he said.
He set down the glass and circled the island, backing me into a
corner. I got really nervous. He put his hand on my shoulder. I
brushed it off. He raised it back to my shoulder. I tried to brush him
off again, but he caught my wrist in his other hand, and in a moment,
I was helpless, unable to get free of him.
"Stop it! Let me go!"
He ignored my protest. "You're so pretty." He kissed me on the lips.
"No! No!" I was nowhere near as strong as him, but testosterone made
me a bit stronger than most girls, and I was able to twist out of his
grip. I put the kitchen island between us again.
"Stop, or I'll..." Or what? He could easily overpower me. "I'll tell
Ms. Underbust!"
That stopped him. "Aw, sorry, Lisa, I was just fooling around. I
wasn't going to do anything. Just one little kiss. No need to mention
it to Tina."
"Okay, okay!" I said. "Just keep your hands off. You can go now."
He retreated from the house, got back in his car, drove away. I
watched him zoom down the street and hurried back inside, where I
broke down in tears. I consoled myself with the thought that at least
he hadn't detected my real sex.
I spent the evening laundering all of Ms. Underbust's things that I'd
worn, hand-laundering the most delicate items, and putting them away
exactly as I'd found them. I even ironed the slip I'd worn.
I was back in my boy's clothes when Ms. Underbust returned Friday
morning. She gave me a strange look.
"I was texting with Dirk," she said, "and he mentioned that Lisa from
down the street was house sitting while I was away."
Oh shit oh shit oh shit. Oh oh oh shit.
"The thing is," Ms. Underbust said, "I don't know any Lisa from down
the street. Did you have a girl named Lisa staying here?"
"No, ma'am," I said.
She looked me in the eyes. "Well, then, who's Lisa?"
I looked down. Could not speak.
Her eyes widened. "Was it you? Were you wearing my clothes... Lisa?"
I couldn't stand the guilt, broke down in tears and confessed all.
She was angry at first. She felt violated, and I couldn't blame her.
She made me show her which panties and bras I'd worn. She took them
out of the drawer and tossed them on the bed, telling me they were
mine now, she'd never wear them again. She asked which dresses I'd
worn. I lied, not wanting to admit I'd tried on most of them, and
pointed to just one dress, the aqua and mint floral dance dress.
"That's the only one you wore? Really?" She cocked an eye at me.
"It was the first one I tried," I said, which was true. "It fit so
nicely that I didn't bother with any of the others." Which was not
true.
"Well, it's yours now. The next time you want to dress up, come on
over." She laughed, the last thing I expected at the moment. "Why not?
Before I let you go home, Logan, I want to see you all dressed up as
Lisa. What else did you wear with the dress? A slip? A petticoat? It's
a swing skirt, it needs a petticoat. Here." She pulled the white nylon
petticoat out of the closet and tossed it on the bed along with the
other lingerie.
"Okay, put on your pretty new underwear," she said. "Then I'll do your
makeup, and then you can put on the dress."
"I'm not going to put this stuff on!"
"Why not? You did it when I wasn't here. Dirk said you looked lovely.
Shall I invite your mother over for a fashion show?"
"No!"
"Well then, get dressed."
"What, in here?" I said.
"Why not? Real girls don't mind getting dressed around other girls."
With a show of reluctance, I stripped off my boy's clothes and put on
the stuff she'd tossed on the bed. The panties first, to cover my boy
bits, and then the bra. She stuffed the cups with pantyhose from her
hosiery drawer.
"You should really wear a slip under the dress," she said. She pulled
one out of another drawer. "Here, take this one, it's old and just
slightly large on me. It's yours." She slid it down over my
upstretched arms. "And now the petticoat." She held it open and I
stepped into it. She pulled up the elastic waistband and stood back to
examine me.
"Oh, just look at you! Lovely Lisa, all dressed up in her pretties. No
stockings for you until you shave your legs. Do any of my shoes fit
you?"
I pointed to the pair of sandals I'd been able to squeeze my feet
into.
"Come, sit." She patted the padded seat of her vanity stool. I sat,
and she strapped my feet into the sandals. "I'll do your makeup."
I was tempted to refuse, but realized that without her help, I would
look even more ridiculous. I sat. In ten minutes, she made me look
gorgeous. She picked up a hairbrush and hair dryer and fussed with my
collar-length hair until it looked passably feminine.
"Wow, you clean up nicely," she said.
"Look, Ms. Underbust, I'm really sorry I touched your things, but can
we stop now?"
"No!" she said. "You didn't just touch my things, you put them on! If
you like them so much, you can wear them for the rest of the day.
Besides, I want to get to know Lisa better. Let's get your dress on.
Hands up!"
She tugged it down over my body and zipped it up the back. The bodice
hugged me tightly and the skirt draped prettily over the petticoat.
She had me swing my hips and swish my skirts around my knees. It felt
wonderful, so right. I was thankful for the petticoat not just because
it made me feel girly, but also because it hid the protuberance in my
panties.
She grinned. "Oh, you're so cute! Hang on." She disappeared for a
minute and returned with a pretty little lace-trimmed hostess apron.
She tied it around my waist, straightened the bow and adjusted my
dress, and then stepped back, whipped her phone out of her purse and
started taking pictures.
"Hey! Stop that!" I said, trying to grab her phone.
She shoved it back into her purse. "Too late! Now I have video! Pretty
little Lisa, all dolled up and ready to do her housework! Or... maybe
she's not a housewife, maybe she's a maid! All she needs is a black
dress and a pretty cap. Which would you rather be, Lisa? A housewife
or a maid?"
"Neither," I said, wishing I could be either or both. I had mixed
feelings about being a female servant, but I definitely liked the idea
of dressing like one. I was such a disgrace to my sex.
"Sorry, that's not an option," Ms. Underbust said. "Does your mother
know you like to dress up?"
"No," I said. What an idiot I was. Too late, I saw I'd totally set
myself up for blackmail. I should have told her that yeah, my mom
knows and she's cool with it. But if I'd said that, Ms. Underbust
might mention it to her casually, just to check... I was trapped
either way.
"Why not?" she said. "Don't you think your mother should know her son
likes to dress like a pretty housewife?"
"No! Please don't tell her!"
Ms. Underbust smiled. "Well, Lisa, maybe we can work out a deal here.
The house looks fabulous. You obviously have good housekeeping skills.
I'd love to have a live-in maid. Your mother said you're looking for a
job. Okay, you're hired."
"I don't want to be a maid, Ms. Underbust!"
She got her cellphone out of her purse. "Let's see... 952-555-0123,
right?"
"Please don't call her! I'll... I'll..."
She stabbed a finger at me. "You'll what? Accept my job offer? Minimum
wage for forty hours a week, no overtime, though you'll be on call
24/7. Room and board and a clothing allowance. Well, not so much an
allowance, I'll just give you lots of pretty clothes, starting with
the outfit you're wearing now."
"I can't be a maid, Ms. Underbust! That's a girl's job!"
"I don't see the problem," she said. "You look like a girl to me.
Girls can do boys' jobs, you know, and boys can do girls' jobs. I
don't care what you have in your panties, as long as you keep it
hidden."
"What about your boyfriend Dirk? Won't he mind?"
"Why should he? He's already met you and he thinks you're a cute
chick. Just don't give him any reason to think otherwise - he doesn't
like it when people deceive him."
"He kissed me when I told him not to!"
"That doesn't sound like Dirk. You must have flirted with him."
I gulped. How could I get out of this situation?
"Look, Lisa, here's what I'll do," Ms. Underbust said. "I'll call your
mother. I won't tell her you're going to be my transvestite maid...
oh, this will be so much fun! Instead, I'll tell her that you did such
a great job as a house sitter that I've offered you a fulltime job
as... hmm... a marketing events assistant. Ha! A booth babe. Your new
job's in downtown Minneapolis, so to save commute time, my company
will put you up in an apartment it happens to own there, at no cost to
you."
"I'll be living downtown?"
"No, no, silly, you'll be living here with me. The downtown apartment
is just a story we'll tell your mother. Be sure you tell her the same
story. So, do you accept the job?"
"As a marketing events assistant?"
She rolled her eyes. "No! As a maid. If you want, you can think of it
as a very personal assistant... to me. You'll do your assisting here
at home, wearing a pretty maid's uniform fluffed out with petticoats
and an apron and stockings and garters and a maid's cap. Oh, yes! How
does that sound, Lisa? You had fun while I was away, didn't you? You
liked wearing my clothes, didn't you? Well, now you'll get to wear
even prettier and sexier outfits! And the best thing is, I won't tell
your mother what a bad girl you were while I was away. Oh, and I won't
tell Dirk that you're a boy. That's my job offer. Do you accept?"
She had me trapped six ways from next Tuesday. I had no choice. "Yes,
Ms. Underbust."
"Yes, what?"
"Yes, I accept the job." I felt a strange mix of embarrassment, fear
and pleasure, and was surprised to feel myself stiffening.
"Call me ma'am."
Did she have to rub it in? "Yes, ma'am, I accept the job."
"Good! Now curtsy."
"What?"
"Don't you know how to curtsy, Lisa?"
"Of course not!" I lied. I'd been practicing curtsies every day for a
week, though certainly not with any intention of doing them for Ms.
Underbust. "I'm not a girl!"
"No, not yet, but you're my maid, and I want my maid to dress and
behave like other maids. And maids curtsy whenever they enter or leave
their mistress' presence, and when their mistress gives them
instructions."
Okay, I'd show her. I placed my right foot behind my left, grasped my
dress and petticoat with my thumb and forefinger, splayed out my other
fingers, lifted my skirts, lowered my eyes and bent my knees. It was
an intensely humiliating gesture of subservience. I held the curtsy
for a second, then straightened up and let my skirts fall.
"Very good, Lisa. You'll be a natural as a maid."
"Yes, ma'am." This was getting worse and worse. What should I do? What
could I do? I didn't want to go home, certainly not dressed like this,
and if I just ran out the door, I'd have some tricky explaining to do
to whoever picked me up - the police or, if I was unlucky, someone who
might want to misuse me.
"Now then, Lisa, if you're to be my maid, you'll need uniforms and
lots of other things. You and I are going to go shopping! I'll see if
my salon can fit you in for an emergency makeover to make you look
more like a girl, and then you can make your public debut as Lisa."
"Oh, please, no! I can't go out in public dressed like this! Can't we
just order clothes online?"
"Oh, Lisa, I think you know enough about women's clothes to understand
that the sizes are imaginary. You have to try things on to see if they
fit. We are going out. You're working for me now, and I expect you to
do as I say."
In no time we were in her car on the way to the mall. I was so scared
that I almost broke down again, but once we got there, I soon found
that no one paid me any particular attention. I guess my outfit wasn't
short or tight enough to attract the male gaze. One woman told me she
liked my dress. I nervously thanked her and, as girls do, complimented
her in return - on her necklace, I think.
Ms. Underbust talked her salon into giving me an instant makeover,
which relieved my concerns about my hair and makeup, and then the two
of us did our bit to keep department stores in business by spending a
shameful amount of her money on girly stuff for me. Panties, bras,
slips, a tight girdle with removable garters, a garter belt and
stockings, nightwear, shoes, cosmetics, a handbag and other
accessories. I had my ears pierced with tiny heart-shaped gold studs,
and got some modest gold hoops for when my ears healed and a tiny gold
crucifix on a light chain around my neck.
No dresses or separates, though. For those, we made a separate stop at
a uniform store, where Ms. Underbust picked out three maid's uniforms
and accessories for me.
The dresses were tasteful as maid's uniforms go - not silly French
maid's costumes, but tea-length black cotton frocks with fitted
bodices, full skirts, long sleeves and white collars and cuffs. She
also bought me a set of petticoats of varying fullness, all the same
length as the dresses, and half a dozen aprons, some with bibs and
ruffled straps and some waist aprons. Two ruffled maid's caps trimmed
with lace.
As for separates? Nada. No skirts, blouses or, God forbid, trousers.
Only dresses. "I think we've covered your basic needs," Ms. Underbust
said.
We checked out, and I had to make my way back to the car carrying an
embarrassing number of shopping bags that nearly filled the trunk. I
marveled at the sheer amount of stuff I now needed as a girl, compared
to what I'd needed as a boy. Of course, the maid's uniforms were
fairly over the top in terms of female needs. I mean, who wore
petticoats nowadays?
Ms. Underbust let me listen in as she called my mother and told her
about my new job in Minneapolis.
Mom was delighted to hear the news. "So he'll be moving out at last?"
she said. "With a fulltime job? Wonderful! What will he be doing in -
marketing, was it?"
"Marketing events assistant. I expect he'll handle the job
beautifully," Ms. Underbust said. "He's in the next office, would you
like to talk to him?"
"I suppose so," my mother said. Ms. Underbust waited a minute and then
handed me the phone.
I understood immediately that this was a test. I could ask my mom for
help and tell her to call the police because Ms. Underbust was making
me wear a dress and be her servant. Or I could tell her the same story
that Ms. Underbust did.
I realized that if I asked for help, the best possible outcome would
send me home to my mom in boys' clothes, and that wasn't the outcome I
wanted. Mom was right. Time for me to move out and make my own way in
the world. Even if my first job required me to dress as a maid.
Mom wished me luck, and then Ms. Underbust took the phone and said I
would stay with her tonight and she would bring me home tomorrow
morning to pack whatever I wanted to take to my new apartment.
Anything I left behind could be thrown away. Mom asked for my new
address, and Ms. Underbust gave her a post office box number that she
said was the apartment building. I learned later that it was actually
Ms. Underbust's post office box.
Twenty-four hours later, I'd moved into Ms. Underbust's fancy house
with a view of the lake. She showed me what she wanted me to do, and I
developed a weekly routine to get it all done. Cooking, cleaning up,
doing the dishes, doing the laundry, dusting, vacuuming, changing
linens, cleaning toilets, separating trash and recycling into the bins
in the garage that the gardener took out to the curb every week.
I did all the woman's work that a traditional housewife was expected
to do... minus children, thank goodness. I imagined having to take
care of a baby, nursing it, changing its diapers, dressing it, playing
with it, carrying it around with me, getting up at night when it
cried, all on top of the housework I did as a maid. Ugh!
I spent my days in my maid's uniforms, with a petticoat under my dress
and an apron over it, and got used to the feeling of hems swirling
around the tops of my calves. Ms. Underbust and I got along more
smoothly than my mom and I ever did, and I came to realize that even
though I was just a maid, my life was better than it had been at home,
and I was happier as a result.
~ ~ ~
Then, one morning, Dirk dropped by.
It was the first time in a while. He'd been out of town on whatever
his business was, and wanted to see his girlfriend.
The doorbell rang. I went to answer it, wiping my wet hands on my
apron. I checked myself in the mirror in the entry, fluffed my apron,
straightened my cap and opened the door.
There he was, all six foot two of him. I caught my breath.
"Hi, is Tina here? Hey - wait a minute, aren't you Lisa?"
I wanted to sink through the floor. "Yes, I'm Lisa. I work for Ms.
Underbust now. She's not here at the moment, but she'll be back soon."
"Wow, you look great! How do you like being a maid?"
"It's a job," I said. "Can't complain about the commute - upstairs to
downstairs."
"Wish I could do that. Hey, could I have a beer?"
It struck me as rather early for a beer, but I wasn't going to say no
to Ms. Underbust's boyfriend, not unless he misbehaved again. "Yes.
Please come in." I closed the door and went to the kitchen. He
followed me, ogling my ass, and took a seat at the breakfast table. I
served him a beer and remained standing, feet together and hands
folded over my apron.
He took a deep swig. "Thanks, Lisa. You know, you look a lot prettier
now than the first time I saw you."
I didn't want his compliments. "Just remember to keep your hands to
yourself."
"That outfit you're wearing is really cute."
"It could be worse. At least it's not halfway up my thighs."
"Wow, that would be awesome," he said. "Show me."
"Show you what?" My nervous meter ticked upwards.
"Halfway up your thighs. Just lift your dress. And whatever you've got
on under it."
"No, thank you."
"Aw, c'mon, Lisa. I'm paying you a compliment. Hey, if you're Tina's
maid, shouldn't you do what her guests tell you to do?"
I sighed, plucked at my skirts and lifted them in front until they
were almost but not quite halfway up my thighs. He could see the
garters holding up my stockings. I felt so humiliated! Dirk eyed my
legs and smiled. It was a weird and uncomfortable feeling, being
checked out by a man.
I dropped my skirts. "Hope you enjoyed the view."
Dirk grinned. "Oh, I did. Come sit here." He slapped his left thigh.
"No, thank you," I said.
"I said come here, Lisa. Take a seat." He stopped grinning.
"No. You can look all you like, but you can't touch."
He stood, grabbed my arm and pulled me face down over his thighs. His
free hand pulled up my skirts and yanked down my panties.
"Stop!" I cried. "Let me up! Help!"
"Lisa! Hush! Disobeying your superiors is a spanking offense." Before
I could reply, he gave me a sharp, stinging swat. "Count them, Lisa."
"No!"
"I won't stop until you do," he said. The next spank landed.
"Ow! One," I said.
"Thank me after each one," he said.
Another. I grimaced. "Two, thank you."
"Lisa! Call me sir."
Another. Ouch! "Three, thank you, sir."
When I reached twenty, he stopped. My bottom was on fire. I was
crying. I had eyeliner dripping down my cheeks. I probably looked like
Zombie Maid. And - dammit! - I was stiff again. I didn't think he
could feel me through the petticoats, dress and apron, but I was
ashamed to react this way to being spanked.
"Are you going to obey me now, Lisa?" he said.
I didn't want to say yes. "What do you want me to do?"
"I want you to sit on my lap, Lisa."
"No, sir! I don't want you to touch me! You can't spank me! Let me
up!"
The front door opened and shut. Ms. Underbust walked straight into the
kitchen and stopped short, taking in the tableau Dirk and I presented.
I lay across his thighs in my maid's uniform, my face a mess, with my
skirts pulled up over my back, my panties pulled down and my bottom
bright pink. Dirk easily held me immobile with his left hand and was
ready to swat me again.
"What's all this?" Ms. Underbust asked.
Dirk let me go. I quickly regained my feet, letting my skirts fall and
pulling up my panties as I backed out of his reach.
"Hi, Tina," Dirk said. "I had to discipline your new maid."
Ms. Underbust frowned. "What for?"
"Disobedience," Dirk said.
"Disobedience is certainly very bad," she said. "How did she disobey
you?"
"I asked her to sit down, and she refused," Dirk said.
"He wanted me to sit on his lap!" I said.
"Hush, Lisa," Ms. Underbust said. "Did you ask her to sit on your lap,
Dirk?"
"Yes, I did," he said.
"Politely?"
"I didn't touch her until she refused."
Ms. Underbust nodded. "Why wouldn't you sit on his lap, Lisa?"
"I didn't want him to touch me, ma'am. He was ogling me and making me
uncomfortable. He made me lift my skirts and expose my thighs."
"How did he make you lift your skirts?"
"He told me to."
"He didn't force you? He didn't touch you until you refused?"
"No, ma'am. But -"
"That's enough, Lisa. Dirk is my guest - you should call him Mr.
Steele. You should obey orders from my guests as long as they do no
harm, and it wouldn't have harmed you to sit on his lap. You should be
happy that he wants you to sit on his lap! If you thought his order
was improper, you could have come to me afterwards and explained your
concern, and if I thought your concern was justified, I would have
discussed it with Mr. Steele. You should not have disobeyed him on
your own. You're the maid, not the mistress."
This was so unfair! I blinked back tears.
"On the other hand," my mistress said, "I'm partly to blame. I didn't
give you detailed instructions on how to behave to Mr. Steele. But
it's mostly your fault."
How could it be my fault that Mr. Steele kissed me and beat me? She
didn't give me time to protest.
"So, Lisa, I want you to face Mr. Steele. Curtsy, kneel before him,
apologize very humbly for disobeying him, and promise never to do it
again. If he accepts your apology, you may rise, thank him humbly and
curtsy to him again. As you'll see, Dirk, Lisa makes a very pretty
little curtsy."
I wanted to slap Mr. Steele, but instead I obediently went through the
humiliating little ritual of apology. "Mr. Steele, sir, I humbly
apologize for disobeying you and I promise never to do it again." I
curtsied. Damn! I was getting hard again.
Dirk was grinning ear to ear. "Good girl, Lisa. I accept your apology.
Now, come over and sit right here." He patted his thighs.
I felt defeated. Ms. Underbust wouldn't defend me. "Yes, sir." I
scooped my skirts under me to protect my bottom before settling myself
on his muscular thighs. I felt something stiff trying to poke through
his pants and my petticoats, right between my buttocks. I shifted in
his lap, but that just made him stiffer.
Ms. Underbust said she was going to tell me something important and I
should listen carefully.
I was having trouble concentrating, because Mr. Steele was very gently
starting to hump my butt. Slowly at first, gradually speeding up,
giving me feelings I'd never had before.
Ms. Underbust was explaining that she and Mr. Steele were in love and
would be getting married.
To my surprise, I found myself responding to his pressure. It made me
want to wriggle in his lap, make him press against me harder.
Ms. Underbust said that when they got married, she wanted me to be one
of her bridesmaids. She said I would just love the dress she'd picked
out. It was pink, she said.
My wiggling seemed to stimulate Mr. Steele. He positioned me at the
spot on his lap where he could poke me more directly.
Ms. Underbust said Dirk was going to move into her house and would
share the master bedroom with her. I would sleep in the guest room,
which she would redecorate as the maid's room.
I began to writhe in Mr. Steele's lap. He was fully hard. I could feel
him press against my rear entrance, outside an emptiness that somehow
ached to be filled.
Ms. Underbust said that as the household maid, I would serve and obey
both of them, not just her. Just as she was my mistress, Mr. Steele
was my master, and I was to call him that.
Mr. Steele's rhythmic pulses were making me feel feminine, receptive,
yielding... a sexy little maid in the hands of her big, strong master.
Ms. Underbust said Dirk would expect me to provide personal services
that she herself did not care to provide. He would be in charge of my
punishments. He would...
Dirk's hand stole under my skirts and tugged on my skimpy panties. I
dutifully lifted my butt. He pulled them down my legs. I kicked them
off.
What Ms. Underbust was saying sounded really important, but I could no
longer follow her words. I was lost in lust.
"Oh, Liiiiisa," Dirk said.
Breathing hard. Wriggling. Grinding. Feeling frantic. "Yes, master?"
"Unzip me," he said.
~ ~ ~
Part 2
My petticoats rustled under my maid's uniform as I knelt before my new
master and unzipped his trousers.
"Well?" said Dirk. "Take it out."
I groped in his pants and awkwardly pulled out his male equipment.
"Well?" Dirk said. "C'mon, Lisa. Lick it. Kiss it. Suck it."
I shot a glance at his girlfriend, Tina - Ms. Underbust to me. She
nodded.
My name was Lisa now, but I used to be a boy named Logan. Ms.
Underbust hired me as a house sitter while she was out of town, and
found out afterwards that I'd been wearing her clothing. She made me
dress up for her, said I was too pretty to be a boy, renamed me and
blackmailed me into becoming her maid. I'd been serving her for three
weeks now.
Oh, I could easily walk out the door and be free - but for how long? I
had no money or identification, and I'd be wearing a maid's uniform,
unless I stole one of Ms. Underbust's dresses. I wondered how far I'd
get before getting picked up - either by the cops, or by a male
predator prowling the streets in search of lost souls like me.
I could always return to my mom's house in Edina. It was only a few
miles outside of Minneapolis - I could walk there, though it'd be an
agonizing trek in my heels. But Mom didn't want me around now that I'd
finished high school, and she didn't know I liked girls' clothes... so
I could just guess how she would react if Ms. Underbust dropped me off
at home in one of my maid's uniforms. It would not be good. Mom would
probably tell me to get right back in that car and beg Ms. Underbust
to keep me.
So I didn't even try to escape from Ms. Underbust's house. I wasn't a
man. I was a coward, a wimp, a sissy.
Which is why I was now on my knees in front of Dirk, or Mr. Steele, as
I'd been told to call him. He clearly expected me to give him a
blowjob. I'd never received one, and for sure had never given one
before. Ms. Underbust's sardonic smile told me she was amused by my
situation. I couldn't expect her to rescue me.
I grasped the base of his cock, which was several inches longer than
mine, and tentatively licked the tip. It was warm.
"Kiss it, Lisa," Ms. Underbust said.
I did, and saw that I'd left a lipstick print on the head of his tool.
My tiny sissy revenge on the big strong man.
"Suck it, girl," Mr. Steele said.
I did. I sucked it and licked it and kissed it and rubbed my hand up
and down its saliva-coated length, and in a few minutes I was
rewarded, if that's the right word, with a load of his ejaculate in my
mouth. I swallowed the gooey mess, licked him clean and tucked him
back into his tighty whities. I was painfully erect myself, but the
bulge was hidden in my panties and petticoats.
"Thank you, Lisa," Ms. Underbust said. I knew she didn't like giving
Dirk blowjobs. That was my job now. "Well done."
Mr. Steele patted me on the head, as if I were his little pet. "Get me
another beer, Lisa," he said.
~ ~ ~
Later, I pulled Ms. Underbust aside and told her I wanted to quit my
job.
"Don't be ridiculous," she said. "It's hardly unusual for a girl to
give a guy a blowjob. I was surprised you hadn't before."
"I'm not a girl, ma'am!"
She sighed. "Must we go through this again, Lisa? Look at yourself.
Absolutely everything about you screams girl. You're a sissy, a girl
for all practical purposes. Even if you were a boy, it's not unusual
for one boy to give another boy a blowjob."
"But I'm not gay, ma'am!"
"It's not gay for a sissy to give a boy a blowjob. Sissies aren't gay
or straight. They're sissies."
Argh! I wasn't getting anywhere with her. I now understood what she
meant when she'd told me my job would include giving Mr. Steele
"personal services" that she didn't want to give him. I could only
hope he wouldn't want this particular service very often.
I lived in fear that Mr. Steele would find out I wasn't the teenage
girl I appeared to be. Ms. Underbust had told me he didn't like being
deceived, and my life now was one long deception. I asked her what I
could do, and she ordered me a gaff, something like a thong panty that
helped minimize male parts. She also advised me to avoid being alone
with him and to threaten to tell her if he tried to go beyond the
occasional blowjob.
"You can't handle him, but I can," she said.
I wasn't terribly reassured. I started wearing my gaff under my
panties and an extra petticoat under my uniform, so as to conceal my
secret under more rustling layers of fabric.
My attempt to dress more securely went out the window one day when, as
I was serving mojitos to my master and mistress on their back deck,
Mr. Steele gave me a large wrapped package with a note: "For Maid
Lisa, from her Master."
"Open it," he said.
I unfolded white tissue paper to reveal a black satin dress trimmed in
white lace. Oh, God. It was a stereotypical French maid's costume. It
looked well-made, not Halloween junk. Its skirt was extremely full and
extremely short. I held it up against me and wondered if it would even
cover my panties. Wearing it would be an exercise in humiliation.
"Thank you, Mr. Steele," I said.
Inside the box I also found a short, rustling taffeta petticoat half
an inch longer than the skirt, a lace-trimmed satin apron that was
pretty if not practical, and a pair of black satin panties with rows
of ruffled white lace sewn onto the seat.
My heart sank as I inspected the costume. It was fetish wear. I
wondered how often my master would expect me to wear this instead of
my regular uniform, whose skirts brushed the tops of my calves.
"Put it on," he said.
Oh God. I would look indecent. I picked up the costume pieces and
started to leave the room.
"No," Mr. Steele said. "Change here."
I wanted to disobey him, but knew too well what would happen if I did.
My bottom was still sore from my last spanking. I untied my apron,
took off my regular dress and put on the French maid's dress. It
weighed half of what my uniform dress did. I took off my regular
petticoats, which preserved my modesty, and put on the new one, which
did not - it just made my skirt stick out farther and cover less of my
legs. I reached under the skirt and slid down my old panties, leaving
the gaff in place, and pulled on the new panties. I used both hands to
smooth the lace ruffles covering my bottom.
I tugged on the new dress to try it make it longer, but it didn't
help. It was scandalously short. If I bent over even slightly, anyone
could see my panties. The white lace was impossible to miss.
Ms. Underbust tied the delicate apron tightly around my waist, stood
back and looked me over.
"What do you think, Tina?" Mr. Steele asked.
My mistress reached over and pulled off my mob cap. "Lose the cap,"
she said. "All she needs is a frilly hairband that she can make
herself. It'll teach her how to sew."
He nodded and turned to me. "What do you think, Lisa?"
"Isn't it awfully short, Mr. Steele?" I said, swiveling my hips to
make the skirt swish around me.
"Master," he replied, looming over me.
I hated having to call him that. "It's awfully short, master."
"Makes it easier for you to bend over," he said with a smirk. "Oh, by
the way. Anyone who sees the white lace on your panties is allowed to
give you a little love tap. Not enough to hurt, just a little reminder
that the lace on your butt is the sign of a slut. Put your hands on
your knees."
I bent to obey, knowing he could see the lace on my panties. He gave
me a sharp little spank.
"Ooh!" I cried, though it didn't really hurt. In a weird way, I kind
of liked it. I wanted him to do it again. I straightened up and bent
over again, and he swatted me again. I started to get hard in my
panties. Oh my God, what was wrong with me?
"See?" he said. "The lace on your butt is the sign of a slut."
I straightened up, tried and failed again to pull my dress down, and
turned to Ms. Underbust. "Mistress, what do you think? Is this dress
too short? It doesn't hide my panties. I don't want people to think
I'm a slut."
She fluffed the hems of my dress and petticoat. "It is quite short,"
she said, "but not too short for a maid such as yourself. You need to
learn how to move gracefully in a short skirt without exposing your
most intimate underthings to men and giving them naughty ideas."
"But, ma'am, won't I be exposing the lace on my panties every time I
curtsy?"
"Oh, I doubt it. Your skirt and petticoat are full enough that a
curtsy shouldn't expose the seat of your panties. In any case, you
didn't seem to mind getting those love taps from Dirk."
That night, as I bent over the dishwasher to put in a plate, Mr.
Steele came up behind me. "The lace on your butt is the sign of a
slut," he said, and gave my bottom a swat. Sorry, a love tap.
I stood up straight and froze. "So now what am I supposed to do,
master? If I fill the dishwasher, I'll get a spank for every dish I
put in it, and I'll never get anything done, and you'll waste all your
time watching and spanking me."
"Good point, Lisa," he said. "Tell you what, I'll spank you only once
per task, not every time you expose your bottom during the task.
That'll save me time and spare you a lot of spanks."
"Thank you, master." I didn't feel very thankful, since the whole
stupid "Lace on your butt" rule was his idea.
He didn't limit himself to spanking. A few days later, as I climbed
the stairs to change the linens in the master bedroom. Mr. Steele came
up the stairs behind me, taking them two at a time, obviously in a
hurry. I flattened myself against the wall, as Ms. Underbust had
trained me to do when we met on the stairs. As he passed, Mr. Steele
reached under my French maid's dress and petticoat and gave a hearty
squeeze to both sides of my bottom.
I started and gave a little shriek of surprise, but didn't dare to
move or resist him. He sped up the stairs. "Sorry, Lisa, couldn't
resist," he said over his shoulder before disappearing down the
hallway.
I stood unmoving on the stairs, angry at him and ashamed of myself. I
was helpless against him, a helpless little sissy. I had good reason
not to want his hands anywhere near my crotch, but after this
incident, I knew it was inevitable that he'd grab me down there sooner
or later, and would find something he didn't expect, and then - what?
He'd probably beat the shit out of me.
I told Ms. Underbust about the incident. She was more sympathetic than
I expected and said she knew what I needed, though she wouldn't say
what. She said she would order it immediately, but it might take a
couple of weeks to arrive.
For the next week, Mr. Steele limited my discipline to occasional
swats when the lace on my panties showed, which was a relief, but he
had unwelcome news for me. The Minnesota football team - the Vikings,
he said - were playing their first game of the season on Sunday, and
he'd invited three of his friends over to watch it.
"And I want you to serve us drinks and snacks, Lisa," Mr. Steele said.
"In your French maid's uniform. You must curtsy to them and call them
sir. And remember, the lace on your butt is the sign of a slut. Make
sure they see it, and I'll tell them the rule."
I curtsied. "Yes, master." I was doomed. This had the potential of
being really bad. Me in the same room as four males who would spend
the afternoon drinking beer and feeling macho. I hoped Ms. Underbust
would stay to act as a brake on the males' behavior, but as far as I
knew, she didn't give a damn about football, and I feared I'd be left
on my own to protect my virtue... or at least protect my crotch
against close inspection.
On Friday before the game, a large package arrived for Ms. Underbust.
She opened it in her room and called me in.
"Yes, ma'am?" Curtsy.
"I have a present for you. It won't delight you, but it will protect
you."
"Thank you, ma'am." I looked in the box and saw a device made of
stainless steel and various synthetics. I picked it up and turned it
over in my hands until I figured out what it was: a female chastity
belt.
I gave my mistress a perplexed look. "I can't wear this, ma'am. It's
made for a female body."
"Maybe you're womanly enough to wear it," she said. "Try it on."
I took off my clothes, and she helped me into the belt, telling me the
device had been adjusted to fit a male form. The shield protecting the
wearer's pussy was cunningly made so that a man's penis - a small
penis, like mine - could be hidden underneath, if the man's testes
were tucked back into his body. I could wear this belt instead of a
gaff and look like a woman under my clothes, even if I lost my
panties.
I wondered what Mr. Steele would do to me if he discovered the
chastity belt. Well, if it successfully hid my boy bits, at least he
wouldn't tear me apart for being a boy instead of a girl. Ironically,
I was wearing the chastity belt to protect a pussy that I didn't have.
"It fits you perfectly," Ms. Underbust said. "Your body is getting
girlier."
"Yes, ma'am," I said, disliking the thought of having to wear the
thing. It shamed me that I could fit into a female chastity belt. The
thought made me stiff, to my further shame, and I discovered that the
belt had room for my hidden penis to expand. I could probably even
ejaculate in it, though it'd make a mess.
"I'm not going to tell Dirk you're locked up. Maybe he'll find it,
maybe he won't. If he does, blame it on me," she said. "I want you to
wear it whenever Dirk is here, because I don't trust him to leave you
alone. It's your fault, Lisa! You're just too tempting. That's why I'm
not giving him a key. You can tell him that. If he hurts or threatens
you in any way, tell me and I will deal with him."
I blushed. "Yes, ma'am." Curtsy.
Sunday came too soon. The game would start at noon. Like the big beefy
players on the field, I started preparing for the game hours in
advance, though in different ways.
I was pretty sure they didn't take bubble baths to start their day.
I doubt they moisturized their skin or patted it with perfumed powder
or anointed it with scent.
I doubt they shaved their legs and underarms, or depilated the rest of
their body, or waited for three coats of nail polish to dry.
I'm pretty sure they didn't spend as much time on their hair as I did,
even though some of them had more than I do, and I know they didn't
spend as much time on their makeup. That blotchy black cheekshadow the
NFL uses is just not attractive.
Oh, and I'm fairly certain they didn't wear lacy lingerie under their
uniforms, which were definitely not French maid uniforms with
extremely short skirts and four-inch black patent heels.
I made a big pot of chili and put out chips, dips and a bucket of
beers on ice for the boys, and retreated from the den and its big-
screen TV to the relative safety of the kitchen.
My mistress came down the stairs in a classic twin set over cashmere
trousers. A lovely outfit, and I wished I could be wearing it right
now instead my maid's uniform. "I'll be out for a few hours," she said
cheerily. She twinkled her fingers at me and abandoned me to my fate.
Mr. Steele - oh, hell, I'm going to call him Dirk, because he behaved
like a jerk.
His buds showed up shortly before game time, already well lubricated
and ready to get more so. Dirk summoned me from the kitchen and
introduced me to Wayne, Tyrone and Adam. I flounced up to each,
bouncing my pigtails, and curtsied to him in turn. I needed above all
to make Dirk and his friends believe I was a girl. I turned my hard-
learned femininity up to eleven. This was essential to avoid exposure
- but it had the predictable effect of making the boys more interested
in their girly servant.
I swished back and forth between the kitchen and the den, making sure
they never ran low on beer or snacks, while spending as little time in
their sight as possible, knowing that alcohol increased their chances
of becoming frisky.
At halftime, the boys informed me that the Vikings, who were in
purple, were tied with the team in white, whoever they were, and the
game was boring.
Dirk took another long swig of beer. "Let's see if we can spice things
up," he said. "Lisa, come here."
I stood before him, heels touching, hands behind my back, eyes humbly
lowered, hoping against hope he wasn't about to subject me to anything
dreadful.
"You're my maid, right?" he asked. His friends watched me instead of
the TV, where talking heads were babbling statistics.
"Yes, master," I said, knowing that's what he wanted me to say, and
curtsied, knowing that's what he wanted me to do.
"And you have to obey my orders, don't you?"
"Yes, master," I said, dreading whatever would come next.
"Well then, Lisa, I want you to give all my friends orgasms," he said.
"Before the end of the game."
I was stunned. He wanted me to get all these strangers' rocks off?
How? And how was I to avoid exposure, with four men staring at me? I
hoped my chastity belt would protect me, and reminded myself that Mr.
Steele didn't know I was wearing it. I dropped to my knees, overcome
by contradictory feelings of submission, fear and desire.
"How, master?" I said.
"You can blow them, or you can give them hand jobs, or you can let
them fuck you," Dirk said. His friends voiced enthusiastic support for
this plan.
"It might be difficult to fuck me, master," I said, trying to look coy
rather than defiant.
"Why not, Lisa?" he demanded.
"You have to find out, master," I said, curling a lock of my hair
around my finger.
He laughed. "Come here, Lisa," he said. I shuffled toward him on my
knees. He patted his thighs. "Sit here."
I'd already fought the battle of his lap and lost, so I dutifully
scooped my skirts under me, sat and displayed myself as prettily as I
could. I didn't know what Dirk was about to do, but I knew I needed to
react the way a girl would.
"Take off your panties, Lisa," Dirk commanded.
If I did that, I would expose my female chastity belt. The moment of
truth was at hand. "Yes, master." I clumsily pulled down my panties
while sitting on his lap. The boys hooted and cheered.
Dirk shoved his hand under my tragically short maid's uniform and
groped at my crotch.
"What the hell?" he said. With both hands, he lifted my skirt and
petticoat and examined what he'd felt underneath. "It's a fucking
chastity belt!"
His friends guffawed. "Locked out!" Wayne said.
"Denied!" Tyrone said.
"Off limits!" Adam said.
"Fuck! Tina must've done this!" Dirk said. "Well, guys, the offer is
still good! I can personally testify that Lisa here can suck the brass
off a doorknob, so get in line! She can do Wayne and Tyrone in the
third quarter, and Adam in the fourth."
"Not you?" Adam said.
"I'll have her all to myself tonight," Dirk said. "Well, Lisa? Your
master has given you orders."
I did it. I knelt in front of the sofa and gave blowjobs to his
friends. Master reminded me to look up into their eyes as I worked
their cocks. They made me go slowly at first, but near the end, they
grabbed my pigtails and face-fucked me until they came. I tried to
turn off my brain, but could not help feeling waves of humiliation and
submissiveness wash over me as I became a cocksucking sissy.
I went to the bathroom, brushed my teeth, washed my hands and fixed my
pigtail ribbons, and when I thought I could face the men again, I
started tidying up. My scalp hurt.
The game ended. Moments later, Ms. Underbust returned and breezed into
the den.
"How'd it go, boys?" she asked. I doubted she was asking about the
game. "Did our maid provide proper service?"
"Yes, she did, ma'am," Wayne said. "Even in her chastity belt."
"Ah, you found it, did you?" she said.
They laughed. "Dirk was sure surprised," Tyrone said.
"She did a great job anyway," Adam said.
"Well, I'm glad to hear she provided satisfaction," she said. "Did
your team win? Aww, that's too bad."
Dirk's buds all left shortly afterwards. I curtsied to each and gave
him a kiss. They all fondled my boobs or butt. It was embarrassing,
but I wanted the guys to like me, so that they would treat me nicely
the next time they came to watch.
When the last of the men left, Dirk turned to Tina. "What the fuck? A
chastity belt? I had no idea! You embarrassed me in front of my
friends!"
"But it kept you and your friends from fucking Lisa, didn't it?"
"Why does she matter so much to you? She's just the fucking maid!"
"But she's not your maid for fucking, Dirk! You fuck me, you don't
fuck her. That's why she's wearing that thing."
"You don't trust me?" Mr. Steele said.
"I do when you think with your brain," Ms. Underbust said. "I don't
when you think with Mr. Big here." She ran her hand over the bulge in
his trousers.
Mr. Steele smiled. "Mr. Big is thinking as hard as he can right now."
Ms. Underbust giggled. "Well, I'm right here in case he has any bright
ideas."
She started playing with him on the sofa. He told her to take it out.
She refused. Said they had a maid to do that for him now. Told him she
wanted him in bed instead. He followed her upstairs, practically
drooling. Men were so pathetic.
I cleaned up the den and kitchen while hearing them banging away in
the master bedroom. I wished it was me, not Dirk, up there with Ms.
Underbust. I wished I could have sex. I wished I didn't need to wear a
female chastity belt to disguise myself as a woman. It was all because
of Dirk. Dirk the Jerk. Dirk who was now my master, Dirk who could
order me to do almost anything.
Why did I put up with this? Because I was terrified by the thought of
leaving with no money, no ID, nowhere to go, wearing a maid's uniform,
locked in a woman's chastity belt.
~ ~ ~
Maybe he resented my chastity belt, or maybe he resented Ms. Underbust
for not trusting him, but for whatever reason, Mr. Steele changed his
attitude toward me. He made fun of me, bought me humiliating things to
wear, treated me like a toy, played embarrassing games at my expense.
I wasn't sure what he was up to. It made me feel even more powerless
and ashamed.
He started by making me wear a butt plug. A small one at first, then
larger ones as the weeks passed. He changed his "Lace on your butt"
game so that the winner could play with my plug instead of giving me a
love tap. He would push it in a little deeper, or draw it in and out,
or twist it inside me, or wiggle it back and forth. He told me to
pretend the plug was giving me girly orgasms, so I had to moan and
arch my back and call him master and beg him for more. It was utterly
degrading. I wondered why he didn't fuck me in the ass. Maybe he just
didn't like anal sex. I was glad - the butt plugs were painful enough.
For a month, he made me leave off my dress, petticoat and slip every
Nudie Monday and spend the day in just my corset, stockings, panties,
apron and cap. He gave me swats or played with my plug whenever he
liked, because the white lace on the seat of my panties was always
visible. By now, all my panties were black satin with rows of white
lace on the bottom.
I spent a weekend made up as his kitten. I had to wear a headband with
furry cat ears, eyeliner whiskers on my cheeks, black makeup on my
nose, a rhinestone-studded collar and leash, and a black leotard and
tights. He replaced my butt plug with one that had a kitty tail
attached. He made me crawl everywhere on all fours. He wouldn't let me
talk or use the toilet. Instead, I had to meow when I needed to go,
and he would take me into the back yard on my leash and make me squat
on bare dirt to do my business. I pooped only once that weekend, and
he made me use my paws to scrape dirt over it, the way kitties do.
On another weekend, he turned me into a baby. I had to wear adult
diapers and plastic panties over my chastity belt, an adult-sized baby
dress that didn't quite cover my diaper, and a baby bonnet that
limited my vision. I had to crawl everywhere, like when I was a cat. I
had to have a bottle of milk or a pacifier in my mouth at all times. I
spent hours in the den forced to sit inside a real baby playpen,
playing with a doll and watching infantile shows on TV. He watched me
on a security camera to make sure I wasn't breaking any of his baby
rules.
I think he got off more on the idea of turning me into a baby than the
reality of it. The breaking point came when Ms. Underbust refused to
change my diapers, and Mr. Steele decided he didn't want to, either. I
was out of diapers and back in panties before sundown. I thought I'd
escaped from humiliation...
But I hadn't. Instead of a baby, Mr. Steele turned me into a little
girl. He dressed me in an adult-sized little girl's frilly pink party
dress, with a Peter Pan collar, a bodice embroidered with flowers,
puff sleeves, a filmy skirt that barely reached my thighs, and a wide
pink sash that he tied in a bow behind my back. Under it I wore Disney
Princess panties, a girl's camisole, and a scratchy net petticoat that
rustled whenever I moved. Completing my little girl outfit were lacy
ankle socks, Mary Jane shoes, pigtails tied with bright pink ribbons,
and matching pink nail polish and lipstick.
I looked - and felt - about six years old. My mistress and master
spoke to me as if I was a little girl, making me call them Mommy and
Daddy and using lots of cutie-pie words. Sometimes they told me to
suck my thumb instead of talking. Sometimes they made me skip
everywhere. I liked wearing the dress, but I hated pretending to be a
six-year-old and couldn't wait to become my real age again.
Unfortunately for me, Mr. Steele went through a bondage phase, my
least favorite of all. For a month on Tuesdays and Thursdays, I wore
padded cuffs and foot-long chains between my wrists and between my
ankles, and another chain connecting the wrist and ankle chains,
making it almost impossible for me to raise my arms above my
shoulders. He buckled my rhinestone collar around my neck and attached
my kitty leash to it so that he could lead me around the house.
For a day, he made it a rule that I could move from room to room only
if someone led me by my leash, but it was such a bother for him and
Ms. Underbust to move me around for chores that he canceled the rule.
When I wasn't working, he locked a chain from an eyebolt in my bedroom
ceiling to my collar, a chain long enough to let me lie on the bed or
crawl on the floor, but not long enough to reach the door.
When he tired of chaining me up, he started making me wear girls'
Halloween costumes instead of my maid's outfits. He liked me to dress
up as a ballerina, in a leotard, tights, ballet slippers and a real
tutu, with my hair up in a bun, and made me do lots of ballerina
curtsies. From a costume rental shop, he brought home in turn a yellow
satin princess dress with a tiara, a Cinderella dress with a huge blue
skirt, a Scarlett O'Hara hoopskirt with a crinoline, a fairy dress in
shades of green chiffon that fluttered like leaves in a forest breeze,
and a Wonder Woman outfit with a bustier, short skirt, knee-high
heeled boots and a tiara. It felt odd for Wonder Woman to be dutifully
hand-washing her mistress' lingerie in Woolite and hanging it out to
dry.
Mr. Steele ordered me some Lolita outfits from Japan - incredibly
frilly skirts and blouses with overskirts, aprons, and layers of
petticoats, all in delicate, feminine fabrics trimmed with ruffles,
pleats, embroidery, lace, ribbons and bows. The outfits included
colorful stockings, platform shoes, and elaborate wigs, elaborate
bonnets and hair jewelry. I felt more girly doing my chores in a
Lolita dress than in any of my maid's uniforms.
And then there was the wedding game.
Ms. Underbust rented me a wedding gown with all the underpinnings for
a weekend, and on Saturday afternoon, she escorted me to her salon,
where she had them put my hair in a bridal updo and do my makeup. Back
home, she pulled out a bunch of garment bags and made me put on
wedding lingerie, bridal petticoats, a veil and a white A-line gown
with a lace bodice embroidered with seed pearls. Mr. Steele put on a
suit. Ms. Underbust wore a black skirt and white blouse and pretended
to marry me to Dirk.
She played the wedding march on her phone. I walked slowly across the
living room to join Mr. Steele at a pretend altar. Ms. Underbust read
an extremely abbreviated wedding service in which I promised to love,
serve and obey him. We said our I do's, and she pronounced us master
and sissy. He put a costume-jewelry ring on my finger, lifted my veil
and kissed the bride.
He picked up me and the gown with ease, he carried me upstairs to the
master bedroom and dropped me on the bed. The skirt of the gown fell
back, exposing my layers of petticoats. I was terrified, not knowing
what he planned to do to me, but she rescued me by telling Mr. Steele
that we needed to attend the wedding reception before there could be a
wedding night.
She led us back downstairs and poured us all flutes of champagne, and
to my great relief, that was the end of the game. Ms. Underbust
announced that I would be spared a "wedding night" with my mock
husband, which gave the two of them another good laugh. As we waited
for our favorite restaurant to deliver our dinner, I sipped my
champagne and said as little as possible. The only part I'd enjoyed
was putting on and wearing the wedding gown. I'd never worn one,
absolutely loved the feeling, didn't want to take it off tonight and
was sorry we had to return it. Like my Cinderella dress, it would have
been completely impractical for housework, but in it I felt like a
princess.
The main problem with the wedding game - maybe the only problem - was
the groom.
I wondered what Ms. Underbust thought of the ways Mr. Steele was
playing with me and the clothes he was making me wear. The cost wasn't
an issue - she was well off, and I gathered his business was
flourishing - but he was focusing so much of his attention on me
instead of her that I wondered how healthy their relationship was. I
managed to hint at this while talking with her one day, and she put me
at my ease, sort of.
"Oh, I don't mind," she said. "I mean, I think it's silly that he
makes you go around wearing those ridiculous outfits, but if it
doesn't bother you, it doesn't bother me." Actually, it did bother me
- did she think I liked wearing diapers or chains? - but she went on.
"He likes shiny new toys, and you're his shiny new toy at the moment.
When he tires of playing with you, he'll start leaving you alone to do
the housework, and I'll be ready and waiting for him."
"But what he makes me do, it's just so embarrassing!"
"Embarrassing? Says the boy who willingly wore lingerie and a maid's
uniform to get his first job?"
She had me there. "Yes, ma'am." Curtsy.
I always worried about Mr. Steele discovering my boy bits, but he
discovered my lack of girl bits instead. I was sitting on the sofa
with him one day, feeling sexy but ridiculous to be wearing my Wonder
Woman costume while watching Gal Gadot kick ass on TV. He had his arm
around me, and after one particularly exciting fight sequence, he
slipped his other hand into one of the gold-trimmed cups of my red
bustier.
"Eeek!" I shrieked in surprise. He usually left my breasts alone -
they were unimpressive, more moobs than boobs, and he seemed to be a
legs and butt man. I wasn't wearing a bra under the bustier, so he
discovered my other secret right away.
"Lisa! What the hell? Falsies?"
I was so embarrassed. I should have worn a strapless bra under the
bustier. "Yes, master.... I'm sorry... I don't have big breasts. Lots
of girls like me wear them."
He pulled my breast forms out of the cups. By now my mistress had
bought me small silicone forms to replace the balled-up pantyhose I
wore in my first bra. He set them aside and brushed my real nipple
lightly. A thrill ran through my body, and my nip erected. It was
small, but it was definitely upright. He flicked it with his finger. I
gasped.
"Does that feel good?" he asked.
"Yes, master!"
"Are your breasts still growing, or is that as big as they'll get?" he
asked.
"I don't know, master."
"Would you like them to be bigger?"
It all depended. Was I going to be a girl for the rest of my life? Or
was my time as Ms. Underbust's maid just an aberration? Would I grow
up and change back into boys' clothes and go to college and get a job
and marry and start a family? That prospect felt way too normal,
but... well, it was normal. If I accepted that I was a sissy maid and
needed to look like one, there were big changes I needed to consider,
and one of them was the state of my bosom. I needed to talk to Ms.
Overbust about it.
"Larger breasts would look better on a maid, as long as they didn't
distract her master," I replied. That much was true.
"I could give them to you," Dirk said. "A girl as pretty as you should
have nicer tits." He played with my nipples. I sucked in my breath,
felt my nerves vibrate with pleasure.
"How...?"
"I'd pay for you to have implants," he said. "They'd be quicker than
hormones, right? What are you now, an A cup? You should have C cups at
least, don't you think?"
"I don't know, master," I said. I found myself unconsciously thrusting
out my flat chest at him. I knew Ms. Underbust was a D cup and didn't
want to compete with her, so C sounded perfect. "Aren't they very
expensive?"
"Don't worry about it. Real breasts will be even more fun for you than
dressing up as my favorite female superhero."
I wasn't too sure about that, but real breasts certainly would fill
out my dresses better than breast forms, and the soft bras and slips
and nightgowns I wore might feel delicious sliding over womanly
nipples. Life would be better with breasts - if I remained a girl. Not
so much if I ever wanted to be a boy again.
I talked it over with Ms. Underbust. She said she'd been meaning to
ask. She offered to pay for breast reduction surgery if I ever needed
it, so I agreed to have implants. She asked me if there was anything I
wanted to have removed, and I said no. My cock and balls weren't much
use to me now, but I couldn't foresee the future.
She scheduled the surgery and drove me to my appointments and
consultations. On the morning of the procedure, she and Mr. Steele
both came to the hospital with me. The operation was expected to last
up to two hours, and if all went well, I'd be home by early afternoon
with a brand-new bosom. I was lying on a gurney in my hospital gown
with an IV in my arm when a doctor came to make a final check.
"We're giving Lisa two C-cup breast implants, correct?"
"Yes, doctor," Ms. Underbust said.
"And we're not removing the testes or penis, correct?"
Dirk's jaw dropped. "What?!"
Ms. Underbust laid a firm hand on his forearm. "Not now, Dirk. Just
wait and I'll explain. No, doctor, we're not."
The doctor finished his check and said I'd be going into surgery in a
few minutes.
Dirk was staring at me, hard. He managed to keep his voice down.
"Tina, what the hell's going on here? Is Lisa a boy or a girl?"
"Lisa was born a boy, but she's all girl inside," my mistress said. "I
found that out when I had her house-sit for me. She tried on all the
clothes in my closet, and afterwards she agreed to become my maid, and
as far as I know she hasn't worn boys' clothes since I took all of
hers to Goodwill. Lisa is a pretty little sissy, small and weak,
dainty and submissive. She's more feminine than most of the genetic
girls I know, and cuter, too. I mean, she fooled you."
"He did!" Dirk almost snarled. "All this time, both of you let me
think he was a girl! You tricked me! I made him give my friends
blowjobs! If they knew..."
"Keep it down, Dirk. Lisa's sucked you off, too."
"I know! Too gay! I wouldn't have done it if I knew he was a boy.
What's his real name?"
"Oh, Dirk, Lisa isn't a boy! She was born to wear panties and dresses.
Just look at her!"
"But he has a cock and balls, right?" Dirk said. "I mean, how can a
boy wear a chastity belt for a girl?"
"I had it adjusted," Ms. Underbust said. "Fortunately, Lisa has a
slender waist and is, um, modestly equipped."
"But..."
The two of them shut up when a doctor and nurse arrived to wheel me
into surgery. The doctor added medication to my IV and said I would
fall asleep quickly. My last thought was that I was going to miss the
rest of the conversation between my master and mistress. I'd expected
Dirk to explode when he learned I had male parts, but he didn't, even
though it obviously took him by complete surprise.
When I woke up in recovery, they were both there, apparently at peace
with each other. We were alone in the room. A nurse came in to check
on me, told me I was doing great and left.
"How are you feeling, Lisa?" Ms. Underbust asked.
"My stomach's a little wonky, ma'am, but otherwise I'm okay. How do my
breasts look?"
"They're all covered up, but your figure looks much better, more
feminine," she said. "Oh, and I have news!" She extended a limp left
hand toward me. A diamond gleamed on her ring finger.
"Oh!" I squealed. "Are you engaged?"
"Yes!"
"To Mr. Steele?" Stupid question, but I had to ask. They'd been
starting a fight when I left. I guess she won.
She rolled her eyes. "Of course!"
"Congratulations!" I said the expected words, but had decidedly mixed
feelings. I liked living with Ms. Underbust, but I could not say the
same of Mr. Steele. "Did all this happen while I was in the operating
room? Did he get down on one knee?"
"Yes, I did," Mr. Steele said. "Before we go any further, I want to
apologize."
That would be a first. "For what, master?"
"For the way I've treated you. Like a plaything and not a person. I'm
sorry, Lisa."
My jaw dropped open. I shut it. What a day of surprises! Since when
did Dirk the Jerk realize I was a person?
"Tina and I had a talk while you were in surgery," he said.
"I would call it more of a come-to-Jesus meeting," Ms. Underbust said,
tapping her foot.
"Yes." Mr. Steele seemed subdued. "Well, she made me realize I was
using you to avoid dealing with the big real-life decision I need to
make. I played games like 'Lace on your butt' because they were less
stressful and more fun than deciding to get married and settle down
and, who knows, become a family man."
Wow. These were the most self-aware thoughts I'd ever heard him
express. I wondered what Ms. Underbust had told him to put him in this
state of mind. Maybe he was speaking from his new orifice, the one she
tore into him. He seemed softer spoken than earlier, maybe even
slightly cowed. Well, I knew what my mistress was capable of, and
frankly didn't mind if she had put the fear of the Goddess Tina into
her man. I just wished I could have seen it.
"Wow! What a lot to think about! What are you going to do, master?" I
said.
"I love Tina and I'm going to marry her," he said, "and we hope you'll
be our housemaid."
My mistress nodded. "And my bridesmaid," she said. "I'll show you the
dress, it's pink and very girly. You'll love it!"
I turned to Mr. Steele and searched my heart for the right words to
say. "You treated me badly, master, and I didn't like it, but I accept
your apology. All I ask is that from now on, please think of me as a
person, not just a plaything."
"Dirk needs to do more than that," my mistress said. "He needs to
understand that you're a sissy. Not a girl, not a boy, but a sissy, a
delightful combination of the best of both genders. You're not crude
and violent like a man, and you're not bitchy and backbiting like a
woman. You are a perfect servant and a lovely person who deserves to
be treated with respect. I'm proud to have you as part of my
household, and I hope you'll stay with me forever."
"So do I," my master said. "Tina told me something that really got to
me. She said that I was not treating you the way a gentleman should
treat a faithful servant... regardless of whether she's a boy or a
girl or a sissy. That stung. She was right. I'll do my best to be a
gentleman from now on."
I was so happy that I started to cry. "Thank you, master, thank you,
mistress! Wow, I'm going to be a bridesmaid! Oh, and thank you so much
for my boobs! Can we go home now?"
The End