Will You Ever Let Me Cum Again?

by TiltingatWindmills

story tags: cross_dressing, forced_feminization, sissification, maid,
femdom, female_domination, denial, tease_and_denial, chastity

https://www.literotica.com/s/will-you-ever-let-me-cum-again


https://www.literotica.com/s/will-you-ever-let-me-cum-again

Taylor is forced to become a sissified maid.

Page 1 of 3 page(s) (22125 characters)

*In a matriarchal dystopia, the weakest men become the maids*

I realized I was going to lose the wrestling match the moment I got an
erection.

I had already failed the strength trial so there was no way I would be
given a typical male work placement in a mine or a construction site.

I had nearly performed well enough on the scholastic tests to qualify
for a rare male college admission, but fallen just a few points shy.

And so my last hope of avoiding a life of domestic servitude was to win
a wrestling match.

The state government wanted to ensure that any man who entered the
domestic worker program was as docile as a kitten. If an average woman
could subdue them in a ring that was proof enough.

And that's how I found myself staring at a female college student
wearing a singlet.

She looked better in it than I did. Nicer curves, more toned legs even.

Hair up, no blush, no eyeliner. Her cheeks were flushed and there was a
little perspiration on her temples. It wasn't her first match.

She was maybe an inch of two taller than me.

Cute in an unconventional way.

"Hey, listen," she said in a conspiratorial whisper as we circled one
another at the start of the match. "I need to lose a few matches here
and there or they'll think I'm too good to be a test wrestler. I can go
easy on you if you like?"

Hell yes.

I had no desire to wear a stupid maid outfit for some rich family.

I glanced over at the referee, and the audience beyond her.

"Sure," I whispered back and nodded my head eagerly in case she hadn't
heard me.

"Alright let's do this."

I had never fought a girl before.

It felt wrong, laying my hands on a woman. But I don't think she felt
the same way.

By the time I grabbed onto her shoulder for a good grip, I was already
halfway to being thrown on the ground. Once there I managed to get a
feeble grip on her thigh and tried to keep things under control.

And it was a nice thigh. Soft flesh under my fingers, taut muscles
flexing beneath the skin.

But it wasn't the time for that.

We rolled around. First she was on top, and then I flipped her over,
before she quickly got back on me again.

When exactly was she going to start losing?

She managed to pin both of my wrists above my head and her ponytail
dangled in front of me, tickling my nose.

It smelled like sweat and lavender.

I thrashed around and was surprised at her grip.

It was just then that I felt the tingle in my crotch.

Fuck.

When dealing with an unwanted boner, few items of clothing will offer
less modesty than a wrestling singlet.

I tried to think of something else.

I needed to focus on not losing.

But as I writhed beneath her I realized that she was much stronger than
I was, and that losing was the source of my arousal.

I liked being dominated by women, as it turns out.

What a moment for self-discovery.

"Sorry," she whispered, "I can't lose to someone this weak. They'll
look at your weightlifting scores and know I wasn't trying."

She licked her lips as she spoke, making her apology a little less
convincing.

My dick was definitely hard now. Not growing - just all the way grown
up.

I heard the referee begin a countdown and twisted my hips, managing to
dislodge her long enough to reset the timer.

I rolled onto my stomach, extending the match and hiding the bulge in
my singlet.

I felt like a turtle trying to keep its belly on the ground. She tried
a few ways to turn me over, eventually entangling me with her legs and
flipping me back again.

"You're hard," she smiled down at me as she tried to force my shoulders
to the mat a second time. "Like a baby carrot," she winked. "It's
alright. I like making boys like you hard."

Hearing this did not help my situation.

"It feels good knowing I gave them the last erection they might have
for months. Maybe years."

Okay she had definitely been toying with me.

My cock twitched as she taunted me and I wondered if she felt it.

If she did, she didn't dwell on it, instead taking the opportunity to
pounce forward, pinning my biceps beneath her knees.

She had me irreversibly pinned, amd was absolutely casual about it.

I heard the referee start the slow, drawn out countdown.

"Three," shouted the referee.

My face was inches away from her crotch. I glanced at it and then back
up at her face looking down at me.

"This is my favorite way to end a match," she smiled serenely as I
thrashed my lower body underneath her. "But I can't pull it off on
everyone."

"Two."

"Easier on boys like you. Pretty face, small body."

My arms ached underneath her hard knees, but I could not move.

"One."

"Ladies love your type for maids. I hope she dolls you up nice. Whoever
she ends up being."

I finally went limp just in time to hear the referee declare, "Match
finished."

She eased back above me, but stayed perched over my face.

"It was nice meeting you Taylor. Maybe I'll see you again, serving
appetizers at some dinner party. If the hostess is okay with it, I'd
like to pick up where we left off. I love having my way with boys like
you."

Then she stood and walked off, leaving me to walk back to the change
room in defeat.

***

If you lose the match, that's it.

There is no appeal and no wasted time. You go to the showers first, and
then a fitting room.

Your chastity cage is sized, tested and secured with a tiny padlock.

It's a transparent plastic, a temporary device until the preferred
color and style of your mistress, whoever that will be, can be ordered
in.

I stared at my little cock as the nurse iced it down and stuffed it in
its plastic chamber. I entertained a passing moment of Schadenfreude
towards to it.

"If you hadn't betrayed me, maybe I would have won the match." I
imagined saying to it. "Look at where it got you" I mumbled as it
filled the confines of its new prison.

I knew this had always been a possibility.

Even if the government hadn't forced chastity on me, it was likely that
a girlfriend or wife would insist on it later.

But that felt like it would be more of my choosing. A worthwhile
exchange for a loving relationship.

Now there was no hope of having a girlfriend or a family and I was
being forcefully cut off from accessing part of my own body. I felt a
pinching pain deep in my gut that this was wrong and unfair.

But there was little time to bemoan my misfortune.

I was off to the show room, literally being led on the end of a leash
that clipped onto my padlock.

I found myself standing on one of many small pedestals, wearing nothing
but that clear plastic cage, as dozens of women filed past, looking at
potential maids.

"Don't hide those beautiful blue eyes honey," an attendant advised with
a prod when I tried to ignore the procession of female shoppers.

I was used to being touched - our finishing school chastity classes
were co-ed - but even so, it was unnerving having middle aged women
approach you so casually only to immediately weigh your testicles in
their hand as if they were at a meat market.

More unnerving still was the idea that any one of these women could
purchase me for their household.

Some of the women carried clipboards, others jotted notes on their
phones, deciding if they would interview me later.

I recognized a mom of one of my wealthier classmates.

"Hi Taylor, I like your outfit," she said as she got closer.

I smiled back, deciding immediately that I didn't want to serve in her
house. I could be rude, but if you put off enough customers there's
always a chance you aren't sold and await an even worse fate. I settled
for being awkward instead.

"Hi Ms Nance," I mumbled.

"Jenny, come over here," the woman called to her daughter who was
inspecting some other soon-to-be serf.

I'm not sure if I was blushing furiously or if all color had drained
out of my face.

Jenny emerged from behind a pack of nearby women and giggled in
surprise.

"Oh Hi Taylor."

"Hi Jenny."

No eye contact from me. I might not be allowed to close my eyes, but I
could definitely look away.

"We saw you got a little excited during the match," Jenny said.

"We thought it was endearing" her mother added. "It's good when boys
like losing to women," she added.

"Thank you ma'am" I managed to say.

"Have you seen it in class?" Jenny's mother asked her, motioning at my
locked penis. "Is it as small as it looks?"

I continued staring intently at the ground like there was some sort of
crossword down there I needed to solve.

"Yeah I think it was the smallest in our cohort."

No meanness in the tone, just factual.

"I kind of like that for a maid, don't you think?" Her mother moved my
cage side to side as she inspected me.

"Yeah, I guess." Apparently Jenny hadn't given it much thought until
now. "It would feel like a bit of a waste otherwise."

"Your aunt had a maidservant with a huge penis once. Really
disproportionate to his little body. She used to show it off like some
sort of novelty. I suspect she may have actually used it herself on
occassion. Sort of poor taste if you ask me."

"Agreed," Jenny said.

"So would you consider having a former classmate as a maid?" Her mother
asked.

"I wouldn't be bothered by it. This one would be easy to control."

"Oh?"

"Veronica was his keyholder in class when we did the three week
chastity trial. She unlocked him for cleanings and all that. She said
when she didn't let him cum he was already begging before the end of
the first week. But she just kept denying him and apparently he kept
going down on her to try and earn his freedom."

"Was he any good?"

"I think the word she used was 'over-eager'."

"And if we brought him home, do you think you would use him?"

Jenny looked me up and down as she considered it.

"Hmm, only if you didn't want him."

Her mother smiled. "Well, let's have a look at a few more candidates.
We don't need to buy anything today if we don't want."

"It was good to see you," Jenny smiled brushing her hand against my arm
before gracefully leading her mother to their next potential
interviewee.

I always found it impressive how casual women could be around naked
men. No matter how long I spent in that vulnerable position it never
ceased to lend them an aura of power.

But there are some women who never get used to it.

One such woman stood out to me from that showcase session.

A cute, half-Asian college girl, unaccompanied by any parent or
partner. She was wearing a plaid skirt, a blue, knitted cardigan and a
matching headband. I glanced at her full breasts as she approached and
immediately looked away when I saw that she had caught my gaze.

Her outfit was well put together, but not particularly expensive, which
made me wonder how she expected to purchase anyone at all.

She was wearing glasses, the kind that are fashionable at the moment,
but perched them on her head when she got closer.

She didn't say anything, but looked a little nervous. Maybe she knew
she was out of place.

Most of the prospective buyers would feel you up a little bit at this
stage. Poke your arm, maybe squeeze your ass and so on. She approached
tentatively, and walked around me in a circle. Then she reached out her
hand as if to cup my balls, before withdrawing it suddenly with a
blush.

Her face in that moment was particularly adorable. Small round lips, a
cute button nose, and big dark eyes that stuck in my memory.

But I had little time to admire her before she turned and left.

The showcase continued for another hour, leaving the afternoon for
interviews.

"Would you be comfortable managing a large house?"

"Have you ever cooked for high-end guests?"

"Do you have any reservations about being shared among female friends?"

It was a slog. Middle aged women, matronly women, pearl necklaces and
pantyhose.

Near the end of the first day, that young, half-Asian woman walked in
alone.

"Hi, my name is Lucy."

"Nice to meet you. I'm Taylor."

There was a pause. I was being sold into servitude and wasn't about to
lead any conversations unless I really thought this was a house I
wanted to end up in.

"So... are you feeling okay? Did she hurt you?"

"The nurse? She was a little rough I suppose but..."

"No during the wrestling match. I was watching, I wondered if it hurt?"

I had to think back. Pain hadn't been my biggest concern at the time.

"No, I'm fine. Thank you for asking," I said, pleasantly surprised.

She looked like she was deciding on her next question. She tucked her
long black hair behind her ears, and I noticed for the first time that
they stuck out a little. It was a quaint flaw that somehow made her
more appealing. I guess because she seemed more down to earth.

"Maybe, could you tell me about yourself then?" she asked.

I mentioned the basics, 19 years old, only child, and so on.

"Hobbies?" she persisted.

These were not the usual questions I can assure you.

"Umm... I have this weird thing where I like to make tiny figurines. I
paint them, put outfits on them."

"Oh like for dollhouses?" she perked up.

"Yeah actually. I have sold a few to people who use them in dollhouses.
Honestly I don't usually go around talking about it. People think I'm
strange if I mention it."

"Well I love costumes and outfits. I always wish I had a younger sister
to dress up. Maybe it's kind of similar."

I nodded. "So, are you not going to ask about my cooking?"

She laughed. "Well they have a file on you," she indicated some loose
papers she was holding. "Excellent grades in culinary arts, and
honestly I'm not a picky eater."

"Not a picky eater, not wearing expensive clothing... what are you
doing buying a maidservant?"

"I'm in between degrees and starting an internship."

Okay, so only a little older than me.

"And I won a government grant to support promising young women so they
can focus on their careers."

"Congratulations," I said with only a trace of bitterness.

"Thanks," she replied. "So I do have one last question."

"Go for it."

"What's your libido like?"

I squinted, wondering what her ideal answer was, and still evaluating
if I'd rather be her servant than work for an elderly woman in a
knock-off Palace of Versailles.

"Average."

"So you masturbate like once a week?"

"Once a day," I estimated conservatively. "At least until today."

"Hmm," she said, perhaps reconsidering her assumptions on what was
average. "I just ask because I will expect my servant to stay in
chastity, but I'm not much of a disciplinarian if they start acting up.
In general I also just find penises to be sort of distasteful."

This was a big red flag. Like the kind of flag you'd see at a communist
parade.

There was a saying men sometimes whispered to eachother: 'never settle
for a woman who likes your cage more than your cock'.

But then again, this woman was really, really cute.

"You must have hated taking chastity class before going to college.
It's pretty hands-on."

"I was homeschooled."

Okay, I thought, maybe she's just a bit innocent then. She could
probably get used to dicks if she gave them a chance.

Dicks can grow on you after all. Mine grows on me all the time.

I glanced again, almost involuntarily, at the swell of her breasts
under the cardigan. If I was her maidservant, there was a good chance
I'd see them. Even just if she asked me to hand her something when
she's in the shower.

I made a flash decision, which may have been more about boobs than it
should have been.

Lucy was cute, and thoughtful. A little nerdy and awkward, and I might
not get to orgasm as frequently with her, but I was going to take the
risk.

"Lucy, I'm going to level with you. I don't like rich people. I'm not a
rich person. If I was I wouldn't be here. But I like you. I like that
you're a hard worker. And I want to be on Team Lucy."

She flashed a grin (what a smile she had), and so I kept going.

"If you need me to do dishes or cook or go shopping - I'll do those
things. But I have a good head on my shoulders, so I can run your
finances and maybe even edit your papers or memos or whatever you
need."

She was beaming now. I laid it on thick.

"And you don't need to worry about me trying to escape from chastity.
I'm a good boy. And I'm sorry if I was a little abrasive for a second
there. I've had a bad day, but I'll handle my emotions better in the
future."

She bit her lip and my heart fluttered. Later I would realize this was
her signature move.

"My grant is only enough for a three year contract," she said. "But if
nobody else outbids me, I think this could work out."

***

Lucy's internship was on the other side of the country.

Goodbye ma, goodbye pa!

At least I wouldn't have to explain to anyone I knew that I had ended
up at the very bottom of the social ladder.

When we arrived at Lucy's new apartment, a large government issued
package was waiting for us in the entryway.

I opened the box I found a variety of women's clothing: dresses,
skirts, high heels and so on. My heart sank.

"Lucy, what are these for?" I asked, my palms already sweating as I
held up a pinafore to the light.

"They're for you silly. A maid needs a uniform."

I hesitated, wanting to approach this carefully.

"You never mentioned this before. It's kind of an old fashioned
approach, don't you think?" I tried to tread lightly.

Of course I knew many male servants were forced to wear a French maid
uniform around the workplace, some even in public, but it was usually a
sort of status symbol. The owner really wanted you to know that they
owned a maid, and not one that was an efficient cleaner or cook, but a
luxury item who could wear high heels around the house and orally
please your wealthy guests.

I thought I had avoided this by ending up with Lucy.

"You don't like it?" She sounded disappointed. "Listen it's just for
around the house, to get you psychologically settled into your new
role."

She sorted through the outfits, selecting a tulle skirt, white
stockings and a corset.

"Start with these. Just try them on for your first day. It will be fun.
You know I like dress up."

I swallowed hard and she saw my hand tremble slightly.

She gently layed her hand on mine and steadied it. "Listen, I know some
of the women who make their maidservants wear these are quite harsh. I
won't be like that. I will never spank you in public or whatever it is
that has you scared."

The phrase 'spank you in public' left open the idea of spanking in
private and I couldn't help but feel an illicit thrill at the idea of
her touching me.

She pulled out a small black strip of lace and fastened it around my
neck.

"See, you're wearing a choker. But nothing changed. You are such a
beautiful boy, it would be a shame to not lean into that a little. Now,
I'm going to go shower. When I come out I want you all dressed up and
sitting in front of the mirror in my bedroom."

I started with the stockings, slipping them up my smooth legs and
trying to ignore the churning emotions as I did. They felt lush. And my
naturally hairless legs looked so feminine. It was a shame that men
couldn't wear these without sending so many wrong signals.

When I changed out of my boxers and into the simple satin panties that
Lucy had quietly set next to the rest of the outfit I felt a
disquieting shiver.

The bulge of my cage pressed forward from behind the fabric. It looked
so out of place.

Then followed the rest of the undergarments, the skirt, and the corset.
And finally the heels. I stared at myself in the mirror.

How had this happened to me?

When Lucy emerged from the bathroom she squealed and clapped, kissing
me on the cheek.

It felt good making her happy. Even if that happiness came at my
expense.

"You're perfect. Now one more thing, we should get you started on the
patch right away."

Will You Ever Let Me Cum Again?

by TiltingatWindmills (UID 6248561)

https://www.literotica.com/s/will-you-ever-let-me-cum-again

Taylor is forced to become a sissified maid.

Page 2 of 3 page(s) (21836 characters)

She dug through the box and pulled out a small medical kit.

"What is that?" I asked suspiciously.

"The government office recommends a minimal hormonal treatment when you
start. Some men find this position to be a bit of a shock. You're
giving up any hope of having your own partner or family. It's a lot to
take on. This will help you relax and settle in."

"Lucy, I'd rather not if it's all the same."

"Taylor, you've been shaking like a leaf ever since you opened a box
with some maid outfits in it. I think you would absolutely benefit from
this. Don't worry, it's just a patch."

Without asking she pressed it against the skin on the center of my
back, just below the corset and out of sight.

I suppose that was the proper location for the medical ingredients to
absorb at a certain rate, though later it occurred to me that it made
the patch rather difficult to remove.

My shoulders sagged in defeat but at least it wasn't some invasive
injection. How bad could a skin patch be?

"Here, shoulders back now. You need to remember your posture. Won't do
to have you moping around the house in an outfit like that."

I straightened up and put on a brave face.

"Perfect. You look great. Why don't you get started on dinner while I
message my family to tell them about the trip."

The evening passed quickly and with no more thought given to my
uniform. After preparing dinner I needed to wash up the dishes and then
unpack Lucy's belongings.

She showed me how she wanted her walk-in closet arranged and then I did
my best to follow her instructions.

I felt like an intruder when it came time to organize her underwear. I
had barely met her and here I was arranging her bras in a row.

I couldn't help but notice her underwear. Most of it was in a simple,
girly style, bright stripes or polka dots on cotton, but she did have
some nicer lace items.

Soon enough I'd be handwashing them without giving it a second thought,
but for now each item held a mystical allure. They had all been so
close to her...

I finished unpacking and laid out some outfits for the next morning
that I thought she might want based on the weather forecast and what I
had seen her put together on previous days.

I said goodnight and went to the small room that was to be mine for the
moment. Just a cot and my suitcase on the floor.

I was drifting into unconsciousness when I heard my door creak open.

"Taylor?"

Lucy was standing in the doorway, backlit by the hallway light like
some angelic creature with a halo.

Her long hair was down, and she wore a baggy t-shirt on top of fuzzy
pyjamas.

"Could you come sleep next to my bed? Just for tonight?"

I smiled to myself. Lucy may have been calling the shots, but at the
end of the day she was just a young woman who had left her small town
behind and moved to the big city.

I nodded with a smile.

"Of course."

Her room had a carpet, and when I tucked half of my blanket underneath
me I found it to be bearable.

Staring up at the ceiling I listened to Lucy's breathing as it steadied
into a slow oceanic ebb and tide.

And then I fell asleep too.

The next week Lucy and I found a pleasant routine together.

She gushed about my cooking and was endlessly grateful for the steps I
took to clean and decorate the apartment while she was on her first
days at the internship.

And almost immediately I felt the effects of the patch at work in my
body.

The first thing I noticed was how much more attentive I was. Not just
with Lucy, but even women I encountered shopping for groceries or on
the street. I was constantly putting myself in their shoes,
anticipating what might help them or make their lives better.

I understood now why the government might recommend such a drug for a
maidservant. And I didn't even mind. It was just reasonable. Why not be
happier and better at my job?

At the same time I noticed some less reasonable changes which I decided
must simply be side effects. The world seemed more saturated. Colors
were brighter, and sensations were stronger.

I looked at my new wardrobe with different eyes. I had always had a
knack and an appreciation for fabric, but now I saw a second layer of
beauty to my assigned outfits. They weren't cheap costumes, but well
made items designed for long term use and I was impressed at the
government's willingness to give them to Lucy.

There were downsides as well. One morning the elevator was out and I
had to climb six flights with a heavy bag of groceries. My legs felt
like they were ready to give up on me by the third floor, despite being
in relatively good shape. What little muscular strength I once had was
gone.

I thought about the wrestling match I had lost and how much worse I
would have fared now. If I had been a little weaker than the average
woman back then, I hesitated to think where I would rank now.

Even riding the bus made me feel vulnerable. Obviously any of the men
could overpower me if they wanted, but so too could most of the women.
And while Lucy let me wear my normal street clothes in public, it took
so much effort to change in and out of everything that I kept the
underwear the same. Since I was so busy it seemed prudent whenever I
left, but then while I was out I would look around me and wonder if
anyone ever noticed the silhouette of my cage or my panty lines through
my trousers.

About a week into moving in I began to notice other changes. My nipples
became sensitive such that I despised the friction of my old clothes
and I could swear that I was gaining fat in some places while losing
muscle in others.

Also, I was always horny.

I didn't need to blame the medical patch for this one though. I hadn't
masturbated in over a week and Lucy showed no interest in letting me
out of my cage. The new government issued device that Lucy had chosen
for me was "breathable and self-cleaning" so the only reason to let me
out would have been for sexual purposes. It was also bright pink, if
you were curious.

At first, I was determined to not bring up my sexual needs with her - I
didn't want to seem like the kind of barbaric male that she had avoided
purchasing - but the lack of release was driving me wild.

For one, Lucy was too beautiful not to notice and I spent most of my
time with her repressing thoughts about her body.

This became increasingly difficult as she became more comfortable
around me. At first I only set out her clothes for the next day, but
eventually she asked me to help her dress.

I'm not sure if she heard me gasp when she removed her bathrobe for the
first time. She had underwear on, still wet in spots where her hair
dripped onto it, but it was a shock to see so much of her skin all at
once.

She was truly gorgeous. Toned legs and a flat tummy, Sculpted
collarbones and dainty feet.

And every morning I saw these features up close as I helped her step
into her skirt, or buttoned her blouse.

I didn't even need to steal glances. I could stare all I wanted, though
my chastity cage ensured I was helpless in acting out any fantasies I
might have harbored.

By that time I had taken to sleeping on the floor next to her bed. She
seemed to prefer it, and although I would have slept better on the cot,
I enjoyed the feeling of watching over her. Or under her I suppose.

But a honeymoon can only last so long.

At some point I realized my chest had developed a definite curve to it.
A chest that bordered on breasts, and despite my newfound reluctance
for confrontation, I finally decided to put my foot down.

"Lucy, I think you may not have been perfectly candid with me. What's
in the patch, I've been wearing? I deserve to know."

I was proud of my professional tone and measured self-defense.

But she must have seen this coming because she didn't hesitate. "It's a
feminizing hormone and a complementary drug that maintains your
libido."

Smarty pants with the big words.

"So you're turning me into a horny woman? Shouldn't you have mentioned
this?"

"Taylor, I told you when we first met that I always wanted a little
sister to dress up. And you know about the maidservant program. I
thought you'd have a better handle on what's involved."

"Men are prevented from learning certain things," I replied with a
frown. "Is it permanent?" I asked after a pause.

I braced myself for an answer.

"No. It's not permanent."

She stepped toward me and gently slipped her hand under my bodice,
measuring the fullness of my swelling breasts and outlining my nipple
with her fingertip. I froze and shivered at her touch.

"You're progressing faster than I was told to expect. I didn't think
we'd be having this conversation for another month."

Instead of perturbed, she seemed satisfied with this development.

I ignored how good her hands felt on me and stuck to my original goal.
"Can we at least skip the libido drug? Or set up a regular release? I'm
really suffering."

"I don't want you to suffer," she started, "But I do think it's good
for you to struggle a little. You know I like that you got an erection
when you were losing that wrestling match. I want someone easily
aroused, and it's even better if you're aroused by a woman having her
way with you. Men need to be motivated. And I think that if your
orgasms are dangled just out of reach, you'll never get bored of me."

She saw my look of disappointment and continued.

"Why don't you take this as a time to experiment? Nobody you know is in
this city. Just enjoy being a new person for a bit. And there are
things to take pleasure in. I hear some men find the combination of
increased libido and having access to breasts to be exhilarating. When
you go to sleep at night, try playing with them. Explore a little.
Maybe you'll be grateful if we can get them one more size up."

I had almost taken Lucy for an asexual. Apparently not.

"You know, I really do care about you Taylor. But you also belong to
me. And this is how I want you to be for now."

I had wanted to ignore her suggestion to touch my growing chest. I felt
like a freak as it was, and didn't want to be aroused by my own body.

But now that the idea had been planted I lacked the willpower to oppose
it. That night, as soon as I heard Lucy fall asleep above me, I gently
ran my fingers over what I was finally admitting were my breasts.

My nipples were puffy and sensitive, and sat atop a mound of flesh that
could almost fill my hands. I kneaded them between my fingers and
gasped out loud.

It felt better than I expected. Much better.

I waited to hear Lucy's next breath and when I was content that she was
still sleeping I continued.

I very quickly realized I had boob envy.

34-C.

That was Lucy's bra size. I knew from washing her laundry. I'm pretty
sure mine were less than A cups. Wouldn't it be nice to grope something
more substantial?

As my cock throbbed in its cage in response to this thought, I rolled
around in frustration, toying with breasts that were now constantly
available to me, while sexual release was 'dangled out of reach'.

***

A few nights later Lucy had gone to bed early while I was still
cleaning in the kitchen.

"Taylor." I heard her call me with that quiet uncertain voice that I
found so charming.

I walked to her bedroom and opened the door. "What is it?"

"Would you mind doing me a favor?" she looked sheepish as she asked it.

"Of course," I said, expecting a late night snack request.

"Can you... take care of me?"

She pulled off the covers slowly to reveal that she was only wearing a
t-shirt and panties.

I gulped.

I stepped toward the bed as if in a dream.

She patted the sheet next to her. I lied down with my head propped on
my elbow.

"You want me to touch you? To give you some relief?"

She nodded, not even apologetic that she was requesting satisfaction
while denying it to me. For a woman, nothing could be more natural.

I rubbed my hands together to warm them, and gently placed them on her
thigh.

She sighed and seemed to relax.

"Thank you. I need this."

She closed her eyes and I took the opportunity to observe her beautiful
body. Her nipples tenting her t-shirt, her angelic face, the curve of
her legs.

I rubbed her thighs with my hands, and moved them across the flat skin
of her tummy, letting her grow accustomed to my touch.

"Taylor," she hesitated as if building up jer courage. "Could you say
nice things about me when you touch me?"

It was the most innocent request for dirty talk I had ever heard.

"Of course," I responded while I decided what approach to take.

"You are super, super cute Lucy. You're adorable but also really sexy."

She smiled and sort of squirmed as my hand passed close to her
underwear.

"I love dressing you each morning. I feel so grateful to even get to
look at your beautiful body. And you have the cutest upturned nose.
Sometimes it makes you look charming and timid, but when I'm on my
knees putting on your skirt and I look up at you, it makes you look
proud and royal. So far above me."

"Hmm, do I seem powerful to you? Like a queen? I like that."

I slowly moved my hand toward her groin and beneath her underwear. Her
skin was shaven smooth. I wondered if she had planned this moment when
she showered earlier.

Her whole body twitched and I marveled at her sensitivity. Was she a
virgin? I wondered.

"Of course you seem powerful to me. You're smart and beautiful and
you," I paused to consider the ways she had power over me, "you own my
cock."

When my fingers reached her slit they slid in easily, almost drawn
deeper by her desire. She clenched around me as if yo exert her
control.

"Fuck." She gasped. "Say it again."

Now I knew what she wanted.

"You own my cock. I can't cum because you won't let me. I can't even
touch myself. I'd do anything you want."

I pulled out of her and she groaned and grabbed my wrist, pushing my
fingers back inside.

"Do you like it? Do you like being owned?"

In and out. In and out. Slow circles and steady pressure.

"Yes. I don't want anyone else to control me. I'm glad it was you. I
get hard..." I had to correct myself, "My cock tries to get hard every
time I think about you controlling me. You're my gorgeous mistress. I
want to serve you. To do what you say. To wear what you want me to
wear."

"Hmm, you like that I make you dress like a girl," her voice was dreamy
and far away.

"I want you to control me. I want you to tell me what to do."

"Oh my God, keep going," she was squeezing both her breasts as I spoke
and her eyes were locked on mine.

"You own my cock. You deserve to own my cock." The words spilled out of
me. I told myself I just wanted to please her. To say what it took to
make her orgasm.

And her body did respond to my words - to my touch. It was like playing
familiar notes on a new instrument.

"I own your cock," her words were broken, barely audible between gasps.
"I own your cock. I own you."

Suddenly she cried out and began to cum. She grabbed my wrist with both
hands, holding me in place while she arched her back and spasmed.

I wanted to fuck her so badly. To swing my legs over her, pull out my
cock and show her how good I could make her feel with it.

But instead I just lay next to her, feeling the wetness of my pre-cum
as it slid out of my cage onto my leg.

As Lucy's breathing slowed she took on a restful, peaceful look.

I felt envious of her. Knowing how easily she would sleep while I
replayed this moment in my head, destined for fitful dreams.

As her breathing steadied she smiled languorously.

"Thank you, Taylor. I didn't know how badly I needed that."

It was like a fever had broken. She had been horny and needy and now
she was calm and satisfied, while I was still burning with desire.

I smiled back at her, wishing it hadn't ended so quickly.

I withdrew my hand from her panties and held it before me.

A thought crossed my sex-starved mind.

"May I... lick my fingers?" I asked her.

She wrinkled her nose and smiled. "Boys are so funny." She paused
thinking it over and I thought for sure that she would say no.

"Alright, go ahead and taste me you weirdo."

I didn't stop looking her in the eyes, but slipped my two fingers past
my lips.

I moaned.

I wanted so much more of her taste.

She giggled again.

"Okay. I think I'm ready to sleep. Why don't you go back down on the
floor, since you love looking up at me from down there."

I hoped that after that moment of intimacy I might have earned a night
next to her, but it turned out that was presumptuous of me.

The floor was to remain my bed.

***

The next morning I was pretending to remake Lucy's bed while she
prepared herself in front of the bathroom mirror.

She was in matching black lace panties and a bra and I was admiring the
concave and convex curves of her lower back and bottom. She was
considering herself from different angles turning this way and that and
even trying out slightly different facial expressions while she thought
I wasn't watching. Then she cupped her breasts under her bra and lifted
them slightly allowing them to drop into place and causing me to
completely stop what I was doing as I watched them jiggle ever so
briefly.

It occurred to me that maybe she was showing off. But then she frowned.
Staring at herself intently, she pinched the top of her ears and pinned
them back against the side of her head so that they no longer stood out
and once again considered herself from different angles. It startled me
to realize how someone so objectively beautiful could still be so
insecure.

***

I'm not sure if I unlocked something in Lucy that night when I touched
her. Perhaps just a realization of how good it can feel to have someone
else touch you. Or maybe she figured out how easy it was to get me to
do what she wanted. All she had to do was ask.

The next few times she asked me to touch her she bit her lip and
mischievously said something like "Taylor, could I borrow your hand for
a minute?"

But soon her oblique references became more bold.

One night I miraculously managed to fall asleep before she did, only to
be woken by a gentle nudge to my ribs.

Lucy was looking down at me from her bed, her feet dangling off the
edge with that same smirk as before.

"Yes mistress?" I asked.

She just looked between her legs and then looked back to me.

"Yes mistress," I repeated and got to work.

The next day I was cleaning the kitchen when Lucy hopped up on the
still wet counter next to me.

She was wearing a simple white tank top and dolphin shorts.

I was in the standard French maid outfit.

I admired the way the skin of her leg flattened where it rested on the
granite surface.

"So Taylor, do you remember that time you asked me if you could lick
your fingers?"

My mouth became dry almost instantly.

"Yes," I said, trying to anticipate where she was going.

"Did you like the taste?"

I nodded.

"And the reason you licked your fingers, it's because they were in my
pussy, right?"

"Yes," I replied breathlessly.

"So I guess that means you would like to lick me... down there? If I
let you."

"I would love to."

She scooted closer to me so her thigh touched my hand where it rested
on the tabletop.

"Do you sometimes think about doing that to me?"

"All the time." I answered truthfully.

"Oh yeah. Like how often," she prodded with that infectious smile.

"At least everyday. Maybe every time I see you even."

"Oh," she slapped my arm in feigned outrage. "You're such a naughty
girl," and she tugged on my crinoline skirt. "But seriously, if I let
you... would you lick me... everyday?"

"If that's what you wanted."

"But is that what you want?" she insisted.

"Yes. I want it." I sank to my knees in front of her, like a knight
vowing service. "Please let me lick your pussy."

She nodded greedily. "Show me how badly you want it."

Will You Ever Let Me Cum Again?

by TiltingatWindmills (UID 6248561)

https://www.literotica.com/s/will-you-ever-let-me-cum-again

Taylor is forced to become a sissified maid.

Page 3 of 3 page(s) (9777 characters)

She extended one foot for me to kiss. And i did, generously laying my
lips on her instep, and then her calf, working my way past her knee.

"Will it drive you mad, bringing me to orgasm every day with your mouth
while I give you nothing back?" she taunted playfully.

I continued kissing her, creeping up her thigh.

"Tell me that's what you want," her voice was suddenly imperious.

"Yes. I want you to keep me in my cage, I want you to deny me so I'm
always ready to please you, whenever you want it."

My brain couldn't believe what my mouth was saying. Surely she would
know I was just responding to her inside of a game?

"Fuck" she whispered, impressed by how tightly I was wrapped around her
finger.

She lifted herself up so that I could help pull off her shorts. She was
wearing one of her nicest red panties. She had planned this.

"Take them off too," she said curtly.

I did and stopped to admire her. Her flower blushed in front of me, a
beautiful pink that glistened with slickness. Her petals unfolded
before me and I almost immediately leaned in to lick her newly exposed
skin.

"Wait," she said and dangled a pair of keys in front of me. I had never
even seen them until this point.

"Unlock it," she glanced at my crotch. "I want to see it. I want to
know how much you love worshipping me."

I lifted my skirt and fumbled with the cage before figuring out the
lock and pulling my cock out in front of her. The cage sprang apart as
my member inflated rapidly.

"Fuck it's so small." She waited as twitch by twitch it finished
growing. "Is it done?"

I nodded.

"So small and so hard," she mused.

I knelt there, willing it to grow larger, but it had indeed shrunk
since it had last been allowed out.

"It's leaking isn't it? That's for me?"

"Yes," I confirmed as a strand of precum formed at the tip.

"Hmm, I love how pink and tight it looks for me."

I remained still and at attention, awaiting her command.

"Keep your hands here," she placed one of my hands on each of her
thighs. "I don't want you to be tempted to touch yourself. I'm the only
one who gets to cum in this household."

"Yes mistress."

This time I leaned in and was rewarded with my second taste of Lucy.

She squirmed when I licked her.

"Hmm that feels good."

I licked again, slow and deliberate.

"Oh I'm so happy watching your little man bob up and down while you
work for me. He's pointing straight at my pussy you know?"

I kept licking, basking in the humiliating way that Lucy described my
cock.

"I bet he thinks this is just a warmup and that he's going to get to
fuck me soon. Poor little thing. Maybe next time I'll leave him in his
nice warm home so I don't have to crush his expectations."

I moaned into her and she seemed to enjoy the vibrations.

She intertwined her fingers in my hair and then forcibly tilted my head
back. "Look me in the eyes when I use you," she said.

Her breath was ragged and each word came out slowly, and interspersed
with moans.

"I want you to watch my face when I cum and try and remember how good
it feels to orgasm."

I nodded. She was becoming really good at playing the mean mistress.

"You're watching?"

I nodded again.

She closed her eyes and I began trying in earnest to bring her to
completion.

"Oh God oh God oh God."

Her breasts heaved and her back arched.

I could tell she was enjoying this much more than my fingers.

My cock twitched in sympathy, up and down, trying to reenact the last
time it had been allowed to carry out its most important function while
Lucy screamed and shook above me.

***

I thought that maybe Lucy asking me to show her my cock was a stepping
stone to something better.

Perhaps she'd take an interest and let me out every so often.

But I think she really had just needed to confirm that I was aroused by
going down on her. Once that was out of the way she could use me
everyday and there was no need to unlock me again.

And so we focused on Lucy, and she learned to take what she wanted,
whenever she wanted it. Which turned out to be more than once a day.

A couple months into our arrangement Lucy began trusting me to handle
her calendar and her emails. I was instructed to never snoop on her,
but if I did encounter anything sensitive I should let her know what I
found and she wouldn't be angry.

At first very little came of this policy. I learned to respond to
messages in a straightforward way, saving her time and effort to focus
on other things. Eventually she had me responding to even personal text
messages, dictating her replies while she put on makeup and so forth.

One evening she was walking around the apartment, planning to go out
with friends she had made at work when I saw her phone flash.

"New message," I told her, suspecting she might want the update if it
was about her evening plans.

"Read it to me," she instructed in passing.

"It's from Amelia," I said.

"Oh she's the friend from back home who's moving here next month. Just
read it out loud I'm not in that much of a rush."

I opened the message and recited its contents.

"So how is the new maidservant treating you? Have you found his
services to be satisfactory?" I read out. "And then there's a devil's
face and a peach emoji."

We both laughed.

"Tell her that you have been very satisfactory in that regard and I
plan on keeping you around for some time."

I smiled inwardly and sent the message.

I watched as Amelia composed a response on her end.

"That's great. You deserve it!" I read aloud and then scanned ahead and
gulped before reading what came next. "So tell me, how often do you let
him out of his cage? I know you said it's small, but do you like
playing with it?" I let the words hang in the air. "Maybe you would
like to just respond yourself?" I offered.

"No that's fine," she said though she finished her makeup and walked
over towards me. "Tell her that I never let you cum. Say that I can
tell it's driving you absolutely crazy."

I typed in the message with sweaty palms.

Lucy sat next to me on the couch and we watched together as the little
ellipses formed while Amelia replied.

/So mean! Haha I love it. He must be slobbering over you by now. Don't
you feel a little bad though? Most keyholders would have let him cum a
few times by now./

Lucy laid her hand on my thigh and rubbed it gently.

"You're doing great," she said. "Tell her that I do feel guilty, but I
love how desperate it makes you so I just can't stop myself."

My breathing was heavy as she moved her hand up my thigh, under my
tulle skirt until her fingertips were just barely resting on my cage.

I finished writing.

"Good," she was leaning in and whispering into my ear, her tongue
flicking my skin as she spoke. "Now tell her that I can hear you
whimpering next to my bed when you think I've fallen asleep and I'm
pretty sure you hump your pillow every night."

I felt her fingernails delicately scrape my balls through the satin of
my panties as she spoke.

I entered the message with shaking hands, rewriting the same typo three
times before getting it right.

/Fuck, you're a bad girl. I guess maids just have to put up with it.
Are you one of those mistresses that makes him wear the outfits?/

"Tell her yes. Tell her I'm medicating you as well and that I'm
planning on making you dress like a girl everywhere you go. I just need
to train you to accept it first."

My cock twitched in my cage, betraying my unwanted arousal at her plan.

I typed out the message and waited.

/Fuck that's messed up. But also kind of hot./

"Tell her it makes me so wet controlling you. It's like you're my
little dress up doll. A plaything that lives to lick my pussy."

I typed and hit send.

The next message rolled in.

<j>I'm so fucking jealous. So, will you ever let him cum again?</i>

I stared at the phone, frozen.

I wasn't sure I was ready to hear the answer to this one.

"P-please Lucy." I stammered.

"Please what, my little doll?" she tightened her grip around my
testicles as she spoke.

"Please. I need to cum so badly. Please let me out of my cage."

I looked at her in the eyes with my best puppy dog stare.

"No," she said simply.

It was the sexiest thing I had ever heard in my life.

My cock twitched helplessly again, barely able to exert enough force to
move my cage.

Without breaking eye contact Lucy placed a hand on my shoulder and
pushed me down.

I knew what she wanted and slipped off the couch, sinking to my knees
in front of her.

She pulled her skirt up around her waist. There was a damp patch in the
center of her panties.

"Make mistress happy before her party dear," she instructed.

And I did.

Story Tags: cross%20dressing; forced%20feminization; sissification;
maid; femdom; female%20domination; denial; tease%20and%20denial;
chastity

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