My Landlady Had Different Plans - Part 2

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Note - This story is a work of fiction. All characters, names, and events are purely imaginary and bear no relation to real people, living or dead. Any resemblance is purely coincidental.

I took a deep breath to settle my nerves.

Mrs. Johnson and I were in my closet with soft cloths, brushes, and shoe polish. I looked around at all of the dresses, skirts, blouses, and uniforms hanging on the closet hangers, and then at the rows and rows of boxes and bins. All crammed with feminine clothes and finery. All of which I knew that Mrs. Johnson was hoping I would explore and wear.

"So many shoes!" I said once Mrs. Johnson had pulled down and opened all of the shoe boxes.

"Not that many," she tutted. "Maybe 70, 80 pairs or so. Here, put this on."

Mrs. Johnson handed me a long, lace-trimmed, Victorian-style maid's apron.

"Oh, I don't need--"

"Tutt tutt. I insist. No need to get shoe polish on your nice clothes. Now here," she slipped it over my neck, turned me around, and tied it in a big floppy bow behind my back.

"Now let’s get to it, shall we?"

The work went quickly. Most of the shoes had been lovingly cared for and were in quite good shape. Some of them had scuffs that we polished and all of them needed some level of dusting.

Occasionally, I would look at the scene we presented, as if from the outside. I was dressed in a Victorian maid's apron, sitting on the floor with my apron spread around me, at the feet of Mrs. Johnson, the lady of the house, who was on a bench inspecting the shoes and counseling me on the work that needed to be done.

It felt like a scene out of place for the modern era, a scene of domesticity plucked out of the early 1900s and transported to today.

"Excellent job!" Mrs. Johnson said, satisfied.

I smiled at her praise. It had been a pleasant afternoon after all.

"Now, are you sure that you don't want to try on a pair or two? With some stockings? Aren't you the least little bit curious?"

"Oh no, thank you, Ma'am," I said. She had been teasing me all afternoon about becoming more acquainted with the contents of the closet. "You're being very generous, but no, thank you."

"But why not?" she asked. "What is the harm in trying?"

"I, ah, I'm just not, ah, ready for it. Right now. I mean..."

"Oh, my dearest, I understand," Mrs. Johnson lifted me to my feet and pulled me into a warm hug. Her hand drifted to my bottom, which it gently cupped. "You take all the time that you need. Just knowing that someday you'll be ready is all that I need to know... for now."

Oh, great, I thought. Now she thinks that it's just a matter of time!

I looked at my watch.

"I, uh, guess it's time for me to go help Jessica," I said.

"Why of course! How the time flies when you're having fun," she said, pleased. "Uh, Paul?"

"Yes, Mrs. Johnson?"

"I think you may want to take off your apron?"

"Oh! Of course! Thank you."

"Look how easy you got used to it!" Mrs. Johnson teased. "I wonder what Jessica would think if you showed up at her door with a frilly apron on! Why, she might just make you her Lady's maid right then and there!"

"You showed up," Jessica said, sounding surprised. "Come in."

She led me up the narrow stairs of her townhouse and into her bedroom.

"Well, now we get to see if you learned your lesson." Jessica sat down on a chaise, leaving me standing before her.

I took a deep breath.

"Jessica, I wanted to say that I was very wrong to have lied to you. I should have admitted I was wearing panties right away rather than trying to hide it. I am truly sorry, and I will never do that again."

"That's very nice, Paul. Now take your shirt off."

"Take my...?"

"You heard me."

Slowly, I unbuttoned my shirt, revealing the bra underneath.

"Oh, Paul," Jessica said, shaking her head. "I can see that you haven't learned your lesson at all."

"What do you mean? I wore the bra just like you asked. I even slept in it."

"You slept in it?" she giggled. "That's great. But in the future, you should just wear a nightgown to bed instead of the bra."

"Jessica, please," I whined. "What did I do wrong?"

"I can't tell you that," she said, frustratingly. "You have to figure it out on your own. But I will tell you that I am disappointed with all that chest hair. Raise your arms. Ugh! And all that underarm hair. Alright, I think we need to continue your punishment for another week."

"Another week!" I took a step back and crossed my arms over my chest.

"Yes, I want you to wear a bra for another week. AND I want you to wear stockings and a garter belt as well."

"No!" I shouted, panicked. "I can't!"

"You can't?" Jessica asked, quizzically.

"I can't. I have to work! People will notice! Your mother will notice! Please..." I whimpered, "Didn't I do everything you asked me? Why do I have to wear it another week?"

"Well, first off, no one is going to notice. Okay? Dad wore a bra, panties, stockings, and garters to work every day of his life since he met Mom, and no one noticed."

"Are you serious?" I asked, astonished.

"Yes. And believe you me, I should know."

"But how did you--"

"Never mind that. Second, in terms of 'why, ' the simple answer is 'because I said so.' You have to be taught a lesson in how to behave, and I am the one to teach you that lesson."

"But what am I going to do about your mother? There's no way I can go a week without her noticing!"

"Well, there's an easy solution to that."

Jessica just looked at me.

"What?" I asked, confused.

"Actually, now that I think about it, there are two easy solutions."

"What are they?"

"Do you want my help?" she asked.

"Yes! Please."

"Are you sure?"

I hesitated. What did she mean by that?

"Uh, yes. I think so? Yes, Jessica, please help me."

"Alright then. Take your shirt all the way off. Now take off your shoes and pants."

I did as instructed, placing all of my male clothes on the bed. I felt worse than naked, with me in bra and panties and her fully dressed before me.

"Now come here and sit." I sat on the chaise, where Jessica pulled me into a hug from behind and kissed me on the ear.

"Hello? Jessica?"

That was Mrs. Johnson! On Jessica's cell phone!

"Hey, Mom. I'm here with Paul. Did you know he's been wearing a bra?"

WHAT?? I struggled to get up, but Jessica held me firm.

"Is that so? How wonderful! I suspected something was up, Paul, are you there?"

"Y-yes, Mrs. Johnson," I said, freaking out. Oh, god, I thought. Now my landlady knows I'm wearing her husband's bras. Oh shit.

See, problem solved, Jessica whispered into my ear. Her hand moved up and began stroking my nipples in the bra as I squirmed in her arms.

"I'm so happy, Paul!" Mrs. Johnson enthused. "My husband had such pretty bras, I'm so happy you've decided to wear them. I hope you'll be wearing them from now on."

From now on?? What the fuck??

"No, it's just for a week," Jessica jumped in before I could say anything. "Just to see."

Thank you, I mouthed to her, grateful.

"Oh, Paul, that is very practical," said Mrs. Johnson. "But I'm just sure that you'll love wearing bras so much that you'll want to wear them forever. I'm sure of it."

Oh god, no.

"And Mom," Jessica continued, "Paul also confessed to me that he wants to wear stockings and garters as well!"

"Really?" The sound of delight in her voice was almost too much. "Is that so, Paul?"

Say yes, dearie, Jessica whispered into my ear. You know you have to.

"I,"

Jessica pinched my nipple.

"Yes," I said, spurred into action. "Uh, for this week only."

"Well, that's just wonderful! Bras, panties, and stockings. It's the girlish trifecta. Is there any way I can help out?"

"I'm so glad you asked!" Jessica said. "Paul needs help with hair removal!"

Jessica!! I looked at her, shocked.

"Oh, Paul, I can most definitely help with that!" said Mrs. Johnson, sounding motherly. "I know all of the products and techniques you'll need. Of course, it will take sometime  to get used to the daily regimen, but I can help with that too."

Help with my daily regimen? What does that mean?

"And Mom? Paul also expressed some concern about what panties and bras, and stockings he should wear every day."

Uh, oh. I felt prickles run over my skin.

"Is that so?" Mrs. Johnson asked, seemingly surprised.

"You know, what goes with what, and what looks good together," Jessica continued. "And so he would like for you to choose all his underwear, every day this week."

No!! I struggled again to get away, but Jessica held me firm.

"Goodness!" said Mrs. Johnson, surprised. "I, I..." she seemed at a loss for words. "That would be just like... Is this true, Paul? Do you really want me to choose what underwear you will wear?"

Jessica hit the 'mute' button on her cell phone.

"Say yes," she told me. "Say yes, and I promise you that after this week, your punishment will be over. You can wear what you want and I will never again pressure you to wear women's clothing again. I promise."

"Hello?" Mrs. Johnson asked over the cell phone. "Is anyone there?"

"Sorry, Mom," Janice said, unmuting the phone, "Paul is just being shy."

"Mrs. Johnson," I said. "Surely you have better things to do than pick out my underwear every day!"

"Now, no need to be shy, Paul," Mrs. Johnson said. "I picked out my husband's underwear every day, for over 25 years, so it's no trouble at all."

"It is just like Dad, isn't it..." said Jessica. Suddenly, she looked at me, her eyes thoughtful, as if new insights were dawning.

"Yes, it is," said Mrs. Johnson. "Just like Francis, my late husband, god rest his soul. As I said before, Paul, you really are doing me the most wonderful favor. Seeing these pretty clothes get used again -- it warms my heart."

"Oh... ah... you're welcome, Mrs. Johnson," I said, feeling trapped and defeated. Apparently, there was no way I would be getting out of having my underwear chosen by Mrs. Johnson.

"Thank you, Mom! You're the best," said Janice, grinning wickedly at me as she hung up the phone.

'It's only a week, it's only a week,' I kept telling myself.

Dinner was over, and I had finished the dishes (in the fancy Victorian maid's apron, somehow it had made its way downstairs, and Mrs. Johnson insisted I wear it).

"Shall we go upstairs and get started?" Mrs. Johnson looked at me with a twinkle in her eye.

"Oh, okay," I responded, my stomach knotting up. I followed her upstairs.

We first went to the bathroom, where Mrs. Johnson went over all of the details on hair removal and skin care. I was to use a blade for my underarms and legs, and depilatory cream for everything else. There were extra steps for shaving, cleaning, and moisturizing my face.

"Everything clear?" she asked. "Good. You'll need to shave your face, legs, and underarms every day and use the depilatory twice a week from now on. Why don't you go ahead and do the first treatment now, and I'll go pick you out some pretty dainties for you to wear?"

"Okay," I said, with a slight tremble in my voice. "Thank you, Mrs. Johnson," I added, grateful that she had treated the whole experience with tact.

"You're so welcome, Paul."

When I got back to my bedroom (wearing just a robe, my skin pink, sensitive, and hair-free), I found a simple pair of nude-colored high-waisted panties, a beautiful bra with simple lacy trim, and a pair of white stockings with a white, lacy garter belt.

Oh god. I sat on the bed, hyperventilating. My landlady had picked out my underwear, and here it was, waiting for me to put it on. She would know what I was wearing underneath. The most intimate clothes, those that covered and caressed my most intimate places - I no longer had a say in what they would be. They would be chosen for me to wear by my landlady, Mrs. Johnson.

I removed the robe and slowly dressed in the underwear set out by Mrs. Johnson.

'Mrs. Johnson chose these panties for me to wear,' the thought raced through my head as I put them on. "Mrs. Johnson chose this bra for me to wear.' As I put on each piece, I felt tingling and prickling in equal measure all over.

Why was I so hard? I adjusted my penis in the panties, breathing hard. After a while, I got my passions under control, finished dressing in my male clothes, and went back downstairs, where I heard the TV.

"Everything go okay?" Mrs. Johnson asked.

"Yes, no problems," I said. For some reason, I couldn't look her in the eye.

"Excellent. Now, come over here and sit down and let's check the fit on that bra."

"The... fit?" I asked.

"Of course. We need to make sure the straps are right."

"I'm sure it doesn't need..." I started.

"Oh hush, don't be embarrassed."

She unbuttoned my shirt, all but the last two buttons, and then slipped it over my shoulders, revealing my chest encased in the bra. I looked away, blushing bright red, at showing my bra to my landlady.

"There now, see? This isn't nearly tight enough," she said, adjusting the straps. The light touch of her fingers on my skin made me quiver. Once adjusted, Mrs. Johnson tested the straps and tugged the cups flat against my chest.

"Perfect," she said softly, almost to herself. For a second, her hands drifted down to my nipples, lightly tweaking them.

I sucked in my breath. My nipples had always been super sensitive, and to feel them caressed through the satin fabric of the bra... it was almost too much.

"Now let's check the stockings."

"S-s-stockings?" I stammered.

"Yes, of course. Let's see how well you did putting the stockings on, and adjust the garters."

"I."

"Come, dear, stand up. This will only take a second."

Slowl,y I rose to my feet and was about to object again, but Mrs. Johnson had already unbuckled my pants. Soon she had them down at my ankles. I covered my crotch.

"There now, see?" she asked, seemingly indifferent to the hard bulge I was hiding. 

"These are much too long. Let's tighten them up, shall we?"

Mrs. Johns tightened up all of the garters, reducing each strap by half. The belt hugged low and tight on my hips.

"Much better," she sighed, tracing a finger around the stocking tops, giving me goose bumps. "Now, what shall we watch on TV?"

Head still reeling from the 'inspection', I pulled up my pants and buttoned up my shirt and joined Mrs. Johnson on the love seat. Other than a smile, she acted as if nothing were different.

Just another relaxing evening watching TV.

After the show was finished, Mrs. Johnson stood up to go to bed.

"Would you mind so terribly giving an old lady a goodnight kiss and hug?" she asked.

"You're not an old lady," I protested, standing up.

"That's nice of you to say," she said, her lips on my cheek as we hugged. I squirmed as my penis hardened. Could she feel it? Like before, she gently kissed me several times, but stopped just short of my lips, leaving me sighing and frustrated.

"Feel free to keep watching TV," she said. "And sleep tight."

I stayed up for another hour or so before heading up to bed. When I got there, I got yet another surprise.

There, lying on the bed, was a nightgown for me to wear. It was long (below the knee), made of actual silk, dusty rose in color, with lace trim around the edges, and oh so feminine.

And there, right next to it, was a new, white hand-towel.

I must have stood there for 5 minutes, taking shallow breaths, frozen and unable to decide what to do. I reached out, but then pulled my hand back, perhaps afraid of what would happen if I actually touched it.

Obviously, she had meant for me to wear it to bed. When I had agreed to wear panties and a bra (and stockings!) I had never thought it would extend to this.

I slowly stripped out of my male clothes and stood in nothing but bra, stockings, and panties.

What had Jessica said? That I should sleep in a nightgown instead of a bra at night. Had she discussed this with Mrs. Johnson?

My face burned at the thought of the two of them discussing with each other what I should wear to bed.

'It would be nice not to have to wear the bra all night,' I thought to myself. 'And it's only in bed, while I'm alone. No one else will ever know.'

I took off my bra, garter, and stockings and, after another hesitation, picked up the nightgown.

Oh,

It slipped down over my body, caressing me with a light touch that gave me goose bumps. I fingered the lace hem and then ran my hands down the length of it, feeling the fabric over my body.

I moved the bed cover aside and moved to get into bed, trying my best not to bunch or twist the fabric.

I then reached for the hand towel.

The next morning, Mrs. Johnson chose my underwear while I was in the shower. When I returned from the bathroom, freshly shaved and moisturized, there they were, on my bed - waiting for me.

The panties and bra were cream with satin trim.

The garter belt matched in color and was trimmed in satin as well. The stockings were simple, sheer, and luscious.

'What is wrong with me?' I thought, looking at myself in the mirror. 'What am I doing, going to work like this?'

I felt jittery and twitchy as I got dressed.

'And why am I so horny all the time?' I muttered, buttoning my pants over my hard-on, encased in the nylon panties.