My Landlady Had Different Plans - Part 5

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"Well, aren't you just the picture of domesticity!" said Jessica, striding into my room unannounced.

"Jessica!" I said, startled. "Don't you knock?"

It was late Saturday afternoon, just the day after I had put on my first dress, and I was sitting on the bed surrounded by piles of clothes that needed mending. I was wearing another cute housedress with a fun print of multi-colored pears that just screamed 'housewife'. Mrs. Johnson had picked it out for me, of course.

"Mom said you were now wearing dresses, and I had to see for myself. What are you doing?"

"I, I'm doing some small repairs," I said. "Mrs. Johnson… your mom, is… uh… teaching me how to sew. And I'm starting with hand sewing."

"Wait, are these my old clothes?" Jessica asked.

"Yes," I admitted, blushing three shades of red. "Your mom said that if you didn't want them anymore, then I could have them, once they're repaired, or we could give them to charity."

It had been strange, working all day on Jessica's old clothes. I felt closer to her, somehow, seeing what she used to wear, replacing a button here and there, tacking back some loose lace, restoring a hem, repairing a tear, replacing a zipper. Every now and then, I had to go to Mrs. Johnson to get her advice, and she would show me exactly what to do.

"You're welcome to them," Jessica said. "I don't want them anymore."

"Are you sure?" I asked. "What about this T-shirt from when you were captain of the soccer team?"

Jessica examined it.

"Oh, okay. Maybe I should keep that. But Paul, what in the world are you doing?"

"It's Melissa, now," I said, staring down at the floor, feeling a hot flush.

"Melissa?" she gasped. "Are you kidding me? Paul, Really?"

"Please," I said, trying to be as firm as I could. "I'm Melissa now."

"Okay, fine. Melissa then," she rolled her eyes. "That doesn't change anything. What are you doing, repairing my old clothes? Aren't you the renter here? Shouldn't you be doing what you want to do, and not what my mother, your landlady, wants you to do?"

"Well, your mother thought it would be proper for me to learn to sew. And your old things needed some repairs."

"But Paul, Sorry, Melissa! Didn't I make it clear that you don't need to do this? All you need to do is 'Man Up', say 'Enough is Enough!' and stop all this nonsense. I know my mother! If you don't set boundaries and really stick with them, she'll run roughshod all over you!"

"But Jessica," I said, "it's okay. It really is. I like your mother. She's nice to me. I don't mind helping her around the house." I spread my hands to indicate the clothes around me, "and I like learning how to sew."

Jessica rolled her eyes. "You're as bad as Dad was, wearing what she tells you to wear, doing what she tells you to do. It's weak and pathetic."

"Is it weak and pathetic to love someone?" I said the words without thinking.

"How dare you!" Jessica yelled, flashing with anger. "You know nothing about what my parents were like!"

"I know that your mother loved your father," I said, trying to hold my ground. "She loved him desperately."

"She didn't love him. She used him."

"Maybe he wanted to be used by her?"

Jessica slapped me hard across the face.

"Don't you dare talk about my father like that!" she shouted, hot with anger. Jessica reached out as if to hit me again, but instead just stalked out of the room and slammed the door so hard that it rattled the perfume bottles on the dressing table.

"Melissa?"

The door opened, and Jessica peeked inside.

"Jessica!" I said, So glad to see her. I had freaked out after she left, certain that I had ruined any chance with her. The relief at seeing her back was intense. "I'm so sorry! I spoke out of turn, I didn't mean."

"Shush," Jessica interrupted me and came into the room. For some reason, she was carrying my old suitcase and placed it down by the dresser before coming over to join me. I scooted the clothes on the bed to one side so she would have a place to sit.

"I'm the one who should be sorry, losing my temper like that," she said, holding my hands in hers. "As you can tell, my feelings about my Dad are still quite raw. I looked up to him. He was my idol."

"From what I've heard, he was an amazing businessman."

"I know! He was everything I've always wanted to be! And that's why I have a hard time understanding how he could be so…" she paused, considering her words. "I mean, I have a hard time correlating his business life with his personal relationship with my mother," she finished diplomatically.

"I, maybe he," but I stopped myself. Now was no time to say something controversial. It was clear that Jessica was going to have to come to her own understanding. "It's clear he was a complex person," I said instead.

"You're telling me," Jessica said, with a snort. "But look at you! Don't you look so cute in that dress! It really suits you."

I blushed and murmured a soft 'thank you'.

"And is this what Mom is making you wear?" She got up and walked over to the closet and fingered the dark-blue A-line dress with the colorful collar.

"Yes," I said. "It," I gulped. "It's the dress I'm supposed to wear to work. But only when I'm ready."

"Wow! That's a big commitment. Are you ready for such a commitment?"

"I don't know," I admitted.

"And the handbag and the shoes! You'll be the best-dressed intern this town has ever had."

"I suppose."

"But it's really not that much of a commitment, is it?" Jessica asked, coming back to the bed to sit next to me.

I looked into her eyes. "What do you mean?" I asked, suddenly worried.

"Well, I mean that you still have all your male clothes, don't you? You could just decide to stop being Melissa and go back to being Paul at any time. Couldn't you?"

"Oh, I wouldn't… I mean, I don't think that…"

"Really? You sound a little unsure of yourself there, Melissa. Here, maybe I can help you make up your mind?"

"Jessica, please,"

"I know what Mom told you. She said that if you put on the dress, you have to call the museum director and tell him that you're transitioning to female full-time, isn't that correct?"

"Yes,"

"Well then, I want to oomph up the instructions a bit, okay? First, you must not touch the dress," she said. Jessica hugged me from behind and pulled me in close, her head on my shoulder, her lips by my ear.

"I must not touch the dress," I murmured.

"No, because if you do, then you will need to call your museum director and tell him that you are transitioning to being a woman full-time. Is that correct?"

"Yes, Jessica," I said.

"Very good. And Mom told you to choose some nice underwear and pantyhose, correct?"

"That's right."

"Ooh! I just thought of something. Let's get you started on corset training!"

"C-corset training?" I stammered.

"Yes, let's!" Jessica hopped up and went to the dresser, and opened the third drawer, which contained the shapewear. "Oh, I so like this one," she said, holding up an antique-white brocade satin corset with laces up the back.

"But I think it may be a bit too much to wear to work. How about for weekends?"

"Weekends?" my voice came out as a squeak.

"Sure, weekends! Once you touch the work dress, and then you transition full-time, I want you to go to my mother and tell her that you want to wear corsets to get a more womanly, hourglass figure. And you must tell her that this is all your idea. Do you understand?"

"I understand," I said, humbly. "But no one wears corsets anymore, do they?"

"Are you kidding me? Do you know Kim Kardashian? She's wearing them during workouts! Waist training and corsets are all the rage right now."

"Oh, I didn't know that."

"You'll be right at the cutting edge," she continued. "But that's not the real reason why I want you to wear corsets. Do you know why I want you to wear corsets?"

"No, why?"

"Because I want you to feel the control she has over you. It will be as if my mother is personally squeezing your waist down to girlish proportions. It's a physical symbol, a symbol of how she is reshaping you, both mentally and physically. Now do you understand?"

"Oh…" I said, suddenly breathing hard. "Yes, Jessica. I understand." But it's not Mrs. Johnson who is telling me to do this, I thought to myself. It's you, Jessica. You are the one demanding that I wear a corset. It's you who is reshaping my body.

"And, once you decide to transition full-time," Jessica continued, "once you put on that dress for work, I want you to wear corsets or waist cinchers every day. From now on, for the rest of your life. I realize it's not practical to wear them 24x7, but you must put on a corset every day and wear it as much as possible. Is all that clear?"

"Yes. Very clear." I said, squirming in my seat. Could I really do this? Could I really wear a corset every day? At least Jessica wasn't making me wear it while sleeping! I felt thankful for that, at least.

"Okay, let's see if we can find something more practical and more modern for when you go to work. Oh, hey, this one is cute!" Jessica held out a bright-pink neoprene and rubber waist training corset with no laces and three rows of hooks up the front.

"This is perfect! Just the sort of corset a young, aspiring intern at a museum might wear to work. I love it. I might go out and get my own."

I inspected the tag. It was a "sport" waist cinch (I learned later that it was not a 'proper corset', but so what), and it did look a lot less intimidating. Okay, I thought to myself, maybe I can do this.

But still, wear a corset or waist cinch every day?

"Every day for the rest of your life," said Jessica, somehow understanding the words that were running through my head. "Are you beginning to understand what you're getting yourself into?"

"I think so," I said.

"I doubt it. But I do have a couple more things for you."

"There's more?"

"Yes, of course there's more! See the suitcase over there? Isn't that your suitcase? The one you brought here as a renter when you moved in? Well, since you are no longer Paul, I don't think you'll be needing Paul's old suitcase anymore, now will you?"

"I… I… I don't know."

"Let me make this clearer. The suitcase is a symbol. It is a symbol that you are a guest, a renter. But once you touch that dress," Jessica pointed again to the dark blue work dress hanging on the closet door, "your status will change. You will no longer be a guest. You will no longer be a renter."

"No?" I squeaked.

"No," she said. "I've talked this over with Mom, and we both agree. Once you touch that dress, once you agree to transition full-time, you will become family."

"Family," I repeated softly.

"Yes, family. We'll be sisters, you and me."

"Sisters?" But oh no! I thought to myself. I'm supposed to be your wife, not your sister! This is not going in the right direction!

"And as my sister," she continued, "this will no longer be a guest room, it will be your room. And that closet is no longer a guest closet, it is your closet."

"My room. My closet." I looked around the room, which now looked completely different to me. Would this room, with its white gold-trimmed French provincial furniture and four-poster canopy bed with lace and tulle drapes, this would be my room? And the closet, jammed packed with ultra-feminine clothes of all types and descriptions, would become my closet?

"And because you now have your own room, your own closet, full of clothes, you will no longer need any of your old male clothing."

"No!" I gasped.

"Oh yes. I asked Mom for all your male briefs, and they are already inside the suitcase. Wasn't that nice of me? And so here are your further instructions. Once you've touched your work dress and have committed to transitioning full time and wearing dresses all the time, and once you've put on your corset and you are fully dressed and ready for work, I want you to take all of your old male clothes from the drawers and pack them in the suitcase with your old male underwear. You must pack away any and all scraps of male clothing you have. All of your socks, underwear, undershirts, shirts, pants, everything. Do you understand?"

"I understand, but" I tried to object, but Jessica was on a roll.

"Good. And then, on your way to work, ask Mom to stop by the local charity and drop off the suitcase with all of the clothes at the donation center."

"Are you kidding me?? Really? Do I have to?"

"Yes, you have to! And just imagine what this will mean? Imagine coming home after work? Imagine stepping in the front door, knowing that the only clothes you can wear are women's clothes? Is that the only underwear you can wear is lingerie? Can you imagine, from that moment on, you will have to dress as a woman? You will have no option."

"Oh, Jessica!"

"And don't think that you'll find any of my Dad's male clothes in the house. Mom got rid of those a long time ago. 'That's not how I want to remember him,' she told me. 

And so she only kept his female clothes, and now they're yours, and now they will be the only clothes in this world which are available for you to wear, and you will have to wear them, from now on, every minute of the day and night, no matter where you go or what you do. 

Panties, bras, dresses, corsets, two-piece swimsuits, stockings dressing as a woman twenty-four hours a day, seven days a week, three hundred and sixty-five days a year with no hope of going back, forever."

"Jessica, please!" I cried. "Stop! Why are you doing this?"

"Because!" She said, jumping up and turning to face me. "Don't you see? I'm trying to make you understand what you're doing! 

First it's panties and nightgowns, then dresses, and then you're Mom's girl for life, trapped and forever living to her standards and her rules! It's a one-way trip! I'm just trying to make you really understand where you're headed, and where you'll end up!"

I just looked at her, not knowing what to do. I felt a sinking feeling in my stomach, like I was slipping downhill, unable to control my fall, and Jessica was there, greasing the path.

"But that's not all," she said.

"Please, haven't you done enough?" I asked, my voice pleading for mercy.

"Not quite," she said, this time softly.

Jessica hesitated before reaching into her pocket and pulling out a velvet box.

"It's not what you think," Jessica rushed to say, hearing me gasp. She opened the box and revealed an antique Tiffany watch.

"Oh, it's beautiful," I said.

"Dad gave it to me," Jessica said, wistfully.

"What? I don't understand."

"Here's what will happen, Melissa, if you touch that dress. First, you will have to put on a practical pair of panties and a bra. Then you will need to put on a corset for waist training. 

Okay? Then pantyhose, and then the dress. And then once you are all ready for work, you will pack up all of your former male clothes into your suitcase, and then, right before you leave your bedroom, you will put on this watch. And once you put on this watch, it will be your watch, but be careful, because it comes with a heavy responsibility."

"R-Responsibility?"

"My Dad gave me this watch on his deathbed. He said, 'Jessica, I want you to have this watch, it's a gift from me. You know that I won't be around for much longer, and I want you to promise me that you will look after your Mother for me.'"

"Oh, Jessica! I can't possibly accept this!"

"But you have to!" she said fiercely. "If you put on the dress, then you must transition full-time, and if you transition full-time, then you must put on this watch. And if you put on this watch, then you must accept that you will forever be responsible for my mother's well-being. That you will watch over her and keep her company and 'be there' for her, at all times, forever."

"Forever?"

"Forever. Now do you understand? Now do you see where your dalliance with panties and bras and dressing up is leading? This is what my mother wants, she wants you to be hers… forever. You will become family. You will be the daughter she always wanted, obedient, attentive, compliant, adoring. 

You will be the daughter I never could be. And that's what it means to wear the watch. That is the symbolism of the watch, and that's why you must put it on, so that you fully realize what you're getting yourself into, so that you understand the full scope of your responsibilities."

"Oh, Jessica," I moaned, not knowing what to say. "I can't," I protested.

Jessica pushed me back onto the bed and climbed on top of me. We were surrounded by mounds of her old bras, panties, T-shirts, shorts, and skirts. She grasped my wrists and pinned them to the bed, and lay her body on top of me, her breasts pressing into my chest, her knee working its way up between my legs and pushing up against my swollen member. I closed my eyes and turned away, struggling to escape.

"Melissa," she said, nibbling my ear, "look at me."

"No," I said.

She grasped my wrists tighter and pulled them up over my head, and pressed her knee against my crotch. How could she be so strong? I felt weak and powerless beneath her.

"Look at me!" she commanded.

With pursed lips and what I hoped was a defiant expression, I turned my head to look at her.

"What?" I asked.

"Promise me!"

"No!"

"You must! Promise me that if you put on that work dress, you will wear corsets, take all of your male clothes to charity, and put on the watch. Promise me!"

"It's too much!" I wailed. "I can't. You are asking me to make a decision about the rest of my life! It's forever! I can't promise that!"

"Ahhh! So now you finally understand," she crowed. "That is exactly my mother's plan for you, I know it! This is your last chance. If you decide to put on that work dress, then that is another step down the path. 

Then you will give in to her next demand, and then the next, and then the next, and then, before you know it, you'll be stuck here forever. You will forever have her choosing your clothes and dressing you as her girl. This room will be your permanent home. Now promise me."

"No…" I moaned.

"I'm not telling you to put on the corset and the watch right this moment. It is a conditional promise. 

If you put on the work dress, then you must tell your boss that you will be female full-time, and only then must you wear corsets… forever, and give your suitcase and all your male clothes to charity, and put on the watch and wear it… forever. Now promise!"

"Please," I said, still struggling. "Please, Jessica! I'm not ready…"

And then she kissed me.

"Oh…" I sighed, kissing her back. Her lips were warm and moist and urgent.

"Promise me," she breathed. "I can feel that you want to," she added, pressing her leg against my hard member. She could tell I was giving in. "Now do it."

What struggle I had left had been eliminated with the kiss. If this is what Jessica wanted, then I would give it to her.

"I, I… I promise," I said, feeling my utter defeat.

"Again!" she demanded. Jessica pressed down, her legs straddling my hip bone as she looked into my eyes, her face flushed.

What the heck was going on? I felt Jessica press her crotch hard into me.

"I promise!" I said, more clearly this time.

As if it were a reward, Jessica kissed me again, this time with her tongue probing into my mouth. I just lay underneath her and let her have her way with me.

"What do you promise?" she growled, her voice growing husky. She was rubbing more urgently now, pressing harder.

"I promise, oh…" I gasped. Her leg continued to press into my member as she thrust against me. "I promise that when."

"WHEN??" she said, eyes wide with wicked delight.

"I mean IF! Shit! That IF I touch the work dress, I will wear practical working-girl underwear, and pantyhose," I stopped.

"Corsets!" She said. "Promise me you'll wear corsets!"

"Please…" I pleaded.

"Promise!"

"I…. I-I promise," I said, finally. "I promise to wear corsets."

"Every day! Forever!" Her thrusting against me continued, more rhythmically now.

"Yes! I promise to wear corsets every day, forever!" I said.

"Yes, that's right," Jessica panted, giving me another kiss, rubbing against me. "Now the clothes. Your male clothes. Promise me."

"I promise to gather up all my male clothes and donate them to charity, with the suitcase."

"And so you'll have to wear women's clothing… forever," she demanded. "You'll be a woman, forever." Jessica was breathing heavy now, her pupils dilated, and with a fine layer of sweat on her brow.

"Yes," I looked Jessica straight in the eyes. "I promise that I'll be a woman, forever."

"And the watch!" She was almost gone now.

"Yes, and the watch. I promise. I promise you! The clothes, the corsets, the transition, the suitcase, the watch, everything!"

"Oh, Melissa!" Jessica moaned, then she scrunched up her eyes, bit her lip, and pressed hard against my hip, quivering, her leg in my crotch against my achingly hard penis. "Oh shit! SHIT! Oh GOD!"

And then she orgasmed, right there on top of me, twitching and groaning. She pressed so hard I was sure I would be bruised in the morning. And as pleasure flowed through her, she lay her entire weight against my body, pressing me into the bed, clutching and rubbing, clenching and sighing.

"Holy cow!" Jessica panted, satisfied. "That was unexpected!" Jessica pushed more of her old clothes aside and lay next to me with an arm over my stomach, catching her breath. Her face was lightly pressed against my ear, and I could feel her hot breath against my cheek. I closed my eyes and just took a moment to enjoy her body next to me.

"I can already tell you're going to do it," Jessica said.

"Do what?"

"Touch the dress. Transition full-time."

I felt a knot form in my stomach.

"I… I don't know," I said.

"Psh," she snorted. "You may not know, but I know. You're going to do it. It's just a matter of time." Jessica began to undo the buttons on my dress, starting at the neckline.

"Hey! What are you doing?"

"Nothing," she said, as she pealed open the bodice and slipped a hand inside.

"Oh…!" I gasped as her fingers found my nipples in the nylon bra and started tweaking them. "What are you doing?" I repeated.

"Do you like my mother?" Jessica asked, ignoring me.

"Y-yes," I said.

"How much?"

"Very much. She's… she's a wonderful lady."

"I'm so glad to hear you say that. Do you think you'd like to be her daughter?"

"Her daughter?" I repeated, stupidly. "But you're her daughter!"

"It is physically possible for one mother to have two daughters," Jessica laughed. "But let me change my question. Do you think you'd like to be her adopted daughter?"

I thought seriously about her question, which was difficult because Jessica's fingers on my nipples were making me horny and distracted. "Yes," I said finally. "That would be… wonderful," I admitted.

"Then we would be sisters, and we'd spend so much more time together. Wouldn't that be nice? Would you like to become my adopted sister?" Jessica pulled her hand from out of my bodice and then gently traced her fingers down my body.

"Yes," I said, gasping. "I would like that very much." But I'm not supposed to be your adopted sister! I thought to myself, starting to worry. I'm supposed to be your wife… aren't I?

"I'm so glad," Jessica purred. "And now for your reward." Her hand reached underneath my skirts, where it began to caress me through the panties.

"But Jessica," I asked, squirming in her arms, "why do you want me to be your sister? Why is this so important to you?"

"Because I need a sister," she responded, softly stroking my hard penis. "My mother is here all alone. I was so glad she agreed to take on a renter, so there would be someone in the house to help look after her. But a sister would be so much better! A sister would be family. A sister would care as much as I do. I could count on a sister to help take care of her through thick and thin."

Jessica was now stroking my penis through the nylon panties in earnest, causing me to moan and whimper.

"And so I ask you again, do you want to become a family member? Do you want to become Mom's new adopted daughter?"

"I…"

"Shhh, you don't need to answer," her voice became more urgent. "Instead, I want a promise."

"A promise?" my voice cracked.

"Yes, a promise. I want you to promise me that if you touch the work dress, you will put it on. And that if you put it on, you will transition full time, wear corsets, and take all of your old male clothes to Goodwill, and…"

Jessica sought out my lips with hers and gave me a long, probing, wet kiss.

"Oh, Jessica," I sighed.

"And promise me you will go to Mom and ask to become her adopted daughter."

"Oh, gosh," I said. "I… I…"

"Here, let me help you," Jessica said, pressing her body against mine and stroking more urgently.

"Please… Jessica," I moaned, weakly struggling to maintain my control.

"Promise me," she whispered. "Say the words."

My mind was a fog of clothes and female smells and wet lips and urgent desire. Here I was, a shy 20-year-old, lying in bed nestled in mounds of a teenage girl's used clothing, in the arms of that teenager's older, more mature 28-year-old version of herself, a dominant woman who knew exactly how to control me to get what she wanted. Her fingers seemed to know exactly what to do, where to touch, and how hard to press to bring me right to the edge. I knew what she wanted me to say. And I desperately wanted to give it to her.

"I promise," I said.

"What do you promise?" Jessica kept stroking and held me tight.

"I… I promise to ask Mrs. Johnson to adopt her adopted daughter. I want to. I want to be part of your family."

"That's my girl," Jessica said. "That's my darling Melissa. Now let go. Let it happen. Come for me."

"Oh, Jessica!" I cried out as my passions overflowed into my panties.

"Call me Jess," she said softly, as I gasped and jerked in pleasure and buried my face into her shoulder. Tears sprang to my eyes, and I began to cry softly.

"I always wanted a sister who would call me Jess," she added, holding me gently.

Later that night, Jessica was at home, alone in bed, trying to do some work on her laptop when her cell phone rang.

"Hey bitch, I'm horny. I wanna come over," the voice on the phone was friendly and relaxed. Calling her a bitch was their own inside joke.

"Oh, hey Randy." Work wasn't going well. Jessica was obsessing over her afternoon with Melissa and couldn't seem to focus.

'I'm a monster,' Jessica had thought to herself all the way home. 'I mean, okay, he, I mean,n she, right, gotta remember that Melissa loves it, I know she does. But what am I doing to her? Treating her like that? Why can't I stop myself?'

The whole time with Melissa, first the fight, then the making up, then the sexual dry humping… it was as if Jessica had been possessed by demons. She couldn't seem to stop herself from dragging Melissa deeper and deeper into the clutches of the Johnson family.

Oh sure, she could say that it was all for Melissa's own good, to show Melissa what she was getting herself into. But that was bullshit. Total bullshit, Jessica now realized. And all her prior manipulations, had she known all along what type of person Melissa was? How desperately lonely for attention Melissa must be? Had she somehow known, maybe subconsciously, that Melissa wanted to be controlled and led into womanhood by the two dominant Johnson ladies?

And she felt something more. Something she couldn't quite put her finger on. A deep ache.

"Babe? Earth to J.J."

"Sorry, Randy," Jessica snapped back to the present. "Hey, I'm really tired. I… I think I should just go to sleep and catch you tomorrow."

"Oh, okay. Cool. 'morrow."

Jessica hung up the phone feeling uneasy.

"What the fuck am I doing?" she shouted at herself, picking her phone back up.

"Randy? Still horny? Cool. Your bitch is comin' over."

But it turned out to be a mistake. One humongous, massive, horrible mistake because she couldn't cum. Randy, eyes closed, grunting and sweating, pounded into her, but she was going nowhere.

"Fuck!" she muttered, pushing Randy off. She rolled him onto his back and mounted him from above, something they had never done before.

"Hot!" Randy said, loving the new position. He reached for her breasts.

"No," she grunted, grabbing his wrists and holding them to the bed. She pressed into him, trying her best to get off. And just then, her mind flashed back to Melissa, trapped underneath her, mewling and gasping in pleasure, her soft body, red lips, and perfume, submitting as Jessica rubbed against her, and just like that, it happened.

God dammit, Mom! Jessica thought angrily to herself as her orgasm rocked through her body. What the fuck have you done to me??