Mistress Norma's Sissy Ch. 02

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Will takes the next step and become Willow!
7.3k words
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Part 2 of the 2 part series

Updated 06/13/2023
Created 01/26/2023
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Thank you everyone who read Chapter one and provided feedback and comments! And for those of you just finding me, there is an important Chapter one that will help you understand this growing relationship better, I think. Also, please check it out, I have a few other 'sissy series' here at Literotica!

Ch. 02

My whirlwind Saturday afternoon interview at Norma Richards' home was culminated by an hour-long conversation while she edged me, during which I confessed all my fetishes, sissy desires, and interests. She then proceeded to lock me into a plastic chastity device and had me suckle her shapely large breasts as she fondled my cupped-up balls, keeping me aroused and leaking that whole time I nursed on her.

Finally, this session of oral breast worship was over... She pulled my face away from her breasts, breaking me out of what I swear was a hypnotic trance! I have read that some of the Dommes and subs out there call that 'subspace'. Our faces were just a foot or so apart, eyes locked, when she started talking:

"Well young man..." she started, with a slight smile on her face, "It looks like you passed the interview for my new tenant! With flying colors, I might say. You know, I've been looking for a sub to live in with me for too long, mostly through my Femdom connections in Chicago. But the few people I interviewed who I thought at first were acceptable turned out to be so weird or creepy when it came down to a face-to-face meeting. Or they didn't want to move away from the big city when push came to shove. So, I gave up on that. I never dreamed I'd find anyone with those same interests through the university housing page. I guess I lucked out..." And they she looked at me, right at me... "Maybe WE lucked out, eh?"

And still recovering from that trancelike experience, I nodded yes, still in a bit of a haze. My cheeks were flushed and my eyes wet...

She continued, putting her tank top back on: "Ok, well now with Sally cancelling tonight, I have the whole rest of a Saturday afternoon and evening free. This is a rare weekend that I am not hosting any guests! We have a lot to take care of, do you know that?"

And I shrugged, not really knowing what she had in mind.

But in short order, she made it clear: we had a quick bite to eat at the kitchen island, she made us tuna salad sandwiches with a glass of white wine, we shared a little chit-chat. Then, she brought out paperwork, two forms or contracts, really: "Will, this is a standard lease agreement... and then laying a second set of pages next to it on the counter, this is our 'Mistress-Slave' agreement. The lease agreement was for a year, renewable. I would be compensated in full for my monthly rent by doing housecleaning, food shopping, the yard work, and... 'other duties dictated by the landlord'. The mistress-slave thing was mainly a list of ten rules, mostly about the slave's devotion to mistress, being obedient, how to address and converse with mistress, and a few other general open-ended statements.

I was so glad to have the rental, after barely flipping through both, I signed the documents, she countersigned, and then she made copies of the two documents and handed them to me. We took a second tour of the house, and going through the rooms in the rental space, she made it clear I would only be allowed to bring a limited number of things into her home. We grabbed four medium size boxes from her garage and hopped in her Lexus SUV and drove across town to my rental.

"Will, who is your landlord for this place? I know a few of the landlords in this town..."

When I told her, that is was owned by the Dennison Agency, she laughed. "Oh god, don't tell me you're lining the pockets of that Shylock, Bob Dennison? I've known him since I first moved to town, about twenty years ago! I'll give him a call on Monday and I will have him let you out of your lease; we'll get those last two months of rent back into your hands. That miser owes me more than one favor, for sure! And I know a thing or two, about his after-work interests that I'm sure he would NOT like to have broadcasted", she laughed.

We walked into my house with the empty boxes, and setting them in the foyer, Norma gave me brief instructions: "Will, I'm going to give you one hour, no more. You're going to fill those four boxes, if indeed you need them all. You don't need any kitchen stuff, no food, no furniture, just pack some clothes you like to wear, your personal and tech items, and anything small that's of sentimental value to you. I know a second-hand shop owner in town, he'll send out a couple of his guys this week, take out the furniture, look through the stuff you leave here, and either take it all into his shop, donate it to one of our local thrift shops or discard it. Then, I'll have Dennison get the house cleaned up and ready for his next tenants. He'll probably have someone moved into here within a week or two! So, this is no worry at all, so don't think another thought about this house!"

Well, it didn't take long, it turned out. With a strange feeling of relief and a bit of euphoria, I filled one box with my laptop and stuff from my desk, two boxes of clothes and shoes, and filled one with some pictures and other souvenirs I'd collected over the years. While I did this, Norma sat on the couch and worked her handheld. After thirty minutes, I had the boxes stacked up. I look at her and asked: "Yard tools? Mower?"

"No, Will, we don't need them, I have that all..."

"I have a tennis racket in the garage..."

Norma looked at me, and smiled, a nice warm, genuine smile: "Will, of course, anything else out there, golf clubs, skis?"

"Nope, this is all, then!" I smiled, too.

And in short order, the boxes were loaded into Norma's new SUV. She pulled out and I turned my head over my shoulder to see that rental house get smaller and small as we drove away, headed back to her place. We brought the boxes into my room, and then went for a walk around the yard. Norma showed me where all the yard tools were, and the lawnmower, and other stuff in the garage and an outdoor storage shed. She told me what yard and garden projects she had in her mind, and I made some comments about the generally good condition of the flower beds around the house, although I did have some suggestions for improvements...

And then, finally, Norma looked at me with a funny look and raised eyebrows: "Last but not least, Will, this is the last place you haven't seen in the house, my special room." And back inside, we walked halfway down the hallway, toward her bedroom, and stopped at a closed door. "Will, let me show you my dungeon..." She looked at me as she twisted open the doorknob and tilted her head in the direction of the opening door, as a signal to enter ahead of her.

I think I gasped a bit as I stepped in... This was probably the largest room in the whole house, at least as large as the living room, maybe bigger... There were a few low-wattage lights providing only the ability to just barely see and walk around. It looked in part like a converted exercise room, there were those interlocking rubber squares on the floor, a lot of mirrors on the walls, and even a few mirrors in select spots attached to the ceiling, the way there might be a mirror on the ceiling above a bed in some exotic apartment or sex-themed motel room...

"Let me show you what we have here, Will..." Norma now walked ahead of me, there was a cluster of equipment items in the center of the room, and then arranged around the walls, several other items. "This is of course, is a Saint Andrew's Cross; this is my riding horse, we have a couple of padded benches, different heights, one with stirrups, as you can see... Generally, they are for spankings, ass fucking, and... certain exam procedures... And these heavy rings, see above?" She pointed to a spot in the ceiling: "They are set into the structural beams of the house, and I have hand and neck stocks with chains for restraining a sub by the wrists or by the neck. And of course, you can see in the corner, my cage..." Maybe this cage had a six-by-six footprint, but it was barely four feet tall, meaning if you were put in this metal cage, you were either bent over, on all fours, or laying on the black rubber floor.

I'm thinking right this minute that Norma is showing me around the room the way a realtor might point out features of a home for sale: "Bay window here, the study is over there, and oh yes, the Saint Andrew's Cross is set up in the playroom." Oh boy, I thought to myself I don't ever want to see this woman in a foul mood!

But there was more, Norma walked over to a ceiling height cabinet, about six feet wide, and opening the double doors: "And Will, this is, well... I call this my tool chest..." she giggled to herself softly. Lined up on the back wall of the cabinet was pegboard and hooks, holding dozens and dozens of whips, paddles, crops, leather straps with buckles and D-rings, collars, cuffs, dildos, and some things I really couldn't even identify, looking more like chrome medical devices than BDSM play toys!

I stood, gawking, looking through all these items in the cabinet, and then pulling back, looking again, around the room, dumbfounded, speechless...

Norma read my look and stepped toward me to try to provide some assurances: "Will, this room typically gets used on some weekends, when we are hosting some of my 'special' guests. This is what they want, in part, what they are coming here for, what they are paying for, some of them... Now in your case, my sense right now is you might be more of a 'pleasure sub' than a pain sub. So maybe I won't ever need to take you in here unless I need an assistant, a second pair of hands to help me sometimes. Or if you disobey me or displease me somehow, and then for sure... You will spend some time in here with me! Have you ever had cane marks on your ass cheeks?" And she opened her eyes up way wide, laughed and gave me a glimpse of that beautiful smile of hers. "Now let's put those thoughts behind us, eh?" And she led the way, and holding the door open for me to pass out of this room, she closed the door as we stepped back into the hallway.

"Now..." Norma continued, "Let's see what we can do to get you feeling like this is your home, your new home!" We spent a few minutes in the kitchen, Norma showing me what was behind all the various doors and drawers. We went into the laundry room, we looked at all the cleaning essentials of the house, and showed me a large closet, "You'll soon become familiar with everything in here...", it was the vacuum, brooms, all the cleaning supplies for the house... "And you'll need a sissy maid uniform, of course! Standard issue is black, with white lace, but maybe I will get a pink one for you as well... Much more feminine, don't you think?" She asked that without really anticipating an answer and moved on to the next thing...

Then, we went back to my space, into the front room of my little apartment... "Are you ok, my sweet little boy, my little sissy? Everything here look like its going to be ok?"

I answered back: "Everything looks good... everything looks good." I repeated, the second time, very softly, almost to myself. Looking around the room, I noticed for the first time, my rooms were decorated mostly in pastel colors, and lots of highlights of pink, white, and yellow, I thought to myself, very feminine, very femmy...

"And this is ok, feeling ok, reasonably comfortable?" And as she finished the sentence, Norma reached to my crotch, and gripped lightly my chastity-trapped genitals.

"It's ok..." I replied, "a bit tight, but ok..."

"Well, it's supposed to be tight, you know!" Norma replied back. "Now Will, I need to know your clothes size information, so take your clothes off for me, dear..."

And standing there, near her, I knew this was not optional, I thought to myself, I might be naked in front of this sexy woman more than I think. I quickly pulled off my shirt and slipped my pants and shorts off after kicking off my sandals. My dicklet grew harder and pressed out against my cage.

Norma walked around me, twice. Looking my body over, up and down, touching my skin, rubbing my ass cheeks with her hands, pulling them apart to look at my anus. She lifted up one arm to see how much hair (barely any) there was in my armpit. She stroked my face, rubbing her fingertips across my forehead, cheeks, and chin.

"I can't get over, Will, how little body hair you have. This is natural? I'm sorry, I know I asked you before. It won't take many trips to the cosmetician for electrolysis to take out what you have under your arms and that little tuft of pubic hair... And that peach fuzz on your face, forearms, and legs. Now, let me get your measurements..." And with that, Norma pulled a tailor's measuring tape out of the desk drawer in my room. Quickly, she took chest, waist, and hip measurements: 38 inch chest, 30 inch waist, and 34 inch hips. Setting the tape down, she turned back to me, and reaching down with one hand, her fingers found my taught scrotum, and as she started to stroke and knead the silky skin of my ball sac, she came up very close to me, face to face, wanting to tease me. "I think you're somewhere around a dress size four or so, depending on the fit, and maybe a small or medium for other things. I think you're about one size smaller than me. What about your shoes, Will, what size are your feet?"

"Usually a seven is just right.", my reply.

"Ok, well about eight or eight in a half women's then..."

I nodded, "I think so, yes..."

"Ok, Will, now don't move an inch, don't move I will be right back!" She left the front room of 'my' suite, and I stood there, naked and still, for about five minutes. Norma came back with a small armload of clothes on her arm. Feminine clothes, she laid them down on the sofa.

"Now Will, a couple of things: I think when we are here at home, or anywhere alone, or with Sally, you will address me as 'Mistress Norma'; you will do the same for Sally: 'Mistress Sally'. In any vanilla public setting you may call me 'Norma', although if the setting is more formal, I really would prefer 'Ms. Richards'.

I nodded, and smiled slightly, to show her I understood: 'Yes, Mistress Norma'.

She continued: "And we'll need a sissy name for you. I think today will be the last day I will ever use 'Will' behind closed doors. Do you have a sissy name for yourself?"

And I gulped, and I could feel my cheeks turn a bit pink... I did have a name, which I had already chosen for my feminine persona, something that was never spoken, but only inside my head... I looked up into Mistress Norma's eyes, and spoke the name: "Yes, Mistress Norma, it's 'Willow'. I feel like I'd like to look like Willow Rosenburg, from the 'Buffy' series. Especially in the start of the series, she was so shy and not a very confident girl, so I identify with that. And very cute, and I loved her rusty hair color... And of course, my whole name, 'Will' is within 'Willow', too... I've masturbated often, many, many times, to the thoughts of me being Willow: sucking really large cocks, bent over and being ass-fucked... double-played... about being in the center of a group of naked men, servicing one cock after another... I'd like my sissy name to be 'Willow', Mistress Norma".

The shapely brunette looked me up and down. Looking again, right into my eyes, she spoke softly, caringly: "I think it's perfect... Willow it is...I think if fits you just right! The other name, the old name, we will try never to speak it, certainly inside the walls of my home! Ok, now try this on...Willow", and she pulled a neon pink lacey babydoll out of the armful of clothes she brought into my room.

Held up to me, the babydoll looked about as big as a handkerchief. Mistress Norma found the two spaghetti string shoulder straps and held it up to me: "Don't worry, this is spandex, it will fit you".

I took the garment, and finding the bottom, I slipped it over my head. As I pulled it down onto my body, I realized that the babydoll featured a low neckline, and open cups, so that my nipples, my sissy breasts were exposed. As I pulled it down, as far as I could stretch it, I realized it barely came down to the top of my chastity cage in the front, and only about one-third of the way down my ass cheeks in the back. My already hard boi-clitty pumped itself up one more size, further straining against my cage. I was so hard, I could see parts of me pushing through the air vent holes in the cage!

Norma eyed me up, twirled her fingers as a silent command for me to spin around, and then continued: "Willow, all of this that's gone on today, and now seeing you in this sexy little thing, I am so incredibly aroused! We need to move to my bedroom right now!

And with that, Mistress Norma took my cupped up my little sissy balls with one hand and gripped them securely with her thumb and pointer finger. Using my balls as a short leash of sorts, she tugged me down the hallway, into her bedroom. She pulled off her top, kicked off a pair of sandals and pulled down her shorts and panties, leaving us both naked there, against the side of her bed.

"Now Willow, get down on your knees, facing me." She said, matter of factly.

Without hesitation, I dropped down on my knees, facing Mistress Norma and the bed. She sat down on the edge of the bed, and opened her knees wide.

"Ok, now move in here between my thighs... Put your hands behind your back, yes, that's it, hold your hands, behind you. Now, I want you to take a nice long look, go ahead and stare at my pussy... I want you to study it...

I slid my knees a few more inches toward Mistress. My face was just a few inches away now, from Mistress Norma's pussy. She had a big, beautiful pubic mound, pink glossy pussy lips, and looking around the area, her skin was tanned and silky smooth. I couldn't even see any signs of stubble, as if her skin in this area was as smooth as baby skin! I thought to myself, she must have used electrolysis to permanently remove any trace of hair growth from her 'special region'.

"Just look, Willow, I want you to get to know my pussy, over time, you're going to spend hours and hours right here, pleasing me..." She cooed softly, and then put the fingers of both her hands on her pussy lips, and pulled them apart, gently... exposing the opening to her vagina and above it, I could see her clitoris, bulging out away from the rest of her pink flesh. Hard missing that, her nub, it looked to me to be about the size of a peanut or a marble, sitting proudly up and erect above the rest of her wet pink flesh.

After maybe a minute of silence and just staring at this beautiful display of raw femininity, Norma broke the silence: "Now Willow, close your eyes, my sissy... Close your eyes and come a bit closer, and inhale. I want you to smell my scent. Just go slowly, and count to yourself, I want you to take ten deep breaths. Fill your lungs with the scent of my sex, sissy. Just keep your eyes closed, and feel that warm scent enter you, enjoy theses sensations, enjoy it that I am filling up your lungs..." She took her two hands and placed them on the back of my head, guiding it into her, so my face would be right up against her, but without touching...

And silently, almost hypnotically, knowing that I was just one inch away from my new Mistress' sex, I began taking deep breaths, slowly filling my lungs, holding it in, and slowly exhaling... The scent was intoxicating, difficult to describe simply, a mix of her female essence, a female musky scent, some sweat, maybe a faint hint of pee, all tied together with a combination of a floral body wash and the clean smell of skin after a soapy shower. It was heaven, the scent was heavenly. I wished right then, I could dab a handkerchief against Mistress' glossy pussy, and keep it in my pocket to smell throughout the day. After ten deep, slow breaths, I stopped, opened my eyes, and looked up into Mistress Norma's beautiful hazel eyes... My cheeks were flushed, my eyes filled with water.

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