Being a Sissy for Viv Ch. 07

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Starting Chrissy's maid training.
7.6k words
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Part 7 of the 7 part series

Updated 06/08/2023
Created 01/31/2013
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Caron
Caron
182 Followers

With a sense of relief, I pulled into Viv's driveway. Despite the shortness of the drive, my apprehension had been acute. After three weeks I'd almost grown used to wearing panties every day, but this morning was a new step. Beneath my drab male top clothes, I was wearing a complete set of pretty pink lingerie. A bra, panties, suspender belt and stockings along with red painted toe nails. Objectively, my dire thoughts of discovery and humiliation during the fifteen-minute journey were ridiculous. However, the careful, almost obsessive secrecy with which I'd guarded my sissy self for so many years, was deeply embedded and could not be changed quickly.

I approached the house carefully, firmly holding a large sports bag. Everything, including Viv's house, was quiet and dark and I hesitated a few seconds, to compose myself a little, before ringing the bell and committing to the coming day.

The hall light came on within a couple of seconds and Viv, Mistress Viv to me now, answered the door quickly. She'd obviously been waiting for me despite her love of sleeping in. Saying nothing as she opened the door, her eyes scanned the dark street and houses opposite. Then, apparently satisfied no one was around so early on a Sunday morning, she stepped back to allow me inside.

Softly closing the door behind me I turned to my new Mistress. She was wearing her red nylon nightgown again, the one she'd worn that first night. The belt of her wrap in a tight bow holding it snug against her. For barely a second my eyes went to her breasts, nipples proud and obvious even through the two thin layers of smooth nylon fabric. Then up to her expressionless face until our eyes met. There was a noticeable pause before we both grinned widely and I saw her excited anticipation revealed.

"Good morning, Chrissy," she said, her generous smile warming her face and highlighting the sparkle in her eyes.

"Morning ma'am," I replied with a similar large smile. A sense of calmness washing over me at her genuine acceptance of who I really was.

There was a pause, then Viv took a deeper breath and fought to get her smile into a suitably stern facial expression. It didn't quite work, but neither of us cared. Even less so for me as the deep breath only served to emphasize her ample breasts and conspicuous nipples.

"Well Chrissy, I didn't get out of bed at this unearthly hour to see a man in ugly clothes. My panty boy had better show me the pretty lingerie he's wearing."

I hesitated wondering where to put my male things.

"Now."

"Yes Ma'am," I replied and simply put the bag down and started to remove my male things where I stood.

I tried to go slowly, to tease both my Mistress and myself, but my desires were too strong and very quickly I stood in the unfamiliar hallway in nothing but my lingerie. My male clothes, un-important to both of us, lay discarded on the carpet in an untidy pile. I could tell my face was flushed with embarrassment. Despite Viv's acceptance, simply stripping and openly displaying my crossdressing still filled me with nervous apprehension.

Apparently oblivious to my feelings, her eyes were slowly taking in the view she had of her male work colleague, standing in her house, wearing nothing but ladies' underwear.

My stockings were plain baby pink held up by the four straps on my white lace suspender belt. The panties were full cut pink nylon, slightly on the loose side. The looseness allowed my excitement more room to bulge outwards. Viv had surreptitiously given the panties to me at work on Friday afternoon. 'Make sure my sissy is wearing these on Sunday' was all she'd said as she left the non-descript package on my desk when no one was around. Now her eyes lingered on the pretty pink nylon, pushed outwards by my excitement. Apparently satisfied, her eyes travelled up to the bra around my chest. The pink lacy 'C' cups, useless and empty right now, emphasizing I was a man dressed in feminine underwear.

"I think we need to get my sissy some training bras to wear for when she can't have her own breasts in," said Viv, pulling at my bra cups. "Still, we don't have to worry about that today," nodding to the bag I'd brought for the day's activities.

I turned, crouching to open the bag and retrieve my latex breast forms to fill out the waiting bra cups.

"No, no, no," interrupted Viv. "My sissy bends from the waist, not the knees," she replied to my quizzical look.

I smiled as I understood what she wanted. My nylon covered hardness responded again at the realisation that Viv wanted me dressed pretty and showing off to her. Slowly I bent at the waist to root out the breast forms. I could feel the suspender belt pulling the back of my stockings up, the nylon panties stretching over my backside, the bra straps tight around my chest. Inside the thrill of being watched, as I deliberately displayed my semi-feminised self, dominated my emotions. An acceptance that I really was an exhibitionist slut created a fresh wave of embarrassed excitement. The bulge in my pink nylon panties was significantly more noticeable as I straightened and turned towards my Mistress with breast forms in hand.

Viv took one from me, feeding it into a waiting bra cup and gently positioning it to her liking. At the same time telling me how much more feminine her sissy looked when her bra was properly filled. My focus was on her breasts. Only a few inches away, covered in two thin layers of smooth red nylon and swaying gently as she arranged my latex ones. My bra straps tightening noticeably as it fulfilled its purpose of supporting the weight of the now fully filled cups.

Viv's fingers tracing the straps down from my shoulders brought my focus back to the present even if my eyes were still enjoying my Mistress's barely concealed arousal. I felt her fingers continue around the sides of each lace bra cup before finger and thumb joined to caress the rather smaller nipples formed into the latex.

Suddenly Viv's fingers stopped and her hands started to move to cover her breasts as she realised the object of my rapt attention. I met her eyes, about to apologise, but already there was a soft chuckle as she realised how out of place her instinctive reaction had been. Though she'd willingly gone braless under the rather thin blouse she'd been wearing that first wine fuelled evening, since then she had been noticeably reluctant to allow me an unobstructed view of her lingerie areas.

"I think your Mistress needs a bit more practice Chrissy," she said quietly, deliberately lowering her hands. "Your intensity caught me a bit by surprise. At my age you don't expect such attention."

"Youthfulness has little to do with attractiveness ma'am. Age has an attraction all of its own."

Now I was subjected to intense scrutiny as Viv tried to decide if I was telling the truth, if the excitement that was bulging my panties was from more than standing in her hallway dressed only in pretty things. I met her stare fully, hoping she would know my words reflected my inner thoughts.

She looked far from convinced. "Well," she said eventually. Obviously unsure on how to respond to my statement for now. "Time for my panty boy to be more girl like. Hair next."

"Yes ma'am," I replied, deciding to let things lie for now too. I turned and crouched down to retrieve my cheap wig from the bag.

"My sissy will not bend her knees," came my Mistress's voice.

"Yes, Mistress," I replied with a small sigh at my forgetfulness before standing and slowly bending over to rummage in my bag to retrieve the blond wig. I settle it on my head. Adjusting it until I felt it sat just right. The shoulder length bangs framed my face but were a mess after the journey.

Before I could do anything more, Viv's fingers were combing through the fibres, smoothing it into a style she wanted and chasing errant strands back into place. I waited patiently for her to finish, my eyes mostly watching the intent look on her face.

Viv took a step back to appraise her efforts and, apparently satisfied that none of the strands of my shoulder length bob cut were too wild, gave a slight nod. Turning she moved to the side of the hallway pointing to a pair of pink fluffy slippers obviously waiting for her sissy to step into.

"My sissy will practice walking later when I can supervise her properly, she'll wear those for now."

"Yes ma'am," I replied, moving past her to obey. I preferred feeling the carpet under my stocking covered feet, but they were pretty open toed slip-ons with matching pink fluffy bobbles - unquestionably feminine. Putting a hand on the wall I slid each of my nylon covered feet into them, pleased to see the open toes left my red painted toenails clearly visible.

"Do you still want to be a maid, Chrissy?" I turned to face her. The tone in her voice was only a slight reflection of the serious one she'd used to ask me the same question the week before. The doubts in her mind were fading too. Understanding and acceptance of our new relationship were starting to become established.

"Of course, ma'am," I responded sincerely, "I want to be your sissy maid, ma'am."

Viv smiled at my verbal declaration. Then raised her hand to tick off points on her fingers as I'd seen so many times at work. "Well, my maid needs to get the washing into the dryer, make sure it's on the gentle cycle. There is another load of washing that needs to go in. My maid has been washing ladies' clothes for many years so I assume she knows what program to select?" She paused for me to agree then continued. "Then I need another cup of tea brought to me upstairs before you get breakfast. Is my maid - my sissy maid, clear on all that?"

"Yes ma'am," I replied, noticing the deliberate emphasis on 'my sissy maid' with a flush of excitement.

My Mistress stood long enough to watch me walk into the kitchen and look around to familiarise myself with the layout again, before I heard her start to make her way back upstairs to her bedroom. I glanced back into the hallway to catch a glimpse of the hem of her wrap and full-length nightgown as she climbed the stairs. I allowed myself a few seconds to enjoy the thought of how the red nylon cascading down my own body would feel before turning back to matters in hand.

* * *

My desires to be a sissy maid were of course mostly driven by the pretty feminine uniform, matching lingerie, and the more personal aspects of serving or being used by a Mistress. Household chores were not high on my arousal list. Though I discovered that being dressed only in lingerie in an unfamiliar house certainly was.

Wearing lingerie in my own home was always a thrill, but there was an element of safety, of familiarity. Why shouldn't I do what I want in my own house? Now though I was in a near stranger's house. Viv and I had been nothing more than colleagues for several years. Normally no one would even consider walking around a colleague's house in nothing but their underwear. Not only was I doing exactly that, but I was a man doing it in pretty feminine underwear. The feelings were intoxicating. Standing in a strange kitchen wearing nothing but stockings, suspender belt, a bra and panties. Pink nylon panties, that were filled with an obvious erection.

I luxuriated in my excited thoughts. A warm, neat, tidy and in every way mundane kitchen, but to me right then, a place of deep taboo excitement. I breathed deeply, savouring the moments, and couldn't help but tease my panty covered arousal. Viv's kitchen windows were not overlooked, but the feeling of being exposed to the world was very real to a closet sissy like me.

Eventually I refocused my thoughts on the kitchen. With some reluctance I removed my fingers from my panty covered sissy clitty and set about the tasks given to me. As I bent to retrieve the finished load in the washing machine, I quickly realised even mundane household chores could have their positive points. The first was the feel of my heavy breasts dangling in my bra. The second was the realisation that this was mostly Viv's underwear and blouses from the week at work. Almost every item was feminine and pretty, with an abundance of lace and details. I slowly, carefully transferred the load item by item to the dryer. I almost felt like a voyeur, holding up and examining Viv's panties, her bras, her slips, each pretty sexy blouse.

My sissy clitty was rigid and tenting my nylon panties by the time I'd finished. I couldn't decide which was more erotic, knowing that they'd been against the most intimate parts of Viv's body or the thought of sliding them onto my own body one day. With great reluctance I placed the last item, a full-length white nylon slip with a lace hem and matching trim round the gathered bust into the dryer. It was then I realised that Viv couldn't possibly have worn all these things in the week.

She must have deliberately selected the items for me, for 'her' sissy maid, to handle. Careful consideration or just a way to tease her sissy I mused as I set the dryer to the warm gentle cycle. I turned and bent to put the next load into the washer. This pile was filled with similar items, this time the rich dark colours making them sexy rather than pretty. The most boring one being the calf length pencil skirt she'd worn for the formal customer meeting on Wednesday. At the bottom of the pile was the vivid red blouse she'd worn to my house the week before and the black, lace-edged panties she had tied around my face.

Consideration or teasing? To me there was little difference. My Mistress cared enough to go to some lengths to excite her new sissy maid. With a smile and a sense of satisfaction that went deeper than my lips I set about making her a cup of tea.

* * *

With a steaming cup in hand, I left the kitchen. Carefully and quietly making my way up the thickly carpeted stairs to Viv's bedroom. I concentrated on the sensations of the lingerie on my body and the excited thoughts running wildly through my head. I paused by the mirror on the landing to admire my image, the full pink lacy bra around my chest, pink panties with a slight bulge and the slightly paler pink nylon stockings. I wanted the moment to last forever. The feeling of being in a strange house in nothing but pretty lingerie, of doing something so outrageous, so wrong, so naughty and taboo and with the anticipation of spending the day with my new Mistress. It felt like a perfect moment. The man in the mirror wearing the pink lacy bra smiled back at me with a happy contented expression.

I pulled my thoughts back to my Mistress waiting for her sissy maid and her early morning tea and slowly made my way into Viv's warm dimly lit bedroom. She was sitting up in bed reading a magazine by the light of the bedside lamp. As I entered the magazine didn't move, but her eyes followed me around the room.

"Your tea Mistress," I said, placing it on her bedside unit and standing by the bed, uncertain what to do next. Viv slowly put the sewing magazine aside and picked up her tea, blowing and sipping as her eyes examined my lingerie covered body. She'd gone back to bed without her wrap on, it lay across the foot of the bed. The red nylon nightgown was stretched tight over her breasts and revealed far more of her arms and chest than I ever got to see at work. Her eyes were scrutinising my body, whilst mine were covertly admiring her thinly covered breasts, fascinated by her hard-pointing nipples.

"I see my sissy likes her new panties," she said between sips of tea.

I glanced down, unable to suppress the colouring of my cheeks as Viv observed my bulging full cut pink nylon panties. There was little reason to be embarrassed of course, but ingrained habits cannot be controlled so easily. If I was honest with myself, the embarrassment of having the bulge in my panties pointed out, only added to my excitement.

"Why does my sissy like them so much Chrissy?"

My colour deepened and I swallowed nervously as I prepared to tell my Mistress what used to be my secret once again. It was even more humiliating to admit it out loud. More humiliating and much more exciting. I wondered, or rather hoped it was just as exciting for Viv too. Knowing my Mistress was excited made my own embarrassed excitement rise even more.

"They are such a pretty pink ma'am. And... and they feel so soft and exciting covering my... my sissy clitty ma'am." I didn't need to see Viv's eyes flick to my panties to know my excitement was moving under the sensuous nylon as I had to verbalise my secret desires.

"Your Mistress likes the way she can see how excited her sissy is."

I looked down again, the panties Viv had presented to me were full cut, plain pink nylon with just a touch of lace at the waist and legs. They were also slightly loose and so allowed my excited sissy clitty far more room to grow than tighter fitting panties did. I wondered where Viv had got them from and if the looseness was something she'd deliberately looked for or was merely a happy coincidence.

"My sissy is not pretty enough." She nodded to the dresser. "Let's see if you've been practicing Chrissy."

I'd already seen the dresser when I'd first entered, it was laid out with a small selection of her make-up. As I sat on the padded stool, I realised all the items were the same as the ones Viv had given me to practice with the weekend before.

Prior to becoming her sissy, I'd never experimented with make-up, just the odd lipstick from time to time. I'd been stunned by the difference it made to my look when Viv applied it on her visit. Not just to my look but how it made me feel, how it somehow completed my transformation into a girl, a panty boy, a sissy. How it made Chris into Chrissy.

At Mistress Viv's instruction I had practiced each night in the intervening week. Basic steps, foundation, blusher, eye base and liner and of course the irresistible rich red lipstick to match the nail varnish. My attempts were obviously crude, but in my final practice session I'd achieved a look that at least made me look a little better and not worse. I took a deep breath and caught a glimpse of Viv in the mirror, sat in bed watching me with that small smile. I reached for the foundation and Viv hid a broader smile with a sip of her tea.

I was concentrating hard on finding the balance between too much and not enough on my second cheek as Viv started asking me questions about my drive over. I was slow to respond as I tried to balance both sides of my face, but it gave me time to think. Eventually I had to admit, to her and to myself that the fear had rapidly turned to thrill. It was harder to identify the exact cause of the thrill, the excitement of being in public wearing lingerie even when so well hidden from casual gaze. Part was the wrongness, breaking the prohibition society had for crossdressers, part was the exhibitionist tendencies I was beginning to accept I had. Mostly though this morning it had been about taking a fear and conquering it, banishing it from my thoughts.

Viv's smile became broader still as I told her these things between applying the foundation and my cautious attempts at the blusher. I contemplated her smile and my reactions to driving here in full lingerie. Viv had been insistent that I should arrive in lingerie and I had expressed significant resistance. Eventually she'd dropped into full Mistress mode when we were alone in one of the conference rooms at work.

'My sissy maid will arrive in full lingerie. She will do what her Mistress tells her.' Viv's newly developing Mistress persona had faltered on occasion in the last few weeks but there'd been no give in her tone, or her eyes, that time. Another tone and look I recognised from working together. When she decided it was important, it would get done. No arguments. Of course, outside of work she had no formal authority over me. Her authority came only from my own deep desires to be feminised. That was partly what had made me reluctantly agree to her demand to arrive wearing lingerie. Over the week however I'd come to realise that not disappointing Viv was another important factor in my agreement.

Caron
Caron
182 Followers