tagTranssexuals & CrossdressersBeing a Sissy for Viv Ch. 02

Being a Sissy for Viv Ch. 02


After Viv's stimulation it took me a few moments to recover. By the time I looked around Viv was sat on the couch sipping at her almost empty wine glass. A slight smile on her lips and a satisfied look on her face. Our eyes met for a moment before hers wandered down to her pink lace fronted panties I was wearing.

A wave of awareness swept over me as I suddenly became very conscious of what I was wearing. I stood up rapidly. My arms unconsciously moving to attempt to hide the panties and bra Viv, had told me to wear such a short time ago. My thoughts a whirling confusion once again.

"Oh how cute." She murmured, her head tilted slightly to one side. "My panty boy all embarrassed and trying to hide his pretty lingerie just like a real girlie."

I felt my face heat red as her words focused my thoughts. Now that my excitement had been satisfied somewhat it was no longer strong enough to keep the overpowering feelings of embarrassment at bay. A wave of shame and humiliation swept through me. I desperately wanted to run away, drive home, lock my door and pretend the evening had never happened.

"Now Chrissy lets have your hands out of the way so I can see how you look in my underwear."

I felt helpless as a slowly rising tide of dread and apprehension threatened to consume all my thoughts with the reality of what I had done. Less than an hour ago Viv had been nothing more than a trusted female work colleague. A mature lady I worked with every day. Now I was stood in her house, her lounge, wearing nothing but a pair of her panties and a bra that had been supporting her breasts all day. She knew one of my deepest secrets. She now had a power over me. A power that stopped me from being able to run away. A power that made my hands move to obey almost against my will. She smiled to herself as I slowly moved my hands to reveal her lacy bra and damp pink panties on my semi naked body.

Viv simply sat for a few moments, slowly looking me up and down before finishing her glass of wine.

"Well Chrissy, I don't have a maids dress for you to wear right now but my sissy maid will need to get used to doing her duties in just her underwear sometimes. I need some more wine."

I didn't move, but just stood there looking at the empty wine glass and unconsciously chewing on my bottom lip. Thoughts and emotions whirled inside me. Going to get some more wine, a simple innocuous activity, something I'd done thousands of times without a second thought. Now I hesitated, no longer being driven by uncontrollable excitement. This time I was doing it because Viv had told me to. This time I was doing it because Viv had become Mistress Viv. This time I was doing it as my very first act of submission.

"Chrissy." Viv's sharper tone of voice interrupted my thoughts and made my gaze move from the wine glass to her face.

"My sissy maid will do what I tell her to do when I tell her to or else I will pull her panties down and spank her bare bottom. Is that clear?"

"No!" I exclaimed, almost before Viv had finished speaking. But at the same time my manhood had twitched again. Another long held desire unexpectedly started to clamour for attention in the whirl of confused thoughts rushing around my head.

I suddenly moved towards her to collect her glass. The thoughts of me over her lap, of pretty panties pulled down and the sharp impact of a hand on my bare buttocks driving a rising excitement. But the embarrassing thoughts were still stronger. I had already revealed one secret desire tonight. I mustn't reveal another. I couldn't reveal how much her new threats excited me.

As I moved around the foot stools between us Viv leaned forward to hold the empty glass out to me. The movement stretched her blouse tight over her large unsupported breasts. The outline of her hard nipples gave me a visual reminder that I wasn't the only one being driven by sensual stimulation this evening.

"Good girl Chrissy, I put the bottle in the fridge to keep cool." She prompted in a gentler voice as the reminder of her excitement made me hesitate again, wine glass in hand.

"Errr . . . Yes. Yes ma'am." I muttered, pre-occupied with my thoughts as I made my way into the kitchen. I fumbled for the light switch and my hands were unsteady as I poured the last of the wine and reviewed the running away option once again. She was more than 20 years older than me and though probably about my weight was several inches smaller, there was no way she could physically stop me.

Yet I was wearing her underwear and all my male clothes were laid out upstairs on her bed. I couldn't be out the door before she realised. There would be a confrontation. How could I possibly win that stood there in her lace fronted panties and smart white work bra.

Still struggling to organise my thoughts I hesitated for a second before re-entering the lounge with the wine glass. Taking a deep breath I could feel the familiar comforting tightness of the bra straps around my chest. In Viv's panties, still damp with my cum, my manhood twitched slightly at the feeling.

Viv was sat where I had left her on the couch, legs crossed and hands on her knees. She watched me keenly, but with a small smile on her face as I carefully placed the refilled glass on the side table beside her.

"Good girl Chrissy." Now that wasn't too bad was it."

"No ma'am." I replied in a small voice. Viv sipped her wine as she regarded me for a few seconds.

"Now I suppose we had best get you out of those panties you made all wet and messy and cleaned up."

A sense of relief flooded through my thoughts at her words. My embarrassment would soon be over, it was already quite late and we had work early in the morning. Soon I would be on my way home and my secret sissy desires would be safe once again. At the same time lurking in the shadows at the back of my thoughts was a nagging sense of disappointment. A sense of an opportunity lost.

Viv lead me back upstairs once more. Again my face was only a few inches from her backside. I wondered if her panties matched the bra she'd taken off for me to wear. Suddenly, unbidden, the sense of disappointment stepped out of the shadows in my mind. A scene of me stepping into Viv's imagined panties spring into my thoughts. As it always did my excitement started to return at just the thought of wearing lingerie.

On the landing at the top of the stairs Viv pointed me towards the main bathroom and not the en-suite attached to her bedroom.

"Go clean yourself up Chrissy and then bring my panties through."

I did as she instructed, taking off her cum stained panties and showering my lower half to remove the almost dried dampness Viv's fingers had brought forth. After drying myself off and with a small towel to cover my nakedness I padded across the landing to Viv's bedroom. Still enjoying the feel of the straps of the bra I was soon to take off and holding her soiled panties in one hand.

I was a few steps into the room before I noticed the full length satin night gown lying on the bed. My eyes had passed over it and were looking at Viv before my head snapped back around to look at the beautiful peach satin creation carefully arranged on the bed. My reaction must have been comical to watch as Viv gave a small chuckle.

"Well, well, well, my sissy can't take her eyes off anything pretty and feminine can she?" The gentle taunt took a second to register and I reluctantly dragged my eyes away from the gorgeous nightie and met Viv's eyes. They sparkled with mischief.

"It's OK Chrissy. I know a sissy like you can't resist looking at something so pretty and girly." My eyes glanced back at the bed but returned to Viv as I tried to hide the desire and keep the pleading look off my face. I could feel my excitement starting to return and my cheeks coloured with embarrassment once again as I realised how easily the sight of something feminine had consigned my thoughts of shame and humiliation to the back of my mind, no matter how briefly.

Viv took a few steps and stood next to me, her hands on my shoulders, turning me to face the forbidden fruit she had laid out on the bed. Her fingers gently traced my bra straps as she whispered in my ear.

"Do you want to wear it Chrissy?"

"Just think how soft and smooth the satin will feel on your skin."

"Just think how pretty you'd look in it."

My heart raced and I had to breathe deeply. My world suddenly seemed to be consumed by the feeling of her fingers gently smoothing along my bra straps and the vision of the lovely peach satin creation she was teasing me with. The towel I clutched to myself was now hiding my slowly growing excitement. An excitement that was growing in my thoughts too. Slowly starting to win the battle against the fear of humiliation.

I stood there thinking for several seconds. Viv was silent, but her fingers continued their gentle exploration along the bra straps on my back and shoulder. You've already begged to wear her panties and bra murmured an insidious voice in my head. Wearing her nightie isn't going to hurt any now. Then in an almost dream like state once again, I felt myself nodding my head.

Viv's hand stopped stroking my bra straps and gave my bare backside a playful slap.

"I will not accept nods from my sissy. I expect clear spoken answers. Is that understood?"

Our eyes met, hers seemed to contain only firm resolve. After a second I had to lower my head. I swallowed. Once more the desire and excitement overwhelmed my fear and embarrassment. Once more I chose to ask to be able to dress in something pretty. I asked to be allowed to submerge my masculinity under gorgeous femininity.

"Please may I wear your nightie Mistress?"

Viv leaned closer, her warm breasts against the top of my arm, her fingers continuing to remind me I was wearing her bra by gently running along the straps.

"Why Chrissy, tell me why." She whispered in my ear.

"Because I'm a sissy ma'am. I love to wear pretty girlie things." I replied in a low voice but with only a small hesitation.

"Good girl Chrissy." Said Viv and moved to pick up her nightie, her arms arranging it so that I could slide it over my head. I hesitated to discard my towel and expose my hardness to her. After a seconds hesitation I knew I had no option and throwing it on the bed I took a step closer, raising my arms so Viv could help me into another item of her lingerie.

My excitement had risen again with the anticipation of wearing Viv's wonderful nightie and we were so close that the tip of my cock brushed against her black skirt. I gasped but Viv only smiled and a second later I felt the soft cool satin cascade down my body, pooling for a second around my prominent hardness before sliding down to half way down my calves.

Viv guided me in front of the large full length mirror on the wardrobe doors. My breath ragged and deep as the soft material caressed the end of my uncontrolled male excitement. I watched in the mirror as Viv tied the ribbon to pull it tight around my chest. Then her breasts were warm and soft on my back once again as her hands reached around the front to arrange the semi sheer material at the front over my panty filled bra cups. In the mirror it was easy to make out the patterns on the lacy bra cups as her hands smoothed the material down.

"Look how pretty you are Chrissy." She whispered as she moved even closer and I felt more of her warm body against me.

"And excited." She added a few moments later as her hands moved lower and pulled the peach satin tight revealing the tell tale bulge that betrayed my intimate desires.

"Who would have imagined a strong professional man like you unable to resist the excitement of wearing my bra and panties? Getting so excited that he begs to be my sissy maid." Her fingers started to lightly explore my excitement hidden only by a single thin layer of satin.

Suddenly despite the distracting excitement of Viv's fingertips stroking my hard cock through the soft satin, I realised what I had already known but had refused to accept. The source of Viv's power over me was not the fear and embarrassment. Not the thought of the humiliation if she revealed my secret desires. Not once had she ever mentioned any threat of public humiliation. There had been no hint of deep secrets being revealed.

No, it was the desires themselves that that gave her the power. She knew I just couldn't resist the excitement. The thrill of slipping into feminine finery. From smart skirt and blouse to sheer sissy frills she knew I was unable to say no when she offered me the chance to satisfy my addiction. That was why she was going to be Mistress Viv and I was going to be Chrissy, her sissy maid. I smiled to myself and suddenly the thoughts raging in my mind seem to slow a little.

Oblivious to my thoughts Viv continued to murmur softly into my ear as a single finger continued to tease.

"Well, your dressed pretty enough for a sissy in my nightie, so now I think it's time to start on the maid training."

"Yes Mistress." I replied, now with almost no hesitation.

Viv turned me around, our breasts touching her face looking up to mine.

"Kneel." She said in a voice that suddenly contained a hint of excited huskiness. "Kneel for your Mistress."

Slowly I did as she had commanded. Carefully arranging her nightie so it still touched my hardness at the front and flowed over the back of my legs. I looked up at her, her substantial breasts, unsupported since she made me wear her bra, strained at the white material of her work blouse. Her nipples proud and obvious. The slightly sheer fabric allowing me to see a hint of her darker areola. After taking the opportunity to gaze at her hidden breasts for a second or so I looked further up to her face.

Viv was looking at us in the mirror. Watching the man she had made her sissy kneeling before her, waiting patiently for her next command.

"Closer Chrissy, come closer."

Awkwardly I shuffled closer to her on my knees. I was only a couple of inches from her skirt, my own breasts just touching it. I took a deep breath, felt the bra straps tight around my chest. Then her hands were on the back of my head, fingers running through my hair as she pulled my face into the black material that already filled my vision. Her legs parted as much as her skirt would allow. Her hands pushed me between her thighs. I leaned forward slightly as she used my face to push the material of her skirt and underskirt against her unseen panties.

It was hard to breath, but incredibly exciting, my Mistress using me to gently rub herself off through her clothes. I pushed my face forward a little harder and was rewarded with a gentle sigh from Viv. I smiled at the sound and my erection twitched a little against the satin of her nightie. I pushed forward again, and then again. Establishing a rhythm, helped by the insistent pushing of Viv's hands on my head. Enjoying the increasing sighs and gentle moans of my Mistress as my face and cheeks became hot and flushed with the heat from being buried between her thighs.

Suddenly there was a coolness over my face and fresh air to breath as the pressure from her hands lessened.

"My panties sissy. Your Mistress needs you to take her panties off." Commanded Viv, her voice now containing the flush of excitement I knew to be on her face.

"Yes Mistress." I said simply. I moved my hands to the back of her calves. Then slowly but steadily slid them up the back of her nylon covered legs. There was a gentle moan as I stroked past her knees and another as I angled towards the inside of her thighs before smoothing my hands up the smoothness of her tights to hold as much as I could of her backside. At the same time pushing my face deep into her skirt once again.

"Mmmmmh. Ohhh, good girl Chrissy."

I listened to Viv's ragged breathing for a few seconds before my fingers searched for the waistband of her panties. Slowly easing them down along with her tights. I leaned back a little as my fingers moved to the side to inch the front of her hidden underwear down too. Idly I wondered once again if her panties matched the bra she had been wearing before me. Would she make me wear them as a set sometime I mused? Looking up to her breasts and face once again I pulled her tights and panties slowly down her thighs.

Viv was still looking in the mirror, but there was a smile on her flushed face, her nipples seemed even more pronounced under her blouse. Her fingers lightly holding the back of my head for balance as I continued working her combined tights and panties down her legs. Then past her ankles and finally off her feet.

I carefully arranged the removed lingerie so I could get a better look and see if they were a matching set with the bra I wore. They were white with lace panels at the front and the pattern seemed the same. I smiled to myself before Viv's voice interrupted me once again.

"Just like a sissy panty boy, so easily distracted by a pair of pretty panties. You can look at them more closely later Chrissy. Right now you have maid duties to perform. Get under my skirt and please your Mistress."

Her hands were insistently pushing my head downwards towards the hem of her skirt.

"Yes Mistress Viv." I murmured as I dipped my head to get under her skirt. I gently kissed the inside of her knees and her legs parted a little more, but there wasn't really enough room. Her smart black skirt and dark blue nylon half slip wrapped around my head and rode up as my lips caressed their way up one of her thighs. My hands smoothed up the outside of the silky nylon slip and reached her cheeks just as my nose felt the first wisps of her pubes.

Viv gasped and shuffled forward a little, her hands once more pushing at the back of my head now through her skirt. I was forced to lean back a little more and my mouth felt a warm wetness as it was pushed against her most intimate place. My tongue pushed between my lips and gentle explored Viv's pussy lips. I was rewarded with a groan as I experienced the taste of her for the first time.

"Oh yes, oh yes. You are going to be such a good sissy." Gasped Viv.

After a few seconds of gentle exploration and with my lips and chin slippery from her juices I pushed my tongue as far out and into her as I could. Viv groaned, her thighs parting a little more as she squatted slightly. My tongue delved a little deeper and Viv took another small step forwards pushing me further back my thighs touched my calves and I was lost in the sensations.

My tongue deep inside my so recently respectable older work colleagues pussy. Her warm wetness all over my lips and chin. Her bra straps comfortably tight around my chest. My hands squeezing and groping her backside. The grip the only thing stopping me over balancing backwards. My male hardness rampant and covered with cool satin lightly caressing it every time it twitched.

I stopped my probing deep inside her and started circling my tongue towards the top of her lips. He gasps and moans became more insistent. Sharper. Louder. Her hands pushed my face between her legs at regular intervals. I continued rhythmic motions with my tongue. Circling her clitoris. Then on her lips. Then a few seconds deep inside. Then returning to the tight bud at the top of her pussy. I felt more warm juices trickle over my face. More insistent groans. My tongue starting to ache as I tried to please my new Mistress.

Then suddenly her thighs tried to close instead of opening and I tasted a fresh wave of juices. Her hands pressed my face hard into her pussy for a few seconds. Then Viv relaxed with a huge sigh.

Suddenly I could see her bedroom once more as she took a step back to sit on the edge of the bed. Releasing my head from the restrictive enclosure of her smart working skirt and slip. I remained where I was kneeling on her bedroom floor and simply enjoyed the view as Viv half lay back, using her hands to support herself. It stretched her blouse tight against her large breasts, making it a little more see through and showed her nipples still hard surrounded by her mid brown areola. Her smart skirt was now bunched half way up her thighs and her blue nylon underskirt was showing its lace trim. Her blouse was only half tucked in her skirt and her shoulder length hair was mussed. The contrast with the smart professional from a few hours before made it all the more exciting.

Report Story

byCaron© 9 comments/ 91841 views/ 32 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: