My eyes slowly adjusted to the dimly lit bedroom as I woke. It was early on a Saturday, and the sun was coming up, casting its warm yellow glow through the gaps in the curtains, signaling it was time to start my weekend routine.
I was the first awake — this was usual but now also expected. My transformation into Anne was now required to be completed for presentation to Mistress Jess when she was ready to begin her day.
Like most days my morning glory was present. I looked down to see the swelling that was straining the fabric of the red lace panties Mistress Jess instructed me to wear for bed. The now familiar feel of pretty lace on my skin and the sexy sight of my aching sissy cock in panties served only to increase the developing bulge. The urge to touch myself was ever present but I dared not without permission, disobedience would be punished with denial. No, I could wait, must wait! Also, I had much to accomplish before feeling ready. Over the past several weeks, since Mistress Jess had uncovered my new feminized persona Anne, I had become increasingly proficient at my transformation. Still, erasing all traces of my masculine self was a process so I had no time to waste.
Quickly and quietly, I slipped my red silk kimono over my shoulders and lightly tied it off at my waist. Plucking my red curls off the wig stand, I tip-toed to our ensuite to prepare.
Stripping out of my robe I caught a glimpse of Robbie's frame in the mirror. Somewhat masculine but slight shoulders and chest. Toned but slender arms. Smooth trim abdomen. Legs toned but slim. My hips, bubble-shaped ass, and manhood enclosed in red lace hinted at the end game of femininity.
I slipped my panties to the floor. My cock had never been an embarrassment but was also not impressive. Now without its fabric prison, it bounced in the mirror jutting out at six inches. Strangely, a large part of me wanted to put my panties back on, to feel the femininity they afforded, but there would be time for that afterward. Right now I needed to become Anne!
I opened the tap and stepped into the shower of warm water coming from the rainfall showerhead above. The cascades of water flowing over my face and shoulders delighted my skin. Vanilla is my weekend fragrance, approved by Mistress and adored by Anne. So, after slowly spinning in the water, thoroughly drenching myself, I generously applied the body wash to my loofah brush and began to gently scrub my body from head to toe slowly circling every inch of my body, reveling in the fragrance and feel of my freshly exfoliated skin.
The next step was to shave. Fortunately, I am not a particularly hairy person. This helps immensely but the fact remained that I am a mammal, a male, and there is hair that needs to be removed to become my feminine counterpart.
I started, as always, with my legs, in long slow strokes, feeling the cool touch of the razor gliding over my skin. Then arms, chest face, and neck, feeling less and less masculine with every passing second.
The last place to shave was my pink parts. For those of us born with a twig, this is much easier with an erection. Luckily the sensual feel of the shower and anticipation of femininity had done little to abate the swelling in my groin. Using shaving gel I massaged myself until I became fully hard. Now technically I was breaking the rules set by my Mistress, but she didn’t need to know, this was simply a matter of practicality, the pleasure was a pleasant side effect.
Moving my aching cock out of the way, I slid the razor smoothly and delightfully over the most sensitive of areas, throbbing more intensely, but wisely not pushing myself beyond the point of no return. Mistress Jess may forgive the practical need for rigidity, but she would not stand for more.
Now, with my body fresh, fragrant, and hair-free, I stepped out of the shower to towel off. Soft skin is a must for Anne. Bare Vanilla from Victoria's Secret has become a favourite. With palms coated in lotion I effortlessly covered my smooth skin. Every inch of me hair free, every crease and cranny soft to the touch and the scent of a woman filled the air.
I wrapped my smooth silky body in my kimono and progressed on to the final stages of the weekend transformation.
First, I fixed the wig to my head with bobby pins getting it just right. When I turned to the mirror I felt immediately feminine, my red curls falling to my shoulders, with a part down the middle. I was pretty and smiled sweetly to myself.
I was surprised at how practiced I had become at applying my makeup, and with each passing week, I felt more skilled. The first step, applying the foundation evenly. Then adding blush for color. Next I plucked, defined, and shaped my eyebrows, as well as enhanced my eyes with eyeshadow and eyeliner. The finishing touches were mascara and deep red lipstick.
“Hello Anne!” I whispered to the mirror and felt the familiar tingle run through my body.
Beginning that first night, when I came home to find Jess had discovered my secret craving to be feminine, there was a shift in our sexual dynamic. She had always been the one to take the lead sexually, and I happily followed. However, immediately upon revealing Anne, the role of submissive and dominant became more pronounced. This being new, we were uncertain as to what path a Sissy submissive and Femdom would take us down and how far we wanted to follow it. We had a few discussions. We did not want to "out" Robbie to friends and family, at least not yet. We did not want to disrupt life too much, too quickly. We did want to push boundaries and explore new desires. Somehow, organically, we drifted into a routine that was now very comfortable.
I spent Monday morning to Friday as Robbie. I went to work as a man. Came home and spent the evenings as a man. In most ways that matter, I was Robbie, she was Jess. However, once the weekend began, I transformed into Anne, the Weekend Sissy, there to serve the needs of Mistress Jess. As each Friday evening drew closer, my anticipation and craving for my female person grew stronger.
Now my Saturday morning makeover was completed. I heard my mistress stirring in our bed. My groin stirred as I began to wonder what she would have in store for her sissy today.
Dressed in only my short silky robe, I stepped from the ensuite into the bedroom. My mistress was still in bed, her shapely curvaceous legs and ass exposed to the sunlit room. As I approached her bedside, she rolled over, resting on her back, putting her spectacular breasts on display, the light freckles that speckled her D-cup globes barely visible in the dim lighting, her beautifully pink nipples standing out like raspberries against her pink areolas. She looked stunning!
“Good morning Mistress. I hope you had a lovely sleep,” I said in the most submissive voice I could muster. “I am ready.”
"Does Anne live to serve me?" she asked with a smile.
“Yes,” I said, nodding my head. "I live to serve you, Mistress Jess!"
Her expression and tone changed. Her eyes and voice commanded obedience.
"Then stand here next to me and take off that robe," she instructed. “Tell me Anne, did you wake up wanting to cum?”
My eyes locked onto her chest, heaving gently as she breathed. I moved toward her and disrobed, complying fully, exposing my already stiffening princess wand.
“Mistress, I did. I always do when I wake up next to my sexy Queen.”
“Look me in the eye when you answer!” she hissed sternly through her teeth.
“I am sorry Mistress.” My eyes quickly moved to her pretty face.
She had a playful look now, almost teasing with her eyes and Duchenne smile.
“I suppose I can’t be too hard on you for staring at these,” she said, cupping her tits and pinching her nipples. “They are lovely aren’t they?”
“Yes Mistress! They are perfect,” I replied, failing to maintain eye contact fully.
I forced my eyes back to her face as she massaged herself.
“I want to cum too, Anne,” she whispered.
I stared as one hand reached down between her legs, her knees spreading open, exposing her bald pink pussy. Smoothly she slipped her index and middle fingers over her labia and clit, massaging them.
The sight was nothing short of magnificent. A moan of pleasure escaped my lips simultaneous to hers. I began to fidget with my fingers, aching to touch her or myself, but dared not without permission.
I continued to watch in awe as her hand swirled around her clit. Fingers vanishing inside briefly, then reappearing to circle her nub.
“Anne, what are you thinking?” she asked through her pleasured seductive breaths.
“Mistress, I am thinking how wonderful it would feel if those were my fingers pleasing you,” my almost breathless reply continued, “I want to serve you, I want to help you cum.”
Taking her left hand from her breasts, Jess made a come here motion with her finger. Her right hand continued to explore the sensitive apex of her thighs.
I stepped closer, my erection now leaking precum inadvertently grazing her abdomen, her hand reaching for mine and guiding it to her thigh.
“You may touch me, Sissy, you may help me cum, but you must not cum yourself,” she cooed seductively.
“Yes Mistress, thank you, Mistress,” my voice quivered, “I understand.”
As my fingers slid through the crease of her hips I felt the heat of arousal, the dampness of her lips. My Mistress was wet and needed to cum, and I was thrilled to obediently help.
I could not take my eyes off her clit, swollen, dark pink and begging for attention. Gently I pressed my fingers to it, letting it slip between them, then massaging it as I pushed them inside her entrance. Sliding them with upward pressure inside her then raking my fingers back to her hood. Slowly I repeated the process. Stroking from her clit to her entrance then inside and back. Rhythmically pleasing my Mistress with my fingers. As I continued Jess pulled one of her nipples to her lips and sucked it firmly into her mouth, stifling her moans.
Reading her body language and taking her soft verbal cues, I knew she was close to a climax. I pushed deeper into her with two fingers, as she worshiped her own tits, alternating nipples in her mouth. With my digits as deep as they could be, she began thrusting her hips upward, trying to coax them deeper. My other hand moved to her clit, stroking it while she fucked my fingers.
I was close too, my sissy clit had been rubbing on her, leaving traces of sweet clear liquid on her skin. I needed to get my breathing under control to avoid disappointing her. With difficulty I forced myself to focus more on my Mistress, this was not for Sissy's pleasure. My role was to serve so with renewed vigor I continued stroking the wet walls of her canal with my fingers and strumming her clit.
Her breathing became more erratic. Short quick shallow breaths interlaced with moans of pleasure signaled the approaching release. She unlocked her nipples from her lips and shrieked with pleasure. I felt her tighten on my fingers and then a gush of nectar as she completed a short but intense orgasm.
“Excellent work Anne!" she said playfully as I pulled my drenched fingers from her.
“I am happy to be of service, Mistress,” I respectfully replied, desperate to lick my fingers clean.
It was then I noticed just how hard and throbbing I had become. I saw the trail of fluid I had left on her abdomen and hoped I would not be punished. I did not cum thankfully, but hoped I did not cross a line.
This had not escaped her notice too.
“My sissy is so hard,” she teased. “My goodness look at it drip, you must be bursting inside. How may I reward you for being a good gurl?”
“Mistress, may I lick my fingers that pleased you, so I can taste you?” I asked timidly.
“You may,” came her reply.
“Thank you Mistress.”
I eagerly pushed the pussy flavoured fingers into my mouth. The aroma and sweetness of her sex delighted my senses.
“Is that all my Sissy needs?” she asked, staring at my oozing tool.
“Mistress, may I also cum?” I requested with a desperate tone.
“Yes Sissy, I will reward you, you have earned that,” came her soft reply.
"Touch yourself for me," she continued. “Stroke that oozing sissy clit until it explodes.”
Wasting no time, still licking her from my fingers, with the other hand, I began to masturbate.
"Come on," she encouraged, "milk that hot cream."
Quickly I began to get lost in my self-induced pleasure. The sight of my naked mistress and the scent and taste of her were dizzying. Deliberately I pumped my shaft from tip to base. It would not take long to bring this to a climax.
Jess was cupping her tits and watching me intently, her bare chest still slightly heaving from her recent frenzy. Her lips were parted with anticipation.
“Would Sissy like to cum on my tits?” It was less of a question and more of a command.
"Yes Mistress," I exhaled between short lusty breaths.
I quickly managed to position myself, knowing the eruption was imminent. With a last full stroke, my orgasm broke free and the first rope launched out of me, hitting her between her voluptuous breasts. I gripped the base with the next two jets landing on target and dripping from her nipple. The last blast, less powerful, reached only to her abdomen.
For a moment we paused. I slowed my breathing to survey the scene. My gorgeous wife had a puddle of cum between her perfect tits. More steamy nectar dripping from her left nipple and a small pool near her belly button.
"This is quite a lot of cum!" she exclaimed. “I am pleased to see you have not been cumming without permission!”
“Thank you, Mistress, I do want to be a good sissy.”
She flicked her eyes down at herself, then back to me.
"Then be a good Sissy and lick me clean," she said.
I knelt on the floor beside her, eye level with her chest. The small streaks of precum I left first were the most available so I traced my tongue over them.
Then I worked my way higher, lapping up the salty and slightly sweet creamy liquid, savouring the taste. I was enjoying this immensely and soon found myself sucking the cum from her nipple and breast. Having now pleasurably cleaned my Mistress I pulled my lips from her skin.
“Kiss me Sissy,” she said
I obeyed and shared the flavour of our pleasure with her.
“Good gurl. Now it's Saturday, let me get cleaned up. I want to take my Sissy Anne shopping. There are a few things she needs."
