Jess took a few steps back to consider the answer to her question. As she did I was reminded of just how strongly I was attracted to her. 

My beautiful wife stood 5’6 and weighed 145lbs. Fair skin perfectly molded to her curvaceous figure. Generous D-cup breasts were lightly freckled with dusky pink areolas and nipples that stood out well over a centimeter and begged for attention. Her firmly toned bubble bum and shapely thighs always drew the attention of men when she wore skirts. A pretty oval face, dotted with freckles, generally carried an expression that revealed her charm and intelligence. Straight layered long blond hair framed her almond-shaped dazzling green eyes and a button nose that sat atop her luscious dark pink lips, which were just now curled into a mischievous smile.

Jess had always been sexually adventurous so there was no shock in her reaction and what was unfolding between us now. I was both thrilled and relieved that she had discovered and confronted me. As I thought about it, I had typically been happy to let her take the lead in our sexual activity. There had not been a conscious decision to be submissive when I was plain old Robbie, it was simply the natural course, Jess took the lead and I happily followed. 

Now, however, the dynamic had taken a distinct turn. Jess was in control, and she had started this confrontation with a plan. I was, by my very recent admission, a sissy, and sissies must be dominated. A fact that had not escaped my wife.

“Take a seat,” she commanded, moving toward the stool at her dressing table. “If you want to be a sissy girl, I am going to have to help you with clothes, makeup, and so much more.”

She winked, smiled a mischievous smile, and went to our closet while I sat facing the mirror. The image I saw was not unappealing yet it was lacking. Jess was right, I needed help to become fully feminized.

The next reflection in the mirror gave me goosebumps. I squirmed in my seat as tingles of both trepidation and excitement washed over me. She had put on patent leather knee-high boots with stiletto heels and a lavish red satin open underbust corset. Her perfect breasts and hard pink nipples were proudly exposed. The addition that created the greatest stir however was the black leather harness worn on her hips, fitted with a black silicone dildo. She smiled seeing my reaction, knowing I was mesmerized by the 6.5-inch appendage, complete with veins and ridges that bounced as she approached me. 

Stopping directly behind me, she leaned forward, grazing her swollen nipples on the bare skin of my back. Her hands slipped around my shoulders and over my upper chest, letting her fingers disappear inside the cups of my bra. My every sense was heightened at her touch and jolts of arousal when straight to my swelling cock as she teased my hard nipples.

“I’m going to let you cum in your pretty pink panties,” she whispered in my ear. “As long as you do as I say. Tonight we are going to give you a makeover, and you will become a true sissy. Is that understood?”

“Yes,” I said hoarsely, unable to say anything else. In truth, I had concerns about her plans for her silicone cock.

“That was not very convincing.” Her mouth was on my ear, taking an aggressive nibble at my earlobe. “I want you to address me as ‘Mistress’, and I want no doubt that you are going to obey, is that clear sissy?”

“Yes, Mistress!” I said with more conviction.

“That’s better,” she breathed into my ear, her nipples teasing me further. “We will be able to have plenty of fun as long as you’re a good girl. However, now that we know how you will address me, how should I address you? I could simply call you sissy, and I may more often than not. But I do think you should have a girly sissy name too, don’t you?”

I had not thought of that, but it sounded like a great idea. My sissy persona did need an identity.

“Yes, Mistress,” I said eagerly.

“Do you have any ideas? Would you like to choose your girly name, or should Mistress Jess choose for you?” She asked.

“If it is ok Mistress, I would like to be called Anne,” I suggested, "I think it's a pretty name."

“That is a pretty name,” she agreed. “Why did you choose that name?”

“Mistress, I am afraid this will sound silly," I explained, "but when I was young, my mother had a wig of long, curly, red hair. We had been playing dress up, and she wore a fancy dress, pearls, and her beautiful red wig. She looked so pretty in it. I innocently asked her if I could try it on, and she agreed without hesitation."

"Was that the first time you wore a wig?" Mistress asked.

"Yes Mistress," I replied, "I put it on and liked how it looked. My mother told me I looked like 'Anne of Green Gables'. Right then, part of me wanted to be just like Anne."

Mistress smiled grabbed my face in her hands and kissed my lips deeply letting her fingers slide inside my panties and caress my swelling sissy cock.

“Anne sounds perfect,” she said with approval.

 I moaned into her mouth as I kissed her back, instinctively reaching to caress her exquisite, soft tits. My fingertips had just begun to roll on her pretty pink nipples when she withdrew her hand from my panties and slapped my hand away.

“Did you receive permission?” she said sternly, pulling away from my lips. “From now on Anne, you need permission to touch your mistress, permission to touch yourself, and permission to cum.”

“Now, as I said, if you are a good girl and serve me as I say, I will make you cum in your panties. Would you like that, sissy?” 

Her dominance seemed to come so naturally, almost out of nowhere. Equally so was my immediate desire to serve and please her when dressed as a girl.

“Yes, Mistress!” I declared. “Your little sissy would love to serve you and would be grateful to cum in my panties.”

Satisfied with my answer, she smirked and walked back to the closet, swaying her ass for my viewing pleasure. Gone for only a moment, she returned with my wig of red hair and a pair of pink slingback strappy kitten-heeled shoes. I had almost forgotten about the faux cock strapped to her hips, but there it was bouncing playfully toward me once again.

“We are going to make you over into ‘Anne’ tonight.” She said with purpose.

I was delighted on the inside and, if the growing bulge in my panties was any indication, on the outside too. Mistress stood behind me and fixed the wig in place, fluffing and adjusting until she was happy with the look. 

“Anne, you should put on your sissy shoes now.” She said as she looked through her makeup case for the items needed to complete the look.

“Yes, Mistress,” I replied, feeling delighted to hear my sissy designation, and eagerly bent down to slip on my newest accessories.

As I was admiring my shoes, a perfect fit, it occurred to me that this had been well planned. The underthings, the shoes, her reactions, and total comfort and skill at dominating her freshly revealed sissy servant.

“Mistress,” I spoke meekly, “may I ask a question?”

“Yes, you may,” she replied with a knowing smile.

“When did you purchase these shoes?” I paused then continued, “I mean what I am saying is you must have known before today to have all this prepared, how long have you known?”

Before her answer came, she turned back toward me with a variety of products from lipstick to eye makeup and more.

“Hold very still,” she admonished as she began applying eyeliner to my left eye.

“Well Anne,” she said quietly, almost whispering, continuing to apply beauty products, “I had known Robbie had been playing at being a sissy for several months now. He, like many men, are not always as careful as they believe they are, and rarely cover their tracks as well as they think they have.”

Her hands skillfully applied mascara and next a copper-toned eye shadow around my bright blue eyes.

“I began to notice my panties, which had been discarded the day before, back on top of the laundry pile, and on one occasion the inside was still wet with fresh cum. Later Robbie neglected to properly close a website where he had been viewing sissy porn clips,” she added, “I did not take a genius to connect the dots from Robbie to the sissy we now know as Anne.”

“Thank you, Mistress,” I mumbled, feeling ashamed at my clumsy efforts to hide. “Thank you for understanding.”

“I appreciate your words, sissy,” she said with a tone of mild aggression, “However, it will take more than words to show your full appreciation for your mistress, now hold your mouth closed but relaxed while I apply your lipstick.”

When she was finished I looked in the mirror and was astonished. Complete with a wig and some skillfully applied cosmetics I was changed. It was clear more was needed for a complete transformation. I was sure that would come in time. For now, I was impressed at how quickly I had become pretty. 

“Stand up,” Mistress commanded. “Let’s have a look at you.”

Slowly, I stood pleased with what I saw in the mirror. I had worn heels briefly before, but now was grateful Mistress had selected shorter heels for my shoes.

“Take a walk,” she said, gesturing with a twirling motion. “Give me a spin and show me just how sexy of a sissy you have become.”

I walked to the center of the room, at the base of the bed I spun on a heel, feeling my wig flair. I caught a glimpse of my outfit as I spun back forward, making a note that this would look much better with breast forms, yet still impressed with how I was altered.

“Oh, you are a pretty girl Anne! I can see you are pleased by the elated look on your face.” Then, frowning slightly, she added, “But sissies are meant to serve, are they not? I think it is time you serve your mistress! Sit on the floor where you can worship me properly!”

Without thought or delay, I sat right where I had been standing, my back to the foot of the bed. 

Mistress Jess smiled devilishly and slowly walked in an arc toward me, staring into my eyes without so much as a blink. When she was directly in front of me, her black appendage at my eye level, she spun on her stiletto heels.  Now inches away from my lips was her wonderfully shaped ass. Perfectly round, creamy white skin, there on display, teasing me, taunting me. Yet I resisted the urge to touch without invitation.

After an extended pause, Mistress spread her legs wide and slowly bent over showing me her lovely pink rosebud. My appetite for eating her ass was well-established. This was, no doubt, a test of my obedience. The scent of her sex surrounded me. My cock strained the stitching of my panties as slowly her ass moved closer to my face. 

“What a patient good girl,” she cooed, “you will devour my ass, but only with your tongue, no fingers.”

Without an answer, I lowered my face to meet her. My tongue slid from the bottom of her pussy up over her back passage to the top of her crevice. Savoring every sweet inch of her flesh. She sighed and I knew I was pleasing her, however, I also knew she wanted more. The assignment was to thoroughly probe her ass, and I was up for the task.

Precum once again began oozing from my aching, rock-hard sissy tool. I should have been worried that this might displease my new Mistress, but my focus was on my task and the tasty meal in front of me. I flicked my tongue back down to her entrance and slowly pushed inside her. 

Yes, that’s it sissy, give my ass a proper tongue fuck," she said as she pushed her ass backward, taking me deeper.

I responded eagerly, welcoming her, delivering my tongue as deep as possible. Now she countered by bouncing her delicious ass gently up and down, making my tongue wiggle inside her as she squealed with delight. She was clearly in charge, my head was pinned to the bed, but that was perfectly fine. I was blissfully feasting on her rosy buttonhole. 

“Finger my cunt, sissy,” she demanded, seemingly out of nowhere. “Make me cum on your fingers while you tongue fuck my ass!”

I was in no position to argue and would not have in any case, I was in my place, happily worshiping my mistress.

Now with permission, my hands could be used. I reached between her thighs, found her drenched labia, and plunged two fingers inside. Instantly her hips began to buck mashing my face and riding my fingers hard, so hard my tongue could not remain in her rear. That no longer seemed to matter, she had other needs to satisfy. My other hand found her clit and stroked it as she vigorously bounced off my fingers. Moans of her pleasure filled the air. 

The moaning became more of a low growl, her breath shortened, her knees quivered and she drenched my fingers with an orgasm.

“Your such a good sissy for making mistress cum!” she screamed, nearly collapsing onto her knees.

 We both took a few moments to catch our breath. My mind was spinning with the entirety of all that had just taken place. Once Jess regained herself, she stood pointing her silicone cock in my face.

“Now maybe it's Anne's turn to cum,” she said friskily. “Should I let my sissy cum in her panties?”

She looked down at my pink swelling groin. 

“You look very wet sissy. Did you cum without permission?” she asked with a serious tone.

“No Mistress,” I answered honestly with a panicked voice, “it is that I have been so turned on and have been dripping precum while I served your beautiful ass.”

“Good answer sissy girl,” she said with a smile, “this is going to work out very well. So because you have been such a good girl you may cum in your panties.”

Mistress reached down and dragged her sexy fingernail along the lace of my pink intimates. Tracing the vein of my girly cock. A sigh of delight hissed from my lips.

“I want you to stroke my cock as I stroke yours,” she announced, taking my right hand and placing it on her strapon.

Reaching inside my panties, her hand rubbed my head and then slid down to the base of my cock. Using my precum as lube she began to pump it slowly. I copied the motion on her, slowly dragging my hand up and over the ridge of the head and back to the base. 

Instinctively I fell into matching the rhythm and motion she was giving my flesh. I became entranced, feeling her soft fist wrapped around my shaft, feeling mine wrapped around hers. My eyes fixed intently on the ridges at the head of her cock, and whimpering moans escaped my lips as I approached climax.

She of course had noticed I was captivated by her toy, just inches from my face. She tightened her grip on me and sped up her pace.

“Suck it sissy, you know you want to.” She teased

I didn’t respond, I was fascinated, curious, but hesitant. Her motion on my aching rod stopped.

“If you want to cum in your panties, you will suck my cock now!” Her voice charged with a dominance that thrilled and encouraged me.

I closed my eyes and gently kissed the tip of her sleek black dildo, taking the head into my mouth. My mind was racing, was I sucking a phallus-shaped toy strapped to my wife’s hips? Was I dressed in pink lingerie, wearing heeled lady's shoes a wig, and makeup? What had been a private fantasy, a secret life, was now an open reality.

My every sense was alive as I took Mistress deeper into my mouth. I have never had a cock real or otherwise in my mouth before, but I had thought about it. I pulled back, letting the tip slowly slide off my lips, then eagerly drove my mouth back to take as much as I could until I felt it hit the back of my mouth.

“Oh good girl,” Mistress said huskily, resuming her strokes on my girly shaft. “Are you sure this is the first time you have taken cock in your mouth, you appear to be a natural.”

The sensations of it all were incredible. Her playful encouraging dominance, my girly attire, her touch, and my mouth being fucked! I was a girl, being treated and used like a girl!

I worshipped her black hammer. I perhaps lacked skill, this was new, but I was determined to please her with a vigorous display. I slurped and gurgled, taking as much as I could. Gagging a time or two but never slowing. It was wildly erotic!

My breath around Mistress’s shaft became shorter, my whimpering moans louder. She sensed the impending finale and kept a slow steady pace rubbing me from ridge to base, with firm strong strokes. The head of my pink love dart pressed into the lace.

“Anne, you may cum in your panties now.” Her voice was soft and sweet.

These words had barely left her lips, I looked down and watched. My glans, visible through the damp lace fabric. I groaned loudly watching the first burst of cum. Then another and another bubbled through the frills of the lace.

It was then I noticed, I had not stopped sucking Mistress’s toy cock. Through all my moans and excitement I had simply moved my lips to the base of the head and was sucking eagerly at the ridges. It seems I was no longer shy about having manhood in my mouth. I gently released my lips with a pop and looked up to see Mistress smiling.

“Thank you for letting me cum and for letting me suck you, Mistress,” I said sincerely.

“You earned your reward, sissy.” She returned.

Jess sat down on the floor beside me at the end of our bed. It seemed surreal. My lace intimates soaked in cum, her strapon standing proudly, always erect.

“This has been quite an evening of discovery,” I mused out loud. “I suppose there is more to talk about. We should figure out how Jess and Robbie move forward with Mistress and Anne?”

“I have some ideas about that,” Jess said with a wink as she reached for my hand and placed it around her ready hardness, “this is going to be fun!”