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.