The Awakening of a Sissy Pt. 03

As i was watching the video of Mistress and I for the 3rd or 4th time, my phone rang. "Hello my sweet Joey, how are you doing? I so enjoyed spending our time together, I'm so proud of you and the progress you are making. Are you still in your pink bra and pantie? That is such a sexy look for you, it makes you look so soft and feminine. Tomorrow we will build on your ensemble and other skills. Make sure you go to sleep in your bra and pantie while listening to the same link as last night. How is your bottom feeling after your spanking?"

"Hello Mistress, I too enjoyed spending time with you. It is so good to know that I made you proud of me and hope that I can continue to do so Mistress. I am still in my bra and pantie. My bottom feels okay Mistress. I'm looking at it in the mirror, it's still somewhat pink and warm."

I heard Mistress laugh, "Oh my you are looking at yourself in the mirror are you? I am so happy to hear you say and admit that to me. It is such a natural, feminine, and so fitting for a sweet sissy like you. That is something you should always do to help you grow into your proper submissive role. I can't wait to watch the video with you tomorrow, so many things to discuss. Enjoy your evening, get some rest, I'll see you at 11 sharp." She then hung up before I could get in a word.

As i continued looking at myself, I again began wondering, am I really a sissy? The reflection was certainly not that or a real man. Mine was more soft and somewhat feminine in feature. The pink bra and pantie along with the nail polish seemed to only enhance those features.

After a light dinner I set out to doing my bathing routine, starting with a shower to shave myself smooth. Next was the bubble bath, while soaking my mind drifted off to things with Mistress. I was now beginning to really enjoy the smoothness of my body and thought I might just stay this way even if things with Mistress should come to an end. Once I was toweled off, I began applying my scented body oil. The oil had such a pleasant smell and gave my skin a nice soft glow.

Soon I was back in my bedroom, looking at myself in the mirror. With my body oiled, I looked quite soft and even more feminine. Looking in the mirror, I took time to strike different sexy poses and examine my naked body before putting on my bra and pantie. Moments later there was a ding on my phone. It was a text from Mistress asking me to text my shoe size to her.

After watching some TV, I made my way back to the bedroom. I turned on my alarm and then the link, the soft voice came to life. Soon I was fast asleep. My sleep was broken to the sound of my alarm.

Making my way to the kitchen, I started a fresh pot of coffee. While it was brewing I sat and watched some of the video of Mistress and myself. After pouring some coffee, I returned to watching the video. There I was sucking on the dildo, as Mistress slid it in and out of my mouth. I thought to myself, I'd do that again if she wanted. I then wondered where that thought came from.

Once bathed and oiled I began to get dressed. Mistress sent me a text directing me to wear only a tank top and shorts over my bra and pantie, along with a pair of slip on shoes. I selected a lite green tank top and my black running shorts, and tan loafers. Once dressed I looked myself over before heading over to meet Mistress.

Again as I approached Mistress' driveway, the same car was pulling away. Walking in, I removed my outer cloths and place my collar on before joining Mistress in the living room. My plan was to ask about the car but I was quickly on my knees servicing her pretty mistress pussy at her direction.

The dildo soon came into play. She had me work it into her, getting it all wet and sloppy, then directing me to lick and suck it clean. she insisted on doing this over and over again, while encouraging me to take more and more in my mouth. "That's it Joey, make me proud of you and suck it like a good little sissy bitch. A sissy most know how to properly use their mouth to give others pleasure. I like the way your mouth naturally opened as I placed that cock to your mouth. Now, thank me for allowing you to suck that cock with my sweet pussy juices on it and beg me to let you do it more! Beg me to help you and train you to become a better sissy bitch"

Without giving it any thought I complied with her wishes.

"Thank Mistress for letting me suck that cock with all your wonderful sweet mistress pussy juices covering it. Please let me suck it more Mistress. Mistress I beg you, help train me to be a better sissy bitch."

"Stand up Joey, and strip for me sissy. It's time we advance your sissy training." Once I was naked, Mistress began looking me over. She began toying with my cage. "Tell me what is locked up in here sissy." "My clitty is locked in there Mistress"

"That's right sissy, it has to be a clitty because that pathetic little thing could never pass as a cock. It will never satisfy a woman. A woman whats a man with a real cock, one that can please her, one that fills her when he is inside her. This you must come to accept, my sweet sissy. Come with me and bend over the arm of the sofa. Open you legs and reach back and spread your cheeks open so I can examine you."

"Yes Mistress," was all I said as I did as I was told.

"Much better then yesterday, I expect you to keep yourself like this at all times. Don't move, stay right where you are." When she returned I could see that she had a wicked smile on her face. I soon felt something cool being rubbed around my ass hole. "Now that you realize that you have a clitty, you must also learn that this is now your pussy. You will from now on refer to it as your pussy. Do you understand me?"

"Yes Mistress, it is my pussy Mistress." I felt something being pressed to the opening of my "pussy" it felt somewhat hard. "Relax sissy, this is just a small pussy trainer, you will soon get use to it." I felt it being pressed further and I then opened up and it slipped inside me.

My "pussy" seemed to have clamped around it, holding it in place. "Very good Joey, it's in and will stay there for now. A good sissy appreciates having her pussy being plugged. In time you will also. Now, thank me for plugging your sissy pussy."

I didn't know what was happening to me. A feeling of embarrassment and humiliation past thru my mind, I hadn't resisted her at all, I willingly let her plug me. "Thank you for plugging my sissy pussy Mistress" was the only thing I said.

As I followed her back to the center of the living room, I noticed that the plug made me walk somewhat differently. "Joey my sweet sissy. I have decided that I am going to mold you into the perfect sissy bitch. Not a frilly sissy but one far more sensual and sexual. I will so enjoy taking you down this path and I know you will do your best to make me both happy and proud of you. So, with that in mind, I have decided it is time to give you a feminine name and get rid of Joey. From now on you are Jolie! What do you think of that Jolie, I think it is very fitting for a sissy like you. Do you like your new name Joiie?"

"Yes Mistress, I like the name Jolie, thank you so much for the name, I agree that it is fitting for me."

"Good I'm glad you like it Jolie, it's time to begin improving your sissyness, follow me." Mistress led me down a to a room that appeared to be her own personal gym. Wait here, I'll be back in a moment."

When she returned, she handed me a very skimpy red and pink 2 piece bikini. "slip into these and lets get some color to your skin tone." The bottom was a high cut thong and the top was at best a band aid covering my nipples. Handing me a bottle she told me, "put this on all over, just lightly, and try not getting it on your new bathing suit." She assisted it putting some on my back. She proceeded to open a tanning bed and had me get in. Once I was comfortable she told me to relax and enjoy. She handed me some air buds and told me to enjoy.

Once again there was a soft voice telling me to relax and clear my mind. the last thing I seemed to remember was the warmth of the lamps coming on. I awoke to Mistress opening the top of the bed and shaking me awake. "Wake up Jolie, enough tanning for today. Get up and lay on your back on this bench, I really need your mouth right now."

No sooner was I on the bench, Mistress straddled me pressing her sex to my mouth. I felt the plug pressing in my "pussy." Get your tongue in there Jolie and lick me good. I could tell she was really heated up, she was soaking wet. Her sex smelled almost oddly strong. I felt her juices leaking into my mouth as I lapped up her sex. She was grinding her pussy into me. "Yes sissy Jolie lick me good, get all that juice out of me. Make me cum!"

My face was soaking wet by the time she had climaxed. I continued licking as her climax flowed into my mouth. She stayed planted on me face as her climax began to subside. As she got up, she helped me to my feet. "Lets get you out of your suit and take a good at you."

As I was getting out of the suit Mistress giggled, "oh yes, you look so sissy like that for sure. Follow me over here." Leading me to a mirror, I saw what she had giggled about about. I clearly had tan lines showing I had been tanning in a 2 piece bikini. Where my skin was exposed I had a reddish pink color to my skin. Where I was covered, I was pure white. This was clearly the look of a sissy.

"You look wonderful Jolie, so feminine and yet so sissy like. I love it, and I know others will also. We must get you more color as time goes on. What do you think?"

While looking at myself, I told her, "I clearly look like a sissy with these tans lines Mistress," I said smiling. "I can't go to the gym looking like this. I'm not sure what I'm going to do about that."

"Soon we can workout together, I'll show you exercises to help you build on your feminine shape. I'm going to make you into one Hot sissy. Everyone will want you. Now lets get you showered so we can continue your training." She led me to a shower. Handing me a shower cap, "put your hair up in this so it doesn't get wet."

Once I was toweled off, Mistress handed me some scented oil to put on my skin. "We need to keep you smelling good and working on softer skin. Now this is how a sissy wraps a towel on their body. A man warps a towel around his waist. A sissy wears a towel like a woman, you need to get use to it Jolie. It is all part of accepting that you are in fact a sissy!

Come over here and let's get some lipstick on you. Watch how I do it, so you get use to how to apply it. This cocksucker red looks so good on you, both feminine and yet so sissy. You can keep this tube as your own. Follow me, I have some new things for you to put on. Wait here in the living room."

When Mistress returned was was carrying a shopping bag which she placed in a chair. "I was out shopping yesterday and decided to pick up some things for my sweet sissy Jolie. Lets get you into this garter belt first," she said with a smile.

The garter was a lacy pink with pink ribbon bows. It was quite delicate and clearly very feminine. once that was on she handed me a matching bra to put on. Once it was adjusted it seem to push my breasts up, almost giving me a bit of cleavage. Mistress then had me sit down and instructed me on how to properly don my new pink stockings and attaching them to my garter.

Next I was handed a matching thong pantie. The string of the thong slipped between my cheeks and seemed to aid in holding the plug in place. Mistress explained that it was always best to wear panties over the garter to allow for easy removal. Mistress next handed me a pair of heels. She told me the heel was low, but a good training pair for a sissy.

Mistress took a moment to brush my hair. "We will need to get you to my hair dresser and get you on a good hair treatment. It will help make your hair softer and more feminine. It will also add a nice shine to it."

Next, Mistress had me walking around the living room area, She was instructing me on how I should walk properly. head up, shoulders back, back straight, look ahead not down, smaller steps like a woman, and let my hips naturally sway, were all part of the instruction. I don't know why, I was taking everything in like a sponge. I was drawn toward her every word. A part of me knew I should be resisting, yet I wasn't.

As I was practicing my walk and posture, Mistress had taken the dildo and was using it on herself. She soon noticed me looking at her and removed it from herself. Smiling she said, "it looks like sissy Jolie wants something. Perhaps you would like to taste it and suck on it Jolie. Is that what my sissy wants to do?"

Not wasting a moment I quickly responded, "yes Mistress, I want to lick it and suck it. I so enjoy tasting you. May I please do it Mistress?" I walked over and knelt in front of her, opening my mouth as I did.

Mistress smiled and held it out toward me. "Okay Jolie, show me what a good sissy you are. Wrap those cocksucker lips around this cock and show me how much you enjoy sucking. While moving toward it I simply said "yes Mistress" before taking it in my mouth. She held it and worked in and out of my mouth.

"A good sissy prides herself on learning how to be the best cocksucker she can be. Do you want to learn to become a good sissy cocksucker sucker for your Mistress and make me proud of you Jolie?" She withdrew it from my mouth. "I'm waiting on an answer Jolie, do you want to learn to become a good sissy cocksucker sucker for your Mistress and make me proud of you?"

I so wanted her to be proud of me, my mind was racing, would she really want me to suck a mans cock or was she just teasing me. My thoughts were broken, "Jolie I'm waiting, what is your answer?" The words came out before I realized. "Yes Mistress, I want to learn to become a good sissy cocksucker for you Mistress and make you proud of me?"

As soon as the words were out, my mind began to race. Why did I say that, is that what I secretly wanted, could I do that? While I was thinking, Mistress had worked the dildo inside herself several times before placing it to me lips. "Open up sissy, lets work on your sissy cocksucker skills. Suck it nicely, think of it as a real mans cock and you so wanting to please him. You want to show off your sissy cocksucker skills for him."

"You want to worship it, giving him all the pleasure you can. Kissing it, licking it, and sucking it. A good sissy bitch proudly works for her reward of his wonderful cum filling your mouth for you to swallow. I'm going to make you the best sissy cocksucker ever."

I was totally caught up in the moment. I was licking, kissing, and sucking on it, while trying to imagine it as a real mans cock. I listened to Mistress as she coached me on the proper way to suck a cock, I was especially pleased by hearing Mistress tell me how proud I was making her, and how good a job I was doing.

Twice during my lesson, Mistress stopped me from sucking on the pretend cock. She handed me a compact and the lipstick. She continued coaching me on how to apply my sissy cocksucker red lipstick, then getting back to my lesson. This went on for at least 30 minutes. Mistress then had me worship her pretty mistress pussy until she reached her climax.

My training returned back to practicing how to properly walk and hold my posture. I was becoming quite accustomed with Mistress calling me both a sissy as well as Jolie. This portion of the training went on for perhaps 20 minutes before Mistress had me sit down with her on the sofa.

Once I was seated Mistress moved closer to me and wrapped her are around my waist. Giving me a soft squeeze, she said, "Jolie I am so happy with the progress you are making, you make me proud to be your Mistress. From your actions, I can tell I was right to groom you as my submissive, I think you are coming to appreciate your role and recognize that this is your true place in life. My desire for you, is for you to become the ultimate sissy, totally stripped of any perceived manhood."

"I want to mold you into a soft, feminine, sissy sex toy. One who knows her place and fully embraces it. I know that at times during your training, you will be very humiliated by some of the things you are going to be required to do for me. While humiliating, they are very necessary steps, to get you to where you need to be. You have to know, it will make me very proud of you. I really want to guide you on this journey, are you ready and willing to do it Jolie?"

While she was speaking a video of our days activity played on the large screen TV.

My head was spinning with all kinds of thoughts. I so enjoyed spending time with Mistress, It was nice hearing how proud she was of me. She was right, I was embracing this submissive role and how it was making me feel. I knew if I turned her offer down, it would be the end of spending time with her. The words just came out. "Yes Mistress, I really want you to guide on this journey you are talking about. I want to make you happy and I do accept my role as your submissive sissy."

No sooner had I answered, Mistress gave me a big hug and kissed me on my cheek. "I was so hoping that this would be your answer. You have made me very happy to be your Mistress. I'm so proud of your decision and I know in time you will come to accept that this is the best for you."

Mistress momentarily stepped away, returning with a bag. "I picked this up for you in hopes that you would accept my offer. This running suit will cover you up and allow you to keep your sexy undergarments on for the drive home. I hope you like the color, it's soft pink. I think it is the perfect color for you," she said while handing it to me. "There are other things in the bag as well, you can open them when you get home. Lets get you dressed, so you can get on with your sissy day."

Unlike the previous days, Mistress was gracious enough to escort me to the door. I removed my heels and slipped them into the bag as directed, I then stepped into my shoes, and removed my collar, placing it on the table. As I was getting ready to leave, Mistress gave me a big hug, telling me how proud of me she felt. She gave me another kiss on the cheek before say "enjoy your day Jolie!"

I carefully drove home while thinking about all the various things that had taken place. I was anxious to find what other wonderful things Mistress had for me in the bag. As I was pulling into my driveway, my phone ding with a message from Mistress. It read, as soon as you are home I want you to apply your lipstick. I also want you walking around in your heels paying attention to your posture.

As soon as I was in the house I raced to my bedroom and removed my running suit. With my heels on, I went to the mirror and applied my lipstick. Standing there I examined myself from every possible angle. Thinking back to when Mistress told me, you know you're a sissy I smiled. I clearly looked every bit the part.

Curiosity took over, I had to see what was waiting for me in the bag. First thing was a box containing an enema bag. As I pulled it out I saw that Mistress had written on the bag, sissy douche kit. Next I found a few new pairs of matching bras and panties.

There was next a very realistic looking dildo cock, followed by a few bottles of lubricant. Lastly, there was a DVD titled The Art of Cock Sucking, with a note attached saying text me when you have gotten to this. The text was promptly sent to Mistress. Her responding text simply read, Study the DVD and Practice, douche before you bath and reinsert your trainer before bed! Will text you in the AM.