The Awakening of a Sissy Pt. 04

After a long evening of studying, practicing, and of course grooming myself, I woke to a message from Mistress. The message read; Sissy Jolie, douche your pussy, bath yourself, and be ready to meet. Make sure you douche and your trainer is inserted. I'll be over around 11 and I expect you to be in matching bra, panties and your heels. Also, ensure your cocksucker lips have your lipstick properly applied.

My mind immediately began to race. Why was she coming here, did I do something to displease her? I found myself both nervous and excited knowing she was coming here. As the coffee was brewing, I spent time watching the cock sucking video. I still wondered where this was leading and if she intended me to do this to a man.

Soon after I was getting ready for my morning routine. I selected and matching pair of lace bra and skimpy thong panties that were a mix of pink and soft rose, with small pink satin ribbons. After laying out my garments I set out to properly prepare myself. I was intent on doing my best to impress Mistress Di.

Once I was douched, shaved, bathed, and oiled I prepared myself for my trainer. I was somewhat surprised at how easily my "pussy" accepted it's insertion. I momentarily reflected back on, how nice it felt to replace the void I felt when it was removed.

I took some time to look myself over in the mirror before dressing myself. Donning the bra, pantie and heels seemed almost natural, much like squatting to pee. I began to wonder why that was.

Looking at the time, I raced to apply my lipstick, before Mistress was to arrive. In my effort to impress her, I restarted the cock sucking video, in hopes of impressing her on her arrival.

Approximately 10 minutes later, I received a text. I'll be there in 5 minutes, really need your mouth, be ready! No sooner was she in the door she said "Jolie, get on the floor on your back." I was barely on the floor before Mistress hiked her sundress and was squatting on my face. Her bare pussy was soaking wet as she ground it into my mouth. "Get your tongue in there good and deep and enjoy my juices, my sweet sissy. Tongue me good, show me what a good and hungry sissy bitch you are for me."

As soon as she was on my face I felt her wetness, It seemed as if her juices were flowing or leaking into my mouth. The scent of her sex was extremely strong. Mistress ground her sweet pussy deeply into my mouth and she played with her clit. "Lick me clean like a good little sissy bitch" she screamed as she reached her second orgasm, clamping her legs tightly against my head.

Mistress continued riding my mouth as she peeled off her sundress, reviling her naked body. She road my face for what had to be 15 - 20 minutes, achieving a 3rd orgasm before beginning to relax.Mistress stayed on my face for a few more minutes, while i continued lapping up her wetness. After she came down from her final climax, she climbed off of me.

"Oh Jolie, you are becoming one wonderful sissy bitch. I am so happy with the progress you are making. You clearly enjoy eating my sweet Mistress pussy however, there is so much more you need to learn, to help you grow. While I look around your place, go wash your face and reapply your lipstick."

As I entered the bathroom, I looked in the mirror. My face was a soaked mess of pussy juice. My lipsticked smeared all over. Taking a wash cloth, I slowly began to wash my face. While I was applying my lipstick, Mistress yelled, "Jolie, get your sissy bitch ass over here in the bedroom right now!"

I raced to the bedroom, wondering what could possibly be wrong. While entering she yelled, "stop right there." "Why are you not waking the way I taught you, did I not teach you anything yesterday?"

"Sorry Mistress, I forgot in my rush to see what was the matter."

"That is no excuse Jolie, I told you attention to detail is important for a sissy. Now, explain to me way all these things that I got you are just laying around and not put away. Stockings over here, panties over there. And your new bras, seemingly tossed there. Tell me why they are not put away Jolie."

I am sorry Mistress, I haven't figured out where to put them."

"Get your sissy ass over here" she said as she took a seat in the love seat at the end of my bed. I slowly walked toward her as I tried to walk properly. I knew I was in trouble. As I reached her, she ordered me to pull my panties down and bend over her knees.

"Please Mistress, I'm sorry, I'll do better, please don't spank me."

"I said pull your panties down and get over my knees. You better do it now, if you know what is good for you." I kept saying "I'm sorry Mistress" as I slowly pulled my panties down.

"Get your sissy ass over my knees and accept your punishment. Get your ass up nice and high, it's getting a good spanking today."

Once I was over her knees she began to softly rub my bottom. "Now Sissy Jolie, beg me to punish you and give you a good spanking for failing to walk properly and take proper care of your sissy things."

Scared as I was the words just came out. "Please Mistress Di, please punish me for not walking properly and not taking care of my things. I know I deserve to be spanked and taught a lesson, to make me a better sissy." While I was totally ashamed, knowing I was about to be spanked again, I also found it quiet exciting, I enjoyed submitting to Mistress.

"Oh this spanking will only part of your punishment. Mistress is very displeased with you and you are going to have to work yourself back into my good graces. There will be 20 for not walking properly and 20 for not taking care of your sissy clothing."

It was clear that she was upset as the first smack landed, It was much harder then my previous spanking. By the 10th smack my bottom was burning and tears were welling up in my eyes. "Sissy's prides themselves in attention to detail at all times. Sissy's work to please their superiors. Cock sucking is an art and it requires attention to detail. You need to get this in your pathetic sissy mind"

Before it was done, I was crying and begging her to stop, while promising her I would do better. Mistress did not stop until all 40 smacks were complete. My tears were flowing nonstop, as I pleaded for her to forgive me. My bottom was on fire.

Mistress let me lay there for several minutes as I composed myself.

"I hope you know that I do not get of on spanking you, it's simply something you need, to become the best sissy possible" she stated. Now stand up and wait right here, I'll be back in a moment." When Mistress returned, she took several pictures of me.

When she was done she directed me to bend over the bed. While I was bent over she began playing with my pussy plug. She slowly slid it out and then back in. This was repeated several times. "Jolie, your pussy is adapting well to this trainer, I think I might move you up to the next size. Now pull your panties up."

After she was done, Mistress directed me to get a pair of scissors and some trash bags, reminding me to walk properly. When I returned and handed them to her, she walked me over to my dresser and had me open you underwear draw. She took out each pair and cut them up.

"You're a pantie sissy from now on. You do not deserve to wear Men's underwear. From now on it is only panties for my pathetic sissy bitch. Now that those are all gone, you have room for your panties. She went thru the remaining draws, disposing of a number of items because, they were in her view, to much of a male. With these extra spaces you now have room for your bras, stockings, garters and your nighties.

Next was my closet, where she disposed of all but 2 pairs of loafers and a pair of running shoes. "You will need this space for all the heels you will be collecting. We will work on the rest of the closet another day. Follow me back to the living room."

As I walked into the living room I saw a pair a pink satin shorts and a very flimsy pink lace tank top sitting on the sofa, along with a pair of pink sandals.

"Put those on Jolie, we have a busy day ahead of us." As I pulled the tank top on, I noticed it had a clear scent of perfume. It also exposed my midsection. The shorts fit quite snug while exposing some of my bottom and hugged low at my hips which added to further exposure of my midsection. I then slipped on the sandals and fixed the slender jeweled ankle strap.

"Let's go Jolie, we have places to go, things to do, and people to meet." I was shocked at what I had heard. "Mistress, I can't go out and let people see me like this. You're joking, right?"

"No Jolie, I am dead serious. If you want to continue seeing me, you will do as you are told. Now lets get going, we're almost behind schedule as it is." With that I walked out to Mistress' car, while worrying about what was about to take place.

As we drove away, it was silent for several minutes. I sat there wondering where we were going and who was going to see me dressed like this. I'm not sure if Mistress was being quiet because she was mad at me, maybe simply to allow me to ponder my fiat or something else.

Eventually she broke the silence. "See that pink purse in the back seat, grab it, it is for you. While it is small I did place a few things in there that are necessary for all sissies. Go ahead and look inside, I'm sure you will be pleased."

"Stuttering I said, "You want me to carry a purse now Mistress?"

Looking at me somewhat sternly she said, "yes Jolie, I want you to carry a purse, after all, you are a sissy wimp, aren't you Jolie?"

My head went down in shame as I stated, yes Mistress I'm a sissy wimp." I'm not sure if it was the spanking or other things that had happened, but I had come to realize that she was right, I was if fact a sissy wimp. I had just admitted it to her.

"While you may find it humiliating at first, which by the way is good for you, you will soon get use to it and find it handy to have.

When I opened it I found, lipstick, eyeliner, a compact, a small bottle of perfume and some eye shadow. Further down in the bag I found something that both shocked me as well as made me blush. There they were, a number of condoms. As I pulled one out of the purse Mistress laughed, "you never know when you might need them Jolie, best to be prepared. While you should not need them now, in time you will."

The conversation shifted to the cock sucking video.

Mistress was quite happy to hear that I had watched it several times and practiced on the cock she had given me. "You should keep watching it and practicing. You need to develop your cock sucking skills and technique is very import. Make sure you are thinking of it as a real mans cock."

It was becoming quite clear that she intended to have me suck a cock at some point. I was uncertain how I felt about that. A week ago, I would have said, no way. Now I was thinking, I might be willing to trying it, to see what it was like.

We had been driving a good 40 minutes when Mistress grabbed her phone and made a call. "Hi Cindy, I'm about 5 minutes out, we still set to go? Sure thing, see you soon. "We're going to my hairdresser that I told you about, she works from home. I told her all about you and she can't wait to meet you."

To say I was nervous would be an understatement. There was no hiding what I was wearing. The straps from my bra kept showing. I was certain my bra could be seen quite clearly through the flimsy top. The tight shorts seemed to be riding up the crack of my ass while holding my pussy trainer firmly in place. The sandals exposed my pink toenails.

As we pulled into the driveway, Mistress said, "I'm sure you are nervous Jolie, but everything will be okay. She is going to take care of your hair and and eyebrows. And, as a special treat, give you some piercings."

"Did you say my eyebrows and piercings Mistress. May I ask, what is she going to do with my eyebrows and what am I getting pierced?"

"Nothing to worry your sissy little head about Jolie. It' just your ears and your navel as well as touching up your eyebrows a bit for a hint of femininity. You need to start expressing some of your new found sissyness. Now grab your purse and lets get going sissy. Walk like I thought you."

We walked up to a side door and enter what was clearly her beauty shop. Mistress called out, "Cindy it's just us, are you here?" A woman in her mid-thirties came out from around the corner.

"Hi Di, good seeing you" she said as she gave her a big hug. When she stepped back, she looked over at me. "This must be the sissy you were telling me about, Jolie is it?"

"Yes Cindy, this is sissy Jolie, what do you think, can you do some work with her?"

"Let me look her over"she said as she started walking around me. She has great legs, nice body, and such a cute ass. Jolie is simply divine Di, where ever did you find her? While her hair needs some work, there is plenty to work with. This could be your best sissy yet. Let me give her a mani-pedi as well, I'll add it in free of charge."

"Just remember, nothing over the top with her hair and eyebrows. I want it just slightly feminine but not screaming effeminate, at least for now, Mistress told her with a laugh."

"Okay Jolie, follow me we have a busy 2 hours ahead of us." Cindy led me to a chair, took my purse and had me sit in a chair. Soon she was busy washing my hair and then conditioning it. She set out a bottle of conditioner and told me to use it each day.

As she worked on me, I reflected back on how they had referred to me as "her and she." Next she went to work trimming my hair. "I'm going to need to take off a few inches, we need to get rid of these dead ends. Don't worry, it will still be a below your shoulders," she told me. Soon after, she was putting some large rollers in my hair. "These will give you some very slight waves to your hair but nothing crazy,"

Cindy then led me to another seat, which had a hair dryer. Before turning it on she told me she would be piercing my navel while my hair saw drying. She told me not to worry, I'd only feel a slight pinch while she did the piercing.

While I was under the dryer, she returned with a tray and set it on the table. She lifted my protective apron and began to wash my navel area with alcohol. She then grabbed a tool and something else and then pulled the apron over her head to block my view. I felt something cold on my navel then a rather sharp pinch. There was a little additional discomfort and then she was done.

Cindy pulled the apron down and covered up my piercing before I could see it. As i sat alone under the dryer, my mind drifted off to the cock sucking video. I pictured the woman holding the flaccid cock, slowly stroking it and kissing and licking it before letting it slip into her waiting mouth.

I found myself wondering both if I could do it and what it might feel and taste like. I had never thought about this in the past and wondered why I was now. The only cock I had ever touched, was mine, and it was now my clitty, as well as locked up to boot. My thoughts were broken when Cindy shutoff the dryer.

She checked my hair in several places before letting me know all was good. I followed her back to the other chair. As I started to lift my protective apron she slapped my hand. "You have to wait Jolie, you only get to see the finished product" she said laughingly.

Cindy went to work brushing my hair and doing some additional trimming. Once she was done she did some piercings in my ears. She then went to work on my eyebrows. Next she worked on my toes and fingers, When she was done, I had fresh pink toenails and finger nails done in a clear coating.

I was led back to the waiting room where Mistress was on the phone. "I think this is what you were looking for with Jolie, what do you think Di? "With that, Cindy removed my apron and left me standing there. Mistress told the person on the phone she would call them back.

Mistress looked me up and down as she walked around me. "It's perfect Cindy, I knew you could do it. Just feminine enough for now, just that hint I wanted. Have you shown her yet?" There they were referring to me as "her" once again. Before I could say anything, I was walked to a large mirror.

When I saw the reflection I was in shock. There I was, me but not me. My hair had a softer look to it. There was some shape but not overly feminine. My eyebrows had shape, but also not clearly feminine. But, then there were my ears, they were double pierced. The upper piercing was a small pinkish red stone. The lower was a small diamond. When I looked further down, I saw the navel piercing. It was a dangling piece of jewelry with again reddish pink stones. That was very clearly very effeminate.

At the initial moment, I can not say if I was more humiliated or excited by my new look. The look certainly hinted at me being a effeminate. It became very clear, going to my gym was no longer an option. I stood there staring at my new self. I looked soft and femme and seemed to delight in the new look. Can this really be the real me, I thought to myself?

Mistress once again broke my thoughts. "Let's go Jolie, we have things to do" she said as she tossed me a trench coat. "Get rid of you blouse and shorts, where we are going you will not need them."

Once again, I was nervous, as Mistress drove to the next location. Again, there was silence for several minutes. "Mistress, may I ask where we are going?"

"Oh yes Jolie, we are going to an adult book store (ABS) as part of your punishment. You didn't think I forgot did you? I'm going to give you the experience of a lifetime while we are there."

When we arrived, she made me follow her into the store carrying my purse. I had attempted to protest but Mistress made it clear, I'd get another spanking or worse, never get to see her again. To further humiliate me, she led me right over to the sex toy section.

While speaking loud enough for others to hear, she began asking me questions. "Do you like this cock Jolie, wouldn't you just love to be sucking on a cock like that? Oh Jolie, look at this trainer, I bet you would enjoy this in your sissy pussy." This continued as she walked me all around the store while pointing out movies, books and magazines, as well as various pieces of clothing and other toys. It felt like everyone in the store was staring at me.

After we had walked all around the store, Mistress grab my hand and promptly led me toward the back of the bookstores hallway. "Let's go check out the action in the back area, I know you will love it Jolie. I cant' wait to show you off to all the men back there"

I felt very uncomfortable as we walked toward the back of the store. Having never been in a place like this, I was very nervous, due stories I had heard about these places. As we entered the dim lit hallway Mistress ordered me to remove my coat. My protests landed of deft ears.

Soon I was being paraded all around the back hallway in nothing but my panties, bra and sandals, while wearing cocksucker red lipstick. I was so humiliated. Blood had rushed to my face. Men were looking at me, some were smiling while some were laughing. Other were blowing me kisses as they rubbed their crotch.

While walking past a group of men, Mistress said, "there is a large booth over there Jolie, let's go visit it." She led me into the door saying in a loud voice "this is a perfect room for more sissy training." The room was larger then the booths. It contained 2 love seats, some chairs and a large screen TV that was displaying some porn.

As I was looking around Mistress pulled my hair back and tied it back with a hair-tie. When she was satisfied, that it was pulled back properly she directed me to get on my knees. As I knelt down, Mistress told me "this is part of your punishment Jolie, but also a good step forward in developing your sissyness. The humiliation you are about to experience will help strip away some additional manhood that you may have."