The Awakening of a Sissy Pt. 06

While still admiring myself in the mirror, I received a text from Mistress, that read: I am so happy to hear that you are embracing and accepting that you are and were always meant to be sissy Jolie. Let me assure you, I will assist you and help you blossom into the ultimate sissy that you are meant to be. In time Joe will be completely stripped away. You have well exceeded my expectations, for this early on. I will need to adjust my timeline plans for you.

Rather than being shocked at the text, I smiled knowing I wanted Jolie to grow. As I was reading the note over for the third time, my trainer was again starting to stimulate my pussy. Clearly it was set on a low level.

Another message arrived from Mistress. Set your alarm for 6 AM, you will need the extra time before meeting me at 9:30 tomorrow morning. Right now, I want you to lay down in your bed, face down ass up, and reflect on what a little sissy slut you were at the ABS. Remember what you told those men yesterday - Thank you so much for allowing me the pleasure of experiencing your beautiful cock, It was truly a wonderful experience, I hope we can do it again some time in the future. I will need to more properly thank you. Suck on your trainer as you reflect on you day as well as your words to them.

As I made my way to the bed, my pussy trainer began stimulating me at a higher levels. I grabbed my training cock and started sucking as the levels were increased. I did my best to reflect on the days events and what I had told the men as my pussy was being stimulated once again.

This went on for maybe 20 minutes before the pussy trainer finally stopped. I rolled on my side and tried to relax my breathing. My body was experiencing so many wonderful sensations.

A text from Mistress read: enjoy your night Jolie, you will have a busy day and night tomorrow. Listen to your audio and get some rest. I will text you in the morning!

Once I had composed myself, I set my alarm and started my audio. I was fast asleep in moments. Right as my alarm went off, so did my pussy trainer. Luckily it was at a low setting. I laid there for a few moments, while enjoying the sensation.

As i tossed back my covers I noticed my nightie. This immediately brought a smile to my face. It was so right for me, this is Jolie, this is me. I slipped to the edge of the bed, slipped into my slippers, and put on my short pink robe.

Oddly, rather than making my way immediately to the kitchen to make coffee, I first went over to the mirror to check myself out. My hair was a mess. I did my best to fluff it back up, while looking myself over. Taking my phone, I went to make some fresh coffee.

While the coffee was brewing, I put on some music and began walking around while paying attention to my body posture. It was becoming more and more comfortable to me, even with my pussy trainer softly going off. It was important that I get it down pat and make it totally natural.

After pouring my coffee, I brought my cup into the living room. As soon as I plopped myself into the chair, I realized how um-feminine my action was. I stood back up and began practicing how to properly sit in a feminine manner. Smooth the robe along my bottom, legs closed, carefully cross them. Rebuilding the new me was going to be an interesting task, and I looked forward to it.

Several moments later, my phone rang. "Good morning Jolie, how is my little sissy slut doing? I hope you are not having second thoughts, after yesterday's little adventure. I trust you are still motivate to blossom as Jolie. Are you enjoying the stimulation from your new pussy trainer? What has sissy Jolie been doing since waking up"

I gave Mistress Di a very detailed report about what I had been doing. She was especially impressed when I told her about my sitting realization. I was informed that more of Joe was about to be stripped away today and tonight. She told me I would have a far better understanding of my place by nights end.

Mistress gave me a number of instructions regarding my morning preparations. Beyond my normal routine, I was the charge my pussy trainer, shave my face twice, to ensure it was extra smooth. I was to wear only my short pink robe and my pink come fuck me heels when I came over. My robe could stay on when I entered, and I was to put on my collar before entering the living room.

As i went about my tasks, I found myself more excited then nervous about what Mistress had in store for me today and tonight. Curiosity built inside me when thinking about what Mistress meant about the night. This would be the first time I would be spending so many hours with her. With a smile on my face, I wondered how more of Joe would be stripped away and how I would better understand my place.

When I arrived at her house, I put on my collar and made my way to the living room. In my mind, I was thinking, I would soon be licking her sweet mistress pussy, which I looked forward to doing. That was not to happen today.

Mistress was standing there in a black robe, and heels much like mine but in black. While looking at me, she began to laugh. She walked up to me smiling. Jolie, you are a sissy now. You need to wear your robe, and other things in a feminine way. Men fold their robes, shirts, and jackets in this direction. You are so not a man, you should realize that by now. Yours goes the opposite direction, just like a woman would do. That is a sissy rule that you must learn to embrace.

After my robe was fixed Mistress had me follow her into the powder room. She had me remove my robe and handed me a can of deodorant. She told me that, from now on, I was to only use feminine deodorant with a flowery smell. Next I was sat in a chair, facing away from the mirror. Mistress soon began applying makeup to my face. She explained what everything was as she did it. I was told she would be giving me lessons very soon and that I should begin watching tutorials online. She paused for a moment, took her phone and my pussy trainer slowly began pulsating.

Mistress spent a good deal of time on my makeup and my hair. When she was done, she had me turn around and look in the mirror.

There was a stunning reflection staring back at me. I was shocked at just how feminine I looked. Clearly I would easily pass as a girl. I was seeing Jolie for the very first time.

"So Jolie, what do you think, do you like this look? I hope it makes you feel more feminine and sexy. This look will give you a better understanding of the sweet sissy you are going to become. What do you think?"

"It's amazing Mistress, I had no idea that I could look like this. I love this look. Now I really can see Jolie. Thank you so much Mistress."

Mistress laughed. "Jolie, we seriously need to work on that voice of yours. I want you to begin speaking in a more effeminate tone of voice. It will take time but you need to begin practicing."

Yes Mistress, you are right, I need to work on that." I did my best to use an effeminate tone. "Better" she said, "we will certainly work on it."

"Here, put on these stocking, garter, and bra and then your heels" I have a special treat in store for you, after I get some pictures." She had that wicked grin on her face.

As I dressed, I wondered about what the special treat might be. That wicked smile told me something was up. After I was dressed, she began taking pictures of me from all angles. As she did, she also turned up the level of my pussy trainer.

When the pictures were done, she had me put my robe back on. She had me follow her into the living room and told me where to stand. After taking another picture she made a call. "Everything is set, come down stairs to the living room and join us there" she said with her wicked smile beaming from her face.

Blood began rushing to my face, as I wondered who she was speaking to. It didn't take long for me to get an answer. Looking over at the stairs, I saw a man walking down. As he made his way down the steps, I noticed he was only wearing a short robe. He looked tall and well built.

As he walked into the living room he reached over to Mistress and gave her a deep kiss. When they broke their kiss, Mistress looked over toward me. "Jolie, this is Tim, Tim this is sissy Jolie. Tim has been following your training with the videos and pictures I have taken. He's become very interested in meeting you and helping me with your training."

"After our talk in the car, and your announcement about wanting to blossom, I decided it was time for you to meet him. Your training today will involve Tim. Tim is one of my favorite studs and well equipped to help. Now take off your robe Jolie, let Tim get a better look at you."

My hands were shaking as I tried to undo my robe. I knew that this was a turning point for me. Embarrassed, I slowly let the robe slip off of me. Trying to be sexy, I let it slowly drop to the floor. My head was down looking at the floor, shame passed thru my mind and body, along with a strong sense of excitement. Mistress made me slowly turn around, allowing Tim to look over my body.

"Isn't that an incredible ass Tim, looks so fuckable, doesn't it? This sissy bitch had no idea of her potential until I approached her. Jolie has quickly adapted to her new role and with your help we will expand her horizons. I locked up that pathetic little thing on day one."

"Jolie, look at at him, isn't he hot? He's such a stud. You should be happy that he is interested in you sissy. You know why he is here, don't you Jolie?"

I was certain I did, but was unsure how to answer. I simply responded "yes Mistress" while trying to use my effeminate voice.

"You do, do you Jolie? Tell us why he is here, and look him in the eyes as you do."

I struggled looking him in the eyes as I said, "you are going to make me suck his cock Mistress," using my best sissy voice.

Mistress let out a laugh, "yes Jolie, you are right, I'm going to have you suck his cock. As of today, you will officially become a sissy cock sucker, for the rest of your life. I'm certain you feel ashamed knowing what you are about to do but, this is a very important step in your sissification."

As she spoke she increased the level of my pussy trainer. " I am certain that you will come to like it very soon Jolie. I know you must be dying inside inside to see it, aren't you sissy? Ask Tim nicely if you can see it, and use your sissy voice."

I was trembling, both from nervousness and excitement. I wanted to not just see it, I wanted to experience how it would feel in my mouth. At the same time, I worried that I would now be known as a cock sucker.

Jolie was having no part in delaying things. Without a thought, I looked him in the eyes, using my sissy voice, while blushing, and said, "Tim, I would love to see your cock, I'm sure it is quite manly, may I please see it?"

"Oh Jolie, I'll be happy to show it to you," Tim said. "I so want you to see it and can't wait to have your sweet sissy lips wrapped around my cock and turning you into the cock sucker your are meant to be."

With that said, Tim opened his robe and let it fall to the floor. My jaw dropped when I saw it. Mistress was right when she called him a stud. I let out a "oh my god" the moment I saw it, blushing even more. Tim was totally flaccid, it was almost 6" and clearly thick.

Mistress used a few fingers to slightly lift it. "What do you think Jolie, do you like his cock? Does it inspire my sissy to want to suck it?"

Jolie was in full command. I knew I was being recorded and didn't care. "Oh Mistress that is a beautiful cock. It is so big and manly looking. I want to experience him in my mouth. I want to taste him and suck it."

Tim placed a hand on my shoulder and told me to get on my knees. I looked him in the eyes, then looked at his cock as I sank to my knees. This was the moment of truth, I thought in my head. Tim's cock was now inches from my face. My eyes were locked on it.

Mistress held it out to me. "Look up at Tim and tell him what you want to do and beg him to allow you to, and make sure you do it in your effeminate voice.

The words shamelessly poured out of my mouth. "Tim, I so want to kiss, lick and suck your cock and balls. My I please have your permission to do it? I so want your cock, may I please have it Tim? I'll do my very best to pleasure your manhood, Please let me."

Mistress placed her hand on the back of my head and moved me forward. "Kiss his cock Jolie, give it a nice loving sissy kiss." I wasted no time and gave his large lovely mushroom head a soft loving kiss, as I looked him in his eyes.

Mistress, directed me to kiss it all over, as well as his balls. As I was doing it she had me take it in my hand, the weight of it was astonishing. With it in my hand, I began to slowly stroke his cock, as I learned from my video. My kisses were stimulating him and it began to grow.

"Lick it Jolie, lick it all over, and don't forget about his balls" she ordered me. I ran my tongue all over his cock and balls. I was becoming more sexually excited. Soft moans of pleasure escaped my mouth. The warmth and softness of his skin, along with it's taste, was rather stimulation. My pussy trainer was only lending to my overall, sexually aroused state of mind. He continued to grow in my hand.

My tongue was lapping all over his growing cock. I was in heat, wanting nothing more then to please him and feel him in my mouth. I began kissing and licking him more and more passionately. The sounds from my mouth were of pure lust and passion. I continued stroking his manhood, amazed as it grew.

The level of my pussy trainer was again increased. "Oh Jolie, I can so see the joy and lust on your face, you look like such a sexy sissy slut enjoying that cock. Look how hard you made him, how big he is, all because of you" Mistress stated.

She was right, he was hard because of me and that made me happy knowing I was the reason. Tim was now erect, and nearly 10" of solid manhood. The weight and size and thickness of it, amazed me. He was letting out soft moans of pleasure.

My desire and excitement had me breathing more rapidly. I was shamelessly working my mouth all over Tim's cock. I was squeezing my cheeks on my pussy trainer as it vibrated, thumped, pulsed, and grew and shrank in my pussy. The sexual arousal was almost overpowering.

"Jolie, you have Tim all hard and excited, what are we going to do about that? You can't just keep licking and kissing it like a little sissy slut. Tell Tim and I what you want to do, now that he is all hard and ready."

I was so sexually stimulated the words just poured out of my mouth. As I continued stroking, licking, and kissing his cock i told Tim and Mistress, in my feminine voice, "I want to take him in my mouth. I want to suck his cock and pleasure it. I want to become the cock sucker I was meant to be and I want to make him cum in my mouth."

"Please Tim, please let me suck it. I need to have your hard cock in my mouth. I'll do a good job sucking you. Please?"

"You'er right Jolie, you need to take him in your mouth. It's time for you to be the sissy cock sucker you need to be. Show Tim how much you learned from your training video. I want you to very slowly let Tim's cock slip between your lips, as you look up at him."

I didn't need to be told a second time. Without a care in the world, I positioned myself at the head of his cock. The moment of truth had arrived.

My mouth slightly opened. Ever so slowly I began to let his beautiful big fat mushroom head slip between my lips. I was amazed at how nice that smooth velvet head felt as it slipped past my lips.

As soon as it entered my mouth, I teased the tip of him with my tongue. I wrapped my lips around it as I moved my head down a little more on him. As thick as he was, I found it enjoyable having his cock in my mouth.

After pushing my head down a little more, I softly started sucking on him. My courage built, as I started bobbing my head up and down. Feeling that warm thick throbbing member in my mouth felt so right. Using my hand, I slowly stroked him as I bobbed up and down on his cock.

Tim let out a soft moan of pleasure and softly placed his hand on the back of my head. "Oh fuck," he sighed, "this sissy bitch has a great mouth. I'm going to so love using it on a regular basis. I'll groom this slut to be a great cock sucker."

Mistress leaned in and kissed me on my cheek. "Congratulations Jolie, you're officially a cock sucker now. I am so proud of you. You look so lovely with that cock in your mouth. I think you are a natural cock sucker."

I did my best to say "thank you Mistress," with a mouthful of cock. Oddly, I felt a sense of pride hearing her declare that I was now officially a cock sucker. As I continued sucking his cock, I thought to myself, I'm a cock sucker and I am proud of it.

Soft moans of pleasure escaped me as I worked on his cock. Tim started to softly apply pressure to the back of my head. He encouraged me to take more of him. Cautiously, I let him in deeper and deeper. My mouth was full of a throbbing cock, and I was truly enjoying it.

"That's it Jolie, suck my cock like a good little sissy slut. Be a good sissy bitch and use your tongue more. Take more of it, you fucking cock sucker. Oh fuck, you have a good mouth. You're going to be a great cock sucker before I'm done using you."

As humiliating as his words were, I was encouraged by them. It was true, I was a cocksucker now. I wanted to make him feel as good as possible. My mouth was stretched and full of cock and I was enjoying it. The sensations of my pussy trainer were only adding to my lust and desires.

"Jolie is really enjoying herself. I can see that by the look on her face Tim, she really likes your cock. In time, our sweet little cock sucker, will be deep throating you. She's a natural cum slut. I can already see it," Mistress stated.

Slowly but surely, I had worked in enough cock that I could feel it hitting the back of my throat. Tim's moans were getting louder and more rapid. He continued calling me names while encouraging me to suck him. For some reason, I started crying, I'm not sure if they were tears of shame or joy. I knew I liked the feel of his cock in my mouth.

Tim's hand began forcing my head up and down at a faster pace. His hips began pumping his cock into my mouth in rhythm to my head. "Yes Jolie, suck my cock bitch. Keep going, I'm getting close. I'm so going to cum in your mouth slut and you are going to swallow it. It might be the first of the day, but I assure you I'm going to be giving you more today and tonight."

As I continued sucking, I took in Tim's words, more today and tonight. I felt giddy hearing I'd be doing it more and getting more cum. I had a feeling it was going to be a long day. While I had never had a man cum in my mouth, I was so wanting it. I only hoped I'd like it. Like it or not. After all, it was a sissy's duty to swallow and I was now prepared for that.

A minute or 2 later I felt Tim's cock swell and twitch. FUCK YES, I"M CUMMING. Sure enough, his cock erupted in my mouth. Shot after shot of his warm thick man seed began filling my mouth.

"Jolie, don't waste that gift, hold it all in your mouth. I want a good picture before you swallow it. Lets not be wasteful mind you," Mistress told me.

Tim must have shot 6 or 7 ropes of his man juice in my mouth. I struggled holding it in, some leaked down my chin. When Tim was done, he removed himself from my mouth. Mistress told me to open up wide for the picture.

She took several photos and then directed me to close my mouth. "Hold that cum in your mouth and swirl it around in your mouth. Savor the taste of his cum before you swallow it Jolie."

I did as she said, I swirled it around for a few moments. It was thick and kind of salty tasting. I instantly knew I could handle it, and even enjoy it. After savoring it for a few moments, I swallowed it down. I smiled, knowing I had just swallowed my first load of cum. I was already looking forward to more.