The Awakening of a Sissy Pt. 02

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Mistress continues training the beta male.
3.5k words
4.6
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Part 2 of the 11 part series

Updated 06/09/2023
Created 12/25/2019
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As I drove away from her home, my mind was racing with thoughts of what had just happened earlier. The sweet odor of her pussy juices filled my nostrils. I could still taste her in my mouth. I was so overcome by the experience, I barely kept my mind on the road. Once I arrived home, I quickly stripped down to my panties. I had to see what they looked like on me.

I walked over to the full length mirror to see myself. The panties seemed to hug me like a glove. They were high cut and gave me a rather feminine appearance. The small cage was at best barely noticeable. I began to very slowly turn, while examining how they made my backside look. My face began to blush seeing how the panties made my bottom look firm, full, and round. I spent a good deal of time checking myself out from every angle possible, concluding that panties weren't so bad after all.

Standing back facing the mirror, I began to slide the panties down to see what the cage looked like on me. My little thing, "my clitty" could be see helpless inside the clear tube. The tiny pink lock was in sharp contrast to the clear tube. I was not sure exactly how I felt about being locked up but, if it pleased Mistress Di I would deal with it for now.

My phone began to ring, I quickly pulled up my panties and went to over to answer it. "Hello Joe, it's Mistress Di, I wanted to see how you are doing and let you know I was very pleased with you today. I'm so looking forward to seeing you again tomorrow and continuing with your training. What have you been doing since you left?"

"Hello Mistress Di, it is so nice to hear from you, I'm doing well. I am glad you were pleased with me today Mistress and look forward to seeing you tomorrow as well. I'm just hanging around and relaxing right now, not doing much of anything."

"Do tell your Mistress, what are you wearing right now. How are you dressed?"

Blood rushed to my face upon hearing her question. I was silent for a few moments wondering what I should tell her. Thoughts were broken on hearing "Joe, tell me right now, exactly what you are wearing and what you have been do?"

Ashamed and embarrassed, I slowly began to explain to her what I had been doing. She seemed to take delight in hearing me describe in detail to her what I had been doing. Laughingly she said "it's okay Joe, I'm glad to hear that you were doing that. Go back to the mirror and turn so that you can check out that sweet ass of yours. Do you see how shapely it is? It looks so fuckable, real girls would die for an ass like that."

Unsure how to respond, I simply said "Thank you Mistress, I glad you like it." I had never thought of my ass as being fuckable and I was kind of embarrassed by her statement.

"There is something I want you to do this afternoon, I will text you the instructions. Once you have reviewed them I want you to send me a text back saying you will follow the instructions in their exact order. If you are not willing to comply, simply send a sorry Mistress, we will be done, and never visit me again. I will be waiting on your response." With that she hung up.

Moments later the instructions arrived. At the mall, doing the following, in their exact order. 1) buy a pink satin satin sheet set 2) go to Bath and Body and purchase 4 rose peddle candles 3) go to Victories Secret and ask to see some of their pink nighties. When you find one you feel is extra sexy take a picture of it. 4) go to Macy's and buy a large bottle of scented Neutrogena Body Oil, and 5) go back to Bath and Body and purchase a large bottle of peach scented bubble bath.

After looking over the list and wondering what this was all about, I sent her a response, letting her know that i would do it. Soon I was on the way to the mall to begin my shopping. Deep inside was a feeling of both nervousness and excitement. As I was driving I wondered why she wanted me to pick these thing s up but, I also found my self wanting to please her.

The visit to Victories Secret was the most challenging of the assignments. The sale woman asked all kinds of questions. What is your girl friends size, he bust, her waist and so on? I eventually settled on a sheer pink teddy. Taking a picture, I told her I needed to consult with some friends before making the purchase. I left the store totally blushing.

Text - Hope you are enjoying your shopping, let me know when you are back at home, Mistress Di!

As I entered Bed and Bath the same sales girl from earlier approached me, "oh you are back, did you forget something?"

I told her that i had forgotten to pick up bubble bath. She seemed quite interested in finding out what I was planning on doing, and for who this was all intended fore. She wanted to know if this was for a special occasion with my girlfriend, what my plans were, and where we might be going? Unable to give a good answer I simply had her show me where to find the bubble bath. I could see a strange look, perhaps questioning, on her face as she rang me out.

Once I was back home and had the bags in the house I sent a text to Mistress informing her I was back. About 10 minutes later I received a text from her, directing me to 1) strip down to my panties, 2) send her a picture of the nightie I selected, 3) make my bed with the new sheet set, and 4) take a picture of it and send it to her when done.

Shortly after sending the picture of my bed, my phone rang. "Hello my sweet Joey, I am so proud of you for accomplishing each of your tasks. The pink bedding is so nice on your bed and so fitting for my sweet submissive. As a reward this evening, I want you to do the following; 1) take a nice shower and shave yourself smooth all over, 2) run a bubble bath and soak in it for at least 30 minutes while burning one of your candles, 3) while soaking think of all the things that have occurred since we first met, 4) once you have dried off apply the Neutrogena Body Oil all over your lovely body and 5) put your panties back on. I will send you a link that I want you to play when you go to bed. It will help you relax and get a good nights sleep. It is set to continue running all night so you should make sure your phone is plugged in. Enjoy your evening, I'll contact you in the morning."

Before I could say a word she had hung up. I stood there reflecting on the things she had said to me. Recalling that she had said she was proud of me brought a smile to me face. While I was not sure about how I felt about her referring to me, knowing it seemed to please her, I was willing to go along with it for now.

After my shower and shaving I began to draw my bath water adding in some of the bubble bath. I lit the candle and stepped into the tub. I didn't recall having ever taken a bubble bath since being very young. The combination of the warm water and the scent of the bubble bath and candle filled the room. I found it quiet pleasant and relaxing. I found myself smiling, as I reflected on everything that had occurred over the past 24 hours. For some reason, I found that I really enjoyed the smoothness of my legs as I rubbed them together.

Once I toweled myself dry, I began the apply the Neutrogena Body Oil all over my body. I found the scent of the oil to be quite refreshing and it seemed to bring a glow to my skin. With the oil on, I slipped back into my panties. I looked myself over in the mirror and adjusted my panties for a proper fit.

After watching some TV and catching up on the news, I decided to go to bed. I set my alarm to wake early and plugged in my phone to charge it. Once I got in bed, I clicked on the link Mistress had sent me. A very soothing voice began speaking, telling me to close my eyes and relax. Next I knew I was waking up to the sound of my alarm.

Laying in bed, I took in the feel of the satin sheets on my legs for several moments. Turning off the link, I made my way to the bathroom and promptly sat down to pee. Realizing that I had just automatically squatted to pee kind of made me laugh. Checking my phone, I saw that there was a text message from Mistress. She wanted me to only wear my panties, a pair of running shorts, sneakers, and a tank top, when I came over. She also told me to come directly into the house, strip down to my panties, put on my collar, and meet her in the living room.

A while later I was showered, freshly oiled, dressed, and heading out the door. My mind was racing as I drove to her house. What did she have planned for today? Would I be able to pleasure her again? Just as I was about to pull into her driveway, I saw the same car as yesterday, departing.

Once I was inside, I removed my cloths,folded them, and placed them neatly on the table. Next I put on my collar as instructed and made my way to the living room. I saw her siting on the sofa as I entered. "Good morning Mistress, how are you doing this Morning?"

As I approached her, she rose and walked toward me. "Oh my sweet Joey, I'm so happy to see you and right on time." She leaned in and gave me a quick kiss on my cheek. "You smell so nice this morning, I take it you like the Neutrogena Body Oil. I'm glad, you can wear that from now on when you come over." She seemed to have a somewhat wicked smile on her face.

Mistress stepped back and dropped her robe. All she had on were a pair of black stocking and high heels. "I'm especially horny this morning so why don't you get down on your knees and lick my pretty mistress pussy.

With that, she sat down and spread her legs wide open. I walked over to her and went down to my knees. As I was about to move in to eat her, she stopped me and told me "beg for permission to lick and eat my pretty mistress pussy and make it convincing."

Looking into her eyes, I began to beg her. "Please Mistress, may I have your permission to lick and eat you pretty mistress pussy? Please let me pleasure you and taste your pretty mistress pussy. I so wish to make you feel good, please allow me too."

"I believe you do my sweet Joey so, yes you have permission." She pressed my head toward her sex. I noticed the strong scent of her sex as I began to lick her. As I began to lick her, it seemed like she tasted a little different then my previous experience. It wasn't an unpleasant taste just different. Soon she was pressing herself to me. "Get your tongue deeper in me sissy, lick me out properly."

She had once again referred to me as a sissy, I again ignored it and continued pleasuring her with my mouth and tongue. While I was busy licking and eating her, I heard her open a drawer. Moments later, I felt something bump my nose. When I open my eyes I noticed that Mistress was rubbing herself with a dildo.

"Don't stop Joey, keep going, I'm just adding to the pleasure. I feel so naughty this morning and so need your help. Keep eating my pretty mistress pussy as I had some additional stimulation."

As I was pleasuring her I felt the dildo hitting my lips from time to time. Mistress was letting out some moans of enjoyment. "You like the taste of my pretty mistress pussy and juices. don't you Joey?"

"Oh Mistress, I very much enjoy the taste of your pretty mistress pussy and its juices."

"Good, I'm glad you do, now lick my juices off of this. Clean it up so I can get more on it for you. Be a good submissive for me, make me happy, and do it now." She point the dildo towards me, "please do it for me and make me happy."

Reluctantly, I leaned in and began to lick it the tip of it, Once she was satisfied that it was clean she directed me to proceed with pleasuring her. Mistress continued rubbing herself with the dildo, stopping just long enough to have me lick it clean every so often.

"I have a great idea Joey, why don't you put this in me. Slide it into me nice and slowly and make me feel good." She handed the dildo to me and said "do it for me and make me happy."

I was both nervous and excited at the idea of doing it. I so wanted to please her and make her feel good but, I didn't want to hurt her. Carefully, I started to rub the dildo along her pussy lips before gradually starting to slide it in. As it entered her I was amazed at how her lips open and then surround the object.

As i was sliding it into her she let out a moan of pleasure. "Yes Joey, slip it in deeper and slowly start fucking me with it. Make me feel good."

After about 5 minutes she had me stop and take it out of her. Taking it away from me she pointed it to me. "I don't want these juices to go to waste, clean this up so we can do more."

When I started to lick it, she began to laugh. "No no Joey, I mean really clean it." She then proceed to push my head toward it. "Take it in your mouth and really clean it off for me." Before I could get a word in, she had pushed it in my mouth.

"That's it wrap your lips around it and lick and suck it clean so I can get more for you. Let go of it and let me slowly feed it to you" While holding the back of my head, she slid a little more in. After a bit she began sliding in and out of my mouth. Moments later she removed it and pushed in into herself several times. "Clean it again Joey, suck my juices of of it!" She repeated this a number of times before handing it to me.

"Fuck me with it Joey, as you lick my pretty mistress pussy. I want you to make me explode in pleasure. Do it now bitch."

It took almost no time at all for her to let out a loud "Yes." Her legs closed around my head and I felt her body begin to twitch. Once she started coming down from her climax, Mistress had me once again remove the dildo and clean it with my mouth. When she was satisfied that it was clean she removed it from mu mouth.

"Stand up, remove your panties, and place them on the table. As i was doing it she walked away. When she returned she began walking around me and looking me over. "You look so cute being smooth all over, very sexy. Go bend over the arm of the sofa and spread your legs open so I can better inspect you Joey.

Once I was bent over she came up behind me. She began running her hands along my legs. Her hand began moving higher up my leg until it found my balls. She began softly fondling them. "Oh these are just so damn precious, so smooth and so tiny. You were clearly born to be a submissive beta male sissy."

Mistress then grabbed the cheeks of my ass and spread them open. Seconds later I felt a sharp slap on my ass. "Oh Joey, I thought you were told to shave smooth All Over" Another sharp smack on my ass. I simply can not allow this type of misbehavior. I'm hurt and you are getting a good spanking for this. Stand up and follow me to the sofa. Now bend over my knees, ass up high for your spanking."

I stood there looking at her, wondering if she was really serious about spanking me. "Joey, do you want to ever seem me again? If you do, you had better bend over my knees and accept your spanking. If not, leave and don't ever come back. You have 30 seconds to decide which it will be, either over my knees or out the door."

Moments later I slowly and shamefully bent over her knees, while telling her how sorry I was. No sooner was I in place the first smack landed, making me just. "Move that ass up high." Smack, smack, smack! "A submissive pays attention to detail." Smack. smack, smack! "They do this to please their superior." Smack, smack, smack! "Do you understand me Joey?"

Before I could answer. Smack, smack, smack! In a whimpering voice I managed to get out a Yes Mistress and I'm sorry Mistress,

Once she was done she had me stand up and put on a small pink lace thong pantie. She then handed me a matching pink bra, directing me to put it on.

"You want me to wear a bra Mistress?"

"Yes I do as well as other things in time. It is part of your sign of being my submissive. You will get use to them in time and learn to appreciate them. Now let me adjust it for you so you know how to wear it properly."

After my bra was adjusted Mistress had me take a seat on the sofa. When she return she had me put my right foot on the table and began to paint my toes pink. Once that was complete she did the same to the left toes.

When they were dry I was once again on my knees pleasuring her as well as cleaning the dildo. When I was done, Mistress told me i was becoming quite good at pleasuring her and learning to clean the dildo. "We will make this part of out routine from now on."

With my face sopping wet with pussy juice she sent me on my way, wearing my bra and panties along with the the panties from the previous day. I got dressed and left the collar at the door as said goodbye to Mistress. It was 2 PM as I drove off toward home. I was expected to be back at 11 the following morning!

Just like the day before, as soon as I got home I stripped down to look at myself in the mirror. The reflection was that of a soft male, clad in pink panties and bra wearing pink toenail polish. I just stared at myself while wondering, is this really me, am I a sissy. It almost seemed fitting given my stature. Slowly turning, I took in the sight of my bottom. The pink thong made my butt look very sexy, against the warm red from my spanking. Rubbing my hands on my cheeks, I felt the warmth of my glowing cheeks.

The ding of my phone broke my thoughts. It was a message from Mistress telling me to study the attached link and spend some time thinking about it. She added, a good submissive needs to fully accept their place.

I sent the link to my email and downloaded it to a jump drive to watch it on my TV. No sooner did it start and I realized Mistress had somehow recorded our whole session together. There I was begging her to allow me to lick and eat her pretty mistress pussy. Then the dildo play and me sucking it. It also showed me being spanked, as well as me being dressed in my panties and bra.


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2 Comments
missybaby57missybaby57about 3 years ago

As we discussed, I knew you had missed a spot. This is so sexy! Kisses sister.

cdCindy1cdCindy1over 4 years ago
Can't wait for the next chapter

This 2nd chapter really turned me on. I would love to lick a pretty mistress pussy and lick her juices off her dildo. Then I want to suck a real cock for her while wearing my sexy bra, panties and nylons. Let us know if the person in the mystery car is a well hung man who fucks mistress. I want to eat his cum out of her pretty pussy after he fucks her.

Please continue. I can't wait.

Hugs and kisses,

cdCindy1

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