The Awakening of a Sissy Pt. 05

There I was, on my knees, in very skimpy feminine undergarments, locked in a room in the back of an ABS, with 6 men and my Mistress. This was the start of what was to be the other portion of my punishment. Mistress walked toward me with that evil grin of hers.

As she was approaching me, she said, "Jolie, these men are here to assist me with your punishment. I expect you to do as you are told, without question. In the end, this will help you better identify with your true inner sissy. It will also help you better understand your place."

"Now stand up and strip, get out of your bra and panties, I don't want them messed up" Mistress told me. As I stood. the blood rushed to my face from knowing what I was about to do. My hands were shaking as I fumbled with my bra clasps. Once it was off, Mistress took it from me.

"Now your panties Sissy Jolie, get them off also. "Let the men get a good look at that pathetic little clitty of yours. Let them see how feminine and smooth you look." I felt so embarrassed and humiliated as I slipped my panties off. The men began laughing and pointing at me, seeing I was locked in chastity, as I stood there naked. A few of them made comments about my sissy tan lines.

As i stood there, I saw some of the men rubbing their crotch, while they talked to each other. My mind raced, was I going to have to suck off each of them? Would they all be cumming in my mouth? Suddenly I realized I was no longer taking the position of, I would not do that. I was now accepting that I would, and may have wanted it.

Mistress told me to slowly turn around to let them see all of my sweet sissy goods. With my back turned toward them, Mistress told me to wiggle my sissy ass for the men.

"Look at this firm bubble butt ass, doesn't it look so fuckable," Mistress stated as she giggled my ass. "Isn't the the most fuckable ass you have ever seen?" The humiliation as well as the excitement was building in me. She wasn't going to have them fuck me would she?

After a few moments, Mistress had me turn back around so I was facing the men once again. As I stood there facing the men, Mistress told them to pull their cocks out of their pants so I could see them. She gave me a few moments to take in the sight of their cocks.

"Jolie, you need to be a good sissy and introduce yourself to each of these fine men that I have picked out just for you. I want you to walk up to each one of them and say, Hello Sir, I am so happy to meet you and your wonderful cock. I look forward to getting to know it better today,"

I did as I was told and introduced myself to each of the men. As i spoke to each of the men, my eyes were fixated on their cocks. Each one looked so manly and powerful. I found myself wondering what it might feel like in my mouth.

Soon after, Mistress told me to climb on the love seat, telling me to face the wall. "Lean down, push you ass high up in the air, press your face to the wall and do not look back" she told me. I was both embarrassed and excited, what did she now have in mind for me?

Reach back and spread your cheeks Jolie. Let the me get a good look at your sissy pussy and the trainer you have inserted in you. I have a special treat for you and your pussy, a new trainer. I am certain you will love it. This one is a little longer and a little thicker."

First she removed my old trainer. Again, I felt that emptiness once it was removed. She was soon working the new trainer into my pussy. I could tell and feel that this one was larger. I felt it stretching me more and also entering deeper into my pussy.

I let out a soft Ohhh as it was finally slipped in place. While it was somewhat larger, it removed the empty feeling I had felt. Without a thought, I thanked Mistress for my new trainer. Little did I know it came with a surprise.

For several moments there was almost silence in the room, accept some occasional whispering, that I was unable to make out. Next thing I knew, there were hands touching me all over. There were hands on my legs, bottom, waist, and breasts. The men were feeling me all over. As they moved around, I felt what seemed like their cocks rubbing against me. It became apparent that they were now all naked.

"Keep looking at the wall sissy," Mistress stated. I felt hands spreading my cheeks open. Soon after, A hand was working my new pussy plug in and out of my pussy. The men were laughing at me. The plug fucking brought out soft moans and whimpering of pleasure from me. This made the men laugh more.

There were comments like, what a hot little sissy, how femme. What a nice ass, I'd love to fuck the bitch, she is so damn hot... There were also comments about the smoothness of my skin and the shapeliness of my legs. While I could not see them, I could tell the men were still rubbing their cocks on me.

Suddenly, without warning, my trainer began to Buzz. The vibration, kind of made me jump. Next came a thumping feeling. That was followed by a swelling feeling that grew and then shrank. It made my pussy tingle. Mistress laughed out loud..

The old Joe would have retreated and left in a heartbeat. Jolie however was seemingly enjoying her new role as a sissy submissive. My mind was racing with pleasure, lust, excitement, and wonder. The men touching me clearly was getting me excited. I kept wondering if I was going to be made to suck them and what it would be like.

It dawned on me that I was suddenly willing to do it. What was happening to me, was I somehow changing? My body was quivering in excitement from their touch.

After what may have been 15 - 20 minutes, Mistress told the men to go line up.

Once again, things seemed to go very quiet. I could hear movement and some whispering in the room. My mind raced with thought of what might be next for me and the men. Mistress broke the silence saying, "close your eyes Jolie, keep them shut and stand up and follow me."

I carefully stood, eyes closed, as Mistress led me to another spot. When she had me in position she told me to open my eyes. As I did, I was surprised to see all the men lined up. They were completely naked. Their cocks were in various states of semi stiffness. I realized they were lined up according to their size. The smaller cocks, which were not small, were to the left. The larger to the right.

I could not take my eyes off of their cooks, they all looked so wonderful, perhaps even beautiful. I found myself studying their length and thickness. Why, I do not know, but I began licking my lips. They were all well gifted and each had large ball sacks. My heart was pounding with a mix of excitement and nervousness.

"Do you like the cocks I picked out for you Jolie," Mistress asked. Without a moment of thought I responded saying, "oh yes Mistress, thank you, they are all wonderful." While I was shocked at the words that came out of my mouth, I knew deep down, I meant them. It was becoming clear that Jolie was the more powerful force and Joe was being pushed further and further away.

Mistress called the first man to the left over. She told him to turn around with his back to me. She then had me walk directly behind him. She guided me into position, I was pressed against his back side, skin to skin. Mistress then had me wrap my arm around him and told me, "Jolie, take his cock in your hand and jerk him off."

This was it, the moment of truth, I was about to touch another mans cock for the very first time. Jolie kicked into high gear and I found myself reaching to him. When I made contact, I was amazed to feel the heat of it, it's smoothness, as well as it's weight. I ran my fingers all over it before taking it into me hand.

Once he was in my hand, I very slowly began stroking him. I could tell he was enjoying as he grew in my hand. There was a sense of pride, I was actually making him hard. When he was fully hard he began moaning in pleasure.

"That's it baby jerk my cock, make me cum for you. I was amazed at how hard he was getting and yet there was a softness to his erection.

Mistress was once again making my pussy trainer vibrate and pulse. My pussy tingled from these new sensations. I let out a sensual Ohhh and clenched my cheeks, squeezing my pussy on the trainer

As I pumped him, he leaned his head back on my shoulder. "You're going to make one fine bitch for some lucky man," he stated. Suddenly there was another strange vibration in my pussy. I let out a soft wow and saw Mistress smiling while playing with her phone. My new trainer was clearly remote controlled and Mistress was controlling the sensations I get.

My hand never stopped stroking his cock. He was moaning in pleasure and encouraging me to pump him faster. A while later he stated out loud, "I'm getting close, go faster."

A few pumps later, he grew and twitched. I felt his cock pulse as he shot his ropes of cum to the floor. As he did, the other men began to clap. I felt proud of what I had accomplished and began to blush.

No sooner was I done Mistress had the next man step forward. This time she had him stand in front of me. Before long, I was jerking him off. I watched as his cock grew in my hand. I observed the pleasure on his face as I was stoking him. My eyes were fixed on his cock, it looked beautiful. Mistress continued having fun with my trainer as I pumped away on his cock. Once again, just before he came, I felt him grow and twitch, before his prize was released. Two down, four to go.

To my surprise, Mistress asked the next two men to come forward. "On your knees Jolie. You know that is where a sissy belongs when cock is involved." She had the 2 men position themselves on each side of me.

"Okay Jolie, now jerk both of them at the same time. Sissy sluts are never happy with just one cock."

I don't know if I was just caught up in the moment, I loved having a cock in each hand. These guys were different then the previous 2 men. They seemed to enjoy humiliating me and calling me names. I was called a faggot, a cock slut, a sissy bitch, a whore... I don't know why but the humiliation seemed to be turning me on and stimulating me even more.

The feel of 2 cocks in my hands was wonderful. I thought to myself, if this is punishment, I could be punished all day! I smiled as they each shot their loads on the floor. Four down, 2 to go.

Mistress called the last 2 men over. She directed them to stand directly in front of me. She had them move in closer, their cocks were mere inches from my face. Mistress looked at them and said, "remember your instructions, the face, not in her hair."

As soon as she said it, I looked at Mistress as if questioning what she had just said. Mistress looked at me and smiled. While laughing she said, "Yes Jolie, your face, you are about to get your first cum facial. These 2 wonderful cocks are going to make sure it is an experience you will never forget. Now get to work and jerk them off like a good little sissy bitch. I know you can't wait for your reward."

While I began stroking them, I thought about what Mistress expected. She wanted them to cum all over my face. Just thinking about it made me feel so humiliated but still I was excited. Yet there I was, excepting my role. I was willingly jerking their cocks for them, so they could cum on my face. I felt ashamed, slutty, and aroused.

A part of me was curious about how it would feel as they splattered my face with their cum. I found myself wishing that Mistress would have made me suck them. She continues teasing my pussy with my new trainer.

I had a good eyeful of the 2 cocks as I was stroking him. They quickly grew hard in my hands. Both were bigger and fatter then the previous cocks. I estimated that both were about 8" and fairly thick.

I had been stroking them for about 10 minutes, when the first guy announced that he was getting ready to cum. Soon, splat after splat of warm cum was hitting my face. Moments later the second cock erupted splashing my face with an even larger load of warm cum then the first.

Mistress told them to use their cocks to smear the cum all over my face. As they did it, she told them to make sure that my lips were also well coated.

Mistress laughed, as they rubbed their cum covered cocks on my lips.

While they rubbed their wonderful cocks on my lips, unconsciously, I ever so slightly opened my lips for them. Allowing them to better cover my lips. I half hoped one of them might push it into my mouth.

"Oh Jolie, you look like a perfect little sissy cock slut with your face covered with cum and on your knees," Mistress exclaimed. "You must now properly thank each of the men for sharing their cocks with you." She leaned down and whispered in my ears my new instructions. I became quite excited upon hearing my instructions.

One by one she led each of the men to me, so I could properly thank them. As they stood in front of me, I reached my hand out and held their now flaccid cock. "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." I then leaned in and gave the head of his cock a nice warm kiss.

Once they were all properly thanked and dressed Mistress led them out the door. "Okay Jolie, put your bra and panties on, I need to show you off to the other men."

As I dressed, I thought to myself, the facial wasn't humiliation enough. Now she wants to show off my cum covered face to all the other men hanging around by the booths. While putting on my bra, I reflected on how nice it felt to kiss each of those cocks. I so enjoyed the feel of their smooth velvet cock heads on my lips.

Mistress handed my my purse telling me to fix my lipstick. Before applying my cock sucker red lipstick, I licked my lips clean, tasting a slight hint of cum. With that done, Mistress slowly paraded me all around me back booth area.

As I was walked around, I could hear men making comments about me and my face. One guy rubbed his crotch while telling me "hey sissy, you can wrap those lips around my cock anytime you want." Little did he know how I would love to. Before exiting the booth area, she had me put my coat back on.

On the drive back to my house we discussed what had happened in the ABS. Mistress picked my brain for every thought and emotion I had experienced. She wanted to know what I thought about seeing their cock, touching them, and making them cum as well as kissing them.

During the discussion, I admitted to her, that I was surprised, that she had not made me suck at lease some of them. She looked over at me and smiled. "Are you disappointed at not having to suck cock Jolie?"

I struggled with how to answer her. "I don't know if I was disappointed Mistress, well maybe a little, yes I was kind of disappointed. I think I was prepared to do it, perhaps wanting to experience what it would be like. Is that wrong of me?

"Oh Jolie there is nothing wrong with that, I'm glad you shared that with me. You are making such wonderful progress. Far better then I ever would have imagined. Tell me all abut what thoughts go through that sissy little head of your when you think about sucking cock."

Jolie was in total control of my mind, at least for the moment. First i told her about how I wondered if I could actually do it. I told her how I wondered what it might be like to have a nice cock in my mouth. I wondered how it might taste. Would I enjoy it? I shared with her my curiosity of what it would be like to have a man cum in my mouth. Would I like the taste, would I be able to swallow it? I was totally blushing as I spoke.

Mistress told me how proud she was of me for sharing my thoughts with her. "It sounds like Jolie is really starting to accept what she is meant for. Those effeminate feeling will continue to grow within you. I may have to get you to meet my Doctor friend much sooner than I had imagined. She will get you on the right combinations of hormones."

"They would be a mix of female hormones and testosterone blockers. The testosterone blocker will wipe away that bad maleness stuff that builds in you. "The female hormones will greatly improve your femininity. They will make you so much smoother and way more effeminate."

"In time, you will look so adorable with budding little breasts. Your little clitty will shrink even smaller, along with those 2 tiny jewels you have down there. What do you think about that Jolie, sound interesting to you?"

"I'm not sure what to say Mistress. I had never thought about it before. My clitty shrinking would not be a big deal as well as my jewels. It's not like a woman would find it satisfying the way it is. I don't have anything close to what those men had today. I know I never will. It might be nice to have some breasts to actually fill in my bras. I guess it is something I have to think about."

Mistress' phone rang. "Hi Nikki, how have you been dear? I guess you got my message. I have a new client for you. Her name is sissy Jolie and her home needs to be remodeled to properly reflect her new effeminate persona. Yes, totally redone. From the work you have done in the past, I know you would be perfect for the job. I'll send you her phone number and address. Let's start with the bedroom, bathroom and living room. Yes, I'll let her know you will be over later today. Thanks so much, love ya!"

"That was Nikki, the home remodeler that I had told you about. She will be contacting you later today. Sounds like she will be over your way in a few hours. Let her look your place over and get some measurements. Don't worry about her seeing you in your feminine attire, she has seen it all before. You will need to give her a key to your place so she can work even if you are not around. I know you will adore what she does to your place. It will so reflect the new you."

Before long we were pulling into Mistress' driveway. She led me directly to her home gym. Soon I was back in my skimpy bikini, my face wiped clean of my cum facial and on the tanning bed. With my ear pieces in, the soft voice once again started. I woke up to Mistress shaking me and telling me that was enough tanning for the day.

She helped me off the bed and led me to a table where my bra, panties, shorts and blouse were waiting, along with my sandals. Get dressed and then I'll take you home. We were on our way moments later.

When she dropped me off, she told me she wanted me over at 9:30 the next morning. I was reminded that Nikki would be contacting me. She told me to continue practicing walking in my heels while concentrating on my posture. I was reminded to also watch my cock sucking video as well as practicing my sucking. Mistress said that there should be a package waiting for me at the door. "Enjoy your bubble bath, think about the hormones while you are soaking" she said as she pulled away.

Sure enough, as I approached my front door, there was a package waiting for me. As I was bending down, my trainer went off. My pussy was feeling a mix of vibrations, thumps, swelling and then shrinking. I clenched my pussy as the stimulation continued. I laughed thinking, Mistress has a new way of saying goodbye.

Once my trainer had stopped, I took the package inside and directly to my bedroom. Inside the box were a number of items. There were 2 robes, both pink. One was a lovely short satin robe, perhaps maybe mid thigh. The second was a very sheer, almost see-thru, full length robe. Next, was a pair of pink furry bedroom slippers, with a 1" heel. I then found a pair of pink heels, the heel was 4" in height. Inside the box there was also 4 nighties. Each a different shade of pink and very skimpy.

I quickly stripped out of my clothes, wanting to try them on. First I had to look at myself in the mirror. My sissy tan lines were even more pronounced. I found that I loved how effeminate they made me look. I smiled knowing they screamed sissy. The piercings. my hair, and eyebrows nicely added to my feminine look.