Sissy Diary Pt. 04

Disclaimer/Author's note: Everyone in this is 18+ and consenting, and this is completely fictional. Please send me any comments or feedback you have. I appreciate any encouragement you've got. I hope you're enjoying this.

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"Party?" I sheepishly questioned.

"Well, yes, sissy," Mary replied. "You didn't think we were getting all done up just to stay around the house, did you?" Mary was grinning and clearly enjoying the fact that she'd just dropped a bomb like that.

I suppose I should have figured something was off. Yes, Ms. Angela dressed well every day, and she liked to have me dress pretty, but the type of dress I was wearing with the heavier makeup was a bit much for just around the house. I just assumed it was Mary's preference in my naivety. My blood pumped faster as I began to contemplate what going to a party meant. I was shocked and afraid. Just meeting Mary was a big step for me; a party was a huge leap.

"Sammy, don't worry," Ms. Angela said calmly. "Mary and I will be going to the party; you don't have to go."

"Oh, come on, Angie, couldn't you have let me string her along a bit longer?" Mary said wickedly. "I think I could have gotten her so much more flustered. Maybe she was going to pout and cry, that would have been so fucking cute."

"No, Mary, that would have been cruel." Ms. Angela looked at Mary more sternly, "I may tease Sammy, but I would not be so cruel to her in that way. I treasure my Sammy. Yes, down the line I would love to take her to parties and show her off, but if she's not ready, she's not ready."

I calmed down a little as my Ms. defended me, but at the same time, I felt off I felt like I was already disappointing my Ms. by not being ready for an event like a party. That's when I gathered what courage and determination I had and spoke. "I want to go to the party," I said weakly.

Ms. Angela turned back to me and took a very serious look at me. "Sammy, are you sure? We just introduced you to Mary; this is a much bigger step. There are going to be plenty of other women there, and some of them will have brought their sissies too."

"Yes, Ms.," I replied, trying to sound more confident. "I want to do this. This is everything you've been training me for, right?"

"Well, yes, Sammy, it is," Miss Angela replied. "But I figured we were still several play dates with my friends off from a bigger social gathering like this. I wanted to build up your confidence."

"Well, I want to go," I said a little stubbornly. "I know you've trained me well. I want to meet the other women, I want you to be able to show me off."

"Sammy, you realize if you go to this party, the cat is out of the bag, right?" Ms. paused to let that sink in. "That will be a large group of people who all know you as Sammy, my girl, and from then on, you'll be going out and about with me." She put a hand gently on my shoulder. "There's no going back from that; it's opening a door that can't be closed."

"It's what I want. I am Sammy, I always was, I just didn't know it until I met you." I smiled at Ms. Angela. She had done so much for me, I didn't want to be hidden away at her house anymore. "It's time."

Cutting through the serious mood like a knife through hot butter, Mary interjected, "Fuck yes it is! She can do this, Angie. She's been a good girl this whole day with me around, and you know I've been testing her. She can handle the party; besides, it's not a particularly big one. There's only going to be like twenty people there, including the other sissies."

"I suppose you're right, Mary," Ms. Angela said. "If I'm going to bring Sammy out, this is about as good a chance as ever." She paused for a moment and thought, piecing together how that changed the day. "There are a few rules, though, Sammy."

"Of course, Ms. Angela, I'll do whatever you say," I replied excitedly.

"First, you are to tell me if you're uncomfortable. If that happens, we will come home and try again when you're ready, agreed?" I nodded my head. "The second is that you are to stay with me unless I specifically hand you off to someone."

"Of course, Ms..," I replied. "I plan to stay by your side."

"Sammy, at these parties, it can be easy to get separated. Some of the other women can be a little extra handsy, especially around new girls like you."

"I'll stay with you, Ms," I said again. "Or at the very least Mary."

Mary giggled, "I'm not sure how safe you'd be with me, girly. I might just decide to take you off to another room, and rip that dress off of you."

Ms. Angela turned back to Mary and gave her a disapproving look, "Not without permission from both of us, you won't."

"Of course not, Angie," Mary said. "I would never do anything the two of you didn't want me to do. I'm just saying, the second you both agree, I'll be mounting Sammy on the spot."

You are incorrigible, Mary," Ms. Angela replied. "Now, Sammy, you also need to pack a purse for this. You'll need to be able to touch up your makeup easily and quickly. As much as I'm saying, you'll stay with me, there will still be plenty of times that the other woman will want to see you, inspect you, and test you."

"Inspect me and test me?" I question.

"Yes, Sammy," my Ms. replies. "They will want to touch you all over, and kiss you, as much as it's about you, they'll also be interested to see how much I have transformed you and how you're developing."

This made me blush, as much as I was afraid, the idea of a bunch of women touching and evaluating me like that was admittedly hot.

"Which means they'll be looking to see how much of a mess you'll be making, sissy," Mary interrupted. They'll love to see that Angie has you caged, and they'll enjoy it even more when you start to make a leaky mess in your panties. Though if I were you, I would bring a second pair to change into later on. I have a feeling you'll be making a complete mess of yourself." Mary went back to putting on her makeup as Ms. Angela finished telling me the rules.

"Again, you do not have to do anything you don't consent to, and I do mean that." My Ms.'s tone dropped, "If any woman there tries to make you do something you're not comfortable with, they will have to answer to me."

"And me," Mary replied, "No way they are getting to take you out for a test drive before I do." She finished a coating of lipstick as a last touch before looking back at me. "None of the other ladies are going to get to smear your lipstick on their strap-on before me."

I immediately turned bright pink as my cheeks flushed. I was embarrassed and turned on. I admit, I loved it when Ms. took me with hers. I could only imagine how enthusiastic Mary was. I had honestly been trying not to think of that all day.

Mary clearly saw the effect her words had on me, "God, you're so cute, sissy, you really want that, don't you? Maybe that's your big reward: you make it through the party, and we get to come back home so I can fuck you properly. Don't worry, I picked out my favorite toy for you. Even with how Angie has trained you, I'm sure I can make you gag and squirt with it."

I couldn't even look Mary in the eye at this point. I was so turned on. Thankfully, the cage was keeping me under control. However, I didn't want to make a mess of my dress before we even got to the party, so I grabbed a tissue and dabbed off my now leaky cage.

"That's enough now, Mary," my Ms. interjected. "If you make her a mess here, she won't even be able to make it to the party."

"Yeah, I suppose," Mary pouted. "But you knew what you were getting into when you invited me to meet her. When I want something, I can't help but aggressively go after it. Besides, I like being a little worked up before a party. Get the pheromones going a little and walk in already on an endorphin high." Mary stood up, her makeup done. "Though you might need to help her get ready, Angie, I think we distracted her so much that she's barely got any makeup on." She walked out of the room, and I could hear the clicking of her heels down the hallway.

Ms. Angela turned back to me, "Are you really sure about this? I don't want you to do this just because you're being teased by Mary. I know she can be a bit much."

"Yes, Ms., I am sure," I replied. "If anything, I think Mary might have just been the push I needed to put myself out in the open for you. I want to be able to be at all the social gatherings you go to. I want everyone to know I'm yours."

"Alright, Sammy, then let's finish up your makeup so we can get going. I suppose this means we'll be fashionably late whether I intended it or not."

Ms. Angela helped me finish my makeup, and then we picked the things to go into my purse. It was a small black purse that went well with my outfit, and I could manage to simply sling it over one shoulder. After that, we proceeded to get into the car and drive to the party. The whole ride, Mary and Ms. Angela talked about different people and things going on. I didn't say much unless they asked me a question, but I tried to take note of names so that I might be able to put them to faces once we were there. We were only going a town or two away, so it wasn't a particularly long drive.

I looked up the driveway as we reached our destination. We were pulling up to a rather large house, one of those mini-mansions that were honestly a little bland in style, but they were really only about showing financial status.

"So, Ms., is this the house of a friend of yours?" I asked.

"Sort of, I would call her an acquaintance more than a friend. We both run in the same circles, we both run our own companies, and well, we love spending time with other women and sissy girls like you. So not exactly the largest of communities. Really, it makes a small group of us who meet from time to time. Today is just a small gathering because one of our ladies has just closed on a big deal for her business, so she wanted to celebrate. Her name is Jane."

"Oh, ok, and you said there would be like twenty people here?" I was trying to calm my nerves. The smaller the number seemed, the easier this would be for me."

"As far as I know, granted, sometimes there are additional guests that show up, and I don't really have a count on how many women will be bringing girls like you, Sammy." Ms. Angela paused for a second and then continued with a realization. "Well, I suppose this will be another first for you. It'll be the first time you're likely to meet some other sissy girls."

"You're right, I hadn't thought about that part much," I replied. "Is there anything I should know about that?"

"No, not really. The sissy girls tend to be pretty eager to please. Some of them say yes to anything and everything going on, which I see as a bit much. Honestly, there is a lot of personal styling. I can tell the taste of the woman who trained the sissy by looking at her."

This, of course, led me to thinking about how I would show what Ms. Angela likes. "So that means I show off what you like?"

"In a way, though, really Sammy, what I like is you." My Ms. turned back and smiled at me, "Besides, I plan on changing your look fairly regularly. After today, if today is a success, I can take you out whenever I want, which means a lot more trips to the salon for new hairstyles, and we can go clothes shopping regularly." She began to open her car door as she finished up. "It's time to go in now, Sammy. I hope you're ready."

"I am ready," I said, though honestly I feel like I was saying it more to myself than I was to my Ms. We walked the short path from the driveway to the house entrance.

Mary walked beside me and began speaking in a whisper. "Honestly, sissy, that probably wasn't the whole truth. You see a lot of the women here are pretty competitive with one another. If anything, Jane is a rival of Angie's. She just didn't want to put any pressure on you."

"Then why did you tell me that?" I say without hesitating. It had already become abundantly clear that Mary liked to stir the pot, which worried me.

"Because this is a chance for you to really show up for Angie. You coming here without prior announcement is actually a bit of a power move. Normally, the ladies here say when they are bringing a new girl, and that's a big part of the event. Angie just didn't want to take the wind out of your sail once you said you wanted to come." Mary stopped just before the stairs leading into the entrance and turned so she could look me in the eyes. "So I would take every bit of courage and confidence I have and put it on display. You really love your Ms., now's the time to show it off." She turned back around and followed Ms. Angela. I took a deep breath, collected myself, and did the same.

We stepped into the entranceway, and it opened into a large room with a curving staircase on either side. There were some women standing and chit-chatting, though it was clear the actual party was one room further back, which appeared to be the hosting space. Ms. Angela and Mary greeted a few women as we walked by, and I waved and tried to give a cute and shy look. As we walked to the hosting space, I could hear some of the women murmuring behind us, though I couldn't quite make it out.

Once in the main room, we could see most of the other guests. There were women in all sorts of dresses, all seeming to be their personal choices for style and color. I admit, I sort of liked it this way. There was no singular theme that dictated everything; each woman put their personality on display. It was easy to pick out the assertive and dominant woman due to the all black looks, whereas some of the women wore lighter sundresses. In the middle of the room was a large table with all sorts of food across it and plenty of drinks. At the far end of it was a woman standing in the center of a group holding court. It looked like each other woman was hanging off her every word, which led me to understand that this must be Jane. She was a shorter woman, likely no more than five foot three, but she was taller than that now due to the height of her heels, adding several inches. She had gorgeous dark skin and a confident glow about her. Her dress was red and rather low cut to show off her ample cleavage. Her midnight hair draped over her shoulders in large curls that almost shined in the light.

We walked over toward the group, and Jane made sure to notice Ms. Angela, stopping her conversation to greet Mary and my Ms.

"Angela and Mary, so nice of the two of you to come by to celebrate with me. You two look absolutely stunning as always." They exchanged little kisses on the cheek before Jane turned her attention to me. "Now, who exactly is this little treat? Angela, don't tell me this is the Sammy we've all heard so much about? I didn't know she'd be making her debut today."

My Ms. smiled, "Jane, let me formally introduce you to Sammy. Sammy, this is Jane."

Jane held out her hand toward me, and I knew what to do. I leaned forward and planted a small, soft kiss on her soft skin.

"Such a sweetie, and it looks like you have her so well trained, Angela. This is such a splendid treat for us all today." Jane smirked, and I felt a little bit afraid. She raised her voice a little to gain the attention of the women in the room. "Oh, ladies, we have been brought an extra special surprise from Angela today. She brought her new sissy, Sammy. I think it's such a special gift that we should all have a little time inspecting her, don't you all agree?" The women all circled me after that, and for the first time, I truly felt on display. They looked me over from head to toe. I gave them a little bit of a show. I posed and I twirled in my dress. I tried to show every little curve and feminine feature I had.

"Do you mind if I inspect her, Angela?" Jane asked.

"As long as she is ok with it?" my Ms. responded.

Not wanting to disappoint her, "Please do, Ms. Jane," I replied sweetly. "I'm sure I'll be to your liking."

"Well now, she is a confident little thing," Jane said with a smile. She stepped closer to me and began to run her hands along me. I felt her fingernails trace my skin in the most delightful way. I wanted to try and put on a show for everyone there, so I let out a little moan as she reached my nipples and another when she caressed the curve of my hips. After the second moan, Jane leaned in and kissed me, pressing her body right up against mine. My pulse jumped, and I know I let out an excited little squeal. That's when I felt Jane's hand slip under the edge of my dress and touch my cage. She pulled back from the kiss with a rather satisfied look on her face.

"She's caged, she makes the most delightful sounds, and she's quite the good kisser. Angela, I'd say you've done an exceptional job with Sammy here," Jane said as she began to take a step back.

Ms. Angela smiled at me, beaming with pride. "She is such a good girl, that's what I brought her today, I just couldn't keep her to myself anymore."

"Well then, if you can't keep her to yourself, then I suppose everyone else needs to take a little sample, then don't they?" Jane grinned wickedly. "I think that will be the game for the day then. Ladies, each one of you needs to sample Angela's Sammy and tell Angela what you think. I'm sure by the end of the party she'll have been inspected from head to toe and Angela will have some new things to teach her."

To be continued...