Sissy Diary Pt. 03

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.

___________________________________________________________

Mary was relentless; she wanted me to fail and cum right there in the tub. I was trying my hardest to keep that from happening. I wanted to earn my surprise from Miss Angela. I tried to move my body forward, to release from her embrace, but she wrapped her free hand around the front of me and held me fast as she fingered my ass. At last, I couldn't stifle my moans, and one slipped out.

Miss Angela turned around after placing my cage on the sink counter. She walked over to the tub and smiled softly at me. "Sammy, are you having a hard time?"

"Yes, Miss," I replied, "Mary is..."

Miss Angela cut me off, "Mary is doing exactly what she should be doing and exactly what I asked her to do."

At this, Mary plunged her fingers deeper inside me, "See, Sissy, your Miss isn't going to help you here. She told me to push you, to tease you, and to bring you as close to the edge as I possibly can. Today is a test; if you can't resist me, then all you'll get is a quick little spurt. I'll ruin it and just let it dribble from those heavy balls of yours while I mock you. You have to manage to hold on long enough to earn that surprise to get anything good. Or is it that you can't? Are you so weak and needy that you can't hold your cummies in?"

"I would be so disappointed if that were the case," Miss Angela interjected. "After all the training we've done, I fully expect you to pass this test, sissy."

My heart throbbed in my chest, and I could feel my pulse racing. I needed to prove to Miss Angela that I was well trained enough for this, that I could handle this, and I couldn't disappoint her. I wanted to try and protest, to tell her that I could handle it, but in the heat of the moment, I was struggling to form basic words. Instead, all I could manage was a pathetic whimper.

Miss Angela turned around and grabbed the two towels hanging from the bar next to the tub and held them up. "I think that's enough teasing in the tub, though. We do have a busy day planned after all." At last, Mary pulled her fingers out of my ass, and I moaned again. I couldn't help it; the feeling of her going in and out of my hole felt so good. I knew my cock was leaking by now. I got out of the tub and began to wipe myself down. My cock was rock hard, and I couldn't help but blush a little as Mary and Miss Angela giggled, watching it bounce around as I cleaned myself.

After I finished wiping myself off, Mary stepped out of the tub and tossed her towel to me. "Come on, sissy, time to clean me off." I did as I was told and began wiping her down.

As I knelt to wipe her legs, Miss Angela gave me a firm spank across my ass. I moaned a little, at this point not even trying to hide how turned on and embarrassed I was. "That's for getting hard and almost cumming without permission, Sammy." I continued to wipe as I received another few spanks, making my ass begin to get a little pink. I admit I loved the feeling of being spanked. That blissful moment right after the sting felt magical.

I had learned early in my time with Miss Angela that it made things so much better if I just leaned into what I enjoyed. The shame and embarrassment of being on display like this only made it hotter. So as I leaned down to wipe Mary's other leg, I spread mine a bit and wiggled my ass a little, trying to be playful. Instead of a spank, this time Miss Angela reached around and gave my balls a solid smack, making me shudder. The other thing I had learned early on was that I definitely had a bit of a masochistic side that went beyond just spanking. Miss Angela continued to tease me like this, caressing me and then spanking me where she pleased as I finished drying off Mary.

After I finished drying off Mary, she walked to the door, "Come on now, sissy, it's time for you to put on what I picked out for you." With that, she strutted right out the door before I could respond.

I looked at Miss Angela, who smiled back at me, "I know this is tough for you, but you're doing a good job, Sammy." She took my cock cage and secured it in place. This actually made me feel safer, if I was locked up, it was far harder to get me to cum. This protected me at least partially from Mary's teasing. "I might take this off later to really challenge you, though, so be prepared for that." Miss Angela then began to walk out and down the hallway.

I whimpered as I began to walk to the door. "I promise I'm trying to be good, Miss. It's just so hard. I've never been teased like this before."

"Oh, I know, sweety, that's the point. In order for you to be ready for all the wonderful things I have planned for you, you're going to need to be able to make it through a simple test like this. After all, if you can't handle just me and Mary, what will you do when there's a full party of women teasing and humiliating you?" Miss Angela turned the corner into the bedroom before I could even wrap my head around what she'd just said. It was tough enough with just Mary added in, I don't know how I'd handle any other women added on. I couldn't help but wonder, was that a future goal, was that part of the surprise, what could Miss Angela be getting at?

When I entered the bedroom, I saw multiple things laid out on the bed. There was more than one set of lingerie and multiple dresses. Mary gave me another hungry grin as she licked her lips in anticipation. "So here's how this will go. You're going to help me get dressed first. Angie says you love helping with that. You're going to do it properly, though, every piece of me you're going to cover you has to kiss first." She pointed to the lingerie nearest to her. "So this is what you'll start with." There was a complete set, panties, bra, stockings, garter belt, all sitting together. It was a beautiful shade of dark blue that sparkled a little in the sunlight.

I reached first for the panties when Mary stopped me. "Sissy, that's not the order we'll be going with. The panties are going to go after the garter. I want to make sure I can easily slip these panties off when I want to have some fun. So start with the stockings." I did as I was told. I took one stocking at a time, and I began to kiss Mary. I started at the very point of her toes and slowly and gently worked my way up as I rolled the stocking up her legs. Her skin was so smooth and soft with just the lightest hint of a fragrance of flowers. It was intoxicating. Next, I took the garter belt and began to secure that in place. I kissed all around Mary's hips, feeling how tight and toned she was.

After that, I moved to the panties, as I began to slide them up her legs, I stopped just short so I could kiss every little bit of her skin they were going to cover, mind you, that wasn't much. Mary giggled as I kissed around her, planting multiple kisses on her ass. I admit, I enjoyed kissing her ass. It was so supple, but well sculpted. I gave a gentle kiss to the lips of Mary's pussy and took a whiff of her scent again.

I must have lingered a moment too long, as Mary noticed. "Oh, does someone want some more time with my pussy? Did you enjoy eating me out earlier? Don't worry, sissy, I'm sure I can give you some more time later today." I planted one last kiss on the lips as a reply. I couldn't help it; I did want more time with her.

Lastly, I began to secure Mary's bra. I planted kisses all around her chest before I began focusing on her breasts. I planted small kisses all around her nipples, and she seemed to enjoy this as she moaned a little. Then I heard another moan and turned my head to the side to see Miss Angela. She was watching us, but she had rolled up the skirt of her sundress and was actively playing with herself as she watched. This made me blush, and I felt so hot knowing she was getting off to what I was doing. This gave me a bit more excitement than I expected as I then began to lick at Mary's nipples, making her moan.

Mary's fingers intertwined with my hair, and she pulled my head back a little, backing me away from her breasts. I bit my lip as I felt her pull, unable to hide my joy. "Hey now, I only told you to kiss what you were dressing up, I didn't tell you to start making out with my tits." She smiled, "Though I do love your enthusiasm. Just finish getting this all on sissy. I want to keep going with our day." I did as I was told and clasped Mary's bra.

At that point, I stood in front of Mary, marveling at her beauty. She truly was gorgeous. The lingerie clung to her body and framed her so well, even though she wasn't as curvy as my Miss, she was still a knockout. "So what's next?" I asked.

Mary laughed, "Well, you are just so eager to please, aren't you? Now you're going to pick one of the dresses on the bed for me to wear." She pointed down, and I took a better look at the clothes on the bed. There were three different dresses, though each of them seemed to be for very different occasions. One was a light and twirly sundress, not very different from what my Miss was wearing, though it was a deep red color. The second dress was a floral pattern and seemed to be the sort of dress you would wear for formal tea. The final dress was the one that caught my eye, though. It was the little black dress. That slim, form-fitting black dress that I believe every woman owns for when she's on the hunt for a good time. It was black with just a hint of sparkle to it, with a small slit up one leg.

"The black one," I said eagerly. "I think you'd look so sexy in the black one."

"Oh really," Mary replied, "And why is that?"

"I think it'd show off your legs and your ass so nicely. Besides, such a nice dark color complements you well. You don't seem like much of a sundress person, and you certainly don't seem like the kind of woman who does formal tea time."

Mary laughed, "Fuck no. I would only do that if I were forced to for a business reason." She picked up the dress. "Good choice, sissy, this is the one I was hoping you'd pick." She tossed the dress over to me, "So put it on."

"But I thought I was picking your dress?" I asked, caught off guard. This was not the dress I would have picked for myself. I was far too shy for such a thing. It was a lot for me to have Mary see me in anything right now, let alone an attention grabber like the black dress. I was used to my Miss seeing me in all sorts of attire, but not knowing what the rest of the day held for me, I was hesitant.

"Put it on, Sammy," Miss Angela said from behind me, "You made your choice and now you have to follow through." She stood up and placed a reassuring hand on my shoulder, "You'll look wonderful in that dress. Don't worry, there's a matching set of black lingerie to go under it; it's strapless, so it'll complete the look." I can't believe I didn't see this part coming. There's no way a woman like Mary would have worn lingerie that didn't match her outfit, let alone a set with straps where there shouldn't have been.

Regardless of my embarrassment and hesitation, I did as I was told. I slipped on the black, silky lingerie and then slid into my new black dress. By the time I finished this, Miss Angela had brought out a black pair of heels for me. They were tall and had straps that went halfway up my calves, continuing to frame my legs. I put the heels on, and even I had to admit, I did feel sexy in this outfit. I felt like I was a hot girl going to a club, looking to grind on someone on the dance floor.

I was so focused on myself that I hadn't noticed Mary putting on her dress. By the time I looked up, she was wearing a form-fitting blue dress that was only a teensy less revealing than mine. She looked at me all dressed up and blushed a little. "God, Angie, she's so fucking cute like this." I could feel the pink on my cheeks as I got embarrassed again. "You mind if I make out with her a little while you get dressed?"

Miss Angela began to walk toward her closet, "Not at all, you two have fun while I change."

Mary basically threw herself on top of me and began kissing me passionately. I didn't hesitate to return the favor. I was so turned on. My cock strained against the cage, and I could feel my pulse race again. Even with all the teasing, maybe even especially because of the teasing, I was having such a fun day. I couldn't help but feel like I was the luckiest sissy ever. Mary pinned me down and kissed me, and it just felt so good.

I didn't even notice when Miss Angela came out of the closet in her dress. She sat down on the bed next to us, "Now, now you two, we have to get our makeup on."

Mary pulled back from me, rolled over, and sat up. "Oh fine, but I was having so much fun."

"Yes, well, so was Sammy, and now she has to dab off her panties before she makes a mark on her dress," Miss Angela replied.

I could feel the wet spot in my panties, so I knew Miss Angela was right. I got up and went into the bathroom, grabbing a cloth to dab myself dry first. Miss Angela and Mary followed me in and began doing their makeup at the mirror. After a moment, I also did, and I began to apply my lipstick. I admit, this was one of my favorite things. I loved the feeling of having my makeup on. It made me feel so pretty and girly, the lipstick especially.

Everything was going so smoothly until Mary asked Miss Angela a question, "So what time are we all supposed to be at the party?"

To be continued...