[Fiction] A Sissy’s Outing

[TransAubrey]

I hope you all enjoy the first part of a new story I’m writing and would appreciate any feedback you’d like to leave!

Part 1

I woke suddenly to my blaring alarm. I grabbed my phone and silenced it, but as I did a saw a message from my Mistress that read, “I hope you’re ready for today, Sissy! I’ve got a special surprise planned for you that I just know you’re going to LOVE!! I’ll be over to your house around 10 and I expect you to be fully shaven and to answer the door for me naked and on your knees.” Reading that message instantly woke me up and had my sissy clitty straining against its ultra-tight confinement in a chastity cage.

I had about two hours to get ready so I took my time getting up and showering, making sure to remove every last hair on my body from my forehead down; yes, including my eyebrows. Most of the time when Mistress comes over, she likes me to already be dressed a certain way with my makeup and hair done, but my favorite times are when she does that herself because then I know I’m in for a very special treat! I finished up shaving everywhere with about half an hour to spare so I grabbed a quick breakfast before kneeling down in before my front door in anticipation.

The doorbell went off right at 10. I opened the door from my knees and got a good look at my Mistress’s outfit for the day. She was wearing rather demure clothes for a play session: low black heels, black pantyhose, a knee length sundress, large sunglasses, subtle makeup, and her long blonde hair was pulled in to a casual ponytail. The outfit definitely accentuated her assets but didn’t overplay them or expose them in her usual style. She walked in right past me saying, “Good job, Sissy. Now be a good girl and go get the things out of the backseat of my car.”

“Umm, yes, Mistress…but without any clothes on? It’s broad daylight,” I asked sheepishly.

“Yes, and remember what I’ve said about questioning me.”

“Of course, Mistress. I’m sorry,” I reply while getting up and peeking outside to see if anyone is looking. Hurrying out to the car, I saw a car pass by and honk their horn at me. I blushed pretty hard and that only made me hurry even more. In the back of Mistress’s car I found a large dry cleaning bag as well as a couple of duffel bags. Getting them all inside in one trip was a bit of a challenge but one I managed to accomplish.

“Good, Sissy. And don’t worry, that’ll be the least humiliating thing you’re going to experience today.” Without giving me a moment to process that, she continued, “Now go ahead and take all of that up to our room. Hang the dry cleaning bag nicely and put the duffel bags on the bed. And no peeking!” She instructs with a firm slap to my naked backside.

I get a slight jolt from the spank. “Thank you, Mistress. And yes, Mistress, right away!” Hurrying the clothes upstairs I can hear Mistress slowly and casually following me. I hang up the garment bag and set the duffel bags on the bed before heading over to sit in the chair in front of the makeup table.

Mistress walks in just as I’m sitting down and says, “Good job, Sissy. Now we’re going to have some real fun today! First, I’m going to get you all dressed up, but I don’t want you getting any peeks at what you’ll be wearing until I’m ready for you to see, okay?” She walks over to one of the bags and pulls out a blindfold that she quickly slides over my eyes, ensuring I can’t see a thing. “Now I will need you to be helpful when I put some of these things on, but at no point will that blindfold come off, understand!?”

“Yes, Mistress.” I can hear Mistress walking around, opening up the bags and pulling various things out as I wait patiently in the middle of the room, hands at my sides. Following all of Mistress’s instructions, I can feel a plug being inserted, and, based on the feeling of things now dangling and hitting my legs, I can only assume it’s my favorite vibrating and inflatable butt plug, though Mistress hasn’t inflated it at all yet. Next come the panties being slid up to help hold everything in place, followed by what feels like another pair of panties, though I’m not sure why. Next comes some tight rubber being worked over my arms and head and neck, eventually settling on my chest. Based on the weight, I’m sure it’s my G sized silicone breast plate. After this, Mistress helps me sit down on the bed. I feel like the bed is more padded than usual but can’t quite put my finger on why, meanwhile I can feel Mistress rolling stockings up my silky smooth legs.

Mistress quickly helps me back up off the bed before having me hold what I quickly find out is a corset while she stiches it incredibly tight behind me and attaches the built-in garter straps to the stockings. Next, I can feel a dress being put on and zipped up in the back, but I can’t feel any material on my legs, clueing me in to the fact that this is a very short dress. After the dress is on, Mistress adds a posture collar that prevents me head from moving in any direction to the mix before helping me into heels that feel a mile high. “Alright, Sissy, you look fantastic now! Well, other than your lack of makeup and a wig, but I can fix that,” she says while taking off my blindfold.

I quickly blink, readjusting my eyes to the light after being blindfolded. As I try to look around, I quickly realize I have to move my whole body to do so, and I also can’t look down at all to see what I’m wearing, other than a slight bit of pink ruffles that are encasing my extremely large fake breasts. “Now I’m going to help you walk over here to the makeup table and sit you down so I can get to work on this face of your’s.” Guiding me by the hand and with a few stumbles in my incredibly high heels, I make it over to the makeup table and see that the mirror is covered, preventing my from seeing myself at all.

“That’s right, Sissy, I don’t want to spoil the surprise yet!” Mistress exclaims as she begins pulling out makeup. “First things first, let’s get this hair of your’s into the bald cap so we can do the wig here soon.” With expert care and attention, my hair is quickly pulled into the bald cap and everything is pinned tightly in place as Mistress comes back around in front of me to start on my makeup.

“Isn’t this so much fun, Sissy!? Oh I just love getting you all dolled up! First we’re gonna start with your foundation, and don’t worry, I’m not gonna light on anything today!” Mistress takes her time thoroughly covering my face in foundation before moving on to drawing on my eyebrows. When she finishes my brows, she moves on to my eyes, liberally applying what I assume to be many different colors of eyeshadow, blending it all the way out to my overdrawn eyebrows. She follows that up with what feels like very thick eyeliner, and soon after that I can feel her gluing eyelashes on. They must be very large eyelashes as I can see them when I open my eyes and can also feel the slightly increased weight. Next up is my lips, which also feel like they’re being very overdrawn. Mistress finishes my face up with some highlighting and contouring before telling me, “oh my, you are so beautiful my dear! Now for the finishing touch, your wig! Now close your eyes for me and no peeking!”

I shut my eyes and can feel Mistress putting on my wig and adjusting everything to where it should be, pinning it where it needs pinned, glueing down the lace front, and adding more foundation and contour to the lace to blend it in with my forehead. I can feel the weight of the wig on top or my head and I can feel a whole lot of hair cascading down over my apparently exposed shoulders. Mistress stands me up and I can hear her dragging something out onto the floor. “Alright, Sissy, time to open your eyes and take yourself in!”

I open my eyes and am astonished by what I see staring back at me in the mirror. I see someone who looks nothing like me. She, or rather me, is wearing bright hot pink platform stilettos that have to be at least 10 inches tall. The pink contrasts wonderfully against the black stockings, leading up to a pair of hot pink padded panties, ‘that’s what the extra cushioning I felt was’, I think to myself. I can’t help but reach down to touch the panties and feel very, very thick foam, realizing that I can’t feel the touch at all in my caged clitty, while also seeing the telltale controller and pump from my plug dangling from the panties. Above that, I see a hot pink and black dress with an integrated petticoat that extends out about 12 inches from my body in every direction, nicely framing and highlighting my padded panties for everyone to see.

I take in my hourglass figure as I see the top of my dress struggling to cover the massive fake breasts as the dress ends just above the nipples, leaving nothing to the imagination. Just as the dress ends, the hair starts, and boy is it some hair! A matching hot pink wig adorns my head, adding another good foot to my overall height and cascading down in wonderfully thick curls that perfectly frame my heavily made up face; a face that could grab the attention of a room all on its own, from the large, luscious, red lips to the thick and long eyelashes and the incredibly loud and vibrant glittery white, pink, gold, and black eye makeup that runs right up to the expertly done arched eyebrows. “Wow, Mistress, you have really outdone yourself this time! It’s a good thing I’m only about five feet tall, otherwise I wouldn’t be able to fit through any doorway! I barely can now. But, just, wow. This is incredible! But what’s the occasion for something like this, Mistress?” I ask, still in awe of my transformation.

“Well that, much like everything else today, is still a secret to you. But don’t worry, you’ll love it!” Mistress exclaims as she gives my plug a few pumps and starts up the vibration. “Now, if you’ll follow me, oh and grab that bag right there, Sissy,” she commands as she clicks a leash to the front of my posture collar and points at one of the duffel bags still sitting on the bed. I quickly grab the bag and follow Mistress out of the room, down the hallway, and, with some help, down the stairs.

“Now, Sissy, let me help you down onto your knees. There we go, here, let me get this big ball gag into that lovely painted mouth of your’s. I’d really love to blindfold you too but I’d rather not mess up my wonderful makeup job so you’ll just have to see everything that’s going on.” I can feel the gag being buckled and locked behind me as my jaw is forced wide open, ensuring drool will be constantly running down my exposed chest. Mistress quickly grabs my hands and cuffs them behind my back as well, giving them a nice resting spot on top of my petticoats. “Alright, I think that’s good for now, Sissy. This is going to be a big day for you so you’re just going to have to trust me, okay? We’re going to be doing things I know you’ve always fantasized about and I know you’ll love them, no matter how humiliating they are, but that’s kinda the fun part isn’t it? Now get up and follow my lead,” instructs Mistress as she gives my plug a couple more pumps, helps me to my feet, grabs the duffel bag, and pulls me towards the door on my leash.

“Mmmpphh! Mmmmppppphhhhh!!!” I try to protest going outside like this, but Mistress is having none of it.

“What did I just say, Sissy? You just have to trust me. But that little protest did earn you a few more pumps to that plug, just keep that in mind today.” With my plug now inflated to a slightly uncomfortable level, Mistress opens the door and pulls me outside behind her.

To be continued….