Dressed and Shared as Her Sissy

Chapter 1 April

“Were you a good boy for me?”

“Yes, Lady Jane, of course!”

She crosses her arms and I see the tail end of a tattoo peeking out. “Should I believe that?”

“I can prove it.”

Now she looks bemused, with an eyebrow arched. “You can start by showing me right now.”

My chest tightens. When it was just pictures, it was one thing.

Online was easy. Meeting her for the first time in real life — that’s something else.

Exciting, yes, but terrifying, too. She’s stunning and I’m just…

well, me. I’ve spilled all my guts to her and told her all my secrets, everything that excites me.

So seeing her for real is almost a formality.

It’s not like I haven’t fantasized about this a million times.

I planned for everything, worked through any eventuality.

But no plan survives first contact with the enemy.

“Oh, those are very cute. Have I seen those before?”

My hands shake as I slide my pants down over my stocking-covered legs.

I feel Jane’s eyes slipping down my body as she takes in what I’m wearing beneath my pants and shirt.

Even when she only existed as a username and a face on a video call, it didn’t always seem real that the Lady Jane existed. Seeing her in person…

“No, Lady. I… They’re special for today.”

“You have such darling sissy taste.”

It makes me twitch in my panties to hear it. Jane doesn’t miss the small movement and she grins from ear to ear. “You look so precious. It almost seems like a shame to take them off.”

I shiver. I want her to and she knows it.

After months of teasing and touching myself as she whispers sweet, delicious dirtiness into my ears, all I want now is to finally feel her hands on my body.

She didn’t give me a hug when I met her this morning or even shake my hand.

“Because,” she whispered into my ear, “It will be so much more fun to wait until I can touch you the right way.” Even in greeting, she cannot help but be dominant.

“What if I did it myself?”

I slip my fingers into the lacy yellow waistband of my thong panties, tugging them out far enough that my matching garter straps curve outwards above them.

My entire outfit is a matching set — sunny yellow lace with ruffles along the edges, studded with pink bows and pale blue rosettes.

Even the stockings are the same color and covered in a floral lace that makes me feel like a tulip field.

“Haven’t you had enough of playing with yourself?” She leans in, her lips so close to mine I could lean forwards and finally kiss her. “Wouldn’t you rather have someone else do it?”

“Yes,” I say, but it comes out as a moan. I can smell her perfume, soft and sweet. I can almost feel her fingers on my skin. I’m rock-hard in my little panties, trapped within the silk and lace. It wouldn’t take much for her to free me.

“‘Yes,’ what?”

“Yes, Lady Jane.”

She grins and it’s ice-cold. “If you’d asked me the right way, I might have. But now you’ll have to wait.”

I try and fail to stifle a groan. It only seems to excite her more.

Her hand moves to her thigh and slips slowly up towards them hem of her tight black dress.

My gaze flickers between her burning eyes and her skirt as she hikes it up.

A black and red snake is tattooed on her thigh, curling around it and disappearing beneath her skirt.

I can see more and more of it until finally I see its head — or at least where its head should be.

It lays on her belly, its mouth open, tongue out, severed from the body.

The thin line of her bikini panties runs in the gap between them.

“I just love a pretty sissy girl on her knees for me. Do you wish you were touching me right now?”

“Yes, Lady Jane.”

A long fingernail hooks into the sheer black panties and pulls them out.

“Wouldn’t you love to feel how wet I am right now? To taste my arousal?”

I shiver. She knows exactly how to work me. “Oh, yes, Lady Jane.”

The finger slips along the waistband and then finds her wetness behind the silk.

She sucks in air the instant she touches herself, eyelids fluttering as her fingers begin to work.

It makes my chest tight to see it. Every muscle in my body aches to launch me from the floor and take her like I’ve dreamed about for months.

But I know better. I know to wait until she gives me permission.

If she ever does.

“Oh, fuck,” she breathes with a satisfied grin. “This must be so hard for you.” She nudges my throbbing panties with the pointed tip of her stiletto to emphasize the point. “To be so close to what you want and be able to touch it.”

“I could.”

She giggles. “If there’s one thing I know about you, April, it’s that you’re going to be a good girl for me no matter what I do.”

April. It’s light and airy and floral. The name matches me, matches my lingerie. It makes me feel pretty. I repeat it softly, tasting it like I wish I was tasting her.

“And you have been a very good girl, waiting for me this long.”

I let myself get excited, feeling it bubble up in my chest. Her fingers are still working in her panties.

Now her breathing is coming faster and her high cheekbones are tinted with excited pink.

It’s agony being on my knees like this and knowing that no matter what I do or what I say, she won’t give me what I want until she wants to give it to me.

“Thank you, Lady Jane.”

“Good girls get rewarded. Do you think you deserve a reward?”

I can smell the trap. “Only if you think I deserve it, Lady Jane.”

She beams at me. “Clever girl.”

This time when she bends back down, she does touch me — just now how I want.

She darts past my lips and stops when she’s next to my ear.

But she doesn’t ignore my mouth as she begins to whisper.

Her wet fingers slip inside, flickering across my tongue.

I can taste her on them, so sweet and so strong.

The perfume is everywhere around me and her hair brushes against my cheeks.

Every sense is filled with her. When she speaks, it seems to fill every corner of my mind.

“Go put on the dress I got you.”