Chapter 4 Milked
“You’re so hard,” she purrs, arms wrapped around me.
“I’ll take care of your girly needs.” My hips buck forward on their own — I can’t believe that this is happening.
Her dress is exquisite, and when I think about the petticoat beneath, the lingerie, the curve of the garter strap and the lace trim on her panties, I just need more .
Marilyn chuckles knowingly. “Mm, yes, that’s a good girl. And you’ll make a very good girl, won’t you? All dolled up like this?”
“Yes!” The word comes out as an urgent cry. I press myself into her dress harder and she gives me a squeeze back, fingers dancing across the top of my ass before sinking in and grasping hard.
“That’s a good girl,” she says, voice dropping even lower. “A very good little sissy girl.”
Her fingers tense again and this time I feel her nails dig in through the sheer fabric of the panties.
She presses into my cheeks and pulls them apart while pushing herself forward, sending another rush of silky pleasure surging through my cock.
I moan and she kisses me again, deeper and hungrier than before, her lips sealing over mine as her tongue plunges into my mouth.
This is beyond any fantasy I’ve ever had.
My legs turn to jelly under Marilyn’s expert touch, barely able to hold me upright without her.
“So pretty,” she whispers into my ear when she breaks the kiss. “This babydoll puts everything on display, doesn’t it? It exposes all your most sensitive parts.”
I’m too lost in the sensations to fully understand what she’s saying: her dress against my throbbing cock, her petticoats brushing against my stocking-glazed legs, the swish of my babydoll around me, the squeeze of the garter belt and its tug on my nylons.
I suddenly become utterly aware of what I’m wearing and what’s happening, but instead of making me stop, it only makes me want more.
And then she slips her finger inside of me.
“Oh, oh! ” I squeal. “What are — what are —”
“Shh,” she says. “Exactly what a girl needs.”
She pushes in and out very gently, my hole tightening around her.
It’s pleasure like I’ve never experienced before, thundering through my belly before settling at the base of my cock.
Even as she starts to finger me, I can’t seem to stop thrusting into her dress any more than I can stop myself moaning.
I know I shouldn’t want this — but I do.
“Be gentle,” I whisper.
“Oh, dear, of course I will,” she coos. “I don’t want to hurt such a sweet, lovely thing.
” She pushes in deeper, past the tightness of the ring that gives way easily once she passes.
Her hand is warm and smooth inside of me.
There’s a moment where she just leaves it there while I pant and gasp and squirm between her grasp and her dress, until at last I begin to settle down. She smiles.
“At least not _yet._”
Another knuckle in, deep enough now for her to press outwards and send little sparks up my back.
My body stiffens as a new sensation joins the fray, one I’ve never felt before.
When her fingers curl to brush against something inside of me, all those other feelings fade away; pleasure surges through me like electricity shooting up my shaft, and when I cry out this time, it isn’t with surprise, but ecstasy.
“Oh — oh — Mar — Mar —”
“Miss Marilyn,” she murmurs. “That’s your sissy spot.
This is where good girls feel pleasure — not from that useless little clitty.
Doesn’t that feel divine? Don’t stop rubbing yourself, dear.
I want you to make your big sissy mess right into my dress while I finger you.
This is the best pleasure a girl can get.
All wrapped up in a frilly little outfit, like a present, just for me.
But you don’t want me to unwrap you, do you, dear? ”
“N-n-no, M-Miss Marilyn!”
“No, of course not. You want to feel all this lovely satin and lace. It gets you so excited, I know. No, Jessica, I’ll leave you just the way you want. And I’ll show you all the special pleasures that girls get to have and boys can only imagine.”
She drags out the s in Jessica, too, and it sends pinpricks up my back.
The next time her fingers brush against my sissy spot, I let myself go completely and start thrusting into the satin folds of her dress hard enough that each stroke pushes me up on my toes.
My moans have turned into high-pitched, girlish squeals.
Her smile widens and she pulls me close to her as she starts finger-fucking me in earnest. A deep shudder wracks through my body; the garter belt and stockings pull tighter on my legs; my breath comes hotter and faster until it’s like there’s nothing else in the world except Miss Marilyn and me.
“Good girl,” she coos into my ear. “Good girl, good girl. Cum for me. Show me how excited these pretty things make you.”
“M — Miss Marilyn!” My hips buck forward as if possessed.
“Just think, Jessica,” she whispers straight into my ear.
Straight into my thoughts. “Maybe we’ll put you in a darling little nightie with pretty bows and ruffled trim?
Something with so many slippery layers of nylon that you’ll feel like you’re on a cloud.
Of course, they’ll have to be see-through so I can see exactly how excited they make you.
It’s very important to me that my Jessica always feels especially sissy and sweet all the time.
That means nothing but the girliest, most delicious outfits for you.
Once we get you out of your nightie in the morning, I have the most beautiful dress I have been dying to see you in.
The petticoats are so dense you almost can’t hear yourself when they get moving.
You’ll be the prettiest girl I’ve ever played with, Jessica.
All you have to do is make your sissy spurties right into Miss Marilyn’s dress. ”
My body seizes up in one final convulsion; every muscle tenses at once.
She wraps both arms around me tightly as she finger-fucks my girly spot even faster, cooing soft nothings into my ear as I let out one desperate squeal after another.
But despite the pleasure, the overwhelming power of her soft monologue in my ear, the fantasy of it all — my body just won’t let go.
“Good girl,” she breathes.
And then I explode. The first wave of ecstasy washes through me like a storm surge: intense and wild, powerful enough to take me by surprise, even though I’m expecting it.
The second is bigger than the first; the third larger yet.
With each spasm of release, it feels like she’s dragging another load from me.
I thrust over and over again, sending more and more spurts across her dress until my balls finally give up their load.
Every thrust forward makes a little more cum shoot into her satin folds.
My body jerks uncontrollably between Miss Marilyn’s firm embrace and the unrelenting pressure of her fingers against my sensitive spot, and every time, the sensation overwhelms my mind and forces my body to give in to the pleasure once again.
Each eruption makes my head swim and my hips jerk.
I don’t think there’s any part of me that doesn’t feel good — really good — for one endless moment.
And when I open my eyes, the look on Miss Marilyn’s face tells me exactly how pleased she is with me, too.
“Well, now,” she purrs. “My sweet little Jessica is going to be just perfect.”