Pretty Woman: the beginning

3 min read

“I saw you, you know,” she says, “rifling through my closet. Found anything you like?”

I had taken advantage of her being gone for the whole day to look through her clothes. I hadn’t heard her come back in, too much in awe of how the silky fabric felt between my fingers.

If I could, I’d run away,

As if she can read my thoughts, she takes hold of my hand.

“Don’t worry,” she says. “I always thought anyway…”

“You always thought what?”

She shrugs. “Well, I always thought you’d make a very pretty woman,” she says, making a vague hand gesture towards me. I glance down, but I already know what she means. She means my 150 pounds spread on 6"2'. She means the wavy hair I keep shoulder length, tousled. She means the softness in my voice and the gentleness in my eyes.

“Maddie used to say I’m at least a third female,” I muse aloud. “Always figured it was kind of a back-handed compliment.”

“Never mind what she thought, Maddie’s a bitch,” Jane scoffs. “I’m pretty sure coming from her it was no compliment.” She would know. My ex and Jane used to be best friends in college.

Jane goes on, her bright eyes twinkling. “If you wanna put a number on it, you’re more like 45 percent woman anyway, and you can be sure it’s a compliment coming from me.” She traces my face with her fingers, gently, carefully, and the intimate gesture makes me feel better.

“If that’s what you’re going for, you’d have no problem passing for a woman,” she says. “You know what, I’ve got an idea. Go to work and when you’re done come straight back here.”


“Go on,” she says, slapping my butt. “Mami’s gotta go to work.”

All day I’m apprehensive and giddy. Jane is never afraid to push my boundaries and while I love her for that, sometimes I wish she wasn’t so brash about it. But when I get home, and I see the clothes she thinks might fit me best all laid out on the bed, I can’t say no to her. Not when she’s obviously given this so much thought. I just hope I won’t regret it.

It’s funny that she’d own so many frilly clothes anyway. She’s always told me that she loves how the straight lines and no-nonsense style of business suits and ties boost her confidence. Why be a constant client of Victoria’s Secret then?

“You’ll look killer in this,” she says, holding up a long dress which I know flatters her curves as well. “But first…”

“First?” I ask anxiously.

“First we’re getting rid of all that hair,” she says with a grin.

I’ve never had much facial hair, but it’s the first time I’ve had my public hair trimmed away. I’ve never felt so naked — tall, slim and hairless.

“Here, try this,” Jane says, handing me a crimson dress. The feeling of the silky fabric gets me hard. She stares at the obvious bulge and smiles. “It’s ok hun, it is a very nice dress.”

I love these dresses — how they shape themselves to my curves, becoming a second skin. I feel a few inches taller. More powerful, too.

Jane nods. “I like this. I like how you look in it.” She claps her hands. “Oh, almost forgot. I got something for you. You’re gonna cream about it.”

She fetches a pair of brilliant boots. She kneels and helps me into them, then looks me up and down.

“I knew you’d be a pretty woman.”

She leads me by the hand to the bathroom and has me sit on a chair. “I really think some lipstick would do you good.”

She purposefully nestles against my long frame, her hand wandering down to my hardening dick.

“Don’t move,” she whispers in my ear. “You wouldn’t want all that hard work to go to waste, would you?”

She applies the lipstick to my lips, letting her other hand dangle down my body, brushing my swelling dick, as if she isn’t completely aware of every movement she makes. It’s torture and pleasure, all rolled into one.

When she’s done, I have to admit I look good. Given a dim enough bar I’m confident I could seduce anybody. But right now seduction isn’t on my mind, right now I can only think of Janet. Janet, who not only doesn’t judge me for liking girl’s clothes, but has even helped me see what I would be like as a girl with as much enthusiasm as she brings to everything she does. Janet, who for some reason has chosen to be with me even when I’m boring old Brad.

Janet says, “Lie down. You seem nervous.” I lie down and she wraps herself around me.

“My lipstick is going to smudge,” I say.

She just laughs and says, “god, you’re such a girlie.”

She keeps kissing me and it keeps feeling good and my dick keeps growing under the rolling movement of her hips. Finally, she starts kissing me all the way down, until she reaches my penis and engulfs it with one wonderful movement of her mouth.

She starts breathing through her nose, bobbing up and down quicker and quicker until I erupt. She swallows everything and gives me a full kiss.
It doesn’t taste bad, a bit salty and rough, but not bad.

She starts stroking my cheek, looking into my eyes. “You seemed a bit nervous,” she said. “I had to do something about it. Now go to sleep,” she adds with a wicked smile. “In a few hours, we go dancing.”

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