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A Strange Request

by ParanoidLord

A Strange Request

(This is a story I produced in a fit of arousal under some fairly intense hypnotic programming. I did some minor revisions afterwards. If you're into fiction relating to feminization hypnosis, you'll probably find it to your interests.)

"I'll give you twenty dollars to ejaculate on this dress."

It's a lady. I don't know her; she looks to be about twenty five, with long brown hair, blue eyes, five feet and six inches and maybe about 130 pounds. All I have to go on is sensory information - she looks very generic. Attractive generic, perhaps - Her hair's pretty, her face is pretty (probably makeup), her body's proportions are nice, and so forth. But her genes are fairly common-


I just realized she asked me to spooge on a dress that probably belongs to her.

"Self explanatory. You get your semen on this dress, preferably on the inside lining, and I give you twenty bucks. Okay?"


"Sure, it's shocking. But there's no catch. If you say yes, I'll wait outside for you. Once you're done, come out, show me the stain, and I'll give you the money."

"Okay, better question. Why do you want me to do this?"

"Don't ask questions. I'm offering you twenty dollars to masturbate, and I don't really need the dress back after you're done. Do you want to do it or not?"

I'm still feeling the deal is a bit suspicious, but...

"Alright, fine, I'll do it! Holy Jesus, you're pushy."

"Good. I'll wait in my car." She tosses me the dress and immediately heads to the aforementioned car. I close the door before any of the neighbors can see. I'm not very familiar with them, but I don't want them to think too badly of me.

Once I get up to my bedroom, I inspect the dress I'm expected to cum on. It's knee length, and appears to be made of dark purple satin, almost black. It has short sleeves that would barely cover the shoulder of someone wearing it. The silhouette appears to flare out quite a bit; I lift up the skirt and note that it appears to have a sheer petticoat built in. Under that, the dress is fully lined in the same purple satin. The label says the dress is 100% silk, and is a 'medium' size from some vendor I can't recognize. I'm a guy, I can't be expected to keep up with women's fashion details.

I briefly entertain the idea of reneging on the deal, but the thought strikes me that she could do all sorts of nasty legal things to me if I don't follow through. Besides, I'm being paid for my 'service'. Do I really have anything to lose? I suddenly notice that I have removed all my clothes. Not sure why I did that, I just would need to unzip my jeans to free my penis and make it available for stimulation. Oh well, I can redress later. So I carefully turn up the skirt of the dress for easy access to the lining and let it drop to the floor-

As it slowly floats down to the floor (Not so much floating as draping in a little pile), it just happens to brush up against my currently flacid penis. I feel a smooth, slippery stroke against my cock... it's like an incredibly smooth, delicate hand (most certainly female) just seductively rubbed it, like the prelude to the ultimate handjob. Before I can properly parse this, I feel myself bending rapidly in an attempt to grab the dress before it crumples on the floor.

It feels surprisingly good against my hands. I seem to remember it feeling surprisingly pleasurable against my skin beforehand, but not paying attention to that sensation. Initially, I was just planning to pull up some porn and jerk until my semen fell on the garment in question. Now, I don't think I'll even need porn. So I drape the lining over my penis.

*Stroke,* says an unidentifiable voice in my head. It seems to be female. I ignore it, since it's not offering anything new. After fumbling about for a few seconds, I find that wrapping a bit of the satin around my penis and pulling the relevant fabric up and down on my dick is the best way to go about this. I'm genuinely surprised - masturbation has never felt quite this good. It's like a handjob, it's like penetrating a vagina... it's like making love to a dress. That's one thing I never thought I would never do.

The rest of the dress is draping over my legs. Every stroke makes me feel pleasure not only in my penis, but also wherever the fabric moves over my legs. Compulsively, I adjust the dress so that the bodice is touching my chest. Suddenly, I hear the strange female voice in my head again.

*I feel good,* it says. Who is it? I know I feel surprisingly good right now. My arousal is beginning to build up, especially wherever the dress is touching me.

*The dress makes me feel good,* continues the voice. It sounds surprisingly familiar. I am trying to rub the entire thing over my body. I know my penis is now touching the outside, but I figure that I can pull away and spooge in the dress's lining when the time comes-

*I wonder what it would be like to wear the dress,* the female voice interrupts. Seriously? Wouldn't a woman know what it's like to wear a dress? But the voice is giving me some strange ideas. I wonder what it's like to wear a dress. As a man, I've never actually put on any women's clothing, but if a satin dress feels this good, then maybe I should try it at least once...

I look at the dress. It looks like it would fit me, although it might be a bit tight in the chest. I suddenly notice there's a zipper on the back; I probably wouldn't have to pull it up all the way to get a snug fit, anyways. So I pull the zipper down, still clutching the dress against my body like I'm having sex with it. I am having sex with it, in fact. I guess the first few strokes were just foreplay.

So I start pulling the dress over my head. I feel a strange tingling come over every area the inside lining covers. But it feels good. I keep pulling, and eventually my head enters the neck of the dress. I put my arms through the tiny sleeves. I've broken a frontier by putting on a dress. Why does it feel so natural?

*Because I'm a woman.*

"Wait, what?" I blurt out. My voice sounds a bit higher and softer. Surely wearing a dress doesn't make me female?

*I like wearing satin dresses.* I don't know why, but this female voice that I can't place is at least sometimes saying things I can agree with. I mean, I'd never worn women's clothing until today, and it does feel shockingly good.

My hands have idly drifted down to my crotch and began to stroke the large bulge where my penis is. Every stroke sends pleasure through every part of my body that the silky smooth satin covers.

*I need to orgasm in my dress.* I might as well accept the voice, wherever it comes from. My strokes are slower and gentler now, but no less pleasurable. My hands feel soft where they touch the dress.

*I am a woman.* I wonder what it would be like to be female, and continue to stroke.

*My clitoris is engorged.* It is. Hold on a second. I don't have a clitoris, I have a penis. Whatever. It feels good to stroke.

*It feels good to masturbate in my satin dress.* I really hope this lady will let me keep it. I want to try masturbating in this dress at least one more time after this.

*It feels good to wear my dress.* This is also true.

*I like how it feels against my breasts.* They're small, but they're sensitive, and one of my hands moves up to stroke my breasts through the bodice. I'm not surprised by how pleasurable this feels.

*As a woman, I like wearing silk and satin.* I do like wearing satin.

*My dress makes me feel feminine.* Surprisingly, it does. The pleasure is spreading to the uncovered parts of my body.

*I am a woman, and I need to wear women's clothing.* I know that women tend to wear at least panties under their dresses, and generally wear shoes outside. I think I should purchase some of those. Maybe I can get a nice pair with the money I'm about to get. I am getting awfully close to orgasm.

*Women have female orgasms.* Also true. My girly body probably won't be able to take more stimulation before I climax.

As it is, it takes me only 7 more strokes to reach orgasm. It feels like a someone started a fire in my clitoris, except instead of burning, I just feel incredible pleasure. It slowly spreads through my body, but becomes increasingly intense at the same time... I can't help but spasm, and a shrill scream of ecstasy escapes my lips.

I recover after a while. I didn't bother to check how long it took me to reach orgasm. How could I? More women need to understand how good silk and satin are for sexual purposes. Perhaps that's what the strange woman I met wanted me to experience. I lift the skirt of my dress up, and see that there's an ejaculate stain near my clitoris. Quite an achievement, since women don't always cum when they orgasm.

*Something's wrong,* says a strange voice in my head. It sounds oddly masculine. Why would a woman have a male voice in her head? It probably represents something. I don't know enough psychology to check. But I still feel compelled to look at my body.

It's not great. I think I'd be more attractive with longer hair on my head, and I should probably shave my legs. Maybe I could also change my diet to burn off some waist fat and achieve a better silhouette. The male voice doesn't say anything else. I'm thinking about how much better I could look, when I hear my doorbell ring.

I slide on the first shoes I can find, a pair of men's sneakers. Where'd I put my normal shoes? These feel a bit big and clunky. Oh well, better than nothing. I wouldn't want to injure my girly feet by stepping in something suspicious. Looking at the keyhole, I see it's the girl I met. She probably wants to check on her progress. I open the door. She looks a bit surprised, like she wasn't expecting anyone to be home.

"Did you... come for me?" she asks.

"Of course I did!" I inform her. "I'd show you here, but I'd get arrested for indecent exposure."

"...Yeah. Can I come in?"

"Sure." So I lead her to my living room, where we sit down on the couch. I lift my skirt to show her my evidence of orgasm.

"And to think it all came from my vagina," I babble. "I didn't know I could emit so much fluid." It was kind of an exhausting experience, and I feel like I should take a short nap to recharge.

"Cool. Here's your twenty bucks." A bill with the face of Andrew Jackson is pressed into my hand. I try to pocket it, but unfortunately, my dress, pretty as it is, doesn't have any pockets.

"I need to change into something a bit less formal," I tell the girl. "Unfortunately, I seem to have misplaced the rest of my clothes." She stares at me in an odd fashion.

"I have some spare clothes at my house," she responds. "I can take you there, so you can try on some things." She seems a bit more confident now. I guess I really showed her.

"Yeah, that sounds good." So we exit the house, and I sit down in her car. I must've dozed off during the drive, since I don't really remember anything except a nice floral perfume when I enter the car, and the clock jumping about ten minutes from when we start driving, to when we get to her home. It felt like an instant, to say the least.


Rita's Diary, entry for 9/20/2012:

"I'm beginning to have qualms about putting hypnotic spells on clothing. My teacher tells me they'd only significantly affect someone who really wants the effects, but what if they don't? I'd feel awfully guilty if someone got manipulated into becoming something they didn't want to be."

Entry for 9/25/2012:

"I've brought home a stranger. He's sleeping on my couch in full drag and a wig. I'm not sure why I put a feminization enchantment on this dress, but it seems to have completely erased any maleness he had. Technically, his body is still entirely male, so he has a way to go before he can pass for female. But he seems happy, and I seem to have a fetish for crossdressing men and transwomen. I called my teacher about this, and he said I probably shouldn't have done this whole stunt with the satin dress. As it is, the subject clearly wanted to be female on some level. My teacher told me that I should help this new woman transition and get used to her life."


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