Desperate Measures Ch. 00: Prologue

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A young man discovers what it's like to be a woman.
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MissLana
MissLana
13 Followers

I was getting desperate. The month before had been such a happy month. I'd finally finished college, getting a law degree. The world was my oyster, or so it was said. A month later proved the lie. Very few companies were willing to hire someone fresh out of college, with no work experience. And the few that did offered so little in terms of salary I still wouldn't be able to make rent, let alone allow me to indulge in my personal hobby: X-Change.

------

It all started my second year of college. Before that, I'd have considered myself the stereotypical heterosexual dude. The pressure of law school was getting to me though, and the occasional hookup or one night stand just didn't do it for me any more, if indeed they ever did. One of my room-mates offered a solution.

"You should totally try this." Said Mike, barging in my room unannounced as he so frequently did.

"What is it now?" I asked, tiredly. He'd come bearing miracles before, and each of them was a waste of time and money. Mike, I'd decided, was rather gullible. The fact that it all seemed to work for him was further proof of this in my eyes. The placebo effect had a strong impact on him. I should offer a quick description of us. Mike was slightly above average height, a tad chubby, and with a permanent red face, as if constantly excited about something.

Me? I suppose I'm average everything. Average height, face, posture. You probably wouldn't notice me in a crowd. Which is of course what made that escapism so enticing.

"You're not going to believe this, but I have a pill that can change you into a chick!"

I raised my eyebrow sceptically. Sure, I'd heard the rumours, but dismissed them as being just that, rumours. At this point in time, X-change was decidedly an underground thing. I suppose it's not exactly mainstream now, but most people have at least heard of it, and the younger generation has certainly embraced it's potential for parties.

I had occasionally wondered what life would be like as a girl, and I now remembered getting ridiculously drunk last month and saying as much to Mike. Mostly, I dismissed these thoughts as being unmanly.

------

These thoughts had originally been sparked at a frat party of all places. The president of the frat, a notorious drunk who groped anything with tits was conspicuously absent, resulting in a rather more relaxed atmosphere. I even danced with a couple of girls, and while I've never been very good at leading, I do love to dance.

As the party progressed there was a steady stream of jocks making their way from the party upstairs. In and out of itself this wasn't unusual. What was unusual however is that they were not accompanied by drunk girls about to get royally fucked. As I was getting another beer, one of them that I knew from my civil law course made his way downstairs. He looked exhausted, but had a very happy grin on his face as he plopped himself in a comfy chair. He nodded at me and at the beer I'd just poured. Having always been slightly intimidated by him, his height and muscles made him a towering giant to me, I brought him the beer.

"Thanks man, I needed this." He said, downing the beer in one chug. Nodding at the beer again, I went and got him another.

"That whore is insatiable, just can't get enough. Even a wimp like you will do I think." He said, grinning nastily, taking another sip. "Go on, get up in there!" He commanded me. As I walked up the stairs he whispered something I couldn't quite understand but which sounded like "That is, if you don't end up joining her..."

Upstairs, the music from the living room was dampened, allowing me to hear a moaning sound from the room at the end of the hall, where a faint light could be seen shining from under the door. Slowly edging towards the door, the moaning got more pronounced. I gathered up my courage and opened the door. What I saw was...amazing.

A blonde girl, from the looks of it slightly older than me, thin with large boobs, was getting gang-banged by what looked to be at least a dozen men. And enjoying every moment of it. From the way she held those cocks in her hands as she was bouncing her cute ass on two others it was clear she was running the show. Moaning whenever her mouth was full, telling the guys present to fuck her harder when it wasn't.

She looked straight at me. "Fresh meat!" She ordered the guys to get me up there, and when I was, roughly pulled down my pants. "You'll do." she smirked as she sucked me down, blowing me until I got hard. I fucked her for a bit, her overpowering demeanour making me blow a lot faster than I was used to.

I remember leaving the room in a daze and masturbating furiously when I got back to my room. I learned two things about myself that day. The first was that having sex as a girl looked decidedly more fun. The second was that I was nothing like the little blonde slut commanding an entire room to do her bidding. No, what I got off on was someone giving me the orders.

-------

Jerking my thoughts back to the present day I looked at Mike's grinning face.

"Supposing you're right and it's not another fake wonder drug someone sold you for a generous chunk of your monthly allowance from your rich daddy, why would I try it?"

"Because, dude, you've been very stressed out over those midterms lately. And what better way to blow off some steam then a good old session with your right hand?" He said, smiling at me while waggling his eyebrows in a highly suggestive manner.

"All right, first, gross, don't talk about that with me. Second, that still doesn't explain why I would need to be a girl for that." I said condescendingly, trying to hide my enthusiasm. Could the rumours be true? And could Mike actually have gotten some, instead of just being conned as usual? Even the fact that the second option was vastly more likely, I couldn't help but get excited.

"Because..." He said slowly, as if explaining something to a rather dim child "Orgasms are far more intense as a girl, and if you don't believe me, think of Danielle."

"Who?"

"Oh come on, don't be like that man, you were at that party! I know you went upstairs and fucked her. You and half the campus."

"Oh, her, yeah, well, I guess I did." I said, stammering a bit. I shouldn't have been surprised. For all his faults Mike was surprisingly good at ferreting out the latest gossip. Daydreaming a bit after being told to remember, I see her clearly again. Surrounded by naked students on all sides, a sheen of sweat covering her body. Her rock hard nipples on her perfect tits, swaying with each thrust of cock in her pussy and ass. And her face one of pure ecstasy, as she was worshipped by the mass of men around her.

Mike leaned forward in a conspiratorial manner. "Danielle is actually...Daniel Rhine, president of the frat, and heir to the Rhine fortune."

My mouth fell open of shock, my eyes widening.

"No way..."

"Yes way, and be careful, a fly might fly in." He said, grinning.

My mouth snapped shut, and then opened and shut a couple of times as I digested the information.

"So, he was..."

"A she, and yes, getting fucked six ways from Sunday. It's a pity you missed the finale where everyone present showered her in cum. Although I have some pictures if you're interested..."

I almost snatched them out of his hand, my face betraying my eagerness. He chuckled and gave them to me, along with a single pink pill.

My eyes devoured the pictures, while I subconsciously licked my lips. They depicted Danielle on her knees, semen already leaking from her well used pussy as the men who were left standing formed a circle around her. The men had their hands on their cocks, and it didn't take much imagination on my part to see the scene as it had been. Her in the middle, with them jerking on their cocks. What struck me again was her poise and presence. Even in this situation, what should have been a submissive pose, on your knees waiting for an eruption of cum to cover you, to mark you as their whore, their property, she was in control. She had a wide smile on her face and her eyes seemed to be daring them to do it. It was for her pleasure this was happening, and theirs was merely a happy coincident.

Subsequent pictures showed one man after another reaching the brink and shooting his load on her. Danielle basked in it, her mouth open to let out a moan. The final picture was just of her, her face and tits dripping with cum. Her eyes, barely able to open, looking at the camera, her lips forming a contented smile. There was no question that she took their offerings as a form of worship.

Mike chuckles as he saw me daydream whilst looking at the pictures. "Good huh? Who'd have thought it, alpha male Daniel, on his knees like an eager little cumslut."

I looked at him unbelievingly. Did he really think that, looking at these pictures? When he said the word cumslut though, I felt a charge running through me, and for a brief second I saw myself, on my knees, being just that. I then remembered what was in my other hand.

"I'm going to go out for a bit." Mike said, grinning as he saw me look at the pill. "Take whatever time you need yeah? I'll see you tonight, we'll order pizza or something."

I nodded slightly, lost in thought as he chuckled again while he was leaving.

I don't know how long I looked at that pill. I put it down several times, and glanced at the pictures again. Finally, before I could stop myself, I grabbed the pill and swallowed it down.

Nothing happened at first, but then I felt something change inside of me. I staggered back, hitting and then falling on top of my bed. My body was getting hot, my chest expanding, my penis diminishing. My face...shifting slightly. It felt weird, but in a good way, as my clothing grew loose in some places and too tight in others. I struggled out of my jeans as my ass was filling out.

When it was over, I felt weak, it took me a few tries to get up. When I did, I stumbled over to the mirror. I gaped at the image, unbelievingly. I took off my glasses, and then put them back on again. The image hadn't changed, instead of the average man that usually stared back at me, a young, attractive, woman was looking at me, her eyes wide and mouth open in surprise. Her breasts were stretching the shirt, which I suddenly realized was not very comfortable with my new physique. Her legs bare, she was wearing a boxer short which gave her the look of a girl wearing her man's clothes.

Arousal hit me, as I fully realized my change. My nipples grew harder, showing clearly through the shirt. My legs were rubbing together unconsciously. My left hand drifted towards my nipple, giving it a small swipe. I almost fell down from the sensations, I was not expecting to be so sensitive!

I took of my shirt, staring at my new assets. They looked perfect to me. Not too big, not too small, I'd estimate a little more than a handful. Of course, I thought looking at my new small feminine hands, that's not exactly true for me any more. A giggle escaped my lips. Surprise was again on my face as I heard the little feminine laugh come from me. Was that really me?

My hands continued exploring my new body, marvelling at the touch, at how sensitive I was. The boxers were quickly discarded as I looked at my new sex. A tiny pussy stared back at me. Slightly swollen and moist with excitement, with a budding clit perched on top. A slight twirl showed a perky ass with a bit of bounce, before I moved my eyes back to my pussy, fascinated.

I stumbled back to the bed, and lay down, breathing faster. There was no question in my mind what I was going to do. My hands moving around my new body, squeezing my tits and lightly pinching my nipples, softly rubbing circles on them with my index fingers. My right hand continued its exploration downwards, crossing my mound and finding my new pussy's moist lips. I bit my lip before letting out a small moan. I brought my hands to my mouth and wetted them before continuing, tasting myself a tiny bit. Bringing my hand back down, I hesitated slightly before slipping a solitary finger in. I moaned loudly at this, the sensation being far more intense than I ever imagined. My finger moved, tentatively at first, but faster as time went on, trying to quench this overwhelming desire building up in me.

Another finger joined the first, as my left hand was getting rougher and rougher with my tits, pinching and squeezing. My fingers thrust in and out of my sopping pussy, my thumb grazing, by accident, across my clit.

An image forms in my mind, unbidden. First I see Danielle, proudly receiving the semen splattering on her face. The image shifts slightly and it's me sitting there. The image shifts again. I'm sitting on my knees, looking up at a large cock. My eyes aren't commanding, my presence does not radiate control. He comes, covering my face with his seed, marking me as his property. I sit there, submissively, knowing my place.

I come, my back arching upwards, a moan turning in what could have been a scream, coming from my mouth. My entire body was electrified with orgasmic glow, tensing as waves of pleasure wash over me. My mind is momentarily numb, as I slowly come down from the heights.

A single word escapes my lips. "Wow..."

-------

After changing back (I took what was intended to be a quick shower first, but it escalated a bit, despite some soreness) and admitting to Mike that yes I did enjoy myself, he told me he could supply me with more, at cost.

That's how it began, I took the pills to relax, to unwind, and apart from a couple of incidents, enjoyed myself immensely. So much so that going without was getting hard. Which is why, after being unable to find a paying job, not only was I going to lose my apartment but I was also unable to pay for a steady supply. Which made me a bit desperate.

There was only one pill left in the bottle, as I scanned the internet for listings. Every interview I'd had the past two weeks had been a bust. And then I saw the ad for a personal assistant. Not exactly what I had in my originally, but maybe I could work myself up? I had all the qualifications, legal background, typing skills, but there was one qualification I didn't have. They specifically wanted a woman.

I looked at the last pill, it just had to last long enough for the interview. I said to myself, just ask for an advance, get a steady supply, and they never need to know, it's just until I can find something better. I sent in my resume, along with a picture I'd taken not too long ago when I wanted to see how sexy I'd look wearing office outfits.

I got a response the next day. "You are expected Monday the 23rd." I chill ran down my spine. Could I go through with this? But I didn't have a choice, did I. So I steeled my nerves, took a pill and showed up at the company, a large psycho-pharmacology firm, trying to disregard my unease at the first sentence of the letter. "You are expected."

MissLana
MissLana
13 Followers
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AnonymousAnonymousabout 1 year ago

So a guy takes a pill to transform into a woman. He likes the idea guys are going to use him/her for gang sex. This could be interesting to see if he learns how to be more considerate towards women. Maybe he swaps gender for the girlfriend so she can have a bisexual lover.

AnonymousAnonymousalmost 5 years ago
Great start

This is a great start, just need the next chapters now. please.

Mosc47Mosc47over 7 years ago
I definitely need more!

This story was way to hot to be abandoned. I see there have not been any additional chapters in a long time, but I keep hoping that the story will continue.

AnonymousAnonymousover 8 years ago
Beautiful

Please, please write some more

AnonymousAnonymousabout 9 years ago
it has potential

I think you are setting up a good foundation and I would love to see the story progress. I think you should make the main guy seem more intelligent since he has a collage degree in law. I would also like him to have a name.

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