It's a Wonderful New Life

I met Sherry at a bar. Imagine that. I often picked up women at bars. I'm a good looking man, have a nice sporty car, cash flows freely from my pockets - at the bar anyway. So I do OK at snagging a tipsy babe for a nights folly. But all of the sudden karma has caught up with me. When I hit on her she told me to back off or I'd be sorry. When I persisted, politely of course, she informed me she was too much woman for me and that if I went home with her she would be happy to prove it. I laughed the good laugh at that one and called her on it. She warned me further, "Look, if you take me home I will demale you. Do you understand that? I will turn you into a sissy fuck toy slave and make you love it above all else. I will teach you to respect and fear women, and never look at one in a sexual way again. I promise you that." She seemed militant about it and really stressed the word promise. Then with a evil grin taunted me, "I can even train you to prefer a man to a woman, choose cock over pussy. I will make you a cock-bobbing, cum-catching boy toy for men." And with that final taunt her girlfriend with her laughed, spitting back and snorting into her drink, obviously astounded at her comments.

But she wasn't scaring me. I was more than a match for some penis-envying, egotistical women's lib militant. "You let me worry about me sugar britches," I challenged back. "We'll see who tames who." I was eager to put her in her place, beneath me, naked, and begging for me to fuck her. Plus I was intrigued. This was a confident if misguided piece of eye candy. And she did have a mastery of language and wit, twisted as they were. So after a couple of drinks with Sherry and her friend Amy, during which the conversation was flirty and polite and never returned to the tit-for-tat 'dick-wagging,' we all went back to her place for the proverbial night cap. I remember having a drink, then getting very sleepy.

I awoke and was immersed in total darkness. I mean it was pitch black, zero visibility. But there was more to it than that. I couldn't move. I was constrained at the wrists, the ankles, and the waist. I couldn't even move my head - at all - and it is pitched up in an uncomfortable position. Worse, there is something in my mouth prying and holding it open. I can breath through my opened mouth but of course it is hard to swallow this way, so a stream of drool has seeped out the corner of my mouth and run down my face and neck. And something is wrong with my cock. My balls are very warm, even hot and sweaty despite the fact the room is chilly. And I can feel my penis sticking up, being held upright through something despite not being very hard. But I can't see a damn thing. And I'm still very groggy and sleepy. Have I been drugged? Was I still at Sherry's house? What the hell is going on here?

Suddenly a red light appears. It is very faint and dim yet surprisingly illuminates the room somewhat due to the total darkness. A fuzzy figure approaches me. I think it is Sherry. I try to say something but I just gargle on my spittle.

"Shhh, be quiet. I need to concentrate" she says as she began to remove the hot packing surrounding my crotch. I try to shake the cobwebs in my brain and focus my blurry eyes on what she is doing. I can now just barely see but make out the contraption between my legs. My cock is sticking through some metal ring despite not being hard. And my balls are split with some sort of strap between them forcing them widely apart as they hang loosely from the heat. There is a pink bow attached to the contraption. I laugh, as well as I could through the gag. This is supposed to demale me? My wrists and ankles are locked in some hard plastic braces of some sort. She pulls the strap between my nuts very tight and the softened testicles tighten and the skin over them stretches. It hurts but my cock cannot help but get harder due to the attention. Suddenly she produces a bag and withdraws a syringe and needle. Erection gone!

"What the fuck" is what I say as I violently struggle in vain against my bondage. But of course all that is audible is a gargling and spitting sound coming out the hole in the device that holds my mouth open.

"Hold still. You wouldn't want me to mess this up would you?" And with that holds an ice cube between the testicles for a few minutes, and then inserts the needle into one. I'm surprised it doesn't hurt any more than it did. Just an uncomfortable sting really, under pressure, like a dentists' shot in the gums. She then injects the other the same way. Needless to say I am greatly relieved when she is finished. I remember thinking 'Damn girl, there's a Viagra pill available now that's a lot easier. Plus I don't need it. Just release me and I'll show your ass.' So when she said what she said next I was absolutely dumbfounded. Speechless, even without the open gag.

"I just gave you a shot of Neutersol. It's a neutering drug that will chemically castrate you. Your balls will decrease in size and shrink to about a quarter of their current size. They will also get very soft and supple. Your penis shaft will also shrink in size both when soft and hard. You will still get erections when aroused but they will be much smaller, even cute. But don't worry; you will still be able to cum when excited."

Of course I couldn't speak, but it didn't matter. The look of horror in my eyes surely said it all. 'What gives you the right' was all I could think. She then set up a full length mirror in front of me allowing me for the first time to see my current bound predicament. Jeeze. She loosened the strap between my balls and reapplied a fresh heat pack to my groin. She then took out an assortment of pills and began to drop them one at a time into my gaping mouth explaining what each was for.

"This pill will help you get and stay sexually aroused for hours on end, even if you do not get erect. This one will increase the sensitivity in your anus and nipples. This one is a hormone that will soften and sweeten your voice and cause your breasts to grow bigger and puffy. This little pill will lower your testosterone levels and make you more subservient and manageable. And this one will help you sleep." She then poured some whiskey into my mouth and despite trying not to swallow it or the pills gravity and physics washed them down just the same. The liquid burned and warmed my innards as my crotch began to reheat. "The mirror will allow you to see the changes as they happen to you. It will be so fun for the both of us to watch as you are demaled - just as I promised you." She then left the room with me in mortal terror of what would happen next. I soon fell into a blissful, deep, dream-free sleep.

When I awoke again she was again removing the heat pack from my crotch. I quickly tried to focus and examine my balls. Damn! They did seem smaller. And my cock seemed smaller too, and was twisted somehow and laying between my balls. Only the metal ring was now required to hold my package obediently in place. And my asshole itched a kind of excited tingly itch. It felt wet. She poured some oil onto my cock and began to play with it. It felt incredibly wonderful and it felt like it got more rigid, yet it barely got harder, if at all. Was it the drugs, or the ridiculous position it was mangled in? And when she stuck a finger inside my ass and wiggled it about I almost instantly shot the puniest little load of spunk. Did I say 'shot?' I should have said dribbled out an almost clear yet slight stream that didn't even look like cum. It looked more like precum but there was too much of it to be that. But I felt like I came. It was a little confusing. Did I cum or not?

"Ah, good. Perfect actually. You are taking to the medications wonderfully." She pinched both my nipples and it excited me immensely yet hurt terribly. They were so tender. My wincing in pain obviously pleased her. "It's time to step up your training," she said and produced some strange clamp-like devices connected by a chain. She attached the clamps to each nipple and tightened them. I thought I was going to die from the pain. Tears streamed from my eyes as I groaned thru my gag. Next she raised the chain to secure it to another one dangling from the ceiling but one of the clamps came loose and my nipple snapped back in place. The pain was unbearable. I sobbed terribly. She just laughed, then reattached it and tightened both clamps harder to keep my nipples imprisoned. The pain was so horrible I was crying as best I could through my bondage. My eyes pleaded for mercy - to no avail. My poor nipples had no feeling in them whatsoever, save for the incredible numbing pain they were experiencing as they stretched skyward. I had never seen nipples that erect before.

She then deposited the next round of pills with the whiskey flush. I started to struggle against the "medications" despite the formidable restraints but quickly gave up on that strategy as the slightest movement sent ripples of agonizing, burning shots of pain through my nipples and chest. She then reapplied another heat pack to my groin and left the room. Thank god the meds were beginning to take effect. Sleep would diminish the pain. I drifted off to a more worried sleep...

Again I awoke to her removing the heat pack. My nipples were on fire. I screamed a muffled scream from the pain and was truly thankful as she released them from the device. But they remained erect, more erect than I have ever seen nipples, especially my own, and throbbed with soreness. She placed some sort of suction cup device over each nipple and pumped the gadget until they were again extended, only puffier so, and slightly less painful. Only now did I focus my attention to my balls. Were they still there? Yes, but my gosh they were smaller. As was my cockie. Wait a damn minute. 'Gosh'? and 'cockie'? What the hell? Where did those words, thoughts, come from? The ring was gone, but in its place was some strange new device like a g-string panty. It held my cockie, damn it, I mean my cock, down between my creampuffs ... my what?... I mean my balls and pointed towards my tushie. Fuck! I mean my femmy hole. This is getting ridiculous...my ass! And there was some ringed opening around my anus. What was that for? Next came the usual assortment of pills and whiskey chaser, followed by the heat pack to my groin. She pulled out a clear plastic baggie with some sort of creamy looking fluid in it.

"This is some cum I froze and saved from a real man" she emphasized as she poured the still half frozen substance through the open gag in my mouth. I fought to deny its passage into my throat but again breathing and gravity would win out. She then produced a dildo of some sort and inserted it into the hole in the gag in my mouth and pushed it down into my mouth, pausing patiently as I resisted opening my throat. But as it slowly did open she slid the thing on down my gullet lodging it in the back of my throat causing a gag reflex that took my breath away. Finally I began to breath through my nose and she secured the dildo to the gag harness leaving it in place.

"That's a good gurl" she said emphasizing the word. Relax your throat dear. Soon you will truly enjoy, even crave the taste of cum and the feeling of a cock inside your mouth and throat." Then to my disbelief and dismay she produced a smallish, pretty pink dildo ('pretty'?) and rubbed some lubricant from a tube onto it, then placed it through the ring around my anus and pressed it against my asshole. I tried to protest but she just put a finger to her lips and made a "shhhh"-ing sound to me and said, "You will just love this honey." In it went. Inside me! She secured it inside me attaching it to the ring and turned it on. It hummed and vibrated with force before she turned it down to a mild vibration.

I'm ashamed to admit it but it did go in fairly easy and seemed to relieve the itching that I guess the meds had produced. And damn it, it did feel incredible. In fact I was as turned on as I had ever been. Was I hard? I have no idea since I could not see through the heat pack, nor feel my little clittie (my what?) trapped and distorted as it was in its new bondage device. But I swear I believe I came again - I think - before I drifted back off to my drug induced sleep. I dreamed of cumming all night. At least I think I was dreaming...

Yet again I awoke to her removing the heat pack. But things were different. I was so exhausted and weak. Had I cum all night? And the room was well light this time and the vibrator in my ass and the dildo in my mouth were already removed. There was an audio tape playing in the background and what little I heard before she remembered to turn it off was of some sissy sounding girl speaking in a trance like voice making sexually suggestive comments and instructions. Ah ha I thought. She was hypnotizing me as I slept. That explained a lot!

Especially the terminology my mind was using and my gaydreams. And I was shaved smooth - ultra smooth - from hairline to toe tips. Everything! My pubic hair, my legs, my underarms, even my arms, hands and feet. Gosh darn it, even between the cheeks of my tushie was silky slippery and smooth as a baby's ass. But before that could even sink in I was distracted as I recognized my balls were noticeably smaller still and my dick was a mere nub no longer visible due to the angular position of my head, and the fact it disappeared downward between my creampuffs. I had to look into the mirror to even see it. She pulled it free from the device and it popped back up into view - barely. I almost cried. It was so small. Tiny. Less than an inch I'm sure. She seemed very pleased with my shrinkage and again began to play with and tease the little nub for just a moment until it got hard, if you can call two whole inches hard.

"See, it gets hard" she laughed. "Now I want to show you something else." She slipped a vibration device on my tiny cock and turned it on. It vibrated so hard my little nubbie was numb on the outside, but driving me insane with lust on the inside. Amazing, I thought. It was so small, yet sooo sensitive. And it was extremely excited first by her touch, and now by the vibration. It twitched and stood to attention, like some proud midget. She then produced another larger pink dildo. I'm not yet skilled at guestimating these things yet, but it was a pretty healthy size. Probably 7 or 8 inches? and rather thick. Bigger and thicker than my cock had been - pre Sherry.

She placed it to my now always twitching and excited ass. With absolutely no lube this time she inserted the ribbed toy inside me, slowly, inch by glorious inch (glorious?), with a twisting back and forth motion to both make sure it went in, and that I felt it - but good. And I did. It hurt a little at first as it stretched a new path inside me, but strangely enough very soon began to feel, well, pretty darned good. She began slowly at first to fuck me with the device, but soon grew faster and faster. Always twisting so the long stubs on it slapped at my entrance every time it disappeared inside me. Damn it! Suddenly I was swimming in ecstasy. It felt...it felt awesome. I grew more excited with every stroke as they increased in speed, depth, and ferocity. Within a minute or two an amazing thing happened. I started to cum! Without my little cock even being touched it began to cum little driblets of clear cum, one after another matching her thrusts. She bellowed out her approving laughter as she withdrew the device.

"Wasn't that just darling" she said excitedly. "You came just like the little bitch you're becoming. But I have one more thing to show you." She then stripped off her clothes and stood before me totally naked. "Does seeing a naked women turn you on?" Huh, funny, it didn't. But of course I just climaxed, I told myself. But my lack of an immediate answer brought her wrath. She strapped on a harness and attached a still bigger pink dildo. It must have been 9 or 10 inches and definitely wider. I see the logic now. She is resizing my tushie with each new and larger device.

"When a woman speaks to you, you answer dog. Bitch!" she snarled, as she thrust the faux phallus in to my bottom, in one great heave, roughly, with force. She missed by a fraction with the first poke, so the dong bounced and rimmed in like a basketball shot that rattles in. It stung. No, it hurt. Pretty doggone good too. I froze in stunned pain, breathless, as if I had been struck. She then pulled it back till the tip barely popped out of my stunned manpussy, yet maintaining pressure against my sissy entrance, wanting back in. And back in it went in a slow yet unflinching, deep insertion, till it could go no further. She grinded it in one more millimeter, then pulled it back till it popped out, just barely so, again. Son of a bitch!

Er, I'm sorry, I meant gosh golly, was I fucking dying, in pain and lust at the same time. She loosened my tethers enough for me to "Turn your sissy punk ass over and show me your pussy. And raise your tushie up in the air so I can fuck you like the bitch you are!" For reasons I would only understand later I eagerly obeyed. I was drooling out my gag and mumbled something. I'm not sure what. I think I said "yes Ma'am" to some question. She pumped me in long, slow, deliberate strokes, making sure I felt the entire length with each and every stroke in, and out. All the way in. All the way out. In. Out. She threatened and taunted me, coaxing me to cum again. I was getting scared. I would never be able to...wait...ah...ah...AAAHHHH. I was cumming yet again! I couldn't believe it! I was cumming again! I had never come a second time that quickly. And again with no stimuli to my cock at all. I was dumbfounded. I simply could not believe it.

"My, my. Look at the little whore bitch cum again. Aren't you just the sissy slut. You must really like the feel of something fucking you in your ass. Don't you? ... sugar britches." Ouch. I remember calling her that. Payback is a bitch I guess. And she was winning the dick-wagging, 'we'll see who tames who' contest as well. But if this was losing, then I was snatching victory from defeat, for I was totally aroused - still - despite just creaming twice!

Then the ritual continued. The heat pack, the pills, the whiskey, the semen, the two devices for my two orifices. That drowsy feeling as I drifted off to sleep. How long was this to continue?. How long had I been here? I was starving. How many days had it been? Did I really want this to stop? To continue? I'm glad I was falling asleep. So many questions, so much to think about. Why were all these strange words and feminine terms floating around in my head? Was it the sissy audio tape training? Why did I dream of sucking some guys cock last night? Of my ass being pried apart and pumped full of cum? Of being slutted out in the open sun? And the jizz that coated my mouth and throat as it leaked and seeped down my throat actually tasted...well, rather pleasant. What...what if...zzzzzzzzz.

When I awoke next she was just finishing the removal of the heat pack. My tongue hurt terribly and seemed swollen. It felt like it filled my entire mouth, or was it the dildo? No, I could see in the mirror it was not docked to the gag and sticking in my mouth. Then I noticed my manhood area. I almost cried. My balls were tiny. My cock, well, it defies logic to even call it a cock anymore. More of a man clit now. A cute little nubbie with a tiny head. It might as well have been adorned with a tiny little dress and ribbons. And she had written something on my smooth shaven mound just above my cockie but I couldn't yet make it out through the haze I was in. It better fucking not be a tattoo. My whole body ached, and I was starving to death. I was beginning to worry about that as it attested to my length of time in this setting. I was sleeping so much I lost track of time and days. Yet it had obviously been some time because every time I awoke I was in a different device, and something new had been done to me.