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This is a story inspired by Virgil_Assad’s Crime Doesn’t Pay, and is a forced feminization story told from the male dominant’s point of view.

My thanks to Maddirose for her helpful edit.


I jimmied open the window without leaving a single scratch, took a deep breath of the balmy LA night air and made my way silently inside. I had watched my target the entire day and knew he had gone to bed upstairs an hour ago, and his bedroom had been dark for 20 minutes. I pulled out my needle kit and readied the sedative and checked my silenced pistol one last time. I prefer to kill with as little pain or mess as possible, so my method is to put my victims under with the sedative and then suffocate them before disposing of the body without a trace. The gun is just in case of complications. I had cased the place for three days and this was the first night the target was alone in the house; he had been with his fiancée the nights before but they had had a big fight and broke up with her earlier in the day.

She was the entire reason he had to die; he was an accountant for a Japanese crime syndicate and she was a gold digger who targeted him and convinced him to start skimming, to provide for her extravagant lifestyle. He’s 26 and a shy math-wiz, and made a perfect target for her, much younger and more attractive than the producers and execs she normally went after. The fiancée, Amber, was a curvy blonde with a pixie-cut, really hot and kind of slutty, totally out of his league. From what I heard on the bug I planted, she had wanted him to transfer almost all of the money to her account instead of him paying for everything she wanted, like he did at the time. He had finally caught on to the fact that she was just using him until she had what she wanted and would leave him to find some other poor sap, so he grew a spine and dumped her.

I’m not Japanese myself; I’m just a contract killer they bring in when they need someone without connections to the syndicate, as in this case when the target is the bastard son of one of the bosses. I used to be in the army, but during my fourth tour a frag grenade exploded behind me, leaving my back riddled with shrapnel. After a series of surgeries in the military hospital in Germany I was fully recovered, but I had had enough and was honorably discharged with a purple heart and a bronze star. Back in the states, I got a degree in pharmaceuticals and got hired as a travelling sales rep, but that was just my cover. You see, just after I got home I visited an old army buddy in San Francisco, and after a night of heavy drinking he confessed what his new line of work was; killing for money. Instead of being horrified I asked him what it paid, and when he told me I asked where I could sign up. That was eight years ago and I’m now 35, living in Sausalito, just north of the Golden Gate.

I made my way up the stairs and into the bedroom. To my surprise the target was sleeping naked on his stomach; the covers had slipped off so they only covered his legs and, damn, he had a really round, girly ass, and a slender body. I felt my cock stir unexpectedly in my pants, I’ve never felt any attraction to a guy before, but I was a definite ass man, and this was one of the finest I’ve ever seen. I bent down and took a closer look at his face, I had studied it before of course to make sure I had the right guy, but that was clinical. Now I saw it for what it was; a soft, almost effeminate face, even for a Japanese man, but maybe that was because his mother was Brazilian. I found myself thinking that with a bit of makeup he would be very passable, even pretty. Why the fuck was I thinking like this? I should just inject him and be done with it. But then he made a little sound in his sleep and arched his back and shimmied with his hips, I guess he had a hot dream and needed to rearrange himself, and it looked so hot I almost moaned out loud.

Fuck it. I put my needle away and hunched down so I was face to face with him and shook his shoulder to wake him up as I lit the bedside lamp. He groaned and opened his eyes and when he saw me he took a deep breath to scream, but I shook my head and shushed him. He had really big, dark almond-shaped eyes, very pretty. I quietly said, “My code name is Mister Gray, do you know who I am?” He nodded. “Do you know the reason why I’m here?”

“You…” he cleared his throat, “You are here to kill me because I stole from the bosses.” A single tear rolled down his smooth cheek.

“I’m here to recover what I can of the 2.7 mil you stole and make you disappear for good. I might be convinced to spare your life though, if you do everything I tell you to do.” I removed my glove, wiped his tear with my finger and then ran it gently down his spine to his ass which I cupped, leaving little doubt as to what I wanted him for. His skin was soft and smooth under my hand and his ass filled my hand just right.

His eyes got even bigger, if that was possible, and I could see a wide range of emotions playing over his face. He opened his mouth to give a quick reply, my guess would be an outraged NO, but he closed his mouth porno again and seemed to consider it. No doubt he knew my reputation, I always made my target disappear, no matter how well protected or powerful they were, and he must have known he didn’t stand a chance in a physical confrontation. In a small voice he asked, “What would I have to do?”

“As I said, anything I tell you to do, starting with standing up and showing me your body.”

He blushed furiously but nodded and stood up before me, his hands trying to cover up his nakedness and his eyes downcast but glancing up at me once in a while.

“Don’t be shy, hands by your sides and straighten your back.” I turned on the overhead light and looked him over. His body was mostly hairless, and he was slender, with wide hips for a man, and a smallish cock hanging half-limp between his thighs. His skin was a golden tan with very few blemishes, just a few small moles.

“Turn around, place your hands on the nightstand and arch your back for me, show me your pretty butt.” He opened his mouth a few times to protest but then thought better of it and did as he was told and put his wonderful ass on display for me. It was turning me on like crazy, ordering this effeminate man around, and as I looked at his ass and adjusted my rock hard cock in my pants I decided I needed to take this much further. I looked around the room and saw the two bureaus standing opposite the bed. I told him to keep his position and walked over and opened a drawer in each. The left one was obviously his ex-fiancée’s and I quickly rifled through it. I returned to him and told him, “Put these on,” and handed him a pair of white hipster panties, a silky, lacy cream colored top and a tube of pale pink lipstick.

“What the… How far are you going to take this?” he asked, finally daring to speak up.

“I won’t do anything that will hurt you, but we will be spending the night here, with you being compliant and open minded, or else you will feel a needle prick, go to sleep and never wake up. Now put on the clothes and lipstick.”

“OK, I’ll do it. Please don’t use the needle, I know I was unbelievably stupid when I stole from the Yakuza, but I don’t wanna die because of it.”

I nodded and watched him expectantly. He put the things down on the nightstand started with the panties, bending over and pulling them up with his back to me. The way he shimmied his hips as he pulled the tight garment over his hips and how the white panties hugged his ass brought out the shape even more was really hot. He pulled on the top next; it was slightly loose around his body and stopped about two inches above the panties, showing a little bit of skin. He walked over to the mirror and applied the lipstick, and then came and stood in front of me.

“Wow, you make a pretty girl! Such a pretty girl should have a pretty name, don’t you think? How about Naomi? Doesn’t that mean true beauty in Japanese?”

“Yes, sort of, I like it. Um, thank you Mister Gray, for calling me pretty.”

“You’re welcome Naomi, and you can call me David, Mister Gray is just an alias. Now that you look like a girl I think you should speak like one to, don’t you agree?”

He swallowed nervously and after a bit of hesitation he answered, in a brighter voice, “Yes David, I’ll try my best.” It wasn’t really convincing, but such a turn-on nonetheless.

“I’ve always liked taking pictures, and you make such a pretty subject, so why don’t you pose for me?” I asked and fished my camera, a Sony RX1, out of my pocket.

“You want to photo me like this!? What if somebody I know sees the pictures?”

“It would be just for me, and anyway, you can never see any of your friends again, you are supposed to be dead, remember? Now take the same pose as before but look back at me over your shoulder, Naomi.”

I could see the hesitation playing over his face but then he let out a little sigh, and seemed to resign himself to his fate. He stood with his feet shoulders width apart, rested his hands on the nightstand and looked at me and asked, “Like this?”

“Almost, arch your back a bit more, stand on your toes, and pout your pretty pink lips a bit,” click, click, “Oh, that is perfect, you look really sexy, now give me a smile, good,” snap, click. We went through pose after pose, and I was really enjoying myself, and I think he was too, the bulge in his panties became more noticeable as he continued showing his body for me and his smile seemed much less fake than in the beginning. I got more hands on as we progressed, his body was just so tempting and it was easier to get him into the poses that I wanted. When he was kneeling on the bed with his ass in the air I couldn’t resist and grabbed a cheek with each hand and squeezed and massaged, and Naomi moaned and pushed back.

“You like this, don’t you?” I asked, my hands still on him.

“Umm, yeah, it feels nice.” He turned red in embarrassment.

I walked around the bed so I was in front of him and said, “It’s really turning me on too, and I want you to help me with that. Do you want to?” I asked as I opened anime porno my belt and unzipped my trousers. I pulled my cock out of my boxers and stroked it slowly, as Naomi looked on, wide-eyed.

“Uh, I don’t know, I’m not, I…” he stammered, but he still couldn’t take his eyes of my dick, and he still used his feminine voice, now breathy and hot.

“I think you do want it, I think you like being dressed like this, to submit control like this, to feel beautiful. I don’t want to rape you, or force you, so if you refuse we can continue to play dress up for a few hours, then you will transfer all of the money that is left to the Yakuza and go into hiding, trying your luck somewhere else.” I caressed his cheek down to his jaw and lifted his face so that he was looking into my eyes. I rubbed my thumb gently along his lower lip, and continued, “Or you can say yes; you’ll still have to give back the money and leave the city, but I’ll let you keep five grand as a thank you, and you will have broadened both of our horizons.”

I looked into Naomi’s eyes and saw the emotions coursing through him, and then he looked down at my cock again and leaned forward and took the head into his mouth and I had my answer. That soft, pretty mouth wrapped around my fat cockhead felt incredible, the strong suction and the way his tongue rubbed against that sensitive spot just below the opening, it made my knees go weak. I wanted to grab hold of his head and just thrust until I came, but I knew it was important to let him explore on his own. I’m pretty happy with my dick, it’s about seven inches but pretty thick, and the head is really big, and some girls have had some trouble with it. Tonight, because I had been hard for so long and the situation was so fucking hot, my cock was even fatter than normal and Naomi was gagging a bit when it nudged the back of his throat.

“That feels so good Naomi, just take it easy and take as much as you want, you can stroke the rest with your hand. You look so fucking sexy with those big eyes looking up at me and those pretty pink lips wrapped around my shaft.”

I ran my hand along his neck as his head bobbed up and down, continued down along his sides to his waist, and he felt just like a woman under my hands. I slid my hands back up along his front and found his nipples under the silky material and started playing with them. This made Naomi moan around my cock and start sucking even more intensely, the head of my cock bumping against the back of his throat on each down stroke. I hadn’t cummed for three days before this, so I felt confident I could get it up again later, and decided to stop holding back.

“Naomi, I can’t hold back any more, I’m gonna cum. Oh, fuck! I’m gonna cum right in your mouth, would you like that?” Naomi nodded and made a muffled moan, and I asked, “Are you gonna be a good girl and swallow my, mmmh, thick load?” He nodded vigorously and gave the spot just under the opening a flickering lick and I felt my balls draw up against my body. I gave a loud groan and came hard as wrapped my fingers in his hair, pumping my thick seed again and again into his welcoming mouth. I had never ever cummed so hard from a blowjob before, it just went on and on, Naomi just sucked and swallowed until it felt like my balls were completely drained, until the pleasure almost turned painful and I had to pull out.

I was breathing hard as I looked down at Naomi and he smiled up at me and licked a fleck of white from the corner of his mouth sexily. I pulled him up to me and to both of our surprise, started kissing him passionately as my hands roamed his body. As one hand wound up on his wonderful ass, the other snaked down into his white panties as I decided that I wanted to repay him for the pleasure he gave me. I started rubbing my hand up and down the underside of his shaft, not really jerking him; it was more like I was rubbing his pussy, his clit, as I kissed his girly lips and massaged his round ass.

He was moaning into my mouth as he kissed me hungrily, and then my finger found its way into his crack and rubbed against his tight opening. Naomi shuddered and gasped as he came into my hand, his arms clutching around my neck to keep upright. I gave him a kiss on his long neck and then held up my cum-filled hand and said, “Good girls should clean up their messes, don’t you think?” Naomi nodded and started licking and slurping up the pearly liquid, sucking each of my fingers clean. Suddenly, I could see Naomi realize what he was doing; his eyes widened and a blush crept over his cheeks, and then he said, “That was, um, intense. What now?”

“Well, I think we’ll start with taking care of business, let’s go to your computer and arrange the transfers, and then we can explore your ex’s closet a bit more.”

The transfer went smoothly, and afterwards I closed all his accounts, destroyed all of his identification, his bank cards, everything that could leave a paper trail, and Naomi helped me. He understood that even though I had decided to spare his life, the Yakuza hadn’t, and he could never ever go back to his old arap porno life, they were so powerful and far reaching that he would never be safe if he did.

Afterwards, he showed me to his ex’s closet, and it was like hitting the jackpot. There were so many different outfits, some formal, some girly, some sexy and some downright slutty. There was even a long, wavy brunette wig. Naomi explained that his ex used it when she went to auditions sometimes, being a budding actress and all, and I knew Naomi would be wearing it soon.

“Naomi, I want to take more pictures of you, but you are a bit too hairy to look completely feminine, so I want you to go into the bathroom and get rid of all your body hair. I’m sure Amber has some hair remover or something like that you can use, and use her soaps and lotion and perfume, I want you smelling like a real girl.”

“Okay, I’ll do my best. What else are you going to do to me, David?” He sounded nervous, and I could guess why; he was afraid of losing his second virginity.

“I don’t know, baby. I’m playing this by ear; I’ll find something in here for you to wear, then we’ll take some pictures and when we get too hot we’ll do something to remedy that.” I wanted to leave him with some hope that he would make it through this night with his ass intact, I wanted to build it up until he wanted it himself, until he asked for it.

He nodded and with a strange little smile he went into the bathroom. I started looking through the clothes and things and after maybe 15 minutes I had put together an outfit I would love to tear off a lover. I have never really gotten the whole schoolgirl thing, or the overly slutty look, my thing was always unattainable women, and for someone like me, who grew up poor but close to wealth, a high class beauty was the ultimate in sexy. I found a slinky, expensive-looking dark red dress, a black bustier with attached garters, black thong panties, and sheer black stockings. I found a pair of heels to match the dress, but had little hope that they would fit as they looked petite.

I carried the clothes into the bathroom, there was a faint chemical smell in the air from the hair remover, mixed with the more pleasant scents coming from the shower. I placed the clothes along with the wig on the vanity in the bathroom and called to Naomi, “Put on what you find out here and come join me in the living room, okay?”

“Sure, David, anything you want.”


I was blown away by how beautiful she looked when she walked through the door to the living room. I was sitting on the couch with some music on, drinking a scotch, my shoulder holster and jacket hanging over a nearby chair. I knew it was careless to be unarmed, but I wanted Naomi to feel comfortable, and strangely I trusted him. I was thinking that it was taking a very long time, but when she entered it was definitely worth it. It was very hard to see anything other than a lady, and I decided I would treat her like one.

Naomi had not only put on the clothes and wig, but had taken time to put on makeup as well. It wasn’t flawless, but good for a first attempt; not garish or slutty, and to me it looked perfect. I just sat looking at her with a stupid grin on my face, and Naomi smiled back at me, and then did a slow spin. The dress was knee length, had very little in the way of cleavage, but the cups of the bustier created the illusion of breasts underneath. The dress plunged down in the back instead, showing of her shoulders, and managed to be both clingy and flowing at the same time. The heels were on her feet, to my surprise, and they made her legs in their shiny stockings look curvier, and gave a perfect lift to her ass. When she faced me again she asked, “I take it you like it?”

“You look… Goddamn, you’re beautiful!”

Naomi smiled and blushed and said, “Thank you! I feel, I don’t know, different, attractive, the way you are looking at me makes me feel wanted in a way I’ve never felt, and the clothes feel so good against my bare skin.”

“Well, you are very desirable, I don’t think I’ve ever felt a stronger attraction to a girl. Would my lady like something to drink before her photo-shoot?”

“Oh, that would be nice, sir. Some red wine would be great. There is a $1000 bottle in the wine fridge I was saving for mine and Amber’s anniversary, but now we can use it to celebrate the end of the old me.”

I agreed, knocked back the last of the Laphroaig, savoring the burn and the intense smokiness, and went to fetch the wine and two glasses. I looked over the 20 or so bottles and called out, “Which one is it?”

“It’s the Château Margaux ’05, white label with gold writing.” The way she said the name of the wine, with a perfect French accent, was really sexy, and I hoped she could really speak French, that language is such a turn-on. I uncorked the bottle, poured two crystal wine tumblers, and headed back to the living room. When I handed her one of the tumblers I noticed that she had painted her nails a deep red to match the dress, which I thought was a nice touch. Naomi thanked me, and we said cheers and clinked our glasses together, and drank. Naomi drank down her entire glass in one long swallow, and when she brought the glass down from her full lips I refilled it without asking. She took another long swallow, and then asked, “So, how do you want me?”

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