Lesser of Two Evils

I looked back and forth between the picture on the mirror and my reflection. While not identical we could be sisters. There was no trace of me left in my face. I not only looked like a girl, but a gorgeous girl.

Nick left the room, and came back with what looked like a staple gun. Without warning he pierced my ears with little sapphire studs. The collagen was one thing, but this was different, I flinched and complained angrily through the gag. He was making permanent changes to my body. That wasn't part of our deal! I glared at him in fury. He laughed.

"Oh, sweetie, you're so sexy when you're angry."

He unstrapped me from the chair and led me by leash to the foot of the bed. He undid my cuffs for moment, and I tried to break free, but he was too strong, He re-cuffed my hands in front of me. attached a thin wire looped through an eye-hook in the ceiling to the chain between the cuffs, and snapped it tight, pulling my hands high over my head. He kept tugging till I was pulled up on to my tippy toes. He tied the wire to the bed post.

He went to the closet and pulled out a pale yellow maid's outfit, along with baby blue and white petticoats, white sheer stockings with yellow bows, and a baby blue underbust corset.

He wrapped the corset around me and fasten the metal clasps in the front. He drew the pale pink ribbons in the back tight; cinching my waist down into a sleek hourglass shape. He tied the ribbons in a pretty bow. He chuckled as he traced my new curves. He held up a large makeup mirror so I could see my shape in the vanity mirror behind me. No, no, no... From behind I was too sexy!! My long blonde hair cascading down over a sleek hourglass figure, and my now heart shaped ass was begging to be fucked. I complained through the gag. Nick just chuckled. He dropped the mirror on the bed, and rubbed his crotch against my ass. I could feel his rock hard cock through his pants. I moaned in terror.

Nick slid the stockings up my legs. This was the first moment where I realized how much trouble I was in. The stockings felt so good on my smooth legs. Nick stroked my legs as he attached the garters from the corset, and drew them taught. I began to get hard. I fought against it, and soon the sensation went away. Nick strapped pale yellow patent leather pumps to my feet, and then padlocked them in place.

He tied my leash to the bedpost again, and loosened the wire holding me on my toes. I settled down onto the heels. He pushed me up against the bedpost, and cinched the leash tight, so I only had about an inch of leash tethering my to the post. I couldn't see well enough to undo the knot, and no leverage to pull free.

He unbuckled my wrist cuffs, and slid elbow length pale yellow satin opera gloves onto my hands and up my arms. He re-cuffed my wrists behind me. And then he caressed my ass with his hands. I could only squirm as he fondled me. He took more tiny padlocks and secured the corset to me. He grabbed a pair of baby blue satin panties and pulled them up my legs. He knelt down, and tucked my cock down into them. And then he left me there for no apparent reason. I struggled to get free but it was useless.

He was gone for a while. I could hear the sissy porn on the TV in the other room start back up. It didn't make any sense. Why would he truss me up like this, and just leave me here? As I struggled my legs would rub against one another and it sent ripples of pleasure through my body. Why did it have to feel that good? The feel of the corset and the panties was also tantalizing, I hated that it all felt so sexy. And worst of all, it was making me hard. I tried not to move, but my feet were killing me in those heels, and every time I moved something I was wearing would trigger a pleasurable feeling. Maybe that was his plan. He left me here so I'd accept my fate and enjoy being dressed like this. I hated that it might be working.

After about an hour, he came back in.

"You should be just about ready, now, sweetheart. I know how sexy those clothes must make you feel by now, I'll bet you can't wait to finally be with a man."

I pleaded through the gag for him to let me go. But he didn't hear it that way.

"That's what I thought. But don't worry we're almost done."

He untied the leash and pulled me away from the bed. He unplugged the viking bra on my chest, and removed it with a slow sucking sound. I looked down to see that I had tits!! Fuck!! Were these permanent??? Nick spun me around to look in the mirror. Standing where I used to be was the girl in the picture. Nick stood next me and whispered in my ear.

"Hello, Hailey."

I struggled to get free. This was a disaster. I wasn't some trite sissy boy in a dress, I was sexy and irresistible. Nick was gonna fuck the shit out of me. He rubbed my stockinged legs, and my cock got hard. I squirmed to try and hide it, but with the sensation of the stockings and the satin panties encasing my cock, I got visibly hard in my panties. Rock hard. Nick noticed.

"Ahh, so nice to see you're as excited as I am to see your full girly self come to light, Eric. I can't tell you how happy it makes me to know how turned on you are. But we're not done yet. You'll have to wait just a bit longer, darlin'. But not to worry, you'll get what you're craving very soon."

Nick pulled the frilly petticoats up around my waist and followed it with the tight fitting pale, yellow, off-the-shoulder, scoop neck Maid's outfit. He zipped up the back, tightly encasing my tits in satin, pushing them together, as my cleavage was prominently displayed by the scoop neck. I stared at my reflection. There was no denying it. I was drop dead gorgeous. Any man who saw me would want to fuck me, instantly. I wanted to fuck the girl in the mirror. It made me even harder.

"And now to put a cherry on top of this perfect, little, slut sundae."

He applied deep candied pink lipstick to my swollen lips then dabbed a light pink powder to them in places giving them an exaggerated highlight, and finished by coating them in lip gloss. He removed the gag. I looked in the mirror. My Scarlett Johansson style lips demaned to be fucked. I stood there now with no trace of masculinity remaining at all. There was a drop dead gorgeous girl standing where there was once a boy. A terrified little girl knowing what a pervert Nick was, and what he would likely do to her.

Nick rubbed my nipples through my dress, it sent shockwaves of pleasure through my body like nothing I'd ever felt before. I gasped in shock and ecstasy. He continued to play with my tits, as he reached up my skirt and rubbed my hard cock through my panties. I felt like I'd burst and cum in my panties. Nick whispered in my ear.

"I have so much to teach you, Eric. I'll show you pleasures you've never dreamed of. But if you fail to please me. You'll will leave here exactly as you are, and am sure someone else will make good use of your sweet ass, and that irresistible mouth. Do you understand me?"

I nodded. Genuinely terrified of anyone seeing me like this. Everything about me begged to be fucked. Who would resist the urge. I felt defenseless. Knowing full well what kind of horrors might befall me being dressed like this in my neighborhood. I'd never make it from my car to the apartment door. Nick grasped my dick through the satin panties an stroked it.

"I know how turned on you are, Eric. The cock doesn't lie. You like it when I touch you. You like being a sexy girl. And I'm gonna show you what really means to be one. You will be my sissy whore for the entire weekend. By then these sexy titties of yours will have gone back to normal, and the swelling in your lips and cheeks will be less noticeable. And then I'm gonna let you leave here with the hard drives, and you can go back to being Eric. I don't think you'll want to. I think you're going to love being my sissy love toy. Before you know it, you'll be begging for my cock."

His hands roamed over my tits - driving me crazy. All I could think about was getting some release. Involuntarily, I panted like a horny slut. Nick laughed softly.

"Now nothing I've done to you is permanent. If you decide, after this weekend that you want go back to being plain old Eric, I will do everything necessary to make sure no one finds out about this. You'll be able to work from home until you feel comfortable to return. But you have to earn that right. And to do that you only need to to do two things for me. First, you need accept who you really are. Accept that this sexy little tramp you see in the mirror is the real you. And I will know that you've accepted yourself when tell me your new name. Then the second thing I need is for you to beg your master to train you to be his sissy slut. Do you want that?"

He continued to fondle my tits, and his hand stroking my cock through my panties was too much, I was engulfed in ecstasy, I hated myself, but I wanted more.

"Yes," I hissed.

"What's your name, sweetie?" He asked.

I looked at myself in the mirror. Where did I go? All I saw was the girl in the photograph. All I saw was Hailey.

"Hailey," I replied in too masculine a voice.

"You don't sound like a Hailey."

"Hailey," I gushed in my best girly voice.

"What can your master do for you, Hailey?"

"Please train me, Master."

"Train you to do what?"

"Train me to be your slut, please, Master."

What was I saying? I didn't want this, but he had made it clear that I couldn't back out now, or be kicked to the curb looking like this. I had to play his game until I could get the drives back, and these clothes off, and forget this weekend ever happened.

"I'm not convinced you really want it, Hailey."

He stopped stroking my tits and my cock, and was horrified that my first thought was that I I'd die without his touch on me. I needed to cum so bad, and I needed this to be over, and the quickest way was to just get on with it. I needed to convince him, so I got on my knees, and begged.

"Please Master, make me your slut, train me to please you."

"You want my cock? You want me to train you to fuck and suck like the whore you've always dreamed of being?"

"Yes, Master. Please train me."

Nick smiled. Pulled his cock from his pants and shoved it in my mouth. He grabbed me by my hair and fucked my mouth. Within 30 seconds he came down my throat without warning. I swallowed reflexively. He pulled his cock out and rubbed it on my face.

"That taste good slut?"

"Yes, Master."

It didn't but I needed to just get through this, so I played along.

"That's what I thought. You love cum, don't you Hailey?"

"Yes, Master," I murmurred embarrassed as hell to have just taken his cock and swallowed his load.

He smiled, put his cock away, zipped up, and motioned for me to stand. I complied, and he led me by my leash to the living room. He un-cuffed my hands, and unhooked my leash. He bent me over the sofa, and felt me up. My body was alive with ecstasy from his touch. I wished he'd touch my cock, if only he would I could probably cum, and this growing desire to be his slut would go away. I couldn't think straight. I was alive at his touch and the feel of his hands caressing me through these clothes. I wanted to cum so bad, but more than anything, I badly wanted this all to go away. He ground my ass from behind as I felt his cock grow hard again. "Oh, god. This is it. He's gonna fuck me." I cringed in fear. But he stopped.

He hooked a finger through the ring on my collar, and led me around to the sofa, and sat down. He patted his leg. I cautiously sat on his lap, and he continued to feel me up. It was driving me mad, I moaned with pleasure. He seized the opportunity and shoved his tongue into my open mouth, and kissed me deeply. I had never kissed a man before, it was rough, and gross. I tried to pull away, but he grabbed my hair and held me there. As his hands groped me everywhere, and I felt the sweet caress of the satin I was encased in, I continued to moan involuntarily. If anyone had walked in on us, it would look to them like I was making out with Nick, begging to be fucked.

He pushed me off his lap and onto the sofa next to him, and undid his pants. His massive cock sprang out. He wagged it at me, and smiled. He picked up the remote and rewound the sissy slut video to a blow job scene. He stroked his cock as he watched.

"Watch and learn, Hailey."

I watched the pretty sissy slut on the video make love to her master's cock with her mouth. It was so hot. It was turning me on even more.

"Now, show me what you've learned, Hailey. Make love to my cock."

He stroked my titties through the yellow satin dress, It drove me insane. I sucked his cock like a hungry slut. Making love to it like the sissy slave in the video. He moaned with pleasure, but didn't cum as quickly as he did the first time. He soon stopped being passive, as he grabbed my hair and fucked my mouth almost choking me. I made involuntary quacking noises which turned him on even more. He clenched, and held my head in place as he blasted a massive load into my mouth. I forced myself not to swallow this time. He let go of my hair.

"Show me what you have there, slut."

I sat back, and opened my mouth so he could see his hot load still resting on my tongue.

"Good girl. Now, swallow that tasty treat. You've earned it."

I reluctantly did as commanded, and swallowed his bitter jizz. He pushed me back on the the sofa and crawled on top of me. Me ran his hand up and down my stockinged legs. He switched to my tits, and then back to my legs. The sensation was driving me insane. I was rock hard, aching badly for release. I needed to cum so bad, I blurted out.

"I need to cum, master. Please make me cum."

"You want to be fucked, Hailey? You need a man's cock deep inside you?"

The thought of it turned my stomach, but I knew it was coming whether I like it or not, so I played along.

"Yes, Master."

"It doesn't sound like you really want it."

He looked over at the TV. On the video the sissy slut was begging to be fucked, begging for a cock deep inside her. She was desperate for cock. Nick looked from the TV back to me, and stroked my legs, and grinned knowingly. I knew what he wanted to hear.

"Put your cock deep inside me, make me cum like the little whore I am."

He grabbed my ankles and pushed them over my head, reached into my petticoats and pulled my panties off, freeing my stiff cock.

"You're clitty is so hard, Hailey. Your master really turns you on, doesn't he."

"Yes," I replied sheepishly.

And then he wet his index finger with his mouth, and slid it into my asshole. I was surprised that the sensation was not unpleasant. He slowly finger fucked me, adding a 2nd finger and then another as he went on widening my tight little hole. He slowly fucked my ass with one hand while massaging one of my tits with the other. The combination was extraordinary. I threw my head back and moaned like a slut. Nick laughed.

"Does my little slut need her sissy pussy fucked?"

If being fucked felt anything like this, then yes, I wanted to be fucked. I wanted to be fucked hard.

"Yes, Master. Please fuck me. Fuck my tight sissy ass."

My moaning had Nick rock hard again. He pulled a small bottle of lube out of a drawer in the coffee table. He pushed some of it into me with his fingers. I played with my own tits, loving the sensation of the satin gloves rubbing the tight satin encasing my pumped up titties. I had never before imagined anything ever feeling like this.

Nick smiled at me, as I played with my tits: my ankles over my head, my corseted girly ass in the appropriate position to be taken. He grinned as he coated his thick 8" monster with lube, and rubbed it up against my now amply loosened opening. But I was unprepared for his full manhood.

He slid it into me slowly. It filled me up, I gasped from the slight pain, and the feeling of his massive cock inside me. I reached up and grabbed his shoulders reflexively. His smile widened at my apparent ecstasy at having him inside me. I had a man's cock inside me and I wasn't complaining. What was wrong with me?

He slowly pumped my ass, as I adjusted to his size, then he sped up, gradually. The sensation changed from one of humiliation to one of mind blowing ecstasy. I never imagined anything could feel this unbelievably good. Oh, god, I was getting into it. I was now a willing partner in this sick fantasy. I was loving being fucked like a slut.

Nick grabbed my ankles and really leaned into it. I couldn't contain myself. I came. My load squirting up onto my face. Nick slowed for a moment, wiped my cum off my face with his fingers and fed it to me. Lost in lust I eagerly lapped it up. I looked into his eyes lustfully. Wrapped my arms around his neck, as he sprinted for home. He grunted and groaned as I felt his hot load pump into me. I was dizzy and drunk on sex. I clung to him like a child. He collapsed on top of me; still convulsing. I was in heaven. I had never felt anything like this in my life.

As the elation slowly began to wear off, I became painfully aware that I was a young man dressed like a slutty maid, I had just swallowed two loads of a man's cum, and one of my own, and a 4th was stirring inside my ass. And rather than screaming indignantly as I should be, I had my arms wrapped around him, and as I started to let go, Nick kissed me deeply. My lips parted and accepted the kiss, instead of letting go, I gave into him, and kissed him back.

"Thank you, Eric" he whispered, "Thank you for granting me this. You were everything I hoped you'd would be."

He got off me. Tossed me my panties. And walked off. I sat there a moment confused - the cool air on my balls made me feel a bit exposed, so I slid the panties back on, and tucked my now flaccid thing down into them. Nick came back with two glasses of Jameson. He handed me one. After what I'd just been through I needed it. I knocked it back and set the empty glass on the coffee table. Nick sat next to me.

"That wasn't so bad now was it?"

I was stunned. But no it wasn't as bad as I imagined it would be. I had never cum like that before in my life. Not with a girl, not masturbating. Never. I wasn't going to admit it to him, but it was most intense orgasm I had ever had. I just sat there silent - in shock. I was having a hard time processing everything. Nick took a sip of his whiskey, and then touched my cheek softly.

"You look very pretty, you know. Prettier than any girl at the office."

What the fuck was he doing? Was this some sort of additional mind game?

"Thanks", I said bashfully. Was it over, Was he gonna make me stay the weekend, or could I get out of these clothes, wash up and leave?

"You're free to go, now, Eric. you don't have to be Hailey for me anymore. You fulfilled your end of the deal. I just want you to know, that you're the sexiest girl I've ever been with. And the best fuck I've ever had. I know it's probably too much to ask of you, but I'd love for this not to be our last time together."

Was he out of his mind? No way I was doing this again. He leaned over and gently kissed me on the lips. then he hung his head, and motioned to his bedroom.

"You can go get undressed now."

I quickly got up, and tried to walk as dignified as I could in those heels and got the fuck out of there before he changed his mind. I went into his room and closed the door, leaned back against it, and had a mini panic attack. What the fuck had I just done? I just let a man dress me up like a slutty maid and fuck the shit out of me. And I enjoyed it! I hated myself. I reached back and unzipped the dress. I let it fall to the floor and I stepped out of it. I pulled the petticoats off as well.

As I tried to undo the garters I caught my reflection in the mirror. I walked over and stood there in awe. The girl in the mirror was maybe the sexiest thing I'd ever seen. My tits which were probably a full B - perfect and perky. I reached up, and massaged them with my satin gloved hands. What was I going to do about these? I was sure they'd probably go away on their own like Nick said, but when? I doubted even putting my clothes back on taking out the extensions, and removing the make-up would make me any less girly. I sat down at the vanity and sighed. I couldn't stop marveling at how hot I was. I'd never been with a girl as hot as the one I was staring at. And my tits... I couldn't stop playing with them. I was getting hard again.