Lesser of Two Evils

I bit my lip.

"I'd do anything to be yours. I'll be everything you want me to be. I'll do your filing, make your appointments, dress in sexy business attire like all the other girls, and let you bend me over your desk, and plug my ass. I'd even be your ponygirl. I've seen the porn you download, I know how much latex ponygirls turn you on."

I kissed him, and stroked his cock some more getting him hard again.

"So you're willing to do all that? To be my personal fuck fantasy in exchange for a job? Wow, Erica, way to be a cliche. You haven't been a sexy little tramp for more than 24 hours, and you're already using your pussy to get what you want. Nick was so completely right about you. He said you were born to be a slut, all you needed was the right incentive."

He was rock hard again. I put his cock in my mouth. I was going to get what I needed to survive. And David's cock was my ticket to survival.

"Oh, baby, you give such great head."

I gave his cock the royal treatment.

"Fuck my mouth. Treat me like a whore. Fuck my mouth and cum all over my face."

He grabbed my hair and fucked my mouth. He fucked me till I thought I would choke, then pulled out and came on my face. I looked up at him lovingly, wiped the cum from my face and liked my fingers clean. For added measure I cleaned his cock and drained it of any remaining cum. He collapsed back on the bed exhausted.

"So, do I have the job?"

"You have the job."

I laid next to him, and cuddled. Very pleased with myself for accomplishing my goal. being this sexy was like having a superpower. I'd always wanted superpowers.

David fell asleep, and I went to the bathroom to freshen up. I noticed that my tits were shrinking. I supposed that was why Nick put the breast forms in the purse. He knew this would happen. I stuffed them into the corners of the bra pushing the A cups I had left up and out. I was gonna need to get pumped up again soon.

I took a moment to really study myself in the mirror, I checked out my body, and what these sick fuckers had done to me. I couldn't deny that I was hot. There were worse things to be than a hot sexy woman. I liked the way I looked - it turned me on. And when allowed to cum, the sex was unreal. I had to admit that maybe Nick had done me a favor. But I hated the way it was done. I hated that I had been tattooed like a prison bitch, and being treated like a fuck doll at that party was the worst experience of my life. But I figured if this were done to me, there's no reason I couldn't return the favor, and make something horrible happen to these fucks. I'd just have to bide my time until i saw an opportunity.

The tattoo on my lower back began to itch. I tried to see what had been written back there, but it was completely covered by the corset which I couldn't get off. But I was able to see the back of my neck using my compact and the bathroom mirror. I lifted my hair and tattooed there was the number 4. WTF? Four what? What the hell was the significance of the number 4.

Out of the corner of my eye I caught movement. David came into the bathroom naked, and caressed me from behind he kissed my shoulder tenderly. Without warning he bent me over the sink, lifted my skirt and tore my panties off.

"Tell me how badly you want my cock, you slut."

I knew I couldn't hesitate or deny him anything. I played the part he wanted.

"I want your cock deep inside me, sir. Fuck my tight little ass, fill me with your cum."

He grabbed my hair and fucked me from behind, as I watched in the mirror. Watching him fuck me was so hot. I wished my balls were free so I could cum. Maybe if he fucked me harder and I focused I could cum.

"God, I love your cock. Fuck me harder!"

David fucked me violently, and I tried so hard but I couldn't cum, I was desperate to cum. I moaned passionately as I built to climax but never came. David spurted his hot load into my ass, and I collapsed unfulfilled onto the counter. Angry that I didn't cum. If women went through this as often as I was, then being a woman sucked and I wanted no part of it. I wanted these damn locks off.

I spun around and kissed David like a satisfied slut. Rubbing myself up against him like I wanted more... which I did.

"That was so hot, baby."

"Did you cum?"

"Twice, baby. You make me so hot."

David burst out laughing. He fondled the restrictor on my balls.

"You're such a liar, Erica. You can't cum with these still on. It must be torture to come so close to release and never get there. At least in prison you'd be able to enjoy being fucked."

Dammit.

"But you're putting on a good show. Nick has taught you well. So now that you can fake an orgasm, you are one step closer to thinking and feeling like a girl. But you're not getting out of these anytime soon, Erica. You have to prove your loyalty to the company, and faithfulness to me."

He held me tight, and kissed me. He stroked my hair, and held me tenderly.

"So here are my terms: You will not fuck on your own time. You will not fuck other guys. You will fuck me, and only me. I don't care how horny you get. This restrictor will drive you mad, as you will be unable to cum until I am satisfied that you have successfully transitioned to your new role. Do you understand?"

"Yes."

"Are you sure you still want to be my secretary?"

"Yes."

"Good. Pull your skirt back down, make yourself presentable. and then I'll take you to your new apartment."

I brightened.

He drove my to a very upscale apartment building downtown about three blocks from the office. He took me up to the 33rd floor to apartment 3317. He opened the door with a key, which he dropped into my purse afterward. he took me by the hand and walked me through the lavishly furnished apartment. I couldn't believe this was mine.

"This is your new home," He said, proudly.

He led me to the bedroom, there was a huge kingsized bed, and it had a definite female quality to the contemporary decor. He picked up a pair of black leather cuffs from the dresser and cuffed my hands behind my back. I was a little startled, but maybe he want to play some more. I took it in stride.

"You ready for more already?" I asked coquettishly.

"Oh, no. I'm exhausted. But your roommate on the other hand..."

Roommate? Just as I opened my mouth to ask. Emily stepped out of the master bathroom in a shiny purple bikini. I'd never seen her half naked before, her body was smokin'! Her hard, flat stomach, DD breasts, her long flowing light brown hair went so well with her green eyes, and her mouth was absolute perfection. Not pouty like mine, but an amazing curl to her lips.

"Emily is my roommate?"

"Not just your roommate. She's going to be your mentor. She'll help keep you in line, make sure you keep your promise to be faithful."

"Hello, Erica," Emily purred in her silky smooth french accent.

Emily pulled her bikini bottoms down to reveal she still had a penis, and a rather large one at that locked in a cock sleeve like mine. David walked over with a key and unlocked it. Freeing her already swelling cock. David kissed Emily deeply and fondled one of her tits.

"Congratulations on your promotion, sweetheart,' David cooed.

"Thank you, David"

Emily strutted over to me as she examined my face and hair. She unzipped my jacket and exposed my insert enhanced breasts. She turned up her nose at them. Then she caressed my ass, and I could feel her cock swelling to fullness as she gently rubbed up against me. I looked at David a bit confused.

"Come here for a moment, Emily."

She walked over to David and nuzzled up to him. David turned her so her back was to me, and lifted Emily's hair. On the back of her neck was the tattoo of the number 3 that matched my number 4.

"You see Erica, Emily, had to wait until another girl joined the program before her cock could be freed. And this beautiful cock of hers, is the only one besides mine you are allowed to touch.You remember what Ted said about how much Emeril hated being turned into Emily. Well, we figured she needed an outlet to sort out her conflicting emotions. And since you need a mentor, we thought we'd kill two birds with one really beautiful, but extremely resentful shemale stone. She'll be your mistress, now. I'll leave you ladies to it."

He leaned in and Emily wrapped herself around him and kissed him deeply... lovingly.

"Thank you for keeping your promise, David."

"Anything for you darling," David replied cupping one of her perfect breasts.

David left me there with her. Emily smiled her familiar sweet, warm smile, and stroked her massive cock. A chill went down my spine.

Her cock was huge, and still seemed to be growing. She picked up a ring gag and strapped it onto me. She strapped me into ankle cuffs, and added a spreader bar. She left me standing in the middle of the room as she went into the closet, and brought out a box of dildos, clamps, and a riding crop. She unzipped my jacket, pulled my silicon inserts out and tossed them aside. She pulled my A cup titties out of the bra, and slapped them, causing me to squirm. She stroked her 10 inch cock.

"You see Erica, I loved my life as a man. I had this beautiful cock. Women loved this cock. And these bastards caged it. Gave me this pretty face and this curvy body, making me an irresistible object for men to desire, and took away my dignity... made me a fuck toy. I hated what was done to me. I hated these men for making me like this. I still hate taking their filthy cocks in my mouth, and letting them cum in my ass, and thanking them for the pleasure of being used. But they made me a promise; that they would do the same to someone else, and that she would perfect for me, and they kept their promise. My cock will feel so good between your big beautiful soft lips, and I will enjoy shoving it in your tight little ass."

She unlocked my restrictor on my balls and the base of my cock. I'd finally be able to cum. I would have been excited to have her fuck me now that I was free. But the size of her cock terrified me.

"I remember the way I felt when I was where you are. What it is like to look in the mirror and see such a sexy body as this, and not be able to fuck it. To have your cock imprisoned and forced to take abuse from men, beg them to shove their cocks in your ass in order to cum? You see the whole time you've been eyeing me like a fuck toy, sabotaging my computer so you can look down my blouse, getting on your knees to check the power strip and trying to look up my skirt, wanting to fuck me, wanting to put your cock inside me. I've known one day, you'd be like me, and I'd be putting my cock in you."

She placed a nipple clamp on one of my nipples, I moaned in severe pain through the gag. She added one to the other nipple. I howled in pain. She took a jelly dildo and shoved it into the ring gag, keeping me quiet and forcing a gel dick into my mouth. I shook my head as she moved toward the tip of my penis with a nipple clamp. Instead she licked the tip like it was a clitoris. It sent waves of pleasure through me. She continued to tickle my clit with her tongue and suck on it. I was so aroused, but she would stop when I got close to cumming. I needed to be fucked. She stood up, removed the clamps, and placed her mouth on one of my dwindling A cups sending a thrill through my body. She was driving me mad.

"I am not allowed to torture the fucks who made me their whore, or put my cock in those men's asses. But you; who lusted after to me in this body. I am allowed to do to you what I want to do to them. You are my sex toy. The only pussy I am allowed to have. Almost a year it has been, I have a lot of catching up to do. You are mine from the time we leave the office until the time we return."

She returned the clamps to me nipples and knelt down and went back to work on the head of my cock. I twisted and moaned in a mixture of heightened arousal, pain, and fear..

She stood up, moved around behind me, and bent me over rubbing the head of her huge member against my ass. I winced at the thought if her inside me. She grabbed me by my hair to keep me from falling over, and eased her huge thick cock into my ass. My eyes grew wide. I'd not had anything this big or this thick in me. I squirmed reflexively, and started to fall forward. She yanked me back, slamming me onto her cock until I felt her pelvis against my ass. This massive thing was going to kill me. She started pumping me slowly, and I moaned intensely, which turned her on even more.

"Oh, Eric, your ass is so tight... so perfect. I'm going to love filling you with my cum. I'll train you so good. You will be the most attentive and obedient little bitch in the company."

Emily fucked me while cursing Nick and David and all the other men in the office who'd had their way with her. She fucked me with vengeance and I thought I was going to split me open. She never gave my poor ass a chance to adjust. She just pounded away like an animal. I was in tears.

She eventually pulled out, came round front, removed the jelly dildo from the gag, forced my head down, and came in my mouth, It was so much cum. I swallowed and there was still more pumping out. She slapped my face with it a few times.

I was in tears from the pain. She replaced the dildo, and stroked my hair, as she felt the head of my cock for jizz.

"You did not enjoy my cock in you. You did not cum? This is no good. This was only night you were allowed to be unlocked. You need to cum, sweetie. It will be so long before you will be allowed to cum again. Maybe next time, you cum. We try again in 10 minutes."

Without warning she snapped the 3rd nipple clamp to my penis. Intense pain shot through my body. I screamed into the gag. Emily smiled with an immense sense of satisfaction. She slapped my ass and skipped off the the kitchen. I stood there crying. I was in misery. What had I done to deserve this? Why would David and Nick do this to me? I was appalled that the girl I had thought to be the sweetest girl in the office, was this cheerfully sadistic, vengeful demon.

She returned with strawberries and champagne. She removed the dildo and the ring gag from my mouth.

"I'm sorry, Eric. We should be celebrating. Celebrating the new you. And all the things you are going to become."

She poured two glasses of champagne, and poured one into my mouth. I choked it down. She drank from hers, and fed me strawberries. She sipped her champagne and walked around me as she spoke.

"I'm sure we will become very good friends. I'm sure my cock will become your favorite, you'll look forward to our little therapy sessions. There's no reason we can't spend our nights trading beauty secrets, making each other over, and making sweet love to each other. Do you want to be my friend, Eric?"

"Yes, Mistress."

"Oh, you don't need to call me 'Mistress' this isn't your Mistress speaking this is your friend and roommate, Emily. I can make your life so wonderful. We'll share many nights of enjoying our bodies and being sexy beautiful women, but to do that you must first learn what I have learned which is what it truly means to be a woman, and how to treat your man."

She gave me more champagne to drink. And removed the clamps from my penis and nipples. I didn't trust her. It was like she was doing a one woman good cop/bad cop routine.

"I want to learn," I hesitantly replied.

"I'm sure you do. But I'll warn you. No one will give you the answers. You must discover them on your own. But we will all keep teaching you your lessons until you learn. We'll know you've learned when you stop thinking about what you should do be a woman, and just react and think like one. You can fool many people by acting, but not me, and not these men. I know because I tried. I had to embrace being Emily, embrace this spectacular body, and everything it can do and feel. I had to own it. I had to love it."

She rubbed up against me, I was thrilled to have her unbelievable body all over mine. I got incredibly turned on, as she continued.

"And I love my body. I love the way it feels. I love what it does to men and women alike. I love using it."

"But I thought you hated them... hated their cocks."

"I hate the men. I hate being fucked by men. Hate kissing their manly faces. I hate defiling this beautiful body by letting them probe it with their tongues, and their cocks, hate letting them touch it with their filthy hands....But I love the way they make me feel. I love the way they make me cum. So intense. You have felt this, no? Your ears ringing, the dizziness, the feeling of pure joy, and that need to submit to them. You've felt this?"

"Yes," I admitted.

"Yes. The clothes, the make up all make you feel sexy. But the sex... makes you feel heaven, yes?"

"Yes."

"So you ask me, if I hate them. Yes, I hate them. But I love being fucked."

She stroked my hair, and my curves. Then she pulled her spectacular tits out of her purple bikini top, and rubbed her nipples.

"But I do not want a male lover. I would love a shemale lover. A beautiful body like my own. And a beautiful cock to love. Do you see what I am saying, Eric? You are mine. But I would love to be yours. But you cannot be free until you become a woman in your mind. And so you must forgive me. Because I will put you through hell. But eventually you will learn, and then we can be together."

She lightly touched the head of my cock.

"Then you will be freed, like me. And you can have me, as Erica. We will be lovers then. Would you like that?"

"Yes, Emily. I would love to be with you like that."

She kissed me deeply and passionately. I returned the kiss. the champagne was going to me head, I was quite buzzed, and I was so turned on, I wanted to fuck her so badly.

"Do you want to fuck me? Put your cock in me?"

"Yes."

"I am so disappointed, Eric. Clearly, this will take some time."

She re-gagged me, and returned the clamps to my nipples and cock. I squirmed in pain as she lubed up her cock.

"We'll keep doing this for as long as it takes, Eric, until you learn."

What was I supposed to learn? I didn't get it... clearly. She pushed her massive dong into my ass again. Thankfully, it went in easier this time. She grabbed my hair, pulled me in tight, and whispered in my ear.

"I meant what I said, Eric. I hope you become my lover. But I'm really going to enjoy teaching you, until then."

She pounded me hard, but being the second time, she lasted longer, and I adjusted to her cock, and soon was building to orgasm. My complaints turned to moans of pleasure. I could tell she was turned on by my reaction. She sped up, and fucked me more furiously, and came in my ass a second after I came myself. I reveled in the feeling she had described earlier, the dizziness, the warmth, the desire to submit to her.

She pulled out, removed my gag and forced her cock into my mouth. I lovingly looked in her eyes, and cleaned her cock. She smiled at me. She stood me back up, removed all the clamps, and felt my cock wiping the cum off the tip, and smearing it on my face. She kissed me gently rubbing her tits against mine. It felt so good.

"I'm so glad you came, Erica. You like my cock?"

"I love your cock."

"You want more of my cock?"

"Yes, Mistress."

"Good"

She went into the closet and pulled out a sleeker version of Nick's tit pump. This one looked a bit larger, but more comfortable and had a small built in compressor. She gave me an injection in each tit. And then hooked the pump up to me.

"This will make you tits grow faster, and retain their size longer, but will make them much more sensitive to both pain and pleasure."

Then unhooked the spreader bar. She turned me around, and pushed me onto the bed. She took leather straps and strapped my ankles to my thighs. She strapped a penis gag into my mouth, and attached a chain to the bed post and the other end to my collar. She returned the restrictor to my shaft and balls.