Lesser of Two Evils

I pulled my cock out and stroked it with one gloved hand while I played with my tits with the other. I was getting so close but I couldn't climax. It was probably because I had already cum so massively by being fucked, all this stimulation wasn't enough to get me off a 2nd time. And then I heard Nick open the door...

"I forgot to give you the key..."

Nick came in with the key for the padlocks, and caught me masturbating. I tried to cover up, embarrassed. He chuckled.

"Something turning you on, Eric?"

"No, I.... I..."

"I thought for sure you'd be ripping these clothes off, and instead you're getting off on your sissy self," he said smugly.

He approached me, calmly.

"Do you need a hand? Or, maybe a cock?"

"No... I... I don't know what I was..."

Nick ran his hands along the sides of my corset, and across my exposed tits, he leaned down and kissed me fully on the mouth. I pulled away embarrassed. Nick rubbed my back warmly.

"It's okay to want it, Eric. I could tell how much you liked being fucked. You Let me help you out.. make you feel like a woman again. That's what you really want isn't it, to feel the way you felt with your arms wrapped around me lost in ecstasy."

I hated myself, but I wanted him again... badly. I wanted him to fuck me... make me feel like I felt before. I stood up, and kissed him back and stroked his cock through his pants.

"I want you Nick. I want your cock."

For a split second Nick's prediction of me begging for his cock flashed through my head. But I told myself. It just be this once. I'll get it out of my system.

Nick picked me up, and carried me to the bed as I wrapped my arms around his neck. He laid me on the bed, and crawled on top of me. He kissed me deeply. I couldn't help myself, I kissed him back passionately, and swooned with the anticipation of his cock in my mouth. He pulled my panties off, and fondled my cock. He reached down and put it in his mouth. His tongue on my cock got me so hot. I arched my back in ecstasy.

I pushed him away, turned the tables, and crawled on top. I undid his pants and took out his cock. I lubed him up with my mouth while looking him in the eye, watching how turned on he got. Then I straddled him, and lowered myself onto his cock. I rode his cock, driving it deep into me, while stroking my tits with those wonderful satin gloves. He grabbed my waist and drove himself into me with every bounce, as I fucked myself toward ecstasy. It took much longer than the first time to get off, but I came so much harder. So hard I nearly passed out as I collapsed onto his chest.

But he wasn't done, he flipped me onto my knees, and entered me from behind. I was now facing the mirror on the vanity watching him fuck me doggy style. It was the hottest thing I'd ever witnessed. There was this hot, blonde sexy slut, being pounded from behind and I could feel every stroke. It was heaven, I moaned and bucked with pleasure as I watched him fuck me. He grabbed my hair and rode me like a pony. I felt myself building toward orgasm again, and hoped the spurt of his hot cum into my ass would be delayed long enough so that I could cum again. My hopes came to fruition as I screamed a ragged womanly orgasmic scream, as I came so hard my dick hurt. Nick pulled out, turned me around, and shot his load all over my face. As I knelt before him, his hot man juice dripping down my face my mind went blank. I couldn't think anything except, that I loved being his slut. He slapped my lips with his softening cock. And then laid back in bed.

He patted the pillow next to him. I had no will to resist. I lay down next to him. He wiped the cum from my face with his hands and plopped his fingers into my mouth. I playfully licked them clean. What was I doing? I couldn't tell up from down. What the hell was I doing? I had never even fantasized about being with a man before, and now here I was gazing adoringly at a man, reveling in the warmth of the multiple orgasms he just gave me, and the taste of his cum on my tongue.

"You are a heavenly angel, Eric."

"You mean, Hailey?"

"So you've accepted it?"

"For you, Nick, I'll always be Hailey when you need me to be."

I was out of my mind for saying it. but I got lost in the moment. He had awakened something amazing in me I didn't know was there. He wasn't such a bad guy, and I really didn't mind being his lover. It was keeping me out of prison. I didn't want to be a girl full time or anything. But being Nick's secret sissy fuck toy might not be such a bad thing. I didn't know how I'd reconcile my lips and cheeks, but I'd worry about all that later. I wanted to enjoy this. I rested my head on his chest and cuddled.

"I love being your girl."

"So, you're in no hurry to go back to being Eric?"

"No. Being Hailey's not so bad. The sex is amazing. And you made me look so sexy. I love the way I look."

"So you want to stay like this the whole weekend?"

"Sure. But then you have to do what you said, and let me go back to being Eric. I like this but I'm not ready to be a girl all the time."

"Are you sure? Cuz I'd love for you to be Hailey at work too."

I mused at the thought of being a girl at work. But being a slutty maid was one thing, I wasn't sure I could pull off a passable girl in daylight.

"Think of it. You could become my secretary, and we could have sex in my office while we scheme about how to take over, and then come home and celebrate our victories. I'll buy you all kinds of sexy outfits. It'd be awesome."

"You've gotta slow down, Nick. I'm still adjusting to this. I'm just not ready for that kind of a commitment. Let's just take it slow and move forward with our plans to take over the company."

He looked very disappointed. His absently played with the bows at the tops of my stockings, and stroked my side through the corset gently.

"Well, I'm not sure that's going to work with you as Eric."

He reached into his pants and handed me a folded pink slip of paper. I unfolded it to find a termination notice.

"Because you're fired."

"What?"

"After you left, I told David everything, and showed him the evidence. You weren't there to defend yourself, so he decided not to give you a chance to cover your tracks, so he fired you, and suspended all of your access codes and your badge. When I told him you tried to blackmail me, he left it up to me whether or not to press charges. So whether, or not, your sweet ass goes to prison is entirely up to me. And going to prison with those lips... well..."

I was completely stunned, speechless. Everything I had just done was pointless. I had no job, and was facing a prison term at this asshole's whim.

"I think you'll do very well in prison, Eric. You clearly love being a sissy bitch. And those plump, sexy lips will drive those cons crazy. You'll be like candy to them, passed around like a sex toy from cock to cock."

I was terrified.

"Nick. Please."

"Wait, I haven't even gotten to the best part, yet."

He opened his laptop, and showed me his video feeds. There were hidden cameras all over the house. He played back certain moments of me getting fucked and loving it, especially the parts in the bedroom, and my masturbating.

"I could edit this all together and make it look like you made yourself my bitch voluntarily. You certainly were not forced when you were begging to be fucked, or riding my cock. once this goes up on shemaletube you'll be instant bitch meat."

"How could you? I'm gave you everything you needed to get what you want."

"Oh, not everything. Not yet. You see, trying to blackmail me, really pissed me off. Nobody fucks with me without becoming my bitch. In your case it's more literal than figurative."

I started crying. This fucker had ruined my life. I couldn't even argue. I had no leverage whatsoever. I hung my head.

"Fine Nick. I'll be Hailey for you at work. Just please don't send me to prison."

"It's not that simple, anymore, Eric. You're not getting off easy anymore. You had your chance to be my partner in this, but now that's off the table. Since I can't trust you, you have prove that you've completely accepted your new life as Hailey. You need to commit to becoming a girl, hormones, surgery, the whole deal. You need to accept that Eric was a lie, a sissy boy masquerading a straight man. You need to destroy everything in you that is Eric, and embrace the naughty little cum princess that is the real you."

"Hormones? Surgery? There's no coming back from that!"

"You don't have to do it, Eric. You can go home now, if ya like. Just as you are. Or you can take this new offer on the table. Sweet sexy, Hailey has a future as my secretary. Sissy boy Eric's future is uncertain except for the 12 years in prison. And the internet video of him dressing like a slut and joyfully taking a man's cock that will likely haunt him all his life. I'll of course blur my face out, for privacy."

"Nick, please."

"Eric. I think you know how badly I want to make you my bitch.I don't like to lose. I'll do anything to own your ass. The way I see it; you either commit to Hailey, or to Eric. I'd prefer Hailey."

I was crying. My life as Eric Wilkes was over. I supposed being a secretary wasn't so bad, Emily, Heather and Krystal seemed to love it. I'd have a life, I'd be free, and I'd get to have amazing sex even at work. I sighed in resignation.

"Fine, I'll be Hailey for you."

"You don't sound very committed. I need you to prove to me that you want to be a girl. That you're prepared to go all the way."

"How do I prove it to you?"

"For starters I need you put this on."

He handed me a metal tube, a cock restraint, along with a tiny padlock.

"Enslave your own cock. Lock Eric away. Make it so the only areas you can receive pleasure are your tight little girly ass, and your sweet, sexy girly mouth."

I took the tube and considered that ramifications of it. I looked at Nick hoping that any moment he'd tell me that he was just pulling my leg. That this was just his way of having a joke at my expense. That look never came. Nick glared at me sternly. I sighed sadly, and slipped the tube over my cock so only the head was exposed. I looked up at Nick who smiled devilishly. I closed my eyes, as I clicked the padlock closed.

"Good girl, Hailey. Now put your panties back on"

I pulled the baby blue satin undies up, and watched as Nick tucked my shackled penis down into them so the head would sit where a girl's pussy would be. He tickled the head through my panties. making me moan.

"Oh, you're such a little slut, aren't you, Hailey."

"Yes, master."

"Good, now pick up your petticoats and your dress, and put them in the hamper."

I did as I was commanded. Nick went into the closet and pulled out a shiny pale yellow patent leather motorcycle jacket and matching mini skirt. He tossed them on the bed.

"Get dressed."

I slipped on the skirt, and zipped it up. It hugged my amazing ass so deliciously. I pulled on the jacket which was snug, and zipped it up which created some nice rounded cleavage. The inner lining of the jacket felt amazing on my bare tits. He dropped two yellow wrist length PVC gloves onto the bed, so I swapped out the satin ones for these. I was one hot slut. I started to get turned on. But the cock sleeve resisted painfully. I could already see how this was going to be a problem.

Nick sat me down at the Vanity and fixed my hair, and make up.

"I will teach you to do your own make-up, as we go, but for now I'll just do it for you. Try to pick up as much as you can by watching."

When he was done, I was so sexy and slutty. My pouty lips, covered in pink gloss were begging to fucked. My cock hurt. I winced from the pain. Nick noticed this.

"Are you getting yourself all hot, Eric?"

"Yes. And it hurts."

Nick fondled my tits through the jacket, and ran his hand up my leg; making the pain worse as I got super aroused. I sucked in some air in both pain and ecstasy. He fondled the head of my dick through the panties.

"Your pussy will ache until you cum. The more stimulation. the greater the ache. You're a smart girl, do the math."

Oh, my god. I'd have to get fucked to see any relief. Being dressed like this turned me on. Physical stimuli turned me on. This would make me the horniest slut on the planet.

"Oh, god, no. No, Master. Please."

He ignored me and continued to feel me up. I was panting with pleasure and pain. it was too much. I needed to be fucked.

"Fuck me, please."

"Could you be more specific, Eric?"

"I need your cock in my ass."

"You need my cock in your girly ass?"

"Yes master, I need your cock in my girly ass. Please fuck my tight, slutty, girly ass!"

"But you're not a girl, yet, Eric. You don't have a girly ass, do you sissy boy? I don't want a sissy boy like you as my secretary. I want a sexy slut; hot for my cock. Do you want me to train you to be my girl. Eric?"

I hung my head in shame.

"Yes."

"And...?"

"I am your little sissy bitch, Master. I'm a worthless, sissy fairy slut, who needs to be fucked like a little whore, and taught to be a real girl... fuck my little sissy pussy, master, please. Make me your sweet little fuck toy. Teach me how to be a girl."

"All little sissy sluts need to learn that it is impolite to ask to be fucked without paying respect to the cock that will please them. Real girls already know this."

He took his cock out and wagged it in front of me. I greedily took his cock in my mouth and made love to it. I looked up into his eyes, and moaned as I sucked him off. I wanted that cock in my ass so bad, I'd do anything to get it. But I did too good a job. He came in my mouth. made me show him his load, and then commanded I swallow it, and thank him.

"Thank you for you sweet cum, master. I hope I earned it."

He lifted my chin with his had, and smiled.

"Very good my dear, But my cum is not enough to kill off that little sissy faggot, Eric. For you to truly become Hailey you're gonna need to be dripping cum from both ends."

Oh my god, what was he talking about?

"That's right, Eric. It's not simply enough for you to say all the right things. I'm gonna make sure to obliterate anything that remains of you so that your inner girl can be free."

He motioned for me to stand up. I did, and wobbled on those heels as he led me by the had into the living room.

As we rounded the corner, I froze. In the room stood David Ham, the man who had fired me, and five other men I recognized from work. How long had they been there? Nick grabbed my collar ring and dragged me into the middle of the room, and turned me around so they could see me from all sides.

"Hello everyone, You're all here because you got my text, so I don't need to explain everything to you. And I'm sure you don't recognize this little sissy slut as Eric, the IT guy. But this is he. And Eric has volunteered to be this evening's entertainment. He has surrendered his faggot sissy ass for our pleasure. Eric wants to become one of our new office girls and be called Hailey, but he has not earned that right yet, so only when this little faggot has given you what you crave, fulfilled all your manly pleasures and behaved as a perfect slutty girl, may you call him Hailey. Until then, you will call him Eric, or sissy, or faggot, but he must learn to walk talk, suck, and fuck like a girl before he may be treated like one."

I was embarrassed to have these men who knew me see me like this. I tried not to look them in the eye, especially considering the lustful way they were looking at me, especially David.

"Wow, Nick. This is your best work yet. I didn't see it back when you told me to hire him, but man he is one sexy little cunt. I'm hard just looking at him." David said, rubbing his cock.

"Then you're the only one, Dave. I saw it the moment he walked in the building eight months ago. Took him long enough for him to fuck up. I've been eyeing his pretty mouth for months.", quipped Mark from accounting.

I stammered, "You mean. You had this planned the whole time?"

"It's human nature, cunt. People can't not snoop. We opened the window and you crawled right through it. So did our last little project. I think you know him. Emily?" sneered Phil; the Northwest Supervisor.

"Emily was..."

"His name was Emeril. A nosy little French fuck. And he fought us pretty hard. He hates being a girl, which is why I think I like fucking him the most. Watching him trapped in that super sexy body, swirling my cum around in his sexy girly mouth, and begrudgingly begging to be fucked. Serves him right for being such snob." Ted the Southeast Supervisor said unbuckling his pants.

I was feeling even more betrayed than before. The girl I tried to defend was a victim like me. And had helped set me up. I knew now why there were never any sexual harassment suits at work. I was pretty sure these devious fucks had a way to blackmail everybody.

"As an office girl, you'll be expected to service all of the executive staff, you'll entertain prospective clients, give them whatever they desire. But we're getting ahead of ourselves. You still haven't proven yourself. You might fail tonight, and then, sadly, it's prison instead. Either way, you're gonna get filled with cum. But at least with us, you'll get benefits." David grinned as he took down his pants.

They all began to strip.

"What's it gonna be, Eric? You're gonna be a bitch either way, but the food's better on the outside," Nick sneered.

I'd been used. Played. Made into a sissy slut, and soon to be humiliated as an office whore, a plaything for these assholes. I was really being sentenced to prison either way. Nick reached up my skirt and rubbed my pussy. I was reminded of how being fucked like a girl really wasn't that bad.

I unzipped my jacket, shrugged it off, and let it fall to the floor. I strutted up to David, pushed him back onto the sofa forcing him to sit. I did a sexy lapdance/strip tease; dropped my panties and stepped out of them, then dropped to my knees and took his cock in my mouth. Nick had a point, the food was better on the outside. I pointed my ass at the others and wiggled it.

"Gentlemen, make a woman out of me."

Nick pounced on my ass first. I was shocked to find that it felt amazing to have two cocks in me. They all took video and pictures of me getting fucked from start to finish. They forced me to strut around the room until I got my gait right, and could shake my ass in those heels without wobbling.

They spanked me anytime my voice sounded even a bit manly or falsetto. They took turns fucking me till my jaw ached, and no one in the room could cum anymore. I was covered in cum, on my back, on my tits, in my ass, on my face, and I lost track of how much was inside me. But by the end, I could walk, talk and fuck like the girl I now needed to be.

I was exhausted, but I felt like I had proven myself worthy. I could barely move when Nick placed the ball gag in my mouth, and slapped on the bondage cuffs. He moved me to the center of the room, and trussed up my wrists from a loop in the ceiling holding my hands high above my head. He kicked my legs apart, and attached a spreader bar. I was immobilized, but kind of confused. They owned me, why did they need to tie me up? I had nowhere to run. I started to get a little afraid.

Nick unfastened my corset, and removed it. He wiped all my make up off, and then swabbed my face with alchohol. He took a hot towel and wiped the cum from my back. David plugged in a tattoo gun. NO. They were gonna tattoo me. I complained through the gag.

"That's right, cunt. You have to get inked. Enrique here is very talented."

I squirmed to get free, but I could barely move. Enrique our marketing head came around front and grabbed my lower lip, he dipped the gun in ruby red ink and began tattooing my lip. I screamed in horror, for all the good it would do me. He tattooed my lower and upper lips. It was excruciatingly painful but my endorphins kicked in and soon I was numb to the pain. Then he moved on; tattooing charcoal black eyeliner around my eyes. And then tracing a light brown over my plucked arched eyebrows. I cried when I realized I would always have to look like this.