tagTransgender & CrossdressersLesser of Two Evils

Lesser of Two Evils


[So to update you all. I'm sorry I haven't completed any more chapters of NWTBYG or Porn Princess. They're in the works, but creation, and good storytelling takes time, something I have less of now. I left my receptionist job to take a writing gig, and all my writing energy is going into that, but my passion for hot stories smolders intensely under the surface, so I've been reworking a story I wrote a while ago - my first failed attempt at writing erotica. It's easier to resurrect this one up than to create new stuff for already beloved characters. I hope you'll be patient, and enjoy this in the meantime.]


My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for guys like me.

Like most computer nerds I'm your typical slightly built nerd. I liked keeping my dirty blonde hair a shaggy length, almost down to my collar. Thanks to the company dress code that was meant to distinguish the executives from the monkeys like me, I was encouraged to dress down, so for me that consisted of jeans and a hoody. I had a private office on the 3rd floor, which I rarely ever had to leave.

The previous support tech had installed VPN software so that he could diagnose, and fix workstations remotely. I liked the VPN cuz it would save me a ton of time walking all the way to look at a machine that was buggy. In fact the only times I ever had to venture out was for lunch, or if there was a computer that wouldn't physically turn on. I would sometimes remotely mess with some of the really hot girls machines so they'd have to come get me.

The secretaries to three of the highest ranking men in the office: Emily, a drop dead gorgeous French beauty with light brown hair and a sweet sultry voice, Heather, a Jessica Alba-ish Latina with huge tits, and luscious lips, and Krystal, a tall natural blonde with a Georgia accent were my favorites... well everybody's favorites. They could all easily be models. I often wondered why they weren't models instead of office assistants, except that they all seemed very bright, and very content in their jobs. I couldn't get enough of their scent or their goddess-like bodies. I longed to be with them, but they'd never be with a guy like me who was unremarkable, and who made such little money. So I found some pleasure in finding opportunities to get close to them, to steal glances down their blouses, up their skirts, and fantasize about being with them.

Now one of the fun things to do when I was bored was to snoop through peoples machines via the VPN. It logged what porn sites they would visit, any pictures or movies they'd download. I was supposed to report this kind of activity. But I was so bored that this little spy game filled my dull days with something interesting - laughing at everyone's fetishes, and tricking the girls to come get me so I could be close to them.

We housed the regional supervisors for all four corners of the country in our buiding. The supervisor for the Southwest region was a total douchenozzle in his late 30's named Nick Lansfeld. He was always coming onto the secretaries and other female execs, making suggestive comments, and getting really handsy with them. All the top execs did it, and they always seemed to escape any sexual harassment issues. I guess cuz because everyone they were held accountable to was every bit as perverted. I know; I've seen all their porn snooping habits.

Well, Nick had probably the most perverted taste. In addition to all usual cream pie, barely legal, and bondage porn that seemed to dominate the offices of the upper echelon, he liked sissy porn. He would download lots of vids of men being humiliated by women by being forced to dress in frilly girls clothes and either taking strap-on's from the women, or being forced to take men's cocks, while the women goaded them on and humiliated them. I had deduced that he was probably like most powerful men, had some secret fantasies about being turned into a sissy bitch.

One Friday afternoon, I saw Heather and Emily come out of his office upset. Emily was crying, and Heather was pissed. I stopped them and asked what had happened. Emily wouldn't say anything, but I could see the red finger marks on her wrist. He had clearly grabbed her very hard. Heather adjusted her skirt which was slightly pulled up enough to reveal the tops of her stockings

"Fucking pig," Heather mumbled on the verge of a full on breakdown.

"Somebody needs to do something," Emily mumbled in her sexy accent.

She was right, and I knew just what to do. Furious, I walked into his office and shut the door behind me. He looked at me in confusion.

"What do you want, techno- nerd?", He asked angrily.

"I'm your worst nightmare asshole," I snapped, "I know what just happened in here with Emily and Heather."

"Oh, you're sure about that, are you?" He sneered.

"Doesn't matter because I know all about your secret fantasies, sissy boy."

He paused for a moment.

"What are you talking about?"

"I know all about your little fetish."


"I have remote access to every computer in the building... including yours. I know everybody's dirty secrets."

"You've been spying on..."

"Yes, and I know exactly what's in your 'travel receipts' folder, Nicholas. And if you don't do exactly what I say, I'm going to inform David Ham, your superior, of your activities. And we'll just see what he has to say about it."

He scoffed, "Really?"

"Really," I smiled back.

"Should I call him for you?"

He picked up the phone, and dialed. I was sure he was bluffing.

"Go ahead."

I stood there smugly. Waiting to him crack. He put the phone into speaker mode. A man on the other end picked up --

"Hey, Nick. What can I do for ya?"

"I'm curious, David, if I were discover that someone in the company was say, snooping through another employee's computer files would that violate any company policies?"

"A few of them, actually, and a number of laws. Why? Do you have a reason to suspect someone?"

A chill went down my spine.

"Not really sure yet. I don't want to get someone in trouble without knowing for sure, I just wanted to see how serious an offense it was."

"We'd definitely terminate them, and likely press charges."

Nick grinned at me, as I turned white as a sheet.

"What kind of charges? Are we talking a pretty hefty fine, here, or what?"

"Very hefty, and they'd definitely go to prison. I think the minimum sentence is 5 years."

"Then I'd better be sure I have proof before making any accusations then. Thanks Dave."

"It'd be irresponsible for me not to recommend that everyone in the company change their passwords immediately, but I don't want to spook whoever it is, so let me know as soon as possible," Dave added.

Nick looked up at me as he leaned into toward the phone.

"Will do, buddy. But I'm sure I'm just being paranoid. I 'll let you know either way."

Nick hung up the phone. I was frozen in terror. He leaned back in his chair and folded his hands behind his head.

"Now, you were saying something, Eric?"

I stammered but couldn't speak. Nick smiled smugly.

"I wonder what would happen to a 'tough guy' like you in prison. Some pretty amazing things I suspect. Something maybe like this."

He cued up a video on his computer of a cheaply shot porn film with a slight man in a dress and lipstick being double teamed by two extremely well hung black guys in a jail cell. I began to tremble. Nick laughed.

"Relax, Eric. I'm not going to turn you in. In fact I could really use someone like you. I'm sure you are privy to information that can really help me get out of this shit job, and move up the ladder."

I realized I hadn't been breathing. I gasped for air. Nick laughed again.

"Tell you what, It's almost 3 o'clock now. Take the rest of the day off. Let's get together tonight somewhere where we can have a private conversation, say; my place? I'd like to discuss how our newfound friendship might be able to help us both down the road. Sound like a plan, buddy?"

Y-y-yes," I stammered.


He wrote down his address and handed it to me.

"8pm work for you?" he asked politely.

I nodded. He gestured to the door. I turned and left; feeling like a had dodged a bullet. As I drove home, I considered my options. It would take me a few days to erase any and all traces of the archives I had been compiling, and be sure there was no way for Nick to blackmail me. I'd meet with him tonight, and see what he had in mind, and then I'd start covering my tracks on Monday.

I arrived at the address Nick gave me. He answered the door of the house, and ushered me in. He offered me a beer, which I took. He gave me a quick tour, turns out he was quite the tech nerd himself. He had some of the coolest gadgets ever. Then he urged me to sit down on his couch. He told me some of his history as we drank. How he started out in the IT department out of college, and how he maneuvered himself into becoming an executive. He wasn't quite the douche I knew from the office. I really felt like we were kindred spirits. I stopped hating him, and I kind of admired his ambition.

"Eric, you're a bright kid. I could see you running the company some day. So tell me, all the juicy dirt you've dug up, and we'll figure out our next move form there." he said eagerly.

I proceeded to tell him everything I had discovered over the course of 4 more beers. As I finished dishing the dirt, he clapped his hands together.

"Eric, you are my ticket on to the board - major share holdings, and some serous power. And as I prosper, so shall you. You've got serious dirt on all the right people. Enough to really make things happen... for both of us. And I know just how to use it. You'll be making five times what you're making now, in less than 6 months. How does that sound, partner?"

He stuck out his hand, and I shook it. I was excited about the possibilities. I was pretty buzz from the beers as well, but I began to feel like Nick wasn't such a bad guy, and that this little mistake was a blessing in disguise. I just had to be sure to cover my tracks next week just to be safe.

"Now let me explain to you what our first move will be."

Nick went to a wall safe, opened it, and produced a stack of removable hard drives.

"After you left I went to your office, and exported all your data and activity logs, and snagged all your computer backups, and brought them here. Right here is all the evidence I need to bury you. So whatever thoughts you had about double crossing me you can forget about."

My jaw dropped. He was clearly smarter than I gave him credit for.

"Here in my hands is enough to send you to prison for a very, very long time. So in this little arrangement, you will play by my rules, or take your chances with the legal system, okay?"

"What do you want, Nick?" I asked warily.

"Eric, I want you to help me live out my fantasy."

He pushed play on his Bluray remote and a video played of a young slight guy being transformed by an older man into a sexy transvestite maid.

"Look, Nick. If you fantasize about being some guy's sissy slut, that's fine. I'm not judging you. But I don't think I'm the right guy to help you..."

He laughed heartily.

"You think I fantasize about being the sissy?"

"Why else would you..."

It suddenly hit me. What he was talking about...

"Ahhh, putting the pieces together now, aren't you, Eric?"

"No... NO! No way... I am not--"

"Before you finish that sentence. I want to remind you that based on everything you told me combined with these drives, I easily have enough evidence to send you to prison.... PRISON, Eric. Make no mistake, you will be a bitch in prison. And with that blonde hair, and those deep blue eyes, you'll be a very popular item. Just do this one thing for me, and I'll let you walk out of here with the evidence. Then we'll be on even ground," He said, as he put the drives back into the safe, and locked it.

I couldn't think. He made me lower my guard and then hit me with this. I was trembling. Both of my current options SUCKED. He put the drives back in the safe and locked it.

"Nick, look... there's gotta be something else I can do. I can't...I'm not gay..."

"Eric, I'm not a monster. I'm not gonna put a gun to your head. You are free to leave. But the only way to avoid being a prison bitch for the next twelve years is to be my sissy toy for the evening. No one ever has to know."

On the TV, the sissy maid was finished transforming into a sweet sexy slut and her mouth was eagerly pleasing her master. I did not want that to be me. But I had a flash of the prison video Nick played me in the office. Being Nick's fuck toy was unthinkable, but twelve years of brutal prison sex, and god knows what else terrified me. Giving in to Nick was the lesser of the two awful fates.

"No one will ever know?" I asked.

"Do you think I want anyone else to know I'm into this? The only reason we're even having this conversation is because you found out about it, and tried to blackmail me. I meant what I said about becoming partners to mutual advantage. But as I was collecting the evidence I needed to keep you in line, I saw an opportunity to finally live out my fantasy. It's so hard to find anyone who'll do this that won't betray my trust and this fetish getting out could really hurt me. Please, just this once."

I could try to argue that I would expose him if he didn't give me the drives, but by doing so, I'd be sentencing myself to hell. My legs were weak. My head spinning. I was fucked either way. Better to be fucked for one night, than for years on end.

"Okay," I sighed.

Nick smiled. he held out his hand, and I shamefully took it. He led me into the guest room, and asked that I strip. I did but I covered my junk with my hands. He pointed me to the guest bathroom, and handed me a bottle of Nair.

"Use this all over your body. I want you completely smooth, okay, sweetie?"

Ugh. I cringed when he called me sweetie, like I'd heard him call all the girls at the office countless times. I showered in shame. I couldn't believe I was doing this. The Nair burned as it deprived my entire body of hair. I stepped out and dried off. As I looked at my now hairless body in the mirror, I was having second thoughts. I wrapped a towel around my waist, and exited the bathroom, I looked for my clothes, but Nick must have taken them, and hid them. He came in and blocked the door.

"Drop the towel, darlin' let me see how smooth you are now."

Nick was considerably taller and stronger than me. I was 5'8" but he was 6'3" and clearly worked out. I dropped the towel. He twirled his finger in a circle, and I turned in a slow circle for him to inspect. He pulled out a pair of baby blue leather cuffs that he had been hiding behind his back, and approached.

I backed up into the wall, as he rushed to me, grabbed my wrist, and twisted my arm behind me forcing me to turn around. He held me in place, and cuffed my wrists. He pressed up against me, and I could feel his hard bulging cock rub against my ass through his pants.

"You are gonna make a sweet little fuck toy, Eric. I bet you can't wait to have this cock inside you. You want my cock, don'tcha, bitch?"

"No." I complained.

"Sure you do. No self respecting straight man would have taken my deal. You're not a real man. You're a sweet little sissy fairy, who needs to be trained to be a sweet obedient slut."

He ground his cock into me. I squirmed to get free, but he was too strong. He turned me around threw me over his shoulder and carried me into the master bedroom.

He dumped me onto the bed, and I saw a baby blue locking bondage collar, a leash, and baby blue ball gag laid out. He quickly grabbed the collar, forced it onto me, and locked it in place. Attached the leash, and tied me to the post on the bed. I couldn't run now. I was his prisoner. He unzipped his pants and pulled out his massive cock, and began stroking it.

"Please, Nick. I changed my mind. Let me go."

"Oh, no. You bitches are all the same. You play the tease; get a man all turned on, and then you want to leave. I'm not getting a case of blue balls from a sissy bitch like you, Eric. And I don't want to hear you complain, when I know how badly you want my cock. So let's put a stop to your whining."

He gagged me with the ball gag. untied the leash and dragged me over to the vanity where on the mirror were taped 20 pictures of drop dead gorgeous blondes in different sexy outfits. He sat in the chair, and pulled me on top of him. I could feel his hard cock against my bare skin.

"Pick one."

I turned and looked at him confused.

"Choose your fate, bitch. Which one of them do you want to be?"

He ground himself into me, and I could feel his hot cock against mine. What had I gotten myself into.

"Choose, or I'll choose for you. And you won't like what happens then."

I looked them over. My eyes settled on one in a sexy red lace chemise that looked a bit like Scarlett Johansson only skinnier, more statuesque, she was so sultry; the sides of her long blonde hair pulled back, and draped with the rest to fall down over her shoulders. I wanted to fuck her. Nick followed my eyes and pulled the picture down.

"You wanna be her, huh? I don't blame you, sweetie. She looks extremely fuckable."

I shook my head and complained. I tried to speak through the gag, and say, "No, I think she's hot, but I don't want to be her."

He turned the photo over and on the back was her name-- 'Hailey'

"Hmm, I like that You're going to become my special girl, Hailey."

He got up and left me in the chair. He pulled the rest of the pictures down, and tossed them aside. He stuck the picture of Hailey back up on the mirror. I could see my reflection next to her. I looked from her face to mine, and couldn't imagine ever looking like her.

"Take a good long look, Eric. Soon all you'll see in the mirror is her."

He said it with such finality that a shiver went down my spine. He strapped some sort of viking opera singer bra-like contraption with suction cups around my chest, and hooked up an air compressor. He flipped the switch, and I could feel the cups tugging forcefully on my chest. This wasn't in the videos. What was he doing to me?

He strapped me into the chair with velcro restraints, as the thing on my chest tugged away. He put on vinyl gloves and rubbed dye in my still damp hair. Bleaching it from dirty blonde to bleach blonde. He rinsed it out into a metal mixing bowl, and proceeded to dry and brush my hair, teasing it up, and attaching clip-in extensions and styling it until my hair looked just like Hailey's.

He rubbed hot wax all over my stubbled face, chin and neck. It burned mildly until he ripped it off taking my hair with it, and leaving my skin smarting, but completely smooth. He took more wax and smeared it on my eyebrows, and ripped it off - shaping my eyebrows until they matched the girl in the mirror. He never said anything about altering my appearance. How was I going to hide all this on Monday.

He grabbed a syringe and injected the contents into my lips - ten injections along the top and ten along the bottom leaving me with thick swollen lips. I squirmed and squealed in horror, as he took another similar syringe and began injecting it into my cheeks.

"Don't fret sweetie, it's just collagen. A temporary fix. It'll eventually absorb into your system in about 3 months or so."

Three months? This was supposed to be a one night thing. I struggled furiously to get free, but the straps were too tight, and with my arms locked behind me, I had no leverage. He went to work on my make up. The base and powder smoothed out my skin and gave it a glow. He highlighted my eyebrows making them more dramatic, as he added purple and pink eyeshadow combined with the dark dramatic eyeliner and mascara my reflection became startlingly similar to the girl in the mirror. He polished off my cheeks with blush.

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byAndi_Lembke© 41 comments/ 342573 views/ 282 favorites

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