Of course he’s back in lingerie

I just stared at the letter and the unopened box in disbelief. Fuck I’m in a worse hole than I was with just the debt. Now this fucking pervert wants to make me his personal sissy? Fuck there’s no way. I can’t do it. I can figure out how to explain this to Allison, just a one time thing. My boss would be harder to persuade, damn family values, but I think I can swing it. But he wasn’t kidding about the mob. I could have my legs broken or worse. My bookie had already vaguely threatened me and I needed to make a payment by next week. And this rich pervert did already give me money….

Dejectedly I walked over and opened up Allie’s drawer, visibly wincing at the sight of all the silk, lace, vinyl, and latex in the drawer. I grabbed the least offending non ultra girly set, a white lace Demi cup bra with not too many ruffles or bows, just a small white bow between the cups and some small ruffles on the shoulder straps. Compared to everything else in this drawer, it was the best I could bring myself to wear. A matching pair of bikini cut panties with a satin gusset. The semi sheer lace wrapped around the hips and ass, with the soft satin front drew my attention. Without thinking I ran my finger up and down the soft satin, relishing the velvety feeling on my fingers before quickly pulling my hand away like it was a hot plate.

I slowly undressed, trying to drag out the situation as much as I could hoping some divine intervention would fix all my problems before I debased myself once again. Sadly, none was coming and I sighed picking up the delicate panties stepping into them. The lace and satin felt electric on my skin, especially on my member that I softly and loosely tucked down so there wasn’t such an obvious bulge. My dick twitched at the smooth sensation but i willed it down so it wouldn’t get hard. Picking up the bra, I wrapped it around my torso backwards before hooking the little clasps and spinning it around. Looping my arms through the delicate shoulder straps, it looked silly sitting on my chest with empty cups so I manipulated what little flesh I had on my chest to let the miracle B cup bra do its magic.

I looked at myself in the mirror, pink lipstick in my hand, seeing my short haired male face and head sitting on top of my hairless and feminine upper body, now with the added bonus of the push up bra two small breasts with the cleavage that came with them. I shuddered seeing the dramatic difference between my head and my torso, dreading anyone seeing me like this. But the fear of losing my girlfriend, my job, and my legs made me push past it.

I slowly applied the shiny pink lipstick to my lips, trying to remember what that tutorial video said about applying lipstick. I applied two coats, making sure the lipstick was set with a piece of tissue. I looked at myself in the mirror again, seeing the uber feminine lips once again on my face. But why only lipstick and lingerie? No wig? No other makeup? No clothes? Was he just doing this to humiliate me more? If it was just to humiliate me, he was succeeding. Besides last night, I’ve never been more ashamed in myself.

I slowly walked back into my living room and sat at my laptop. The screen came to life and I saw my Twitter profile was still active. Shit, I guess I never shut it down. I already had over 100 new followers since yesterday with several unread DMs. No chance I’m reading those. But I saw I had a draft tweet waiting to go out. Clicking on it, I realized this guy was serious about his ****. There were two pictures of me from last night, one with my eyes and face covered but pushing my faux cleavage together towards the camera, my painted lips giving a sultry smirk to the camera. The other was a still shot where my face and eyes are clearly visible!!! I realized drunk me wasn’t nearly as careful with the camera as I thought! I was leaning back on my forearms and my skirt had ridden up, showing off a clear bulge in my panties!

But what really scared me was a picture from my LinkedIn profile, my headshot in a suit with my full name and employer on the screen! Undeniably it was me dressed like a slutty school girl I couldn’t hide that! Finally there was a gif of me blowing a kiss to the camera, my painted nails clearly on display as I pursed my lips and gave a little giggle to the camera.

I quickly deleted the offending tweet, afraid it might ever get let loose on the internet. Almost immediately a message appeared. DaddyM. No picture on his profile but his name gave me the shivers all the same.

“Looks like you’re online, princess. Are you going to cam with me and be a good girl for daddy? Or are you gunna be bad and Daddy will need to punish you by letting everyone know what a slut you are?”

I cringed seeing his name and his text. Fuck fuck fuck. Before I could lose my resolve I quickly hit the camera button and started a video chat, making sure my full face wasn’t on camera just my lips and bra covered torso. I don’t want to give him any more ammunition, even though he had enough to nuke my whole life.

His name popped up on the screen, the innocuous name taunting me as I squirmed, realizing that another man was watching me in this white lingerie. I almost jumped out of my skin when out of my speakers came a deep, gruff but suave voice.

“There you are, Princess Carli. Glad you made the right choice. Cute lingerie, sissy. Nice work with those little titties of yours, but we can make those much better. No need to hide anymore, girl. I already know everything about you. Fix your camera so I can see your face.”

I sighed as my heart raced processing what he asked me to do. Be fully on camera as Carl with no real disguise this time. But he was right. If he wanted to he could ruin my life with what he already had on me. So I adjusted the laptop camera, showing my clearly male face and hair that clashed with my feminine body.

“Good girl. Got some work to do on that head of yours but I love a project. Now I want you to say hi to your Daddy. Say ‘Hiiiii Daddy! It’s, like, soooo good to talk to you. Your sissy princess has been dyyyyying to talk to her big strong Daddy’ and giggle at the end of it. Do your best at a girly voice, sissy”

My anger rose up at that moment. No way was he gunna have me act like some dumb bimbo!

“Fuck no dude! I’m not doing that shit. Now what do you want? I don’t want to do this shit anymore!” I angrily shouted.

“Tsk tsk, princess. Such foul language, and such a masculine tone. But I like my girls to have some fight in them. Makes making you into a soft and feminine girl all the sweeter. Maybe you need a reminder of who’s in charge here”

The text came up on screen but so did a picture from Allie’s Instagram!

“Do you want your pretty little girlfriend to find out what a sissy you are? Or about the debt you have to the mob? Which one do you think she’d be more upset about?”

“No! No please no! Don’t do that please! It’s just… this is a lot ok?? I only cammed that one time cause I was **** and drunk! I’m not gay and I don’t want to dress… like this” I pleaded gesturing to the white lingerie clinging to my body.

“Oh I know you’re not gay. Just a **** little straight boy. But that’s what I like. Making straight boys do what I want them to do and becoming pretty little princesses. So, I won’t say it again.”

The screen share switched to a DM to Allie linking to my Twitter profile!

I was shaking with fear and anger hearing his message, forcing myself to take deep breaths to settle myself down. God holy shit I am fucked. Steeling myself, I looked down at my lap, unable to look at the camera, but all I saw were two small lace mounds on my chest and my cock covered in white satin and lace.

“Hi, um, Daddy. It’s good to talk to you” I muttered with a slightly higher sounding voice.

“No no no definitely not girly enough, try again. And say exactly what I told you to say, princess”

I sighed and rolled my eyes, trying to hold back tears. They were angry tears, trying to convince myself I wasn’t completely humiliated. Steeling myself but still looking down at my lap I said,

“Like, Hi Daddy! It’s like sooooooo good to talk to you. Your sissy princess has been dyyyyying to talk to her big strong Daddy *giggle*” I tried my best at a girly voice but it came out more like a campy gay guy. God that giggle was so embarrassing.

“Better, princess. Much better. But this time look at the camera and smile. You’re gunna have to get better at this if you want to make any money, girl”

Ugh, this guy was the worst. Wasn’t it enough I already emasculated myself?? But forcing my eyes to the camera, I put on a half smile and repeated the words.

“Again, bigger smile, more bubbly. Well work on the voice in time but I want enthusiasm.”

For the next ten minutes I repeated the phrase over and over, with Daddy M trying to coach me on how to do it properly. Big smile, slight bite of my lip, wiggling my shoulders. Things the cam models I watched do on a daily basis I now watched myself do in the little corner of my screen.

Finally, the bastard had me stop.

“Hmmm that’s better. Not the eager sissy slut I made you out to be on your profile. I can see the hesitation in your eyes and body language how much you hate this. And that’s fine, princess. But actually, this might be a better vision for your career.”

“Um, what do you mean vision? My career? I already have a career and a life and a girlfriend. Just please, let me go and I promise I won’t do this again and will never bother you!” I said trying to reason with him

“Yeah, that might just be perfect. Can’t completely **** a new personality on someone that doesn’t want it. At least I can’t do that immediately. Let me think on this and make some adjustments to your plan.”

God the bastard just ignored me! He really did get off on this shit, the freak!

“Now let me tell you how this is gunna go from now on, princess. I own you now. You know what info I have on you. Plus, you need me. Well, right now you just need me for my money. That will change, I can promise you that. But I hold all the cards, and a gambler like yourself knows you’re fucked.” His smooth deep voice talked about my life like it’s yesterday’s weather!

“Now, money wise there are two ways you can earn. One is by camming. And I think with the new vision I have for you, you’re gunna be very popular. We will start camming tomorrow night to make sure you’re ready for your big debut. Tomorrow, you’re taking the afternoon off as I have a number of appointments you’ll be going to. And if you have plans with Allie, I’d probably cancel. Don’t think she’s ready to see you like this yet hahaha”

Shit, an entire day with this asshole? But fuck what else could I do. And what does he mean “like this”? What’s he planning on doing to me?

“So we’ll start out Saturday and see how you do. We’ll probably plan on two to three weeknight streams and of course every night on the weekend. Sundays I’ll give you off. Now there’s other stipulations and tasks regarding your streaming, like diet and exercise and other lifestyle changes, but we’ll get to that tomorrow and Saturday”

“Woah lifestyle changes?? Diet and exercise? And that many nights streaming as a cam girl? What the fuck?”

“Language, princess. Language when talking to your Daddy. Well work on your obedience, my punishments are very effective. But yes, lifestyle, diet and exercise to keep your body trim and plump in the right places. And for the amount of streams, I believe you have a deadline to meet and camming is gunna get you to that deadline, no?”

I just glared at him with my mouth open before seeing how my lipsticked mouth looked open like that before closing it with a snap. But the glare stayed. He was right about the camming, but what were these lifestyle changes.

“Anyway, the second way to make money will be something you enjoy: gambling. Well more so bets rather than games. Bets between you and I on tasks I’ll give you to complete. If you complete the task, you get money. If you don’t, you’ll still get some money but not nearly as much but you’ll also get a punishment. Or maybe a reward depending on how your little girly brain looks at it. Isn’t it poetic, the same thing that got you into debt is gonna get you out of it. But maybe a bit different than betting on the Giants to make the playoffs. By the way, what a dumb bet to make. The Giants are terrible!”

Huh, that didn’t seem so bad. I did enjoy a gamble. And if it’s tasks then I’d have a much higher chance at winning than sports betting or casino games. Wait, did he make fun of my Giants bet?

“Hey! They were supposed to make a come back this year! Not my fault everyone got hurt!” I complained with a loud “hmmmpphh” at the end crossing my arms. But seeing myself in the computer camera, I looked like a bratty pouting femboy pushing his tits together with his crossed arms.

“Hahaha well I’m glad you thought so cause that dumb decision dumped your sissy ass right in my lap. Now, let’s do one of your challenges tonight girlie. And since I’m feeling so poetic and since you think you’re such a tough ‘straight’ man, we’ll do a challenge on masculinity. Might be difficult for the ‘man’ sitting there in white lingerie to complete though. Two choices: one is a strength test, the other trivia. What’s it gunna be, Princess?”