Sissy Step Dad - Ch. 06

Laura gets Ted stoned out of his mind, gets him to lock up his cock, dresses him up, and takes him out shopping. Later, she shares her sissy in an office garage.

This chapter contains crossdressing, drug use, femdom, pegging, public sex (sort of), and MM oral and anal. If that's not your thing, thanks for stopping by, but please move on. Cheers.

Chapter 6

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I'd been dodging Cindy for more than two weeks now. She was constantly at the house, looking for her chance to fuck my ass. Laura thought it was funny as hell, and didn't help matters. Her solution was for me to just bend over, grab my ankles, and let Cindy have her fun. But I wasn't sure I wanted to open that Pandora's box. I had a feeling that once Cindy got her way, she was gonna become more demanding rather than be satisfied.

Laura and I talked about the events of the past two month on a regular basis. Initially to ensure that we weren't fucking up our marriage. Then to spice up our sex life. But since the last two sessions, it has been more about Laura ensuring I'm not gonna spiral into guilt over fucking Eve (my daughter) and getting fucked by Danni (my stepdaughter). So far, I hadn't succumbed to social dictates, and had even been able to go to lunch with Laura, Danni and Eve. But I wasn't ready for a repeat with Eve, which told me that I was still dealing with guilt on some level.

Other frequent conversations were regarding me getting boobs and spending more time exploring my sissy desires. Also, on the table was my revelation that I thought it would be fucking awesome to be like Jasmine. A sexy dominating bitch with spectacular boobs and a huge cock (well, perhaps huge is a bit of a stretch). Laura was completely onboard with that idea, but really didn't think I could pull off the dominating bitch persona. She said I was simply too kind and empathetic to be able to Dom successfully. We also discussed different scenarios on how to deal with my business if I should decide to get tits or go further like Jasmine.

I also told Laura about wanting to add mirror's to the rec room, and I'm happy to report that the rec room walls now support a number of mirror panels. In addition, Laura has been teaching me how to apply makeup, should I ever need to touch up my own makeup again. It hasn't been going very well so far. She does a magnificent job when she applies my makeup. But whenever I do it myself, I look like a cheap street whore, or worse like an ugly transvestite. But you know, baby steps...

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Earlier in the week, Laura told me she was taking me shopping on Saturday. Not something I particularly enjoyed, but I did love spending time with Laura, so I agreed. I was pretty much an introvert, so it wasn't like I had anything planned.

Saturday morning rolled around, and I was sitting in my home office, going over some trade articles, when I notice I couldn't focus. I got up to stretch and take a break. My brain went fuzzy and I nearly fell over. I looked around the room and propped myself up on my office chair. What the fuck - I felt like I was stoned. But not just, hey this is a great buzz, stoned - no, more like, fuck I'm way too stoned, I don't like this, stoned. But I hadn't taken anything.

"Laura! Laura!", I was freaking out - thinking I might be having a stroke. What the fuck were the signs of a stroke again.

"Laura! Help!"

Laura came rushing in to my office, "What's wrong?"

"I don't know, everything's fuzzy, off, weird, like I'm stoned, but I haven't taken anything. I think I need to get to emergency!"

She suppressed a laugh, "That's cause you are stoned. I spiked your breakfast with a shit load of THC oil."

"What the fuck? Why would you do that without telling me?" I was dumbstruck.

"I thought it would be fun to get you fucked up, and then fuck you while you're stoned and horny." She opened the robe she was wearing, a nine inch by two and a half inch thick strap-on was hanging between her legs.

Now that I knew I was stoned, my fucked up mind wasn't freaking me out any more. The massive cock dangling between her legs was making me hard. She knew that pot oil got me ridiculously horny as well as complacent. I licked my lips and walked towards her. When I reached her, I started to drop to my knees.

She stopped me. "Not yet sissy, we need to get you ready first."

She took my hand and lead me from the office towards our bedroom. "You go in the bathroom and make sure no hair is showing anywhere, then douche your little pussy for me."

"Are we doing another shoot today?" I asked warily.

"Not to worry. Today it's just you and me my little slut. But this is going to be special, so I want you to look your best."

As stoned as I was, I just smiled and went into the bathroom to do as she asked. The hair removal, was simple, I'd been keeping my body hairless since Laura and Danni put me in makeup and a breast plate two weeks ago. I did a quick face shave and then cleaned out my bowels.

I returned to the bedroom, clean and naked. Laura was waiting for me in front of her makeup vanity. She patted the seat and I sat facing the mirror.

"When I'm done today, even your sister wouldn't recognize you." She beamed at me in the mirror. "I want you to watch closely this time. You need to get better at this. I'm not always gonna be available to be your makeup artist."

"But I love it when you do my makeup. The intimacy and sensuality that happens when you're focused on applying my makeup is really special. I don't really enjoy doing it myself. It's just, I don't know, less, somehow."

"You're going to learn to do this yourself, or I'm gonna pimp you out to Cindy as punishment. And we both know you love the way you look in makeup, so don't try to pretend that you only do it for the intimacy."

She had me there, and she knew it. I did love the way I looked when I was done up like a slut. And it would be nice to be able to do it myself if Laura wasn't around. Also, I really was afraid that she might sick Cindy on me as punishment.

I shrugged, "Okay. I'll watch, but you've got me pretty fucked up - I don't think I'll remember much."

"Hmmmm. Fair enough. I'll train you another time." She spun me away from the mirror and began rapidly applying make up. No special treatment today. She was moving rapidly and methodically.

I reached out, "aren't you gonna sit in my lap and do my makeup like you usually do?" I pouted.

She slapped my hands away. "No, you're not getting that treatment again until you learn to do it yourself. I think you're not getting better just so I'll keep doing it for you, so you're now cut off from that treatment. Now sit there like a good little slut and behave."

She continued for another couple minutes and paused, "Don't move."

I watched her go into the closet and come out with a long, straight haired, raven black wig. "This will go nicely with your pale complexion."

She put a wig strap on my head and then placed and adjusted the wig. She stepped back and frowned.

"What's the matter; does the wig not suit me?" A month ago that was a statement I never thought I would utter.

"It's your eyebrows. They're just too thick and masculine."

"Can I see?"

She spun the chair towards the mirror and I gasped. The person looking back at me was not me. It was a woman with ugly eyebrows. Somehow, she had managed to make my nose look smaller and my face more round. My chin seemed less square and my eyes looked huge and feminine. Unlike the slutty makeup she'd put on me before, this was subdued and more like what women wear to the office. But she was right on two counts; my sister wouldn't recognize me (hell, I don't think my mother would recognize me, if she were still alive); and my thick, brow, didn't work with this more subdued makeup.

"You're right, but not much we can do about it."

"Well, I could pluck your brow and fix it. But you'd probably freak when you saw it without the makeup later. And it would be hard to explain to your employees on Monday. How about I just do a really minor thin job. You can explain that as, Manscaping for your wife if anyone asks."

I looked in the mirror and frowned. That ruined the whole look - now I did look like a dude in makeup. I tried to think about it - but I was seriously stoned and super horny. I was fucked up and wasn't gonna resolve this; I certainly wasn't gonna win any arguments; I shrugged and conceded.

"Fuck it. Just do what you're gonna do. And hurry, I need to get fucked, or to fuck you, or both." I reached down and stroked the cock still hanging between her legs; pressing it back into her pussy. She clenched her legs and gave quick groan of approval.

Ten or so minutes later, my thick brow was gone and two thinner but well shaped eyebrows framed my beautiful feminine eyes. I frowned again - still looking like a woman this time. I made a bunch of faces, trying to see if any made the man underneath visible - but she'd done it - I was completely passable.

"Wow. That's fucking amazing. I really think I could pass as a woman - providing I never have to speak. And if we cover my tattoos - they aren't particularly feminine."

Laura beamed at me in the mirror as I was examining myself. She seemed proud of the transformation she'd pulled off and the fact that I liked it.

"You really think so?" Her smile should have warned me she was playing with me.

"Hell yeah. Bet I could walk down the street to the mail box and no one would know it was me."

"You're on!"

"What! I didn't mean I'd do it. I just meant it would be possible." I sputtered.

"Fuck that. I want to see you strut in public."

I started back pedalling like crazy. "No way. What if one of the neighbors recognizes me? And I don't have any clothes, so what am I supposed to wear. I can't wear my clothes, that'd be a dead give away. It's not happening. No fucking way."

But I was massively stoned, and even I knew my arguments and my resolve were weak. I wasn't gonna win this one. I was fucked. And of course, Laura knew it too. She had planned this, I could see it now. I should have been pissed, but I was just stoned and fucking horny.

She pretty much ignored my protests and was already rummaging in the closet, no discussion was necessary in her mind. She decided I was going to the mail box, and that was that. Me - I was just sitting in the makeup chair, getting harder by the second. By the time she came out of the closet, I was stroking a raging hard-on.

She looked at my cock, "Well that won't do."

I looked down at my cock and smiled at her, "Can't be helped. You're the one that roofied me and got me all horned up."

"Even if I blow you, you'll just be hard again in five minutes."

"Probably. Guess you'll just have to scrap your idea and fuck me until the pot wears off."

She gave me a wicked smile and dropped down in front of me. She took my cock in her mouth and I figured I'd dodged a bullet. She started blowing me and massaging my balls. My balls get really sensitive when I'm stoned and my head went back as I moaned at the ceiling.

She was deep throating me, and copious amount of spit were running down my cock and onto my balls. One of her drool covered hands moved to my ass and started to spread spit on my ass pussy. I shifted forward in the chair to give her better access.

She inserted a finger and lubed the inside of my sphincter. A second, then third finger, quickly followed, as she continued to throat my raging cock. I was quickly building towards orgasm and let her know it.

"Of fuck yeah. Suck my cock bitch. Drool all over it. Gag on it. Pull on my balls. Oh, yeah, like that. Oh god, finger my ass. Give it to me. Oh fuck you're amazing. Oh shit, I'm gonna cum soon. Keep going. Oh fuck, yeah!"

She pulled off my cock and stopped playing with my balls. Her fingers were still in my ass, but had stopped moving too.

I looked down at her in desperation, "Don't stop! I was so close. Suck me, please! I need to cum!"

"I need you to promise me something before I finish."

"What? I'll go to the mailbox if that's what you need. I promise, just finish me!" I raved.

"But you can't go to the mailbox with a hard-on, and we both know you'll have another hard-on before you get out the door. But I have a solution, you just need to promise you'll agree, or you can just finish yourself." She wiggled her fingers in my ass just to make her point.

"Ohhhh Fuuuck! Anything! I'll do anything, just finish me!"

"You promise?" More finger wiggling, and she licked my cock head.

"Yesssss! Anything you want. Please stop torturing me and suck me."

She started licking my cock again and fingering my ass. "You like it when I finger your pussy don't you sissy. You're a cock whore and love having your cunt stretched and fucked. Don't you slut. You're a filthy, nasty cum slut. You let you're daughters fuck you with a baseball bat. You let them pimp you out to men. They fucked you senseless and came in your ass and all over your face, didn't they sissy? And you loved it! Didn't you! Tell me!" She impaled my cock again.

"I'm a sissy cum slut. I'm my daughters' whore. They pimped me out and I loved ever second of it. They filmed and sold my anal rape, pimped me out like a common street whore and pocketed the money, (well not really, but I liked to think about it some times). I'm a worthless sissy meat puppet. Just two holes for others to use and abuse as they see fit. Fuck me mistress. Make me your fuck puppet."

She was hoovering my cock and finger fucking my pussy like a mad woman. I blew my load and moaned in ecstasy - the pot buzz taking it to an extra level of intensity.

Laura continued to finger my ass and milk my prostrate as she sucked my raging hard-on. She sucked up every drop, then pulled off my softening cock with a loud pop. Opening her mouth, she played with my cum and then swallowed.

"Hey! You're supposed to share." I whined.

"Couldn't be helped. If I shared, it would have messed up your makeup. Now, I need you to keep your promise."

She reached into the drawer of her makeup vanity and pulled out a metal cage. I knew what it was instantly, I had seen it often enough in the Sissy Hypno videos I watched. It was a chastity cage.

I balked. "No way am I going into chastity. You women already have way too much control over me."

"You promised, and besides, I'm gonna give you the key. It's just so you can't get hard before you walk to the mailbox."

I stared at her for a minute. "Give me the cage."

She handed it to me and I looked at it. It was an expensive model. I had actually looked at them online, thinking I might buy one some day. It had a built in lock and there was no key.

"And the key." I reprimanded.

She shrugged like she was caught and handed me the key. I put it in the lock while she watched and I saw her pout. The key fit, but didn't turn.

"Nice try. I may be stoned, but I'm not that fucked up. Where's the real key."

She shrugged again. "Can't blame a girl for trying." And she pulled another key from the vanity drawer.

This key fit and the device unlocked. I tested the lock multiple times not really trusting her. Once satisfied that the key worked, I began to put on the cage. It was an easy fit, as the primary loop was hinged so there was no need to force my balls through a small opening. With the base ring closed around my balls and shaft, I fed my still soft, well lubed cock into the cage and fitted the cage into the base ring. I turned the key and it was done - chastity.

I stood up and looked in the mirror. There I was, a woman with no tits and a cock in a cage. The epitome of a sissy slut. I swung my hips from side to side and my cock and cage slapped my thighs. The cage had some good weight to it and felt nice. It pulled on my cock and balls, and my cock started to respond.

The cage fit pretty snugly when I put it on and there was no room for my cock to swell in diameter and only about half and inch of length. Once my cock had filled this space, it started to get painful. I was in the process of putting the key in the lock, when Laura stopped me.

"Don't. Give it a minute and you'll be fine."

"It fucking hurts. The cage is cutting into my shaft. I'm afraid of damage if I don't get it off."

"Wait. Just wait. It doesn't hurt that bad. Think about the spankings you've had and the crop. This is just discomfort. You're just freaking out because it's your cock and you're really stoned. Give it another minute. Men wear them all the time without damage."

I looked at her and she smiled reassuringly. "You're not hunched over any more. The pain is subsiding, isn't it. Just from me distracting you."

She was right, the pain had become a dull ache and my cock wasn't swelling any more. In fact, it seemed to be getting softer. I reached down and fondled the cage and my balls. No reaction this time. The cage seemed to be doing it's job.

She handed me a medium sized butt plug, about 4 inches by 2 inches.

"What's this for?"

"Just shut up and put it in." Her voice mildly exasperated, like she was tiring of dealing with a questioning child.

I took it and inserted it in my already stretched out ass. Laura took my hand and lead me to the bed where she had deposited clothing she had taken from the closet. She handed me black booty shorts and I pulled them on. As they reached my hips, I tucked the cage back towards my ass to provide the flattest look possible. Laura smiled approvingly.

Next came a bra of matching black lace.

"What about my breast plate? What's the point of a bra if I don't have boobs?"

"I got you something new for today." And she produced a box from behind her back. She must have grabbed it while I was putting on the booty shorts.

"What is it?"

"Put on the bra, then I'll show you."

I put on the bra quickly, having watched Laura put hers on thousands of times, it wasn't a big deal.

Laura opened the box. Inside was a silicon breast form with two boobs in one, to allow cleavage to be shown. It was very pale, like my skin, but with dark rose colored areola and nipples, and again, the nipples were pierced with little barbells, and the edges of the form were nearly transparent.

I reached out to touch them, but she slapped my hand away. "Nope, you don't touch until they're in place. After the shit show we had trying to get you out of the breastplate, I thought these might be a little easier to deal with, and they should be a lot less sweaty."

She moved in and started arranging the form into my bra. It was nearly a perfect fit. She released my new boobs and stepped back admiring her work.

"Okay, check them out."

I reached up and fondled my new boobs through the bra. They felt amazing. I bounced, and while they moved, they didn't tug at me like the breastplate did, but they weren't bound to my body as tightly either. I looked in the mirror. Wow, very nice, I thought, and I guess I nodded my head in approval.

"You like them, don't you?" Laura queried.

"They're nice. But they don't tug on me like the breast plate, so they don't have the same feel. But they do look good, I'll give you that."

"Well, they have some self adhesive, but normally, we'd glue them on and do some makeup blending, if necessary. Unfortunately, the glue didn't show up with the form, so we'll work on that some other time. For today, and going to the mailbox, the bra will hold them in place adequately, don't you think."

I was still admiring myself in the mirror. I was looking hot and fuckable, and my cock tried to stir in its cage again. I reached down to massage my caged beast and Laura slapped my hand away playfully.

"Stop playing with your cock. You look like a dude scratching himself when you do that. Now, do you think you're new boobs are good enough to fool people?"

I smiled at her, stoned out of my mind and loving playing dress-up. "Fuck yeah. I look hot."