"Maid" to be a Cuckold Pt. 01

"Are you sure you want to do this? It's a wild ass fantasy. You're basically saying you want me to dominate you, feminize you and sleep with other men?" Lauren asked.

"I mean if you put it like that, it's weird. And it doesn't sound right. But you wanted me to be honest!" I said in tears. I was having this conversation with my wife of 2 years Lauren.

We've been having more than a rough patch and it didn't help that Lauren found a stash of "sissy porn" in my hard drive. That sparked a month-long confrontation which led to this long-winded discussion/argument/fight where I basically laid out all my cards and expected her to leave me any moment but instead she seemed oddly amenable.

"Okay, I need a breather. I'm going to Erica's for the night. I'll come by tomorrow and we can talk then" she said thereby ending our conversation.

The next day dawned and while I tossed and turned through the night, Lauren came in looking fresh as a daisy, as she always did. Lauren was my height, which wasn't saying much as I was only five foot 7 inches. Lauren in fact wouldn't wear heels sometimes to boost my ego. Her brunette shoulder length hair was usually tied into a bun or single ponytail. Her body was one of the reasons I fell in love with her. I was not exaggerating when I say, she had the best body I've ever seen. Perky tits, round spankable butt, and the tightest pussy that made me cum in no time.Was I a fool for getting myself into this?

Before I could think too much about the topic, Lauren sat across from me and cleared her throat as if about to speak.

"So I did some thinking and talking about it with some friends." she started.

"Wait what. You told people??" I said rather incredulously.

"Well duh. I needed my space. You have basically been a closet trans person or at least living like someone else hiding all this from me, I think I'm entitled to react in my own way." she said as she sipped her coffee.

I nodded. It was horrifying that Lauren's friends knew but I could see that it was weirdly fair.

"So yeah I talked it over, and Liz suggested that it may all be somehow related to a humiliation kink? Is that it? You just like to be humiliated?"

I nodded. "Um, kind of. I mean to be clear I'm not trans and I'm not gay but what drew me to doing sissy porn was the humiliation aspect of it, and how demeaning it was to not measure up as a man, that I'd be a woman"

"Hold on, you think a woman is less of a man?" she said as she stood up in anger.

"No no no. I mean I am less of a man." I said, trying to explain.

"Hmph. Okay. So basically the humiliation does turn you on?" She asked as I nodded.

"Okay I'm not going to lie. I kinda like humiliating you too. It not only turns me on, but it also gives me a sense of control over you that I really like. So why don't we make a deal. We'll give this a shot. I'll be your "mistress" or whatever, I'll humiliate you, dominate you, but you have to tell me when it gets too much. We'll have a safe word system in place. If it gets too much, say the word and we'll stop everything. No questions asked. Agreed?" She said, reaching her hand out as if we were striking a deal.

I shook her hand in agreement.

"Okay awesome. Secondly, as you know, I've told my friends about this, and I think they have some great ideas. By agreeing to this, you're also opening up our marriage, because I need some satisfaction too, and well seeing you prance around like a femboy may not make me the wettest. I don't know how soon I'll be doing this and I may not do it immediately but somewhere down the line, our marriage will be opened up. Right now I've told Erica, Liz, Vanessa and Amanda. I can't promise no more people will know, but we can try to limit it" she said.

I took a deep breath and nodded once again wondering what I was getting myself into.

"Okay. I agree to that too" I said.

"And lastly you will follow my orders. I don't like you calling me Mistress. Or Mommy. At least not yet anyway. But maybe you can call me Miss Lauren for now? You follow my orders, and I'll fulfill your kinky fantasies. It's a win win, but I need you to commit and I will too. And I mean really fully, commit. We won't be doing anything illegal or risky that could make you lose your job or get you arrested but it will be worth it. So are we in agreement?"

I was about to say yes, but an instinct rose in me, what was I saying yes to? I obviously could back out anytime using the safe word but what was I backing out of? "Um. Can I ask for more details?" I asked.

"Well I guess that's fair. So Liz said the whole sissy fetish really digs into emasculation, humiliation, and subjugation. She said you may prefer to live as a sissy, someone whose femininity is exaggerated to the point of caricature. But that turns you on. We both know you were bi curious. So here's some of what I'm thinking, after work you'll serve me as a sissy maid. You'll be at my beck and call every evening and night and maybe even mornings on the weekend and I will reward you appropriately. That's the jist of it."

I couldn't hide my boner any more and it was tenting my pants. Lauren noticed. "I think your little friend there agrees?" I nodded.

"Alright then. So can we start today?" She asked as I mouthed yes.

"Okay good. Here's what I want you to do. I want you to go shower, and shave everything smooth below your neck. Completely smooth. If there's even a single hair beyond your neck? I'll make you do it again. Am I clear?" She said as she started to bask in her newfound authority.

"Yes" I mumbled.

"I'm sorry?" She said her voice and eyebrow raised.

"Yes Miss Lauren." I said and nodded.

"There we go! Now go do that, and when you're out of your shower, I want you to moisturize your body with some stuff I'll lay out. Also, don't wear any clothes until I tell you to. While you shower I'm going to go get some stuff for you, and I want you to be butt naked when I'm back. Am I clear?" She asked, once again with that new authority.

"Yes Miss Lauren" I muttered.

I went up to the shower and started the water while I heard Lauren on the phone. I couldn't make out what she was saying but she was giggling quite a bit. I started shaving my legs and then moved to my arms before I realized I'll probably need to shave my balls and my taint. I started struggling with the razor between my cheeks when I heard Lauren's voice say "I'll be back. Remember what we said! See you soon!"

I didn't respond because I was trying not to cut my balls. I heard the door shut. For the next twenty minutes or so I delicately shaved every inch of my body, rinsed and moisturized while I waited for Lauren to return.

Almost a full hour after that I heard the door downstairs open and to my shock it seemed like Lauren wasn't alone? I heard another voice with her. I panicked and was about to get dressed when I remembered her warning. I covered myself up best with my hand while I heard two footsteps.

"Hey we're back!" Lauren said as I saw her and Liz with her.

Liz was one of Lauren's best friends who worked as a therapist who dealt a lot with kinks and fetishes, and moonlit as a kink counselor on the internet. I should have expected her sooner or later. Liz was an open lesbian and was married happily to her wife, Vanessa. Liz was a brown woman with hair almost always styled into a pixie cut, she was a little shorter than Lauren and by proxy me, and always dressed a little androgynously compared to her wife Vanessa, an Asian woman who was almost always femme.

"Hello! Oh don't cover up on my behalf. I'm here to help!" Liz said acting very nonchalant about my nudity.

"So Liz and I talked a lot and she basically was the driver behind a lot of my choices. She told me you'd enjoy this, and she also gave me quite a few tips. I guess there wasn't any other reason to bring her home other than to further humiliate you, but Liz is actually the kind one." Lauren said as she put down the bags she was carrying.

"It's true. Vanessa is so much meaner, and well if she saw you like this, she'd probably have a field day! Well she's not here, so you don't have to worry. For now anyway!" She said as she sat down on the bed.

"So here's how it works, Liz has given me quite a few suggestions and some helpful tools to keep you in line. The first of which is taking away your masculinity in every way we can think of. So from now on, you'll be wearing women's clothes at home. You don't have any for now, so I bought you some basics. Tomorrow you and I can go shopping, and when the store clerks ask who it's for, you bet your ass I'm going to tell them it's for my sissy husband" That itself was enough to give me a boner. Unfortunately being naked meant I had little to hide. Liz saw this immediately.

"Omg. I expected this! It's good to see for myself! Okay Lauren, you can go ahead with the rest of the plan. He will love this" Liz said very matter of factly.

"So we have a few things for you! First things first, Liz you want to show him?" Lauren said.

Liz brought out a pink device from her purse. "This, as I'm very sure you are aware of, is a chastity device. And what does a chastity device do?" Liz asked like a teacher asking a student the answer.

""It locks my penis away." I said.

"Hmm, and why does it do that?" Liz said as she got on her knees with her face inches away from my penis.

"B-because. Because it's useless." I whimpered.

Liz giggled. "My god Lauren. I have to borrow him. He's so good at this! He's a born sissy! He'd be such a good role model for some of my sissy sessions! Anyways you probably should do the honors so come here" Liz said to Lauren as she got on her knees as well.

"So you put this piece through the balls and this one on the shaft and using this key, you lock it up and voila!" She said as Lauren followed her steps.

The cage was bright pink and had some jewels on the shaft! "Wow. So I get to keep this key?" Lauren said.

Liz nodded. "Not only that, you get to decide when he gets out of it. You could use some sort of punishment reward system or you could just keep him locked up for whenever you want. As long as you call the shots."

"Oooh. I like this power. Okay so one of the things I asked him to do was to shave, and I said I'd inspect him, so can that be something I can judge him on?" Lauren asked.

"Of course! " said Liz.

"Alright. Step over here and show us your body sissy" Lauren said.

I stepped over near the mirror.

"Liz, you want to help inspect him?" Lauren said.

Liz nodded as both of them started to look at my hands, legs and chest. "Hmm okay I think the body looks good. But we need to see his boi pussy! Spread 'em sweets!" Lauren said.

Reluctantly I bent over and spread my ass cheeks in front of my wife and her friend.

"Not bad! I think I can approve of this! What do you think Liz?" Lauren said.

"I'd agree. Especially for a first timer!" Liz said as I blushed.

"Okay so I think there's just a couple more things for tonight, so why don't you take this bag and wear everything in it. In front of us. I'll give you two minutes. Liz starts the time. If you don't finish on time, you may not get unlocked tonight!" Lauren said.

"Wow. I have worked with a lot of couples but you both really gravitate towards your roles! I'm impressed! Also your time starts now Sissy!" Liz said.

I immediately emptied the bag and tried to separate its contents. It was a pink maids costume with a tie on top, a tiny skirt, a thong, two thigh highs, pink heels and a head piece. I started hurrying and wearing everything and managed to get everything except the tie on top piece when Liz said "Whoops! Times up!".

I frowned. "Aww. Well too bad. You won't be unlocked tonight. Unless. You follow everything I say for the rest of tonight. I have quite a few ideas!" Lauren said giggling at Liz.

"I think that's enough humiliation in front of Liz today. Although we have one more thing for you. You're clearly not a man, but not yet a woman. And while I can call you sissy, I think you need a name. Liz says you've thought of this. So what's your sissy name?" Lauren asked.

"Samantha." I said as I winced. Liz and Lauren started giggling.

" I think that's a cute name! It suits you! You're a real champ for doing this!" Liz said as she came closer and gave me a peck on my cheek. I blushed. While I was caught unawares, Lauren took a bunch of pics in my maid uniform.

"This is for Vanessa! She would love this!" Liz agreed and bid adieu.

"Alright Samantha. So here's the deal. Every evening after work, you're going to wear this outfit, and do as I say. Every time you're obedient and a good maid, I may reward you. Any time you're a bad girl, I will punish you. Sounds simple enough?" She asked as I nodded.

Lauren raised her eyebrows. I understood what she meant and said "Sorry Miss Lauren, I meant yes Miss Lauren. "

"Good girl! Your first task tonight is to go gather all your male underwear and bring them here in a pile. You have 5 minutes." I ran as fast as I could in my heels and brought all my male underwear.

Lauren had gathered a trash bag "Good girl. Now place all of them in this trash bag and place it in the trash can outside. You are no longer a man, and thus have no need for those boxers of yours. You and I are going to go shopping tomorrow for more girly undies for you and some sexy lingerie for me. I'll need some as I go on dates you know!".

I whimpered at the mention of the last word.

"Aww. Is little sissy scared? Scared that a big stud is going to fuck me senseless like you never did before? Serves her right. She never measured as a man, and thus deserves to be a sissy. Doesn't she?"

"Yes Miss Lauren" I whimpered.

"Now. It's been a long day hasn't it? But before you sleep in the bed, might I remind you that as a maid you're giving up your claim to the marital bed. That's only for me and my lovers. Occasionally if we want you to be involved you can sleep with us, but for the most part you'll be in the guest room by yourself. Understood?"

"Yes Miss Lauren." I said.

"Good girl! Now lastly, it's late and you should go to bed but I want to test how obedient you are in bed, and you have been a good girl so maybe I'll unlock you? Undress me" she said as I started to work on undressing her until she was in her bra and panties.

She turned around and I unhooked her bra to reveal her pert breasts. Was I really a fool for signing them off to an unknown man? She then gestured to me to remove her panties. I nodded and then got them off to reveal her glistening pussy. She was clearly getting turned on by all of this. She turned around as if showing off her naked body. I've seen her naked so many times, but this time felt different. It felt like she had a new found sense of confidence and sexiness which she was showing off.

"Mm. Now how about we get you naked too. Take off everything except your heels and your headdress." I obeyed and took everything off. I once again glimpsed at the mirror and saw a naked woman and myself, I wasn't very masculine in pink heels, hairless and a pink chastity cage.

Lauren then got on all fours and spread her legs. "I don't think you can fuck me anymore, so here's the deal. If you can make me cum with just your tongue, I'll unlock you tonight and give you an orgasm. But only if you can make me cum with just your tongue. Deal?"

"Yes Miss Lauren" I said as I positioned myself near her pussy and started licking wildly until I felt her flick my ear.

"Gentle you slut. My pussy isn't an ice cream cone. Go slower. Oh yeah, like that." she said as she guided me.

As I continued to eat her out, Lauren continued to moan harder and harder until I felt her whole body tremble and I could feel her come to orgasm. She laid back in exhaustion and a content sigh.

"You always were the best with your tongue" she said as she closed her eyes.

Not wanting her to forget her promise I stood by her obediently as if awaiting my new instructions.

"Oh well, you did obey me so I'll oblige. Here" she said as she took her key and unlocked me.

The minute she unlocked me, my penis sprang to attention.

"My god! Your little clitty just sprang out there huh? Well you aren't going to get to fuck me that's for sure. I'm feeling generous so how about a quick handjob? With you it's usually quick. Except I'll tell you when to cum. If you cum before that? You're going to be locked for one whole week. Deal?"

"Yes Miss Lauren. Anything to cum miss Lauren.'' I said as the lust was overtaking me. Lauren started stroking me gently when teasing my balls with her other hand

"Little sissy maid wants to cum? But this isn't how women cum. Or even little sissies. Do you know how they cum?" She asked as she continued to stroke me.

"No miss Lauren" I said as I started to roll my eyes in ecstasy.

"Uh uh. Not yet. No cumming until I say so! Sissies cum by getting fucked like the little sluts they are. They don't tug on their clitties. They fuck their pussies with dildos or let a stud fuck them. Can you imagine begging one of my new boyfriends? Can you imagine getting on your knees and begging the cock that just fucked your wife to fuck you too?"

I groaned in response. I was getting really close to orgasm and Lauren sensed it but didn't say yes yet.

"Such a sissy. We should have done this years ago. You were always meant for this weren't you? I wish you had told me earlier. We could have gone out and gotten laid together. Gotten our fair share of dick like the queens we are. Instead you hid it from me. And now we are reduced to this mess."

I whimpered and moaned "Please miss Lauren. Please can I cum".

"Fine. I'm going to take you in my mouth for the last time, and you can cum. You better fucking remember what it feels like because this is the last time I play with your little clit. Once you cum, I want you to kneel and close your eyes. " She said as she stopped stroking and took my penis in her mouth.

The minute I felt her warm mouth I started cumming. Lauren took it all in. I immediately kneeled and closed my eyes and felt Lauren stand. Lauren then spit on my face and let my own cum cover my face.

"Such a pathetic sissy. Go sleep. We're going shopping tomorrow." She said as she pushed me out of the bedroom in my heels and a face full of her spit and my own cum.

I went back to my bed ashamed and drained. After cumming so hard and in such a humiliating fashion, post nut clarity started to hit hard. What did I just do? Why am I dressed like this? Why is my dick locked up? Why am I sleeping separately from my wife? I managed to hobble to the guest bed, wipe my face and lie down trying not to cry but eventually whimpering and crying.

I must have blacked out due to exhaustion or emotional stress because the next thing I knew I was seeing a naked Lauren. "Samantha wake up! We need to go shopping! I don't have much time, I have a date tonight and you are going to help get me ready for it!" she said as she walked away, almost prancing around in excitement.

It was clear she was enjoying this as much as I was, and despite my post nut clarity and post nut depression, I wanted this, this was my fantasy too. One thought that haunted me however was last night when Lauren said something to the effect of "We could have been queens together" suggesting as if I could have come clean earlier and she would have accepted me as a sissy girlfriend instead of a sissy cuckold maid. I may never know the true answer to that question.

I hobbled over to the shower, my face had smeared make up and the tears didn't help the case either. I quickly showered, my smooth body still feeling foreign to me as I heard Lauren shout "If we're going to be late now, and this carries over to my date at night? I'm going to be so pissed. Hurry up slut!" she said as I rushed outside in a towel.