"Maid" to be a Cuckold Pt. 01

"I've laid some of my clothes on the bed. This is the last time you'll be wearing my clothes." She said as she pottered away in speed again trying to continue to get ready.

I took a look at the clothes on the bed. It was a pink bralette, a pink lace thong, black leggings, and a gray hoodie. I sighed in relief. I had worried that she may have picked something ultra femme and humiliating for me. Those fears became real as I grabbed the hoodie as I had missed something underneath it. A pink crop top that said "Slutty" on it and the hoodie while still gray, had the words "PINK" emblazoned on them in bright pink typography.

"Make sure you wear all of it! Oh, and I may feel cold later on. Just letting you know!" She said with a giggle.

I grumbled, as I wore all the clothes. I looked at myself. There was a tiny bulge in the leggings, but it was actually coverable with my hoodie.

"Don't forget makeup!" She said as she grabbed her coat.

Makeup would definitely give things away, and make me look like a humiliated sissy.

"No. Please." I said looking at Lauren.

"You wanted this. Your sick fucking fetish is getting off on being humiliated. So, I'm just helping you. You can wear makeup and come with me or not come at all. If you don't come, you're going to lose a lot of privileges I had planned out for the rest of the week and I will think of ways to punish your ass in ways you can't imagine. It's up to you".

I whimpered and moved to Lauren's room with her make up table. Lauren came by and looked at me.

"Hey, I know it's a lot. But don't forget, you can back out anytime. We have a safe word system in place right? " She said in a voice that was unusual for her in the past 24 hours.

I nodded. Did I want to use the safeword? Yes but also no. We barely scratched the surface of this, and I wanted to explore more. It was so humiliating, but so erotic. I shook my head and started applying makeup on my face. "That's a good girl" Lauren said as she pecked me on the cheek.

I finally finished my make up, and made it to the car when Lauren gave me the keys and made me drive to the mall. I was hoping it wouldn't be the mall I thought it would be. But my fears were confirmed when I was made to take the exit.

You see, I was scared because this particular mall had a store where one of Lauren's friends, Erica worked. Erica was one of Lauren's friends since college, and I knew her since then too. She was normally sweet and kind hearted but I had a feeling she won't be today.

As if reading my mind Lauren said. "Yup, this is Erica's store. I texted her and made sure she'd be working today! She does a really good job, and will definitely be really helpful!" She said giggling in a manner I could only start describing as evil.

I got out of the car and it felt like all eyes were on me. They probably weren't. But it definitely felt like that. I couldn't look at anyone, just focussing on the floor hoping we could teleport to the store.

We finally made our way to the store and it wasn't as crowded as I thought it could be.

"Omg! Lauren!! And Samantha!" Erica said excitedly from the corner of the store, instantly drawing attention to us instantly.

Erica and Lauren hugged while I awkwardly stood there hoping this would be over soon. Erica instantly turned her attention to me.

"I've heard all about you! I must say I love what you're wearing, it's so cute! I'm really proud of you for owning up to what you really are and what you wanted. Not many men, I mean women, have the balls to do what you're doing!" She said uncharacteristically loud as if she was intentionally drawing more and more attention to us.

I started to blush in embarrassment.

"So what are you two girls here for?" Erica said.

"Well, I have a big date tonight and I wanted something new and sexy. And Samantha here has no panties, or bras. Or lingerie really. So we decided to come here!" Lauren said looking at me.

"Well you came to the right place, I have the back room free, so you two ladies can go right in there and I'll bring some things for you both to try on!" she said as she rushed away.

"Well, I'm going to go find some lingerie, why don't you pick up some pairs of panties for yourself? Oh and try the bargain bin, they're cheaper! See you" she said, pointing towards the bargain bin which had quite a few women shuffling through.

I swallowed my fear and headed over there. I took a deep breath and started to rifle through the bin, looking for my size. I found quite a few cute panties when I saw Lauren walking towards me with a sexy negligee. "Samantha, do you think he'd like me in this? Does this say "Rip this off me daddy?" Or does it say "make love to me tenderly"" she said.

"Oh wow. Definitely the former. If I was your lover, I'd fuck you instantly. What do you think Samantha?" Erica said.

I nodded. "Yes it's very sexy." I said my eyes tearing up in humiliation.

Did she really ask me if someone else would fuck her in front of other people? Did they know what was happening? I started to feel light headed. I think Lauren sensed this because she asked "Samantha you okay? You look faint" I nodded.

"Do you have the panties you need? " I nodded again unable to say anything.

Once again Lauren sensed this and came closer, Erica could also sense this.

"Why don't you girls come with me in the back, we have some private changing rooms there and we can get Samantha measured for a new bra?" Erica said.

Lauren nodded, "Yeah that seems like a good idea. Come with me Samantha" she said, taking my hand. I was still mortified, but taking Lauren's hand definitely made me feel better.

Erica led us to a private room in the back with a round dais. "So let's get your bra size right. We can do this with your shirt on, but I highly recommend you take your shirt off, so I can measure accordingly." I nodded again as I took off my hoodie and my shirt laying bare chested in front of the two women.

It was then that I realized how surreal everything was, and how surreal everything happening was. I hadn't realized it but everything I did up to that point almost felt like an out of body experience.

Erica came closer and started measuring with her measuring tape at three different points, under my arms above my chest and across the chest. She quickly did some math and said "Okay you're a 32b! Let's get you the right bras."

After the bra measurements the rest of the trip went pretty uneventful. I bought enough bras and panties to last me a lifetime, some that I even found cute myself!

We got back home and Lauren wasted no time in getting ready for her date. But my humiliation which had merely hit a pause had to be made up for.

"So first things first, I need you to draw a shower and I want you to lay things out for me tonight and help me with my make up. Oh and some wine would help calm my nerves. Oh and also the crop top and the hoodie is cute and all, but I need you in the uniform with heels. Oh and pick up my shopping and put it away. You have ten minutes to do all the things I mentioned. '' She said as she sauntered off.

I rushed and stripped out of my clothes back to the maid costume. I was about to start with the bath when Lauren came up and said "Tsk tsk. I do hope you're not thinking you're complete. " she said walking up in her underwear.

"I expect my maid to be in make-up all the time. Every time she's not, she can expect to be punished later on. Are we clear?"

"Yes Miss Lauren '' I said as I bowed my head.

"I'm giving you two minutes more. And it better not be some fucking clown make up. You're a maid and you're better than that" she said as I ran towards the make-up table and tried to toe the line between being fast and being accurate.

I finished my make up and continued the tasks, setting the shopping away, laying out her clothes for the night. I was about to finish laying out some make up for her when she called for me.

I pottered towards the bathroom in my heels. "Samantha, I need you to help wash my back. I can't reach all of the places you know" she said with a smirk.

I tried to reach her back from where I was standing instead of getting into the shower when she giggled. "Silly bitch. You'll need to get into the shower with me. I don't care if you remove your uniform or not, but if your uniform is wet while you do the other chores, I will have to punish you."

I nodded and removed my uniform and got into the shower with her.

I was naked, other than the chastity cage as I got in the shower. I started to run her back and lather her up.

"This is very different from what we were used to in the shower huh" she said while giggling.

I said "Yes Miss Lauren".

"You had fun today didn't you? Tell me more" she said as I started to rinse her back.

"It was soo humiliating but also so much fun. I loved shopping for lingerie to wear and I was scared that Erica knew but she didn't say anything mean or humiliating" I said as I felt my voice get excited. Despite everything, I really loved today.

She giggled. "She didn't say anything for now! Maybe I should call the girls over for brunch by the pool tomorrow. We'd love to have a maid take care of us personally while we make fun of her and humiliate her for our benefit."

I whimpered at the thought of serving her friends and said "Yes Miss Lauren." as she got off the shower and put her arms and legs in front of her.

I toweled her dry and wiped my face of the excess moisture without realizing I wiped or smeared my make up. I gasped in horror and she realized.

"Uh oh. Since I gave you time to do your makeup, and you ruined it, I have no choice but to punish you silly sissy maid!"

I started to protest

"But but you asked me to help you in the shower!" I said while she wagged her finger at me.

"I don't care. Either you put your makeup on in 10 seconds or you accept a punishment. "

My makeup was on the other side of the room. There was no way I'd get to it in time. I nodded somberly and said "I'll accept the punishment."

"Very well. I think naughty maids like you need to be taught a lesson. Bend over my knee" she said as she went over to the bed and sat down.

I bent over her knee as told. Within minutes I found myself wincing as I felt her hand come down on my butt multiple times. The pain was quite bad and I felt myself on the brink of tears. I got up and found my bottom to be quite sore.

"Okay. I do not want to be running late. Help me get dressed!" She said as she stood naked next to the mirror.

She laid out her hands as if waiting for me to fix her bra. I took her brand new satin red bra and put it on her.

"This must be really different for you? You used to be the one who would take my underwear off. Now you're putting them on for me so another, better man can take it off! My, how the tables turn!" she said as she giggled.

Her panties were next and she had chosen a matching thong. I laid the panties on her feet as she put her legs through one at a time and waited for me to pull them up her smooth legs.

"I think we both know this is the closest you'll get to my pussy in a while!" She said teasingly as she adjusted the waistband of the thong and pointed me towards the dress.

The rest of the time was spent in helping her put her dress and make up on. When she was finally ready, right before she made me call her Uber, she got out a box.

"Now Samantha, since I'm leaving you alone and getting some real dick tonight, I didn't want you to feel left out so I got some gifts for you! Now dont get me wrong, I'm not unlocking you, but if you get bored or horny tonight and want something to do, I have a few things. You may open the box." She said as she handed it to me.

I opened the box to find a pink bejewelled butt plug, a bottle of anal lubricant, an anal enema bulb and a pink silicone penis shaped dildo. I looked at her as she continued.

"Like the gifts? I just want you to also know how good dick feels. From now on, unless I say so I want you plugged and cleaned every day. You can start tomorrow, unless you want to tonight! The line should help make your hole wet, and lastly the dildo, well that's for you! It's up to you if you want to go right ahead and bounce on it, while you think of how I'm going to bounce on a bigger cock tonight, or maybe you want to give it a little blowjob? Either way I don't want you to think I'm not thinking of you! That's a lie, I don't give a shit about what you do while my back is being blown out. " She said as her giggle turned into a vicious laugh.

"Thank you Mistress" I said as I graciously accepted the gifts before calling her an Uber.

As she left the house she said "Don't wait up for me! And make sure all the chores get done! Thanks Samantha!" as she left me alone.

I glanced at the clock. It was around 8pm. I decided to get busy and start doing the chores, simple things like laundry and dishes. As I started to work on them however, my mind kept going back to Lauren and her date. I couldn't help but think how she'd act with another man, how she'd flirt and obviously what they would get up to after the date. From Lauren's teases, I expected her to go all the way with this new man who I knew nothing about, not even how they met! But in some weird twisted way, it felt right to me. I guess I couldn't give her the thing she wanted, and me playing dress up did not help at all, which made this the most logical outcome. Besides, I was enjoying myself, albeit begrudgingly at some parts.

I glanced at the clock and saw the clock strike half past nine. It had only been slightly more than an hour. My mind kept wandering to her date. Were they done with dinner? Did they even eat dinner? What if they just said "fuck it, take me home and rail me instead.". I started to feel sick thinking of all the possibilities, yet I was extremely turned on.

I was still caged from yesterday, and apart from some major straining this morning, my penis hadn't been used at all, making it's absence feel more profound which in turn helped reinforce my femininity. Out of boredom and what could only be insanity, I looked at the dildo. It looked to be about 6 inches. I could only think of one thing looking at it, and it was Lauren getting fucked by it. Curiosity got the better of me and I started to touch it. It felt weighty and flesh-like despite being made of silicone. The more I looked at it, the more I thought there was no way it would fit inside me. But more importantly, why did I want it? I wasn't gay! I didn't want to be fucked. I think.

I turned my attention to the buttplug. It was pink, round and bejeweled. The end was tapered and the base was flared. This was something I could definitely insert. I hesitated but something in me snapped and I decided to lube it up. I pulled my panties down and bent slightly to allow it to enter my body. Being made of metal, it was cold as fuck but as it inserted itself it got warmer. As I felt my hole expand to take the butt plug, I moaned. It hurt ever so slightly but felt better after a bit. I walked around with it it on and loved the new sensation. I was just about to remove it when I heard the door click. I hurriedly put my panties back on and run to my room just in case Lauren divided to bring someone over.

Lauren entered alone however. It was only around 10pm? I took a look at her, while her hair was slightly messy and her make up was runny, she seemed fine. On second glance it looked like she had been crying. She went straight up to the bedroom. On suspicion of the latter, I went up to her bedroom and hovered around her door.

She was crying. While she wasn't openly bawling or weeping, she was crying softly.

"You don't need to stand there like an idiot. You can come in if you want" she said before adding "In case you were wondering, I didn't sleep with him. I know it's easy for you to slip a thing between your ass cheeks and act like a pansy sissy but it's harder for me okay?" She said while sniffling.

I was stung by her words. I didn't mean my fantasies and my desires to hurt her like this. The defensive part of me started to think things like "Well, we both agreed to this" and "Our marriage was getting stale" but the other part of my mind just felt guilty.

I sat down near her bed. "I'm sorry. I didn't mean to hurt you. We can go back to our regular life." I said.

Lauren looked at me with her eyes wide open as if the anger had only increased.

"No no no no. I don't think we can go back. I think we are already too far gone. You look like a cock drunk bimbo, and you expect me to accept that and go back? I'm sorry but I just can't think of you as a man anymore. That's probably what you wanted anyway. " She said before breaking down in tears.

I sidled closer to her and held her.

"I'm sorry Lauren. I didn't know what I was getting us into. It's not been easy for me either. Thinking of you with other men, being jealous, and almost sick to my stomach. I'm sorry I put you through this. I understand if you think we should separate" I said before tearing up myself.

Lauren snickered. "You idiot. I love you. Despite all this. And I do like this. The power over you, the freedom, it's very.. liberating. I just think I wasn't ready for the full real thing yet with another real man. I do want to do this. Do you want to continue?" She asked me.

"Yes. It's weird and I feel mixed but when it's humiliating I feel so turned on. I'm very lucky to have you who wants to play with me this way." I said.

"Good. I think we just need to go a little slower. " Lauren said before wiping her face finally. "Now, come here " she said as she kissed me.

We kissed for a while, almost like nothing ever changed between us before she broke the kiss and started to untie my top, leaving my chest bare. She started to kiss my neck and then moved to my nipples, slowly sucking on them like they were real breasts. I moaned slightly before she lightly bit my nipple.

"You like that don't you slut? Here help me get out of this dress and lingerie" she said as I helped undress her as she undressed me before we were both naked on the bed.

"Oh my God! I can't believe you're actually wearing the butt plug? Doesn't it feel good? To have your sissy hole filled up? " She said as she clapped her hands excitedly.

"Yes Miss Lauren" I replied as I was once again aware of not only how exposed I was but also how full my hole felt.

She pushed me onto the bed and continued to lay her perfect nude form on me while playing with my nipples.

My caged cock felt like it was about to explode. She clearly sensed this as she turned her attention downwards and started to leave a trail of kisses till she got to my caged cock.

She held it in her hands before commenting "Such a cute little thing! It's not a cock though. More like a cocklette? Or a clitty? Yes, I like that. Lil clitty! Does my sissy maid want me to go down on her little clitty?" She said changing the tone of her voice back to being demeaning.

"Yes Miss Lauren" I replied, my voice trembling with anticipation.

"Might as well. Oh by the way. I didn't not do anything with him. I did suck him off, and god was his cock perfect. Compared to your little thing, really makes me feel like I'm going down on a girl!" She said giggling before taking my plastic encased clitty in her mouth.

She sucked on it a few times, trying to mimic a blowjob before stopping and using her tongue to tease the slightly exposed tip. I continued to moan and writhe in pleasure before she suddenly stopped.

"I think that's enough for you today. Now, Samantha. Do you want to do me a favor and fuck my brains out?" She said as she got over to the other side of the bed on all fours and spread her legs, jutting her butt out giving me a good look at her tight wet feminine folds.

"Yes Miss Lauren!" I said as I jumped up ready to be unlocked running over to her hoping she would unlock me.