"Maid" to be a Cuckold Pt. 02

DISCLAIMER: The following story contains mild to heavy humiliation and the protagonist may be blindfolded for a period of time. Please consider this a trigger warning for claustrophobia.

*****

I woke up the next morning to my alarm ringing. I had a slight headache from all the crying and frustration of last night and was a little sore from the "sex". After showering, I got ready in my maid's uniform and make up and headed downstairs to the kitchen to make breakfast.

At 8 o'clock, Lauren was waiting, naked.

"Good morning Miss Lauren." I said.

"Good morning" she replied, with a tone which seemed quite satisfied.

"Are you ready for some fun today? You'll have plenty of chores to do around the house and the garden, and I've invited the girls over for lunch by the pool. But before that I have a challenge for you" she said as she poured out her coffee.

"Yes, Miss Lauren. Do you want me to prepare your breakfast?" Was that the challenge? What was she talking about?

"Yes, and I will take a fruit bowl. As for your challenge. It's very simple. Since the girls are coming over for a pool day, we're all going to be in bikinis all day. I want a new one. A sexy one for my new sexy confident self. And you're going to buy me one. " She began as she sipped her coffee.

"But here's the catch. You're going to the store to pick a bikini for me. But it can't be just any bikini. It has to be a bikini you think will be sexy and look good on me, and it has to fit me. I will not tell you any of my size specifics. You'll have to guess it on your own. If you come back with a bikini and I like it and it fits me then great. If not, then well, I guess I'll just have to be naked now won't I? Yes, butt naked. You're lucky it's just the girls. For now. What if one of their husbands or boyfriends come over? " She winked.

I nodded, unsure of the challenge, but knowing full well if I didn't succeed, not only would my wife be naked but the embarrassment of knowing the other women and their lovers would potentially see her like that would be unbearable.

"Oh and, one more thing. You're going to be in the same bikini under your maid uniform. Makeup and all. So you can have a little taste of how I might have to spend my day" She said.

"Yes Mistress" I said as I prepared her a plate of fruits and brought it to her.

"Thank you Samantha. Now run along and buy the bikini. You have maybe an hour. You're on the clock" she said as she looked at her watch.

I got ready and raced to the car, not wanting to fail this test. I found a small boutique, and while it didn't have a large selection, the ones they had were all the modern sexy two piece styles. I started with the smaller sizes, and while they were cute, the top part looked a little loose.

I myself was in complete femme mode as Lauren requested. I had become more comfortable with dressing as a girl outside, besides this boutique was a complete new place for me.

I tried my best to figure out her size from just the garments. I explained to the sales girls how Lauren looked and hoped they could help me figure this out. But it didn't seem to work.

"Without a size or even numbers it's hard to get the exact fit! And we are a boutique. We don't do random sizes like M or S, we try to cater to specific numbers" the salesgirl said to me.

The other salesgirls all tried their best to help, but I had to pick a bikini just by the numbers. How could I she be a 32, 36 and 26? What did those numbers even mean? One of the salesgirls was even kind enough to show me her breasts and told me what a 34D meant.

Ultimately I picked something for Lauren that I thought fit her perfectly, and a bikini that looked similar for myself, the only difference being the size. After paying for both the bikinis, I got back into the car, and made my way back home.

I tidied up the pool area, made snacks and drinks for the ladies. In almost no time, the hour of the party arrived.

"Omg they're coming! Samantha you better go greet every guest and lead them to the pool! I'm not ready yet. Tell them I'll be there soon, and make sure they're comfortable! Oh and you better be in your maids uniform while doing so!" Lauren said through her bedroom.

One by one the bell started to ring. I gulped as I put on my uniform. The first to show up was Erica, she had already seen me like this, so I felt a little better.

"Hi Samantha! You look so cute in your maids uniform! " She said as she pecked my cheek.

"Can I get you anything Miss Erica?" I said not knowing what the correct honorific would be.

"Just water. Thanks" she said as I went to fetch her water.

Next was Liz and her wife Vanessa. Vanessa was a gorgeous black woman with long hair, a perfect ass, and perky breasts She was a professional model and looked absolutely stunning.

With her was Liz, who had already seen me in my new femme avatar.

"Hello Samantha!" She said warmly. Vanessa on the other hand just snickered.

Last but not least was Courtney, the last one of the girl gang. She was married to her husband Mark. She had a nice round ass and had ginger curls. She was always really kind to me but today she looked to have a mean streak.

"Hey sissy, your wife says we're going to get served by you today" she said as she laughed and pointed towards my crotch. I felt my face burn red in shame.

The girls made their way to the pool, as did I, following them and serving any drinks or beverages they wanted. Once the girls were all there, Lauren came out.

"Hi girls! I hope you're comfortable, because you will be for the next few hours" She said as she got down to the pool area. She was wearing just a robe. Was she wearing her bikini under there?

"I've got a treat for you girls! And Samantha is a part of it too! Are you ready to see my new look? And are you girls okay with that? " Lauren asked, her voice filled with excitement.

The girls were curious. "Of course! Is this the new bikini you told us about?" Liz said.

"Sorta. Samantha, can you please come here?" She said, her eyes glimmering.

"Yes, Miss Lauren. Do you want me to get you something? " I asked as I pottered towards her.

"Yes, can you please untie my robe? I want the girls to see what I'm wearing." She said as she winked at me.

"Of course, Miss Lauren. Anything you wish" I said as I slowly undid her robe.

To my shock, she was naked underneath. My heart sank as I realized I failed her challenge, and her body was now on display for the other girls.

Lauren saw my expression. "Don't worry honey. I knew you'd fail. Girls, do you like my new look? " She said as she looked around to her friends.

The girls were quiet at first before Liz clapped and cheered. The other girls followed suit.

"Wow. You look wow. I think more than anything, it's the confidence, because your body has always been banging but that newfound confidence makes it so sexy" Said Courtney.

"I love the look, I'm sorry honey but she's really hot. I can't look away!" Said Vanessa to Liz as Liz ribbed her.

"I'm curious. What was the challenge? Not that I mind the nudity." Liz said.

Lauren smiled, "Well the challenge was, she was supposed to pick out a bikini that would fit me and look good on me, without knowing any of my measurements. If she did, I would wear it, and if she didn't, she had to go naked. So, I tried it on and it was just a little too tight. I mean it was almost there. " She said with a wink as she twirled around showing off her naked body.

"Wow. You just keep acing the challenges, don't you! You're a natural domme, and that's clearly affecting the way you carry your body too! Love it!" Liz said enthusiastically.

"I love all of this. I really do and I know Samantha does too. It's such a confidence boost, and I didn't realize how much it helped until today. I've been wanting to do this for a long time, and I think the fact that my pathetic husband is now a sissy maid, is the kickstart I needed" she said as the girls cheered.

"You're so brave, and honestly so hot. I can't believe I'm seeing you naked, and yet I can't look away. You make it look so good I'm tempted to take off all my clothes!" said Erica.

"Well, at least that way we won't get tan lines. Bikini tan lines are the worst. My husband does not like them" said Courtney.

"Yeah well, your husband isn't here is he. I'm sure he'd be happy to see what you're seeing. Or maybe I can send him pictures?" Lauren said giggling as she posed her nude body suggestively as if Courtney was taking pics for her husband.

"I don't care what you do. He's been asking for a threesome anyway" Courtney said with a wink.

"Oh. So your hubby likes that does he? Well. Maybe we can talk about that later. For now, let's drink!" She said as she grabbed a glass and raised it.

The girls followed her and raised their glasses before getting more comfortable and their bikinis. I was serving the food and drinks as needed.

At some point, Erica and Courtney had removed their tops but we're laying on their backs, their breasts hidden from me. They were topless, just like Lauren. I tried my best not to stare at their bare sideboobs as my cock or clit twitched in its cage.

"Samantha, since you're our maid, you need to address us each the way we want to be addressed. I see you've been calling everyone Miss, but what if they don't like that?" Lauren said as she put her sunglasses on with a smirk and got comfortable on her lounge chair.

"Yes, Miss Lauren. I didn't know, can you tell me how they want to be addressed" I said, hoping it wasn't a trap.

"Why yes. Erica here prefers "Mistress". Isn't that right Erica?" She asked.

"Yup." said Erica.

"Courtney, is "Miss" good for you?" Lauren asked.

"Hmm. I do prefer Mistress. But I'm not picky." Said Courtney.

"That's fine, just address her the same way you'd address me, or call her whatever she asks you to" Lauren said, before continuing, "as for Liz, well, I've always thought she should command more respect. She is a doctor after all. So you will call her madam doctor or doctor. Now Vanessa, what do you prefer. "

Vanessa hadn't said anything to me. Without even looking in my direction. She giggled and said "Goddess."

"Yes. Goddess. You'll call Vanessa, goddess. She looks like a goddess, so she does deserve it" Lauren said, laughing as Vanessa smiled.

"I know you've been calling me Miss Lauren, but you can switch it up with mistress every now and then. I don't mind. I own your ass anyway " Lauren added with a vicious laugh.

" Now, if you will excuse me, I'm going to lie on the sun lounger and sunbathe. Samantha, can you come and slather me with sun lotion. I would hate to burn my naked body" she said as she stood up.

"Yes, Miss Lauren. " I replied.

The other girls seemed a little jealous, knowing that Lauren had her personal attendant personally rub her body with sun screen.

"You know. You girls don't know what you're missing out on. Sunbathing nude is just really freeing." Lauren said as I applied her sun lotion.

"Yes. Why not. We're all adults and women here." Said Courtney, who was already topless and now wriggled out of her bikini bottoms revealing her smooth bare ass.

Erica went next. She pulled her bottoms off, and turned around, her breasts were perfect and her nipples were rock hard, she kept her hands on her pussy as if covering from me.

"Uh uh. I'm m not taking my clothes off. This is as far as it goes" said Vanessa. "Not in front of the sissy. I feel gross. I know we say she's one of the girls and all but she was a man. Or used to be" Vanessa said looking at my direction disapprovingly.

"Aww, Vanessa. It's okay. Don't worry. You don't need to feel awkward or bad" Lauren said reassuringly.

Vanessa however was still not ready. "Y'all can get naked, but 'm not taking off my clothes not in front of the sissy." She said sounding adamant.

Liz was about to take her bikini off when she looked like she had an idea.

"I know. Samantha should join us. That way Vanessa can feel more comfortable once she realizes how harmless she is." Liz said.

"Good idea!" Courtney added. "After all, we're all girls here anyway." She said with an emphasis on the word "girls".

"Oh I love this. Samantha, take your clothes off. I want everyone to see my sissy slut." Lauren said excitedly.

"Yes Mistress" I replied, feeling nervous, as I took off my maids uniform.

I was now in just a bikini.

"Take it off sissy" Erica said as she looked at me.

I nodded and slowly took the top off, revealing my breasts and the clitty in my bikini bottoms. While I didn't expect shouts and cheers the way the other girls got, I got a few whistles and hoots that I later realized was laughter.

"It's like a tiny bulge. Oh my God Laur. How did you manage all these years?" Courtney remarked while giggling.

"That's not all, you haven't seen it yet!" Lauren said, "Take the bottoms off too. Let everyone see your whole body, including your sissy clit and pussy. God knows, I have had to deal with it for years" she said as she rolled her eyes.

"Yes Miss Lauren" I said shamefully as I took the bottoms off, leaving me totally naked in just my heels.

"Look at her in just the heels" Erica giggled. "Does the sissy feel powerful? Look at her, in her high heels, her sissy tits and clit. It's so weird thinking of her as your husband. Thank God you decided to pursue this lifestyle. I don't know what I would have done if my boyfriend was so tiny" she said.

"Well, you could always try mine. I'd happily show you how big dick feels " Courtney said laughing. This was the second reference she made to her husband. Was she trying to set Lauren up with her husband Mark?

"Maybe later. But now, let's take our minds off the sissy. So Vanessa, do you feel better knowing Samantha is naked, and you have nothing to worry about with her little clitty locked up? " Liz asked.

"I'm not sure, but I definitely feel better knowing she doesn't have a dick or a traditional one anyway. I guess I'll get naked. But" she started

"But what?" Lauren asked

"I guess I'll take off my bikini if we blindfold Samantha. I don't want her to see me naked. I worked hard on my body, and it doesn't make sense to waste it on sissies. What do you girls think?" Vanessa said.

"That's totally fair and a really good idea. We all work super hard on our bodies, makes sense only worthy people should see them! Sorry Samantha. Would you be okay with a blindfold, or would it make you too anxious? I know you don't like being blindfolded."Lauren asked being oddly considerate after all the humiliation she piled on so far.

"If you're all okay with it, then I would not mind Miss Lauren. If not, it's fine too" I said realizing I probably made no sense. All of this humiliation was making the blood flow to my head decline, making me feel lightheaded. I knew that while the humiliation was getting to me, being blindfolded would only make it more intense.

"We're okay with it." Liz said, speaking for the other girls.

"Okay. Samantha. Turn around. I'll take a towel and tie it around your eyes" Lauren said.

"Oh, don't use a towel. Use her own panties! I'm sure she's been leaking in them, it'll only add more humiliation if she has to imagine us naked but has to smell her own stinky pre cum!" Courtney added. Courtney was really shaping up to be a bitch today.

"I like the way you think! Come here Samantha" Lauren said as she took my panties and tied it around my head, blinding me completely.

"You can turn back around now." She said.

I did as I was told and turned around.

"You're such a good girl. Now, you may serve the girls while they enjoy their time and the sun. I know they will want you to do things for them. We will try out best to make sure you don't fall in the pool!" She added with a vicious giggle as all the girls joined her.

"Okay I'm naked!" Vanessa said as if announcing for my benefit as the other girls all cheered.

"Me too!" Said Liz as I heard the ruffle of clothes and giggles. I stood there naked, caged in heels with a group of gorgeous girls, also naked, and nothing I could do about it.

"Hey Lauren, I heard your sissy maid can do some good massages. Do you think I could borrow her for some er private massage time?" a voice asked, which I then recognized as Erica's. There was a emphasis on "private" for some reason.

"Oh sure. You and any of the girls can use her for anything you need, she's at our service after all!" Lauren said with a laugh.

"Okay great! Come with me Samantha, let's go over there by the shade where it's a little quieter." Erica said leading me by my hand. "You girls get your sun in, I'll come back in a bit!" She said with a almost sing song voice.

She led me to a lounge chair in a cooler shady area. My guess was it was the lounge chair in the pool cabana we had. I heard a zipper, as I realized she must have zipped up the cabana to give us privacy. What was she planning?

She led me to the lounge chair.

"I'm going to lay on my back and you can start massaging me. I'll guide your hand to my upper back and you can move down. But not too down. Not yet." She said as I nodded in agreement.

"Yes Miss Erica" I said.

"Oh and don't forget. When you're not addressing Lauren or Courtney, or Vanessa, you should call me Mistress. It makes me feel sexy. Sexier than miss anyway."

"Yes, Mistress Erica" I said as I started to massage her middle back.

"Can I tell you a secret Samantha? I know that you were a man. I know that you still think of yourself as a man. But deep down, I think you know the truth. You're a girl, and you're not just any girl. You're a sissy. A little slut. A whore. Aren't you?" She said.

"Yes mistress. I am just a sissy cuckold maid." I replied, as if resigned to my fate.

"Now, talk to me. Don't worry, no one else can hear you, the others are too far away and we're hidden in the shade. How does this all make you feel? Honestly. " She asked.

I was honestly a little more relaxed than earlier, apparently relaxed enough to answer her question candidly. It also felt good knowing, that despite all the humiliation the girls cared about me in some weird way.

"I'm embarrassed, but I also feel really good. My mind is in overdrive and yet somehow I feel calm. I never thought I'd feel like this. But the humiliation. I can't get enough. I know it's weird, but I'm starting to crave it. And not just verbal, but physical. It scares me a little. But it also excites me." I said.

"It's not weird. Trust me. This is how you're supposed to feel. We were made to feel good. And sometimes, we're taught not to. I'm honestly proud of you for owning up to what you want and telling Lauren what you want. Not many men are capable of doing that. And some might say, that's the real sign of a man. To know what he wants and ask for it. That's not just any man. That's a real man in my books, despite you know, your appearance." She said.

"Thank you Mistress." I said.

"I'll let you in on a secret. Lauren was never completely attracted to your male side. But you were always cute, and nice, and respectful. And that's why she started dating you." She said.

I gasped. It shouldn't have come as a surprise, but weirdly it did. Erica continued.

"The first time I saw you in your maid's outfit, it was like seeing a whole different person. And not just because you were wearing feminine clothes, you wore them to my store too remember? But the maids uniform really drove in my mind how you're a girl now. Almost. You were always kind of feminine. Now, you've blossomed. I've never met a sissy like you, or well a sissy at all really. And if Lauren and you decide to pursue this, I'd love to be a part of your journey. I'd love to be like a girlfriend to you. We could go shopping, we could talk about guys, we could have girl talk and watch movies together, I could help you explore your femininity. I'll be your bestie" She said as my hands moved to her lower hips.