"Maid" to be a Cuckold Pt. 02

"That's a very nice offer Mistress. If Lauren allows, I would love to be besties. You're a great person, and you've been nothing but kind to me, even though you were a little mean. " I said unsure of where the brutal honesty was coming from. Perhaps I was letting my guard down?

"It's not being mean, it's being dominant. There's a difference. It's not the same. If I was really being mean, we'd have a different conversation. But we don't have to worry about that. For now, I just want you to relax and be happy. You wanna know something?" She said as I could feel her get up and come closer to me, her naked body on mine as she held my hips.

"I've had a crush on you for a long time, but I knew Lauren for years and would never steal her man. After seeing you like this, I'm sorry to say my crush went away. After all, I know I said you're a real man, but unfortunately the thing between your legs isn't going to cut it for me." She said as my heart broke.

Erica was a stunner, and I can't believe she had a crush on me for the longest time. It was probably all moot now. I tried my best to hold back tears.

Erica could sense this.

"Aww don't cry." She said still holding my nude form to her perfect naked body.

"I mean it's not completely useless. It's cute! She said as I was suddenly aware that she wasn't beside me anymore but had moved below me and her face felt really close to my caged clit, blowing on it as she was teasing me.

"I can't help but look at it, it's so cute. I wonder, have you ever had someone lick it? Or maybe had Lauren lick it? I know i'd like to, just out of curiosity. I mean Lauren has before just not this way. Although, did it really get big? I doubt it. I could probably fit the whole thing in my mouth." She said with a giggle.

"Uh thank you mistress." I said.

"Oh sorry. I didn't mean I was going to! Just that I could! Anyways, back to us. Yes, I did have a crush on you, and in some ways I still do. But I don't think you'll ever satisfy me the way I thought. But now, we can be friends. Best friends! But, I still have needs. And it would make me so happy if you would let me use you." She said before I could even process her words.

"How would you like to use me Mistress?" I asked nervously.

"Oh silly sissy, not in the way you think. Let's not ruin the friendship, besides, you're not ready for that yet. Maybe when Lauren gives the okay, I'll take you. But, for now, if I was in a mood, and my boyfriend couldn't satisfy me, could I maybe borrow your mouth?"

I didn't know how to respond.

"What would you need my mouth for Mistress?" I asked as if I was dumb.

"You're so silly, what do you think I'd use your mouth for? Silly girl. Do I need to draw a diagram? Maybe that's what I should do. Give you a diagram showing how a pussy and mouth go together, so you can lick it." She said with a little more command in her voice.

"I'd love to use my mouth for you, Mistress. I would do anything for you. But would Lauren allow it?" I said with genuine concern.

"Oh don't worry about that. If the time comes, she will. We've discussed things and if she decides she wants you to be shared, well. Let's not get ahead of ourselves. Besides, right now, we can have some fun. How about, you get on your knees. You know, just in case" she said.

"Yes Mistress. Should I remove the blindfold?" I asked hoping that after the massage and the honest conversation, I could at least see her naked.

"Hmm, no. I like it on. It's a little sexy. Besides, it's fun seeing you struggle a bit. I don't want you to see the girls, I want you to hear and feel. You'll like it better, trust me" she said as she pulled my hair back and moved my head forward until it touched her pussy.

"I'm going to sit down here and you're going to lick. You'll start at the top and work your way down, and then repeat. Okay?" She said as she sat on the edge of the lounger.

"Yes Mistress."

I did as I was told, licking the top of her pussy. I was amazed at how soft and smooth it was, and the way it tasted, so sweet.

"Mmmm, that's a good sissy. Good job. Keep going" she said as I felt her hand on my head.

I continued licking, not wanting to disappoint her.

"Oh god, I've never had a sissy do this before. Fuck, keep going. I'll let you know if I want to change things up" she said as her grip got tighter, pulling my hair back.

"Fuck, don't stop. You're so good at this. Does Lauren know how good you are? No, don't talk. Keep licking." She moaned.

I could feel the heat and the wetness from her pussy grow as I licked, trying not to drool. I was still blindfolded.

"You're such a good girl. Oh, this feels so good. I'm almost there" she said as she started breathing faster.

"Oh, I'm so close, keep licking, please" she begged as she grinded her pussy on my face.

With a couple more licks, I felt her shudder and cum.

"FUCK! YESSS!" She screamed.

"That was amazing. You did a good job. I've never had someone lick me like that, man or woman. Wow. " She said as her voice got back to normal.

"Thank you Mistress" I said, feeling proud of myself.

Erica guided me back out where I was still blindfolded, but could now feel the sun on my skin.

"So. How was your massage?" Said Liz.

"Oh my God so good. She really uh knows her way around" Erica said.

"Girl you glowing like you got your pussy ate" Vanessa said.

Erica just giggled.

"Well, hope you enjoyed it. There's no way I'm letting that sissy near my genitals!" Vanessa said before cackling loudly.

I felt someone pull on my arm. "Can you rub sunscreen on me Samantha? I don't want to burn" I heard Courtney's voice.

"Yes Miss Courtney. I'd be happy to" I said.

"Here. Let me guide you. Don't worry. Im not going to make you walk into the pool." She said as I walked towards her, holding her hand.She made me sit down in front of her or at least it felt that way, as she guided my hands to her legs.

I started to rub the sunscreen on her legs, and worked my way up. I couldn't help but feel what I thought was her bare pussy, near her upper thighs. The thought of licking it came into my head, which shocked me. Why would I want to lick her pussy? Wouldn't I want to fuck it instead? Was it because I had just licked Erica?

My thoughts were interrupted when she suddenly slapped me gently.

"You're supposed to be rubbing lotion on me not drooling over my pussy you perv! Get your hands to work! And no, you can't lick or finger it. Not yet" she said sternly as if reading my mind.

"I'm sorry, Miss Courtney. It's not what you think" I said as I started to work on the sunscreen on her legs again.

"Oh yeah, what's that? Is your clitty getting hard? Don't lie to me. I see you twitching in your cage, don't forget I can see you naked even if you can't see me! Just for that, you're going to massage my feet after you're done." She said as her voice lowered to a sultry whisper.

"Yes Miss Courtney." I said obediently.

"Wow Court, I didn't know you had a mean streak!" Erica said from beside her. Was she in a lounge chair too?

"You're just jealous. I got the maid's attention now. Not all of us can have our own maid and command her!" Courtney said as her voice got more relaxed, presumably due to my massage.

"Yeah, that's not the only reason. It's because she's not your maid. She's mine. And I'm lending her out to all of you. Isn't that right Samantha?" Lauren asked me.

"Yes, Miss Lauren. I'm at your service, all of your service. "I said as obedient as I could.

"Good. Now, finish up with Courtney. The rest of us are going swimming, rather skinny dipping. You can think of our wet naked bodies and us splashing around in them while you sit there blindfolded. Oh and don't touch yourself, it is unbecoming of a maid." Lauren said.

"Yes Mistress" I replied as the angst started to fill my body. With a couple more rubs, Courtney signalled I was done by tapping me on my shoulder.

"Thank you, Samantha. You can sit by my side. " She said as she held my hand and guided me.

"Do you want to massage my feet?" she said as she lifted them and placed them in my lap.

"Yes, Miss Courtney" I said.

Her feet were smooth and soft. While her nails felt long and pointed, it wasn't too hard to massage them.

As I massaged, I could hear the other girls squeal, scream and giggle in delight, obviously playing and splashing. I imagined what was going on and got even harder. My clitty started to get painful.

"Hey sissy. Are you getting hard? Are you getting distracted?" Courtney asked me.

"I'm sorry, Miss. The shouts from the pool distracted me. I'll try to focus." I said.

"That's alright. Here, let me give you something to help you." she said, as I felt her place a glass in my hand.

"You know what this is don't you? " She asked.

"It's a glass, Miss Courtney."

"No duh, and can you smell it?"

I brought the glass to my nose and inhaled. "It's vodka, Miss Courtney."

"Good girl. Drink it." She said as I felt her voice closer to my ear.

I hesitated, as I imagined Lauren would not want me to be drunk on the job.

"I said drink it!" She demanded.

"Yes, Miss Courtney" I said.

I drank the glass down, feeling the cool liquid run through my throat.

"Good. Now another" she said as she filled the glass and put it back into my hand.

"Yes, Miss Courtney. Can I ask you a question?" I said as I could feel the vodka giving me courage.

"Sure. I guess it's the least I can do for your excellent service so far." Courtney said as I could feel her relax in her chair.

I drank the whole glass again before she filled the glass up again.

"How do you like my new look, Miss Courtney?"

"Well. It's different. I've never seen you naked before, and after today I don't think I want to. It's a lot of fun. You're actually weirdly sexy in a weird way. Now don't get me wrong, you will never fuck me. At least not in the way you think. It's crazy to think about the fact that you used to have a dick, and now, well. You're a sissy maid. What do you think about your new look?" She asked.

"I love it so much. It's weird and humiliating. But the more I do this, the more I love it. I asked Miss Lauren for this. It's hard not to be turned on by all this. It's really liberating in a strange way. All this humiliation I mean." I said as I could feel tears in my eyes again.

"You like it huh? Well, the humiliation part is just the beginning. We've all been talking, me and Lauren and the girls. You're not a man. You're not even a boy. You're a lesser girl. A sissy, a bitch. A worthless little cuck. We've also been wondering, if you want to keep doing this. Maybe we can all have some more fun?" She asked.

"What do you mean Miss Courtney?" I replied.

"Well. Your wife is really hot. So are me and my hubby. And while your penis is cute and tiny, you're kind of useless from a sexual perspective. Maybe, if you're a good sissy maid, maybe one day, we can have some fun. You and me. While my husband fucks your wife. Because you would like that, wouldn't you? Seeing your own wife being taken by a bigger better man. And trust me he's bigger, better than you ever were when you were a man" she said pausing.

As I was still blindfolded, it felt like my other senses were heightened. I could feel her breath getting shallower.

"You can't wait to see him take her in every position she wants. Positions you could never achieve. He would have her at her mercy. She'd be his little slut.But that's not the best part, is it?" She said.

"What's the best part?" I asked as I felt my breath become shallower too.

"I'll get to that. Patience my slutty friend. Then, when he's done with her, he can come and fuck me and you can watch me in the throes of ecstacy. And that's when it'll click for you won't it. " she said as I felt her whisper.

" Ask me what will click for you?" Her voice said.

"What will click for me Miss Courtney?"

"That the pleasure you've been seeking is not what Mark has or what he gets. It's what me and Lauren get. You don't want to be the man anymore. You weren't good at it anyway. You want to be the woman. You may not admit it now, or later but you want to be one of the girls. In every way. Including being fucked like one. You want to experience pleasure the way we do. It makes sense doesn't it?" She said as I squirmed.

I thought about what she was saying. It made sense. In a weird twisted way. It echoed back to what Liz said the other night, how sissies view themselves as male failures and thus envy women.

She sensed my squirming.

"Aww. Are you getting wet thinking about it? Me too girl. Me too. Here, let me see!" She said as I felt her fingers on my caged clit. I gasped as her deft hands cupped my balls and clit. I could feel her fingers on the opening of my cage, playing with it like a real woman's clit.

"Aww. That's such a cute clit. And look how it drips like one too! Anyways, where were we." She said as she continued to run and play with my caged clit.

"About how Mark will fuck me." I said as I felt tiny waves of pleasure run through me with every touch of her fingers.

"Oh no no. We didn't get that far ahead. Patience my slutty girlfriend. We were talking about how it makes sense. How it all makes sense. You, me, Lauren, Mark. Hell, even Erica, and Liz and Vanessa. You've realized your place haven't you. You're not a man, never was. You're more like the girls. Vanessa may disagree but to me, you're just another girl. I'm even playing with your clit like how I played with Laurens. " Courtney said.

What! Did she just admit to sleeping with my wife? I knew Lauren experimented with girls in college, and Courtney and her did go way back but I never expected this.

My mouth must have been open because Courtney could sense it. Well, let's be honest she wasn't blindfolded, I was! So she probably saw the shock on my face. She continued to play with my clit, rubbing it and flicking the tip.

"That's right. I've slept with Lauren. It was before you though. And unlike you, I can say I've seen her real moans, shit I probably made her moan louder than you've ever tried. Would you like to know how I did it?" Courtney said as she moved one of her fingers to the space between my butthole and my balls.

"Y-yes" I managed to say.

"Not just yet. Now, where were we? Ah yes. Getting fucked. You want it. You know you want it. Because that's what you really really want isn't it? To feel like a woman, to feel like a slut, to scream in pleasure from the best orgasm of your life. " She said as she moved one hand to my bare nipples pinching them before moving the other finger inside my butthole. I moaned.

"You have such a tight pussy. Just like your wife. This is exactly how I made her scream that night in college. But let's not get distracted. Back to Mark. Just think. He probably wants to cum in your wife. Thick loads that you will clean up. Because you are a cum slut too aren't you? Lauren truly is lucky to have someone like you. And maybe after she gets hers and I get mine, I'll want my way with you too. I know you'd love to lick this pussy. You're practically drooling already aren't you. I saw what you did to Erica. I know it was supposed to be your and hers little secret but I saw you. " She said as she paused.

I was getting more and more worked up. Her finger seemed to move occasionally, almost like she was fingering a real woman's pussy. I felt a shiver. Was I getting close to an orgasm?

Courtney continued. "But more than pussy you want his cock. You're so wet thinking about it. I can feel it. But my husband only fucks good girls. You'd love to be a good girl for us all wouldn't you? You would like that wouldn't you?"

"I'd like that Miss Courtney. I'd like to get fucked by a real man." I said trembling in fear, humiliation and sheer horniness as I could feel the orgasm build higher and higher.

"Oh but it isn't that simple my slut. You see, me and your wife need to be satisfied. If after all that, Mark still has some strength left over, and God knows he does, because he is a true specimen after all, then just like eating our creampies as leftovers, you can get fucked by him." She said as I continued to squirm.

"As Lauren and I lay out on the bed, our tight holes ravaged by his large dick, and trust me, no matter how much it stretches me out, I will always be tight enough for him, you lay there in your cage and your pretty little butt plug just wondering if he can make you feel the same. He can, but should we let you?" She asked as she stopped fingering and playing with my caged clit.

"Fuck. Yes. Please." I said not knowing and not caring what I was begging for.

"Oh no no. I need more than that. Beg. Beg for my husband to fuck your wife and you. Explain to me why he needs to do so." She said as she put her finger back inside me and moved it faster, while her thumb moved around the tip of my clit, causing me to squeak in pleasure. She was teasing me. Expertly. And I was falling for it. Hard.

"Miss Courtney. I can't satisfy my wife. I'm just a sissy cuck. She needs a bigger better man. She needs someone like your husband. Please Miss Courtney, can your husband fuck my wife and mistress? And if I've been a good girl, can he fuck me too? Please please please" I said.

"Sure" was all she said as she continued to finger me. "And I'm sure that's not all you want, you want to cum today don't you? Cum like a pretty little girl with my finger in your pussy and me rubbing your clit?"

"Oh god, Mistress, it feels so good. I'm so close. Please mistress. Can I cum?" I asked as my head swam in pleasure. I was high on my own horniness, unaware of how humiliating the situation was. One of my wife's hot best friends was in her birthday suit, with her finger in my ass, and was talking to me like I was a girl, I was blindfolded, locked in chastity and begging her for anything resembling release.

"I know, you're going to cum so hard. And you're going to thank me after." She said not letting up.

"Yes, Mistress, I'm going to cum. Oh god." Was all I could muster.

"Are you going to cum, sissy slut? You can't until I say so. " She said trying her best to tease this out.

"Yes, Mistress. I'm going to cum. Please, let me cum. I need to cum." I said.

"Beg for it. Beg for permission to cum." She replied.

"Please, Mistress. Please, let me cum. I'm so close. I'm going to cum. Please, please, please." I said almost shouting. I had no idea where the other girls were, but at that moment I didn't think I cared.

"I don't know. Should I let you cum, Samantha?" She said. Fuck! She was an expert!

"Please, Mistress. I'll be your good girl. I'll do anything. Please, let me cum. I need to cum."I said as I couldn't take it anymore.

"Okay, cum for me, sissy slut. Cum for me." She responded.

I immediately squirted cum from my caged clit and felt Courtney's hand under my balls as if she was collecting it all.

"Oh god, oh god. Yes, Mistress. I'm cumming. Oh god." I said as I squirted jizz from my caged clit.

"That's a good girl. Cum for me, sissy slut. Cum for me." She said as her hand remained under my balls collecting all the pent up jizz.

"Yes, Mistress. I'm cumming. Oh god. Thank you, Mistress. Thank you." I said as the high started to leave my body.

"You're welcome. Now, since I've been so kind, and have been so very generous, let me give you a reward. Your own cum. You can lick it off my hand." She said.

"Yes, Miss Courtney." I said, as I accepted my fate and the high of the orgasm started to die down.

"You're welcome, sissy slut. Oh hey Lauren!" She said, very matter of fact.

Fuck!

"WHAT THE FUCK!" Lauren said as I felt her presence.

"We were just having a little fun. " Courtney said

"Oh, is that so? Well, you can have as much fun as you want Court, I don't mind that. But what about our little maid here?" Lauren asked.