The New Neighbor - Chapter 18 (Patreon)

The New Neighbor - Chapter 18

It was Saturday after my wrestling match and I was to be locked in chastity until Jane could post the keys. Kristina had asked me to serve her breakfast in bed, telling me that she had an idea for a ‘celebration’.

“So, Mistress, you said you were thinking of celebrating the end of our trial?” I asked as I knelt down beside the bed after handing her a tray of breakfast.

“I did. I was thinking we throw a little party in your honor, with Paulette the maid serving our guests.” Kristina said, watching intently to gauge my reaction.

“What? You mean I would be the maid…” I was a little panicked at the prospect of serving a house full of guests while fully feminized.

“Haha, that’s exactly what I mean. But don’t look so panicked, I’ll make sure the guests are all people you have interacted with over the last two weeks. Sam and Mel of course, they helped with your original transformation, Emma who you met recently and of course there’s no reason to be shy around her is there? haha.” Emma had apparently been the one who used my face while Mistress fucked me with her strap-on while I was blinded and bound.

“I guess not. Anyone else?” I asked.

“Well I’ll need to invite Cynthia, she did such a good job training you as a puppy after all. Then I could ask if Jane can make the trip over again. So, what do you think? Are you game?” She asked me. She had a point about the guest list, it wasn’t like a bunch of strangers I would be humiliating myself for. Hell, for a crowd like that, it would probably be a boring party. “Remember, Paul, you can say no if you think it’s too much. I’m sure I can think of another way to celebrate.”

“Actually….screw it. Let’s have the party.” I replied.

“Are you sure? My guests will no doubt be teasing you all night. Having fun with a sissy maid, sure you can handle a room full of dominant, teasing women?”

“Ha, after these last two weeks with you. I’m pretty sure I can handle anything. Let’s celebrate.”

Kristina looked delighted at my response and I was happy to know that I had made her smile. “Great! Now I’ve finished with my breakfast, it’s time for you to eat yours.” Kristina threw back the covers and parted her legs and I got the message. My cock throbbed in the cage as I crawled between Mistress’ legs and began my ‘breakfast’.

—

The rest of Saturday was spent doing household chores in preparation for Sunday's party. I was a little nervous about being the maid for a house filled with women, but I knew I would enjoy it and likely spend the whole day incredibly turned on. Kristina would probably be counting on that fact so she could put my pent up sexual energy to good use later on.

On Saturday evening, Kristina led me into the bondage room to get a special something ready. “Okay, slave, I have a fun surprise addition to your outfit for tomorrow, but it requires a little preparation.” Kristina strapped me face down over the bondage bench and grabbed a leather paddle. She then placed a laptop on a table in front of my face with an attached, high-end microphone.

 “I’m going to give you some phrases to repeat and I want you to say all of them as clearly and enthusiastically as you can, understood?”

“Yes, Mistress.”

“Good, then let’s begin. Read aloud what you see on the laptop screen.”

I looked at the screen as the first phrase was displayed. “I’m a good, sissy maid.” I read it clearly, but apparently not as enthusiastically as she wanted because she swung the paddle down hard on my pantied and plugged ass. ‘Crack!’

“Try again, sissy, more enthusiasm.” She said, readying the paddle again.

“I’m a good sissy, maid.” I repeated the phrase, trying to sound bubbly and excited this time.

“Much better, keep going. Here’s your next phrase.”

“My name is sissy Paulette, the pretty maid.” I blushed at hearing myself say the humiliating words, but I wasn’t spanked this time so I must have done an acceptable  job.

“I love having my little sissy clitty locked in a cage.” ‘Crack!’ “Ow! Sorry, Mistress.”

“This one is an important phrase, slut. Make sure you sound as happy as possible.” Kristina told me.

“I just loooove having my little sissy clitty locked in a cage!”

“Hahaha, much better! Next phrase….”

This continued for a while longer. Whenever I hesitated or didn’t sound as enthusiastic as Kristina wanted, I would be spanked hard with the paddle.

“Would you please spank my sissy butt for me?”

“Is there anything I could do to please you?”

“I exist only to serve.”

“Yes, Mistress.” 

“Of course, Mistress.”

“Thank you, Mistress.”

“It would be my pleasure, Mistress.”

“Good job, sissy. Just a few more.”

The next phrase caused me to hesitate a little as I read. “I just love having a big, thick cock up my- my sissy ass.” ‘Crack!’

“Try again, sissy.”

“I just love having a big, thick cock up my sissy ass!”

“Hahaha, much better. I think that one might be my favorite.”

“How may I be of service to you?”

“I no longer own my own dick.”

“My tiny, sissy clitty belongs in a cage.”

“Mistress owns my cock.”

“I love being spanked!”

“Please tease me.”

“I’m such a horny slut!”

“I love having big, bouncy tits.”

On and on the recordings went until I was finally finished and released from the bondage bench with a slightly sore ass. “Good, job, sissy. Now go ahead and shower and make sure there are no hairs anywhere below your neck. We want the full sissy experience for tomorrow.”

“Yes, Mistress.”

So I showered, shaved and that night I was allowed back in bed with Kristina with my desperate cock pulsing against the cage. On Sunday morning, we woke up early to begin my transformation.

We headed into the spare bedroom where the outfits and makeup table were kept. Kristina went right for the prosthetics that Sam and Mel had made for me. The large round prosthetic ass was pulled into place first. The false, foam pussy was pulled into place, replacing the small bulge of the tiny chastity cage with something more feminine. Then she pulled out the boobs.

The two, huge, jiggling breast forms were pulled down over my head and shuffled into place, I could immediately feel their added weight and blushed as I looked down at the alien sight of myself with huge breasts. 

“Looking good so far, but let’s get you dressed!” The bra and panties were first, a matching pink set with lace ruffles across the rear of the panties, far more feminine and frilly than most women would ever wear.

A garter belt was next with the straps threaded beneath the panties and clipped to a pair of sheer, pink stockings. Then she unveiled today's dress.

The main body of the outfit was primarily pink with white accents. It had a high collar that had a snap at the back of the neck, but there was a heart shaped cut out that would leave a large amount of cleavage on display. The collar would also serve to hide the seam of the breast plate. I blushed a deep red colour before I had even touched the dress. Just the sight of it was enough to embarrass me, let alone the thought of being seen by a room full of people.

“Wow, that’s….something.” I said.

“Haha, I know, beautiful, isn't it. Let’s get this on you.”

The dress was fastened onto me, zipped up in the back and snapped in place behind my neck. There were stiff petticoats sewn beneath the short hem, holding the dress outwards enough so that my stocking tops were almost exposed. Puffy, frilled shoulders were almost constantly in my peripheral vision.

“There, almost perfect. Quite an inviting cleavage too. Just need a little makeup and we’ll be good to go.”

A little makeup turned out to be a layer of foundation, smoky eyeshadow, mascara and some blush. I was surprised to find my lips untouched.

Kristina helped me into a pair of pink heels and gave me some time to get used to them. “Walk a few laps of this room to adjust in the heels. They’re not too high so should be okay before the first guests arrive. I just need to get one last thing prepared.”

She left me to get used to the heels and the altered centre of gravity, it felt like the boobs were bouncing too much and my fake bubble butt was constantly in danger of being exposed by the flouncy dress. 

When Kristina returned, she was holding something in her hand. “Time for the final part of today's outfit.” She held up a gag with a pink strap, the gag itself was a short but thick penis shape that would fill my mouth and almost stretch my jaw wide open. But the real kicker was the front panel. The outside of the gag was shaped like a pair of luscious, pink lips. The false lips were partially open and I could see that there was some kind of mesh hidden behind them.

Upon closer inspection… “Is that a speaker in there?” I asked.

“Well noticed, sissy. Open wide.” Kristina filled my mouth with the gag and fastened it into place. My tongue was pinned to the bottom of my mouth so that the only sound I could make was a muted “Nnnng.”

“Now, now, you don’t have to worry about talking. Not anymore. I can do that for you. Watch this.” Kristina pulled out her phone and opened an app that I couldn’t quite see. 

She hit a button and then. “My name is Sissy Paulette, the pretty maid.” The voice was mine, loud and clear, and it certainly came from my mouth, but it wasn’t me that had said it. The recordings from yesterday must have been uploaded into the speaker inside the gag.

“Hahaha, that sounds like it’s working. Pretty clever, wouldn’t you agree?”

“Of course, Mistress.” She hit another button to trigger the response. 

“Perfect! My very own remote control sissy. I’m sure you’re gonna be a big hit at the party later. Speaking of which, we have to finish getting ready. Come along, sissy.”

“Yes, Mistress.” My recorded voice said as I scurried behind her.

I helped Kristina lay out some snacks and prepare some cocktails in the kitchen. She would occasionally prompt a response using her remote and speaker, giggling at her ingenuity. “Now remember, Paulette, if the gag gets too much or you need a break for a drink then give me a signal and I’ll help you out. Otherwise it stays in place and I get to have fun. Understood?”

“Yes, Mistress.” 

“Haha, I had a feeling you would say that.” As Kristina chuckled at her own joke, there was a knock at the door. “Oh look. Our first guest has arrived. I suggest you go and get the door.”

My eyes must have widened in shock at this request. I was expected to answer the door dressed like this. “Go ahead, sissy, get the door. Don’t worry,  no one will see you….and if they did, all they would see is a big titted bimbo in a maids outfit. Now hurry up.”

So with a rapidly beating heart, I opened the front door to see Candy, the sissy I had mistaken for an actual girl the first time I had seen her.

“Oh my god, Paul! I knew you would look totally hot with some tits of your own.” Candy said brightly, diving in for a quick hug, causing a blush and a confused stirring in my cage.

“My name is Sissy Paulette, the pretty maid.” Kristina was watching from behind the door with her phone in hand.

“Well it’s nice to meet you Paulette, those boobs of yours are gorgeous. I wish mine were that big.” Candy said, cupping her own, natural breasts in her hands.

“Candy, behave yourself.” Sam and Mel had appeared in the doorway behind their sissy and I stood aside to let them in. 

“Well, well, don’t you look delicious.” Sam said, eyeing me up and down.

“How do you like the prosthetics we got you, Paulette?” Mel asked.

“I love having big, bouncy tits.” Came my pre-recorded response.

“Of course you do, I always knew you would make a fine bimbo.”

We all made our way into the house while Sam and Mel complimented Kristina on my gag/voicebox. Half an hour later, there was another knock on the door. “Go ahead, Paulette, answer the door.” Kristina said, standing up to follow me, no doubt to make sure I responded accordingly to our next guest.

It was Jane standing on the other side of the door this time, the woman who had thoroughly schooled me in our bondage wrestling match. She couldn’t help but burst out laughing as I answered the door.

“Hahaha, well aren’t you pretty as a picture?” She said as I blushed.

“My name is Sissy Paulette, the pretty maid.”

“Right you are darling, pleasure to see you again. If I had known I would be invited back for a party, I would have brought your key with me. Oh well, looks like you’ll just have to wait for the post to arrive, huh sweet cheeks.” Dammit, there goes that small glimmer of hope. “Let me know if you ever want that rematch.”

As I led Jane into the living room, my voice came from the speaker/gag. “How may I be of service to you?”

“Well I’d love some whisky if you have it.” Jane replied.

“Of course, Mistress.” ‘I’ replied, heading into the kitchen to bring the drink.

When everyone of the current guests had a drink I was left standing awkwardly beside Kristina, wondering what a sissy maid should do in this situation. I was kind of hoping someone would give me something to do when Candy appeared beside me. “Hey, there. So, how do you like being a sissy?” She asked, standing close enough that I could smell her perfume. “It took me a while to get used to it but now I can’t imagine going back to being a boring old buy, ugh.”

“Nnng.” Kristina must not have been paying attention because no response came from my gagged mouth.

“Hehehe, oooh right, you’re gagged. Ah well, I can tell by that cute blush in your cheeks that you totally love it. Maybe our Mistresses will let us play together sometime. You can play with my boobs if I can play with yours, hehehe.” Candy playfully nudged me on the arm as I stood there, blushing deeply and wondering how much feminization it would take to get to Candy’s level.

“Candy, stop teasing the poor girl,” Sam said, noticing our conversation, “not everyone is as slutty as you.”

“Sorry, Mistress.” Candy replied. “She just looks so cute in her little outfit.”

“She does, doesn’t she. Paulette, could you come over here for a sec, let me get a good look at you.”

“Of course, Mistress.” I walked over to Sam on the sofa, Kristina had her fingers poised ready on her app. “How may I be of service?”

“Oh I’m not sure. Is there anything you’d like to do for me?” Sam asked, clearly testing what kind of responses Kristina had prepared.

“Would you please spank my sissy butt for me?” Came my response as I saw Kristina giggling off to the side.

“Well if that’s something you want, who am I to say no?” Sam replied.

“I love being spanked!”

“Well I doubt you’ll be able to feel much under all that padding, but it will make for quite a show. Come along, over my knee.” Sam patted her thighs and I laid myself over her lap, feeling my oversized butt become exposed to the rest of the room. 

Sam giggled as she slapped the false cheeks of my ass, she was right about me not being able to feel much, there was a dull thud against my cheeks but no stinging aftershock thanks to all the padding. I could, however, feel how much the extra padding shook from the spanks.

My spanking was interrupted by a knock at the door. “Up you get sissy, I’m sure more people will be happy to spank you later. Go get the door.” 

“Right away, Mistress.” I hurried out of the room to greet the next guest.

“Paul! Wow, this is quite the transformation.” Emma greeted me as I answered the door and welcomed her in.

I expected to hear myself saying the ‘sissy paulette’ greeting, so I was caught off guard to hear my voice saying, “I’m such a sissy, slut!”

“Hahaha, it certainly looks like it.” I glared at Kristina who was laughing to herself behind me.

“Sorry, Paul, I was waiting for a chance to use that one but it never came up.” Kristina said, smiling in amusement.

“You look good in that outfit, Paul.” Emma said as we entered the living room.

“I exist to serve.” I replied, followed by, “I’m a good sissy maid.”

Cynthia, the pet trainer, was the last guest to arrive and soon we were all dotted around Kristina’s house, drinking, laughing and catching up. I had settled into a routine of approaching the guests, knowing that Kristina was poised and ready to play with her remote responses.

“Nice to see you again, Paul, though I must say you looked better as a puppy.” Cynthia said after she had joined the party. “But the sissy look does suit you.”

“Thank you, Mistress.” “I love having big, bouncy, tits.”

“Hahaha, well they look good on you.” Cynthia replied. I could see Kristina out the corner of my eye with her phone, laughing slightly at my responses.

“Paulette, I need a refill.” I heard Emma call from the other side of the room. I turned towards her and took the offered glass.

“How may I be of service to you?” Came my voice from the gag.

“I’d like another vodka and lime, please.”

“Of course, Mistress.” I headed into the kitchen to fix Emma her drink, and Kristina followed me. When we were clear of the rest of the party, Kristina unlocked the gag and allowed me to stretch my jaw and actually choose what to say.

“Well, how are you enjoying your party, Paul?”

“It’s definitely something, Mistress.”

“And how is your cage feeling?” She asked with a smirk, knowing the answer.

“It’s…..very tight, Mistress.” I admitted. 

“Thought so. I guess that means you like serving me and friends as a little sissy maid.”

“I guess so.” I said, taking a drink of water.

“Good, then I’ll leave you to your duties, maid. Put the gag back in when you’re done.”

“Yes, Mistress.”

I returned the party shortly after with the gag back in place. I handed Emma the drink and she thanked me, and then the speaker kicked in again.

“Would you please spank my sissy butt for me?” My eyes widened, surprised at the randomness of the comment, it seemed Kristina was bored of the simple approach.

“I’m sorry, what was that?” Emma asked, a slight smile on her face.

“I love being spanked!” “Would you please spank my sissy butt for me?”

“Well seeing as you asked so nicely, here, over my knee.” Emma patted her thighs and I blushed as I bent over her knee, noticing the rest of the heads in the room turn to watch the spanking.

Once again, my heavily padded ass was on display as Emma began firmly spanking me. The padding of the fake cheeks blocked a lot of the impact but did nothing to stop the humiliation warming the cheeks on my face as my cock throbbed in its cage.

“I love being spanked.” I said again as the blows rained down. When she was finally finished, I was allowed to stand up and straighten my skirt. “Thank you, Mistress.”

“Any time, Paulette.” Emma smiled.

“Hahaha, quite the show,” Mel said, “I’ll bet that turned you on, didn’t it, sissy.”

 “I’m such a horny slut.”

The women in the room broke out laughing as Sam said, “I’ll bet you’d love someone to play with that sissy cock of yours about now, huh?”

“I no longer own my own dick.” “My little sissy clitty belongs in a cage.” “Mistress owns my cock.”

I blushed as the humiliating words played out loud and very clearly in my own voice. 

“Hahahaha, of course it does.”

And then the phrase that I had almost forgotten about came into play. “I just love having a big, thick cock up my sissy ass!”

“Pffft, hahaha, I see you have her trained well, Kris. Nice work.”

“Yeah, that gag is genius.”

I saw Candy grinning at me behind Mel, clearly enjoying my humiliation as much as the rest of the women, or maybe she was jealous.

The rest of the evening went much the same until the guests started saying their goodbyes. By the time the evening was over everyone in attendance had spanked my padded ass, Candy included. Sam, Mel and Candy were the last to leave and we waved them away at the door. Sam had to pull Candy away as she kissed my gagged mouth goodbye.

“Well, sissy, I think that went great. I hope you had as much fun as I did.” Kristina said when we were alone again.

“I exist only to serve.” She clicked her phone, not done having fun with the gag just yet.

“I know you do, and I must say you did perfectly tonight. My friends all loved you. Consider yourself ‘approved by the girls’.”

“Mmng.” I tried to say it was good to hear.

“Now I have to say you have definitely earned a reward, anything you would like from me?” She asked with a mischievous smile as one hand worked the app on her phone.

“I just love having a big, thick cock up my sissy ass!”

“Hahahaha, well how can I say no to that. Upstairs, on the bed, now, slut!”

Kristina didn’t bother to remove the gag as she donned her strap-on that night and took me from behind. I felt the rubber shaft enter me as I moaned through the speaker in my mouth. Every now and then I would hear myself say something as my ass was pounded.

“I just love having a big, thick cock up my sissy ass!”

“With pleasure, sissy!”

 “I’m such a horny slut.”

“Yes you are! You’re my horny slut.” Kristina fucked me as she hit buttons on the app. At some point I figure she must have stopped paying attention to what buttons she was pressing as my voice kept saying random things as her thick dildo thrust in and out of me.

“I no longer own my dick.”

“Thank you, Mistress.”

“I exist only to serve.”

“My name is Sissy Paulette, the pretty maid.”

Kristina sped up more and more until she cried out in ecstasy. I could feel a dampness at the crotch of my faux pussy and figured I must have been leaking like crazy in the cage but unable to actually reach the orgasm I craved.

“Mmmm, that was perfect, sissy. Such a good slave…..I might just keep you..” Kristina said, collapsing down next to me.

What could I say to that except, “Mistress owns my cock.”

End.