The new neighbor - chapter 11 (Patreon)

The New Neighbor - Chapter 11

It happened so fast! I thought Kristina would have gradually rolled out the humiliation after I had moved in for the trial period. But here I was, less than an afternoon spent in her house and I had been almost fully feminized by her and her friends.

I hadn’t even put up any resistance, I didn’t realize how far it could all go in such a short space of time. Just a few hours and I was dressed in women’s clothes on my knees, licking Kristina’s sex while she sat on her couch.

“Good girl.” She patted my head when she was satisfied, like I was a dog who had just done a trick. I blushed a little deeper as that feeling sank in. The blindfold I was wearing was removed…I still wasn’t permitted to see her naked. Which is a weird rule considering how many times I had gone down on her so far. But I wasn’t going to complain.

“Ummm, so what do we do now?” I asked. “I’m not really sure on the whole Mistress/Sissy relationship etiquette.

“Haha, no I would be very surprised if you were. But I have an idea for something fun…..follow me.” Kristina led the way to her bondage room and we both entered. “Personally, I think with this outfit you would make an excellent damsel in distress, so I think I’d like to test it out. But don’t worry, I’ll be sure to make it fun for you.”

Kristina led me over to a large St. Andrews cross affixed to one of the walls. There were cuffs at the end of each of the cross’s points for my wrists and ankles. I allowed her to strap me into place with my back against the cross. In less than a minute, I was firmly attached to the cross and at Kristina’s mercy.

She leaned against my feminized body, and kissed me on the lips, my erection returning to full mast beneath the small skirt. “That’s better.” This was clearly the desired effect as Kristina looked happily down at my erection. “Horny, slut?”

“Yyes Mistress.” I answered, desperately.

Kristina lifted up the skirt and tucked the hem into its own waistband, exposing my erection which was now poking out the top of the panties. “Let’s get these out of the way…” She pulled the panties down enough so that my cock was sticking out, smooth and proud.

Kristina grabbed my cock and gave it a few, incredibly slow strokes. “I’ll bet you’d love to cum right about now, wouldn’t you?”

“Very much so, yes.”

“And I’d love to make you cum, it would be like a physical seal approval that you absolutely love your new, sissy look. Imagine squirting your cum while dressed up and made up to look like a sissy, strapped to a cross and totally at my mercy. I think that would certainly say something about what kind of man you really are, wouldn’t it?”

My head was spinning at this statement/question. But I knew the answer. “Yes, Mistress.”

“I would love to make you cum, but I would also love to deny you, and watch you squirm, desperately as I edge you over and over again.” She returned to the very slow stroking with a feather light grip on my cock. “Which would you prefer?”

Was that a serious question? “I would prefer to cum, Mistress.”

“Of course you would. But what would you give me in return, I wonder?” Kristina looked down and let a long strand of saliva drip from her mouth, right onto the head of my aching cock. She quickly began rubbing the saliva into my shaft, using it as makeshift lube, driving me crazy.

“Anything, Mistress!” I moaned in response. “I’ll give you anything.”

“Anything? Really? That’s quite a lot to offer. What if I was to say, I want you to swear to me that you will never wear male underwear again? Would you be willing to give me that?”

“Ummm, I-I..” Kristina gave me a few quick pumps to interrupt my attempt at an answer.

“What if I was to say that I wanted you to walk over to your house, dressed like the slut that you are and bag up all of your male underwear. Then I would make you watch as I cut all of them into ribbons. Would you still be willing to give me that?”

“I-I’m not sure….That seems like a big commitment?”

“Am I not worth a big commitment?” She asked, smirking as she teased my cock with one finger.

“O-of course you are…”

“So you’ll wear panties for me, always? Is that what you’re saying?”

“Oh..Ffffuck..” I was going to cum, I could feel my balls tense and my cock twitch…then Kristina whipped her hand back right before I crested. Denying me.

“Oh no you don’t. Not without my permission. You will never cum without permission while under my roof, is that understood?”

“Yes, Mistress. Sorry…I’m just so turned on right now.” I replied as the crushing frustration of the denied orgasm washed over me.

“Of course you are. Because I was telling you about how I might just destroy all your male underwear and make you wear panties permanently, and the thought of it turned you on so much that you almost came just to the idea. Isn’t that right?”

Was I supposed to answer that? And what was the answer, was that something I really wanted. I had to admit the idea of her being able to make such a significant change was extremely arousing. “Maybe, Mistress. I’m not sure.”

“Hahahaha. Of course you’re not. But don’t worry, we can talk about panties later. What if I was to ask for something else?” She resumed her teasing of my desperate cock.

“What if I wanted to throw a party for all my dominant friends, with you as the entertainment? Would you trade that for an orgasm?”

The thought of being on display for all her friends was both terrifying and arousing. “Maybe…..Ohhh, please, Mistress. I’m close.” Her hand stopped again.

“Yet another idea that seems to turn you on. Something else that I’ll have to file away for later.” Kristina said as she let me cool down for a few seconds. Her plan was becoming clear, she would make a wild, erotic suggestion that would test my submission, and use my reaction to gauge what turned me on. It was interrogation by teasing, and it was working.

“How would you like me to loan you out to my friends? What about Sam and Mel, I’ll bet they would love another sissy to play with. Would you like that idea, Hmm? I’ll bet they would love to

See you and Candy playing together.”

My cock actually jumped at that idea and she had to pull her hand away quickly, edging me again.

“Hahaha, I knew you had a little crush on Candy. Hardly surprising, she is a very pretty girl.”

“Please let me cum, Mistress.” I begged, I couldn’t take much more of the teasing and edging.

“Maybe I will, maybe I won’t.” She stroked me again, agonizingly slowly. “Right now we’re trying to find out just how much you’re willing to give me. How far you’ve fallen after just one day with me. What if I had you trained to be a perfect little puppy? I know a girl who specialises in pet play. A few hours with her and she could have you wagging your tail and barking happily like a cute little puppy. Would you like that?” I hit the edge again and broke, I couldn't stand anymore.

“Oh god yes. Yes I’ll be your puppy, I’ll be your sissy. I’ll be anything you want me to be, just please let me cum.” I thrashed desperately in my bonds, pulling hard on the straps at my wrists. Desperate to break free, desperate to cum. Desperate for anything.

“Hahahahaha. There it is. There’s that damsel in distress I’ve been waiting for. Go ahead and struggle, slut. Break those chains and take what you want.”

I was trying! I really was. The muscles in my shoulder were straining as I pulled, but I wasn’t going anywhere, we both knew that. Eventually I slumped over in my bonds, breathless and defeated.

“Giving up so soon. Ah well. Just so you know, I was never going to let you cum this early on. Your orgasm will be earned when you’re with me. I’ll leave you here to cool down for a while.” She turned on her heel and walked away, leaving me trapped and desperate against the cross.

Eventually, I was released from the cross, but I was still horny and I don’t think my cock was ever fully soft for the rest of the day. She kept up her teasing ways but for the most part, we were able to have a relaxed afternoon. Or as relaxing as it could be with me dressed like a sissy. Kristina even made us both dinner.

Nightfall rolled around and Kristina declared that it was time for bed….

“Okay, Paulette.” Kristina addressed me as we entered her bedroom. “Time to get ready for bed.” She walked over to her wardrobe and opened up one side, there was a small section that had a few different pajamas and nightwear hanging, in a mix of different fabrics. “Personally, I would recommend a nice night dress, seeing as it’s your first night sleeping as a sissy.”

Kristina pulled a long, blue silky nightgown down from a hanger and held it up for me to see. It would be long enough to cover almost my whole body, with two thin straps that would go over my shoulder. The material shimmered as it reflected the light in the room. “What do you think?”

“Looks nice.” I replied, although I wasn’t sure how nice it would look on me.

“Strip. Then I’ll help you with this.”

I removed what little clothes I was still wearing, leaving me in just my panties. I gave Kristina a questioning look.

“Those can stay on. Arms up.” Kristina gathered up the long night dress until it was a shimmering bundle of fabric, she reached up and dropped it over my arms. The silky fabric dropped down all the way to my ankles, rubbing and teasing against my smooth skin. The fabric clung to me as it hung from my shoulders, the outline of the panties was visible whenever the night dress pressed against my thigh or rubbed against my crotch. Of course my erection made a notable return.

“Looks like you approve.” Kristina smiled down at my crotch. “Is that going to be a problem? You know you’re not allowed to touch yourself without my permission. And I would be VERY displeased if you started disobeying me on the first day.”

“Umm, that depends…..do you plan on, er, pleasuring yourself tonight?” I asked. The eroticism of the whole day had left me desperately horny and I knew if I was home alone, I would have already jerked off like four times today.

“I might do, yes. But what I do in the privacy of my own bed is up to me. What I’m asking you, is if you can keep from playing with yourself while I do whatever I feel like doing.” Kristina reached down and pinched the silky fabric of the nightdress, giving it a small swish that rubbed the head of my cock beautifully. The feeling of that fabric rubbing against me and my smooth body was enough for me to know the answer.

“Errr, maybe not, if I’m being honest…Mistress.”

“That’s what I thought. In that case, is there anything you can think of that might help you resist the temptation?” Kristina asked, her closeness and sultry tone causing my erection to cry for some attention.

I thought for a second before I realized what answer she was looking for. “Ummm, the chastity cage?”

“The chastity cage! What a great idea.” Kristina answered brightly. “If that’s what you want then I guess I could let you use the chastity cage. If you ask me properly.”

Dammit, she had put me in a situation where it had become my idea to be locked back in chastity, and made it seem like she was doing me a favor. A favor I would have to ask for.

I looked up to see a smug smile on Kristina’s face as she saw me realize what had happened. I sighed in defeat before answering. “Mistress, could I please use the chastity cage?” I asked.

“And why would you need the chastity cage, sissy?”

“Because I really don’t think I’ll be able to resist touching myself tonight.”

“Very well, Paulette. If you insist, then of course I’ll let you lock yourself up tonight. Here you go.” Kristina pulled the cage out from her drawer, clearly she had it waiting ready.

She gave me a few minutes alone to lock myself up in the bathroom. Day one and I had been turned into a sissy and had locked myself, ‘willingly’ back in chastity.

I returned to the bedroom to see Kristina sitting on her bed in a silky, white negligee that barely covered her thighs. There was no way this was regular sleepwear for her.

“Ah, good. I take it you’re all locked up?” She said as I re-entered the bedroom.

“Yes, Mistress.” I replied.

“Good, because I need your help with something.” Kristina reached behind her and grabbed two items from the bed. Two different dildos. “I can’t decide which one of these vibrators I want to use to pleasure myself with tonight. I like the pink one because it has these little prongs that stimulate my clit just right, but the purple one is a little longer and thicker. I was hoping you could help me decide.” She looked at me with an innocent smile, a contradiction considering that she knew exactly what she was putting me through with a question like that.

The cage was instantly uncomfortable. “Umm, I would go with the uhh, the pink one.” I replied, the desperation obvious in my voice.

“Good choice. Pink it is. Here, give it a little kiss for me, for luck.” Kristina held up the pink vibrator and I leaned in, intending to give it a reluctant peck. As soon as I did, Kristina pushed it against my lips, smearing the head of the cock around the inside of my mouth. “Thanks. Now it’s time for you to get into bed.” Kristina pulled up the sheet hanging off the bed, revealing the caged area underneath, the gate was unlocked, waiting for its prisoner.

I crawled inside, the fabric of my nightdress clinging to my legs around me as I did so, leaving Kristina to her bedtime ‘fun’.

“Goodnight, sissy.”

“Goodnight Mistress.” My bed was plunged into darkness as Kristina locked the gate and dropped the sheet back down, hiding me from view.

I was only laid in bed for a few minutes before I heard movement above me. The sheet surrounding my bed was shifted aside a little and a small…something, fell between the bars into my bed.

I only had to touch the item a little to realize what it was. Her panties. There was absolutely no way this was an accident. The sheet didn’t just happen to fall aside so the panties could fall between the bars of my cage.

The fabric was still warm and there was a noticeable fragrance that I detected when I inhaled. A fragrance that I recognized, having been quite intimate with it in the past. It took me a second to realize that I was slowly bringing them a little closer to my face. Was I really thinking of doing what I was thinking of doing?

I inhaled again, a little deeper this time, but this didn’t count as sniffing her panties….I wasn’t one of those guys, right?

I was distracted by the sound of the vibrator clicking to life. My cock pushed hard into the cage at the thought of what was happening above me…again. I inhaled again, sharper this time, deeper. Pulling the intimate, womanly scent of Kristina into me, like it was some kind of drug.

I laid there, all pretenses gone, sniffing Kristina’s panties and listening to the sounds of her pleasuring herself above me. Desperate and frustrated.

—

I woke up, a little disorientated until I remembered where I was, Kristina was breathing lightly above me, still asleep. It was this moment that reminded me of my situation. I couldn’t leave the bed until she woke up and unlocked the gate, nor could I touch myself or even enjoy my morning erection. The panties were next to my head, I had managed to resist the urge to press them against my face, but I did make sure they were close enough that I could catch their scent. I convinced myself that it was less perverted that way.

She woke up a short while later, I heard her feet hit the floor outside the sheet near my bed and waited for her to release me. Kristina padded out of the room, used the bathroom and then light flooded my sleeping area.

“Good morning, Paul. How did you sleep?” Her voice came from above me.

“Morning, Mistress. I slept….fine. Woke up a few times thanks to the cage, but otherwise, quite cosy in there.” I said, crawling out of the cage and standing up.

“Good to hear it. Do you have anything you need to do today? Any obligations you need to fulfil?” She asked.

“Umm, I don’t think so. But I could do with logging in and just checking my work emails, make sure nothing major has happened in the last twenty four hours.

“Very well. No meetings or calls you need to dial into?”

“No.”

“Good, then there will be no need to get changed. You should check your emails now before we do anything else. When you’re finished, meet me in the changing room. I have a surprise for you today. I think we’ll leave the chastity cage in place for a while, but behave yourself today and I may let you out later tonight.”

“Yes Mistress.” I replied, grabbing my laptop and logging in on a small table in the corner of her bedroom that she had said I could use for my laptop. No disasters that needed my attention today, but there was something I had almost forgotten about.

I headed into the room that I had been transformed in yesterday, night dress still swishing around my legs, and greeted Kristina.

“That was quick. I take it everything is fine without you?” Kristina asked me.

“Yep, all good. But uh, there was one thing I was going to ask you?”

“And? What is it?”

“Well, there’s a uh, thing at work tomorrow night. A retirement party for one of the senior managers that I kind of need to show my face at. It’s been planned for a while and I was actually thinking of asking you if you would like to go with me, but I never got up the courage to actually ask. Which seems crazy now, given our current situation.”

Kristina smiled a little as I told her this. “Well, that sounds fun. Hopefully you manage to find the courage to ask me to go with you then.”

“Good point. Umm, Mistress…Kristina, would you like to go to a party with me at work tomorrow?”

“Why yes, I would love to. Give me a chance to meet some of your colleagues. But that’s tomorrow. Today, Paulette gets an upgrade.”

Kristina had me strip naked before doing anything else. I wondered what she meant by ‘upgrade’, but that question was answered shortly after I had removed the night dress.

“I had Sam and Mel make a special something for your transformation yesterday and I can’t wait to see how you turn out.”

Kristina pulled out a large box, lifted the lid and peered inside as I waited to see what was in there.

The first thing she lifted out was a realistic, flesh colored pair of breasts, maybe around a C cup, perhaps a little bigger. They were attached to what looked like a flesh colored bra strap that ran around my back and shoulders., holding them in place.

“May as well start with these.” Kristina stretched out the wide, skin-tone strap and pulled it over my head as I allowed my arms to be guided through the shoulder straps. When she let the straps snap into place, I could feel how tight they were. I looked down to see the two boobs, complete with realistic, very erect nipples jutting proudly from my chest. “One more second…” Kristina grabbed a small spray bottle from the box and stretched the fake breast away from my skin a little so she could spray the adhesive onto my pectoral area. “This spray will help keep the breasts attached where the seams meet your skin, so it will be less obvious that they’re fake, at least to the casual observer.”

To say it was weird looking down at my body and seeing a pair of tits would be an understatement. Especially as I could see my caged cock when I looked down between them.

“They look pretty good, although I think they took liberties with the nipples.” Kristina said, pinching the erect nipple between her fingers. “Haha, I guess I shouldn’t be surprised, knowing those two like I do.” Kristina admired my new tits for a second before returning to the box. “This is what I’m most looking forward to. I remember you saying you were an ass man, right? Well, what do you think of…this?!”

She hoisted out the next item from the box, I should have seen it coming really. A rather large, hefty looking pair of shorts in the same flesh tone as the breast top, but of course these shorts had a pair of wide hips and large cheeks attached.

Kristina held the shorts open and I stepped in, it took a good amount of effort on both our parts to pull the shorts up into place. The crotch had a prominent outline and shape of a woman’s pussy lips moulded into it with a small cutout section that would allow me to pee, behind this moulding was a small pouch where my own package could rest inside. The shorts rode up high on my waist and snapped into place incredibly tightly, squeezing in my own waistline a little due to how tight they were.

I could feel the additional weight of the enlarged ass cheeks behind me as the front panel crushed my package behind the faux vagina, my equilibrium was thrown off by the tits and ass combo.

“That really is a good look for you, sissy. Worth the cost of the prosthetics, wouldn't you say?” Kristina said as I rubbed my hands along my new curves.

“Umm, yes, Mistress?” I replied, uncertainty.

“Let's complete the look, then you can judge.”

Kristina grabbed some clothes from the drawers and dressers and put together an outfit for me to wear.

It started with a matching pink bra and panty set, both were trimmed with lace and the panties were a full cut rear with a good portion of the seat wedged between my oversized ass cheeks. These were followed by a pair of tight, blue lycra shorts, similar to something you would see on an influencer in the gym who wanted to show off the shape of her ass. A seam ran between my cheeks so that they were separated and defined, but the real eyecatcher was in the front.

When Kristina had finished pulling the shorts into place, I saw the reason for the extra ‘volume’ on the lips of the fake pussy. Kristina laughed when she saw the finished result. “Hahaha, wow. They gave you one hell of a camel toe!”

“What?!” I looked down to see what she meant. The tight pouch compressed my package and the shape of the cage or my bulge was hidden by the fake pussy, the outline of which could clearly be made out behind the tight shorts.

“Hahaha, I should thank Mel for that one I’m guessing.” Kristina chuckled to herself.

It was a strange feeling, looking at my crotch and seeing pretty much all signs of my manhood completely erased.

Kristina finished off the outfit with a tight vest top that was cut low enough to expose cleavage and the lacy tops of the bra. “Looking good. A little slutty, but good. Now, into the makeup chair.” I sat down at the same makeup station as yesterday. “I’m not quite as good at the makeup as Sam or Mel but I think I could do something that works….”

I could see the concentration in her face as she worked on me with the makeup. When she was finished I was barely recognizable as a man. The shorts hid the seams of the fake butt-pants I was wearing and the top and bra hid the edges of the fake boobs.

“Mmmm, It’s going to be tough to keep my hands off you when you look like this.” Kristina said, moving in close as I checked myself out in the mirror, she wrapped her arms around me, causing my cock to twitch in the cage.

“Don’t let me stop you.” I replied. It was incredibly weird to think I was inviting someone to fuck me while I was dressed like this, but I was still turned on by Kristina.

“I knew you’d be a slutty sissy.” Kristina slapped my ass, there was no sting or pain of any sort, but I felt the rubbery cheek jiggle erratically.

“I guess you bring it out in me.” I replied.

“Behave yourself, slut. Or I’ll coat that fake pussy of yours in surgical glue next time. See how you like having that camel toe on display for a couple of weeks.”

“Yes Mistress.” I knew Kristina wasn’t the kind to make empty threats.

“Now, you can go downstairs and make me a coffee and two slices of toast while I get ready for the day. I’m heading out to do a little shopping soon. You’ll be cooking tonight, like a good little housewife. Anything you’d like to make?”

“Umm, well I make a decent peppercorn sauce if you want to grab a couple of steaks and some creme fraiche.”

“Great, steak it is. I’ll get what we need.”

I jiggled my way downstairs, feeling my weighty butt move and my boobs bounce as I descended. I made Kristina her light breakfast and coffee as requested. A short while after that she was ready to leave.

“Okay, Paulette (I still wasn’t used to the feminized version of my name), I won’t be gone long, but while I’m out you can clean up a little. It just occurred to me that you might need a maid outfit in the future…I’ll have to call Sam. In the meantime, the vacuum cleaner is under the stairs and there are other cleaning supplies below the sink. See you later, slut.”

“See you later, Mistress.” I couldn’t help but wonder to myself…How did I get so lucky?

End part 11