The new neighbor part 8 (Patreon)

The New Neighbor - Part 8

Today was the day! I was finally expecting to be freed from the chastity cage. I was distracted all day at work, knowing that I was going to see Kristina to take the cage off right after. It didn’t help that as part of an earlier punishment, she had swapped out the cage I was almost getting used to and replaced it with a much smaller, tighter one.

I drove home a little faster than usual and my heart soared as I saw Kristina standing just outside her front door, watching as my car pulled into the driveway on my side.

“Hey Kristina.” I said, the excitement obvious in my voice.

“Hello, Neighbor. You seem to be in a good mood.” Kristina replied, noticing my smile.

“Yeah, well. I’ve been looking forward to today all week.” I said.

“I’ll bet. If only you had behaved yourself, you would be out by now. Ah well, all water under the bridge. Come on in, I have company so this might have to be a quick visit.

“Company, right. I could come back a little later.” I said, I wasn’t exactly looking to have this conversation in front of a stranger.

“Don’t worry about it, come on, I want you to meet my friend.”

We walked into Kristina’s living room, where a very attractive young woman was sitting on her couch. I noticed there was a large suitcase packed near the doorway.

“Samantha, this is Paul. Paul, Samantha.” Kristina introduced us and Samantha rose to shake my hand in a polite greeting.

“Ahh, so this is the new neighbor you’ve been telling me about.” Samantha. “He’s cute. Hello, Paul. Call me Sam.”

“Hi Sam, Paul. So..” I said, turning to Kristina. “Been telling your friends about me? All good I hope.” I wondered just how much she had actually told her.

“Most of it is good, yes. You come off rather well, at least.” Kristina replied, before adding. “Samantha and I are about to head to a convention for the weekend in Daytona.”

“Ah, that explains the suitcase.” I said.

“Yeah, and we really need to get going if we’re gonna catch that flight.” Sam added.

“Oh, you’re gone for the weekend.” The disappointment was obvious on my face.

“Yeah, maybe longer if we find anything fun to do while we’re out there.” Samantha added.

“Aww, don’t worry, Paul. I’ll be back before you know it. But we really must get going. Is there anything you need before I head off?” Kristina looked at me with a smirk as she knew exactly what I needed.

“Umm, yeah. There is, actually.” I replied, not sure how to phrase this with Sam in the room.

“Well, what is it? Come on, Paul. I have a plane to catch.”

“Yeah, Paul.” Sam added from off to the side. I was nervous now, did Sam know about the cage? Did she know about Kristina and my relationship, or whatever it was?

“Actually I was wondering if you had that key of mine.” I said.

“Key? What key?” Kristina said, grinning evilly.

“You know…the key to my uhhh, thingy.” The ‘thingy’ in question was currently throbbing as I knew what Kristina wanted to hear. She wanted to embarrass me one last time before I was granted release.

“What thingy? Come on, Paul. We need to leave, so either tell me what you need or leave and we’ll pick this conversation up in a few days when I get back.”

“Okay, fine.” I decided I had to risk it, I guessed Sam had to know what Kristina was into. “The key to my chastity cage. Could I please have the key to the chastity cage before you go?”

My face burned with embarrassment as Sam spoke before Kristina could answer. “Hahahha. Oh my god, Kris you have him locked already? Wow you don’t mess around.”

“Wait, what..Already?” I stammered.

“Oh relax, Paul. Sam is a good friend of mine, we met at a BDSM convention a few years ago so she’s well aware of what type of things I’m into. Now, as for your key. Of course I will give it to you, but first I need to check that you’re still following the rules.”

“Oooh, what rules?” Sam asked.

“Better be quick if you want that key Paul.” Kristina prompted.

“Okay, okay.” I had already stepped into humiliating territory, I may as well get this over with.

I pulled down the front of my pants to display the red lace panties I was currently wearing. Both ladies were smiling wide whilst I blushed profusely.

“Wow, and in panties too. Very nice work. So do you think he’d make a good sissy? Do I need to call my friends over?” Sam said as I hid my panties from view while wondering what ‘friends’ Sam might have been referring to.

“He makes a very sexy sissy actually. But right now he’s still finding his feet, so who knows what I could turn him into.” Kristina winked at me at that sentence.

“There. Could I please have the key now?” I said, getting back on topic.

Sam answered before Kristina could. “Oh hey do you still have that rule where no chastity sentence can be shorter than the last?”

“Of course.”

“So how long has Paul been locked this time?”

“Tell her.” Kristina said.

“Eight days.”

“Wow, so eight days minimum sentence already. Either you must be a really bad boy or Kris really likes you.” Sam said, looking at Kristina. We could both see the ever so slight smile and blush that on Kristina’s face, but it was hidden beneath her more mischievous expression less than a second later.

“Okay, well we really do have to go now. Paul, you’ve earned your key.” Kristina said, stepping close to me and sliding her hand into my pocket, presumably leaving the key while giving her a chance to make sure I was as aroused as could be at how close her hand was to my caged dick.

“Luckily for you, Paul,” Kristina said as she readied herself to leave. “Sam is familiar with the BDSM scene. But I want you to think about how ready you were to humiliate yourself in front of a total stranger after just eight days in chastity, how much it turned you on and just what I could have you doing if you keep this up.” Kristina’s words rang in my ears as we all left her house.

She had an excellent point, I had trusted her enough to let her lock up my cock, and then willingly exposed the shameful secret to a stranger, simply because Kristina had told me to. I think she already had more control over me than even I was aware of.

—

The next two days were a blur of masturbatory fantasies for me, I was determined to make full use of having access to my cock. Of course, all the fantasies led back to Kristina dominating me in some way eventually.

I found myself missing her over the weekend, so much so that I considered buying another one of her videos, but I didn’t. I did watch the one I had already purchased a few more times though, to my own surprise, I found myself wishing I knew what it felt like to be taken from behind like the guy in the video. I tried to shake those thoughts clear of my head. I mean, what guy would want to be fucked up the ass like that? Apparently I would.

As I arrived home on Monday, I noticed lights coming from Kristina’s house. She was home from her convention. I thought about knocking on her door just to say hi, but I figured that would make me seem a little too needy. So I headed inside, got changed, ate some food and watched TV.

An hour or two after getting home, there was a knock on my door.

“Hi, Kristina.” I tried not to sound too happy at the sight of her. “You’re back. How was your weekend?”

“Hi, Paul. It was great thanks, the convention was a blast. If you have a free minute, I brought you back a gift. It’s over at mine” She said, surprising me.

“Oh, really? Thanks.”

I followed Kristina back to her house, wondering what exactly this gift could be. “It’s a surprise, don’t worry. I’m sure you’ll love it.”

I followed Kristina into her living room, and there on the table in front of her sofa was a large, square box.

“Open it.” She said with a smile.

I did so. It took me a second to register what I was seeing, it looked like a replica of a woman’s midsection, from the waist down to just above mid thigh. Two round, somewhat familiar looking ass cheeks were pointing up at me from the box.

“It’s a gel mould replica of my ass. Seeing as I know how much you love it. I had it made at the convention.” Kristina explained.

“I thought it looked familiar.” I said, studying the lifelike ass in the box.

“Well it should, you’ve had a rather up close at my ass a few times before. Now you can do it whenever you want.”

“Haha, I guess you’re right. Thanks, I love it.” I said, lifting out of the box and turning it around. There was the faint outline of her crotch at the front, but nothing in much detail around that area. Kristina (as usual) seemed to know what I was thinking.

“I made sure they left that part blank, you haven’t earned that right yet.” She said with a coy smile.

“Ha, fair enough. They did a good job of your ass though. Really captures your good side.” I said, and I meant it. There was a definite weight to the replica and the thick gel meant that the cheeks jiggled somewhat realistically. “So what kind of convention was this again?”

“It was a BDSM convention, obviously. There was a stall set up promoting these replicas. Guys getting replicas of their kicks made or girls could get their boobs done. I wanted to give it a try and I thought you would just love it.” She chuckled as she explained.

“Well it's beautiful. I'm sure it will make a great pillow.” I said, giving one of the flesh colored cheeks a slap.

“Hey, careful with that. I'm the one that dishes out the spankings, remember.” Kristina winked.

We laughed and liked for a little while after that while Kristina filled me in on some of the other things she saw at the convention, most of it was erotically charged enough to turn me on to some degree.

Then I noticed something underneath the box that had contained my gift. It looked like a series of Polaroids, all of them showing pictures of the same man. One of them showed him wearing a bra and panties, one was a head shot of him licking the tip of a lifelike dildo. Kristina saw me looking and quickly snatched them out of view.

“Shit. Sorry. Just pretend you didn't see those.” She said, tucking them away out of view.

“No problem, did you take those of a client?” I asked.

“No, he sent me them, as blackmail photos.”

I was a little confused about that. “Blackmail?”

“Some people have a fetish for it.” She shrugged.

“How does that work? They send you photos and ask you to blackmail them. Why don't they just ask you for whatever it is you blackmail them into?” I asked.

“Well some people like the thought of a woman having that kind of control, some people need that little extra push to try out new things. That's where blackmail comes in. But it's all decided beforehand.”

“Okay, I guess that makes sense.” I said.

“Think about it, Is there anything you’ve been a little tempted to try but your nerves or your ego or something else stopped you?”

I thought about the video of Kristina with the strap-on, and the thoughts I had shaken out of my head. “Well, yeah I guess.”

“And?” Did she want me to tell her?

“It’s…nothing.” I said, blushing and aroused at the thought of it.

“Come on, Paul. You should know by now that nothing you say is going to scare me off.” She said.

“I guess you’re right. I suppose after watching that video of yours, particularly the end scene, I am a little intrigued by the whole, umm, strap-on thing.”

I saw a definite twitch at the corner of Kristina’s mouth as she listened to my admission. “Ahhh, so you want to know what it feels like to be pegged?” She said, leaning forward in her chair.

“Well I wouldn’t say that…Just that, I was curious is all.” I replied, suddenly a little nervous. I had a feeling that if Kristina wanted to shove something up my ass, I would likely let her.

“Haha, no need to get so flustered, Paul. I know exactly how to handle a strap-on.” Her voice had dropped to a sultry purr as she leaned forward. “I could make you feel so good you’d never want to have sex any other way again. I could have you begging for my cock every night.”

I swallowed as I struggled for anything to say to that.

“Hahaha, see, obviously you’re into the idea. But I’m guessing your male ego is getting in the way, telling you that taking a cock up your ass makes you less of a man somehow. But I know you’d love it. You just need that little extra push to get you there.”

“So that’s where your blackmail comes in?” I said, adjusting myself to hide the erection her speech had just given me.

“Naturally. Tell you what. I’m not going to say what I will or will not do to you, but you may as well try it out, you’ve already experienced quite a few other kinks at my hands. If you want to see what kind of fun you could have with blackmail, then send me an embarrassing photo. Easy.”

“What kind of photo?” I asked.

“Whatever you want, I suppose. Just make sure it’s a photo you don’t want anyone to see.” Kristina said, and I had a feeling I knew what she meant.

“Okay. I’ll think it over.” I replied.

A short while later it was time for me to go home, so I stood up from my seat and made myself ready to leave.

“Don’t forget to take my ass with you.” Kristina said, referring to my gift.

“Ha, like I could forget a thing like this.” I replied, lifting up the box containing the life sized replica.

“Make sure you give it a kiss goodnight before you go to sleep.” She added as I left. I wasn’t sure if that was a joke or an order.

So there I was, sitting up in bed, staring at the replica of Kristina’s ass as I pondered this evening's conversation. One hand was idly stroking the curve of the gelatinous ass cheeks, occasionally giving a cheek a light slap to see how they rippled. It really was quite a well made piece.

But what was I to do about the photo she had mentioned? Would I send it? What would she have me do if I did? Would she use her strap-on like she said? And would I let her?

I fell asleep pondering the answer to all these questions and trying to decide whether or not to send the photo. By the time I woke up the following morning, I figured I had my mind made up. After all, had I not enjoyed pretty much everything Kristina had done with me so far?

I got home from work that afternoon with a plan formed in my mind. Kristina said if I wanted to try out the blackmail thing I should send her a photo I wouldn't want anyone else to see. So naturally, I grabbed a pair of panties.

I stood in my bedroom, phone in hand, wearing nothing but a hot pink thong which barely concealed my package. The problem was that as soon as I went to take the photo I chickened out. The thought of having an actual record of me in this state was bad enough, but sending it to another person, who could do god knows what with it, was terrifying.

But this was Kristina, I trusted her. To hell with it, the thought of Kristina having another modicum of control over me was starting to turn me on, and the thong would not be able to contain an erection. I stood in front of my wardrobe mirror and took the picture. There was me, standing in nothing but a thong with the beginnings of an erection. I took a deep breath, then hit send.

Then I panicked! Why the hell did I do that?!

After about five minutes of heart pounding nerves, I got a single, two word reply.

‘Very cute.’

Was that it? Apparently it was, I got nothing else after that for the rest of the night, and fell asleep wondering what would happen next.

—

The next day at work I had still heard nothing from Kristina, so I was left wondering just what she would do. I got my answer when I arrived home from work that afternoon. As soon as I pulled into my drive I saw something stuck to the middle of my front door. It was around the size of a post-it note, so I couldn’t make out what it was until I was standing right in front of my door. It was the photo I had sent to Kristina. Me in the thong, with the word ‘SLUT’ printed in big, bold letters.

I panicked a little at seeing this photo on my front door. How long had it been there? Had anyone seen it? What if the mail man had been? He would have definitely seen. What if a passer by saw it and got curious and came to look?

I quickly yanked the photo off my door and walked over to Kristina’s, knocking loudly.

“Why hello, Paul? How was work?” She asked as she opened the door.

“Kristina!” I said, annoyed at her for the first time since I had met her. “Are you kidding me with this?” I waved the photo about.

If she was at all worried or remorseful at my obvious annoyance, it didn’t show. She seemed to straighten up and compose herself before answering. “Relax, Paul. It’s just a tiny, post-it sized photo of you in your panties. I’m almost certain no one saw it.”

“Almost certain! What if the mail-man had seen it? Or someone passing by? Or….or.”

“Paul. Calm down. You sent me the photo, knowing what I would use it for. This was just a taste of what could happen if you’re not careful. Now I suggest you calm down and stop making a scene on my doorstep or I’ll blow that photo up to an eight-by-ten and staple a copy to every tree in the park!” That last threat definitely got my attention.

“Right…sorry. It’s just, I didn’t expect it to be waiting for me on my door when I got home. I thought it would just be like an assumed threat kind of thing.” I said.

“It is, mostly, but you need to understand just how easily I could circulate this photo. Even if I don’t know any of your friends' contact info. So now that you understand, it should make it easy for you to follow my instructions.”

“Right…So, how long do you intend to keep the photo hanging over my head?”

“As long as you want me to, obviously. If you tell me to delete it right now I will, but I don’t think you want to do that.”

“And what makes you so sure?” I asked, even though I already knew the answer.

“Simple. I know you. I’ve dealt with men like you my whole professional career. Granted you’re a lot nicer to be around than most, but still. I understand what you want better than you do. So go ahead, Paul, ask me to delete the photo.”

I paused for a moment, but as she had already said, I didn’t really want her to stop. “No, it’s fine I….I want you to have it.”

“I thought so, now, wait here.” She disappeared into her house for a moment, leaving me standing on her doorstep until she returned. “Here, catch.” She tossed something shiny to me, but I didn’t see what it was until I had caught it.

“Is this a…a butt plug?” I asked, given the shape I knew exactly what it was, but I was confused as to why she had given it to me.

“Obviously it’s a butt plug.”

“What do you want me to do with this?” I asked.

“It’s a butt plug, Paul. I’m sure you’ll figure it out. Goodbye.” She closed the door before I could say anything else. It took me a second to realize that I was standing out in public, examining a butt plug. I scurried over to my own house quickly.

After doing the things I usually did after getting home from work, I was left standing in the bathroom, naked after a shower and holding the small, silver plug in my hands. It looked pretty non-threatening, but knowing where it was going didn’t exactly have me thrilled. I opened up the mirrored cabinet above my sink and found half a bottle of unused lube. Lucky me, I guess.

I lubed up the plug and pressed it against my ass, the whole act making me feel dirty and submissive. There was immediate resistance from my rear, never having anything shoved up there before.

“Ahh!” I yelped as the plug made it past the tight ring and settled itself into place in my ass. The feeling of having something up there was definitely new to me. The plug was small but it felt huge as it rubbed against the inside of my ass. I could feel a difference in how I was walking, and had to concentrate on making it obvious that I had something up there.

What now? I wondered.

I text Kristina to let her know that the plug was in place and received a reply shortly after.

‘Good work. Keep it in for as long as possible tonight, but don’t sleep with it in. Wear it to work tomorrow, then come see me after.’ She didn’t elaborate any further.

I got dressed and chilled out alone for the rest of the night, feeling the plug constantly shifting around inside me, especially when I sat down, was incredibly distracting. Needless to say I pleasured myself before I took the plug out that night.

—

“Morning, Paul.”

“Morning, Chelsea.” I greeted a few people on the way into work after sitting in my car waiting for my erection to die down. The drive to work was torture thanks to the plug. Every vibration on the road could be felt rippling through the plug in my rear.

“You okay? Look like you’re walking a little funny?” Chelsea asked as I passed her on the way to the office.

“Hmm? Oh, yeah. Think I pulled a muscle in my leg or something.” I lied, feeling the blush creep up my face.

I winced a little as I sat down, the thin padding of my office chair causing the plug to push further up inside me. Worse than that, my erection was returning, the thought of Chelsea knowing that I was currently plugged sent a thrill throughout my body. The rest of the working day was mostly boring, I stayed seated for as long as possible, to avoid anyone else commenting on how I might be walking.

I was incredibly horny on the drive home, partly because the plug was still rubbing against my insides with every bump on the road, and partly because Kristina had told me to go straight to her house after work. Which is exactly what I did.

I knocked on her door as soon as I got home, after checking to make sure there was no sign of any pictures stuck to my door again of course.

“Paul, you made it through the day then. Come on in.” She led me into her house. “So, how was it having a plug shoved up your ass at work all day?” She asked like it was a perfectly normal question.

“Uhh, different. Distracting.” I replied.

“Did it turn you on?”

“Yeah, I guess.”

“I knew it would. Now, it’s time for the next part of your anal training.” She said, leading me towards her bondage room.

“Wait, wait, wait. Anal training? Is that what this is?” I should have known after our conversation about strap-on play and her giving me the plug to use, that this would be leading somewhere down these lines. But hearing her say she was giving me ‘anal training’ made it sound way too real.

“Yes, of course. If you’re going to want me to fuck you with my strap-on, and believe me when I say that you definitely do, then you need to be properly prepared.”

I stepped into the room and noticed a chair had been moved into the center. It looked a little like the queening chair I had been introduced to before, with a cutout in the seat cushion, but I could guess what this cut out would be for.

“You’re going to need to remove your pants and underwear and take a seat.” Kristina seemed to be in business mode, her tone was simply a statement, an instruction which I was expected to follow. And follow I did.

When I sat down, pantsless and erect, in the chair. Kristina secured my wrists to the arm rests with some built in straps. A larger strap was brought over my thighs, keeping me firmly in the seat. When she was happy that I was secured, Kristina wheeled over another device, something I recognised from a video I had seen online.

“Is that a fucking machine?” I asked.

“Ah, good. You’re familiar. That will save me some time. Yes, Paul. It is a fucking machine. A dildo attached to a piston that will extend and retract.” She reached beneath the chair and removed the plug from my ass. Replacing it with the tip of the dildo at the end of the fucking machines arm. With the head of the dildo in place at my rear. Kristina brought over a laptop and set it down on a table in front of me.

“OKay, Paul, tell me what you see.” She said, giving me a second to observe her screen.

On the screen I could see what was clearly an email, with my photo attached to it. The body of the email had my name and address clearly typed out. “That’s the photo, on an email.” I said, panicking again. “Who is that to? What are you doing with that?”

Right now nothing. But in a moment I’m going to click a button and begin a program running that will attempt to autosend this email to everyone in my address book, every twenty seconds.

“What?!” I wasn’t sure who was in Kristina’s address book, but I knew I didn’t want that picture of me to be sent to anyone but her.

“Don’t worry just yet, because I’m giving you a way to stop it.” Kristina bent low and slid something to the front of my right foot, it felt a little like a small kick-pedal from a drum set.

“Feel that pedal at your foot? Well right now that pedal is wired to the fucking machine beneath your chair and connected via wifi to the laptop. When you push that pedal with your foot, two things will happen. One, the autosend will be cancelled, two the dildo positioned at your ass will be pushed deep into you. Don’t worry, I selected a size that will be suitable for a beginner like you, but it will reach much deeper than that tiny plug I gave you. Do you understand?” I did understand. I would have to hit the pedal to stop the email going out, but that would also be sacrificing my own ass to the dildo.

“Yeah, I do.” I said.

“Good, when I hit send, you’ll have about twenty seconds to cancel.” Kristina pushed send on the email and I saw a message box pop up. ‘Are you sure you want to send this email?’ Underneath that were the two options ‘Yes’ and ‘No’ with the ‘No’ option highlighted and a small countdown which currently had nineteen seconds and counting.

I watched as the countdown got to ten seconds. “You might wanna push the button, Paul.” Kristina said.

I grit my teeth and slammed down on the pedal. “OoooOOOooHHhh.” I instinctively tried to jump out of the chair as a noise I had never made before came from my mouth. The straps on my thighs kept me pinned in place so I could not escape the penetrating rubber cock.

“Hahahaha, the first one is always the worst.” Kristina laughed at my reaction while I felt the dildo sliding back out of my ass, a little slower than it went in.

“You’re telling me!” I shivered as the aftershock of the sudden intrusion rippled through me. A quick glance at the laptop screen showed me that the message was back up, but with the timer reset to twenty seconds, once more counting down.

I watched until the timer hit ten seconds, and clicked the pedal again. “Ahhh, fuck.” I moaned at the intrusion, the girth of the dildo wasn’t anything too massive, and it was very well lubricated, but it was longer than the plug I had been wearing, reaching new depths.

Ten seconds left, I hit the pedal again.

“You’re doing well, Paul. I’ll leave you to it for a while. Enjoy yourself.” Kristina left the room with a smile that suggested she was expecting something.

A few minutes and a few carefully timed pedal clicks later, I was definitely starting to feel the start of something different. It was a feeling I wasn’t used to, and a part of me hated to admit it, but I was starting to feel a light buzz of pleasure every time the dildo was pressed up into me.

It wasn’t long before I realized that I had just stopped paying attention to the timer and was pressing the pedal in a rhythm.

“Ah, ahh, ah.” I was moaning a little as the dildo pumped in and out of me, I was feeling incredibly horny and frustrated at the fact that I couldn’t touch my cock. It almost felt like an orgasm was right there but I just couldn’t reach it. For a split second, I actually thought that I might need a bigger dildo to help get me there. But I quickly pushed that thought aside.

“Having fun, Paul?” I hadn’t heard Kristina come back into the room.

“Ah! Kristina. I…..” I clicked the pedal again. “Ahhh, God!”

“Hahaha, I’d call phase two a success.” She said, reaching towards the laptop and deleting the email altogether, stopping the program.

“No!” I cried out as I pushed the pedal, only to feel nothing happen.

“Aww, were you getting close? Did you want me to leave you here fucking yourself in the ass for a while longer?”

“Uhh, I guess I was just getting into it.” I replied. “So, you said that was phase two, what’s phase three?”

“Phase three is me fulfilling your fantasy of getting pegged. But that will have to wait for now.”

So Kristina had decided that I was going to be pegged at some point. After my experience with the automated dildo I was beginning to think it wouldn’t be such a terrible thing after all.

Kristina released me from the chair and allowed me to get dressed. I was told she had a client coming over so I would have to leave. Not that I was complaining at that, the experience had left me in desperate need of a relief, and of course Kristina had figured out what I would be doing when I got home.

The only thing I could think about as I walked back into my home was Kristina, wielding a strap on and my desperate need to cum. Unfortunately, there was one more surprise in store for me.

There was a small slip of paper that had been posted through my letter box waiting for me on the floor. I bent to pick it up, the first thing I saw was the photo of me in the panties stuck to the bottom of the page, with Kristina’s handwriting above it.

‘Paul, I would imagine you are probably very horny right now and intend to play with yourself. But I have another task for you. I want you back in chastity immediately. Lock up your cock, with no release, and post the key through my letterbox within the next ten minutes, or this photo might find its way somewhere else. I’ll be waiting for that key. X

PS, don’t worry, you won’t have to stay locked for long this time. I just need to keep you horny.’

Dammit! Now I wouldn’t even be able to relieve myself. One thing was obvious, Kristina seemed determined to make sure I enjoyed the impending pegging. She seemed more interested in the idea than I was, I couldn’t help but wonder why.

End part 8.