A Hole in The Fence

The following story will not be for the frail hearted. This first segment will start off slow and introduce the characters, it will have themes of chastity and bondage, incest, along with trigger warnings for SA.

For the story in its whole, I plan on this being a hardcore BDSM story. There will be focuses on chastity, BDSM, incest, public humiliation, sissy, crossdresser and transgender. I am open to adding other themes but this will not be you average hesitant to get on board story where they beat around the bush to get to the fucking.

Feedback is always welcome.

Have you ever seen the commercials where a guy is walking down the street and he hears a group of people chanting... "15...15...15...15...15" and out of curiosity he goes over to the fence to take a look at what could be going on and gets a finger to the eye for his curiosity only to hear "16...16...16...16" to add insult to injury? This story plays out a lot like that.

In the summer of 2023, I was walking home from college one day and decided to take a scenic route, passing by all the stores on the front of the street trying to sell all their wares to passersby's speeding by while they stare at their phones rather than the colorful lights of the shops. I didn't often go this way since it was too easy to find some new little do dad that would suck up all my money for it to break 5 hours later. However, every now and again I would come through to peek into my favorite shop, the mystery store. It wasn't really a mystery, just a sex shop that sold all your normal wares, dildos, lingerie, "supplements" and the odd guy that is always there staring at the DVDs.

Now I know what you are thinking, what's a fine young man, that's 6'2" and an even 180 doing in a place like this when he could likely swing any woman he wants. I'll tell you, it was the mystery box, the thing this place was known for. It was a big luggage trunk and was marketed as a mystery, it could be anything, sex toys, a blow-up doll, a dead body, a day-old pizza. It was much more likely to be a sex thing than that last one, and hopefully the one before that. However, the mystery still stood. I had come here about once every month with the desire to buy one, just for the ability to say I had bought one and seen the day-old pizza inside. There was just one problem, well two problems. The first was the price tag, a whopping $1000 just for the pleasure to open the box and get disappointed. The second was my roommate, she was the ultimate evil bitch, constantly on my nerves, and never stopped bugging me... my mother.

My mother is what you would likely call a MILF, yes I know its overplayed, and too many old women on Instagram call themselves MILFs when in reality they are most definitely not. However, I can objectively say that my mother is a MILF, and it's because she is only 14 years older than me. That's right, she got knocked up by her father at the age of 13.5 and had me shortly into being 14. It's a sore subject in my family, leading to lots of awkward stares at Christmas time. Enough said to say we don't spend a lot of time around any family and stay secluded on our own a few states over. Now however mom is only 33, about 5'8" and has a gigantic pair of natural 32DDD's that she loves to bounce around the house with. Add that to the unresolved trauma (psych major) from being molested as a child and now she is a fully sexual being just as Freud would have wanted. In general we have a really good relationship with only 1 draw back, she doesn't understand boundaries. She will freely enter my room, dig around for stuff in my closets, and cause general mayhem. She doesn't do this to snoop mind you, she is cleaning, or put stuff away (despite telling her she no longer has to) and is just generally oblivious that I am trying to keep sex toys and porno mags in my room.

Now you can understand why I am hesitant to get this giant trunk of hopefully sex toys that I wouldn't even be able to hide in my closet. When I walked into the store after checking to make sure nobody I knew was on the street the regular girl who worked at the counter noticed me and waved for me to come and say hi. Her name is Riley, and she has always been very nice to me, even offering me her employee discount for the mystery chest of toys so I could get it if money was the only thing stopping me. She was a nice enough person, not really my type on account that I was 80% sure it was actually a dude.

"Hey there Jake, come to stare at the box again?" she said in a suspicious falsetto chirp.

"Oh, you know Riley, I like to know what's in the box before I buy it. Make sure its worth all the money I would have to spend on what I'm sure is actually just a day old pizza from Tony's." I quipped back. It was an old habit of ours, a call and response if you will about saying hello how are you in less words. After all she was always here when I came in and we made friends fast on account that I am 85% sure that she wanted to get fucked by me... or maybe fuck me?

"I got a secret to tell you but first you have to get old man Jenkins away from the pornos and out of the store. Once you have him out come on to the back and take a look at what I just got in." As she whispered this to me, she turned off the open light, and gestured vaguely to the mystery box.

After telling old man Jenkins that the shop was closing for a lunch break, he grumbled and set down a copy of Horny Slutty Vampires 3 (Honestly I think Horny Slutty Vampires 3 was just a worse remake of the second one and without Riley Reid as the main character but what do I know). As I threw the deadbolt across the door I ran to catch up with Riley (No affiliation) to see what she wanted to show me and hoped it wasn't a dick. Or at least not a dick bigger than mine.

When I walked into the backroom, I saw what looked to be a mystery chest, but a bit bigger than what I normally came to expect and shaped oddly like a full size dresser. Riley slapped the top as if she was a genuine jalopy salesman and started telling me about how many miles to lemon lawsuit it would get.

"This here is our newest lineup and I think you will like what you see. I would like to introduce the Mystery box lite, or as I like to call it the sissy box for all you little sissies that still live with families and don't want anyone to know about their little kink box like we have out front." She said this mockingly and grinned at me. She liked to joke with me at my expense but in this instance I didn't care, it was now possible to buy this and hide it from my mom.

I was immediately hooked, it looked exactly like (shush I'm a guy it was brown and brown = brown) my other dresser and the possibilities immediately started flooding my mind about how I would get this thing home. I think Riley could tell since she just gave me a smile and said "delivery included". It took me all the cash in my wallet ($40), maxing out my credit card ($750), a spot from Riley ($110) and her employee discount (10%) but you bet I bought it, with assurances it didn't have a pizza in it.

"So here is the deal, the way mystery boxes work is that it's a slow progression. They cost a lot but its because this is months of stuff not just 1 day. So when it gets delivered to you tomorrow, the first thing you need to do is get rid of your old dresser, put all your clothing into this one and give your old one to the delivery driver who will take it to salvation army for you. The next thing you need to do is activate the app and link it to the node in the sock drawer, it will release products stored in the false back of the dresser into your drawers at set intervals and based on your activity and progression. The items included in the dresser are completely random but is specific to your gender. You won't get a bunch of women's lingerie or dildos when you're a man. If you have any questions don't be afraid to ask me, and don't forget to bring me that $110 you owe me." She yelled out that last part since I was already skipping home in my haste to get to bed and prepare for my new debauchery hidden from the every prying eyes of my mother.

Chapter 2: In plain sight

The next morning was Saturday which meant that mom was still asleep in some guy's house and wouldn't be up to suck him off until at least noon. Later if she had tequila instead of vodka. It was about 9a that the truck driver arrived with my dresser and helped me drop it in my room and took out my now empty dresser to send to Salvation Army to destroy the evidence that I had gotten a replacement. My god it looked beautiful, standing there in all its sexual glory. I stood there staring at its wood for 1 second less than was gay before I downloaded the app and went through the set up procedures. After about 3 tries to get it to find the node I realized that it needed to be plugged in, for the machinery *slaps forehead*. Once it was plugged in it connected without any issue and the app loaded right up. There was only one button, nothing else and it read "Start your journey".

At the time I had no idea what I was doing, no idea what those three little words would mean for me. At this point you might be saying don't push it stupid, or even maybe you deserve what's about to happen for being stupid. Major spoiler, I pushed the button.

***HELLO, WHAT IS YOUR NAME?***

The app read like an old cathode tube monitor from fallout, who decided war games WHOPPER style was the best possible user interface should have been shot.

*I AM JAKE*

***

HELLO I AM JAKE,

I AM MYSTERY BOX YOU MAY REFER TO ME AS MB

I AM HAPPY YOU HAVE DECIDED TO START YOUR JOURNEY OF DEBAUCHERY

PLEASE ENTER YOUR SAFEWORD

***

I was frowning and irritated, such a simple programming error and it decided to run with it. I would have to be more careful with how I interacted with it to avoid issues in the future.

*Strawberry*

***

EXCELLENT, LETS BEGIN

FOR THE FIRST DAY WE SHALL USE THE BUILT IN PENIS SLEEVE, SIMPLY ALIGN YOUR DICK WITH THE HOLE IN THE SIDE AND THE MACHINE WILL SUCK IN YOUR FLACCID COCK AND BEGIN TO MASTURBATE IT.

***

Now I was curious, this dresser was wide as I am, allowing me to barely wrap my arms on the right or left of it which makes sense since it has both my clothes and the machinery in the back. On the top of the dresser it came to my armpit, allowing me to rest my arms on top of the dresser where I noticed two handle like protrusions on the top placed perfectly for a person to grab it from the side. I stuck my dick in the hole, felt the suction take my dick into a tube and begin to hold it. I waited for it to begin but it didn't start, when I looked down to my phone the interface displayed only one line of text.

***GRAB HANDLES WHEN READY TO START***

So, I did, and at once half circle restraints snapped closed around my wrists locking my hands into place. The sucking started, but not on my shaft where I thought it would begin, instead it pulled more of my 8" cock into the tube and eventually swallowed my balls two. At this point I started to panic and looked at my phone.

***REMAIN CALM***

Fat chance that's happening. It was at this point the sucking stopped and instead I felt a solid ring resting around my balls and shaft before the tube began backing out and letting my balls go only for the tube to be pushed right back into the ring that seemed to be supported by the machinery still. I heard an audible click and a snap before something cold and slimy was pushed against the tip of the cage and then started touching the tip of my penis. What happened next is how I imagine women feel when you stick it up their butt without warning. Since this narrower and slimier tube was pushed into my dick and just kept going. I felt it burning at first, then tickling, then my knees began to shake, and it finally rested deep up in my belly.

I would like to say that I hated the treatment, that I was scared, humiliated, vulnerable. However, at the time the only thing I could focus on was the intense feeling and desire to cum, along with the complete inability to get hard. Finally, the wrist shackles released me, or rather the narrow shackles were released from the dresser, and I was able to pull away from the hole that had my dick trapped. What I saw shocked me, a metal thing on my dick completely wrapped up and squished with my big balls sticking out he bottom uncomfortably tight.

As I mentioned I am 8" hard but am definitely a grower, only managing 5" soft and the thing I had in my hand had to be less than that. I looked for a screw or a something that was holding it together only to see a flush screw with three little dots instead of normal head. I hadn't ever seen a screw like that before. The cage was a bright blue and while it was heavier than nothing it was still relatively light in comparison to what I thought a chunk of steel would weigh. At the head there was a little twist cap which I pulled on only to feel a tugging sensation deep in my gut. I unscrewed it instead only for piss to come flying out. I tried to screw the cap back on but only succeeded in making a bigger mess of my sheets before finally getting the cap back in place. I picked up my phone to look at the app and all it said was:

***

Set up complete,

Cage stage 1: 5" installed

Catheter: Balloon lock successful

Quick restraints: Permanently locked

***

When I tapped next the app closed. When I opened it again it simply said

***

Next step in 2 days

***

I sat on my piss soaked bed buck naked and facing my door wondering how this day could get any worse when my mom walked in... 16...16...16...

End of part 1