Holidays Ch. 01

INTRODUCTION

I have been a kinkster for a long time and while male, I like to dress in heels and skirts in a masculine style. My default heel height is about 5", which for a man is about what 4" are for a woman. I enjoy bondage and pain both giving and taking and also penetration of all three holes. I make good money and am due some leave, so I go online and look for a holiday option to escape the real world and enjoy kink for a bit.

I find an offer for a bondage retreat and book 2 weeks there, giving them the option to extend it at their own cost if they like me. Given the money I have to shell out, I hope they do. My job is prewarned that I might stay away longer. After filling in a long questionnaire and paying, I am told that my travel arrangements are in place and what to do. I am sent a chastity belt with three steel cables, an anal opening and a long urethra tube that I have to wear. There is no key for the lock. At the front is an electronic device that connects to the sound and that I have to partner with an app that I download to my phone. Also in the box is an electronically controlled butt plug which pairs with the same app. It has no external controls. Both charge contactlessly, failure to keep them charged will be seen as breach of contract and it will be cancelled without refund. The chastity belt arrives the Friday before I travel, and included are instructions to put it on immediately. The last item is a corset that I am to wear 23/7 all week in order to get used to it and be able to close it on travel day. It has a pronounced ice cone shape and shoulder straps.

I lace myself into the corset and have 5cm left when I lace it as tight as possible. I take some sterile lube and lubricate the very long urethra tube (it is about 1cm short of my bladder - I had to measure) and start inserting it. OMFG that feels so good. I focus on work for a bit in order to be able to get my dick into the tube and then lock it on. One week of no wanks or sex ahead. The instructions also mention that I need to pair the device with my wifi. And I am to insert the butt plug whenever I leave the house (ie leave wifi range). If not, I get shocked in the urethra. The first time I go shopping I do this and the plug inflates itself to a point where it cannot be removed as I leave the wifi range. Oooof - walking just got a lot more interesting. Also the urethra vibrates in a most pleasing manner and the app says "good kitty!". I had not expected play to commence so early. I am also quite frustrated from the 'reward'.

Later that day the app orders me to bed and zaps me as I stay up. I learn that it can check your orientation - horizontal or vertical. It also has opinions on when I need to get up. Grrrr.

The instructions say to last eat something Thursday evening, so that I can spend Friday excreting and then be empty.I also am to get my nails done on Thursday. An appointment with my regular salon has been made and I receive long extensions with scarlet shellac and the same colour on the toes. The plug I am to insert once empty, but at the latest before I leave the house.

My travel clothes are to include the corset with the tight shoulder straps added, laced to a rather stringent waist (which I just about achieve after that week's training), a skirt, no underwear and the highest heels I can walk 1 km in.

PREPARATIONS

After a few days of rising frustration, I get up on Friday morning, shower and start putting on the corset that I am under orders to keep lacing tighter during the day. It is an ice cone shape with a slight wasp under the ribs and shoulder straps. I am to pull the shoulder straps as tight as possible and then lock. Aas I do this, my phone vibrates and the app tells me to put on flamboyant makeup, so I do as told. I log into work and try to do a normal day's work, taking breaks to go to the toilet and and to lace the corset tighter. Focussing on work is not easy due to my increasing excitement and anticipation. The chastity belt with the urethra sound does nothing to mitigate the issue. I am also already wearing my high heeled boots, since you cannot put on boots after putting on a corset.

After work I insert the plug in my now empty insides and notice that this time it clicks to the anal opening of the chastity belt. I have no way of disconnecting it again. I also had been sent a box that I so far had not been allowed to open. Once I logged into the app, my buttplug gave a short shiver and went quiet again.

The app displays the instruction to open the box. In it is a steel collar with an attached box and two electrodes protruding on the inside. Also in it is a stiff 3.5" curved posture leather strap that seems to be intended to go under the collar and has holes for the electrodes. A note in the box says to also pair the collar with the app. I do that and the app displays instructions to match up the collar with the posture strap and put it on. It clicks into place ominously, the lock being by the box and clearly controlled by it. When the lock shuts, it gives me a mild shock and the app displays a note that I am not allowed to speak, or the collar will shock me. So what, I am wearring two of those infernal remote control devices now?? Also, the butt plug inflates a little, just to make things a bit more interesting.

As mentioned, I am already wearing a pair of open toe, lace up, knee length boots with 5cm platform and 18cm stiletto heels and now add a kilt, which, when belted over the corset, makes for a very interesting silhouette, a medieval shirt and a hood to cover the collar. Have you ever tried getting dressed while wearing shoulderstraps and a posture collar? It's not easy, let me tell you! I had been told not to bring any luggage, everything will be provided. I apply lipstick and put it in the kilt pocket, so I can keep it topped up.

THE JOURNEY

I am to travel by public transport and so make my way to the station, somewhat hampered by my outfit and the plug. As I leave the house, the phone vibrates and the app displays a message to walk properly on a straight line putting both feet on the same line. I am already as upright as can be what between shoulder straps and posture collar, so I take pains to walk propery as well. I am to be there at 18h at the latest, but not before 17:50h. Once there, the app will display which train to take and provide a ticket and seat reservation. On the way to the station, I get a few whistles and compliments from women. The first time I try to reply I get a solid shock from the collar! No politeness for kitty! I arrive at 17:45 and walk into the station, only to get an even worse shock from my collar AND by chastity belt. My knees buckle. My phone vibrates and I check it. The app displays "you are early! Bad kitty! Wait outside until it is time. This infraction has been added to your punishment record."

At 18:00h the app displays which platform to go to and where to stand, waiting for the train, which arrives shortly thereafter. I go through the barrier using NFC from the app and, as the train arrives, I board and find my seat in first class. When I sit down the butt plug suddenly starts inflating further, to what I hope is its full girth. Which is quite a lot. This certainly is getting interesting! I do not know where to get off (both from the train and otherwise). After several hours a mild shock informs me to look at the app and am told to get off at the next stop and go to the bus stop. I get up early, and walking with the fully inflated plug certainly turns out to be as exciting and difficult as I feared. My erection being contained in the tube and pushing against the urethra tube only adds to my excitement.

After a few steps the vibrator in the plug comes on, and a moan escapes me. This lead to a strong shock that nearly makes me moan again. The app displays another notification that this has been added to my record. I collect myself and walk on as if nothing was the matter. When I reach the bus stop, I am informed by the app which bus to take. It is leaving in 45 minutes, so I head to the waiting area and sat *SHOCK* I jerk up again.

A message on the app informs me that I am to stand at attention (not stiff, but legs together like you're supposed to when wearing a skirt) and wait for the bus. Parade rest is not allowed. That is going to be fun in my heels! Also, standing still with the vibrator, which had now switched to a random pattern, will be even more interesting.

As I stand there, waiting for the bus, I notice a woman gently making her way towards me in what are clearly Pata heels. She is wearing a niqab and the shape indicates that she might be gagged underneath it. A light summer dress that is tailored to an ice cone corset, probably a posture collar and short ankle boots with pata heels conclude her outfit.

I politely nod to her and feel my plug inflate further. Deep breaths, kitty, deep breaths (but there is the corset)! She stops and looks like she is being shocked until she stands next to me in the same position, our elbows touching. In her heels (which are slightly higher than mine are, without platform (!) she goes about to my ears.

A short while later a very tall woman in a calf length pinstripe mermaid skirt, which is so tight that the knees can barely come apart, gently saunters up to us. The skirt is very high waist and appears to have a waist cincher built in. She is wearing a patent leather bullet sports bra as a top and a pinstripe spencer, as well as a very high neck corset that goes beyond the base of the skull at the back. On her legs are pony ankle boots with a locked ankle strap over fishnet stockings with seam. From the sound of her steps there are horseshoes on those boots. The size of the woman indicates that this woman might not be one genetically. Their tits are glorious though. They also step into our line, apparently with some prodding in their nether regions and checking of mobile phone.

The last arrival before the bus is due is a man of the surfer type, who is wearing PU shorts of the butt cheek splitting type, with a visible bulge in front that seems to indicate some kind of chastity device and probably a shocking device too. A small bulge also indicates the presence of a butt plug. His top is a short net shirt and he is wearing fishnet leggings over bare feet. He is rather a yummy muscular surfer type, including the shades which haven been pushed up into the hair. Around his neck is a heavy padlocked chain - not tightly, but too tight to be able to be pulled over the head. He is wearing a holster bag where his mobile is. He gets directed between me and the shorter woman, reaches out with his hand, pulls me down to him by the ring of my collar and snogs me deeply, which I return with interest. This appears to be allowed? He then steps into his correct rank on the other side of the shorter (and probably only) woman. I turn to the woman with the niqab and want to reach for her, when I get a solid shock in my dick. OUCH! So clearly no snoggings for me.

A few normal passengers have also arrived and are looking at us with appreciative eyes. Their attitude indicates that they seem to be used to weirdos showing up and taking this bus. The bus arrives and turns out to be a low floor 'kneeling' bus, which allows our handicapped selves to get on, if not easily for the wearer of the hobble skirt whom I have to help board - nice opportunity to cop a feel of their butt. The drive takes a solid amount of time, I cannot say how long since my vibrator came on again and I and, from the looks of it, my fellow passengers, spend the journey in a blissful daze.

Arrival

Eventually I get a medium shock that makes me regain focus and I see that we are pulling up to a gate lodge that is in what seems to be an endless wall around a country estate. We get off - the others clearly also having been shocked - and the door of the gate lodge opens with a woman wearing a PU sports bra with bullet cones over butt cheek PU leggings with a crotch zip and ballet wedge boots waving us in. The leggings are of the camel toe kind, showing her labia.

"Welcome to The Summer Camp! I am Paula and a fellow inmate. You will address me as Donna Paula for the time being." She says. "We'll prepare you for the last step of the journey before you walk up to the house." She leads us to a room, where 8 one bar prisons are anchored in the floor. "Stay here!" she orders, while she reaches under the first woman's niqab and seems to be getting hold of a ring by which she pulls her to the first pole. "Bend over!" The woman eagerly obeys and Paula pulls up the skirt of the dress, revealing a venetian chastity belt that shows a vaginal plug and an anal oping into which a butt plug is locked, very much like what I am wearing. She removes that and orders "Fatima, you can go upright again. Now step here," pulling Fatima into position over the bar and, after lubricating it, starts raising it, clearly inserting it into Fatima's bumhole as far as it will go. She tightens the thumbscrew that is out of the occupant's reach, leaving Fatima nice and impaled and incapable of moving from her assigned spot.

"OK, next. Tom!" The surfer gets grabbed by his chain and directed to the next pole, where he is ordered to position his heels on a steel pipe that makes him stand on tiptoe. He then also has to bend over and his crotch zip gets unzipped and the butt plug - the same as mine - gets deflated and removed. The pole gets inserted and arrested, fixing him in place.

Now it is my turn. I get grabbed by the ring of my collar, directed over the pole and ordered to bend forward. My plug gets deflated and removed, making me feel both relieved and disappointed. I then get directed over the pole and impaled on that rather big dildo. I sigh conten- *shock*.

"Yes you silly kitty, you are still not allowed to make a sound." Paula tightens the thumb screw on my pole and moves over to the tall woman. Standing impaled with no ability to get off the impaling device due to wearing heels is a weird and arousing feeling.

"Alright Sam, you, we will have to get you into a different outfit. Strip please!" Sam strips and neatly folds their clothes, handing them to Paula. We see that Sam, who has both a penis and glorious boobs, is wearing a chastity cuff that has holes for the balls, so they are separated to the sides. There is of course also a shock unit attached. That must have been interesting with that tight skirt. Paula puts the clothes onto a table and orders Sam to bend over, removing yet another one of these butt plugs. They then also get impaled on the bar.

I note that the dildoes on the bars are of different sizes and remember that that was a question we had to answer. Paula comes back with a corset that is quite similar to mine and starts lacing Sam in. She looks up:

"Oh sorry guys, I forgot something!" She walks over to the table and picks up a rather small wrist cage that has a chain attached to it. "Fatima, please put your hands on your back!" Fatima obeys and Paula expertly cuffs her, attaching the, clearly premeasured, chain to the back of her collar, so that, while being in a very comfortable position, her hands are in the small of her back and cannot reach her backside. Paula snogs her deeply and fondles her tits, then picks up another, rather bigger, cage from the table and walks over to me. I already have my hands on my back. "Good kitty!" she says and restrains me in the same way as Fatima. She then snogs me and pinches both my nipples. It really is very comfortable bondage, but I do feel more helpless and vulnerable, which is of course exactly the point. My cock is straining its confines in the tube of the CB, while pushing against the urethra sound, creating a fantastic feeling. I am so horny. I have been locked up and increasingly excited for eight days now...

Tom gets exactly the same treatment as Fatima and with that Paula returns to Sam, cuffs their hands in front and continues lacing them in. Enough time has passed that their body had a chance to get used to the corset and it can be tightened. Sam is then wrapped in a sleeveless and shoulder free leather dress. Paula transfers Sam's hands to their back and also chains them to the collar.

"Stay here, you lot!" She walks to the door and flicks a switch, which brings the plug in my butt to life, and judging from the others' reactions, theirs too. She leaves the room and us to our own devices. After a bit, my dildo even starts thrusting. I can't help but moan and notice that I don't get shocked. Soon we all are moaning and eventually screaming with orgasm. Well, -ish. As I approach orgasm, a ring around my penis tightens, which together with the urethra sound that goes past my prostate, makes it impossible for me to ejeculate, which is how one gives men multiple orgasms.

So I keep having smaller orgasms. It seems that that infernal control device that Paula attached counts orgasms, because the stimulation reduces after 5 of them. I am sweaty and weak kneed, but still have to stand straight and at attention over the one bar prison. As I come to my senses I notice that the others also seem to be settling down. We all are sweaty and panting, Fatima seems to be having a somewhat difficult time under her niqab.

On we go

"So, are we all refreshed? Your electronic gags are active again. I will make a few modifications to your outfits and then you can be off to the house." Paula says as she comes back in. She removes Fatima's niqab. Fatima turns out to be a complete stunner. I see that there is a transparent plastic pipe sticking out of Fatima's nose.??? She is also wearing a panel gag that is locked over the panel. How utterly humiliating. She opens the padlock and unbuckles the gag before carefully removing it. It turns out to be a ca 20cm long transparent penis gag. Wow! I now understand that that plastic tube means that she is intubated through her nose. Fatima had effectively been deepthroated for the whole journey. I am soo impressed and even hornier. Fatima notices me staring openly and winks at me. I melt and want to take her there and then - not that there is any hope of that.

As the gag is coming out, we see Fatima struggling to swallow all the drool that had accumulated in her mouth. Paula deposits the gag on the table and picks up thigh bands which she connects to the chastity belt and to the crotch piece of the belt with a very short steel cable. This has given Fatima some time to swallow the drool and work her jaw for a bit. Paula wipes her face, again kisses her deeply and also gives her some water to drink. I realise that the niqab must have had something to prevent all the drool from leaking. Paula then picks up a ring gag with a tongue depressor that she fits tightly into Fatima's mouth. She then starts doing Fatima's gorgeous smooth and long black hair, brushes it sensuously and puts it up in a high ponytail. The strap from the gag is arranged precisely in her neck so as to look pretty. I am getting a hard on again and really want some alone time with Fatima.

Paula moves on to Tom and applies an identical gag and also brushes his hair. She applies a pair of cuffs above his knees and chains them together with a 4" chain, effectively hobbling him. She moves on to me and gives me the same treatment with gag, ponytail and thigh cuffs connected to the CB. That gag is drool inducing, let me tell you! Sam gets the same bondage as Tom, but their hair gets put into pigtails.

Moving on

Paula takes a chain of maybe 1.5 metres length and locks it to Fatima's posture collar. She lets the bar down and leads Fatima out of the room. A moment later she comes back and takes Tom. Then it is my turn. As I step out of the gate lodge, I see the two others, Fatima chained to a golf cart and Tom's collar chained to the back of Fatima's. They are moving us in a coffle! I am getting yet another erection. Paula chains me to the back of Tom's collar and shortly after I feel a chain being locked to the back of my collar, so Sam is now clearly also here. Walking in these boots is certainly challenging, especially as I get shocks when I don't walk fully upright or don't put my feet in front of each other.