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Ed Kilpatrick’s
Island Adventure – Part 2
Introduction:
In part one of my island adventure we met two fictional characters:
Sadly Peter had died 6 months before Dan’s forced landing in Eigg and this set off Dan and Ailsa on a journey of discovery to try and establish the old house as a kinky B&B and hopefully a sustainable business.
As Dan and Ailsa got to know each other on that forced weekend together, they realised that they had a similar taste in cross-dressing, masks, bondage and being locked-up for periods of time. It was only when Dan prepared to fly home on Monday morning to set-up a website for Ailsa’s business, did he find himself being locked into a chastity tube at the hands of Ailsa, who wanted to ensure his faithful return on the following Friday.
Back in Lanarkshire and a business to set-up:
I arrived back in Lanarkshire less than two hours after leaving Ailsa’a place on Eigg. I took some stick from the CFI (Chief Flying Instructor) about taking three days to do a four-hour return flight. Little did he know the fun I’d had during my weekend of discovery? We did make arrangements to fly back to Eigg on Friday morning (weather permitting) so he could bring back the Caravan and put it up for sale. Back in the car, I wasted no time in calling Ailsa:
“Hello Ailsa MacDonald speaking,” came that beautiful island accent answering the home phone.
“Hello my dearest,” I teased as I drove home towards Bothwell.
“Ah you made it back to the mainland Dan,” asked Ailsa?
“Of course I did Ailsa, what did you expect,” I laughed? Surely my flying isn’t that bad, I thought to myself?
“So are you missing me already,” asked Ailsa?
“Of course,” I replied. “Are you missing me?”
“Naturally Dan but remember, I still control you,” teased Ailsa.
“How could I forget,” I sarcastically responded. “Every time I think about you and the fantastic weekend we’ve just had, my dick brings me down to reality!”
Ailsa just burst out laughing on the other end of the phone and told me that was her goal.
“I’m going to start on the website when I get home Ailsa,” I explained my plans. “Tomorrow can you take as many digital pictures as possible and mail them to me?”
“No problem Dan but where do you want me to take the pictures,” asked Ailsa?
“Please only take pictures inside the cell-block and interrogation suite,” I replied. “I’d rather try to keep the exact location of your house anonymous and I have a plan to keep it that way. I’m sure that will add to the fun of our business plan!”
“Don’t you mean your business plan Dan,” teased Ailsa?
“It is your house Ailsa, your outhouse and your cells,” I sarcastically replied. “I genuinely want to help you promote it and if it becomes a successful business, then we can see where our partnership leads.”
“I know Dan and I trust you 100%,” responded Ailsa, feeling slightly guilty. “You don’t need my money so I guess you’re just trying to help a girl who has a tiny bit of control over your life right now!”
I then started to laugh, which then led to the usual I LOVE YOU before be broke the call and I finished my short drive home.
During the next three days I set-up the website and started the basics to market Ailsa’s fantastic facility. Ailsa started to e-mail me lots of photographs. Her broadband wasn’t keeping up so after a quick call to BT, I arranged to have her service upgraded by the time I arrived on Friday. By Thursday afternoon I had the basis of a website and several Google Ads directing web searches to our website. I even started some direct marketing of European groups and forums and soon I was receiving plenty of enquiries. It was exciting starting up a new business. I did it once before so I was confident I could do it again!
I wanted to add video to the website so seeing Ailsa was online via Skype, I gave her a call:
“Hello honey,” she opened the conversation as our PC’s connected and I saw her beautiful face on my monitor.
“Hello sweetheart, I’m still working,” I teased as it was now well after eleven!
“So you are Dan,” replied Ailsa who was lying in her bed. “Are you still wearing the belt?”
“How the fuck can I get it off,” I laughed?
“Show me,” Ailsa demanded!
I then stood up, unzipped my jeans and pulled down my boxers so Ailsa could see her hideous contraction that trapped my poor cock:
“Does it hurt,” asked Ailsa with a smile from one ear to the other?
“Yes but only when he tries to get hard,” I replied. “So now I’ve shown you my imprisoned cock, prove to me you’re wearing tights to bed?”
Ailsa just laughed again and then pointed the laptop and her webcam at her legs, which were clad in black Lycra.
“You love my legs don’t you Dan,” teased Ailsa?
“You know I do Ailsa,” I replied. “Anyway we have work to do so I plan to take some video on the weekend so I trust you’re prepared to be my wiling actress?”
“Of course,” responded Ailsa. “But only if my face is hidden!”
“That shouldn’t be an issue with your collection of masks and helmets,” I came straight back at her!
After a few more minutes, we said ‘goodnight’ and we dropped the call. I then packed a hold-all for my weekend away and popped the laptop into a bag for the flight tomorrow.
Friday morning and my trip back to Eigg:
I was ready to leave the house but as I went over to switch off my desktop PC, I saw Ailsa was online. As her PC connected, I saw she was wearing something weird:
“Good morning honey, what the fuck are you wearing,” I asked Ailsa?
I was referring to the red tartan hooded dress that looked heavy and probably uncomfortable in the summer heat.
“It’s my uniform,” responded Ailsa. “Do you like it?”
“Stand up and give me a twirl,” I requested?
Ailsa stood up in front of her laptop (I had to improve the camera she was using) and showed me the very tight long tartan dress. The bodice looked very tight and the hood was up and hid Ailsa’s entire head, except her face.
“Do you like,” Ailsa asked Again?
“Of course,” I replied! “I’d prefer to see you wearing something less but I guess when we have guests, you need a uniform.”
Ailsa sat back down at her PC and told me that she had a uniform for me to wear. I tried to get more out her but Ailsa was staying tight lipped until I arrived in Eigg later today:
“How frustrated are you Dan,” quizzed Ailsa?
“The fucking chastity tube is driving me insane,” I came straight back at Ailsa on this topic that annoyed me!
“Well you’ll be free of it this afternoon,” Ailsa reassured me.
“I’m glad to hear that Ailsa,” I gladly replied. “I’m off to the airfield now to collect John so please don’t wear anything that will give him a heart attack?”
Ailsa just laughed and we ended the call before I switched off my desktop PC. I threw my bags in the car, picked up sixty litres of unleaded on route to the airfield where John Cameron, the CFI was waiting for me:
“Are you ready to go Dan,” asked John?
“Here’s my flight plan John,” I threw him the paper plan. “I’ve got to fuel up and check the plane so give me half-an-hour?”
With the aircraft fully fuelled and checked over, John jumped on board and we discussed the flight before I started up the engine and taxied out for take-off.
As we climbed out of the Glasgow zone John and I settled into what should be an uneventful flight to Eigg, just over 100 miles away:
“Your flying is improving Dan,” complemented John.
“I’m glad you think so John,” I replied.
We chatted about what was needed for me to gain a license for a heavier aircraft but until I received the hours required, John and I set a hourly rate for him to fly the Caravan and any guests to Eigg. Within ninety minutes of leaving our airfield I was circling overhead Ailsa’s house and setting myself up to land:
“This is fantastic Dan,” said John as I eased the sport plane onto the black tarmac. “Let me guess there is a female involved?”
“And there she is,” I replied, pointing to Ailsa who was standing next to the open hanger.
“Fuck me mate,” replied John. “She’s hot! I can see why you’re so eager to get back up here!”
It was a bright day but not that warm in the north-western islands. Ailsa was wearing a short denim mini skirt over her normal black opaque tights and a black turtleneck shirt. The shirt was particularly tight and it made her tits stand out this morning. I parked the plane next to the hanger so that we could get the Caravan out before I popped my plane inside for the weekend.
“Hello my darling,” I threw my arms around Ailsa and gave her a kiss, which was well received.
“This is John Cameron from the airfield and he will take your plane back for sale,” I introduced Ailsa to John.
Ailsa shook John’s hand and we discussed the circumstances to sell the Cessna Caravan. John had prepared some paperwork, which we’d go over during lunch but first we got the Caravan out of the hanger, popped mine in and began to check the much larger aircraft over before we headed in to sign the paperwork:
“Do you mind if we take it for a spin Ailsa,” asked John?
“Of course,” replied Ailsa. “Dan would you go with John and I’ll make us a light lunch before John heads home?”
That settled, I handed Ailsa my bags and John and I jumped into the Cessna after checking the fuel for quantity and water contamination. With it all checked we started up the Cessna and headed up in the late morning sky to see how the plane performed.
“This should sell quite quickly Dan,” John confidently assured me. “Do you want a cut of the sale?”
“Nah,” I replied. “Just sell the bloody thing, take your normal 5% and we’ll call it quits!”
“You really do like this girl,” John started to tease as we set the aircraft up for landing.
“She’s lovely John,” I replied. “I’m helping her set-up her home as a B&B so I’m just happy to help Ailsa out and who knows what I’ll get in return?”
We both laughed as we shut down the Caravan and headed back to the house and kitchen where Ailsa was just setting the table for lunch:
“Great timing guys,” she announced as we all sat down to eat.
Lunch went on for an hour, where Ailsa signed the sales agreement for the Caravan and I walked John back to the waiting Cessna Caravan. As the aircraft headed into the afternoon sky, I walked back to the house and met Ailsa in the courtyard, wearing her uniform, the red tartan long dress, which now had a belt with a bunch of keys attached to a long chain and two pairs of handcuffs hanging on the other side:
Ailsa and Dan start another weekend:
I took hold of Ailsa again and placed my lips against hers:
“I see you’re prepared to accept a prisoner Ailsa,” I laughed taking hold of my now girlfriend and giving her a kiss she’d never forget.
It was then my cock started to grow again and the realisation that I was still locked in the belt, exactly where I’d been for the last week:
“Ailsa would you mind unlocking the fucking tube please,” I pleaded? “This is lovely but it’s killing me!”
“Come with me and we can see what we can do about it Dan,” Ailsa took my hand, leading into the outhouse and the interrogation room with the manacles hanging from the ceiling and the shackles attached to the floor.
The manacles were hanging lower than usual so Ailsa had no problems taking hold of my right wrist and locking into the heavy iron cuff. In saying that, I offered no resistance and soon both wrists were securely locked. Next Ailsa knelt down and locked both ankles into the shackles before walking over to the control panel on the wall and dragging the chain, the cuffs and of course my arms into the air, towards the ceiling:
“You offered no resistance darling,” teased Ailsa as she came straight back to me, kissing me once again.
“Why would I resist you,” I replied. “I’d do anything to get rid of the tube!”
Ailsa explained that she’d have to go back to the house and retrain the special keys from the safe:
“Don’t go anywhere,” announced Ailsa as she headed out of the room, closing and locking the door on route!
Where the fuck could I go? I was stretched with my ankles locked in the shackles and my hands were already getting sore in the manacles that held them high above my head. How long could I stand in this position? I had hoped Ailsa would simply go back to the house, retrieve the key and come straight back to release my cock. How wrong was I? I looked up at my watch and counted the minutes as they passed an hour before the door was unlocked and Ailsa came bounding into the room:
“I’m so sorry Dan,” she apologised coming over and kissing me. “We got our first booking!”
“When,” I asked?
“In three weeks,” replied Ailsa.
“That’s great honey but would you mind unlocking me,” I tried to turn the conversation back to my plight.
“Do you not want to hear the details,” asked Ailsa?
“Yes but please honey, unlock my dick,” I pleaded!
Ailsa just smiled and held up the special little key to my face:
“What’s it worth,” she teased?
“It’s your choice sweetheart,” I came straight back with a serious response. “If you don’t unlock my cock, I’ll be straight back on my plane this afternoon!”
“And how do you suppose you’re getting out of these shackles,” replied Ailsa?
I thought about my response a little longer than Ailsa or I had expected:
“I didn’t think so,” Ailsa broke the silence.
She then knelt down, pulled down the zip on my jeans, followed by the jeans and my boxers.
“He looks so secure,” Ailsa continued to tease!
“That’s because he’s so locked up,” I sarcastically responded.
Ailsa then stood up without unlocking my cock and starred into my eyes:
“Don’t be so cheeky Dan,” Ailsa growled! “At the moment I own you so just remember that I therefore own your freedom!”
“And I am enjoying the control you have over me sweetheart,” I continued to beg for my cock’s freedom. “You’re just so hot but that causes me quite a lot of discomfort!”
Ailsa just smiled and placed her hands on either side of my face before kissing me again. I said nothing as Ailsa broke the kiss and knelt down to unlock my cock from the steel tube that had imprisoned him for nearly a week:
“Thank you Ailsa,” I whispered.
“I can see he’s happy to see me,” laughed Ailsa as my cock embarrassed me right away by rising to his new found freedom.
“I think he is just delighted to be free,” I replied, delighted myself to be shot of the chastity tube.”
“Umm, what to do now,” asked Ailsa, putting her hand to her mouth in contemplation?
“You could free me from these chains and tell me all about our first guests,” I suggested!
“I could but I’m not going to,” replied Ailsa.
She was off again, this time leaving my trousers and boxers around my shackled ankles and my cock standing to attention for the first time in days. This time the door was left open so I guessed Ailsa was making the short trip to the storeroom so what was she up to? Ailsa was back in a few minutes with something hidden from view behind her back:
“I think it is payback time,” explained Ailsa who was now standing behind me.
My arms were tight so I couldn’t turn around with my ankles locked to the floor. I soon knew my fate as Ailsa pulled the PVC hood over my head, the same PVC hood she’d worn last Sunday when I found her masturbating.
“No Ailsa, please no,” were my last words before the penis gag was forced into my mouth and my world went dark.
Soon the hood was zipped up tight and I was breathing through the tube attached the penis gag that now filled my mouth.
“Now this is how it’s going to work,” explained Ailsa! “I’m going to get you out of your cloths so any attempt to struggle will force me to close the valve on your gag.”
Ailsa then did something to the valve, which immediately meant I was sucking hard for air.
“You see,” Ailsa continued. “I’ve only given it a quarter of a turn and now you’re struggling to breathe!”
She was right; I was struggling to breathe so I stood still as Ailsa undid each ankle one-by-one before locking them again (one-by-one) and I was naked from the waist down. By lowering the manacles, Ailsa soon had me out of my T-shirt and therefore naked except for PCV hood that encased my entire head.
“Now that was easy, wasn’t it,” explained Ailsa as she gave the valve another turn and therefore cutting off all my air. “But sadly no fun so you’re going to experience what you put me through last Sunday!”
I started to panic as I could no longer breathe. I screamed into the gag but little noise came out! By now Ailsa had used the controls to pull my body tight. I was struggling to stay on my feet as my arms were pulled into the air. Soon Ailsa was sucking hard on my cock and it was wonderful. She was right, this was a rush but never-the-less I was being starved of oxygen as I exploded in Ailsa’s mouth in seconds!
“Did you enjoy that,” asked Ailsa as she stood up and turned the valve, allowing me to breathe again?
All I could do was nod and MUMPTH into the gag.
“I’m off to get a drink,” laughed Ailsa, leaving me to hang in the chains I’d spent the last couple of hours in.”
I heard the door being closed and locked but other than that I heard very little and saw nothing! How long would Ailsa leave me this time? My arms ached and being stretched even tighter this time, I was struggling to keep my wits. However I didn’t have to wait long until the door was being unlocked and Ailsa returning. However was it Ailsa because I could see nothing and hear very little as the motor brought the manacles down so that they could be unlocked? I was disorientated as both hands came free. I should have brought both up to grab the mask but I didn’t, instead allowing whoever was in control to pull both arms behind my back and lock them into a pair of handcuffs. My ankles were next but at least they remained free as Ailsa finally spoke:
“Follow me,” she said in a relaxed tone as I was led out of the interrogation suite.
I hoped to turn left and back towards the house but not this time as I felt Ailsa tug mew to the right. I MUMPTHED into my gag but little came out and past the gag that filed me mouth. It was then we stopped:
“You’re uniform is lying on the bed,” explained Ailsa. “When I remove your cuffs, you can unzip and remove the hood yourself but please get dressed?”
I could feel Ailsa fiddling with my handcuffs, which were soon gone but then the sound of a cell door closing behind me, told me that I was probably locked in one of the prison cells. I reached for the rear zip on the hood and soon as I was free of the heavy PVC. I was spot-on; I was now locked in the cell I spent last Saturday night in and lying on the bunk was a pile of clothes, including a kilt. Now I’d worn a kilt to many formal occasions so this would be no hardship or would it be? As I checked out what else Ailsa was expecting me to wear as my new uniform, I would a pair of black leather DM boots on the floor beside the bunk and a linen long sleeved cream shirt. Next I found what I thought were cream woollen socks but as I picked them up, I realised that these were thick cream woollen tights. I guess this was Ailsa’s kinkier side kicking in! No sign of any boxers or pants so I pulled on the luxurious wool tights followed by the linen shirt. Next came the black, green and cream tartan kilt and finally the leather boots or so I thought). It was then I noticed another item of clothing so I picked it up to find a thick black woollen balaclava. As I pulled the heavy wool over my head I managed to find the mouth and two eye holes but this balaclava was long and I had to fiddle with the long neck until it was fitting comfortably around my neck. I then checked myself in the mirror and saw Ailsa’s kinky idea of a uniform for me. It looked great and felt great but how long would I last in the heavy wool during the summer? I’d no idea what to do now. I was horny but knew that taking things into my own hand meant pulling down the wonderfully soft women tights so to ensure self-restraint, I backed up to the wall and slipped each wrist into the open manacles. With a little difficulty, I soon had them closed and locked! I didn’t have to wait long this time until Ailsa returned:
“Ummm, you look so good it that uniform,” she complemented my new uniform as the cell door opened. “And you’ve even managed to lock yourself into the manacles!”
“I had to do some self-restraint honey,” I replied. “I’m glad you like this uniform because so do I, even though I’m not sure I’ll survive in the summer under all this wool!”
Ailsa then approached and we kissed:
“I’m sure you’ll survive Dan,” explained Ailsa. “My plan is that none of our guests will ever see your face!”
“That’s a novel approach,” I replied. “However I do see some logic in your madness.”
“But then Dan,” Ailsa continued, “I do like a man in a skirt and a mask!”
“I know you do,” I laughed!
We kissed again before Ailsa sat back on the bunk:
“So our first guests,” she opened the conversation.
“Yes, tell me about our first guests,” I replied, still manacled to the wall of the small cell.
“Their German,” replied Ailsa. “Two girls, Nicole and Heidi from Cologne: They’re walking the West Highland Way and will arrange to catch a ferry to Eigg in three weeks on Saturday.”
“Did they talk about their requirements,” I continued questioning?
“No darling,” replied Ailsa. “I’ve e-mailed the guest requirements form you and I prepared last week so I expect we’ll find out very soon.”
Ailsa then got up, took the keys from her long chain attached to her belt and unlocked my wrists before we kissed again:
“I think it is time to take some video Dan,” Ailsa set out her plan for the rest of the afternoon. “Let’s go back to the house so that I can get changed into something much more seductive and you can prepare the camera.”
Back at the house I remained in my new uniform, including the wool balaclava. With my digital SLR and HD camcorder, I headed back to the outhouse, taking some pictures on route. After setting up the camcorder in the room Ailsa had chained me in earlier, I set-up the SLR on a tripod and went back outside to take some video of the entrance to the play rooms. I had just stopped videoing when am image I’ll never forget exited the back door of the house:
“Nice outfit,” I laughed and wolf-whistled at Ailsa who was dressed in a black Lycra cat suit.
“Do you like,” Ailsa kept fishing for more complements?
“Of course I do, I continued to pay this beautiful girl some more complements.
Ailsa’s body was completely covered from head to toe in bright shiny black Lycra. The built in hood had both eyes and a mouth hole, not that different to my balaclava. I then set-up the video camera to take a shot of me escorting Ailsa to the outhouse:
“Before we start honey, I think you need to be restrained,” I set the scene.
“I agree,” replied Ailsa. “I’ll head into the store room and pick up so essentials.”
Ailsa was back in a few seconds with a prison set in her hands. I then knelt down and shackled her ankles before taking her arms and pulling them behind her back and locking Ailsa’s wrists into the cuffs. For the next two hours I videoed the Lycra covered Ailsa in every room, using every device and then in the cells with various restraints to the cage.
“Last one Ailsa,” I teased. “Time to get you into a straightjacket!”
As we headed back to the storeroom, Ailsa replaced the prison set while I picked up a white canvas jacket:
“I think this will contrast with your back cat suit perfectly,” I laughed holding up the heavy canvas straight jacket!
Ailsa offered no resistance as I slipped her arms into the long sleeves, turned her around and started pulling on the various straps and buckles very tightly:
“You’re enjoying this Dan,” laughed Ailsa as I started the process of feeding her arms through the front chest loop?
“You bet,” I replied as I hauled on each sleeve to ensure it was going to be very, very tight.
Before buckling the crotch strap I tightened the chest loop to ensure Ailsa’s arms were not coming over her head. I had plans to keep her in the jacket a little longer than she was expecting so I wanted to ensure escape was never an option. The crotch strap came last and then I led my little mad girl to the padded cell where I began the session be taking about one hundred digital stills. Next I set-up the video camera and videoed Ailsa struggling to free herself from the jacket, which of course was never going to happen:
“Are you enjoying yourself Ailsa,” I teased, putting down the camera to give my little bound vixen a kiss.
“Oh this feels so good,” responded Ailsa in a low seductive voice. “I’ve never felt this tight before, I love it!”
“Well sweetheart, you’ll then enjoy staying in here a wee while longer while I download the pictures and videos into my laptop,” I dropped my plan, heading out of the padded cell.
“Oh Dan, don’t leave me in here,” pleaded Ailsa as I slammed the padded door closed.
I ignored Ailsa’s pleas as I took the camera gear and headed back to the house. Removing the balaclava, I set-up my laptop on the kitchen table and began downloading the images and video. To be honest, I lost track of time until I noticed it was eight o’clock and Ailsa had therefore spent over two-and-a-half hours in the padded cell. I rushed over to find her sitting on the floor in a state of exhaustion:
“I’m so sorry honey, I forgot all about you,” I laughed as I help Ailsa to her feet.
“I’ll remember that, the next time I put you in a straightjacket and leave you in here for three hours,” grunted Ailsa!
“Two-and-a-half hours,” I sarcastically responded. “Anyway, you seemed so happy to be in the jacket!”
“Since you’re being so grumpy you can stay in here a little longer,” I laughed, pushing Ailsa back into the padded cell and slamming the door closed!
I headed back over to the house to make us both some dinner. Some simple pasta and a bottle of wine were taken over to the canteen area of the outhouse before I used the keys to lock the last set of barred doors. Ailsa was staying in here a lot longer than she would ever expect so after removing a really grumpy Ailsa from the padded cell, I led her to the canteen where she remained in the jacket while I fed her.
“You’re really enjoying yourself Dan arn’t you,” asked Ailsa between mouthfuls?
“Well if I’m to finish our website this weekend I’m going to need some peace and quiet,” I replied pushing another mouthful of pasta into Ailsa’s mouth.
“You’re not keeping me in here all weekend,” Ailsa started to panic?
I just stared back at her and smiled:
“You’ll stay in here as long as I want you to be here,” I teased.
It was then Ailsa stood up and tried to get away from me. If I didn’t know any better, she wanted to be chased! As you can imagine, I caught her easily and soon had her popped into the first cell we both spent a night in last week:
“You’re not going to leave me in the straightjacket Dan,” Ailsa really started to get concerned?
“If I let you out of it, will you fight me,” I tried to gauge Ailsa’s mood?
“No I promise to be good,” responded Ailsa.
“Okay then, kneel on the floor with your face towards the wall,” I demanded?
With Ailsa on the floor, I soon had her out of the jacket but before she could rush me, I was out of the cell and closed the door.
Back at the house, I continued working on the website until midnight. I was tired so before going to bed myself, I headed back to check on Ailsa with a glass of water and a cup of tea. As I opened the latch I could see my little friend was fast asleep. She was still wearing the cat suit and her face was still covered by its’ built in mask. I decided not to wake sleeping beauty and headed back to the house to get into bed myself.
Another Saturday and more web development:
Before any of you ask, I was really boring on Friday night. I simply removed my kilt, shirt and of course those think woollen tights and climbed into bed naked. I guess Ailsa would be disappointed but to be honest, she would be none the wiser as I fell to sleep on my first night back on Eigg.
Saturday morning came far too quickly so at around nine o’clock I was up and about, having had my shower and slipped back into my own cloths. Breakfast prepared I headed across to the outhouse and after unlocking and re-locking several barred gates, I soon arrived at Ailsa’s cell:
“I wondered when you’d come back for me,” complained Ailsa as I opened her cell door.
She was still wearing her black cat suit but the built in mask was now bunched up around her neck. Her hair looked a mess but she was still a really attractive girl!
“I brought you a cup of tea at mid-night but you were fast asleep,” I replied, trying to dig myself out of the hole that I was certainly in right now. “Anyway, here is your breakfast.”
Ailsa took hold of the tray and placed it on the small table in her cell.
“Are you not going to join me,” she asked?
“Nope,” I replied. “I’ve a lot of work to do on the website today so I think you’ll be safe in here today!”
Ailsa then turned to face me:
“You’re not going to leave me in here all day are you,” she started to panic?
I just smiled as I stood in the open doorway of Ailsa’s cell.
“I’m going to leave the cell door open Ailsa,” I explained. “You’ll therefore have access to the shower and I’ll bring you some clothes to wear but for now, you’re my prisoner and I’m enjoying keeping you under lock and key!”
Ailsa then approached and gave me a kiss. As our tongues met, she pulled back:
“Are you sure you want to leave me in here today,” she teased?
“Yes,” I replied and then as I gone, closing and locking the next set of bars, which meant Ailsa had no route to leave the tiny cell block.
Back at the house, I headed to Ailsa’s bedroom and her massive walk-in closet. I’d no wish for my girl to be in jeans or trousers but she owned very few pairs. Ailsa’s cloths collection was generally made up of skirts, dresses, blouses and sweaters. After some deliberation, I found some uniforms so I thought the black satin French maids outfit would best serve my purpose today. Turning to the drawers for a white bra, pants and a pair of cream opaque tights, I was soon ready to return to Ailsa but only after I picked out a pair of black leather strapped shoes with an enormous heel. These shoes had tiny locks, just like the pair Ailsa had previously forced me to wear so soon I was back in the outhouse, leaving the cloths just the other side of the barred gate, where Ailsa could easily retrieve them. I then headed back to boot my PC and start back into the website but less than an hour into my work and watching endless video of yesterday’s escapades and countless digital pictures, I was extremely honey so I had to check on my prisoner. As I entered the outhouse, I went into the storeroom to pick out a few more toys to add to Ailsa’s Saturday in my custody. A couple of things interested me but my decision turned to three spheres (2 small and 1 large). I knew from my time on the internet that the small spheres would lock around your hand, which would be forced into a fist. The larger sphere would fit over the victims head and leave them bind and locked in a form of iron mask. I lifted these items and headed back to the set of bars and stop Ailsa from exiting the cell block:
“Are you there Ailsa,” I called out?
“I’m in here,” she shouted from the first cell, the same cell she’d spent all night in.
“Can you come out here,” I called back?
“Not possible,” responded Ailsa. “I’m a little tied up right now!”
I guess she’d done what I did yesterday and fancied some time in manacles, attached to the cell wall.
“Are you surprised to see me like this,” asked Ailsa as I entered the tiny cell?
“I guess not,” I replied, popping the three spheres in the bunk.
“You’re not putting those on me are you,” asked Ailsa?
“Yes I am,” I replied. “And you’ve made it even easier for me!”
Ailsa had no option but to allow me to slip each sphere over her wrists, forcing her hands into a fist, now locked securely within the iron balls.
“This looks a bit severe,” I commented, picking up the larger sphere.
I placed it over my head and held it closed, ensuring he lock didn’t engage.
“Go on Dan,” teased Ailsa. “I dare you to close it!”
“Not a chance Ailsa,” I laughed, taking the iron sphere off my head and holding it to hers. “What is the longest you’ve spent in this thing?”
“It is very claustrophobic in that helmet,” responded Ailsa. “I think the most I’ve managed is an hour.”
“Oh well,” I laughed! “It’s eleven o’clock now so I’ll let you out at one to make us both some lunch like a good little maid should.”
“You’re a cruel master,” complained Ailsa as I closed and locked the iron sphere around her head.
I then slipped my hand under the hem of her dress and felt for her most private place, which was getting a little wet.
“I know you’re okay with this,” I continued to laugh before exiting the cell, closing and locking the door.
Back in the house I continued with the website until I had it is reasonable shape. It was then I noticed it was now after two o’clock and Ailsa would be really pissed with me (again). I got up and shot across to the cell where Ailsa was still standing, manacled to the wall with her head and hands still in the iron spheres.
“Is that you Dan,” came Ailsa’s voice from behind the sphere?
“Who else can it be,” sweetheart,” I replied as I unlocked and removed the large iron sphere from Ailsa’s head.
“What time is it,” asked Ailsa?
“I’m s sorry darling,” I replied. “It’s just after two. I was so engrossed in the website that I forgot about you. It’s just about finished so I promise you that I’ll do whatever you want to do this afternoon.”
Ailsa threw hers arms around me and kissed me on the lips as I freed her from the wall-mounted manacles. I then held each wrist and removed the smaller spheres, throwing them onto the bunk:
“You may live to regret offering me that Dan,” responded Ailsa, forcing herself in for another long and passionate kiss.
“Whatever,” I brushed off Ailsa’s comments. “Let’s go over and prepare some lunch and then I can show you the website.”
We walked back to the main house and the kitchen hand in hand. We prepared lunch and then sat together, free form any bondage and ate. I have to admit that Ailsa looked great in her French maids outfit and she knew it was driving me nuts, especially when she rubbed her white Lycra clad leg against mine:
“How about you put away the dishes and I go upstairs and find something more appropriate for you to wear this afternoon Dan,” requested Ailsa who clearly had revenge in mind.
“OK,” I replied. “What do you fancy doing all afternoon?
Ailsa just put her arms around me a whispered:
“Dan darling, I’m going to test my new website to destruction,” explained Ailsa. “I want peace and quiet to do it so you’re spending this afternoon in the cage. If I like the website, you’ll get out for dinner and we can sleep together tonight but if I don’t like it, you’ll be eating dinner through a straw and staying in the cage until tomorrow!”
Now that sounded like a threat if you asked me but I had put Ailsa through a lot since yesterday afternoon so I guess it was her time to have some fun at my expense. As finished packing the dishwasher, Ailsa called me up to the pare room:
“Put these on,” she demanded, throwing me a pair of very unsexy (black) pants and a black bra.
The pants held everything in and the bra held a pair of massive silicon breast forms. Next I was handed a pair of very thick wool tights, not that different to the pair I wore yesterday but this pair were black. Next item to come out of the wardrobe was a massive sweater dress, made from the thick navy-blue wool. As I pulled it over my head, the dress clung to my body and needed to be pulled into place around my ankles. The sleeves were long and required to be rolled back on themselves to avoid covering my hands. The neck of the dress was the same! I had to roll it several times to avoid covering my entire head but Ailsa soon gave me something for that! She handed me the same thick black wool balaclava I wore yesterday and after some tugging, it was fitted under the collar of the dress.
“You’ve never worn boots before Dan so now is a good time to find out what they’re like,” laughed Ailsa as she threw me a pair of high heeled black leather boots.
I then sat on the bed and pulled o each boot.
“I’ll never be able to walk in these,” I complained, standing up and hobbling toward Ailsa who was still in her French maids outfit.
“You’ll not need to walk far Dan, promise,” responded Ailsa as she took me by the hand and led me back across the outhouse.
We first visited the storeroom and Ailsa picked out he heavy prison set I’d worn briefly last weekend. These cuffs and leg-irons were old and very heavy but attached to each other by a long and very heavy chain, my ankles were soon hobbled and my arms held tightly behind my back. As I followed Ailsa towards the cells I struggled to keep up in the high heeled boots and now the chains that restricted my movement even more. Standing outside the cell Ailsa had spent all night and morning in, I was soon being subjected to the hand spheres, which forced each of my hands into as tight fist. Ailsa then picked up the head sphere and I followed her into the cell with the cage:
“On your knees slave,” She called out!
“OK mistress,” I laughed in reply!
Once on my knees Ailsa fitted the heavy iron sphere around my head. It was a very tight fit to begin with but now I had a thick wool balaclava around my head, the iron sphere was even tighter!
“In you go slave,” Ailsa kept up the game as she basically shoved me into the cage, causing me to fall on my face or should I say the iron sphere helmet.
I then heard the cage door being slammed closed:
“Right Dan,” explained Ailsa. “It’s now three-thirty. You left me in those spheres for three hours so I’m leaving you in them for three hours as well. If the website is up to scratch I’ll let you out at six-thirty but if it’s pants, you’ll be let out of the cage for a piss and then locked into a cell for the rest of the night and tomorrow you can fix the website!”
That was all I heard as Ailsa slammed the cell door closed, leaving me to sweat in my wool outfit, locked in the cage.
As you can imagine, I was hot, very hot! The fact I was practically covered head to toe in thick wool was the largest part of my problem right now. The other fact that I was chained hand and foot with heavy iron spheres covering my head and both hands meant this was going to be a very uncomfortable three hours. I guess that I resolved myself to sit down, relax and accept this pay-back because I had deserved it. I had kept Ailsa my prisoner for nearly 24 hours and the last three in a straightjacket so this was penance for my behaviour. Don’t get me wrong, I was enjoying my bondage very much but I hoped Ailsa would love my website enough to let me out in three hours’ time. In saying that, how long had I now spent in here and therefore how long did I have left, covered head to toe in wool, manacled and shackled with the added discomfort of the iron spheres.
I served my time slowly that afternoon and at some point during the early evening (I think) I heard the cell door being unlocked:
“Is that you Ailsa,” I called out?
“Who else would it be Dan,” came that sweet island voice I was falling in love with.
“How do you like the website,” I replied, trying to change the subject and trying to determine my fate this afternoon?
Ailsa didn’t reply as the cage door opened and I could feel her sliding in beside me. I then felt the sphere being unlocked from my head and as soon as the heavy iron had been lifted free I could see Ailsa was still wearing her French Maids outfit. She came straight in and kissed me through the open mouth of the wool balaclava:
“The website is fantastic honey, I love it,” Ailsa finally broke the silence.
“I’m so glad you like it,” I responded, taking a large breathe, relieved that I’d soon be free.
Ailsa then bent over in the small cage to unlock my ankle cuffs before turning me around so that she could reach the handcuffs.
“What about these,” I asked as I held up both hands, referring to the sphere still locked around my wrists?
“I suppose so,” replied Ailsa using the special key to unlock the hand spheres. “Please keep the mask on but or I’ll have to handcuff you again.”
“Okay,” I replied, moving in for another kiss, which was accepted and reciprocated.
When we finally broke up, Ailsa and I gathered the various toys and headed back to the main house after placing them all back in the store. Dinner was fantastic and we sat for hours, drinking wine and enjoying each other’s company while listening to music. I remained in the heavy wool dress all evening but was allowed to remove the thick balaclava just before dinner. An hour or so after diner, Ailsa insisted I put it back on, which to be honest was expected knowing her love of hoods and mask and quite frankly, I was happy to accept based upon my own kinky nature.
We finally fell into bed around eleven and we were due to spend our first full night in bed as lovers. After getting naked and making love until well past mid-night, Ailsa insisted that I joined her wearing a long nightdress and tights to sleep in. I was only now really beginning to understand this girls’ appetite for kinky wear. Never-the-less, I slept well that night and wondered what Sunday would bring.
Sunday and a brand new day!
I was woken sometime after nine by Ailsa falling out of bed:
“What are you doing honey,” I asked?
“Just trying to open my bed-side drawer without getting out of bed,” replied Ailsa.
“Well you did a piss poor job at that,” I laughed in response. “What were trying to get?”
“These,” replied a dissevered Ailsa, climbing back into bed, holding a pair of standard handcuffs.
“What are those for,” I teased?
“To have fun with you,” responded Ailsa, taking hold of my left wrist and closing the cuff around it. ”Now put your arms behind your back!”
“What if I refuse,” I continued teasing?
“Why would you want to refuse a girl like me,” Ailsa started joining in, lower her head and fluttering her eye’s?
How could I resist and I allowed Ailsa to lock my arms behind my back.
“What now,” I asked hopeful for some fun?
“I’m going for a shower,” responded Ailsa, getting up from the bed.
“Hey that’s not fair,” I shouted!
Ailsa started undressing in front of me. First came off her nightshirt, followed by her black tights and then her silk panties. I sort of knew what was coming next as she picked up her pants and tights and approached the bed again:
“Come on honey, open up,” requested Ailsa in a low sexy voice.
I kept my mouth closed; trying to avoid her stuffing the pants she’d worn all day yesterday into my mouth.
“Oh come on Dan, you know you want to,” Ailsa continued teasing taking of and then pinching my nose.
It was no use, I couldn’t hold my breath so as soon as I opened my mouth to take in air, the back silk panties were stuffed into my mouth, followed by the body part of her tights. The legs of her tights were then tightly wrapped around my head and tied of, holding the packing inside my stuffed mouth.
“Enjoy,” laughed Ailsa who now skipped towards the ensuite and a long hot shower.
From the bedside clock, I could see Ailsa has spent forty minutes in the shower, doing whatever she did. Finally she emerged with a towel wrapped around her body and another towel wrapped around her hair. Sitting on the chair at her dressing table, Ailsa spent another half hour drying her hair and applying make-up before retrieving a bright red matching bra and panty set from the dressing table drawers. From the mirror, Ailsa could clearly see me staring at her as she got dressed. I could also clearly see myself staring at Ailsa, a man in a blue nightdress with his arms pinned behind his back and a pair of black Lycra tights gagging him.
“Red for danger today, don’t you think,” Ailsa finally broke the silence, standing up and turning towards me?
All I could do was MUMPTH into my gag and nod in agreement.
“I’m glad you agree with me sweetheart,” replied Ailsa now fishing for something else in another drawer. “I think these will do perfectly,” she continued teasing me, holding up a pair of bright red Lycra tights which she sat on the bed beside me to put on.”
Getting up and doing a twirl in front of me, Ailsa then headed into the massive work-in closet to pick out her Sunday outfit. She emerged only a few minutes later wearing a zebra print, black and white summer dress with a pair of high heeled shoes with a massive leather strap holding them on around her ankles.
“Do you like,” teased Ailsa again, giving me another twirl?
Again, I nodded vigorously and MUMPTHED into my gag.
“Don’t go away,” Ailsa then asked, heading out of the bedroom. “I’ll be back in a few seconds with something for you to wear!”
Where could I go? My hands were cuffed and my mouth packed with her pants and tights! I manoeuvred myself towards the side of the bed where Ailsa picked up the cuffs from a drawer in her bedside cabinet. As luck may have it, the drawer was still open and lying on top of some other interesting toys; I saw a bunch of keys which I knew would unlock my wrists. I had to get them so easing myself off the bed I was soon fiddling around with my arms cuffed behind my back to grab hold of the keys, which were lodged among some silk scarves and a vibrator. Grabbing hold of a scarf (ascendency) and the keys, I climbed back on the bed.
“What are you doing, shouted Ailsa, coming back into the bedroom with a pile of cloths in her arms?
I MUMPTHED into my gag but Ailsa quickly came around, grabbing the contents of my bound hands.
“Right I’ve found you nice outfit to wear today so as soon as you’ve freed yourself, take a shower and get dressed. I’m doing out from some rolls and will be back in thirty minutes,” explained Ailsa.”
She then stood back with the keys and silk scarf in her hand and smiled.
“To make this interesting,” she laughed, approaching with the scarf, “I think I’ll blindfold you!”
With that Ailsa took the large multi-coloured triangle of silk and folded into a thick band before placing it over my eyes and tying it off behind my head.
“Right mister,” she continued. “The keys are on the bed. All you have to do is find them, release your hands, get naked and have a shower. When I come back I want you dressed and please use the scarf to cover your head Grace-Kelly style, I’m sure you can work it out!”
With those instructions, Ailsa was gone and I had the job of finding the keys before I could do anything else: My first thought was to dislodge the scarf blindfolding me but it was tight, very tight! I eased my head towards the frame of Ailsa’s king-size bed and tried my best to push the scarf off my face. It wouldn’t budge! The silk was smooth and obviously very expensive so I therefore had little option but to turn around and feel for the keys with my cuffed hands but that was easier said than done!
I thought I had an idea where Ailsa had dropped the keys but they simply weren’t there. I was breathing heavily by now and this meant the silk panties got even wetter than they already were before Ailsa had stuffed them in my mouth. It was then I understood that that silk is very hard to breathe through when wet! I had to try and breathe through my nose but that was tough because Ailsa had folded the silk scarf into a very wide band that also covered my nose, making my work even harder! I simply couldn’t find the keys but then I brain-eave; had Ailsa left them on the bed-side cabinet when she picked-up the scarf? I had to find out by manoeuvring myself towards the edge of the bed and reversing towards the bedside cabinet, I fumbled with my fingers until finally I found the keys. ‘YEAH’ I thought to myself, grabbing the large bunch and feeling for the key that would unlock my S&W handcuffs. I had a lot of experience at home during self-bondage because I knew that the Yuil key was different from the key that fitted Hiatt or S&W cuffs. Finally I was there and after feeling where the key-holes were I soon had the first cuff free! Pulling the scarf from my face (now lying bundled around my neck), I unlocked the second and therefore, last cuff. All I had to do was plug the tights from my mouth, removing the silk pants from my mouth and then I could get undressed and take a well-earned shower.
Boy was it a nice shower! Soon as I drying myself off and heading out to the bedroom to see what Ailsa had left me to wear today. I knew I’d be cross dressing today but what had Ailsa picked out for me today? Umm, this was different! First all there was the usual black bra and pants. She’d also left me two large silicon breasts to slip between the padded bra and my flat chest. That done I move into a pair of thick Lycra green tights; yes green tights! Ailsa was certainly in a colourful mood today but she did say to me last weekend that she liked more colour on a Sunday. Next came a thin black stretchy bodysuit with a built in bodice and poppers. I pulled this on over my torso and then I pushed home the three poppers over my green covered crotch. Over this, Ailsa had provided a loose grey summer-dress. I easily pulled this over my head and down my now smooth body. I then had to negotiate the shoes Ailsa had left for me. They were black with a heel that was much higher than I would have hoped for and a thick strap to secure the shoes to my ankles, not that different from the shoes Ailsa was wearing today. I was done but as I turned to the pile of cloths I discarded this morning, I remembered the green silk scarf that Ailsa had asked me to wear Grace-Kelly style this morning. Opening out he triangle (yes I’d done this before) I placed the scarf over my head and pulled the end tight until I could wrapped them under my chin, tying them off behind my neck. I was now done! Looking in the mirror I saw a slightly large female staring back with a man’s face. Not the most attractive look to me but never-the-less I expected Ailsa would be happy.
It was then I heard her voice as she entered the bedroom:
“I see you freed yourself,” laughed Ailsa. “I love the outfit!”
“I thought you might,” I laughed in response! “I feel ridiculous but I suppose it is only you and I in this big house so what the hell,” I shrugged my shoulders.
Ailsa approached gave me a kiss:
“I love the fact you’ll dress like this for me,” she praised, kissing my again, forcing her tongue deep into my mouth.
“I’m glad you understand that I’m only doing this for you Ailsa,” I ensured she understand this wasn’t a lifestyle for me beyond this house? If you are happy with the website, I’d like to upload it today and get it live before we head to the mainland tomorrow.”
“How long will that take,” asked Ailsa?
“I just need five minutes to prepare the upload but as soon as I send the file on its’ way, I just need to sit back and check things are fine in a couple of hours,” I explained.
“That’s perfect Dan,” responded Ailsa. “I’ll make us some brunch and you prepare the upload. As soon as we’re finished eating I like you to experience the gibbet.”
Ailsa was right, I’d not had any first-hand experience of the gibbet but I thought there was no way I’d fit in it but of course, I was willing to give it a go! As Ailsa prepared food, I started the process that would take over two hours to upload the new website to the Cloud and make set us on our way to a profitable alternative B&B.
“Right, that the website started,” I opened the conversation as I entered the large kitchen to see my girl where she did her best work!
We ate breakfast and enjoyed each other’s company. It was during these times that I forgot all about the way I was dressed and accepted myself for the situation I was in.
“Right let’s take you over and get you settled into some bondage and then I’ll come back and clear up,” explained Ailsa.
With that she stood up, took me by the hand and led my out of the kitchen, across the courtyard to the out-building that housed the really fun stuff.
“Are you sure I’ll fit in there Ailsa,” I acted sort of concerned where I was about to be locked into?
“We’ll find out in a minute,” replied Ailsa as she opened the gibbet and directed me to stand inside with my back to the wall.
Ailsa then started to close the front portion of the gibbet frame. It was tight but with a little push and a CLICK, I knew the front piece had engaged with the lock and I was going nowhere.
“How long am I to be stuck in here,” I asked?
“Until I let you out sweetie,” responded Ailsa as she exited the room, closing and locking the outer door.
I was going nowhere! My body was tightly squeezed into an iron frame. My arms were pinned to my sides and my head was held tight in the frame that would not be released until Ailsa returned! I was honey in seconds and the fact I was wearing the grey dress over the black thin bodysuit and green tights, the high heeled shoes and the green silk scarf tied Grace-Kelly style around my head, I was bound in an iron gibbet, which was also secured inside a locked cell. I was therefore going nowhere and unable to do anything about my aroused state so I had zero options open to me, except to stand here and accept my situation. Standing, now that was also a chore! My feet were killing me in these high heels! I’ve no idea how girls wear them? They’re bloody awful and I can fully appreciate why men never had to deal with such torture!
By the time the outer cell door opened I was in pain, terrible pain:
“Thank goodness you’re back,” I immediately broke the silence!
“Why did you miss me sweetie,” teased Ailsa as she came up to the gibbet and pushed her fingers through the bars at my crotch area. “I see you are glad to see me though.”
“Ailsa my feet are killing me honey, can you please let me out of this thing,” I pleaded?
“What’s it worth,” Ailsa continued to tease?
“Anything to get out of these fucking shoes,” I started to get a little ratty!
“Now, now Dan,” Ailsa kept up her front. “There is no need to get grumpy with me. All I wanted to know is what you would do for me if I released you from the gibbet and allowed you to take off your shoes.”
“Darling, I’m sorry,” I calmed down. “These shoes are torture and I just want out of them so you name it and I’ll do it.”
Ailsa stood back and held the keys in her right hand:
“Okay Dan, here’s the deal,” Ailsa began to set-out her opening deal. “I will let you out of the gibbet and I’ll allow you to take off the shoes. I’ll even allow you to take off the dress but I want you in a white canvas straightjacket for the rest of the day and locked in the padded cell!”
I just stared back at Ailsa through the iron frame of the gibbet:
“Okay Ailsa but only after you give me half an hour to check the website upload process,” I set-out my side of the negotiations.
“That seems reasonable Dan,” replied Ailsa, placing the large key into the gibbet lock and turning it.
The pressure on my body immediately subsided and I fell out of the gibbet into the open cell and Ailsa’s arms.
“Hey honey, we haven’t used that yet,” I tried my luck, pointing at the Saint Andrew’s cross.
“Neither we have,” responded Ailsa, “Would you like to try it?”
“I was thinking more that I’d like to attach you to it while I check on the website,” I continued chancing my arm!
Ailsa stood back and thought about it for a minute:
“Do you promise to release me as soon as you’ve checked the website,” she tested my motive?
“Of course honey,” I replied, trying to hold back a smile.
“Okay then,” Ailsa handed me the keys and manoeuvred herself towards the Saint Andrew’s cross and the leather buckles.
With Ailsa now with her back to the Mahogany cross, I slowly attached each padded leather strap around both her wrists and tightened them as best I could. Kissing her on the mouth and kneeling down, I did the same with Ailsa’s ankles.
“Are you sure you can’t free yourself from this sweetheart,” I asked, standing up to face my pretty little friend who’s arms and legs were spread to form the shape of the cross she was buckled to?
“There is no way to reach the buckles,” replied Ailsa. “Peter had me attached to this for four hours one day and I fought hard to free myself with no success.”
“That’s perfect,” I replied. “I’ll be back as soon as I’ve checked the website and made us a light lunch, is that okay?”
“Just don’t be long,” Ailsa pleaded as I exited the cell, closing and locking the heavy door behind me.
As soon as I made it back to the house, I had to get rid of these fucking shoes. I went straight to the spare bedroom and sat on the bed. Soon they were gone but I had to replace them with something so a pair of low-heeled slip-on pumps were the perfect solution. The website had finished uploading twenty minutes earlier and after another thirty minutes of testing, I was back in the kitchen making Ailsa and I a light lunch. As soon as it was prepared, I went back to unbuckle Ailsa from the cross and we headed back to the kitchen to eat. This meant for the next hour it was like two girlfriends in dresses having some time together over Sunday lunch.
“So are you ready to be jacketed Dan,” Ailsa suddenly changed the subject?
“That sounds like fun sweetie,” I laughed in response.
Ailsa agreed to put away the remnants of lunch after locking me up for a few hours frustration so we headed over to the outhouse and the storeroom:
“Can I try the white canvas jacket Ailsa,” I asked?
“That’s exactly what I was thinking,” replied Ailsa as she pulled a white canvas jacket off the hanger. “I suggest you take off your dress Dan but leave everything else on, including the head scarf!”
Ailsa then held the jacket open as I pulled the dress over my head and stood in front of her wearing the thin bodysuit, green tights and the green silk headscarf. I must have look hideous as I held out both arms to receive the heavy canvas jacket.
“This feel heavy,” I commented as Ailsa let go of the jacket as soon as my arms held it in place.
“You’ll love this one Dan,” Ailsa responded as she started to buckle the jacket closed from behind.
I could already feel how tight this was going to be! Ailsa pulled the three rear buckles as tight as she could:
“Okay dearest,” Ailsa then gave me the next instruction. “Fold your arms through the chest strap and feed them through to me please?”
That done I felt Ailsa pull very hard on the straps attached to my sleeves, hauling my arms tight against my chest.
“Spread your legs,” demanded Ailsa, slapping me on the backside!
I responded immediately, to find Ailsa grab the crotch strap that hung between my legs and haul that strap tight to buckle it.
“Nearly done,” said Ailsa as came round to face me again!
The last strap was on the front of the high collar of the canvas jacket:
“You can probably guess Dan that this is a bespoke straightjacket,” explained Ailsa. Not all straightjackets come with a leather neck strap but I think it is a great addition to this jacket.”
As soon as the last buckle was done up, good and tight, Ailsa led me through the cell-block to the tight room, or the padded cell!
“You wait in there and I’ll be back in a second,” requested Ailsa as she pushed me inside, slamming closed and therefore locking the padded cell door.
There was little else for me to do except stand there and wait for Ailsa to return, which she did in a matter of minutes, unlocking and opening the door:
“I think this will add to your enjoyment this afternoon,” laughed Ailsa as she entered the padded cell holding another leather strap with two large cuffs attached.
“Do you not mean, add to my frustration this afternoon Ailsa,” I laughed in reply?
“Whatever,” replied Ailsa as she knelt down to buckle the two leather cuffs around both ankles? “Can you please kneel Dan?”
With some help from Ailsa I was soon leaning on the padded floor of the cell. I could then feel Ailsa attaching the leather strap from the ankle cuffs to the back of my jacket:
“What are doing honey,” I asked?
“Just adding to your afternoon of fun, I mean frustration,” replied Ailsa. “Now there is no way for you to stand up!”
Ailsa then popped back out of the cell for a few seconds to pick something else up. I recognised the ball-gag head harness as soon as she returned:
“No honey, that’s not needed,” I started to plead!
“Yeah but it will add to your fun this afternoon,” Ailsa teased in reply as she lifted the hideous looking web of leather towards my face. “Come on open up, you know that you want to!”
“Nah,” was all I got out as Ailsa used the opportunity to shove the massive red rubber ball into my mouth.
With me shaking my head and MUMPTHING as loud as I could, Ailsa pulled the straps into place. Around my head and under my chin before she tightened the buckle hard, forcing the rubber ball deep into my mouth and adding to what was sure not going to be a fun afternoon for me!
“See you later Dan, enjoy your afternoon,” laughed Ailsa as she left the padded cell, closing and locking the door behind her.
It was then the full reality of what bondage I’d just allowed Ailsa to put me into hit home: She was right; I couldn’t stand up because of the leather strap that now bound my ankles to the back of the straightjacket. The attempt to stand up just brought me crashing face first into the soft padding of the tight room floor. I screamed in frustration into my gag but as you can imagine, not a lot of sound escaped my lips. I struggled to sit but that was also impossible so the only option to me was to lay my side, bound with little to no movement until Ailsa returned for me. To be honest, it wasn’t an uncomfortable position and the only discomfort I felt was my aching jaw from the enormous rubber ball that had been forced into my mouth. The silk scarf protected my head from the harness that was buckled very tightly to hold the ball gag in place but apart from that I had little to do but lay there in silence and contemplate why I was here, locked in the padded cell bound so tightly? This of course made me very horney but again there was nothing I could do to relieve that particular itch! Yes the crotch strap was tight against the green Lycra tights and wearing only thin silk panties did mean I could get some pressure against my throbbing dick but no matter how much I tried, the bucking motion only served one purchase and that was to make me even more frustrated. I would stop for a while and then start to release myself from the confines of the canvas jacket. I’d get horney again and try to bring myself to orgasm but when that didn’t work I’d give up and rest until my energy returned and I’d begin the entire cycle again. I was therefore exhausted by the time Ailsa finally returned. She knelt down beside me and unbuckled the straps around my head. With a little effort the massive rubber ball popped out of my mouth, along with hours of saliva build up:
“Thank you sweetheart,” I whispered as the gag finally came off.
“You’re welcome my dear,” replied Ailsa rubbing her hands over my silk scarf covered head. “Would you like a drink of water?”
“Yes please,” I replied.
Ailsa got up and left the padded cell. She was back in less than a minute with a glass of water and a straw. She then helped me onto my knees and placed the straw into my mouth:
“Thanks Ailsa,” that was very nice thank you,” I praised my girlfriend and captor.
“You’re welcome dearest,” Ailsa responded. “So how do you like the canvas jacket?”
“I’ve dreamt about being held in a tight straightjacket for years Ailsa,” I replied. “The leather jacket last weekend was fun but this is just so cool!”
“That’s nice to hear,” Ailsa came straight back at me. “You’ll not mind spending some more time in it!”
“Hey, that’s not fair,” I pleaded for some release from this cruel bondage.
“Who said this game would be fair,” Ailsa laughed in response to my pleading? “You’re clearly enjoying the canvas straightjacket and who am I to stop you having fun? Anyway, it is nearly six so I want to make us both a bite to eat. Can you handle another hour and then I’ll let you out?”
“As long as it is only an hour sweetheart and you don’t gag me again,” I pleaded for at least some freedom from another aching jaw.
Ailsa thought about my request for a minute and then started to kiss me, while at the same time rubbing her hands on my silk covered head:
“You really do like the silk scarf Ailsa,” I began to tease.
“You know I do,” Ailsa responded. “Silk scarves are so versatile,” she continued, now untying and removing the silk scarf that was secured to my head, Grace Kelly style.
Ailsa then smiled at me while she folded the green silk scarf into a thick band. I knew what was coming next and could do little to resist as Ailsa brought the silk up to my face, placing the soft padding across my eyes and tying the scarf tightly behind my head.
“Now isn’t that nice,” Ailsa laughed? “Your challenge for the next hour is to try and dislodge the scarf.
“What do I get if I manage that,” I tried to get one over on Ailsa?
“You’re in no position to negotiate Dan,” responded Ailsa in a semi-serious voice.
“I was just trying to make this game interesting,” I came straight back at her.
“I’ll tell you what,” Ailsa set out her stall: “You dislodge the scarf and I’ll free you from the jacket for dinner and if you don’t, I will free your legs but you remain in the jacket for the rest of this evening.”
“That’s just not fair,” I replied.
“Again I’ll repeat myself Dan,” Ailsa continued the one-sided approach to my current bondage and her fun: “Who said life was fair and if you continue moaning you’ll spend all night in the straightjacket!”
“Okay you win sweetheart,” I gave in.
“I knew you’d see it my way,” responded Ailsa as she got up and exited the padded cell, closing and locking the padded door behind her.
So here I was once again, for the fourth hour secured in the straightjacket and locked in Ailsa’s padded cell. To say I wasn’t enjoying myself would have been a lie but the four hours had been long and I was getting uncomfortable, especially my need to take a leak. I did have a challenge and that was to see again or should I say, dislodge the green silk scarf that blindfolded me. This meant me crashing to the padded floor once again and using my nose, pushing against the padded wall with the objective of at least getting a little movement on the scarf so that it could slide down my face. This was much more difficult than I had expected. The padded walls gave me absolutely no way to ease the scarf out of places by the time Ailsa returned, I still couldn’t see:
“I can see you’ve not managed to dislodge the scarf,” laughed Ailsa!
I looked up in the direction of Ailsa’s voice and smiled:
“Sadly not my dear,” I sarcastically replied.
“Oh dear,” replied Ailsa. “You know what that means!”
I then felt Ailsa working on the leather strap that kept my ankles bent towards my jacketed body. Once that was undone I felt her unbuckle and remove the leather cuffs that bound my ankles together:
“Right onto your feet my boy,” demanded Ailsa as she helped me to finally stand for the first time in hours. “There is no point wasting the nice meal I’ve prepared.”
With my arms still bound so tightly in the straightjacket and my sight still gone from the thick green silk scarf that covered my face, Ailsa led me out of the padded cell. As we exited the nice soft floor and stepped onto the hard concrete, she helped me back into the low healed leather shoes. That complete, I was led blind back to the house and the warmth of the kitchen. It was only then did Ailsa tug the scarf from around my face until it rested around my neck.
“Honey, I badly need to take a leak, can you please at least remove the jacket and allow me to eat in relative freedom?
Ailsa stood in front of me for a minute before agreeing to unbuckle the straightjacket.
“If I let you out of this Dan,” Ailsa set out her demands before starting the process to unbuckle the straightjacket. “You will not complain when I lock you in a cell for the night?”
“Oh honey,” I complained. “I was so looking forward to spending the night with you again.
Ailsa stood facing me:
“Not tonight honey,” I explained. “I love knowing that you’re locked up all safe in your cell at night so the deal is simple: You want out of the jacket now to take a piss then you agree to a night in a cell!”
I had little choice (again) but to accept Ailsa’s demands but at least she was now unbuckling the jacket that had imprisoned me. My piss was therefore even more enjoyable but as I washed my hands, I looked at the image looking back at me in the mirror. As I dried my hands, I played with the green silk scarf that hung from my neck. It looked untidy so I untied the knot behind my head and folded the scarf once more into a triangle. I loved the feeling of the soft silk around my head so I decided that the Grace Kelly style would work again this evening so soon my head (excluding my face) was once more covered in the luxurious layer of soft silk.
“Umm, you look great,” explained Ailsa as I entered the Kitchen to the wonderful smell of home cooking. “I love the way that scarf complements your dress.”
“Yeah, I love it also,” I replied.”
We then sat down to dinner and talked for the next few hours:
“So what time would you like to leave for the mainland tomorrow,” I asked as we started to pack the dishwasher?
“You’re the pilot honey,” responded Ailsa. “It is your decision!”
“Okay, I’ll check the weather when I get up and then we can make a decision,” I replied.
“Don’t you mean, you can check the weather when I free you from your jail cell,” Ailsa responed sarcastically?
“I guess so,” I laughed!
“Anyway, it is getting late now Dan,” explained Ailsa as we put the finally remnants of dinner away. “I’d like to take a bath and get an early night so it’s jail for you.”
“Do you have to lock me up this early sweetheart,” I replied? “It’s only nine o’clock!”
“I’m afraid so Dan,” Ailsa came straight back at me, taking hold of me and planting a kissing on my lips.
We kissed a little bit longer until Ailsa broke for air:
“Would you like to spend tonight in one of my special sleeping bags,” asked Ailsa?
“Do I have a choice,” I replied? “Anyway, what is so special about your sleeping bag?”
“Follow me,” demanded Ailsa, grabbing me by the hand and leading me towards the back door. “Pick up the straightjacket and we’ll put it back in the store!”
We headed back outside and across the yard to Ailsa’s outhouse of fun. Once there we placed the straightjacket back onto its’ hanger and Ailsa pulled a leather sleep-sack from a drawer:
“This is it,” explained Ailsa: “Once you’re in this sleeping bag, you’re in it for the night!”
Ailsa then unzipped the leather sleep-sack and showed me the built in sleeves and the built in mask with only a small hole around the lower face so that I could breathe easily. It was clear once I was zipped into this thing I wouldn’t be able to move my arms of see!
“How do I take a piss,” I asked?
“I put you into an adult nappy (diaper to you Americans),” responded Ailsa, lifting a large plastic nappy from an adjacent drawer. “I do however recommend you go to the toilet before bedtime though!”
I just looked at Ailsa who I thought was going mad:
“Are you crazy Ailsa,” I stood in utter dismay at her suggestion?
It was clear Ailsa had made up her mind so I followed her to the first cell. She suggested that I go to the toilet and undress before pulling on the plastic nappy:
“You might also feel more comfortable pulling your tights back on over the nappy,” suggested Ailsa as she slipped out of the cell, slamming the heavy door behind herm locking me inside!
I couldn’t believe what I was letting myself in for tonight but I followed Ailsa’a instructions and after taking my last leak of the night, I pulled on the horrible padded plastic nappy, followed the green Lycra tights I’d worn all day. Ailsa was back in less than ten minutes with a silk nightdress:
“Umm, nice look,” Ailsa teased as she unlocked and opened my cell door, handing me a green silk night dress to match my tights.
I slipped into the nightdress as Ailsa prepared the sleep-sack.
“The zip runs along the back of this sleep-sack Dan,” explained Ailsa on how I should negotiate getting into the long leather sleeping bag. “If you sit on the bed and ease your feet in first, I’ll help you with your arms!”
Ailsa did her best to direct me into the tight bag. It was made of the finest soft black leather and was padded inside. My arms had to slide into the built in sleeves before Ailsa had to take over the exercise, pulling the rest of the sleeping bag up my body.
“Good night sweetheart,” Ailsa finally kissed me on the lips before pulling the padded hood over my face.
“Good night you too,” I replied as Ailsa started pulling on the zip until it rested on top of my head and therefore the built in hood.
Now that I was safely inside my sleep-sack for the night, Ailsa helped me onto my back before biding me goodnight again and then leaving the cell, locking the door behind her. I therefore remained stuck inside the leather sleep-sack for the rest of the night with means of escape no matter how much I tried!
I lay for ages on that Sunday evening. As you would expect, I remained horney but with my arms stuck by my side in the tight leather sleep-sack there was absolutely no release for me during that long and very hot night. I lay there, trying to relax, hoping that sleep would finally take over and my night in this tight bondage would end much faster. As I relaxed in what was going to be hellish night, sleep did finally arrive!
Monday morning and going nowhere!
When I finally awoke on Monday morning, I’d no way of telling what time it actually was! My world was in complete darkness and I was hot. Both were insignificant to the pain in my bladder, telling me that I urgently needed to take a piss. Despite wearing the nappy under the thick green Lycra tights, I couldn’t bring myself to pissing in my pants! There was also no sound from outside my cell so I drifted in and out of sleep until finally I heard Ailsa unlocking and entering my cell.
“Good morning sleepy-head,” announced Ailsa as she turned me onto my side and pulled down the zip, allowing the hood to be pulled from my face.
“Good morning gorgeous,” I replied staring at the black faceless figure that stood over me.
This morning Ailsa was covered from head to toe in a black leather catsuit. It covered her entire body, including her face with only a mouth and two eyes showing, highlighted by the red leather trim that encircled both openings in the black leather catsuit.
“Do you like,” Asked Ailsa?
“Yes,” I replied! “I will not be flying you back to the mainland wearing it though!”
“We’ll not be flying anywhere my dear,” responded Ailsa. “It is very foggy outside so we’re going nowhere! I have brought you some breakfast so try and sit up so that I can feed you?”
“You mean, you are not releasing me from the leather prison,” I started to get a little worried?
Ailsa picked up the bowl of cereal and returned to my bed, sitting down beside me:
“You don’t need to be released,” Ailsa explained her devious plan for today. “I fancy a little self-bondage in the other cell today so you’ll be very comfortable in here today.”
“You can’t do that to me,” I replied in a slight panic as Ailsa fed me breakfast! “I’ve been Horney for hours and I need to take a piss very badly!”
“Aww, poor little Danny needs to take a pee-pee,” tease a leather clad Ailsa. “You have a nappy so just use it!”
“That’s not fair Ailsa,” I complained (raising my voice!
Ailsa just stood up and headed for the table at the end of my jail cell bed. I could see that she’d just picked up the long green silk scarf I’d worn yesterday.
“You can be a bastard sometimes Dan,” yelled Ailsa as she folded the green triangle into a tight band, before tying a knot in the middle. Ailsa then took hold of my head and forced the silk knot into my mouth and tied the ends of the scarf behind my head. “I like having you as my little bound up slave so unless your attitude changes, you might be locked in for a very long time!”
All I could do was MUMPTH into my gag as Ailsa pulled the built in hood over my head and zipped the sleep sack shut. The last thing I heard was the cell door closing, locking me inside once again, with absolutely no idea when I’d next be released from either the jail cell or leather sleep sack. I lay there for hours, desperate to take a piss so at some point hours after being incarcerated, I finally gave in, peeing in my nappy that I’d worn since before nine last night. I prayed that Ailsa would return but she didn’t. I guess she’d planned a long day of self-bondage so I lay trapped in the leather sleep-sack with nothing to do, unable to see or speak!
To be continued….
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Author: Ed Kilpatrick
E-mail: EdKBound@GMail.com
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