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Click hereTHURSDAY
I promptly knocked at 9 o'clock: May opened the door dressed in a short skirt and cotton t-shirt, ushering me in with a nod of her head.
'Sleep well?' she asked, as I stepped in to the hallway.
'Er, no ... Ma'am' I responded.
'Oh dear, Paul, that's a shame' she said. 'Go through to the living room, I've just made coffee ...'
There were half a dozen shoe boxes of varying sizes stacked on the coffee table when I walked in to the front room, as well as another cardboard box, and a cellophane pack. May walked in with the coffee tray as before, and set it down next to the shoe boxes.
'I'm looking forward to today' she said. 'I do so hope you are too ...'
'Yes Ma'am' was my reply, wondering what she had in store for me after the events of yesterday, but desperately hoping she would release me from the tortuous steel cage.
'Well ...' she went on, 'let's have an inspect then ...'
I stood and stripped naked, save for the steel device evilly secured between my thighs. She walked over and slid her forefinger over the open slit of the cage, a trail of fluid stringing from the tip as she withdrew it.
'My my, that's very wet ... you must be excited! And by the looks of you, still very swollen!!'
She ran her hand beneath and cupped my balls, giving them a gentle squeeze. A tendril of precum oozed from the opening of the cage, dangling there, twinkling in the light as if to prove her point.
'And your balls feel very full again ...' she remarked, licking her lips.
The memory of me exploding in her mouth yesterday made my cock twitch and strain further beneath its steel housing.
'But don't worry Paul, I'm not going to put you through that ordeal again today ... we have some other interesting distractions instead' she said, nodding towards the coffee table.
'Here, put these on ...'.
She leant over the coffee table, exposing her upper thighs beneath her short skirt, and picked up the cellophane packet, which she handed to me. The sight of her shapely legs had notched up the discomfort I was feeling from the cage ... I had little doubt her actions were a deliberate and calculated provocation.
I could see the packet contained tan stockings or tights, and as I removed them, it was clear they were tights, suspender tights, the type that don't have any crotch. I sat back on the sofa, wondering where this might be going, and carefully eased one foot into the toe, pulling the flimsy material over my calf and up to my knee before repeating the same with the other leg: the nylon material felt especially sensuous against my smooth hairless legs.
Standing up, I pulled the tights up my thighs and brought the waist band above my hips, smoothing the material as I went. My crotch area and buttocks remained exposed, and I felt a frisson of excitement which was clearly evident as another thick tendril of precum oozed from the cage.
'Are we getting a little excited?' May asked, noticing my evident reaction, and slipping her hand beneath the descending globule, catching it in her palm before it reached the rug.
'Clearly you enjoy feminine underwear, given I have numerous recordings, but I'm surprised at your reaction over a simple pair of tights!'
'Err ... yes, Ma'am' I replied, feeling my cock staining excruciatingly hard against the confines of the unforgiving steel.
'Well then' she continued, licking the moisture off the palm of her hand, 'we'd better move on before you have any more accidents! I want you to try these on' she said, reaching for a shoe box.
'They are a pair of kitten heel sandals, and I want you to try them on for size, as I'm hoping they'll be a perfect fit'.
She opened the box and passed me a pair of white strappy open-toed sandals. I could see they had been well worn as the soles were scuffed, and there were buckle marks around the ankle straps.
'Are these yours?' I asked May.
'Yes, but I'm more interested as to the fit than the provenance' she replied tersely.
I sat back down and inserted one foot into the sandal, loosening one of the buckles across the foot. My foot slid in almost perfectly, and I tightened the buckles, including the two around the ankle, before repeating the process with the other foot.
'Stand up' she said, 'let's have you walking up and down so I can see.'
I stood up delicately, feeling my balance shifting slightly towards the balls of my feet, getting used to the heel. The kitten sandals felt comfortable, and I took several paces forwards before turning back and repeating my strides across the room while she looked on. I have to say, they were fairly easy to walk and balance in, and they made my legs look quite sexy.
'Come out to the hallway' May said, 'there's a full-length mirror there. See what you think ...'
I followed her out the room, and stood in front of the mirror. My chastity cage twitched once again as I caught sight of my legs, looking slim in the tan tights, accentuated by the strappy heels. Another tendril escaped from the end of the steel enclosure, which this time I rescued with my fingers. The ensemble of crotchless tights, white sandals and steel cage looked superbly sexy in the mirrored reflection, and I never realised my legs were so long and shapely, no doubt down to what I was wearing.
'Excellent' I heard May say, 'I guess you'll want to be trying out another pair!'
I followed her back in to the sitting room, as she reached for a second box. 'These have a higher heel, so let's see how you manage.'
She extracted a pair of black court shoes with stiletto heels, probably three or four inches in height. Again they had been well worn. I unbuckled the sandals and slipped my feet into the court shoes: again the fit was close to perfect. I stood, and felt myself wobble as my feet strained to accommodate the pitch of the higher heels. I remained motionless for some thirty seconds or so, letting my feet adjust themselves, and then took a couple of tentative steps in one direction, before returning back again, all the while trying to get a feel for my balance.
'Not bad, not bad ...' I heard May say. 'They look good on you, go and take a look in the mirror.'
I carefully stepped out in to the hallway, and let out a slight gasp of appreciation: the heels looked terrific on me, superbly sexy, and were it not for the steel chastity device above the apex of my thighs, I could have easily passed for a woman waist down. I returned to the sitting room, getting the hang of the heels, balancing and walking more gracefully than at the outset.
'Excellent' May said. 'I'm pleased you are adapting so well ... but we've a lot further to go!'
'What do you mean Ma'am?' I replied.
She nodded to the remaining shoe boxes on the coffee table, and said 'feel free to have a look.'
I walked over in my heels, and lifted the lid off the next box. It contained a pair of black high heeled lace-up shoes, very matronly, were it not for the stiletto heels, somewhat higher than the ones on the court shoes I was currently wearing. The next box, which was larger, contained a pair of black patent leather ankle boots, with lacing to the front and a zip closure down the inner side. What surprised me with these was the wide leather strap that went around the top of each boot, covering the knotted laces and the zip pull: they were fitted with double padlocks.
'Wow' I said to May, feeling my cock twitch within its tight cage, 'these are sexy!'
'Glad you approve Paul, but I don't think you are ready for these yet, other than to try the fit' May replied.
The penultimate box contained a similar pair of boots, except these had outrageously high heels, with no curvature in the toe: the toes pointed practically straight down.
'Those are called ballet heels' May said, interrupting my thoughts. 'Totally impractical, and probably months away before you have the slightest chance of wearing them ... but they look fun.'
I looked bewildered.
'Those videos I have of you?' she reminded me, 'you know, the ones where you like dressing up? I'd have thought you would have been pleased to progress your little fantasy ...'
I nodded, shamefaced, and returned the boots to their box, and backed away from the coffee table ... I'd seen enough.
'So there's one last thing we have to do before you can return home ... sit yourself on the sofa, and I'll enlighten you' May said, getting up and heading for the coffee table I'd just been at.
She took the smaller cardboard box, and extracted what looked like leather straps and buckles.
Kneeling down she added 'now watch carefully, as you will have to do this at home.'
She separated one set of straps, which resembled a T-shape, and wrapped the widest band around my ankle, bringing the thinner stem beneath the sole and between the heel, linking it to the ankle strap. The three loose ends were tightened, buckled together and secured using a clasp and padlock.
She repeated the process on the other foot before exclaiming 'there, what do you think? Do they keep the shoes in place?'
I could see the shoes were firmly secured to my ankles, and I wouldn't be able to slip off any time soon. I stood up, walked a few paces without issue, and said 'yes, they do the job Ma'am.'
'Good, good ...' she said, 'I'll unlock them now, and you can take them home with the shoes and tights. Once home, I want you to put them back on exactly as I did just now, and email me back with a photo. I'll have the keys with me for safe keeping ...'
'But ...' I began to protest, 'how am I supposed to get the shoes off again?'
'I'm here this evening, so you can call round and I'll unlock the straps ... but in the meantime, I want you to practice walking in heels: you need to get used to them.'
I was a little taken aback, but at the same time excited at the thought of wearing her heels, as they certainly made me feel sexy.
'Umm, yes ... Ma'am' I eventually replied.
She knelt down again, unlocked padlocks, and withdrew, key in hand.
'Well, I think we're all done for the day, you can get changed, and take those items with you.'
I unhitched the leather straps, removed the shoes, eased the tights off, noticing I was still leaking copiously, and put everything back. May was watching me from her armchair, and I quickly pulled my clothes on, before picking up the shoe box, with the strap box and cellophane packet containing the tights.
'May I go now Ma'am?' I enquired.
'Yes Paul, but don't forget, I'll be waiting for photo evidence, and I don't like being kept waiting ... off you go!' she responded.
I took May's items home, eager at the thought of wearing her possessions, although slightly apprehensive at the same time.
My cock ached and throbbed interminably as I immediately changed my footwear once I'd got through my own front door, ensuring that the locking leather shoe straps were pulled tight before securing them with the padlock. I took a couple of photos, and emailed them over to May so she'd know I had followed her orders, and then set about catching up with my work, my penis constantly and painfully gripped hard within its steel confines.
The day went amazing well: May's shoes were reasonably comfortable, and I took every opportunity getting used to the pitch of my feet by walking around the house whenever possible, although I found walking downstairs in high heels not as easy as I had expected. The thrill of the gossamer against my shaven legs, and the clip-clop of my heels, certainly maintained my hardness throughout the day, and I was continually having to wipe away my leakages from the end of the chastity cage.
By the time I wrapped up working, my feet and calves had begun to ache, and I was ready to kick my shoes off and put my feet up, although hard as I tried, the shoes couldn't be removed, as least not without the keys to unlock the leather retaining straps. So I made do with putting my feet up in front of the TV waiting for the sun to set, and darkness to fall.
Eventually the street was shrouded in darkness, and I hesitantly let myself out of the house, gingerly walking down the driveway and peering up the road to ensure the coast was clear. It was, and so I clipped my way down the pavement, furtively glancing to either side to make sure I was not being observed by some curtain twitcher, and rang May's doorbell. No answer. I knocked on the door loudly, and again rang the doorbell. It was some moments later when the light came on in the hallway, and I saw a shadow descend the stairs and approach the door, while in the meantime I kept glancing over my shoulder in case a passer-by saw me.
'Come in, come in' May said, as she opened the door.
I clipped in to her hallway, glancing at her as she stood to once side: my cock immediately twitched and throbbed painfully when I saw she was dressed ready for bed, a diaphanous long white negligee loosely covering a cropped thin cotton top and white lacy minuscule panties, which barely covered her vulva. Her nipples and areole were distinctly visible, as were the nipple rings she was wearing. My cock twitched again, and I let out a subdued groan of appreciation and anguish ...
'Are you okay Paul' May asked, as she waved me into the front room, closing the front door behind her.
'I'll just be glad to get these heels off' I replied, not daring to admit that she was the cause of my reaction: that, and the pain of my bulging cock gripped so tightly by her infernal steel chastity cage.
'Well, you've worn them for a while now, but they do look good on you! Slip your clothes off, and we can get you out of those shoes ...'.
She turned away as I started to pull my t-shirt over my head, and I saw with clarity her divinely shaped buttocks beneath the chiffon negligee, separated by the thin white wisp of lace disappearing out of sight between her firm cheeks. My shorts followed my t-shirt, a thick tendril of leakage stretching below the cage as I stepped out of them.
'My my, you are still very much in a state of excitement, aren't you' she said, as she approached me, a small key clasped between her finger tips.
She knelt before me, using the forefinger of her other hand to interrupt the falling trail of pre-cum, twirling it around her finger before rubbing the tip over the opening of the cage. I gasped loudly and shuddered as I felt it glide over the bulging slit of my cock, which was pressing exceptionally hard against the opening, blossoming outwards slightly. Her glistening forefinger, covered in my clear ooze, then slipped between her open lips, and she sucked on it, smiling at my reaction.
'So so wet, aren't you?' she said, continuing with 'we'll have to find a solution to that, otherwise all my nylons and carpets will end up stained.'
Bending over, she inserted the key into one padlock followed by the other, and removed both retaining straps.
'They you go' she went on, 'you can take those shoes and tights off now.'
I unfastened the leather straps, removed her shoes, and eased the suspender tights down my hips, taking care not to snag them as I took them off. I sighed as the pressure came off my feet, and wished for a moment the same would happen with my cock, hoping she might have another key with which to release me there.
'So' May said, 'I guess I'll see you the usual time in the morning ...'
'Er ... yes Ma'am' I responded, my hopes trashed in a single sentence. I pulled my shorts and t-shirt back in to place, and suddenly realised I had nothing to walk home in: I'd omitted to bring my trainers with me. 'Umm ...' I hesitated.
'What is is Paul?'
'I've nothing to wear on my feet' I confessed.
'Well, you can always wear my heels home' she ventured, smiling.
'Nah, it's okay, I'll go barefoot' I returned, 'but thanks for the offer. My feet have had enough for the day ...'
'I don't think it's just your feet that have had enough' May rejoined, nodding towards her steel cage. 'But then again, we can't have you wanking yourself silly now, can we Paul?'
I shook my head, crestfallen, and added 'how long before I am released, Ma'am?'
'Hmmm, that all depends ...' she said, and dismissed me with 'now off you go, I'll see you tomorrow.'
Disappointed, I withdrew from the room with a subdued 'yes Ma'am', and let myself out, pattering around to my house, treading warily over the pavement and down my driveway.
Thankful to be within the seclusion of my own home, I prepared myself for the night, feeling the ache in my calves having spent so much time in May's high heeled court shoes. I wasn't sure I would be able to progress to a longer heel, at least not for a while.
I had another uncomfortable night, waking up several times, my cock straining for release within its steel enclosure, my balls swollen hugely between my thighs.
The next morning dawned early, and as before, there was no respite for my swollen organ or, for that matter, me! And although the ache in my calves had abated a little, I was still very much conscious that my legs muscles had worked hard in the heels I'd worn yesterday.
I'm wondering if Paul owned a sizeable Dildo? That's probably the only aid he'll be able to use to get any sort of prostate release while locked in Chastity. Bouncing on it till "P" orgasm the next time in the shower.
Nice story. Although i dislike blackmail, I like the way this was only used to get the 2 people together. Paul isn't really forced to do things - actually he is, but the story doesn't feel that way.
I can't wait what the weekend will bring. I hope the relationship will intensify :-)