Another sleepless night awaited me, my sexual frustration building relentlessly. I needed release, but would Emma grant it?

Other than her delivering a large bag of her lingerie for me to wash, I heard nothing from her for a couple of days. Usually the highlight of my week, handwashing her undies proved to be poor torture, caged as I was. Common sense told me not to sniff, but I couldn't resist, which obviously exacerbated my suffering.

I completed and returned her laundry, folding everything as neatly as possible in the hope of her seeing that I was doing my utmost to serve her. But still another day passed with no contact, and then, the next morning, her front door was slammed shut with an almighty bang.

I instantly picked up on the cue and shot out to see her strolling down her driveway, skateboard under her arm. As always, she was scruffily dressed, but I knew that she had to be wearing the most exquisite lingerie.

“Hello, Emma!” I shouted.

She turned around and walked back to me, her face bearing her trademark inscrutable smile.

“What?” she replied.

“Er...” I wasn't sure what to say.

“I'm busy. What do you want?”

“I... I was just wondering if you... like the last time... you know? If you would be so kind as to... you know?”

“What the fuck are you talking about?”

Beating around the bush was getting me nowhere. I had to be direct! “I need to be unlocked, Emma,” I blurted out. “Please!”

“Have you locked your whatsit up again?”

“Er... yes... I did!”

“You were crazy to do that! Nothing can cure stupidity. See you!”

I was left standing there, watching her swagger off. All I could hope was that she would take pity on me and message me later that day. But what price would she extract for a few hours of freedom?

oooOOooo

Another two days passed with nothing from Emma. Despite my advanced years (actually I'm only sixty!), I was used to relieving my frustration on an almost daily basis and it was now about six days since I'd last been able to masturbate. And naturally thinking all the time of Emma did nothing to help my pent-up state.

Then, mid-morning, a message came from “Anon”: “You will edge... you will not cum...”

The instant I read that, my penis pounded against the side of its cage. She was going to release me!

Barely seconds later a further message arrived: “Remember... obedience is rewarded... disobedience is punished...”

Then another: “Back bedroom window... wear panties only... bring frozen peas... NOW!”

Not wasting a second, I raided the freezer, then raced upstairs clutching the frozen veg and my phone. Hastily, I stripped off until I was wearing nothing but a pair of pale blue panties bearing the image of Yogi Bear. I opened “Keyholder” and pressed “unlock”.

I positioned myself by the window and saw she was sunbathing by her pool. She was lying on her back, phone in hand, and with that familiar but imperceptible smile on her face.

I waited nervously for the expected click. She was intent on keeping me waiting, which served to increase the tension I felt.

Then I heard it! My cage had sprung open. I reached inside the panties and, with a little difficulty, removed the cage. Immediately, my penis sprang to attention, just as another email came in: “Stroke... Do not cum...”

Gently, I stroked my erection, fearful that if I pressed too hard, or in the wrong place, I would suffer an eruption. As I did so, I stared down at her. As usual, she didn't return my gaze, but she placed her free hand inside her bikini bottoms, fondling her pussy.

She was driving me crazy and, undoubtedly, she knew it.

Maintaining a hard-on was simple—avoiding going too far was not, made more difficult when she started wriggling in response to playing with herself. Her nipples were now pressing against the skimpy fabric of her top.

I lost track of time when I saw her withdraw her hand and type something into her phone: “Entertainment over... frozen peas... relock...”

The message was blunt but clear. For me, it was another of those watershed moments. Did I call it a day, and refuse to lock myself back up, or did I comply with her demands?

Despite craving to ejaculate, my decision was an easy one. By now I was so under her influence that I knew locking myself up was my only option. Still in full view of her, so she could witness my blind obedience, I picked up the frozen peas and pushed them down inside my panties. I winced as the icy coldness shriveled up my tool. Seconds later, I pulled down the panties and relocked myself into the cage, having no idea when she would grant me release of seminal fluid.

She looked again at her phone, a mysterious smile still on her face.

Then my phone pinged: “Good sissy...”

She had humiliated me, yet I felt a bizarre sense of pride at her compliment.

oooOOooo

Two more days passed without me hearing from her and I was desperate to release my ever-increasing load. I was crawling up the wall in frustration, and I was unable to concentrate on anything—other than think of Emma, of course, which did nothing to help my problem.

I was listening out for her front door slamming but heard nothing until that afternoon. When it came, it was so loud that my house seemed to shake.

Rushing to my door, I yelled, “Afternoon, Emma!”

She was dressed as she always was, but it was what was underneath her scruffy outfit that appealed to me. It was so easy to mentally undress her.

“What?!” she said, turning to glare at me, her inscrutable smile replaced by a look of irritation. “I'm busy!” she hissed, and she held up her skateboard, as if that was evidence of a frantic lifestyle.

“Er... yes... sorry! I won't keep you a minute.”

I looked at her inquisitively, unsure what to say but knowing that she completely understood my dilemma. “Hmm... I'm still locked up... You understand, don't you, Emma?”

“No! No idea what you're talking about!”

“I need relief, Emma. There's a build-up of... erm... you know what.”

She snarled at me with a look of disgust. “You've lost me! You're weird!”

“I've been obedient, Emma! I've been good.”

“Haha!” she snorted, disdainfully. “Tell that to Santa, not me. See you around, loser.”

With that, she was gone.

As I had fully expected, she had played dumb, pretending not to understand what I was referring to. However, I clung to a glimmer of hope. Based on similar chats in the past, it was quite feasible she would soon be in contact with a reward.

oooOOooo

I went back into my house, and spent a couple of hours pacing around, praying that she would message me.

Sure enough, later that afternoon an email came through from “Anon”: “Buy this... it will relieve your build-up... LOL!!!”

I looked in the body of the email. There was a link to a prostate massaging wand! She expected me to purchase that and then to empty my prostate by shoving it up my bum while locked in my cage.

I knew what this would do... it would milk me. It would drain me of seminal fluid, but without the satisfaction of an erection or an orgasm.

This was so degrading. How could I sink so low?

Nonetheless, I clicked on “Buy Now”...

oooOOooo

The wand was delivered the next day. I unpacked the box and looked at the formidable device. Certainly, I was eager to rid myself of my build-up, but this was not what I wanted. I'd read about milking, and I would get release but little sexual satisfaction. Did I really want the humiliation of shoving this up my arse?

Emma must have seen the delivery being made, and, as was her way, she was soon in touch to pile on the pressure to force me into a decision.

“Anon”: “You have one hour to drain yourself... Put plate of spunk on fence post... Do not disobey...”

Not only was she giving me a deadline, but she wanted to see the product of my prostate massaging.

I quickly read the instructions, inserted batteries into the device, and then stripped off. Getting down on all fours, with a small plate beneath my penis, I applied some of the supplied lubricant to the end of the wand and attempted to reach behind to insert it into my rectum.

It was difficult. You need to relax, I told myself, but that was easier said than done. Meanwhile, at the thought of humiliating myself in this way under her direct orders, my penis was struggling in its small prison.

I took a deep breath, then exhaled, and persuaded myself to relax. Success! I felt the thin wand penetrating a part of my body that, up to now, had only known one way traffic—in the opposite direction.

It was a very strange sensation... yet not unpleasant. Groping, I pushed it in a little further and pressed the switch to start it working. Instantly, I felt my prostate being stimulated, and I was surprised how enjoyable I was finding the sensation.

I looked down between my legs to see if any seminal fluid was leaking out. It took a few minutes, but then the first drops appeared, drooling down in long threads and settling on the plate.

I kept going, loving the vibrations but trying to ignore the throbbing inside my cage. I gazed in awe at the slow emissions, and it was probably fifteen minutes before they ceased.

I was now empty, but still highly frustrated. Being denied a proper erection and any stimulation of my penis had meant that this had been no more than a clinical procedure. It had successfully drained me, but I was left unfulfilled.

Time was moving on, so I withdrew the massager, got dressed and took the plate, now containing a sizeable amount of my jism, outside and placed it carefully on a fence post.

Retiring back inside, I waited for Emma to contact me. The message came half-an-hour later. It was short and sweet.

“Anon”: “Good sissy...”

Once again, she had debased me.

oooOOooo

Another week passed by. There was the expected bag of laundry and a couple of “I would look nice in these” messages, but no other contact from Emma. Once I saw her leave her house, with her skateboard, but there had been no slamming of the door. Desperate to talk to her, I'd rushed out and called her name, but she had carried on walking.

My frustration continued to build. I needed to talk to her, to make her see that I wanted to be unlocked so I could enjoy an erection.

Then, eight days after my milking, she left her house, banging her front door firmly shut. This had to be the signal I was waiting for.

“Hello, Emma,” I shouted, as I leant out of my front door.

She swiveled around and I was relieved to see that her face bore her delightful enigmatic smile. That had to be a good omen.

“What do you want?” she asked, as if she couldn't guess. “I'm busy.”

“Yes... sorry... I can see you're very busy,” I replied, disguising my sarcasm. “This... er... cage I'm stuck in... It really needs to come off, Emma.”

“What the hell are you talking about?”

“My chastity cage!”

“Not that again! For heaven's sake? Stop locking yourself up, you idiot!”

“I can't unlock it.”

“Try a locksmith. Or the Emergency Room. Not my problem.”

“I... I know it's not your problem, Emma, but I just needed to tell someone. I'm getting sore and it needs to come off for a while. For just a short time, you understand?”

“No, why would I understand? Why tell me?”

“I have to speak to someone and you're my neighbor... and my friend.”

“Friend? We hardly know each other! And you're old enough to be my granddad!”

“Yes... I suppose I am. I'm sorry to have bothered you. It's my problem, not yours.”

Feeling humiliated, I watched as she strolled off. Sure, we had skirted around the issues, and she had pretended to be ignorant of her role, yet, based on experience, I thought there was a reasonable chance of her reacting favorably within a day or so. And so it turned out to be.

oooOOooo

Later the same day, she messaged me from her “Anon” account: “10 PM... Outside bedroom... Bring phone... panties only...”

Reading her message, my penis started thudding against the constraints of its prison. I couldn't wait for the hours to pass, wondering what she was laying on for me.

Just before ten o'clock, I was standing outside her bedroom window. The drapes were drawn, as I'd anticipated. Quickly, I removed my outer clothing leaving me in just my lilac cotton panties bearing the image of Snoopy.

In the hope that she was going to free me from my cage, I pressed “Unlock” in the app and waited, growing increasingly nervous. My phone pinged.

“Anon”: “Cum into panties...” This was the confirmation I was hoping for... she was going to unlock me and allow me to ejaculate, albeit in a degrading manner.

Then, precisely on the hour, two things happened. A click told me that my cage had sprung open while, at the same time, the drapes began to part. Wasting not a moment, I plunged my hand into my panties and yanked the cage off, my penis instantly springing to attention like a soldier in front of its commanding officer, Major Emma.

The drapes were now fully opened, and the bedroom lights were on. Emma was sitting facing the window wearing the most gorgeous white lingerie—a delicate white bra, a matching pair of panties, a suspender belt in the same style, and a pair of white stockings.

Her face bore her usual inscrutable smile, and her eyes were looking into the middle distance. Seemingly, she was in a world of her own.

As I watched, she gracefully gripped the sides of her panties and slid them down her legs, kicking them off, halfway across the room. Then, unprecedented, I was privileged to see her beautiful pussy, just feet in front of me. It was already glistening from her juices.

Her right hand began fingering herself, and I found I was doing the same. She was taunting me in the most evocative way imaginable. Then her left hand crept inside her bra and began to caress a nipple, which was already standing erect.

I was desperate to come, but I wanted my orgasm to coincide with hers, so I backed off a little. She continued working her pussy, fondling her labia and clit, and sometimes inserting a couple of fingers into her vagina.

It wasn't long before she was writhing and squirming, while mouthing words that were inaudible to me. Sensing that she was not far off, I began manipulating my erection again, bringing it closer to the point of no return. As she wanted, I angled it slightly off the vertical so that my panties would catch the full load. I knew that post-climax I would feel shame but, at that moment, all I felt was exhilaration.

I watched, open-mouthed, as she edged closer and then—bang—her back arched violently and she screamed out, so loudly that I heard through the double-glazing. Seconds later, I also came, my knees buckling as my orgasm overcame my body. I gripped the windowsill for support.

Spurt after spurt filled my panties. I thought it was never going to end, and, similarly, Emma's climax seemed to go on forever. Finally, it was over, for us both. She reached for the remote control, and the drapes began to close.

Longingly, I stared through the diminishing gap until all was obscured.

Then I came down to earth, conscious once more of how she had disgraced me. I was standing with cum-filled panties, staring at her window, but with nothing to see.

Coming to my senses, I picked up the chastity device. Pulling my panties down, I used my sweatpants to wipe my now flaccid member and then I relocked myself into the cage.

She had trained me so well that, for the first time, I had no second thoughts about the wisdom of locking myself up. I had learnt that she was not cruel, and she had no intention of locking me up permanently.

I got dressed and soggily made my way back home. As I entered my front door, so a message arrived from “Anon”: “Sleep in cum-filled panties... sweet dreams...”

oooOOooo

The next couple of weeks followed a predictable pattern. More purchases for Emma, more laundry for me, but she did release me once, allowing me to masturbate outside her window while watching one of her erotic acts.

But still I was getting nowhere with Nicky, and I was desperate to make amends with her so we could have penetrative sex, something I would never get with Emma.

Moreover, the summer was passing quickly by, and I knew that very soon Emma would be returning to college and wouldn't be returning home until the end of the Fall semester. What I didn't know was what would become of me while she was away. Would she somehow keep our game going from afar, or would she unlock me until Christmas? If the latter, it was essential I made up with Nicky to take advantage of the freedom.

A series of emails one morning sealed my fate.

“Anon”: “I return to college tomorrow, sissy...”

The message was brief and blunt and unhelpful. I waited to see if there would be a follow-up that would throw more light on arrangements. Sure enough, a few minutes later another message came, and it took the form of a bomb.

“Anon”: “If you want to be released before Christmas... convince Nicole to be a keyholder...”

I felt physically sick. No way could I last until Christmas without release. Nicky did not have the faintest inkling that I was locked into a chastity device, yet this throwaway message from Emma told me Nicky would become responsible for deciding when—if—I get unlocked.

I was still processing this shock when a third message came in.

“Anon”: “Visit Nicole's apartment in the next couple of days... Wear cartoon panties... Enjoy... See you at Christmas... I'll tell you what to buy me - LOL...”

My world was falling apart. Emma saw me as a submissive sissy, but the image I had portrayed to Nicky had been completely masculine—we were a couple who enjoyed wild and adventurous sex. Suddenly, Nicky was to see me very differently.

If I wanted release, I had no option but to comply with Emma's orders. I had to lay my cards on the table, and convince Nicky to be a keyholder, no matter how mortifying that conversation would be.

oooOOooo

I dialed Nicky's number, and she was quick to answer. “It's you,” she said, in her sultry voice. “I hope you're phoning to say you've ditched that whore.”

“It's... it's complicated, Nicky, what with her being my neighbor.”

“So you said, but complicated doesn't mean impossible.”

“Sure, but the good news is that she's going to be away until Christmas.”

Nicky snorted, “Are you saying it's just you and me until Christmas, and then this bitch returns to join in the fun?”

“No, that's not what I'm saying. But I need to talk to you, Nicky, face-to-face. I have to explain something.”

“What do you have to explain?”

“I can't say over the phone because it's something you need to see. Can I come around this evening?”

“I suppose so, but don't think you're getting nooky.”

She didn't know how true her words were, but that evening she would find out.

oooOOooo

I arrived at Nicky's apartment, and she opened the door to me. She gave me a peck on the cheek, but nothing more. Clearly, I had a lot of convincing to do if she was to forgive me for two-timing her.

She fixed me a bourbon, and we sat down facing one another in her lounge. “What is it you need to explain face-to-face, Mark?” she enquired. “It had betta be good.”

I didn't know what to say, but procrastination wasn't going to help. “I'll come straight out with it, Nicky,” I said. “I'm locked in a chastity device.”

The expression on her face changed as I watched. Initially, it was one of bafflement, trying to make sense of what I was telling her. But then it morphed into enlightenment and finally to downright amusement.

“What the hell,” she laughed. “Are you telling me, right now, here in my apartment, that your dick is locked up? Yeah?”

“Ye... yes, I am,” I replied, my face burning.

“Why?”

“Er... Emma makes me wear it,” I replied.

“She makes you?” Nicky could barely conceal her mirth. “Is this why you keep saying you don't have sex with her—because you can't?”

“Hmm...”

“Oh, my God, this I've got to see. Come on! Show me!”

In many respects she was taking this far better than I expected. I thought she might be appalled, disgusted even, but she seemed to relish the idea. What's more, she obviously understood what a chastity device was, sparing me the embarrassment of having to explain.

I stood up but hesitated, plucking up the courage to lower my jeans.

She was frantically nodding her head, urging me to show her my cage. I undid my jeans and pulled them down, revealing my mauve cotton panties with a cartoon image of Goofy.

“Oh, my God,” she screeched. “Why are you wearing those?”

“Er... well—”

“Does Emma make you?”

“Hmm... yes, she does.”

“Oh Marcia, you look so cute and wholesome in your pretty panties...” she mocked.

“Please, Nicky! It's not funny.”

“Looks funny to me. Pull your panties down.”

Reluctantly, I did what she asked, and she dropped down onto her knees in front of me to examine the cage in detail. “Oh, my God!” she exclaimed. “That is some expensive looking cage. I can't see any way of breaking out of that.”

She lifted it up and wiggled it around. Despite my humiliation, I was well aware of my penis trying to expand. “Hang about a bit,” she said, looking puzzled. “Where's the padlock? Where's the keyhole?”

“That's the problem, Nicky. It's controlled remotely, through an app.”

“Really! Wow!! That's proper twenty-first century tech, isn't it? How's it work?”

“The cage is connected by Wi-Fi and Bluetooth to the phone. In fact, my phone and Emma's.”

“Oh?! So, if you've got the app, why can't you unlock it?”

“Er... because it's set up so that both Emma and I have to instruct it to unlock.”

“Aah! I see! Yes! This is so cool! She's in charge, yes?”

“Yes, but the thing is, Nicky... as she's going away, she wants you to be a keyholder as well. Otherwise, Emma says I won't get free until she gets back at Christmas.”

“Oh, heaven's. This is really turning me on, Mark. I'm getting damp thinking about this. So, if I get to be a keyholder, then I control when you're free.”

“Unfortunately, yes!”

“Why unfortunately? I love the darn idea. What do I have to do?”

I had expected to have faced more of a battle convincing Nicky to be a keyholder, yet her keenness was worrying. Nevertheless, I had no choice but to go along with it and we spent the next half-hour installing “Keyholder” on her phone and linking the device. Then, once she had the password to my account, she officially had control.

I watched as she excitedly pressed “unlock”. Nothing happened. “Eh?” she asked.

“It needs Emma to unlock it as well. And me too, but that's obviously a formality.” I tried to force a laugh.

“So, er...”

“You'll see there's secure messaging with the app so you can contact Emma, but she'll first have to make you an administrator, so you have the same privileges as she does. You can both contact me, but I can't contact you.”

“That's so cool. When will I become an administrator?”

“I guess Emma will see on the app that you've joined.”

“Yeah, right... And what does 'Zap'—”

“No, don't press—” Before I could finish, she had pressed the button and a pulse of electricity blasted through my genitalia, causing me to collapse onto the floor. “I... I said... don't press that, Nicky.”

“Don't you take that tone of voice with me, Marcia. Unless you want another zap. Understood?” she asked, sternly.

“Yes, sorry, I understand.”

“Ma'am. Call me Ma'am!”

“I understand... Ma'am.”

“Good. You can go now... go home.”

“Don't you want to contact Emma?”

“You said I can't, not until she makes me an administrator. Go on! Off you go. Be a good boy... or rather be a good girl,” she remarked. “You and I are going to have fun this Fall... well, one of us more than the other, I suppose.”

I turned to look at her. Her face now bore an inscrutable smile, not dissimilar to Emma's.