This is a true story about the disaster that was my first ever really life experience with chastity. I've changed my old boyfriends' name for the story. I hope you enjoy. It happened 6 years ago. Obviously, I wouldn't make these mistakes now, I'm much more experienced, hehe.

My first chastity experience.

So there I was, 23 and curious, eager to explore new avenues of pleasure with my boyfriend at the time. He was your typical bad boy—tall, muscular, older, oozing with that confident, dominant vibe that some women find irresistible. In hindsight, he was an arse, but back then, I was young and intrigued by his brand of physical dominance.

We had been together for seven months when we planned a trip to Egypt, a chance to explore a new country and, little did I know, a chance to explore a new side of our sexual dynamics. A few days before our holiday, we found ourselves delving into a conversation about fantasies. His was predictable: the classic male fantasy of a threesome with another girl. I shut that idea down immediately; it didn't excite me in the least. Then he suggested anal sex. I had never tried it, and I figured why not give it a go? But I had a condition: he had to submit to my control for the first five days of our vacation. That meant wearing a chastity cage and giving me the key.

At first, he wasn't keen on the idea. Like most men, he saw chastity as something that took away from his masculinity. But I managed to convince him that it would heighten his pleasure and make the eventual release all the more intense. So, curious and a little hesitant, he agreed.

I'll never forget the look on his face when I locked the cage around his cock. It was a mix of excitement and trepidation, his eyes daring me to take this journey with him. I kissed him deeply, my lips teasing and my hands exploring, making him ache for release from the very start.

We arrived in Egypt, and as we checked into our resort, I could sense his frustration growing. Being locked up in a foreign country, surrounded by beautiful scenery and the allure of anonymity, only added to the tension. I, on the other hand, was relishing every moment of it. I loved having him at my mercy, his desire simmering just below the surface, waiting to be unleashed.

Now, my boyfriend—let's call him Jake—had always been sexually vanilla. Our love life had been predictable and, frankly, a little boring. But he had no idea that each time I went down on him, I was edging him, bringing him to the precipice of release only to pull away at the last moment. He thought I simply adored worshiping his cock, and his ego convinced him that my devotion was the reason I never let him finish before edging him a few times.

On the first day of our vacation, after an exhausting early morning flight, we unpacked and prepared for a day by the pool. I decided to wear my sexiest bikini, a skimpy black number that accentuated my curves, my breasts virtually bursting out. The side boob was so cruel, I loved it. My hair, dyed a vibrant pink at the time, was styled in playful pigtails, an ode to the schoolgirl fantasy I knew he had.

As we made our way to the pool, I could feel Jake's eyes on me, burning with a mixture of lust and frustration. The cage beneath his swimming trunks was a constant reminder of my control, and the Egyptian sun only added to his discomfort.

We laid out by the pool, and I made sure to put on a show, lounging seductively and dipping my feet in the water, letting my eyes drift closed in pleasure. The sun felt amazing on my skin, and the slight breeze made my nipples harden, creating an enticing sight for Jake and any other lucky spectator.

"God, your breasts look incredible," Jake groaned, shifting in his seat. "I can't take much more of this, Sasha."

"You can and you will," I purred, reaching over to stroke his thigh. "Besides, think of the payoff. My tight little ass is all yours in a few days. That thought should keep you nice and hard... or it would if you weren't locked up." I chuckled, my fingers teasing the hem of my bikini bottoms.

The sun was blazing, and I felt the heat on my skin as I lay there, teasing my poor boyfriend. It was time to up the ante, so I asked him to rub some sunscreen on my back. As he obligingly began to apply the lotion, his hands trembling slightly, I shifted, presenting my ass like a gift, my cheeks peeking out from the sides of my tiny bikini bottoms [Author side note, to this day I still think my ass is my best feature] .

"Mmm, that feels amazing, baby," I purred, arching my back slightly. "Don't forget my legs... and my ass. It's so easy to get burned here."

Jake's breath hitched as he realized my intent. His hands shook even more as he squeezed a generous amount of sunscreen onto my ass, his fingers tentatively tracing the curve of my cheeks. I sighed in pleasure, savoring the sensation of his touch, and his frustration.

"That's it," I murmured, goosebumps forming despite the heat. "Nice and slow. Imagine if we didn't have our little agreement. I'd be riding you right now, taking that thick cock deep inside me."

"Fuck, Sasha," he groaned, his voice hoarse. "You have no idea how much I want to tear that cage off and bury myself in you."

I giggled, a mischievous glint in my eye. "Oh, I have a very good idea. And that's exactly why I know you'll behave and do as I say."

We spent the rest of the day by the pool, flirting and teasing, my bikini-clad body on display for his eyes only. The sexual tension was palpable, and I knew Jake was struggling to contain himself. As the day progressed, the anticipation of what was to come that night grew.

As the sun dipped below the horizon, we retired to our room, both of us eager to freshen up before dinner. I couldn't deny the electric tension between us, and as soon as we stepped into our room, I found myself pressed against the door, Jake's lips crushing mine with urgency. At first, I melted into the kiss, my body responding to his touch, but then something shifted.

He pulled away momentarily, a hungry look in his eyes, before grasping my wrists and leading me towards the bed. In one swift motion, he threw me down onto the mattress, his body overpowering mine. Back then, I enjoyed this dominant display, the thrill of being taken control of. But now, as I recall that moment, I can't help but feel a little sick at being submissive towards anyone.

Jake tore at my bikini, his fingers clumsy in their haste, exposing my breasts and then reaching for my bottoms. In his passion, he forgot about the chastity cage, his mind clouded by the raw need to possess me. I remember how he knelt between my legs, his eyes dark with desire, and then how his face fell when he realized the cage was still locked in place.

"Not yet," I giggled, rolling off the bed and standing before him, my naked body a stark contrast to his frustrated state. "The cage stays on a while longer. I haven't granted your release just yet."

I sauntered towards the bathroom, feeling his eyes on me as I went, his frustration palpable. "Go take a cold shower, baby," I called over my shoulder, a playful tone masking my satisfaction at his predicament.

I'll admit, after a day of teasing and flirting, I was exhausted. The cocktails by the pool didn't help, and by the time we returned to our room, I was ready to pass out. Jake, on the other hand, was wide awake and full of pent-up energy.

"Come on, Sasha," he said, his eyes burning with desire. "Let's take advantage of that big comfy bed."

I flashed him a cheeky smile. "Sorry, baby, but I'm beat. You can order a movie or something. I'm hitting the hay."

As I curled up in bed, I heard Jake mutter something about "going back downstairs for a drink." I didn't care at that point; my eyes were already closed, and sleep was pulling me under.

The next morning, I woke up feeling refreshed and ready to tackle the day. That feeling quickly evaporated when I turned to find Jake still asleep, a miserable sight with his mouth agape and a hangover imminent. I rolled my eyes, remembering how he'd stayed up late at the hotel bar, probably flirting with the waitresses. What a fucking cheat he ended up being!

I decided to make the most of the morning and headed down for a swim. The water felt amazing on my skin, and I relished the freedom of swimming laps without Jake's eyes on me for once. After a invigorating swim, I claimed a lounger and decided to work on my tan.

The sun was scorching, and I slathered on some sunscreen, paying extra attention to my breasts and ass, ensuring an even tan. I closed my eyes, feeling the heat on my skin, and let my mind wander. I thought about Jake and the cage still locked around his cock. A smile played on my lips as I imagined his frustration, his desire for me building with every passing moment. Little did he know, I had no intention of releasing him from his captivity anytime soon.

As I lay there, my body soaking in the sun's rays, I could feel eyes on me. I cracked open an eye, spotting a handsome man a few loungers down, his gaze fixed on me. I smirked to myself, enjoying the attention, before closing my eyes again, pretending to be oblivious to his interest.

It thrilled me to be the object of desire, to have a stranger lusting after me. I knew Jake would be downstairs soon, and the thought of him finding another man admiring his girlfriend only added to my arousal.

I pictured Jake's face when he saw me, his hungover haze clearing as he realized I was on display for another man. Perhaps he'd even recognize the stranger from the night before, maybe he'd stayed up drinking with this guy at the bar.

After another hour or so, I decided to head back upstairs to our room. Jake was probably awake by now, and I wanted to check in on him, see if that hangover had cleared.

As I slid into bed, Jake stirred, his eyes half-open and bloodshot. I giggled, reaching over to caress his cheek. "Hey sleepyhead, how're you feeling?"

He groaned, his voice rough from sleep. "Like I drank too much last night. Where'd you disappear to?"

I shrugged, my hand sliding under the covers to unlock the chastity cage. "I went for a swim and then laid out by the pool. I wanted to give you some time to recover."

Jake's eyes widened as he felt the cage being unlocked, his cock springing free. "Sasha, what are you--"

I cut him off with a soft moan as I moved under the covers, taking his length into my mouth. I savored the taste of him, the feel of his shaft on my tongue. I knew how much he'd been craving this, and I wanted to make it worth the wait.

My lips teased the head of his cock, my tongue swirling around the tip before taking him deeper. I love giving blowjobs, and to this day, I still get off on the power it gives me, although it's been a while since I last did it. I took my time, my lips gliding up and down, my hands gently caressing his balls.

I swirled my tongue around the head, teasing the sensitive underside before taking him deeper, my lips wrapping tight around his shaft. I moaned softly, the vibration sending shivers through him. I pulled back, my lips kissing and sucking gently, before diving back down, my mouth warm and wet around him.

Jake groaned, his hands tangling in my hair, his hips instinctively thrusting upward. "Fuck, Sasha, that feels so good."

I hummed in response, my mouth never leaving his cock. I knew exactly what I was doing, the years of practice evident in my skilled movements. I swirled my tongue, tracing the veins, my lips tight around him as I bobbed my head, my hand stroking what I wasn't able to fit into my mouth.

I knew exactly when he was close; his breathing changed, his hips jerked, and a soft moan escaped his lips. But just as he was about to explode, I stopped. I pulled my mouth away, his cock slick with my saliva, and sat up, a playful smile on my face. I held the chastity cage up to him, tapping the side of it with my nail.

"Time to lock you back up, baby," I purred, my voice dripping with satisfaction.

"No, Sasha, please," Jake protested, his voice hoarse with need. "Don't stop now. I was so close."

I laughed, a soft, musical sound that danced in the air between us. "I know, and that's exactly why I'm stopping. Besides, don't you want your reward in three more days time?"

I could see the memory returning to him: the promise of anal sex, my tight ass clenching around his cock. His eyes darkened with desire, the brief frustration of being denied release forgotten.

"That's right," I continued, my fingers tracing the outline of the cage. "In three days, this tight little ass is all yours. But until then, I'm in control. And right now, I want you locked up and aching for me."

That night, I made sure to keep a clear head. No excessive drinking, no distractions. I wanted to savor every sensation, every twist and turn of this power play.

Back in the room, I wasted no time in taking control. I pushed Jake down onto the bed, his eyes wide with anticipation as I climbed on top of him. My fingers trailed along his chest, toying with the hairs as I straddled him, a coy smile playing on my lips. He tried to kiss me, but I pulled away, shaking my head with a slight smirk.

"Not like this," I whispered, my breath hot against his lips. "Tonight, you please me."

I watched his Adam's apple bob as he swallowed, desire and a hint of nervousness flashing in his eyes.

"Anything you want, Sasha," he murmured, his voice strained as he struggled to adjust to this role reversal. "Just tell me what you need."

I ran my fingers through his hair, guiding his head gently down my body, towards the heat between my thighs. "Use your mouth," I commanded, my tone browed and demanding. "Show me what that tongue can do."

I felt his breath on my inner thighs, his lips planting soft kisses along my skin as he made his way closer to my core. A shiver ran through me, a mix of anticipation and the thrill of having him completely at my mercy. Even now, the memory of that moment sends a tingle down my spine.

Jake's tongue teased the sensitive skin of my inner thighs, his breath warm against me. He hesitated for a moment, as if seeking unspoken permission, before finally, finally, his mouth found its target. His tongue flicked out, gently probing, eliciting a soft moan from me.

Ordinarily, I don't cum from oral sex. It's always been difficult for me to reach that peak, but something about that night, about having Jake in chastity, about the power dynamic that had flipped, pushed me closer and closer to the edge. His mouth was relentless, his tongue a blur of motion, sipping at my juices, his nose nuzzling my clit, sending shocks of pleasure through my body.

I whispered encouragements, urging him on, my hands tangling in his hair, guiding him. I felt the pressure building, a coil tightening within me, and I knew I was close. "Right... there," I gasped, my hips bucking involuntarily. "Don't... stop."

I felt the moment it happened. A shockwave ripped through me, my back arching as a cry escaped my lips. My eyes clenched shut as I surrendered to the sensation, my hands gripping Jake's hair tightly, as if to anchor myself in the moment.

As the waves of pleasure washed over me, I felt Jake's hands on my thighs, kneading gently, his tongue still flicking lazily, drawing out every last drop of ecstasy. When I finally came down from my high, I collapsed onto the bed, my body spent and satisfied. I opened my eyes to see Jake looking up at me, a mixture of awe and hunger in his gaze.

"Not so fast," I pouted, my finger raised in objection. "I want you locked up a little longer. Go back to sleep."

I giggled at his annoyed expression, giving him a quick peck on the lips before snuggling into his arms. I fell asleep feeling satisfied and in control, with Jake's frustrated groans music to my ears.

The next morning, I woke up feeling well-rested and eager to continue my torment of Jake. I announced my plan to go for a swim, deliberately flashing him a cheeky smile as I slid into my bikini. I could see the disappointment in his eyes, knowing that another day would pass without release. Oh, the power I held!

As I brushed my teeth, preparing for my swim, I heard a rustling sound coming from the bedroom. My heart skipped a beat as I realized Jake was probably searching for the key to the chastity cage. I kept that key close at all times, locked safely in my small travel jewelry box along with my earrings, nose studs, and lip rings.

I popped my head out of the bathroom, a playful smile on my face, to find Jake indeed rummaging through my stuff.

"Looking for something?" I teased, feigning ignorance.

His face flushed, and he mumbled something about needing to use the safe. I knew he was lying, and it only added fuel to my playful fire.

"You know," I said, a coy smile on my face as I stepped towards him, "I was thinking of taking the key with me to the pool. You know, just in case someone tries to get naughty while I'm gone."

Jake's eyes widened at the suggestion, and I could see the worry creasing his forehead. I sauntered over to him, my hips swaying seductively, and held up the key, dangling it teasingly before his eyes.

"Don't worry, baby," I cooed, attaching the key to an ankle bracelet. "It'll stay with me while I swim."

In hindsight, taking the key with me to the pool was a stupid idea.

So, I strutted down to the pool, my hips swaying with every step, the key jingling lightly with each stride. I felt powerful, in control, and incredibly sexy. I claimed a lounger by the pool, settling in to soak up the sun. As I lay there, my eyes closed, I imagined Jake upstairs, his desire and frustration growing by the minute.

I was halfway through my laps when I spotted Jake approaching, a towel in hand. I waved, taking a break, and he handed me a bottle of water. I used the opportunity to showcase my body, sliding out of the pool, ensuring he got an eyeful of my breasts.

But Jake wasn't looking at my cleavage; his eyes were fixed on my feet. "Where's the ankle bracelet?" he asked, his voice tight with concern.

My heart froze as I realized it wasn't there. Panicked, Jake dove into the pool before I could react, and together we frantically searched for the bracelet and the precious key it held.

Relief washed over me when Jake's hand closed around the bracelet at the deep end of the pool. It must've slipped off when I was kicking off the side.

As soon as Jake realized the key was safe, his demeanor changed. He snatched the bracelet from my hand and dried it off. His eyes blazed with a mixture of relief and anger as he stormed off back to the room. I followed close behind, apologizing profusely, but he wouldn't listen. I wanted to explain, to tell him that I would never actually lose the key, but he wasn't in the mood for excuses.

Back in the room, I found Jake sitting on the edge of the bed, his hands fumbling with the lock. I knew he was furious, but a part of me was turned on by the sight of him struggling to free himself.

"Baby, wait," I pleaded, placing a gentle hand on his shoulder. "I'm so sorry, I shouldn't have taken the key. Let me have the key back, and we can pretend this never happened."

Jake shook his head, his jaw clenched. "No, Sasha. I've had enough of this. I'm taking it off now."

I could see the determination in his eyes, and I knew there was no point in arguing. I slumped onto the bed, a wave of disappointment washing over me. "At least let me do it," I murmured, reaching for the key.

Jake pulled away, standing up. "I think I can manage. You've controlled me enough these past few days."

His words stung, and for a moment, I wanted to argue, to remind him that it was his idea to try chastity in the first place. But I held my tongue, remembering that it was partly my fault for taking the key.

With a final click, the cage came off, and Jake let out a sigh of relief. He rubbed his cock gently, a mix of pleasure and frustration playing across his face.

I smiled softly, my disappointment giving way to a twinge of desire. "Now that you're free, why don't we--"

"I need a minute," Jake interrupted, cutting me off. "I just... I need some space, Sasha."

I felt hurt, not going to lie. I wanted to scream at him for being so selfish, for ruining what could've been an amazing power trip for me. As i write this I a small part of me wishes the key had been lost, wished he'd been stuck in that cage a forever. It's was a bitter thought, but I couldn't deny the satisfaction it would've brought me, especially after discovering how much of a cheating bastard he was..

In the end, I didn't lock Jake back up. I let him have anal sex with me that night, like he'd always wanted. It wasn't great, and it certainly wasn't worth the buildup. I know some women enjoy it, but I'm not one of them. It was the first and last time I let anyone fuck my ass.

There you have it, dear reader. An ending that wasn't quite as explosive as I'd hoped, but an ending nonetheless. Jake got his release, and I was left with a bitter taste in my mouth and a sore ass.