My First Chastity Experience

*Note*

This is a mostly true story, with names changed and parts filled in where there are holes in my memory.

This happened years ago with my then Mistress. I had had a kink for chastity for awhile, but had never acted on it on my own. I did not see the point, as I figured I would not have the self control to be my own key holder for any length of time. However, when I brought it up to my Mistress, she seemed interested in chastity at least on a scene by scene basis, so we began looking at cages. We settled on a metal, bird-cage style chastity device, which would end up having a lot of issues, but luckily they are not relevant to this little tale.

She and I usually manage to play about once a week, at her house and so, a couple weeks after picking out a cage, I get to her place to find her working out. Without missing a beat while running on her treadmill, she orders me to go up to her room, strip, and kneel in front of the bed. Again, this is not unusual for our dynamic. She will typically lay all the items she intends to use for play that evening on the bed, making me sit and stare at them, naked, while waiting on her to finish up what she is doing. She knows it makes my overactive imagination run wild and loves the tease.

I get up to her room and find nothing but the chastity cage we had looked at, placed very purposefully, in the middle of the king-sized bed. As per usual, I strip down, neatly fold my clothes and place them on the nearby dresser before kneeling on the hardwood floor in front of the bed. Waiting there, with the cage on prominent display in front of me, was a bit maddening. Given the lack of any other toy, I wondered if she was simply going to lock me up and send me on my way, or what other plans she might have. Of course, as mentioned before, she wanted me to overthink the situation.

After what felt like an hour, she came up to the room. Per her training, I did not move an inch from my position as she moved around behind me, though I could hear a rattle and the distinct sound of glass being played on a coaster behind me. Finally she stepped between me and the bed, still clad in her sweaty workout attire, tight bike shorts and a sports bra. Stepping forward, she placed one of her bare feet under my crotch, while her other leg swung up and over my shoulder. She had several inches on me, height wise, so it was not a very difficult maneuver and with the leg over my shoulder, she both pulled my face into her lycra-clad crotch, and pushed me down just enough such that my cock and balls were resting on her other foot.

No orders came, so I was to simply kneel there, my face pressed deeply into the crotch of her shorts, breathing in both her sweat and her very apparent arousal. My cock, which was already semi-hard from the anticipation before, was not rigid and pressed into her foot, which she flexed upward, pressing into my cock and balls. It was not long before I was leaking precum all over her foot as she continued to hold me in place, grinned on my crotch with her foot, and started to grind her own crotch into my face.

After a few, blissful minutes, she released me and sat back on the bed. Raising the foot that had been underneath me, she snapped her fingers and told me to clean it. My precum glistening before my eyes made it pretty obvious what she meant, and so I leaned forward and dutifully lapped my own mess from her foot. I figured I might clean her whole foot, licking off the sweat from it being trapped in her socks and workout shoes, but my initial attention prompted laughing from her, apparently being more ticklish than usual today, and so she stopped me as soon as the cum was cleaned off.

Standing, she picked up the cage and dangled it, teasingly, before me before patting the bed and ordering me to get up and lay on my back. As I did she went to the dresser and I saw her retrieve what she had placed there before, a bowl of ice. I had read enough chastity literature to have an idea what that was for. She had probably purposefully gotten me raging hard just so she could watch me squirm under the tough ice. After all, having just been shoved into her crotch, I was not getting soft very soon.

I lay on the bed as instructed and she climbed beside me, with the bowl of ice and cage in hand. Straddling my chest, she lay the bowl and cage down beside my crotch and chided me, playfully, for being hard. She teased that she would have to find a way to make me soft again or I would never fit in my little metal cage; as if she had not been the direct cause of me being hard and planned for it the whole time. Taking a cube of ice, she initially pressed it against the head of my cock, causing me to involuntarily buck and squeal. Knowing her, she probably also knew I would have such a reaction, and wanted it just so she could chide me further.

She told me she could not have me moving so much, and that maybe a little less oxygen would help settle me down. With that she moved her ass backward and lifted herself onto my face. My nostrils were once again filled with the scent of her workout and arousal, with a damp spot in her shorts to match, but now her weight pressed down on my head and there was very little air to come by. Of course, this only made me more hard, but I imagine that is exactly what she wanted; any excuse to torture me with the ice. And torture me she did.

With her ass holding my head firmly in place, she began rubbing ice cubes all over my cock and balls. Now I typically consider myself a pretty compliant submissive. If a Domme tells me not to move, I don't move. But between the ice and the lack of air, I definitely squirmed even more than I would under a harsh beating. This only caused my Mistress to grind her crotch into me even harder and use the ice more readily. Occasionally she would grab me by the hair, lift herself off and adjust her position, giving me precious few seconds of fresh air, but this little dance continued on for what must have been a few minutes. My cock was at war between wanting so badly to be turned on, while also wanting to retreat from the biting cold, but eventually the ice won that fight.

When I was finally flaccid enough, my Mistress slipped my cock and balls through the hard metal ring. A little more ice was required after this to get me soft again and finally attach the metal cage around my cock. I could not hear much of anything, with her thighs clamped down on either side of my head, but I felt the click of the lock as she closed it, ensuring the only way to free my own cock, was with her permission. With the cage on, she ground herself into my face for a little while longer before dismounting me and climbing off the bed.

She stood there, smiling at her handiwork while I pant on the bed. She then ordered me to go inspect myself in the bathroom mirror, to see what I thought. I did as I was told, examining myself, lifting the cage, seeing my poor, hard cock, trying to break out, feeling the weight of the metal and the pressure of the confinement. It was like nothing I had ever experienced before. I am a pretty horny guy, and I masturbate a lot, so there was a particular thrill from having that ability completely removed and now at the whim of someone else.

I exited the bathroom to find her propped up, comfortably, against the headboard of the bed as she casually flipped through TV channels. She spread her legs and told me to come sit. Climbing the bed, I sat between her legs, my back pressed against her sports-bra clad chest. She found what she was looking for on the TV, some bodice-ripper of a movie, complete with lurid sex scenes. It only took a few minutes of watching for two of the characters to start making out, stripping, and fucking. As the scene progressed, I felt one of my Mistress' hands slip between us and start to rub her crotch over her workout shorts.

As the two characters fucked on screen, my Mistress leaned into me and whispered that it was too bad my cock was all locked up, otherwise she might have let me fuck her like that, because she really needed a cock right now. With that, she swung her legs over mine, and used them to pull mine apart. With my legs spread, she reached around me and started fondling my full, aching balls and caged cock. She toyed with me, all while we watched the sex scene on TV and she herself continued to masturbate. Before long, she was moaning into my ear, giving herself the pleasure I could not have. Finally, she came a powerful, shaking orgasm. She pulled me in tight, a hard grip on my caged cock and balls, and let out a deep, guttural moan as she came.

She shivered and held me tight for a minute in the aftermath, before a noise from the bedroom door roused my attention away from her pleasure. There stood her husband, with a deep smile on his face. He made some comment about how fun that sounded, and hoped she had more for him where that came from. She got up from the bed to go kiss him in greeting and handed him the keys to the lock on my cage. She told him that she needed to shower before they did anything, but in the meantime, he could use me for a warmup.

With that, she nearly danced off to the bathroom and shut the door. Her husband on the other hand, looked at the keys, then at me, still sitting on the bed. With a hunger in his eyes we walked over to the bed, and I knew my night was just beginning. But this has already been a monster to type, so I will save that part for later.

My Mistress' husband pocketed the keys to my cage and stalked over to the bed, where I sat naked, caged, horny, and dripping. He and I didn't have a D/s relationship, but we did have a sexual one. Sometimes it was just fun between the two of us, sometimes my Mistress would use me as a surrogate to keep her husband happy in what I would later realize was an unhealthy way. But for this story, everything worked out, and at the time I was way too into our relations to see the red flags.

Anyway... my Mistress' husband, who we will call Lucas, climbed onto the bed and crawled over, pushing me back against the pillows. He immediately crawled on top starting making out with me. Even as his tongue pushed past my lips, his hands wandered south. They stopped at my nipples first, before continuing on down to my crotch. Lucas took his time exploring the cage, feeling it out with his hand. Due to making out, which I am a slut for when subby, I was straining against the bars of my prison.

Lucas rubbed up and down my encaged shaft, faux jacking me off, despite the fact that I could hardly feel a thing. He then began to feel around the ring and gently fondle my balls, taking his time to fully feel out my situation. He reluctantly broke off our little make out session to sit up and take a visual inspection of the cage; unceremoniously adjusting me now to take stock of it. He took a while in his inspection, probably because this was his first encounter with such a device, whereas my Mistress and I both were at least familiar with the form. Lucas said that it was kind of cute, but also a little bit sad to see it all locked up. But it must not have been that sad for him as he stepped off the bed and unceremoniously removed his pants and underwear.

Climbing back onto the bed, Lucas mounted my prone form, climbing onto me such that his knees pressed my shoulders back into the bed and his cock came to rest over my mouth and nose. He was not my Dom, so I needed to take no order from him to take the initiative and take him into my mouth. From my pinned position, I bobbed my head on his shaft as best I could, but he soon helped me out, taking a fistful of hair in one hand and forcing his cock down my throat. Luckily, by this time, I was well trained on his cock, and could take him with minimal gagging. I sucked and licked his wonderful cock all while he pinned me down and fucked my face.

It did not take too long for him to start panting and groaning in pleasure as he fucked my face. My cock was twitching needily in its cage, when I felt a hand grip both of my thighs and push my legs wide and high. Being so focused on Lucas, I had not heard my Mistress come back in, fresh from the shower. She pushed my legs wide and high and the next thing I felt was her tongue circling my asshole. She rimmed and probed me with her tongue, even as my own circled her husband's cock. It was agony and ecstasy, as the couple continued until, in a loud moaning grunt, Lucas shoved his cock as far into my mouth as he could, and coated my throat with a load of his cum. With that, he dismounted and my Mistress ceased her licking, letting me lay prone and panting on the bed.

My Mistress, still dripping wet, and with the shower still running in the background, pulled her husband back toward the bathroom, removing his shirt as they went. As she closed the door to the bathroom she looked at me with a mischievous grin and told me not to cum while they were gone. Then giggling, she shut the door and I was left alone with nothing but the faint sound of running water. I sat there for a minute, listening to the sounds of the water change as the two of them showered, but then I started hearing the distinct sound of my Mistress in pleasure.

She moaned, and exclaimed approval for whatever was happening in the shower. It was loud enough, over the sound of the shower and the closed door, that I am certain she was purposefully increasing her volume for my sake. Her moaned approvals only got louder and more frequent over the course of their time in the shower until she apparently came to a screaming orgasm that echoed in my ears and made my cock throb in its cage. In the meantime, I had absent-mindedly been stroking myself over my cage, not that it had done any good whatsoever.

Finally the shower stopped and luckily I had the peace of mind to take my hand off my cock. My Mistress soon opened the bathroom door, eyeing me with a sly smile as she returned, still naked. She walked over to the bed, climbing up by my feet and crawling forward just enough so that she was on all fours and her head hovered just above my locked cock. Her husband soon joined us, also naked and rock hard again. My Mistress lowered her face until it was right in front of my cock, raising her ass and shaking it enticingly at her husband as he walked over. He needed no instruction, or they had discussed this before hand at least, as he mounted and fucked her right there.

Lucas spent no time with slowness or foreplay, going straight into a hard rut, as my Mistress was fucked, face down, ass up, directly in front of me. Once again putting on a show, she moaned loud and often, staring directly into my eyes as she was railed from behind. I was stuck sitting there, unable to even masturbate, as the couple fucked with wild abandon in front of me. Turned-on does not do justice to the state I was in, and I am sure I had a dumb look on my face as I just stared back at my Mistress while she was pushed forward with each hard thrust. Aside from the feeling of the bars closing tight around my trapped cock, I could feel her hot breath on my member, as she moaned in pleasure right next to me and I began to involuntarily hump the air, looking for anything to grind my need against. This prompted nothing more than a giggle from my Mistress as she took hold of my balls with one hand and held me still.

For his part, by this point Lucas was also moaning quite loud, though not putting on the same show as my Mistress. As the pitch in his moans changed, my Mistress told him not to cum and to pull out of her. He groaned out his reluctance, but complied and backed off. My Mistress then crawled further up the bed, positioning her ass once more above my head, and turned around. She told her husband to dumb his load into me, which he seemed satisfied with. He crawled onto the bed as well, taking me by the ankles and lifting them over his shoulders. Slicked with his wife's juices, and his own, he slipped into me without too much trouble and began thrusting. I moaned my approval as the head of his cock rubbed over my prostate, but this still caused my cock to strain in its own confinement.

I did not have long to dwell on the feeling of being fucked in chastity, as my Mistress simply told me to make her cum, before lowering her ass onto my face. She slid herself around for a second, adjusting herself until my mouth was well positioned to lick her clit, and my nose was firmly pressed into her asshole. I did as she had trained me to do, licking her clit as best I could from this position. As I worked I continued to feel Lucas thrusting into my ass, speeding up and thrusting harder as he went. The situation was like a dream, but the need I had for something, anything at all, to stimulate my neglected cock is indescribable. But then, that is the thing about chastity; it made it clear that in that moment, my pleasure was not the focus, instead only the pleasure of the couple mattered.

While I continued to lick my Mistress, I felt her bend over, reaching to the side of the bed before returning to her original position. I did not have to guess at what she had retrieved because I could feel the buzzing a second later. Her hitachi had joined the party, buzzing so close to where I was licking that I could feel it all the way down my tongue. She also began to grind against me, so I could tell she was quickly getting close, even if I could barely hear anything with her thigh clamped down on either side of my head.

Lucas would end up finishing first. I felt a few particularly deep, slow, thrusts before he hilted himself in me and dumped his second load into me for the evening. As he finished, my Mistress briefly paused in what she was doing, though I knew better than to stop licking, and I heard her and her husband have a quick, muffled exchange. It would not take long to figure out what she had asked of him as, within a few seconds of him pulling out of me, I felt the distinct cold touch of a steel plug being shoved into my ass.

With Lucas' cum now trapped inside me, my Mistress resumed grinding into my face and pressing the vibrator into her pussy. I eagerly lapped at her clit as her wetness flowed down onto my face and mouth. Somewhere down south, her husband began to toy with my caged cock. I was so thankful for any attention on my aching member that I thrust up against his hands, though it once again amounted to nothing. Before too long, though with my tongue getting pretty fatigued, my Mistress clamped her thighs even harder on either side of my head and came to a convulsing orgasm. I almost felt like she might crush my skull as she sat there riding out the waves of pleasure, but I did not stop licking either; she would tell me to stop or she would get off of my face, otherwise my tongue would do its best.

Finally she eased up the pressure and dismounted from my face. She crawled over to her husband and began making out with him, while I was once again left lying on the bed watching. After a couple of minutes, their mouths parted and she turned her attention back to me. She inspected my cage with a giggle, noting just how much my cock was straining for release. She told her husband she was still horny and that they should quickly wash off his cock for later use. As they once again turned toward the bathroom, she smiled at me and told me to get dressed, and leave the cage on.

I did as I was told, getting dressed while caged, plugged, filled, and unbelievably horny. They came back not long after I finished and almost immediately returned to the bed. As I stood by watching, my Mistress pushed Lucas down on the bed and climbed on top of him, cowboy style. She turned to regard me with a smile, and she told me to take the keys and go home. Only once I was home could I remove the cage and masturbate. She wanted me to text her to ask permission to cum as well. Once that was done, and a photo of the aftermath was sent, I could also remove the plug.