I got a bit carried away with this little story, and it grew to be about twice the length that I originally intended for it to be. I didn’t want to edit it down, so I had to try to figure out a better way to present it. So, I tried a couple of options (I wanted to break it up into two frames, but I couldn’t find a suitable photo), and I ended up with a combination of two methods. I enlarged the caption box, but the font is still going to be pretty small. To get around that, I decided to just post the text separately. So, if you’re having trouble reading this one, just look at the bottom of this post to find the text.
“Oh, God!” I screamed, feeling every inch of him as his cock filled my ass. “Fuck! Fucking God! Yes!”
If I hadn’t been tangled in the throes of ecstasy, a small part of me might’ve been disgusted with myself, with what I had become. Those moments of clarity had become rare, but screaming with passion while being fucked with my treacherous roommate was definitely one of those infrequent intrusions into what had become my normal life where I might have seen things clearly.
Of course, there was a rational part of my brain that knew precisely what had happened, that could see how thoroughly I had been manipulated – by them, by fate – by something. It was imprisoned behind a wall of self-delusion, but it was there, all the same. Sometimes, I heard its cries. Its protests. Its pitiful wails of anguish and defeat. I had begun to think of it as my masculinity. The powerless man inside me. My old identity.
It had all begun simply enough – with a bet, and one I was sure I could win. No masturbation for a month. I thought it would be so easy. I had plenty of self-control, after all. I was convinced that I’d win without any sort of difficulty.
But then he moved his girlfriend in with us. I had met her a few times before, and, given the story he’d given – that she’d been kicked out of her parents’ place because they were controlling assholes – I was more than willing to help her out. I hardly even noticed that her move-in date coincided with the beginning of our bet. No – I didn’t make that connection until a week later when, unconcernedly, she started walking around the apartment completley naked. And she wore it extremely well.
I lasted maybe a few more days before, driven almost mad with lust by the naked, beautiful woman who was flaunting her nudity for all to see drove me to self-pleasure. I hated myself for giving in, but the desire was so strong that I managed to convince myself that I wouldn’t lose the bet unless my roommate found out. I knew he never would. I was safe. I would still win. I could have my cake and eat it, too.
Until he walked in on me as I furiously pleasured myself while staring at a photo I’d surreptitiously taken of his girlfriend. He was angry, of course. I would’ve been, too, in that same situation. He was deadset on kicking me out. Thankfully, his girlfriend intervened. She was the one to suggest the compromise: the chastity device.
Initially, I objected. I refused. I wasn’t going to clamp my pride and joy into some plastic prison. But they insisted that, if I was going to stay, I’d have to wear it. That was the only way she’d feel safe. I tried making other arrangements. I called friends. Family. I even tried to find another apartment. But my every effort was made in vain; it ended in failure. So, without any other option, I acquiesced to their ridiculous rule. But I knew, even as my roommates watched me fasten that thing around my manhood, I was making a mistake. Their twin smiles were proof of that.
Time passed, though, and eventually, I got used to the confinement, and, for a while, things were relatively normal. Until I got that itch.
I know this story makes me sound like some unrepentant sex fiend, but I assure you, that’s not what I am. I’m a normal guy with normal needs. It’s just that, for as long as I can remember, I’d cultivated a vigorous masturbation habit. It didn’t affect my life – not until that ridiculous bet – so I never considered it a problem. But with my cock locked up, and without the ability to pleasure myself, I was going crazy. I needed a release, and when it started to get out of hand, I started searching online for something – anything – that could placate that need.
I found prostate stimulation. I understand how that sounds. I get it. But you have to understand how desperate I was. It was driving me insane, that lack of sexual release. And I was desperate. So, with trembling fingers on my mouse, I ordered an appropriate toy online. For days, as I waited, I was a mess of anxiety, shame, and self-disgust. And when it finally arrived, my insides were knotted with the same. I tore open the package and quickly went into my room, which I locked behind me.
I won’t lie and say that that first time went well. It didn’t. Even with copious lube, it was agonizing. I felt like I was being ripped in two by the small toy. But such was my need that I couldn’t help but persist along that painful path to promised pleasure. And eventually, once my backside had acclimated itself to the penetration, I reached my goal.
Thankfully, I was alone because, as the orgasm ripped its way through me, I couldn’t help but scream out in a mixture of relief and ecstasy. Tiny droplets of semen dripped from my caged penis, but more than that, I experienced something far more powerful. It was life-changing in ways I never could have expected. Even as the aftershocks of that orgasm rumbled through my body, I wanted more. I wanted to experience it again. I spent most of that day with that toy up my ass, and in the days that followed, I couldn’t help but go back for more. I suppose it was only a matter of time before my habits were exposed to my roommates, but in that haze of ecstasy, I couldn’t bring myself to care. I certainly couldn’t stop. Not even after they caught me. Not even after my roommate’s girlfriend convinced me to give myself to her strap-on while he watched.
I admit that I got a little caught up in the moment. The act. I don’t know. It seemed like such a reasonable progression of my new obsession. They’d discovered my penchant for ass-play only a week before, and rather than shame me about it, they’d mostly just ignored it. However, the subject inevitably came up a week later when, after more than a few drinks, they asked if I’d be interested in helping them fulfill a fantasy. I asked what it was, hoping against hope that they’d finally release me from the plastic confines of my chastity device. They didn’t. But I was still excited when they suggested that I let her take me with a strap-on. By that point, I was well-used to the idea of anal penetration, and it had been such a source of pleasure that I hardly even thought about the implications. A toy was one thing. A fake cock attached to someone’s hips was something else entirely. But I didn’t care, especially as drunk as I was. I agreed without a second thought.
That step was as important to my eventual sexual servitude as any other, but I hardly even noticed, at the time. Even as she fucked me – and she knew precisely how to use that strap-on – I sank deeper into my dependence on anal penetration. So, when the next request came, I agreed eagerly. And soon, I was almost as much a part of their sex life as they were. It was almost wholesome, in a way. I felt like the third leg of their relationship; the simple aspect of close human companionship was almost as important as the sex.
I hardly even noticed when she started to guide me into femininity. The workouts. The diets. The grooming. Even when she started feeding me hormones, she couched it coded terms. She wanted a sexual partner with a bigger, more fuckable ass. And those pills would serve to bridge the gap that squats could never close. I was putty in her hands, and drunk on sex and simple belonging, I didn’t even think to question her. So, it wasn’t that long before I was presenting myself as a woman, if not always in public, then at least at home.
When they finally removed my cage, it was incredibly anitclimactic. I had barely even thought about the thing for months – I was getting plenty of sexual stimulation in other ways – but as soon as they suggested it, I was excited. That excitement faded when, after it came off, I tried to perform for my partners. First, it had shrunken into a pale shadow of its former self. The hormones, probably. Or the confinement of that tight cage. I don’t know. But on top of that, it remained limp, even when she sucked it.
That day, and for many subsequent days, I found myself weeping over what I’d lost. They tried to help. I wanted to let them. But the loss of my manhood was incredibly impactful to my sense of self. It shouldn’t have been, of course. I hadn’t used it in months and months, and I was more woman than many, by that point. But the human mind is a strange thing, and I couldn’t help but enslave myself to my irrational thoughts of loss.
But then, suddenly, the skies began to clear. My roommates – or rather, my partners, by that point – helped. They told me how beautiful I was. They complimented my progress. And in the end, when he finally begged to fuck me while she watched, they gave me exactly what I needed.
I could say that it was different than the toys, but that wouldn’t really give it credit. The fact was that it felt like I was finally waking up, that everything else had just been a ladder to my eventual destination. Certainly, there was a fair amount of shame there – I still thought of myself as a straight man or, if pushed, a lesbian woman – but I couldn’t even begin to deny my own feelings. I liked cock, and no amount of self-delusion could change that.
So it’s been for some time now. I think about how strange my road has been, about how different our relationship is. Most of my friends – and certainly, my family – doesn’t understand. But they don’t need to. So long as we have each other, that’s all that matters. Still, I can’t help but wonder if fate played a hand. After all, each step seemed so coordinated. Everything was like a piece of the puzzle falling into place. I don’t know. Maybe there is such a thing as fate. Destiny. Maybe I was always meant to tread this path. It doesn’t matter, though. I’m exactly where I’m supposed to be.
I hope you enjoyed it!
Oh, and before anyone (inevitably, as it’s already been posed before) asks me to do this for every caption, the answer is a polite no. For one, it creates more work for me (I type most of these captions into Photoshop so I can gauge the text size), and while it isn’t a LOT of extra work, I still don’t want to commit to that. But mostly, I don’t want to do that because I view each caption as a piece of art, albeit a smutty one. The text is meant to compliment the photo and vice versa. Breaking them up hurts my artistic sensibilities. And while I don’t take it as seriously as that might imply, there are a few things I just don’t want to compromise on. This is one of them.