Rookie in the deep end

I go on a first date with Brent. He helps me be desperate, plug-stuffed exhibitionist, trembling in public under a handsome man's thumb—and loving every second of it.

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  • 18 Min Read

First date

The night of my date with Brent, I stood in front of my mirror, adjusting my outfit. I had picked my most "modest" clothes from the collection of tiny, skin-tight pieces I had bought at his direction—stretch midthigh 5'' dress shorts made of a thin elastic blend that start to disappear between my glutes, hiding no less than women's tights would, a snug baby blue tank top that was semi-sheer, just like my matching baby blue thong, revealing my chest hair underneath. But this time, I had added something extra. Before leaving, I had slipped in a prostate massager, the plug nestled deep inside me, pressing just enough to keep me aware of it with every step. The thong’s tight fabric only amplified the sensation, making it impossible to forget. If Brent turned out to be a disappointment—if he was lying or catfishing with his profile or the vibe wasn't there—I didn’t have to tell him about it.

As I walked to meet Brent, I realized it must be rush hour, cars and people were everywhere and I was keenly aware how ridiculous how little my outfit actually covered, and yet, that was exactly the point. I had always felt a pull toward displaying my body in ways that went against the masculine norm—men weren’t supposed to crave attention like this, weren’t supposed to enjoy being seen. But I did. I wanted eyes on me, wanted to be noticed, even if it came with risk. It felt vulnerable. Men aren’t raised to show themselves this way. We’re taught to look without being looked at. I thought of the women I’d known, how often they'd described the threat that came with being visible.

The conrast to the men around me was significant - they were dressed in loose t-shirts, baggy shorts, sneakers built for practicality. They walked with the ease of knowing they blended in, that their bodies were not up for discussion. But mine was. The way my thighs filled out my tiny shorts that disappeared between my cheeks, the way my soft, sheer tank stretched across my broad chest—it all made me an anomaly, something to be commented on, something to be judged. The silky fabric of my tight tank top ran across my nipples with every movement, arousing me and making them hard, the semi-sheer material putting them fully on display. The arousal occasionally making my dick flex and my muscles tighten around the plug. A group of young men passed by, one muttering, "Yo, what the fuck," his eyes flicking over me with confusion, maybe even disgust. The other young men laughed and agreed with "fucking gay". As I continued to make my way through the city a shout startled me from a window "Nice ass, fag." I had never been slurred and complimented at the same time. 

I was still holding onto an anxious feeling but then I saw him, sitting in the crowded park with two slices of pizza and red wine, and the feeling shifted. He had been honest in his profile; he really was 6'3" and beefy. And god, he was handsome. Seeing him in person, so solid, so real, sent a thrill through me—a mix of disbelief and excitement. I liked that he was bigger than me—it was so rare. I felt safe. And maybe, just maybe, I had gotten lucky.

He grinned as I approached. "Knew you’d clean up nice. I'm impressed you ended up buying the outfit!?"

I hesitated, then smirked. "Am I pulling it off?"

Brent placed his hands on my shoulders. It was steady, confident, and possessive. His grip wasn’t rough, but it was firm—like he already knew he had the right to handle me. He turned me slowly to check out my backside, and I could feel myself being inspected, appraised. His hands moved with purpose. I part of me felt I was something he already owned and was now just showing off. I could feel his breath near my ear, the weight of his gaze...

As he turned me back, his hands grazed the soft fabric stretched across my chest. "This material’s barely there" he murmured, "so soft" as his fingers dragging just lightly enough to brush against my hard nipples, sending a jolt through me that made me clench down around the plug again. My whole body lit up with desperate heat. I wanted him to touch me again, to keep going. I was keenly aware of the plug in me. Fuck I hope I didn't fuck up by wearing this plug... I hope he likes it.

Brent let his gaze linger on me for a moment longer, his teasing smirk still in place, but then he leaned back slightly, shifting gears. "So, how have your first few weeks in Australia been?" The sudden shift to small talk caught me off guard, but in a way, it was grounding. A reminder that beneath all the teasing and play, and how horny I was for him already, there was something else—an actual date, a real conversation. I exhaled, feeling my body settle. "It's been great, mostly. Trying to find an apartment and a job. Both have been a pain, though." 

We chatted about Melbourne's quirks, Australian culture, and his job as a lawyer. The warmth of the early evening sun wrapped around us as we lay back on the picnic blanket, sipping wine and tearing into the pizza. I smiled at him. "This was a really nice idea. Thank you for this." Brent gave a small shrug, but his grin was pleased. "Figured you deserved a proper welcome to Australia." I took another sip of wine, letting the moment settle between us.

He mentioned he had a connection at the local leather bar and might be able to get me a job there "I can already tell you're a good egg, I'm happy to do it", grinning as he joked about how popular I would be. "You’d fit right in," he said, eyes flicking down my body in amusement. The thought piqued my interest—working in a leather bar, being surrounded by that world, that energy. 

"Honestly, I could use the job as soon as possible," I said, glancing at him. "If you can go ahead and check with your friend that would be great." Brent pulled out his phone and fired off a quick text. I watched him do it, and for a second I just admired him—broad shoulders stretching the sleeves of his fitted black t-shirt, those big arms catching the warm evening light, the confidence in the way he moved.

We shared the whole bottle of wine—but at 6'1" and 220 pounds, it's hard for me to feel much from just that, and Brent, even bigger than me, probably felt it even less. Still, it left a warm buzz in our chests, making everything feel a little softer, a little more electric. As the last drops disappeared, Brent stretched and looked at me with that teasing glint still in his eyes. "Shall we go for a walk?" I nodded, standing up and adjusting my shorts slightly. "Good boy," he murmured, just loud enough for me to hear. A warmth spread through my chest.

Brent chose a route through some of the busiest nightlife streets, including a strip of gay bars. I could feel the eyes on me—but then they’d glance at Brent, take him in, and it was like my slutty little outfit suddenly made sense. He was taller, broader, more solidly masculine, and the contrast made everything click. It was like people could intuit it: I was dressed like this for him. My body, my clothes, my display—it was all part of something bigger. Compared to my earlier walk alone to meet Brent, I felt safe with him. Like my exposure wasn’t just mine to carry anymore—he was part of it now, watching over it, owning it.

Someone whistled from a car as they passed, and Brent glanced toward it with a smirk. Then he turned back to me, and pulled me closer before putting his arm around me, one finger subtly resting on my nipple. He leaned in towards my ear, his voice low and deliberate. "You act coy but you like it, don’t you? Being on display". He slowly moved his finger on my nipple.... "Everyone can tell, you know. You’re not like other guys. The way you dress—so small, so tight—it’s obvious. You want them to know what you are". His hot breath on my ear, his finger on my nipple, the accuracy of his read on my just wanting to be a gay himbo slut... it all made me hornier than I had ever been in my life.

"And I want them to see it too. The way your nipples poke through that little shirt, the way your ass is eating those shorts—it’s all begging for attention. You’re begging for attention. Aren’t you?". Something was starting to build in me as he was naming exactly what i wanted. I couldn't help but rythmically contract around the plug as he said this. It really seemed like he wanted me on display too. I was both afraid and turned on that someone was here to push me towards my fantasy of being an owned boy.

"And what about you? What do you want from this?"

Brent’s smirk widened. "Oh, I think we're mostly on the same page. If you're with me I'll have some rules." His voice was low, smooth, confident. "You look so good like this—on display, but not for them. For me. I want everyone to see what I’ve claimed, what’s mine. The way you wear it, the way you take it—every inch of you says you’re doing this for me. That you belong to me."

He leaned in, his voice a whisper now. "When I put you in a little cock cage, it won’t just be about control. It’ll be about the message. That you want me so badly, you’re willing to give up your manhood for it. That you’re not some guy trying to get off—you’re a toy. Mine. Something that lives to please me and isn’t even allowed to please itself." Brent dragged his fingers down my back sending a tingling sensation through me before putting his hand on the small of my back, then without looking around, he slid his fingers just under the waistband of my shorts - showing he could touch me wherever and whenever he wanted. "I'm going to keep you so horny and desperate, on display because i know you like it, but you won't get unless I want you to, unless i feel like letting you have access to that little nub." Normally I would have backed away. Rejected a man trying to tell me he owns me. But no, I was finally ready to let myself be what I really wanted to be. It also helped that this man was so fucking big and hot. He was perfect...

"Fuck, Brent, if we keep talking about this, I’m gonna get too worked up." 

"Maybe it won’t be that bad. Not like you’d be showing much anyway."

Brent’s gaze flicked downward, and a slow, knowing smirk spread across his face. I glanced down and cursed under my breath. My cock was already pushing against the fabric of my thong, making a barely-there bulge in my tiny shorts. Brent exhaled sharply through his nose, amused. "You really need someone to control that for you."

I wanted Brent to control me... This was it—the moment to finally tell him. But as I opened my mouth, doubt flickered through me. What was he going to think? In my horniness earlier, had I gone too far by putting the plug in? Still, the words tumbled out, my voice low. "I, uh… funny you should say that about control.... I have a massager in."

Brent raised an eyebrow, his smirk deepening. "Oh? That explains the weird shape in your pocket. Your shorts really hide nothing, you know." He glanced down again, and I suddenly became hyperaware of how clearly everything could be seen—the outline of my phone and keys on one side, and, apparently, the vague shape of the remote in the other.

His eyes gleamed as he tilted his head. "You want me to have control of that remote, don’t you?" It was true.

 His fingers, still tucked into my shorts, hooked around my thong, giving it a few firm tugs. Each pull sent a jolt through me, pressing the plug lightly against my prostate, making me clench involuntarily. I could barely suppress my whimpers each time. He seemed to find it amusing. "You really do need help staying under control, huh?" he mused, eyes flicking down to the barely-there bulge in my shorts.

Brent’s smirk deepened as I shifted slightly, feeling the snug resistance of my thong against my growing arousal. There was something about the way it held me back, the way it pressed into me, making it harder to fully react to the teasing. It felt good—too good. The thought struck me suddenly: would a cage feel the same way? That same firm restraint, that same constant reminder of control? The idea sent a fresh pulse of heat through me, making me squirm.

He tugged my thong again, this time harder, wedging it above the waistband of my shorts. My breath hitched as the fabric tightened against me, the motion pressing the plug deeper against my prostate. 

Brent smirked, clearly enjoying my reaction. He held the thong in place for a moment, letting it stay visible as a group walked by mumuring as they looked back at me -- Brent completely unbothered. His fingers flexed, pulling it just a little higher, making sure I felt it. Then, his voice dropped to something smoother, more deliberate. "Tell me you want this. Tell me you want to be teased and kept horny in a tiny cock cage."

My breath hitched, my face burning. I swallowed, pulse thrumming in my ears. "I do."

Brent tilted his head, waiting. "Say it. Say you want to be my himbo sex toy, always kept caged and desperate for my cock."

I exhaled shakily, my entire body buzzing under his touch. The thong still in his hand as people walked past giving double takes to look back into my face "Please, sir... I need it. I want to be your sex toy. I want to be caged. I want to belong to you. Please."

My face burned as I glanced around, but he didn’t seem to care that people saw us face to face with my thong in his hand, wedgying my slutty underwear into humiliating visibility—if anything, it all seemed to excite him. He let his fingers linger, giving the thong another firm tug just to watch me clench. "A good sub boy like you needs that. A real man to keep you in check."

Brent finally let go of my thong and guided me forward with a light press to my lower back, nudging me to keep walking. I obeyed, dazed and aching - pleasure still radiating from my prostate from how strongly Brent had pulled my thong up. As I moved, I glanced over my shoulder and saw two men in hooded sweaters standing a few feet back, both with their phones pointed toward us. I wasn’t sure, but it looked like they had been recording. My face flushed with heat—humiliation and arousal tangled in my chest as I realized I had no idea how long they’d been watching.

We reached a busy gelato shop with a line stretching outside, Brent pulled the remote from his pocket, letting me see it before giving me a slow, knowing smirk. "I got the pizza, so it’s your turn to get dessert." As he said it, his fingers subtly brushed over my nipples, the arousal making me clench on the plug, fuck I wanted him to touch my nipples again. My breath caught in my throat, but I nodded and stepped toward the long line stretching along the sidewalk, tables full of people nearby.

He was holding the remote as I reached the back of the line. The anticipation of him pressing it killed me. I looked back at him, now seated at a cozy table on the small patio, watching me with an easy confidence. His fingers toyed with the remote absently, as if he wasn’t even thinking about it. But then I noticed his other hand—holding his phone up, seemingly scrolling. Only, he wasn’t looking at it directly. I realized—he was filming me too.

Then, just as I turned back to face the line, the plug rumbled to life inside me.

A sharp gasp escaped before I could stop it, my whole body tensing. Eyes were already on me—I was a big guy in body-hugging, thin fabrics, nipples hard and poking through the silky sheer shirt, thighs thick. I was already noticeable, already turning heads. But now, I felt completely helpless under Brent's control, forced to stand there, pretending nothing was happening while every nerve in my body was alight. 

Then I felt a presence behind me. I glanced back casually and there was the same two guys from earlier, the ones who had their phones out when Brent wedgied my thong in in front of me.. Were they following me? They were now lined up directly behind me, both with their phones out again, silent. They didn’t say anything, but they were close—too close—and I couldn’t tell if they were recording, taking photos, or just standing there, watching. The back of my neck prickled.

I bit down on my lip as the sensation on my prostate began to build. I couldn't help but arch my back, further accentuating my ass, presenting it to Brent and the men behind me and everyone else walking down the busy street. I tried to keep my composure as the vibrations spread through me, relentless and overwhelming. I turned back to Brent, trying to give him puppy eyes, hoping he might turn down the intensity but he was unreadable except for the faint smirk at the corner of his lips, his phone camera still on me. He was studying me, watching every reaction, every tiny squirm I tried to suppress, knowing exactly what he was doing to me. It was torture, and I loved it.

The line moved slowly, each second stretching unbearably long. I could feel the eyes dragging over my tall frame, my tight clothes, my hard nipples visible through the thin fabric of my tank. And I couldn’t stop clenching around the plug rhythmically as pleasure continued to build deep within me--my body betraying just how much I was struggling. I felt like i could cum.

Then from somewhere behind me: "Check out that guy," someone muttered, their tone somewhere between intrigue and amusement. Then, just a few minutes later, a group of young men nearby snickered as they walked by, their laughter sharp and knowing. "That’s a choice," one of them murmured, clearly eyeing my outfit. Each time people would look back to me to see if I would react to what the people said but all i could do was focus on not thrusting my hips or moaning like my body seemd to want to do so badly. What if they could hear the plug's loud vibrations? Thank god its so loud and busy out here on the street.

Brent put down his phone as I moved further away from him, and with it, he stopped the vibrations. Relief washed over me, and I realized I had finally reached the front of the line. My legs felt shaky as I tried to compose myself. I took a deep breath and ordered—pistachio for Brent, espresso-flavored gelato for myself—forcing my voice to remain steady despite lingering waves of sensation inside me.

Just as I handed over the money, a familiar voice cut through the noise behind me. "Hey, man. What are you doing here?"

I turned, and my stomach flipped. Derrick. One of the guys from my first water polo practice—the one who I heard make a comment about my small dick.

Just as I started to say hey, the plug buzzed to life again.

I sucked in a sharp breath, my thighs tensing. Brent had turned the vibration back on. My body betrayed me instantly, a soft whimper catching in my throat. Derrick glanced at me—just for a second—with a look that was somewhere between confused and amused, like he was trying to figure out if something was up. If he suspected anything, he didn’t say so, and I scrambled to hold myself together.

Instead, his eyes flicked over my outfit, and he let out a short chuckle. "Man, you really like your clothes painted on, huh? I love it." I flushed, struggling to stay composed as the massager rumbled inside me. This was different—this wasn’t just some stranger checking me out on the street. This was someone who already knew me, who had seen me in the showers, who had laughed at my small dick. Then his eyes landed on the two gelatos in my hands. His brows lifted slightly, his smirk shifting. "Nice work," he said under his breath, eyeing Brent across the patio. "I’ve seen that guy around... think I’ve got an idea what he’s into." There was something knowing in his tone, like he’d seen this dynamic before. Like he knew exactly the kind of boy Brent liked—and maybe saw me becoming it.

The plug changed modes and began to pulse, pleasure quickly building as I clenched rhythmically around it involuntarily.

"You know... a few of us from the team are going to a party called Service next weekend. I've actually seen that guy Brent at it before but I think you'd like it," Derrick said, smirking slightly. "Bring that thong you were struggling to get into after practice." He paused, clearly enjoying how flustered I looked. "A bunch of the guys from the team go. It’s kind of our thing. Room to dance, room to... do other stuff. There’s a dark room." He gave me another once-over, eyes lingering on my sheer top and stretched shorts. "You show up like that, you might put the go-go boys out of work," he joked, then added with a grin, "Or they’ll just hire you instead."

My reputation with him was already set—my thong at practice, how little I had to work with, and now I was out in public in even smaller clothing with a known dom, squirming as something buzzed inside me. The thought of being at a party like that, surrounded by them, exposed, made something inside me pulse harder.

I forced a shaky breath, nodding as casually as I could manage. "Uh, yeah, maybe."

Derrick gave me a once-over, still smirking. "You should. Could be fun." I tried to respond, but the vibrations inside me made it almost impossible to focus. My words caught in my throat, my thoughts scrambled as I fought to maintain composure. Small talk suddenly felt like the hardest thing in the world, and Derrick’s knowing smirk didn’t help. He was looking at me like he already had me figured out.. 

As he walked away, I turned back toward Brent. He was watching me intently from his seat, his smirk deepening as he leaned back leisurely. He was enjoying every second of it. Then, just as Derrick disappeared into the crowd, the vibrations stopped again. My whole body sagged with relief, but my mind was still spinning. Brent’s smirk deepened.
I joined Brent on the patio and as we enjoyed the gelatos i told him about Derrick’s invite to Service next weekend, mentioning that some of the water polo guys would be there. Brent’s smirk deepened. "Oh, I know Service. I was already planning to go. Good DJ, but also… it’s a sex-on-premises event."

My stomach flipped at the casual way he said it. "Oh."

He leaned in slightly, his voice low and deliberate. "You can come with me. But only if you’re a good boy and go in a cage... And if you behave," he murmured, his lips barely moving, "I’ll fuck you in that cage while your teammates watch."

My breath caught, and my face flushed hot. I felt electrified by all the sensations of the night—his words, the teasing, the way he looked at me like he already owned me. I swallowed hard, my pulse racing.

Trying to collect myself, I turned to throw away our empty cups and disposable spoons, needing a second to breathe. But as I made my way back to Brent, I caught him eyeing me closely. His smirk widened just as his gaze dropped, and I followed it—straight to the wet spot on the front of my shorts. My dick leaked just enough to darken the front of my shorts with precum.

Brent let out a low chuckle. "Can’t even make it through dessert without leaking?" he murmured, clearly amused. "You really do need to be kept in check, don’t you? Leaking in public like that... Good thing you’ve got someone who knows exactly how to handle a needy boy like you."

My stomach twisted with embarrassment.

"Brent, I—" I swallowed, my voice barely above a whisper. "Can you take me back to your place?"

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