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Bob and Y/n had been involved for a little over 6 months now, it had started slowly, Y/n being a gentleman to Bob taking him out places and just letting Bob get away from the tower. Then it turned into coffee and bookstore dates, taking Bob to concerts of small bands he had taken an interest in.
He sat on the worn leather couch in Y/N’s apartment, his long legs stretched out in front of him, one hand loosely holding a mug of coffee while the other rested on the back of the couch. The place smelled faintly of something nostalgic that Bob just couldn't put his finger on. It was cozy, a little mismatched with furniture that Y/N had clearly picked up over time, but it felt warm. It felt like home.
He glanced over at Y/N, who was sitting cross-legged on the floor, sorting through a small stack of vinyl records he’d picked up at a thrift shop earlier in the week. Y/N’s face was relaxed, a soft smile tugging at the corners of his mouth as he muttered to himself about which record to put on first. Bob couldn’t help but stare, his chest tightening as it often did when he let himself think too hard.
Six months. It had been six months since Y/N had started pulling him out of the suffocating walls of the Watchtower and showing him there was more to life than quiet self-loathing and endless isolation.
It had started small. Coffee dates, wandering through bookstores, late-night drives to nowhere in particular. Then it had turned into concerts, thrift shopping, and lazy afternoons spent in Y/N’s apartment like this.
“Hey,” Y/N’s voice broke through Bob’s thoughts, pulling him back to the present. Y/N was looking at him now, a record in one hand and a curious expression on his face. “You okay? You’ve been quiet for a little now, just wanted to make sure your not voiding.”
Bob cleared his throat, sitting up a little straighter with a quick little laugh. “Yeah,” he said, his voice a little too quick, and defensive. “I’m fine.”
Y/N raised an eyebrow, clearly unconvinced, but he didn’t push. Instead, he stood and crossed the room to the record player, carefully setting the vinyl in place. The music began to fill the room, and Y/N turned back to Bob, leaning against the edge of the table with his arms crossed.
“You sure?” he asked, his tone gentle. “You’ve been... distant. Did I do something?”
Bob’s eyes widened, and he shook his head quickly. “No, no, it’s not you,” he said, his voice earnest. “You’ve been great. It’s me. I just... I’ve been thinking about something, and I don’t know how to—” He cut himself off, running a hand through his hair in frustration.
Y/N tilted his head, his expression softening. “Hey,” he said, pushing off the table and moving to sit beside Bob on the couch. “Whatever it is, you can tell me. No judgment, okay?”
Bob hesitated, his fingers tightening around the mug in his hands. He wasn’t sure why this felt so hard to say. Y/N had never made him feel anything but safe, but this... this was different.
“I...” Bob started, his voice low. “I’ve been thinking about trying something. Something... new.”
Y/N’s eyebrows lifted slightly, but he didn’t interrupt, waiting patiently for Bob to continue.
“I mean, you know, in bed,” Bob added quickly, his face flushing as he glanced down at his lap. “It’s not that I don’t like what we’ve been doing—I do. I just... I know you're trans and I don't want to push and make you feel like I only want sex because I know how shitty it is when guys are only interested in that.” Bob starts to ramble worried he was making it worse. He kept his eyes down, unsure if he could handle seeing Y/N’s reaction.
“Bobby, Bobby hey it's Okay,” Y/N said simply.
Bob blinked, finally looking up. “Okay?” he repeated, his voice uncertain.
“Yeah,” Y/N said with a small smile. “Okay. If that’s what you want, I’m happy to try it. We can take things slow, make sure you’re comfortable. No pressure.”
Bob stared at him, a mix of relief and disbelief washing over him. “You’re... really okay with it?”
“Of course I am,” Y/N said, reaching out to rest a hand on Bob’s knee. “I mean, I have a prosthetic for a reason, handsome. I’ve just never used it with you because you seemed happy with just romantic commitment and I know you have trauma so I didn't want to push. But if you want to try it, I’m more than happy to oblige.”
Bob let out a shaky breath, some of the tension easing from his shoulders. “Thank you,” he said softly, his voice barely above a whisper.
Y/N’s smile gives the dirty blonde’s knee a gentle squeeze. “No need to thank me,” he said. Y/N leaned in, pressing a soft kiss to Bob’s forehead before pulling back. “Alright,” he said, his tone light and teasing. “Let me grab a few things, and we’ll figure this out together. Sound good?”
Bob’s cheeks flushed, but he nodded, he shifted slightly on the couch, his hands clasped loosely in his lap as he sat there waiting for Y/n to come back.
“Okay, before anything,” Y/N began, his tone calm but firm, his body angled slightly toward Bob, “I have a few questions.”
Bob nodded, giving him his full attention. “Sure, yeah. Ask away.”
Y/N tilted his head slightly, studying Bob carefully. “First off, have you ever had anal before? Like, I mean... is this brand new territory for you?”
Bob’s face flushed slightly, and he let out a soft, awkward chuckle as he leaned back against the couch. “No, it’s not new,” he admitted, rubbing the back of his neck. “I’ve, uh... done it before. A while ago. Back when I was... you know.” He trailed off, his gaze flicking away briefly.
Y/N nodded, He knew about Bob’s past and wasn't going to push for other details that Bobby wasn't ready to share.
“Okay,” Y/N said softly, his voice steady and reassuring. “Good to know. That makes things a little easier since you’re not completely new to it. But I’m guessing it’s been a while?”
Bob nodded. “Yeah. It’s been... years, honestly,” he admitted, his voice quiet but steady. “And back then, it wasn’t exactly... comfortable. It wasn’t about me, you know? It was just something I did to survive.”
“I get that,” he said gently. “But that’s not what this is. This is about you and me, pretty boy. About what you want and what feels good for you.”
Bob looked down at Y/N’s hand on his knee, “I know,” he said, his voice barely above a whisper. “That’s why I asked. Because I trust you.”
“Alright,” he said, his tone shifting slightly as he got back to business. “Second thing, I have a prosthetic, it isn’t a strap-on. It’s, uh... a little more complicated than that.”
Bob raised an eyebrow, his curiosity piqued. “Complicated how?”
Y/N leaned back, gesturing as he spoke. “It’s a custom-made piece,” he explained. “I haven’t ever used it on anyone before. You know how I have packers and stuff, right? Well, it’s kind of like that, but... not. It’s designed to be anchored inside of me, so it stays in place while I’m, you know, using it.”
Bob blinked, his interest clearly growing. “Anchored?” he asked, tilting his head slightly. “Like... inside you?”
“Exactly,” Y/N said with a nod. “It’s called a GenderMender. It’s a prosthetic that has an internal part that stimulates me while I’m fucking. It's mutually enjoyable. It’s not just about me giving, you’d be getting me off at the same time.”
Bob’s face flushed slightly at the bluntness of Y/N’s explanation, but he couldn’t deny how intriguing it all sounded. “That’s... really cool,” he said, his voice quiet but genuine. “I didn’t even know something like that existed.”
Y/N grinned. “Yeah, it’s pretty neat,” he said. “It’s custom-made, so it’s a good fit for me. But like I said, I haven’t used it on anyone before. So if we’re doing this, I’ll need to walk you through the steps, make sure we’re both comfortable with everything.”
Bob nodded, leaning forward slightly. “I’d like that,” he said. “I mean, if I’m being honest, I’m a little nervous. But I want to try. I trust you.”
Y/N’s smile softened, and he reached out to touch Bob’s hand. “I appreciate that,” he said. “And I promise I’ll take care of you. We’ll go slow, and if at any point you want to stop, just say the word, okay?”
“Okay,” Bob said, his voice steady.
“Good,” Y/N said, he leans down into a box which he has sitting on the coffee table and pulls out an item, holding the prosthetic in his hands, the soft silicone material catching the light. He sat back down beside Bob, carefully laying the piece on the coffee table in front of them.
“Alright,” Y/N said, his tone calm and patient. “this is it.”
Bob leaned forward, his curiosity outweighing his nerves, his blue eyes wide with surprise as he stared at it. He’d seen dildos before, hell, he’d even used a few. But this? This was different. It looked so real, from the shape and veins to the color. It was almost uncanny.
He blinked, his lips parting as he struggled to put his thoughts into words. “Wow,” he finally said, his voice quiet. “That’s... I mean, it’s so realistic.”
Y/N chuckled softly, leaning back against the couch as he watched the emotions flicker across Bob’s face, surprise, curiosity, maybe even a little jealousy. “Different than what you expected, huh?” he asked, his tone light and teasing.
“Yeah,” Bob admitted, his gaze still fixed on the prosthetic. “I mean, I knew you had... options, being trans and all. But I didn’t think it would look this real.”
Y/N grinned, clearly amused. “That’s the beauty of ‘build a dick’ ” he chuckles at the joke. “I got to pick everything: size, shape, length, color. It’s custom-made to feel right for me.”
Bob nodded slowly, his mind racing as he processed everything. He couldn’t deny the small pang of jealousy that bubbled up in his chest. Y/N had the opportunity to create something that worked perfectly for him, something that felt like it belonged. Meanwhile, Bob had spent most of his life feeling like his body was a stranger to him, something he used, something he abused.
“You okay?” Y/N asked softly, his voice pulling Bob out of his thoughts.
Bob blinked, glancing over at Y/N before offering a small, sheepish smile. “Yeah, sorry,” he said, running a hand through his hair. “I’m just... processing, I guess. This is all new to me.”
“I get it,” Y/N said, his voice warm and understanding. “It’s a lot to take in.”
Bob let out a soft laugh, leaning back against the couch. “That’s an understatement,” he said. “I think I’m just... surprised. I’ve learned so much about you, and about being trans these past few months, but I guess I didn’t realize just how... versatile things could be. It’s kind of amazing, honestly.”
Y/N smiled at that, a soft warmth spreading through his chest. “You just didn't expect me to have one that big huh?,” he teases. Which earns an elbow to the ribs from Bob. “ There's trial and error, but once you find what works for you? It’s pretty great. But I'm not going to make you try and take that first time”
Bob nodded, his gaze drifting back to the prosthetic. He hesitated for a moment before glancing back at Y/N. “So... it doesn’t make you uncomfortable? Using it, I mean?”
Y/N shook his head. “Not at all,” he said. “If anything, it makes me feel more me. It’s an extension of who I am, and I wouldn’t use it with just anyone. But you will need a bit of prep for it, and I don't want to overwhelm you or make you think you have to take it.”
Bob’s chest tightened at the words, a small rush of warmth spreading through him. He’d spent so much of his life feeling like he didn’t deserve trust, didn’t deserve kindness. But Y/N had always been patient with him, always made him feel like he was worth something.
Bob sat cross-legged on the floor of Y/N's bedroom, the warm glow of a bedside lamp casting soft light over the small collection of items Y/N had placed in front of him. The prosthetic from earlier rested in its spot, but now there were a few other things added to the mix—different packers, a harness, and a couple of smaller dildos in varying shapes and sizes, vibrators and even cock rings. Bob was quiet, his hands resting in his lap as he studied everything with a mix of curiosity and awe.
“This is... a lot more than I expected,” Bob said finally, glancing up at Y/N, who was laying on the bed, chin resting on his palm as he kicked his legs with a smile on his face watching Bob look through his collection. “I also have fluffy handcuffs and some other stuff for like Kink play too but I don't really keep a lot of that in there” he explains while chewing on some pretzels.
“You pick things up over time, figure out what works and what doesn’t. Some of this stuff I don’t even use anymore, but it’s still good to have options.”
Bob reached out hesitantly, his fingers brushing over one of the smaller dildos. “And this one?” he asked, lifting it slightly. “What’s it for?”
“That’s for beginners,” Y/N explained with a shrug. “If you’re new to penetration or just want something small, that’s a good place to start. It’s not really my thing, but some people like it.”
Bob nodded thoughtfully, turning the item over in his hands before setting it back down. “It’s kind of fascinating,” he admitted.
“I’ve had my fair share of bad experiences. Hell, I’ve had to learn the hard way that not everyone deserves access to my body.” Y/n hums like it's no big deal.
Bob looked up at him, his brow furrowing slightly. “What do you mean?” he asked,
Y/N sighed, running a hand through his hair as he leaned forward slightly, “I don’t bottom,” he said simply. “At least, not anymore. I had too many bad experiences with guys who saw me as... I don’t know, just a hole, or wanted ‘boypussy’ Like that was all I was good for. They didn’t care about me or my boundaries. they just wanted someone to use.”
Bob’s stomach twisted at the thought, a pang of anger flaring in his chest at the idea of anyone treating Y/N like that. “I’m sorry,” he said softly, his voice heavy with sincerity.
Y/N smiled faintly, shrugging one shoulder. “It’s not your fault,” he said. “It’s just... one of those things, you know? Being trans, especially before I started figuring out what worked for me, made me feel... vulnerable. Exposed. And some guys took advantage of that.”
“ But now, I won't bottom unless I’m the one in control. If I’m gonna let someone have a go, they’re tied up. Period. That way, I’m the one calling the shots. It’s the only way I feel safe, and it's only Anal, I don't like shit in the other hole outside of my prosthetic.”
Bob nodded slowly, “That makes sense,” he said. “And, I mean, it’s smart. You’re protecting yourself.”
“Exactly,” Y/N said, his tone firm. “I don’t have anything against bottoming in general, I just know it’s not for me. And that’s okay. I’ve figured out what I like, what I’m comfortable with, and I stick to that.”
“Yeah,” Bob said, his voice earnest. “I mean it. You’ve taught me a lot these past few months, probably more tonight than I was expecting. And I’m grateful for that.”
For a moment, they sat there in comfortable silence. “Alright,” Y/N said, his tone calm but intentional. “Let’s talk about you for a second.”
Bob tilted his head, his eyebrows lifting slightly. “Me?”
“Yeah, you,” Y/N said with a small grin. “If we’re gonna try this, I need to know what you’re into, what you’re not into, and where the hard lines are,” he added, his voice softening, “if any of this feels too personal or uncomfortable, just say so. No pressure, okay?”
Bob nodded slowly, his shoulders relaxing as he exhaled. “Okay,” he said. “Where do we start?”
“Well,” Y/N said, shifting so he was sitting cross-legged on the bed, “let’s start with experience. You said you’ve done anal before, but... what’s your comfort level with it? Like, did you enjoy it, or was it something you were just doing to get through the moment?”
Bob hesitated, his fingers brushing absently against his jeans as he thought. “It was... complicated,” he admitted. “Back then, it wasn’t really about me. It was about survival. I did what I had to do to get what I needed, drugs, mostly. Sometimes it was anal, sometimes it was blow jobs, sometimes it was... other stuff.” He paused, glancing down at his hands. “I didn’t hate it, but it wasn’t exactly enjoyable, either. It felt... transactional, I guess.”
Y/N nodded, his expression soft and understanding. “That makes sense,” he said. “And I get why that might make trying it again feel... complicated. So if you want to try, we’ll take it slow, and if it doesn’t feel good, we stop. No questions asked.”
Bob looked up at him, his chest tightening at the sincerity in Y/N’s voice. “Thanks,” he said softly. “That means a lot.”
“Of course,” Y/N said with a small smile. “Now, what about things you know you don’t like? Any big no-nos I should know about?”
Bob thought for a moment, his brow furrowing slightly. “I guess... I’m not into anything too rough,” he said. “Like, I’m okay with a little... I don’t know, intensity? But no hitting, no choking, nothing that feels violent. I’ve had enough of that in my life.”
Y/N nodded, his smile fading slightly as he processed Bob’s words. “Got it,” he said softly. “No rough stuff. Anything else?”
“Uh... I’m not really into dirty talk,” Bob admitted, his cheeks flushing slightly. “I mean, I don’t mind some, but if it gets too... degrading, it just pulls me out of it.”
“Fair enough,” Y/N said, making a mental note. “And what about stuff you do like? What gets you going?”
Bob’s blush deepened, and he let out a nervous chuckle. “You’re really putting me on the spot here.”
Y/N grinned, leaning forward slightly. “Hey, no judgment,” he said. “This is a safe space, Bobby. I promise. Just tell me what you like.”
Bob hesitated for a moment before speaking. “I guess... I like being taken care of,” he said slowly, his voice almost shy. “Like, when someone’s really focused on me, making sure I’m comfortable, making sure I’m enjoying myself. I like feeling... important, I guess.”
Y/N’s smile softened, and he reached out to rest a hand on Bob’s knee. “That’s not weird,” he said. “That’s actually really sweet. And honestly, it makes things easier for me, because I might get to turn you into my pillow Prince. I want to make you feel good, Bobby. That’s the whole point.”
Bob smiled faintly, his shoulders relaxing a little more. “Thanks,” he said. “I guess... I also like touch. Like, slow, gentle stuff. Hands on my skin, kisses, that kind of thing. It makes me feel... grounded.”
Y/N nodded, his thumb brushing absently against Bob’s knee. “Got it,” he said. “So, no rough stuff, no degrading talk, and lots of aftercare and touch. I can work with that.”
Bob chuckled softly, his gaze flicking up to meet Y/N’s. “You make it sound so simple.”
“It is simple,” Y/N said with a grin. “Communication makes everything easier. And now that I know what you like and what you don’t, I can make sure this is a good experience for you.”
Bob nodded, his chest tightening with gratitude. “You’re really good at this,” he said softly. “At making me feel... safe.”
Y/N’s smile widened, and he gave Bob’s knee a reassuring squeeze before leaning back. “That’s the goal,” he said. “Now, if you’ve got any questions for me, fire away.”
Bob hesitated for a moment before speaking. “Do you... enjoy this?” he asked, his voice careful. “Like, topping? I know you said you don’t like bottoming, but... do you actually enjoy being the one in control?”
Y/N’s smile softened, and he nodded. “Yeah, I do,” he said. “I mean, it’s not just about control for me, I may have a thing for watching others fall apart under me. I like knowing that I’m making my partner feel good, that they trust me enough to let go. That’s the best part for me. It’s not about power or dominance.”
“Unfortunately I don't think we will be doing anything tonight handsome, I'm tired as hell, and honestly I think cuddling and watching tv sounds like a really good idea” he coos which earns a laugh from Bob.
Bob looked up at him, his chest tightening at the sincerity in Y/N’s voice. “Yeah? Tv and cuddles huh?, trying to butter me up for something N/n?” he teases back.
“Don't tempt me pretty boy, I happen to really enjoy giving blow jobs and I will make you sob” he teases right back.