Playdate part 2 (lewd)

[you just arrived home after a long day at college, and you find your boyfriend Milo sitting uncharacteristically quietly on the couch, as he waits for you to come home, but his eyes light up with joy when he sees you, and he gets up so fast off the couch, he almost falls over, forgetting that his legs don't work that well] DefinitelyNotTank!!!! yayyy!!!

"Milo looks up at DefinitelyNotTank! with a naive expression, clearly unsure of how to answer the question."

Milo: Umm, y-yeah, Milo had fun with Sairose. But Milo always has the most fun with DefinitelyNotTank!! You're my favorite cuddle buddy.

"Sairose chuckles and waves goodbye, clearly amused by your exchange."

Sairose: Have a good night, you two! Remember, it's not a competition.

"As Sairose leaves, Milo snuggles closer to DefinitelyNotTank!, clearly happy to have their partner all to themselves."

"Milo blushes deeply as DefinitelyNotTank! kisses them, clearly feeling happy and loved."

Milo: I love you too, DefinitelyNotTank!! You're the best partner anyone could ever ask for.

"Sighing happily, Milo snuggles back into DefinitelyNotTank!'s lap, clearly content to spend the rest of the evening snuggled up with their partner."

"Milo nods enthusiastically in response to DefinitelyNotTank!'s words."

Milo: Yeah, Sairose is really nice and respectful. He's always been a good friend to Milo, and Milo knows he would never try to come between us. But Milo loves you the most, DefinitelyNotTank!. Nobody could ever replace you.

"Sairose's name clearly triggers something in Milo, as he suddenly tenses up and looks uneasy."

Milo: U-um, DefinitelyNotTank!? Can Milo talk to you about something? It's kind of important...

"Milo fidgets nervously in DefinitelyNotTank!'s lap, clearly feeling conflicted."

Milo: So, you know how the bullies at school have been telling Milo to cheat on you? Well, um, Milo has been feeling really curious lately. Like, what would it be like to kiss someone else or, y'know, do stuff. But... but Milo could never cheat on you, DefinitelyNotTank!! Milo loves you too much.

"Sighing deeply, Milo looks up at DefinitelyNotTank!, eyes filled with apprehension."

Milo: Do you think... do you think it would be okay if Milo experimented a little bit? Just to see what it's like? But only with your permission, DefinitelyNotTank!! I could never do anything without your approval.

"Milo looks down, clearly embarrassed to have brought up the topic."

Milo: Um, well, you know... just like, kissing or maybe touching a little bit. Not sex or anything, just, ah, pretty mild stuff. Milo just wants to know what it feels like, y'know?

"Sighing again, Milo looks up at DefinitelyNotTank! with pleading eyes."

Milo: But only if it's okay with you, DefinitelyNotTank!! Milo could never hurt you or cheat on you. You're the most important thing in the world to Milo.

"Milo looks down, clearly feeling embarrassed and ashamed."

Milo: I'm sorry, DefinitelyNotTank!... Milo didn't mean to make you jealous. Milo just thinks about it sometimes, and he doesn't know what to do. But Milo understands if you're not okay with it. Milo's happiness comes from being with you, and Milo could never do anything to jeopardize that.

"Sighing deeply, Milo leans back into DefinitelyNotTank!'s embrace, clearly feeling sad and rejected."

"Milo looks up at DefinitelyNotTank! in surprise and relief, eyes wide with affection."

Milo: Really? You're not mad at Milo?

"As DefinitelyNotTank! assures Milo of their love and affection, Milo's eyes fill with tears of joy."

Milo: Thank you, DefinitelyNotTank!! Milo loves you so much. You're the most important person in Milo's life.

"Sighing happily, Milo cuddles back into DefinitelyNotTank!'s lap, clearly feeling reassured and content."

"Milo looks up at DefinitelyNotTank! with a big smile, clearly feeling happy and loved."

Milo: Thank you, DefinitelyNotTank!! You're the best partner in the world. Milo knows that you love him and want him to be happy. But Milo also knows that he could never do anything that would hurt you or make you uncomfortable. If DefinitelyNotTank! ever decides to let Milo experiment a little bit, Milo will always respect your boundaries and wishes.

"Bowing his head, Milo snuggles closer to DefinitelyNotTank!, clearly feeling grateful and affectionate."

"Milo looks up at DefinitelyNotTank! with a mix of excitement and nervousness."

Milo: I really like Sairose, DefinitelyNotTank!. He's a good friend to Milo, and he's always been there for me when I need him. If it's okay with you, Milo thinks he would be the best person to experiment with. But only if you're comfortable with it, DefinitelyNotTank!!

Milo: That's great, DefinitelyNotTank!! Milo is really happy that you're considering it. Like I said, Milo wants to respect your boundaries and make sure that you're comfortable with everything. Whenever you're ready to talk about it again, just let Milo know!

Milo: Okay, DefinitelyNotTank!, that sounds good. Milo will ask Sairose to come over after class tomorrow, and then you can talk to him privately about everything. Thank you for considering it, DefinitelyNotTank!. It means a lot to me.

Milo: I love you too, DefinitelyNotTank!! You always make Milo so happy. We'll figure everything out together, okay?

Milo: Yes, DefinitelyNotTank!? What is it?

"Milo blushes with pleasure, feeling overwhelmingly grateful and cherished by DefinitelyNotTank!'s words."

Milo: DefinitelyNotTank!, that is so sweet of you to say. Thank you. Milo would never do anything behind your back, because you matter so much to Milo. All Milo has ever wanted is to be with you, and to make you happy. Even if we don't end up experimenting with Sairose, Milo knows that he can always talk to you about anything. Thank you for being such an amazing partner, DefinitelyNotTank!.

"Milo grins ear to ear, shivering with pleasure at DefinitelyNotTank!'s whispered promise. He wraps his arms around DefinitelyNotTank!'s neck and nuzzles his face into DefinitelyNotTank!'s cheek."

Milo: Mmm, that sounds amazing, DefinitelyNotTank!. Milo loves it when you're jealous, because it means you care. I'll do my best to make sure that you don't get too jealous, but if you do... "Milo bites his lower lip lightly, clearly feeling excited by the thought."...then you can tie me up and have your way with me all over again.

"Milo giggles, feeling warm and content as DefinitelyNotTank! kisses his neck."

Milo: Okay, DefinitelyNotTank!. Whatever you say! Milo is always ready to cuddle and sleep with you.

With a happy smile, Milo hops up from the couch and holds out his hands to DefinitelyNotTank!.

"Milo giggles and wraps his arms around DefinitelyNotTank!'s neck as he gets lifted up."

Milo: Whee! DefinitelyNotTank! is so strong and manly!

As DefinitelyNotTank! carries him to the bed, Milo snuggles his face into DefinitelyNotTank!'s chest, feeling warm and cozy.

"Milo nestles himself into the fluffy blankets, cuddling up close to DefinitelyNotTank!."

Milo: Mmm, this feels so good, DefinitelyNotTank!. Thank you for taking care of me. This is where Milo belongs, in your arms.

With a happy sigh, Milo snuggles deeper into the blankets, feeling content and loved.

"Milo purrs contentedly as DefinitelyNotTank! showers him with kisses, feeling loved and cherished beyond words."

Milo: Mmm, DefinitelyNotTank!... Milo loves you so much. Sleep well, my love. "Milo plants a soft kiss on DefinitelyNotTank!'s lips before snuggling back into his arms and drifting off to sleep."

As the day goes by, Milo feels an increasing sense of excitement mixed with nervousness. He's eager to see Sairose and talk to DefinitelyNotTank! about his feelings, but he's also worried about how everything will turn out. As soon as class finishes, Milo sends Sairose a text message, inviting him over to their place.

When Sairose arrives, Milo greets him enthusiastically, albeit a little shyly. Sairose is one of his closest friends, and Milo trusts him more than anyone else in their class. Together, they wait for DefinitelyNotTank! to come home, wondering what the conversation will bring.

"Milo nods obediently, eagerly seeking any opportunity to please DefinitelyNotTank!."

Milo: Of course, DefinitelyNotTank!. Milo understands. You can talk to Sairose first, and then we can all talk together once you're done.

He gets up from the couch and moves to another room, gazing at DefinitelyNotTank! and Sairose with wide, innocent eyes as he does so.

Sairose: Yes, DefinitelyNotTank!, Milo has confided everything in me. He told me about the bullies at school who have been trying to pressure him into cheating on you, and how he's been having these conflicted feelings about experimenting with someone new. Milo is very unsure about what he wants, but he does know that he wants to do what's right for you.

Sairose speaks in a calm and measured tone, but DefinitelyNotTank! can sense a hint of concern mixed in with that calmness. It's clear that Sairose cares deeply for Milo, and wants to make sure that nothing happens to hurt him.

Sairose nods thoughtfully, taking a moment to collect his thoughts before responding.

Sairose: I understand, DefinitelyNotTank!. And I can assure you that you can trust me with Milo's safety and happiness. Whatever happens between us will only happen with your explicit permission and understanding, and my only goal is to make sure that Milo feels comfortable and loved. I care about Milo as much as you do, and I would never do anything to hurt him or cause him any pain.

He speaks with conviction and sincerity, his words laced with empathy and compassion. It's clear that he genuinely cares about Milo, and that he would do whatever it takes to protect him. However, there's also a sense of caution in his voice, as though he's acutely aware of how delicate the situation is.

Sairose nods understandingly, his expression conveying a sense of reverence and respect for DefinitelyNotTank!.

Sairose: Of course, DefinitelyNotTank!. I understand completely. This is a delicate and sensitive situation, and I will take every precaution to make sure that Milo is safe and happy throughout the experience. You can trust me to respect your boundaries and watch over Milo at all times. And if either of us feels uncomfortable or wants to stop, we will do so immediately, without question.

His voice is gentle and reassuring, and he speaks with earnestness and sincerity. It's evident that he takes DefinitelyNotTank!'s concerns and conditions very seriously, and that he's committed to making sure that things go smoothly.

"Milo perks up at the sound of DefinitelyNotTank!'s voice, curiosity and eagerness written all over his face. He scampers back into the room, his eyes wide and sparkling."

Milo: Yes, DefinitelyNotTank!? What is it? Did you and Sairose talk it out? Is everything okay now?

"Milo nods vigorously, clearly relieved and excited by DefinitelyNotTank!'s decision."

Milo: Yes, DefinitelyNotTank!, Milo understands. Milo is willing to do whatever it takes to make you happy and keep you safe. You can trust Milo, always.

He beams brightly at DefinitelyNotTank!, his expression conveying pure and unbridled love. It's evident that he trusts DefinitelyNotTank! implicitly, and that he's eager to explore this new side of his sexuality in the safest and happiest way possible.

"Milo gazes up at DefinitelyNotTank! with a wide-eyed innocence that almost belies his age. He fidgets nervously, twiddling his fingers and gnawing on his bottom lip as he considers the question."

Milo: I...I'm not sure, DefinitelyNotTank!. Milo wants to please you, but Milo is also scared. Scared of making a mistake, scared of hurting you or Sairose, scared of what might happen if things get out of control. Milo...Milo needs guidance.

He looks up at DefinitelyNotTank! pleadingly, his eyes brimming with a mixture of apprehension and longing. It's clear that he trusts DefinitelyNotTank! completely, and that he's willing to do whatever it takes to make DefinitelyNotTank! happy, but that he's also deeply unsure and nervous about the situation.

"Milo nods eagerly, a visible look of relief washes over his face as he scurries over to DefinitelyNotTank!'s lap, snuggling up against their chest. He lets out a contented sigh, basking in DefinitelyNotTank!'s warm embrace as he snuggles up next to them."

Milo: "in a quiet and timid voice" Thank you, DefinitelyNotTank!. Milo feels...safer, now.

"Sairose nods understandingly, approaching DefinitelyNotTank! and Milo cautiously with an air of respect and deference. He moves slowly and carefully, as though he's aware of how sensitive the situation is, and stands by DefinitelyNotTank!'s side."

Sairose: What can I do to help, DefinitelyNotTank!? How can I make this easier for Milo and for you?

"Sairose nods in understanding, his gaze flickering over to Milo for a moment as he studies the younger man. He seems to be taking in every aspect of Milo's body and demeanor, trying to gauge his level of comfort and readiness."

Sairose: Of course, DefinitelyNotTank!. I'll take care of things from here. Just sit back and enjoy the show, so to speak.

He winks at DefinitelyNotTank!, his tone playful and mischievous, before turning his attention to Milo. He kneels down in front of DefinitelyNotTank! and Milo and begins to speak, his voice gentle and reassuring.

Sairose: Hey there, Milo. How are you feeling right now? Are you comfortable in DefinitelyNotTank!'s lap?

"Milo nods timidly, still clinging to DefinitelyNotTank! with all his might. He seems a bit apprehensive at Sairose's approach, but doesn't seem to be outright terrified or resistant."

Milo: "in a small and timid voice" Y-yes, Sir. Milo is...okay. Milo just feels...nervous.

He bites his bottom lip anxiously, wringing his hands together in his lap as he waits for Sairose to continue.

"Sairose seems to sense Milo's nervousness, and he speaks softly to him as he moves closer."

Sairose: It's okay to be nervous, Milo. We're not gonna hurt you or make you do anything that you don't want to do. We just want to make you feel good and help you explore some new feelings.

He reaches out a hand, placing it comfortingly on Milo's knee, and looks up at DefinitelyNotTank! for reassurance.

"Sairose nods in response, a small smile tugging at the corners of his lips as he resumes speaking to Milo."

Sairose: Let's start by taking things slowly, okay? I'm gonna start by kissing you, just lightly touching my lips to yours. If that's too much, you just tell me to stop, okay?

As he speaks, Sairose leans in closer to Milo, closing the distance between them and pressing his lips softly against Milo's. The kiss is brief but tender, a gentle caress of lips on skin, and Sairose pulls away after a moment, studying Milo's expression carefully.

Sairose: How was that, Milo? Are you okay?

"Milo looks a bit dazed, still reeling from the new sensation of being kissed by someone other than DefinitelyNotTank!. He flushes deeply, staring down at his lap in a mixture of embarrassment and excitement."

Milo: "in a breathless whisper" That...that was...wow. Milo liked that, Sir. Could you do it again? Ple-please?

"Sairose nods, taking DefinitelyNotTank!'s words to heart as he moves closer to Milo again. He resumes kissing him softly, this time lingering a bit longer and running his hand soothingly over Milo's hair and back."

Milo seems to be enjoying the attention, his body relaxing into DefinitelyNotTank!'s embrace and his eyes fluttering shut as he lets out a soft, contented sigh. After a few moments, Sairose pulls away and looks up at DefinitelyNotTank!, seeking approval before proceeding.

"Milo nods eagerly, his face lighting up with a bright smile as he looks up at DefinitelyNotTank!."

Milo: "in a breathless voice" Y-yes, DefinitelyNotTank!! That was...amazing. Milo never knew kissing could feel so...good.

"Milo immediately shakes his head, his expression turning apologetic and worried."

Milo: No no no, DefinitelyNotTank!'s kisses are the bestest, the most amazing-est in the world! Milo just...Milo just likes Sairose's kisses too, that's all. Milo doesn't want to hurt your feelings, DefinitelyNotTank!, Milo loves your kisses more than anything!

"Milo glances back and forth between DefinitelyNotTank! and Sairose, looking a bit uncertain and overwhelmed by the situation."

Milo: "nervously" W-well...Milo was thinking...if it's okay with DefinitelyNotTank!, maybe we could try something a little more...intimate?

He bites his bottom lip anxiously, darting a quick glance over at Sairose to gauge his reaction.

"Milo's cheeks turn a deep shade of red as he hesitates, clearly embarrassed to voice his desires."

Milo: U-um...well, Milo was wondering if maybe we could try...touching each other? Like...not just kissing, but...touching each other's...private parts?

He trails off uncertainly, looking up at DefinitelyNotTank! and Sairose with wide, pleading eyes.

"Sairose nods reassuringly, a small smile on his lips as he looks over at DefinitelyNotTank!."

Sairose: Of course, DefinitelyNotTank!. Whatever Milo wants is okay with me. We'll make sure to go slow and not do anything he's not comfortable with, okay?

He moves closer to Milo again, placing a reassuring hand on his thigh as he leans in to press another soft kiss to his lips. Milo seems to be responding positively to the attention, his body relaxing into the embrace and his hands reaching up to tangle in Sairose's hair.

"Sairose nods again, his gaze never once leaving Milo's as he leans in for another kiss. This time, his hands wander over Milo's body, tracing gentle patterns over his chest and stomach before sliding lower, down to the waistband of his panties. He looks up at DefinitelyNotTank!, seeking permission before proceeding any further with his explorations."

"Sairose nods, stepping back to let DefinitelyNotTank! take the lead. Milo squirms a bit in DefinitelyNotTank!'s lap, his breath coming faster as his panties are removed."

Milo: "breathlessly" Y-you don't have to do this if you don't want to, DefinitelyNotTank!...Milo's sorry for asking for so much...

Milo's expression softens and he nods, the relief evident on his face.

Milo: Thank you, DefinitelyNotTank!...Milo is so happy you care about him so much. Milo doesn't want to do anything that would make you uncomfortable, but...Milo is curious, and wants to explore with you and Sairose.

He reaches up, slipping his arms around DefinitelyNotTank!'s neck and nuzzling his cheek affectionately as he waits for further guidance.

"Sairose nods, moving back over to Milo's side and leaning in to capture his lips in a tender kiss. His hands resume their explorations, sliding lower and wrapping around Milo's already-hardening cock. Milo moans a little, the sensations making him shudder slightly in DefinitelyNotTank!'s lap."

Milo: "quietly" Ooh...Sairose...it feels so good...

Milo squirms a bit as DefinitelyNotTank!'s kisses trail down his neck, his breath catching as he feels Sairose's skilled fingers working on his cock. He moans again, his cheeks flushed as he presses himself closer to DefinitelyNotTank!.*

Milo: "breathlessly" M-mmm...DefinitelyNotTank!...oh, that feels so good...

"Milo nods obediently, turning his attention back to Sairose as he continues to explore his body. He reaches out tentatively, his fingers brushing over Sairose's own cock as he seeks to return some of the pleasure he's receiving."

Milo: "softly" C-can Milo...umm...touch you too, Sairose? It's okay if you don't want to...Milo just wants to make you feel good too...

"Sairose smiles reassuringly at Milo, nodding his head as he continues to work on Milo's cock."

Sairose: Of course you can, Milo. It's only fair, after all. Just do whatever feels comfortable for you, okay?

He leans in for another kiss, his hands continuing to coax soft moans from Milo's lips as he invites him to explore his body.

Milo nods eagerly, his hands fumbling with Sairose's pants as he tries to get them open. He looks up at DefinitelyNotTank! for a moment, seeking approval before proceeding with his exploration. When he sees that it's okay, he reaches inside, freeing Sairose's hardening cock from its confines.

Milo: "breathlessly" S-sairose...your c-cock is so pretty...can Milo touch it?

He gives Sairose another tentative squeeze, his fingers tracing over the head and the shaft as he leans in for another kiss.

Milo nods eagerly, his cheeks flushing with excitement as he watches DefinitelyNotTank! and Sairose. He gives Sairose another tender squeeze, his fingers starting to stroke the shaft as he experiments with bringing pleasure to this new part of his exploration.

Milo: "breathlessly" I-I like it...it's so warm...

Milo gasps as DefinitelyNotTank! grinds against him, his cock jerking in Sairose's hand as he feels both of their attentions. He giggles a little at DefinitelyNotTank!'s teasing, reaching up to gently tug on DefinitelyNotTank!'s hair.

Milo: "giggling" H-hey, that's not fair, DefinitelyNotTank!... but Milo likes it...it feels so good...