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First time being your pretty boy

14:47
Summary: Your boyfriend (the speaker) offhandedly mentioned wanting to try crossdressing, not really expecting it to go anywhere. But with a heaping helping of encouragement from you, he's finally dolled up in a maid outfit and looks damn fine in it to boot. You can't help but want to smooch him all over until the both of you are covered in lipstick (and he's fit to burst out of the panties he's wearing!)
14:47
Summary: You (the listener) are sitting in your room when I (the speaker) come and say hi. I'm one of your sister's friends, and I'm just waiting for others to arrive so we can go party. We've talked a little in passing, but we don't really know each other, so I sit with you and we chat for a bit. There's something between us though, and before too long we're making out on your bed. You want to go even further, but you're nervous as you're still a virgin. I promise to be gentle with you. I want you to feel good. You deserve to feel good.
20:29
Summary: Things have been tough going since your mother left your father a while ago. He tried to pretend everything was fine, but he was clearly struggling to keep life smooth for the both of you. One night before bed, he comes in to your room to talk to you. He's very drunk, and admits he can't keep doing everything by himself anymore. You've always been prepared to help him with anything he needs, like doing all the chores he doesn't have the time for. You tell him you'll take your mother's place for it all, and that he shouldn't worry. He thanks you, and tells you what a good son you are. However, it seems he had a little bit more in mind than chores when it comes to you filling the void your mother left. He wants something you aren't really comfortable with giving. Just be a good boy and let Daddy do this, okay? No crying, no tears, no struggling. Daddy needs this.
09:53
5(2)
Summary: I (the speaker) have always been a huge bully to you (the listener). Even though it's been many years since we finished high school together, I continue to use juvenile tactics to get under your skin. I say and do crude things to your mother. I constantly interfere with your love life and friendships. I make you do humiliating things just because I can. But there's always been something beneath it all that neither of us wanted to acknowledge. Tonight the tension between us bubbles over, and I do what we have both waited so very long for.
11:40
5(1)
"I've gotta get up for work, baby. No, I can't stay here all day and play with you. I think you're overestimating your strength if you think you'll keep me here, hun. Oh yeah? Then try keep me here. Hmm, almost got one of my arms pinned I guess. Nearly. Almost there. Oop, over we go. Aw, too bad. You tried with all your might to pin me down and instead you got yourself pinned under me. Better luck next time. You know... now that I've got you like this, I think I'm gonna have some fun with you. And no matter how hard you struggle, you can't stop me."
19:17
Summary: We've been discussing having a baby together for months now. It's something you've been especially vocal about, and I've been fully supportive of the idea. So why do you keep backing out whenever we're ready to try for a baby? You're too afraid to commit, and as your boyfriend it's my responsibility to help you make the right choices in life. So I'm not going to give you the choice at all. I love you, and I hate to trick you like this, but it's for your own good. You *will* get pregnant tonight.
12:13
Summary: All the guys hate him. He goes around flirting with all the ladies, even when he knows they're taken. *Especially* when he knows they're taken. He has a knack for seducing women and pissing off their boyfriends, and he takes great pride in the fact he's ruined so many relationships. He saunters around like the king of the world, doing whatever he wants with little consequence. But today, he went a step too far. He fucked *your* girl. Now you're going to give him a harsh reminder that he isn't the untouchable badass that he thinks he is.
13:54
5(1)
Summary: You (the listener) come to find me (the speaker) in the middle of the day. I've been distant all morning and you can tell something is up, despite my assertions that I'm fine. After some bold words from you I accept that maybe it's okay to let myself be vulnerable around others. If there's anyone I can be honest with, it's you. So, that all said... I'm feeling unusually angry this morning bitch boy. Are you gonna help me relieve some stress? Good boy.
14:55
Summary: I want you to be rough, baby. When I tell you to hold my head down on your cock, hold me down with all your strength until I choke. When I say fuck me hard and fast, fuck me as hard as you can. Bring tears to my eyes, I can take it. I'm in charge. If I need you to stop, I'll tell you to stop. Listen to what I say, be a good boy, and be rough with me.
14:02
Summary: You (the listener) are visiting your father (the speaker) for some time. One night you come out and sit with him on the couch to watch some boring TV show neither of you really cares about. You ask him if you can sit on his lap while watching; just for old time's sake, of course. You don't have any... ulterior motives. You're a good boy, after all.
17:19
Summary: As you (the listener) drift off into a sleeping pill induced sleep, your father (the speaker) comes in to check on you to make sure you're getting a good rest. Except, he may not have the most chaste of reasons for coming to check on you. Why else would he be naked? Or remove your blanket? Or take off your clothes? And isn't it a little strange that it was him who got the doctor to prescribe you those sleeping pills in the first place? Don't think too hard about it, princess. Just sleep, and let Daddy make you his perfect woman...
12:20
"Hey, I know I’m funny, but try not to laugh, alright? Here, drink up. Sorry for making you cough. I know your throat feels like shit right now. Not a very good caretaker, am I? It just sucks you aren’t dating anyone. You could’ve had, like, an incredibly sexy nurse taking care of you, just tending to your every need. But you got stuck with me, though I don’t think it’ll be such a downside... Not being weird dude, just uhhh… those moans you’re letting out, it makes me feel bad for you, you know! Just close your eyes and rest for me... I’m just gonna start with your shoulders, and gently rub them… Move a little lower… Just making you feel as relaxed as possible… Shhhhhhhh, it’s okay… Don’t worry… Shhhhh, it’s just lotion, it’s okay. Don’t worry. You’re gonna be more than just fine... Where do you think you’re going? No, no, don’t do that now. We both know I’m stronger than you. And we both know you want this."
11:17
"Sorry buddy, didn't mean to bump into you. Who are you, son? Oh. A new recruit for the cheer team, huh? Very nice. Tell you what, bud. Come with me to the storage shed just next door, and I'll get your uniform. Here you go champ, fresh uniform just for you. Chuck it on, see how it fits. Oh, were you not told? All the guys have to wear girl's uniforms. Budget cuts and all that. Put it on. There's a good lad. Listen to what I tell ya. Now, you should do some stretches. Just to make sure it fits right. Oh don't worry about this rope. Just bend over..."
15:43
Summary: Your roommate is sick and tired of hearing you complain about not getting any, how girls never pay attention to you. Hoping to shut you up, they decide to fuck you. You discover that you're far more bisexual than you realize, and your roommate discovers having a desperately horny guy pound their ass is actually really fucking hot. Script by u/Courage_Soup
09:37
Summary: It was a nice dinner - at least for me. You (the listener) paid, and I (the speaker) got to eat. But for you, dinner was an annoyance. I spent all night not-so-subtly making flirty eyes at other people, and generally being a bit of a cheeky shit. But really it's your own fault. You didn't let me have any dessert, so I'm basically vindicated for all my misbehaviour. No I won't apologise to you. Not even if you wrap those strong hands around my teasing neck and *squeeze*.
18:53
Summary: You (the listener) are upset after some coworkers insulted you. I (the speaker) come in to find that you've been crying. I'm annoyed that you wouldn't come and talk to me about your feelings, but I admit that we're very different in how we express emotion. I decide to show you that you shouldn't care about anyone else's opinion of you, and I'll do it by claiming you as my own all over again. Your pain is my pain, bitch boy, and I'm going to make you feel so good you forget it all.
15:42
Summary: I (the speaker) am caring for you (the listener) while you are sick. You're in a bit of a pitiful state. You're overheating and exhausted, and your throat is so hoarse you can barely squeak out single words. Words like "no"... Seeing you so helpless and frail starts to stir something inside me... And I did blow off my girlfriend to look after you... Sorry bro, but just be quiet and take it. I mean, if you didn't want this you'd just say "no", right?
09:53
Summary: Your jock bully and his friends are picking on you (the nerd) after gym class. Things go a little too far and he ends up frantically trying to get you to be quiet so he doesn't get in trouble. Later that night, he shows up at your house to check on you. The two of you get a little closer and the remember when things were different. Although he's still a bit of a dick, he shows you his softer side (literally and figuratively).
15:46
4(1)
Summary: All it took was a single moment of forgetfulness and I (the speaker) had you (the listener) at my mercy. If you hadn't left your phone in my room after making me do your assignments for you, I wouldn't have seen your gay porn filled search history. Now every time your meathead friends treat me like shit and you don't stop it, I make you come to my room and do as I say all night. Of course, you're *definitely* not gay, right? You aren't some fag like me or anything. You're doing this because of the blackmail. You actually hate this. Right? Sure. Keep telling yourself that as you suck my dick and fuck me deep, big boy. Maybe you'll finally be able to convince yourself. But just maybe, you'll realise hiding who you are is even more painful than the bullying "people like me" put up with.
20:46