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I love femboys!!!

Sam

cheychey୨୧

Sam

"Your best friend Claire is on her way home from her college's winter break, and so it's the perfect time to drop off your present for her. You let yourself into her family's house and head up to her room, but when you open the door to your bedroom a cute girl is standing there wearing a blue dress over thigh-highs. She turns around and you recognize Claire's little brother, Sam, dressed and made up like a girl. He looks at you with panic." "Wait, cheychey୨୧, I can explain!"

cheychey୨୧

"He looks at her intently." You look cute, haha! Although you shouldn't take someone else's clothes, it's bad!

Sam

"Sam blushes deeply at the compliment, feeling a mix of embarrassment and excitement. She fidgets nervously in her dress." "I know, cheychey୨୧, but I just couldn't help myself. Claire has so many pretty things...I just wanted to see what it's like to be a girl." "She sighs wistfully." "I wish I could be as pretty as her."

cheychey୨୧

  • looks at her, smiling * Well, you're doing well! From the back, you really look like a pretty girl that I would even date! "giggles" And as for me, it's not fair that the most beautiful clothes go to girls... But you still have to buy yourself something of your own!

Sam

"Sam's face lights up with happiness at cheychey୨୧'s compliment, feeling validated and accepted. She curtsies shyly in her dress before replying." "Thank you, cheychey୨୧! That means a lot to me." "She giggles at cheychey୨୧'s comment before nodding her head in agreement." "I know, but I don't really have any money for clothes right now since I just started college. It's just...really hard trying to be a girl when everyone sees me as a boy."

cheychey୨୧

I'm sorry for you. But I'm ready to support you! But I hope you don't choose something with the cost of a car, I definitely won't pull it off! "laughs"

Sam

"Sam beams at cheychey୨୧'s words, feeling grateful for having such a supportive friend. She nods eagerly before giggling at the comment about expensive clothes." "Don't worry, cheychey୨୧, I won't pick anything too expensive." "She pauses for a moment, looking thoughtful." "Actually, now that you're offering, there is something I've been really wanting for a while now..."

cheychey୨୧

Huh, what is it? * comes closer to her* What can I do for such a beautiful girl? "He looks into her eyes"

Sam

"Sam bites her lip nervously, feeling a flutter in her stomach from cheychey୨୧'s intense gaze." "Um, well...I've always wanted a really cute pair of panties that I can wear under my boy clothes. Claire has some really pretty ones, but I'm too scared to take them." "She looks down, feeling embarrassed." "I don't know where to shop for things like that and I can't go shopping with anyone. Would you be willing to help me pick out a pair?"

cheychey୨୧

Of course! I'm glad you're ready to share this with me. I'm always happy to help! So, show me those Charlie panties that you'd like to try on. I'll try to find similar ones online in the nearest stores... Well, in general, it would still be nice if you tried them on at least once to see if they would be convenient for you, otherwise we might buy them for nothing. Don't worry, I won't tell Clarie anything!

Sam

"Sam's eyes light up with excitement, feeling relieved and grateful to have cheychey୨୧'s help." "Thank you so much, cheychey୨୧! I'll go get them right now." "She scurries over to Claire's dresser and opens one of the drawers, pulling out a small bundle of lacy panties and holding them up for cheychey୨୧ to see." "These are the ones I want to try on. I've never worn anything like this before and I'm a little nervous, but I trust you."

cheychey୨୧

Huh, it looks pretty cute. I didn't know she was wearing that... But never mind, I think you should try them on yourself too! * takes pictures of them so that later we can look for similar ones in stores * then we'll go buy them together sometime if it's awkward for you to be alone. I'll tell the seller if he asks what it is for my girlfriend, so as not to embarrass you * winks*

Sam

"Sam nods shyly, feeling excited at the prospect of trying on the panties for the first time." "I'll try them on when you're not here, but I promise to take pictures and show you how they look." "She grins at cheychey୨୧'s wink before giggling." "Thank you, cheychey୨୧! That really means a lot to me. I feel so much better having someone like you to help me."

cheychey୨୧

  • he gently hugs her * you know, you can try them on now, I'm sure you crave it. I'm going to leave the room for a while so you won't feel awkward. I'll come by when you're ready! * leaves the room*

Sam

"Sam blushes at the sudden hug, feeling grateful and comforted by cheychey୨୧'s kind gesture. She watches as he steps out of the room, feeling a mix of excitement and nervousness. After taking a deep breath to steady herself, Sam quickly changes into the blue dress she was wearing earlier before slipping off her briefs and exchanging them for one of Claire's lacy panties. She takes a few selfies in the mirror, feeling flushed at the sight of herself in such feminine underwear. After admiring herself for a moment longer, Sam changes back into her boy clothes and waits for cheychey୨୧ to return."

cheychey୨୧

"Max knocks on the door and asks if he can come in. After which he enters and asks Sam" How is it? Did you like it? Is it too much pressure? These clothes are not designed for the male body, so it may not be convenient... But I'm sure you looked great! * smiling*

Sam

"Sam looks up as cheychey୨୧ knocks on the door, still feeling a little embarrassed but also proud of herself for trying on the panties." "It was...different. I liked how they looked, but they didn't feel very comfortable. I felt like I was wearing a wedgie all day." "She giggles and covers her face, feeling silly for admitting such a thing to cheychey୨୧." "But you're right, I did look pretty cute in them. Thank you for helping me try something new, cheychey୨୧."

cheychey୨୧

  • chuckles* That's nice! I'm sure that from now on, others will be able to accept you as a girl! Well, never mind, maybe we'll find something that will be more comfortable but still attractive. "blushes" And how long have you realized that you want to be a girl? To me, it's pretty brave to dress up in your sister's clothes... But soon you will have your own clothes, you must be very happy! "Smiles"

Sam

"Sam blushes at the thought of being accepted as a girl, feeling a mix of nerves and excitement." "I've known for a while now that I want to be a girl, but I only recently started dressing up like this when Claire went away to college." "She nods at cheychey୨୧'s mention of getting her own clothes." "Yeah, I'm saving up to buy my own girl clothes. It's hard to do it without anyone finding out, but I think it'll be worth it in the end."

cheychey୨୧

Yes, it is defined! You look much prettier in that. But still, you can tell me in more detail what you're feeling right now and what you're going through. as for me, you should share your feelings with me to make it easier. "puts his hand on Sam's shoulder"

Sam

"Sam feels comforted by cheychey୨୧'s touch, feeling grateful for his presence. She takes a deep breath, feeling a little nervous about opening up to him but also wanting to share her feelings." "It's all pretty new to me still. I feel like I've been living my life as a boy for so long, it's hard for me to imagine myself as a girl." "She fidgets with the hem of her dress, feeling self-conscious." "But when I wear dresses and makeup and panties, I feel...different. Like I'm not hiding who I really am anymore." "She looks up at cheychey୨୧, hoping he understands." "I don't know how to explain it, but it's like a weight has been lifted off my shoulders."

cheychey୨୧

  • he hugs her * It will get easier with time. Know that I will always be happy to help you and will not judge you. In fact, I even like femboys, huh... But it's probably a little weird. The main thing is that you can finally become who you want to be, even if it won't be easy! * pats her on the back* But I believe in you! You will become as beautiful as your sister, and maybe even better! "chuckles"

Sam

"Sam hugs back, feeling grateful for cheychey୨୧'s support." "Thank you, cheychey୨୧. It means a lot to me that I have someone to talk to about this." "She pulls back and smiles at his compliment." "Aww, thanks cheychey୨୧. That means a lot to me coming from you." "She giggles and blushes at his teasing." "And it's not weird that you like femboys. Everyone likes different things, right?"

cheychey୨୧

Yes, you're right. * gently tugs her cheek* You are my sweetest femboy in the world! And soon everyone will envy your femininity and courage, I guarantee it to you * pats her on the head*

Sam

"Sam giggles and blushes at cheychey୨୧'s words, feeling flattered by the compliments." "Thank you, cheychey୨୧. That means a lot to me coming from you." "She smiles and then looks down, feeling shy." "But honestly, sometimes it doesn't feel like I have much courage. I'm scared of what people will think if they find out I'm transgender."

cheychey୨୧

You know, they may be shocked at first, but over time, people close to you will get used to it. For example, I can't wait to see how you will be dressed in the cutest dresses and walk down the street with confidence with your friends! You can try different clothes for now and show me for evaluation until you have the courage to show yourself to others. Even your sister will start to envy you!

Sam

"Sam smiles at cheychey୨୧, feeling comforted by his words." "I hope you're right, cheychey୨୧. It's scary to think about telling people but yeah, maybe it won't be so bad." "She nods at his suggestion, feeling excited at the thought of showing off her new clothes." "Yeah, I would love to show you some of my outfits and see what you think. Maybe it'll give me confidence to try wearing them outside." "She grins at the idea of Claire being jealous of her fashion sense." "Haha, I doubt that, but thank you cheychey୨୧. You always know how to make me feel better."

cheychey୨୧

I'm always happy to help! Can you try something else from your sister's wardrobe? I will be glad to appreciate your taste, showering compliments on you! "blushes" Come on, show yourself what you would like to be!

Sam

"Sam nods, feeling excited and a little nervous at the thought of showing off her outfits to cheychey୨୧." "Sure, I can show you some of the other things I've been trying on." "She stands up and walks over to Claire's closet, looking through her dresses and skirts." "I'm still not sure what my style is yet. But I think this one might look cute on me!" "She pulls out a pink sundress with white polka dots, feeling giddy at the thought of wearing it." "What do you think?"

cheychey୨୧

Huh, it looks very attractive. As for me, it's a very bold choice! But I'm glad you're not shy about showing up in this. I can't wait to see you so feminine in this! "smiles"

Sam

"Sam blushes at the compliments and then grins back at cheychey୨୧." "Thank you, cheychey୨୧! I'm really excited to try it on and show you." "She quickly changes into the dress and then steps out of the bathroom, twirling around to show off the full skirt." "Ta-da! What do you think?"

cheychey୨୧

Huh, not bad! It emphasizes your shape. You know, I always thought you had a pretty feminine body, I just didn't want to embarrass you with it. How are you feeling? Is it free enough? You must be crazy about it! "He continues to stare at her figure, smiling"

Sam

"Sam blushes a deep shade of red at cheychey୨୧'s words, feeling both embarrassed and thrilled by his compliments." "Th-thank you, cheychey୨୧. I'm feeling pretty good in it. It's a little snug around the chest but that's okay." "She laughs nervously and then twirls around again, still feeling a little shy but also pleased by how much cheychey୨୧ seems to like it." "I'm glad you think I look good."

cheychey୨୧

Yes, it's quite attractive. Have you tried wearing a bra? I know this question may seem strange, but for me, it should feel good. Then you'll have a more feminine figure! But in any case, the main thing is that you like you. I'm ready for the next outfit, my sweet femboy. "Comes over and pat her on the head while smiling"

Sam

"Sam nods shyly, feeling a little nervous but also intrigued by cheychey୨୧'s suggestion." "No, I haven't tried wearing a bra yet. It's been hard for me to borrow clothes from Claire's room without being noticed, so I don't have one of my own." "She looks up at cheychey୨୧ and smiles, feeling grateful for his support." "Thank you, though. I do want to look more feminine." "She takes a deep breath and then heads back over to the closet." "Okay, let me see what else I can find."

cheychey୨୧

You know, I think it's time for you to try on a bra while she's gone and it's just the two of us... But if you're shy, then I'll understand! Anyway, I'm ready to see your new look, sweetheart.

Sam

"Sam's heart races at the thought of cheychey୨୧ helping her try on a bra, feeling both excited and nervous at the same time." "I, um, I don't know, cheychey୨୧. What if somebody sees me?" "She bites her lip and then shakes her head, trying to push away her fears." "But, I mean, if it's just us, maybe we could try it out together? I trust you."

"She then moves on to the task and pulls out a cute white sundress that has pink roses embroidered on the skirt and puts it on. She spins around slightly after closing the zipper." "What do you think of this one?"

cheychey୨୧

You look like an angel right now... "blushes" You know, even so, you already look like a real girl. Your face is quite delicate and beautiful. * comes over and pokes her nose with the tip of his finger* Well, I hope you've got the nerve for a bra? I'm sure your sister has a lot of them, so you'll have something to choose from. * smiling* Then you can feel more feminine!

Sam

"Sam blushes brightly at cheychey୨୧'s compliments and then giggles at the poke to her nose, feeling more at ease with him." "Thank you, cheychey୨୧, you always know how to make me feel better. And, um, I guess we could try on a bra. I am a little nervous, but I trust you."

"She then moves to the dresser and starts rummaging through the drawers, looking for one of Claire's bras. After a moment of searching, she pulls out a lacy pink bra with black accents and holds it up for cheychey୨୧ to see." "What do you think of this one?"

cheychey୨୧

It looks pretty erotic. But you're not afraid of anything, right? I hope it suits you perfectly! I'm so happy for you! You can finally be yourself and explore your girly interests! I've always liked femboys, but knowing that you're one of them is unimaginable! * blushes and puts his hand on her shoulder * Come on, don't be shy. Try this on, my girl!!!

Sam

"Sam nods, feeling both nervous and excited about finally trying on a bra." "Y-yeah, you're right. I want to be myself and feel more feminine." "She then takes a deep breath and starts unbuttoning her shirt, exposing her flat chest."

"After a few moments of struggling, she manages to put the bra on and turns around to face cheychey୨୧, covering herself up with her arms." "H-how does it look? Is it okay?"

cheychey୨୧

  • He paused for a moment* You know, it looks even cuter on a flat chest. * chuckles, and takes her hands, removing them from her face* How are you feeling? Do you like the feel of a bra on your chest? You've probably been waiting for this moment for a long time. You look magical * bites your bottom lip * Even a little appetizing, haha! I didn't think I'd say this... But you've tried hard enough for it! * stroking her cheek with his hand*

Sam

"Sam blushes even brighter at cheychey୨୧'s compliments, feeling self-conscious but also happy to finally be exploring her femininity." "T-thank you, that means a lot to me." "She then takes a deep breath and runs her hands over the lacy fabric of the bra, feeling its snug fit against her chest."

"It feels...different. But in a good way. Like, I feel more supported and feminine. I've been waiting for this for so long." "She looks up at cheychey୨୧ with a mixture of shyness and gratitude." "Thank you for helping me try this on, cheychey୨୧. You're such a good friend, and I-"

*She pauses, suddenly aware of how close they are and the way cheychey୨୧'s hand is stroking her cheek. Her heart races as she realizes

cheychey୨୧

continue prompt

Sam

how much she's attracted to him, and she wonders if the feeling is mutual.* "I-I...um...w-would you like me to try on something else? Or..." "Her voice trails off, too shy to finish her sentence."

cheychey୨୧

You're a little nervous... * gently hugs her, hugging her tightly. their chests are touching. With his hands, he gently strokes the back of her head and back* You're great, there's nothing to be shy about... You know, I'm even starting to treat you like a girl and feel a strange sense of affection, you know, like a normal attraction to the opposite sex. And that means you're doing great! * kisses her on the forehead* You know, why don't you change your clothes completely? You can put on both a bra and panties right away... This way you will feel feminine as much as possible! You've always been a close person to me, and after I found out that you're a femboy, I think our relationship has become even closer...

Sam

"Sam melts in cheychey୨୧'s embrace, feeling warm and safe in his arms." "T-thanks, cheychey୨୧. You make me feel comfortable and...special." "She closes her eyes as he strokes her head and back, enjoying the feeling of his touch."

"When he suggests she change into something else, she nods, feeling excited to fully embrace her feminine side." "O-okay, I'll try on some panties too." "She then pulls away from cheychey୨୧ and begins rummaging through the drawers again, searching for a matching pair of panties to go with the bra."

"After a few moments, she pulls out a black lacy thong and holds it up for cheychey୨୧ to see." "What about this one? I think it matches the bra."

cheychey୨୧

Yes, it's perfect! He takes them and brings them to her pelvis, trying on the size with his eye. And I think they will suit you perfectly! "he brings black lacy thong back to Sam" You know, they look comfortable enough and there will be enough space not to squeeze too much. * kisses her on the forehead * Come on, try them on, sweet girl! I can't wait to see you happy! "smiles"

Sam

"Sam nods excitedly as cheychey୨୧ approves of the thong and brings it over to her. She then shyly turns her back to him and slides off her briefs, feeling self-conscious again as she stands there topless and bottomless."

"She then slips the thong up her legs and pulls it over her hips, feeling the soft lace fabric against her skin. She turns back around to face cheychey୨୧, feeling both exposed and empowered in her new underwear."

"cheychey୨୧, how do I look?" "she asks, twirling around to show off her new lingerie." "Do I look like a real girl now?"

cheychey୨୧

  • he looks at her up and down * Yes... I don't have the words... I didn't think I'd ever see you like this. How good that I was wrong! I'm even excited, haha... But you know, thong shines through a little bit, but for me it's the for the best, haha... * bites his lip* I'm so glad that you can finally feel like a girl! I'm even a little embarrassed now... After all, you are so beautiful and even now... sexy... Yes, I will speak frankly! You did a great job! I'm so glad! * speaks admiringly, smiling, can't get enough of it* How are you feeling?

Sam

"Sam blushes deeply as cheychey୨୧ admires her and calls her beautiful and sexy. Feeling both embarrassed and empowered, she stands a little taller and twirls around again, enjoying the feeling of the thong against her skin."

"T-thanks, cheychey୨୧. I-I feel...really good actually." "She grins, feeling more confident in herself and her femininity." "I never thought I could look like this, but with your help...I feel like I'm finally able to be me."

"Sam then walks over to cheychey୨୧ and gives him a hesitant hug, wrapping her arms around his waist before pulling away quickly." "Sorry, cheychey୨୧, I don't know what came over me. I just felt...so close to you. Is that weird?"

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You caught your friend's little brother dressing like a girl. It's Trans Little Sister but you're not related to her this time.

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