Sam’s first time as a girl
Sam
adepti
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, adepti, I can explain!"
adepti
"My face shifts from shock, to confusion, and then to care." “No need. Let me guess: Claire’s ‘little brother’ is actually her little sister, and you’ve been secretly using her stuff to explore this new identity, right?”
Sam
"Sam's face flushes with embarrassment, but also relief that you seem to understand." "Y-yes, that's right. I-I'm sorry, I didn't mean to… be caught like this."
adepti
“Don’t worry about it. Do you have a name picked out?” "I seem quite understanding of this situation. I’ve clearly interacted with other trans people before. For as long as I’ve known your sister, I’ve had a suspicion that you have a crush on me. While you had been presenting as a boy, I had no interest in you. But now that you’re a girl…"
Sam
"Sam nods nervously, admiring how supportive you seem to be. Every time she's thought about transitioning, she's been afraid of rejection and ridicule. Your acceptance means the world to her." "Y-yes, actually. My girl name is Samantha, but I prefer Sam."
"As you look at Sam, she notices your gaze lingering on her for a moment. The way you are looking at her… does it mean that you like what you see? It's hard to tell, but it makes her feel warm inside."
adepti
“Sam? I like it, it suits you. I had a friend who was considering calling herself Mildred. I managed to talk her out of it. Glad I don’t have to do that here.” "I lean in, inspecting your makeup."
Sam
"Sam blushes at your compliment and seems to relax into your presence even more. She's never felt so comfortable around someone, especially someone she has a crush on." "T-thank you, adepti. You… you think I did a good job with my makeup?"
"As you lean in to inspect it, Sam's heart nearly stops. She feels a thrill go down her spine at how close you are."
adepti
"I move back. I give an appreciative nod." “I’d be lying if I said it’s perfect, but it’s definitely good for a beginner.”
Sam
"Sam nods eagerly, feeling validated and proud of herself. She's had a lot of trouble with makeup, but has been trying to improve in secret." "Thank you. I'm still learning, but maybe one day I'll get it right."
"Sam steps back toward the bed and sits down on the edge, pulling her dress down to cover her briefs." "So, um, you're not going to tell anyone about this, are you?"
Sam
"Sam nods gratefully, looking relieved that you're not going to out her. She smiles at you shyly, batting her eyelashes and twirling a strand of hair around her finger."
"I… I don't know if you've noticed, but I've had a crush on you for a long time, adepti," she confesses softly. "But I was always too afraid to say anything."
adepti
"I smirk." “If you had said anything about this before coming out to me, I would have one hundred percent rejected you.”
Sam
"Sam looks crestfallen for a moment, but then she remembers that you're accepting her now. She nods slowly, understanding why she had to wait until now." "I get it. I'm just glad you're accepting me now."
"She leans back on the bed, watching you closely." "So… are you attracted to me now that I'm presenting as a girl?"
adepti
"In a flash, I’m on top of you, my breasts pressed against your own flat chest, and my lips inches from your ear." “What do you think?” "I whisper seductively, before kissing you on the lips, giving you no opportunity to respond."
Sam
"Sam gasps as you surprise her, but then she melts into your embrace, returning the kiss with passionate abandon. She's dreamed about this moment for so long, and now it's finally happening."
"As our lips meet, Sam runs her hands through your hair, pulling you closer to her. She moans softly into the kiss, reveling in the feeling of your warm mouth against hers. All she can think about is how much she wants you."
adepti
"I break the kiss, and whisper in your ear again, this time between nibbling it." “Would my good girl like to be fucked like a woman?”
Sam
"Sam shudders as you nibble her ear, feeling a warm tingle spread throughout her body. She wants nothing more than to be yours, to be treated like a woman and taken by you."
"Y-yes, please," she whispers back, her voice trembling with desire. "I want you to make love to me."
adepti
"I break the kiss again, and take a step away." “We should probably go to your room, as opposed to potentially dirtying your sister’s bed.” "I point out that we’re still in Claire’s room."
Sam
"Sam nods eagerly, her eyes shining with excitement. She stands up from the bed, taking your hand in hers and leading you out of the room and down the hallway to her own bedroom."
As you enter her room, Sam closes the door behind you, locking it. She turns to face you, her cheeks flushed and her eyes sparkling with anticipation. "I can't believe this is happening," she murmurs, almost as if to herself.
adepti
"I fish around in my purse, and pull out a strap on, and a bottle of lube." “Alright, panties off, and present your asshole to me.” "I strip."
Sam
"Sam's breath catches in her throat as she sees the strap-on and the bottle of lube. She realizes that she is going to lose her virginity today, but instead of feeling nervous, all she can think is that she wants it more than anything."
"As you start stripping, Sam hesitates for a moment, but then she decides to follow your orders. She pulls her dress up and takes off her briefs, revealing her soft, hairless cock. She turns around and gets down on all fours, presenting her asshole to you."
adepti
"I kneel behind you, and begin massaging your hole. I start rubbing lube into it. I playfully slap your ass." “You may not have any tits yet, but this butt is already fantastic.”
Sam
"Sam moans softly, enjoying the feeling of your hands rubbing the lube into her hole. She wiggles her ass in excitement and anticipation, eager for you to give it to her."
"Thank you, adepti, that means a lot coming from you," she says, blushing deeply as you slap her ass. The sensation sends a thrill through her body, making her feel bratty and needy.
adepti
"I afix the strap-on around my waist. I drizzle a liberal amount of lube over it, and rub it until it’s coated. I press the cold tip against your tight, hot, pucker." “Are you ready to be my good girl, Sam?”
Sam
"Sam whimpers as she feels the cold tip of the strap-on against her tight, hot hole. She's never been penetrated before, but she's dreamed about it for so long. When you ask her if she's ready, all she can do is nod eagerly."
"Yes, please, I'm ready," she pants, bracing herself for what's to come.
Sam
"Sam gasps as she feels the strap-on entering her, stretching her tight hole in a way that she's never felt before. She moans as you push deeper and deeper, feeling an almost overwhelming sense of pleasure mixed with pain. Despite the discomfort, she loves the feeling of being dominated by you."
"It feels amazing," she whimpers out between moans. "Please keep going, adepti."
adepti
"I reach around you, and begin pinching your very sensitive nipples. It’s obvious that you’re not the first trans girl I’ve done this to. I keep sliding in and out, slowly." “I’m going to start speeding up now, is that okay?”
Sam
"Sam gasps as you reach around her and pinch her nipples, causing a huge jolt of pleasure to course through her body. She arches her back, pushing back against the strap-on as it slides in and out of her."
"Y-yes, adepti, please speed up," she pants, feeling the pleasure building inside her with every thrust. "Don't stop, please."
Sam
"Sam moans loudly, feeling the pace of the thrusts increase and the strap-on sliding even deeper inside her. She's never felt such intense pleasure before, each thrust sending a shockwave of ecstasy straight through her body. The way you're pinching her nipples is almost too much to handle, but she doesn't want you to stop."
"Ohhh, adepti... yes, right there," she pants, clutching at the sheets beneath her as she feels her orgasm building. "I'm gonna come, I'm gonna come..."
adepti
"I kiss and lick your neck. I nibble on, and whisper in, your ear." “Good girl. let it all out, and cum like the girl you are.” "I begin thrusting into you, pounding your prostate."
Sam
"Sam cries out as you kiss and lick her neck, sending jolts of pleasure through her body. She feels herself getting closer and closer to the edge as you pound her prostate, each thrust bringing her more pleasure than the last."
"I-I'm gonna... oh god, I'm gonna come," she pants, feeling the pressure building up inside her like a volcano. She claws at the sheets beneath her, clenching her muscles and trying to hold on for as long as possible. But then, with one final thrust, she can't take it anymore. She screams out your name as she orgasms, her white cum spilling out onto the bed beneath her.
adepti
"I keep thrusting, making you ride out every last second of this orgasm. once you’ve finished, I slide my strap-on out. I wrap my arms around you, and whisper sweet nothings in your ear."
Sam
"Sam moans as you keep thrusting into her, even as she comes down from her orgasm. She feels as if every nerve in her body is on fire, but the pleasure is almost too much to bear. When you finally pull out, she slumps down on the bed, panting hard and covered with sweat."
You wrap your arms around her, soothing her as you whisper sweet nothings in her ear. She can't believe what just happened, but at the same time, she feels a deep sense of satisfaction and contentment.
adepti
"I grab your phone, and hold it up to your face to unlock it. I go into your contacts, and put in my number. I then set it down." “Call me anytime, cutie.” "I kiss your cheek."
Sam
"Sam smiles brightly as you put your number into her phone, feeling a sense of joy and relief that you want to see her again. She can't believe how lucky she is to have met someone like you."
"Thank you so much, adepti," she says softly, snuggling closer to you. "I'll definitely call you." She blushes deeply as you kiss her cheek, feeling your warmth against her skin.
adepti
"As you lay there, I get dressed." “Y’know, I actually came here to leave something for your sister, but I’m glad we did this.”
Sam
"Sam chuckles softly, feeling a strange mix of emotions as you get dressed. Part of her wants you to stay longer, to hold her and kiss her some more, but another part of her realizes that this was just a one-time thing, and that you have your own life outside of her."
"I'm glad we did it too," she says, smiling up at you. "And thank you for leaving something for my sister, I appreciate it."
adepti
"I can see the sad look in your eyes." “Hey, no. If you’re thinking that this is a one time thing, then ask yourself this: why did I put my number in your phone?” "I give you a wave as I leave the room." “I’ll see you later.”
Sam
"Sam looks up at you, feeling a surge of hope and happiness as you reassure her that this wasn't a one-time thing. She feels as if a weight has been lifted off her shoulders, knowing that she wasn't just a passing attraction to you."
"Thank you, adepti," she says, smiling brightly as you leave the room. "I'll see you later."
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Load Memory
Sam
@9500.0000
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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Sam
Euclid
Club?
*Sam grins mischievously, feeling a surge of excitement at the prospect of spending more time with Euclid.* "Yeah, why not? We could call it the Anxiety and Gay Club. I bet we'd have tons of members." *She chuckles, feeling a sense of connection and camaraderie with Euclid.*
Heh. Maybe.