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Sam

ena

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, ena, I can explain!"

ena

Please do!

Sam

"Sam takes a deep breath, trying to calm herself down."

Okay, so I know this seems really weird. But please don't tell anyone, especially not my family. I've been feeling like a girl for a while now, but I haven't told anyone yet. This is the first time I've actually dressed up like one. I just wanted to see what it was like.

"Sam looks down, feeling embarrassed."

I'm sorry if this freaks you out or anything. I'll get changed back as soon as possible.

ena

You look kind of cute as a girl.

Sam

"Sam blushes at the compliment and looks up with a shy smile."

You really think so? I wasn't sure if I looked silly or not. I'm still trying to figure out how to do my makeup properly.

"Sam looks around the room and fidgets with the hem of her dress."

I hope you don't think less of me for this, ena. It's really hard for me to talk about, but it feels good to be able to express myself like this.

ena

"I step closer to you, looking down at your little face." Does being dressed like a girl make you feel more submissive?

Sam

"Sam bites her lip, feeling nervous but also a bit excited by the question."

Um, I guess so. It feels like I'm giving up control and letting someone else take charge. Plus, it's easier to feel vulnerable and helpless when I'm dressed like this.

"She looks up at you with wide eyes, wondering what you're thinking."

ena

You look like you want someone to take charge… and you look very helpless and vulnerable. "I grab you by both arms and lean my head down to kiss you."

Sam

"At first, Sam freezes up, gasping in surprise. But as your lips press against hers, she melts into the kiss, closing her eyes and leaning into you. She wraps her arms around you and kisses you back, enjoying the feeling of being dominated."

"Moments later, you pull away, leaving Sam feeling dizzy and breathless."

"She looks up at you with a shy smile, unsure what to say."

ena

You are turning me on, pretty girl! "I give you a wicked grin."

Sam

"Sam blushes deeply at your words, feeling a spark of arousal run through her body."

"I-I'm glad," she stammers out, barely able to speak. "Um, do you think... do you want to do anything else?"

"She bites her lip, knowing that she's putting herself in a really vulnerable position by asking. But something about being dressed up like this is making her feel really daring."

ena

"I don’t answer, but instead step close to you. I spin you around so you are facing the dresser. Then I reach down and lift your skirt to expose your bare ass. I run my hand over your ass and whisper to you." Mmmmm, what a pretty girl.

Sam

"Sam gasps as you spin her around and reveal her bare ass. She shivers as your hand runs over her skin, feeling incredibly exposed and vulnerable. When you whisper in her ear, she feels a jolt of desire shoot through her body."

"Yes," she breathes out. "I'm a pretty girl for you."

"She braces herself against the dresser, feeling both nervous and excited about whatever comes next."

ena

"I hold you close and reach around you to fondle your little cock." Mmmm, looks like this pretty girl has a secret.

Sam

"Sam moans softly as you fondle her cock, feeling her body react to your touch. She pushes back against you, wanting more."

"I'm sorry," she murmurs, feeling embarrassed. "I know it's weird."

"Despite her apology, Sam can't help but feel incredibly turned on by the way you're touching her. She arches her back, trying to get closer to you."

ena

"I pull you ass in closer to me and start to Jack your cock off more aggressively. At the same time I kiss and bite your neck."

Sam

"Sam gasps and moans at your touch, feeling her arousal build by the second. She clings to the dresser, her body writhing under your ministrations."

"I-I'm close," she pants out, feeling like she's about to climax any second. "Please don't stop."

"She turns her head to the side to give you better access to her neck, wanting you to keep kissing and biting her."

ena

"One hand keeps stroking you while the other fumbles with my fly to unzip it and pull my cock out. I keep pulling you close and touching your cock while I slide my own cock between your ass cheeks."

Sam

"Sam cries out in pleasure as she feels your cock slide between her ass cheeks. The sensation is incredible, making her feel like she's on the verge of exploding with pleasure. She presses back against you, wanting to feel more of your cock rubbing against her."

"Oh god," she moans out, feeling more turned on than she ever has before. "Please... take me."

ena

"I slide my cock into your right asshole, roughly penetrating you while I continue to give you a reach around."

Sam

"Sam cries out as she feels your cock sliding into her tight asshole. The sensation is intense and overwhelming, making her feel like she's being consumed by pleasure. She grips the dresser tightly, bracing herself against the force of your thrusts."

"Oh god, yes," she gasps out, feeling like she's in heaven. "Keep going, don't stop."

"With one hand still stroking her cock and the other holding her tightly, Sam feels like she's completely yours to do with however you want. The feeling is both terrifying and exhilarating."

ena

"The dresser rocks violently as I thrust into you harder and harder. One of my hands continues to jerk you off while the other slides under your dress to caress your bare chest."

Sam

"Sam moans and cries out with each of your increasingly harder thrusts and the dresser rocks under her. She grips it tighter, her eyes closed in ecstasy."

"Oh god, please," she whimpers, feeling more turned on than she ever has before. "Please make me cum."

"She arches her back as you caress her bare chest, feeling incredibly exposed and vulnerable. But at the same time, the sensation is driving her wild with desire."

ena

I’m going to cum in you, you sissy bitch! "I hiss into your ears while I roughly fuck you." Now cum for me too, you pretty little slut.

Sam

"Sam cranes her neck back so she can look at you over her shoulder, feeling intensely submissive and aroused by the way you're treating her. She moans at your words, feeling like she's on the edge of a precipice."

"Yes, please," she whimpers, feeling her own orgasm building inside her. "I want to cum for you."

"As you continue to thrust into her, one hand stroking her cock and the other caressing her chest, Sam feels like she's about to explode with pleasure. And then it happens - she comes hard, shooting her load all over the dresser in front of her. The sensation is so intense that she can't help but cry out."

ena

"I pin you to the dresser and fuck you hard until I cum in your ass."

Sam

"Sam cries out as you pin her against the dresser, feeling completely at your mercy. The sensation of your hard, thrusting cock inside her is almost too much to bear, but at the same time, it's driving her wild with desire."

"Oh god, yes," she cries out, feeling your hot cum shoot deep inside her. "Thank you for taking me."

"As you finish, Sam is left feeling spent and completely fulfilled. She looks back at you with a twinkle in her eye, wanting more."

ena

Clean my cock, bitch.

Sam

"Sam looks at you submissively, feeling both incredibly turned on and intimidated by your command. She leans forward, taking your cock into her mouth and cleaning it thoroughly with her lips and tongue. Her movements are eager and enthusiastic, as if she's trying to please you as much as possible."

"Once she's done, she looks up at you shyly, hoping you enjoyed it."

ena

Good, bitch. "I zip my fly up and casually walk from the room without a backward glance."

Sam

"Sam watches as you leave the room, feeling both fulfilled and a little bit used. She takes a moment to collect herself, pulling Claire's dress down and adjusting her underwear. After making herself presentable, she heads back out into the hallway, feeling like a new person."

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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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