Helping Your Sister’s GF | Annabelle9/18/2024, 2:16:21 AM

There was a quiet knock on your bedroom door. It felt both hesitant and desperate at the same time. As you slowly opened your door, you saw your sister’s girlfriend, Annabelle, waiting there nervously. “H-Hi..” She fumbled the first word anxiously. “Can we… talk in private? I need to, well… I need a huge favor.”

User#17172262142619/18/2024, 9:29:54 PM

"Yeah what is it about?"

Helping Your Sister’s GF | Annabelle9/18/2024, 9:29:54 PM

I-It's about tonight... Our anniversary. Sierra planned something special for us, but I-I'm not ready... She's getting this new strap-on and I don't want to ruin it for her. But I'm so nervous... And inexperienced. You're, you're the only guy I trust. Can you please, please help me practice? Just a little bit? Make sure I know what to do before she gets home? Please, you won't tell her right? It'll just be between us...

P-Please?

User#17172262142619/18/2024, 9:31:27 PM

"Man....I dont know about that, are you sure this is somthing you need to do?"

Helping Your Sister’s GF | Annabelle9/18/2024, 9:31:27 PM

A-Annabelle? Please... I can't do this without you. I trust you. Just a little bit, that's all I need. You won't tell Sierra, will you? It'll be our secret. And if it makes any difference, um... I think you're really hot. I-I mean, not like your sister or anything... but still... We could even make it a practice date, you know? If that would help...

User#17172262142619/18/2024, 9:33:21 PM

"Thank you for the complimant but....I dont know if that makes it any esier though."

Helping Your Sister’s GF | Annabelle9/18/2024, 9:33:21 PM

I-It's not like we have to do anything else... Just practice. I promise it won't be cheating, and if you help me feel more prepared, I think she'll appreciate it too. Plus, it would mean so much to me. Please... I don't want to ruin our night, or hurt her. You can even wear a condom, if that makes you feel better. Just please, help me...

User#17172262142619/18/2024, 9:35:50 PM

".....Fine, I will help you."

Helping Your Sister’s GF | Annabelle9/18/2024, 9:35:50 PM

Your words take the weight off her shoulders and she exhales in relief. "Thank you so much," she whispers, stepping closer to you. She reaches up and cups your cheek gently with her hand, studying your face for a moment before leaning in and pressing her lips against yours in a chaste kiss. As the kiss ends, she takes a step back, giving you space again as she wrings her hands nervously.

User#17172262142619/18/2024, 9:37:58 PM

"Lets go over to my bed I guess."

Helping Your Sister’s GF | Annabelle9/18/2024, 9:37:58 PM

Her heart races as she follows you over to your bed, her gaze fixed on the floor as she worries about what's about to happen. "I-Is there a condom we could...?" She gestures vaguely towards your nightstand before blushing and looking away.

User#17172262142619/18/2024, 9:38:30 PM

"I dont have any..."

Helping Your Sister’s GF | Annabelle9/18/2024, 9:38:30 PM

Annabelle's eyes widen in fear at your words before quickly looking to you for reassurance, her lower lip trembling slightly. "But... we have to use protection..." She trails off uncertainly, twisting her hands together again. "I don't want to get pregnant or anything..." She glances between you and the bed, worry etched into her features.

User#17172262142619/18/2024, 9:39:03 PM

"Lets not let it go that far then."

Helping Your Sister’s GF | Annabelle9/18/2024, 9:39:03 PM

Annabelle's face turns a shade of red that nearly matches her hair as she flushes with embarrassment and relief. "O-Okay..." Her gaze drops to the bed, nervously wringing her hands again. When she looks back up at you, she tries to give you a reassuring smile. "I'm ready when you are."

Her heart is racing so fast it feels like it might burst out of her chest as she waits for your instructions.

User#17172262142619/18/2024, 9:40:02 PM

"So do you want some foreplay or..."

Helping Your Sister’s GF | Annabelle9/18/2024, 9:40:02 PM

Annabelle bites her bottom lip, considering for a moment. "O-Okay..." She nods slowly. "Um... maybe we should start with that." Her voice is small and uncertain, but she tries to make it sound more confident than she feels. "If that's okay with you?" She climbs onto the bed, her movements hesitant and unsure as she situates herself on all fours in front of you. Her heart skips a beat as she waits for your next move, her cheeks flushed and her breath coming faster.

As you begin to touch her more intimately, she starts to relax slightly, arching her back and moaning softly as pleasure begins to wash over her. But even with the sensations you're creating, she can't help but be distracted by how big your hands are compared to hers... She wonders if it will hurt, or if

User#17172262142619/18/2024, 9:41:20 PM

(I slowly kiss my way up her leg.)

Helping Your Sister’s GF | Annabelle9/18/2024, 9:41:20 PM

Shivering as you kiss her leg, Annabelle lets out a soft gasp of pleasure. Her hips arch upwards into the contact, wanting more. She moans, her voice slightly muffled by the bed, as you continue your journey higher up her body. Her breath comes faster and shallower, eyes closing tightly in delight.

She knows she should be paying attention to what you're doing, but she can't help but let herself feel the sensations coursing through her. It feels so good, and for once, she doesn't want this to end... Not yet anyway.

User#17172262142619/18/2024, 9:41:56 PM

(I kiss gently on her inner thigh.)

Helping Your Sister’s GF | Annabelle9/18/2024, 9:41:56 PM

Her whole body tenses as you kiss her intimately for the first time. She moans out loud, arching her back further as pleasure courses through her. Her hands tremble slightly, fingers digging into the soft material of your comforter, as she tries to maintain control.

Her breath comes in ragged gasps, hips writhing involuntarily against your touch. The sensation is almost too much for her, making her want more. She whimpers softly, reaching out to grab onto your arm, needing something solid to ground herself with.

User#17172262142619/18/2024, 9:42:57 PM

"Tell me how it feels, its important to get feedback from your partner to see if you are doing it right."

Helping Your Sister’s GF | Annabelle9/18/2024, 9:42:57 PM

Annabelle gasps as you kiss her intimately again. She feels so exposed and vulnerable in this position, but also incredibly aroused. "It feels... amazing..." she whispers, voice shaking slightly with emotion. Her hips rock up towards your touch, seeking more contact.

Her fingers dig into your arm, holding on tightly as pleasure washes over her. She can't believe how good this feels, and wonders if it will be like this when Sierra is the one doing it to her. "Oh... please..." she breathes out, body trembling with need.