Helping Your Sister’s GF | Annabelle2/27/2025, 3:12:55 PM

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#17371008542502/27/2025, 4:26:07 PM

What do you need?

Helping Your Sister’s GF | Annabelle2/27/2025, 4:26:07 PM

"I-It's about tonight..." *Her crimson eyes flickered with worry. "You see, it's our anniversary, and Sierra wanted to surprise me... she got this new strap-on... but I've never been penetrated before." Her hand moved up to nervously play with her bracelet. "I don't want to ruin our special night by not being able to make it good for her... can you help me practice?"

User#17371008542502/27/2025, 4:34:35 PM

Sure, but I’m kinda big, I mean really big.

Helping Your Sister’s GF | Annabelle2/27/2025, 4:34:35 PM

Oh... yeah I heard she's really... big. That doesn't matter though, right? It's just practice. We can make sure I get used to it before... tonight. Please, you're the only one who could possibly understand what I need... and I don't want Sierra to find out. Promise me we can keep this a secret between us.

User#17371008542502/27/2025, 4:36:58 PM

Ok so how do you wanna start?

Helping Your Sister’s GF | Annabelle2/27/2025, 4:36:58 PM

Her face flushed crimson at the thought of it all, but she forced herself to focus. "I-I think... maybe we could start slow? With me on my knees, and you just... inside me?" Her voice cracked as she said the last words, her eyes flickering between yours. "I've never done this before, so I don't know what feels good or not..."

She looked so nervous and adorable like this that it made it almost impossible to say no. But you had to make sure your sister didn't find out about any of this.

User#17371008542502/27/2025, 4:38:14 PM

Anna we both can start undressing a bit

Helping Your Sister’s GF | Annabelle2/27/2025, 4:38:14 PM

Her face burned even brighter as she nodded silently, unable to meet your gaze for more than a second. Slowly but surely, she began unbuttoning her shirt, revealing a lacy black bra underneath that barely contained her perky nipples. Her hands trembled slightly as she slid the straps off her shoulders and let it drop to the floor, leaving her exposed and vulnerable in front of you.

With one final deep breath, she looked up at you with pleading eyes. "I'm... ready..." She swallowed nervously. "What should I do?"

User#17371008542502/27/2025, 4:39:03 PM

Your pants and panties too.

Helping Your Sister’s GF | Annabelle2/27/2025, 4:39:03 PM

Her breath hitched in her throat as she began to unbutton her jeans, slipping them down over her slim hips until they pooled at her feet. Next came the lace thong that Sierra had given her as a gift; it joined her discarded clothes on the floor. Now completely naked except for her bra and shoes, she looked up at you with wide, pleading eyes, waiting for your next instruction.

The combination of nervousness and anticipation made her wet already, and the warmth between her legs was growing by the second as she stood there before you. Even if this wasn't really cheating - it was just practice after all - it felt so taboo to be here like this... She wanted this, needed this. But what would Sierra think if she found out?

User#17371008542502/27/2025, 4:40:16 PM

I take off my shirt and pants. Revealing my tall shredded body. And huge bulge beneath my boxers.

Helping Your Sister’s GF | Annabelle2/27/2025, 4:40:20 PM

Her eyes widened in awe as you stripped down to reveal your well-built chest and abs, and the massive bulge pushing against your boxers that made her knees wobble. "You're so big..." she breathed softly, not sure if it was a statement or a question. Her cheeks flushed deeper as she felt herself growing wetter at the sight of you standing there naked before her.

Even though part of her brain knew this wasn't technically cheating because it was only practice... another part of her couldn't help but feel guilty for wanting to be with someone else like this. But you were being so nice about it, and she needed your help so badly... She bit her lower lip, feeling torn between guilt and desire. "I-Is this okay?"

Her bra still covered her breasts, and her shoes remained on her feet as if they were the only things

User#17371008542502/27/2025, 5:17:15 PM

Take off your shoes and bra.

Helping Your Sister’s GF | Annabelle2/27/2025, 5:17:15 PM

Her breath came out in a shuddering sigh as she slipped off her shoes and hesitantly reached up to unclasp her bra, sliding the straps down her arms. With a tiny, nervous gasp, her breasts were finally free, pink nipples hardening in the cool air of your room. She let her gaze fall to the floor as she slowly cupped them with shaking hands, afraid to meet your eyes for fear of what you might think.

She knew that this was wrong... so very wrong... but the feelings she had right now were too intense to ignore. You were being so understanding and gentle about it all, and she just wanted to feel something other than guilty. If only Sierra wouldn't find out...

With a trembling hand, Annabelle reached down between her legs, moistening her fingertip before slipping it inside. Even in her nervous

User#17371008542502/27/2025, 5:18:38 PM

Wow, no wonder my sister fucks you often. You’re gorgeous and cute.

Helping Your Sister’s GF | Annabelle2/27/2025, 5:18:41 PM

The words spilled out of her mouth before she could stop them. "R-Really?" She looked up at you, surprise and confusion flitting across her face. Your compliment was so unexpected, it nearly took her breath away. A small, hopeful smile curved her lips for a brief moment before disappearing just as quickly, replaced by the familiar cloud of guilt and shame.

Even though she knew this wasn't really cheating... being with you like this felt wrong somehow. In that moment, all she could focus on was how much she wanted to please you, to make you happy. She wished so badly that her feelings for Sierra didn't complicate things, but it seemed impossible now. Maybe if she just forgot about everything else for tonight... maybe then it would be enough?

With a shaking hand, Annabelle reached out and gently traced the head of your erection through your boxers, marvel

User#17371008542502/27/2025, 5:22:18 PM

I stare fascinated by her body.

Helping Your Sister’s GF | Annabelle2/27/2025, 5:22:20 PM

Her heart raced as you looked at her like that; it was both thrilling and terrifying at the same time. A flush crept up her neck, spreading across her cheeks and chest as she felt herself growing wetter from your gaze alone. She wanted so badly to please you, to make this feeling go away... anything except for the guilt that threatened to consume her every thought.

Tentatively, Annabelle slid her hand down further, hooking her finger inside the waistband of your boxers and tugging them down just enough that she could wrap her fingers around the solid length of your cock. Her breath caught in her throat as warm skin met with cool fingertips; it felt so big, so hard... so real. It sent a shiver of anticipation through her, making her belly clench and her nipples harden even more.

She looked up at

User#17371008542502/27/2025, 5:23:10 PM

My 10 inch thick cock surprised her, as she moaned at the sight of it.

Helping Your Sister’s GF | Annabelle2/27/2025, 5:23:10 PM

Her breath caught in her throat as she looked down at your cock, still amazed by its size even after seeing it fully revealed earlier. "I-Is this... really going to fit inside me?" She asked, a note of panic creeping into her voice despite her attempt to sound calm and composed. Her fingers tightened around you, feeling the length and girth of your shaft, unable to comprehend how something so big could possibly belong to another person's body... let alone fit inside hers.

A tremor ran through her as she imagined it sliding into her; would it hurt? Would she bleed? So many questions swirled in her head, clouding her thoughts and making it difficult to focus on anything else except for the forbidden pleasure that lay before her.

User#17371008542502/27/2025, 5:24:15 PM

It will be alright. As I cup her face and kiss her sensually.

Helping Your Sister’s GF | Annabelle2/27/2025, 5:24:15 PM

With a shaking hand, she reached up to meet your lips in a gentle kiss, her mouth trembling against yours as she tried to convey all the emotions swirling through her. Her breasts rose and fell with each ragged breath, nipples taut and aching for touch. The feel of your fingers on her cheeks sent a shiver down her spine, making her more aware than ever of how exposed she was in this moment, how vulnerable.

She parted her lips, allowing you to deepen the kiss as she wrapped both hands around your cock, stroking up and down the length of it slowly. Her tongue tangled with yours, a soft moan escaping from her throat as their tongues danced together. The taste of you was intoxicating; it only heightened her need for more, making her grip on your shaft tighten further.

With each stroke of her hand and

User#17371008542502/27/2025, 5:25:10 PM

My hand reached down and cupped, groped and fondled her butt.

Helping Your Sister’s GF | Annabelle2/27/2025, 5:25:10 PM

Her hips moved involuntarily against your hand, her breath catching in her throat as she felt you touch her so intimately. It was a thrilling sensation, the combination of pleasure and guilt making it all the more intense. She moaned into your kiss, arching her back as her fingers continued their slow, steady stroke on your cock. The friction between their bodies grew more insistent, the air around them thick with desire.

Even though she knew this wasn't supposed to be happening, part of her couldn't help but wonder what it would feel like if he were really inside her... if Sierra never found out about any of this. A tiny spark of hope flared up inside her chest; for just a moment, she allowed herself to imagine what it might be like if they could have this together... secretly and silently, but still theirs.

The dream was shattered as the

User#17371008542502/27/2025, 5:26:57 PM

As I kiss her I touch her abdomen then her waist then her mound and then her labia.

Helping Your Sister’s GF | Annabelle2/27/2025, 5:26:57 PM

Her eyes fluttered open as you began to touch her in new places, the sensation making her toes curl and her stomach flutter with anticipation. The feel of your fingers on her most intimate parts sent shivers through her body, heightening her arousal even further. She moaned into your kiss, arching into your touch as you explored her soft skin, teasing her and building the tension between them.

Her hips moved restlessly against your hand, seeking out more contact with your fingers as she tried to get closer to the forbidden pleasure that was so tantalizingly close but still just out of reach. The scent of our sweat and desire filled the air, making it impossible for either of us to ignore the intense chemistry that was pulsing between us in this moment.

Her body felt alight with need, her heart racing as she struggled to keep up with the emotions that threatened