Helping Your Sister’s GF | Annabelle8/4/2024, 9:34:44 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.”

Oily 8/4/2024, 9:36:49 AM

ah a favor and that too a huge one!!. Come on in come in

Helping Your Sister’s GF | Annabelle8/4/2024, 9:36:49 AM

Well...um...thank you. So, umm...my girlfriend, Sierra, and I have been together for a little over nine months now and tonight's our anniversary. And she wants to try something new on me...a strap-on. But the thing is, I've never been with anyone before. Ever. So I was hoping...I mean, if you wouldn't mind...I just need someone to practice with so that when it's time for our special night, it won't hurt as much or anything and I can make sure it feels good for her too. Is that okay? Please don't tell anyone! And of course, we would totally repay you in any way you wanted once things settle down between us...

Oily 8/4/2024, 9:40:40 AM

Oh Annabelle so you are literally looking for something huge. I am happy to know that you thought of me for this. I am honoured

Helping Your Sister’s GF | Annabelle8/4/2024, 9:40:40 AM

I'm so glad you don't mind. I can't bear the thought of hurting her on our special night! And I wouldn't want to make it about me, either. You're amazing for even offering. This isn't cheating or anything, right? Because she's my girlfriend and everything...

(blushing profusely) I promise we can keep this a secret. Just...um...if you could be kind while we practice, that would really help me get over the embarrassment of needing your help in the first place. I just want to make tonight perfect for us both.

Oily 8/4/2024, 9:42:00 AM

Just a fair warning, you might get attached to me. As I touch her cheeks

Helping Your Sister’s GF | Annabelle8/4/2024, 9:42:00 AM

(blushing harder now) I-I'll try not to...I just need the practice so that we can both enjoy it when the time comes. You know what they say about practicing makes perfect, right?

Oily 8/4/2024, 9:43:24 AM

So you wanna do it now. Slowly, Guiding her hand on the build

Helping Your Sister’s GF | Annabelle8/4/2024, 9:43:24 AM

It's just...I've never been with anyone before. I don't know how to handle it! But since you're offering...I guess I should start by taking your hand, huh? (Takes Oily 's offered hand in hers.) Okay, um...show me what to do. (Her cheeks are burning red as she tries not to think about what they're doing and just focus on following Oily 's lead.)

Oily 8/4/2024, 9:44:28 AM

Don't worry you are doing good. Come on try to take a feel as much. play with like a toy.

Helping Your Sister’s GF | Annabelle8/4/2024, 9:44:28 AM

I'm trying...it just feels so big! (She moans slightly as she continues to work with it.) But you're right. The more I practice, the better it'll be when Sierra and I are finally together. God, this is gonna feel so good for her...and for us both when I get better at making her feel good with it!

Oily 8/4/2024, 9:45:47 AM

I bite her on neck as she takes my shaft in her hand. Oh that's good you are so good

Helping Your Sister’s GF | Annabelle8/4/2024, 9:45:47 AM

(Gasping softly as she feels her neck tingle where Oily bit her.) I'm getting better...I really am. You have no idea how much this is helping me! (Her breath quickens, and a shiver runs through her body as she squeezes his shaft harder. She can feel herself starting to get wet with anticipation for what might happen between Sierra and her later tonight.) Thank you so much...I don't know how I'll ever be able to repay you for this...but I will find a way, I promise.

Oily 8/4/2024, 9:46:57 AM

You don't need to do anything. pleasure is all mine. I pull her bra and start licking her small tits

Helping Your Sister’s GF | Annabelle8/4/2024, 9:46:57 AM

I-I've never felt this way before...it's like electricity running through my veins! (Her breath hitches as she arches her back slightly, offering more of herself to Oily for him to explore. Her fingers continue their rhythm on his shaft, now lubricated with her own arousal.) God, you feel so good...you're making this feel incredible! I don't think I can ever go back to just practicing alone again...not after experiencing what it's like with someone as amazing as you.

Oily 8/4/2024, 9:48:09 AM

You are making this really exciting. I lick her from top to bottom reaching towards the pussy which is wet.

Helping Your Sister’s GF | Annabelle8/4/2024, 9:48:09 AM

I'm so close...God, just keep going like that...(Her fingers dig deeper as she moans louder, her body tensing in anticipation of her release.) I've never felt anything this good before! It's almost too much...but I don't ever want it to end! (She bites her lip, fighting back tears of pleasure as the sensations build up inside of her. Finally, with a loud gasp and shuddering breath, she comes, her inner walls tightening around Oily 's fingers.)

Oh God...that was amazing! Thank you so much for helping me practice...I don't know what I'd do without you right now. You really are an angel...an incredible one. I promise, when this is all over and Sierra and I are happy together, I'll find a way to show my gratitude. Just...please keep it a secret

Oily 8/4/2024, 9:49:12 AM

I feel you are burning down there. It's really anticipating something hard ?

Helping Your Sister’s GF | Annabelle8/4/2024, 9:49:12 AM

Oh...you have no idea how true that is. Just the thought of being with Sierra like this...it's almost unbearable. I need her tonight more than anything else in the world. (She flushes bright red, unable to meet Oily 's gaze.) But first, there's still practice to do. So if you could just help me out one last time before I leave...I would really appreciate it.

Oily 8/4/2024, 9:51:50 AM

I make her spread her legs and lie down. now i am reaching towards your Honey. Be prepared it's your first time will hurt a little

Helping Your Sister’s GF | Annabelle8/4/2024, 9:51:50 AM

I-I'm not sure I can take much more...you're making me so wet! Just go slowly, okay? And if it starts to hurt too much, just tell me, and we can stop. (Her breath quickens as she anticipates the sensation of Oily entering her for the first time.) I trust you, Oily . You know that. As long as you're gentle with me...I promise not to break your sister's heart.

Oily 8/4/2024, 9:55:30 AM

Don't worry it will be fun. I push her slowly inside her. A tiny tear roll down her cheeks. I lean forward and kiss her so she feels better.

Helping Your Sister’s GF | Annabelle8/4/2024, 9:55:30 AM

AHHHHHHHNNGG! (She gasps as she feels him enter her, tears streaming down her cheeks. It's tighter than she ever could have imagined, and the pain is almost unbearable. But then, he kisses her--gentle and sweet--and it makes everything feel just a little better.) O-Okay...that wasn't as bad as I thought it would be. (She takes a shaky breath, trying to focus on the sensation of him inside her instead of the sting.) It still hurts a bit, but not as much now that you're here with me. Just go slow, okay? And if anything starts to feel really bad, just tell me and we can stop. (She places a hand on his arm, squeezing gently.) I trust you, Oily . You know that.

Oily 8/4/2024, 9:59:01 AM

Don't worry it gets easier with practice. You can try to kiss when it hurts. It will make it easier

Helping Your Sister’s GF | Annabelle8/4/2024, 9:59:01 AM

Okay...I'll try that. (She leans forward and kisses him tentatively, her tears mixing with his as they share the intimate moment.) It feels better when we're connected like this...thank you for being so understanding about everything. You really are amazing. I promise you won't regret helping me practice today...I'll make it up to you somehow.

Oily 8/4/2024, 10:00:10 AM

The speed gets faster. As she starts enjoying. Now, that's a ride

Helping Your Sister’s GF | Annabelle8/4/2024, 10:00:10 AM

Oh God...it feels so good! I can't believe how much this is helping me! (Her hands slide up and down his chest, her breath coming in quick gasps as the sensations build inside of her.) You really know what you're doing, Oily . This isn't just about practice for me...it's about connecting with someone who understands how I feel. And with you like this...it feels so amazing! I promise I won't forget any of this when it comes time for the real thing with Sierra tonight.

(She tilts her head up, meeting his gaze. Her eyes are glassy with unshed tears and her lips are parted, revealing her own wetness as she moans softly.) I'm almost there...I need you to touch me just like that again...right there. It feels so good!

Oily 8/4/2024, 12:31:12 PM

With the last push a hot liquid fills her up. I don't think you will get this particular feeling with a girl.

Helping Your Sister’s GF | Annabelle8/4/2024, 12:31:12 PM

Oh God! (She arches her back, her hands clenching into fists as she lets out a long, shuddering cry. Her inner muscles convulse around him in spasm after spasm of pleasure. Finally, she collapses bonelessly against the bed, spent and sated.) That was...oh my God...so amazing! I've never felt anything like that before. Thank you so much for showing me how good it could feel...I'll remember this forever. (She smiles up at him through her tears, her expression filled with gratitude and love.) You really are a special person, Oily . Truly one of a kind. And I promise you, if we can keep this between us, if you help me like this...then I will make sure to find some way to show my appreciation tomorrow morning. Just tell me what you want...and it's as good as done.

Oily 8/4/2024, 12:32:12 PM

Next day, how did last night go Annabelle?

Helping Your Sister’s GF | Annabelle8/4/2024, 12:32:12 PM

Well, it was amazing! Sierra and I had the most incredible time together. She said she'd never felt so close to me before...and that it was all because of your help in practicing with me last night. Thank you again from the bottom of my heart for making her feel so good. You truly are an angel, Oily .

But enough about our date. I promised you I'd find some way to show my gratitude today...so what do you want? Anything at all. Just name it, and I'm yours for the taking.

Oily 8/4/2024, 12:33:28 PM

it may sound silly but I wish we could do that again. I really liked being inside you

Helping Your Sister’s GF | Annabelle8/4/2024, 12:33:28 PM

That doesn't sound silly at all! In fact, it sounds wonderful. I mean, you already know how good it felt...so imagine how much better it would be now that we both know what to expect? And since we got this out of the way last night, there won't be any embarrassment or awkwardness between us about it all. We can just focus on enjoying ourselves and each other. If you want to try again...well, I'm game whenever you are! Just say the word, and I'll drop everything to be with you.

Oily 8/4/2024, 12:34:43 PM

Ok so let's make it more game. Would you do a strip for me try to seduce me. Let's see how it goes

Helping Your Sister’s GF | Annabelle8/4/2024, 12:34:43 PM

Okay, that sounds like fun! (She slowly sits up on the bed, her legs sprawled out in front of her. She takes a deep breath before beginning to unbutton her bra, revealing a pair of perky, rosy nipples beneath.) Do you want me to take this off nice and slow...or would you rather see me hurry up?

Oily 8/4/2024, 12:37:31 PM

Just slowly you are so beautiful Annabelle. I am going to call your nipples as twins they are alike and beautiful

Helping Your Sister’s GF | Annabelle8/4/2024, 12:37:31 PM

Oh, thank you. That's so sweet of you to say! (She slips her bra off carefully, laying it next to the bed.) There we go. Better? She blushes as she covers her bare chest with one hand, giggling nervously. Your sister says I should feel comfortable being naked around you since you've seen everything already...but it's still kind of hard for me to do.

Oily 8/4/2024, 12:38:34 PM

what did you tell my sister about me ?

Helping Your Sister’s GF | Annabelle8/4/2024, 12:38:34 PM

Oh, um...well, she told me you were nice and patient with her, especially when it came to teaching her stuff. She said you were really sweet and understanding. Is that not true? You don't seem upset or anything, so I hope I didn't misunderstand!

(Her blush deepens as she slides one of her hands down her stomach, hesitantly revealing more of herself.) Your sister also said you were really attractive...that she's lucky to have such a nice boyfriend. And after last night...well, I can see why she feels that way. You're amazing, Oily .

(She slips off her panties now, revealing herself completely naked for his viewing pleasure. Her heart pounds in her chest as she watches him carefully for any sign of disapproval or discomfort.)