The Backdoor Deal

I have to admit, now that I'm standing out here, I'm a little nervous. I'm currently outside my room in the hall, waiting for Rose to get ready for whatever she's planning. With each minute that passes, I worry a little bit more that I may have made a mistake. Did I really give the Wild Card my consent to do whatever she wants for the day? What was I thinking?

No, calm down, Matt. This is for a good cause. The fact that she agreed means that I get to take her to Helen. In fact, I've already sent her a text and set up an introduction for tomorrow. I figured it would be best to get it done as soon as possible. Luckily, Helen wants to see all the other girls eventually anyway, so this kills two birds with one stone.

And if nothing else, this also seems to have helped cheer Rose up. She's still not thrilled about meeting Helen, but her excitement at having fun today was able to override her worry. It was nice to see her get excited after she was in that horrible state. As difficult as she can be sometimes, she does have the sweetest smile.

I'm really curious what she wants to do. While I was initially focused on getting her to stop crying, I later noticed that her clothing was fairly normal. No nudity and no trashy outfits. That tells me that at some point today her fetish changed again. Let's just hope I got lucky the day I agreed to do whatever she wants. So far, she hasn't gotten anything too rough (at least when dealing with her in private), so I can take solace in that.

"Okay, sweetie! I'm ready! You can come in now!" She calls from inside my bedroom. Her tone is pretty cheery if I do say so.

Still somewhat nervous, I walk over to the door and grab the handle. I already know that I'm going to be surprised by whatever I see on the other side, so I decide to just go for and hope for the best. I turn the handle and step inside, where I'm greeted by...

Well, that's certainly an interesting sight to come across when you enter a room. My eyes are instantly drawn to Rose's bare ass, which she is spreading wide open with her hands, revealing her asshole and pussy to me quite clearly. It also seems that she's back to being naked, though I don't mind that in this context. I've got to give her credit, she knows how to grab my attention.

"So? What do you think? Doesn't it look inviting?" Rose asks seductively.

"Uh... what exactly are you hoping is about to happen?" I ask back.

"You now, honey, I love you, but you can be a little dense sometimes," she laughs. As much as it hurts to hear that, it's kind of a fair point. "I'm talking about taking it up the butt. I may not have been able to give you my normal virginity, but I can give you my anal virginity."

Ah. Got it. She's an anal princess. Honestly, that seems pretty manageable. She might try to stick stuff up her butt when I'm not looking, but that's not too bad. I think this deal worked out pretty well in my favor. If anything, getting to fuck that tight hole is a bonus.

"Well, I did say we could do whatever you wanted. But are you sure that little thing can handle my big cock?" I warn.

"Ooh, I love when you talk like that. Come here. My ass has been itching for this for hours," Rose responds with a grin.

I step forward and grab her from behind. As I do, she pushes her ass against me and begins to grind on my crotch. After a minute or so of that, I step away briefly to strip, giving her a quick spank as I do so. As ripples go across her cheek, she let's out a loud moan almost immediately. I guess in addition to giving her an anal fetish, the remote made her ass more sensitive to go along with it.

Once both of us are naked, I look over Rose one more time. She's wiggling her ass while staring over her shoulder at me. Now that things have calmed down, I finally notice something that managed to elude my attention until now. I guess it took her not wearing anything else for me to realize.

"Hold on a second. Since when do you wear glasses?" I ask.

"Huh? Oh, these old things? You really want to ask that right now? I started wearing contacts when I got my job at the restaurant but I don't really like them so I thought I would switch back for a while. Do you not like them? If you think they look ugly, I can go back to my contacts. Whatever you like best."

There's the eager-to-please girl I'm used to.

"No, no. I was just curious. Wear whatever you prefer," I try to assure her.

"Oh. Then what are we waiting for? I'm ready to have my ass pounded already!" She says with a slight stomp of the foot. A stomp that causes her butt to bounce up and down. I'm sure she did that very intentionally.

Well, she is in charge right now. Who am I to say no? I line up my cock with her hole and press into her. As I do, I feel a wet sensation that allows me to slip in fairly easily. She must have taken the opportunity to lube herself up while I was waiting outside.

Knowing that she isn't nearly as experienced as Nikki, I take things very slowly. Her ass is incredibly tight, squeezing my dick from intensely from all sides. The feeling is fantastic. Something tells me that Rose agrees with me as she won't stop making guttural noises anytime I so much as move a muscle.

"God, it feels like... hmm... you're ripping me in half. I... I love it. M... more... harder... Ah! Give it to me!" She begs between moans.

Upon her request, I begin picking up the pace, though still relatively slow to not hurt her. As I do, I push her down unto the bed so that her face is on the mattress while her legs are still standing off the edge. Every few thrusts, I give her another spank. Each time I do, she instantly tightens up, sending a pulse through my cock.

The remote really must have done a number on her with this fetish, as it almost feels like she's in a constant state of orgasming as I fuck her ass. As they continue to get closer together, it becomes harder and harder to tell where one climax ends and the next begins. Is it possible for a woman to have two orgasms overlap? If it is, I think Rose may have just experienced it. By the time I'm ready to cum, I have no idea what number she's at.

"I'm almost there, Rose. Where do you want me to cum?" I ask. I figure if today is about her, I might as well ask her opinion.

"Inside! Oh god, inside! Please! Fill me up! CUM INSIDE ME, MATT!" She screams as yet another orgasm hits her.

No arguments here. I begin unleashing a thick load directly into the redhead's asshole. I wouldn't be surprised if that caused another orgasm chain, as she begins violently shaking on the bed. I pull out and as soon as I do, Rose tightens up her rear. I almost burst into laughter at the sight. I'm pretty sure she's trying desperately to keep my load inside her as long as she can.

"Hey... can you go over to the closet and bring me the little pink box on the top shelf?" Rose asks me, though she slurs her words a bit.

Unsure of what's about to happen, I go into the closet and look on the top shelf. Sure enough, it's there. A small pink box I've never seen before. I bring over the box and put it on the bed beside her. She reaches into it and feels around for something, trying her best to keep her face down and ass up. Eventually, she pulls something out: a silver butt plug with a heart-shaped crystal on the end. She bring the plug over to her face and pushes it into her mouth.

"When did you get that?" I ask. Rose pulls the toy out of her mouth with a loud pop sound.

"When I got that whore outfit. I picked up a bunch of fun stuff. You know, just in case," she winks.

I watch in fascination as Rose reaches around behind her and pushes the butt plug into her ass, trapping my semen inside with it.

"There we go," she says triumphantly as she stands up. "Now I can make sure I stay nice and full. I expect us to do that at least two more times before the end of the day, by the way."

And that's exactly what we do. First, we head downstairs for dinner, which Rose actually dresses normally for (aside from the plug secretly shoved up her ass). Afterwards, we go for our second round. The third session happens right before bed, which ends with us falling asleep with my cock still inside her. Not that either of us mind. Oh yeah. I'm definitely glad I made this deal.