Two Virginities

You knew it was coming. But then your mind caught up with the moment. "But didn't you just lose your virginity? Shouldn't you rest some more?" Her answer is immediate. "I have lube in my drawer. If you, you don't think it's disgusting, we could try... the other hole. I've always wanted to try anal." You are over the moon. "I'll be right back."

You don't think about getting dressed, as you quickly walk out of your room to Rebecca's. You go to the drawer at the bottom she describes, finding the lube, along with a few leather cuffs, and a bullet vibrator. Apparently this is her kinky drawer. You grab it and run out, not running into another soul. It would've been bad if Olivia had seen you running with an erection only somewhat softened by the speed that you move.

You open the lube, only to realize you've never done anal either. "Is this really ok? Won't I hurt you?" She smiles, as she looks towards you, the blindfold still in place. "I trust you. Just put a lot of lube on your cock, and my ass with a few fingers, and it should be fine. I've used a couple fingers before, so I shouldn't be excessively tight... I hope." Part of you worries, but you know that she'd only do this if she trusted you. A trust you hope to prove isn't wrong.

You take the lube onto your hand. You rub your fingers into the slick liquid and your fingers move toward Rebecca's ass, which she has lifted off of the bed as she moves toward doggy style. You worry about hurting her, but your masterful hands know what to do.

Your finger slowly pushes into her ass, one segment at a time. Once in, it begins to rub lube along her insides, twisting and folding inside of her, like it's painting every inch it can reach. As it fully reaches inside, you can feel her ass twitch on your fingers, **** for it. A second finger joins the first, and then a third, all while your fingers dance.

"Stop." Rebecca says this, panting, as you take your fingers out. You rub her back. She soon says the opposite of what you expect. "I want to cum on your cock, not your fingers. I want to pleasure you too." The masterful hands had almost pulled an orgasm from her, you always seem to underestimate them. Hopefully soon, you won't have to rely on them, instead using your own skills to make her cum.

You take the lube and rub your cock with it. You coat every inch liberally, before you move behind Rebecca. Your hand guides your hard cock to her anus. "I'm going to go slow, just like the first time. Tell me if you need me to stop." She nods.

You push inside of her, slowly pushing, until the head of your cock enters her. You stop as Rebecca speaks. "I can't take much more, please, may I cum?" You stop, sure that she was saying that this was a mistake, until your brain processed what she said. "Yes, cum for me." You say this as you slowly push inside of her. and soon it is followed by a response. As you fully embed yourself within her, you feel her ass clench around you, as she orgasms. Her panting only increases as she moans out, as her body shakes beneath you. You wait, unsure what to do.

As her breathing eases, she whispers, "Keep going, I want you to cum too." "Are you sure?" She nods, as you begin to move. She's tight, but not excessively so. Not as tight as you'd expect a normal ass to be. This is the ass of a woman who masturbates with it. Maybe that's where she puts her bullet vibrator...

You are moving slowly, thrusting, pulling almost all the way out before thrusting deep again. You expected some form of warning, some statement that you should go slower, but none come. Instead the words from Rebecca's mouth are all praise. "Oh god, you're so deep. I've pushed my fingers in so many times, but oh god." Her hips now go back to meet yours, as you begin to thrust a bit harder.

Your hands hold her hips, as you drive yourself into her quicker and quicker. But soon you feel them itch, or at least that's how you'd describe it. A latent desire, not pressing but like you should do it. Your hands let go of her hips, as before you realize it, one lands on her ass in a firm spank. You look at your hand in shock, as it rubs along the place it just struck.

You struggle with words, but Rebecca doesn't. "Ohhhh... I was just about to ask, but you've already done it. Please punish your buttslut, I'm a naughty girl." She can't help but moan as another spank lands on her other asscheek. You look at your hands. Did they sense the desire within her?

Your thrusts continue, deep, now at a normal pace. You'd never taken somebody's ass before, and the sensations are weird, as her asshole grips your cock. But there is also the dirty talk. Before, when you were fucking her pussy, Rebecca had sounded like many of your past girlfriends. Now she sounds like some whips and chains version of a girl you've known for many years. "I love how deep you are, how you claim me. I want to give you everything."

Your hands itch again, and you decide to let them do what they want. You are scared, as they reach down and take another tie from the bed. You are scared as they go back. They're not going to... **** her, are they? Your fears are allayed as your hands skillfully push the tie through a small hole in the back of her collar, lacing the tie through, before firmly pulling it back. It now functions like a leash. And Rebecca is ecstatic. "Yes, leash me, take me, make me your little slutkitten."

It feels like a long time, but it's only been a few minutes since you started fucking her. You feel your body grow hotter and hotter, your cock feeling amazing as your two bodies slam against one another. You know you can't last much longer.

"I'm going to cum." "I'm going to cum too, Master. Please, fill my ass with your cum. Please, let me cum with your warm cum." You grunt an assent, as you slam into her hips, pulling the leash tight as your cock spasms inside of her, filling her with your cum. As the first drops of your cum leave you, you feel her ass clench around you, as another orgasm rips through her. You both ascend the heady heights, as your orgasms roll through your bodies. The world grows white, as the two of you cling to each other in the storm of your passion.