RO Day 11 - Clean

In the back of your mind, you thought that you would be spending the day finding a way to ask Oliva out. Instead, she asked you out. Now she wants to… initiate you into things that you have not done before. She wants to pop your backdoor cherry.

Now you’re with her in the bedroom, damp and nude, smelling amazing with her body pressed tight against yours as you make out in the lamplight. You don’t need anal play, you just need to rub your hard, drooling cock up against her firm stomach a little more and you’ll be busting all over her.

She strokes your cheek and looks into your eyes.

“What do I do?” you ask.

She shows you the shopping bag, and what’s inside it. It’s a… gizmo. Obviously, it’s meant to go, you know, in there. It’s funny shaped, though. You are relieved to see that it’s not very big.

“It’s a prostate massager,” Olivia explains.

“Will it hurt?”

“I’ll be gentle. And I know how to make you brave,” she adds.

“How?” you ask.

“Put mine in me.” She shows you a… very different item. This is just a plug, but it’s huge. It’s bigger than your hard cock. Before you can ask her if she’s sure, she turns away from you and bends over… and keeps bending until she grabs her ankles. You are pretty flexible, but… Your cock jumps involuntarily, and precum dots the floor. You can see everything, including the way that her thighs are wet with her juices.

Well, she asked you to. You roll a condom onto the plug, slather it in lube, and position it.

“That’s it,” she ways, wiggling her hips encouragingly. “Put it in.”

You press gently, but gently won’t do it. It’s so big that you will have to really push, but she’s taking it.

“That’s it,” she repeats, but it’s more like a moan this time.

You give it some strength, and all at once, the plug disappears inside her. Her body jerks and she shudders.

“OK,” she gasps. “That’s more like it.”

Your mind is a little bit blown that she’s not only OK, but enjoying that, so wow.

She stands back up, shivering a bit. She blows out her breath and turns back to you, biting her lip and putting her hands on your shoulders. She looks into your eyes. Man, she is so excited. You have never seen her like this.

“You ready?” she asks.

“Not for that,” you squeak.

“Just for the massager,” she says, stroking your hair.

“And you’re going to be gentle?”

“So gentle,” she assures you.

“OK,” you say, sounding very wimpy.

“Oh, baby.” She pulls you into a hug and kisses your cheek. “You don’t have to if you don’t want to. I just think because you have a dick you are going to really…” she trails off, giving you this look. “I think you’ll be into it.”

“I’m down,” you say quickly. You can’t pussy out. That is not an option.

“Baby, you have to relax.” She pushes you to the bed, but then she moves past you to lie down. “Come on.” She says, gesturing with both hands. She wants you to climb on top of her? You do that, and she guides you until you are straddling her chest. It’s a weird, not unpleasant, but weird feeling to be basically sitting on her boobs, but she wants your cock in her mouth.

You let her have it, and she sucks hungrily, her fingers finding your ass.

“Relax,” she mumbles around your cock, her fingertip probing your asshole.

Easier said than done. It feels so good! Your body is tense, and you don’t know how to change that. You groan and gasp as she sucks you, simultaneously fingering you back there. There was no way you were going to be holding out. Rather than letting you go, Olivia clamps her lips around you as you whimper, gushing in her mouth. She gulps and swallows, pushing harder with her finger. It’s inside you now, and your whole lower half is on pins and needles.

“Ah,” you gasp as you get past the peak.

Olivia gulps it down, then comes up for air. “That’s it,” she asks. Her finger is literally inside you. “Here, come on.” She touches your side, guiding your torso down. You lean down, supporting yourself on your hands. You’re on all fours.

“Stay like that,” she says, slipping out from under you as you gasp for breath.