The Beautiful Mistake Pt. 05

"It's hot as fuck in here," she says before taking a long drink.

"Good for the muscles," I reply, "keeps everything relaxed."

She hands me the water and I drink, feeling the cold travel all the way down my throat and into my stomach.

"You ready?" I ask her as she takes another sip.

"I don't know. I'm suddenly nervous."

"That's alright. It's good to be nervous. Nervous can be fun. You know me, I'm going to take my sweet time."

"Patience."

"Exactly. You listen to me, trust me, all will be well. And if for some reason it's not, just say the word and the lesson is over."

She stares into my eyes, a last verification of trust.

"Ok."

"Alright then," I say as I reach under the bed and pull out the massage table's matching wedge pillow. "Lay down on your belly again, with this under your hips."

She does as she's told. With the wedge, her ass sticks up into the air, the cheeks separated to reveal her tight, pink, hairless anus. How my cock is every going to fit in there?

I drop my pants, becoming fully naked. I grab the oil and dose her ass liberally. I begin to message her cheeks slowly, but deeply. My thumbs move from the under curve of the cheeks to a millimeter away from the opening again and again. I spend a long time massaging, sometimes going back to her thighs. I want to return her to a state of total relaxation.

When the moment finally feels right, I take the pad of my right thumb and place it on her anus. Just a touch, nothing more. She lets out a small coo and I see muscles tighten from her lower back to thighs.

"Breathe," I tell her. "Relax."

I pour oil down her crack to my thumb, which I begin to tenderly swirl around her ring. With my left thumb, I lightly stroke her clit. I continue this way until I see all the tension leave her and hear those subtle shifts in her breathing and moaning that lets me know she fully accepts what is happening. I press my right thumb a little harder, making slight contact with the inside of her. So far, so good. I press ever-so-much harder and the tip of my thumb begins to enter her. Her breathing seizes up for a moment, but then begins again, still relaxed, still accepting.

"Shall I?" I ask.

"Oh, yeah. I know I can handle this."

I stop playing with her clit with my left to grab the oil bottle. After pouring more oil on it, I push my right thumb further and pop it inside her to the first knuckle.

"All the way," she says, "It's better all the way."

I push the whole length of my thumb inside.

"Ooooh God..." she moans as I begin to slide my thumb back and forth. I put my index finger into her vagina. Then between the two digits, one in the anus the other in the vagina, I softly squeeze the septum that divides them.

"Oh wow!" she responds.

The movements of my thumb become ever-easier as the flesh surrounding it relaxes and the opening expands.

"I guess I don't have to be that patient," I say to her. "I believe you're ready."

"I think I am."

Removing my thumb causes her to let out a groan. I climb up on the table behind her, onto my knees. I cover my cock with oil.

"Push your ass farther back," I tell her and she follows suit. Her cheeks spread wider. I grab both cheeks, place my thumbs on either side of her anus and push away from it, opening it. It's still such a tiny hole and my cock has rarely been so engorged. Here goes nothing.

I grab my cock and bring the head to her. Just like with my thumb, I begin by simply touching it. Again, I see marks of tension in her back, but they are less than before. I rub my head against her star as I watch the tension fade from her body. Then I slowly, steadily begin to push in. At first, the resistance seems too much and that entering her this way is impossible. But then, with a pop, suddenly my whole head is inside her.

"Oh! Oh!" she gasps, suddenly nervous once more.

"Don't worry," I tell her, pouring more oil down her crack and onto my cock. "You're doing beautifully."

I place my hands on her ass cheeks and spread them farther apart. My cock slides in deeper still. The pressure around my cock is almost overwhelming.

"Oh my god, oh my god, oh my god," she says, tearing up. "It's so much bigger than anything I- I ever- Oh..."

"We can always stop."

"No! No. Just- just keep going slow."

I push a touch deeper, then pull back a smidge. I push a touch deeper still, then pull back again. I continue on this way at a deliberate pace. But in time, I find my whole shaft buried deep within her. The pressure is so intense I have to use every bit of self-control I have to stop myself from coming deep in her ass right now.

"How are we doing?" I ask her, my cock stationary within her.

She can't really form words, but the sounds she manages seem positive.

"I'm going to make my strokes a little longer, a little faster."

She grunts in assent.

I take her hand and guide it to her clit.

"You take care of that, alright?"

She begins to rub herself.

"Good girl."

My strokes become longer and at a more regular tempo. I want nothing more than for her to come from this experience, but I've never felt anything this tight before and I fear I might burst at any moment. Apparently she wants to make sure she comes too, as she is frantically rubbing her own clit like a woman possessed.

"You wanna come?" I shout at her.

"Yes!"

"You wanna come with me in your ass?"

"YES!"

"Then fucking DO IT!" I scream and slap her ass hard.

That does it for her. She comes, sobbing.

And just in time. I pull out of her just before a massive load explodes from out of my meatus. The cum sprays her ass and back, both of which are so oiled, the pearls slide off of her as soon as they touch her. I look down and witness the gaping hole that was once so astonishingly tight.

I climb off the table and crotch down so my face is level with hers. Her cheeks and forehead are glowing red and covered in droplets of sweat. Her eyeliner runs in streaks down her face. Her eyes are wide as though she's just survived a perilous ordeal.

We stare at each other in silence for a long while until, at last, she speaks.

"Best. Lesson. Ever."