Page 33 of Let's Play Pretend


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“Push your ass out,” I say with a soft smack, making her gasp as I lay my throbbing shaft against the crease of her butt cheeks, moaning at the warm contact.

“W—wait,” she stutters, cocking her hips back so her butt cheeks wrap around my girth. “You’re really going to do this? Here?”

“Baby, when Daddy says he’s doing something, he’s doing it. My daughter should know that about me by now. Now, take a deep breath, this plug is coming out.”

My balls ache with the weight of the seed they’ve been producing since the moment I met her as I pull away from her warmth and press the button on the remote pen to deflate the plug. Then I reach over and squirt lube on my fingers and swirl it around her tight muscle and the stem of the plug.

“Oh God,” she mutters as I pull one of her butt cheeks toward her hip, exposing the black rubber device.

“Deep breath,” I repeat, as her body quivers and I twist the plug, making a slow exit so her tight virgin back door doesn’t clamp down. “Very good.”

The last of the plug slides out and I set it on the handkerchief I laid out on the table, then quickly reach down and lube up my dick as she exhales.

She turns her head and drags her tongue across her bottom lip. “Those people are looking.”

“So, wave.” I shrug as I line up the weeping tip of my swollen dick with her puckered entrance and tense my ass, applying forward pressure.

She hisses and cocks her head over her shoulder, her eyes filled with fear, but I guide her to face forward with a tug on her hair.

“Wave to them, baby. Wave to those people as I take your virgin asshole out here where everyone can see. Fucking dirty girl, letting Daddy do this to you. You make me hard because you know you want me to feel good, this is another way you’re going to do that for me from now on.”

With some hesitation, her hand releases the rail, fluttering upward in a halting wave. And to my thrill, as she gasps, the crown of my cock spreads her tight ring and the couple on the other side of the lawn wave back.

“Fuck,” I groan, laying down another soft smack on her ass, grabbing the base of my cock with one hand while holding her hip with the other. “So fucking tight.”

She’s breathing hard and her insides clamp down, practically biting off the tip of my dick as it battles to get inside her.

“No, no,” I say as I try to catch my breath and angle my hips to give her another soft push. “Relax. Count with me… One, two…”

A soft moan slips from her lips as she falls into the rhythm of the numbers with me.

“Three, four, five…”

Her ass softens, letting me slide the tip inside. She gasps as the ridge stretches her, then her body settles in again and I hold back any more forward motion for the moment.

“You’ve got Daddy’s dick inside you. You doing okay there, baby?”

She nods on a breathy hum. “My Daddy issues are sure coming in handy this weekend.”

“You’re doing great. I’m proud of you. Now, the next inch is yours. You push back and take what you can. But you have to take at least an inch. If you can do more, even better, but let’s start with an inch. I know it’s a lot, I’m a big boy, but I want to see you give it your best effort.”

She lets her chin fall to her chest as I reach up and encourage her, slipping my hand up her back and looping my fingers around her throat, urging her head back and up.

“I’ll try,” she says, the warmth of her body making my cock throb.

“Good girl. That’s all any Daddy can ask, for you to try your hardest.”

Tension tightens her body as her torso fills with a long breath and it’s as though I feel every micro movement and thought she has through the grip of her ass on my shaft. It’s all new for me, too. I’ve never wanted this from anyone before and have never indulged in more than relieving my base needs with my dick in a pussy over the years. After a few years in my twenties, I even drew the line at kissing. I didn’t like that contact. Too intimate. I’ve never tasted a pussy either until I tasted hers. In my own way, I’m full of virgin territory.

“Easy, baby.” I encourage as her body slips back, taking in another generous inch before Hannah winces and I stroke her neck with my fingers.

“So fucking good, baby. Ease up. Let Daddy just enjoy feeling you for a minute, warm and tight. How good does my dick feel up inside your dirty little hole, baby?”

She answers with another little backward thrust. “I can’t believe how good it feels. So good.”

“You want more?” I feel her body loosen and the sight of my dick entering her tight little hole makes me bite back the urge to rut into her like a madman.

“Uh huh. More.”

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