Page 41 of Watcher

“Are you sure about this?” he asks and opens the buttplug. I eyeball the six-inch toy that looks like a small, ribbed dick. There’s a blue button on the end. “Once I have it inside you, I’ll push the button. You’ll feel gentle vibrations. It’s not uncommon for a woman to have an orgasm during anal or anal play.”

“It sounds like you’ve taught anal before.”

“A few times,” he says. “Sure about this?”

I nod and crawl onto the bed.

12

Watcher

Iwait while Jessica crawls onto the bed, admiring her beautiful white ass. The bit of carpet she has matches the hair on her head. She lays on her stomach and looks back at me. She throws me a nervous smile.

“Is this right?” She shakes her ass at me, teasing a man who shouldn’t be teased. I wouldn’t go this slow with most women.

I lay the plug and lube on the nightstand and crawl beside her. I’d been with a lot of women since that summer a young woman changed me. Not once did I have the kind of feelings I have for Jess. This is going to go slow. Erotically slow.

Jess puts her hand around my cock and strokes. Our mouths come together, and my fingers find their way between her legs, her pussy already wet. She’s on her way to being ready. I brush her hair back over her shoulder and bury my face against her neck, fingers pumping into her wet slit.

Her moans are gentle and pleading. They grow as I move down her body, squeezing her nipples between fingers, releasing, and then squeezing again. She moans and drives her pussy down on my fingers. We were made for this. Here and now.

I continue down her body, leaving a wet trail from breasts to pussy. I feel her watching, waiting, anticipating when I might turn her over.

“You like teasing me,” she says. “What if I were to tease you?”

“You wouldn’t get very far,” I say. “Now turn over.” Jess turns onto her stomach and watches me grab the lube and plug. “Tuck your knees under your stomach. I need you sticking your cute little as out.”

“Yes, sir,” she says playfully. She tucks her knees beneath her stomach, resting her head on the bed, still watching me. “How’s that? And I wish it were little.”

“Better.” I run my hands over her ass cheeks and squeeze. Fucking delicious. “Ever had your asshole played with?”

“Never.” Jess’s smile is playful and a little shy. She watches me squeeze lube onto two fingers. “I’m excited,” she says in almost a whisper.

“I’m just going to massage you for a bit.” I give her a wink and run lubed fingers up and down between her cheeks, her puckered entrance tightening. “Relax, baby. Work on breathing and staying relaxed when I enter you with a finger. You tense up, and it’s going to hurt.”

“Okay. Watcher?”

“Yeah.”

“Thank you. For everything.”

I nod and move behind her, guiding a lubed finger over her entrance, pushing gently before pulling back. Pushing again. Pulling back again. Jess moans, controlling her breathing, careful not to gasp when my finger slips inside.

“Just a little for now,” I say. “You okay.”

“Yeah. It feels wonderful. Please don’t stop.”

“Didn’t think you would like it, did you?”

“Honestly, no.”

“Deeper. Okay?” I say. “A little bit of pressure.” I push deeper. “A little more. In and out, Jess.”

“Fuck that feels good, Watcher.”

“Call me Daddy, Jess.”

“Yes, sir, Daddy.”

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