Chapter 14

Ruined

The next morning, Tommy woke up to the soft buzz of his phone. The screen lit up with a message from Katherine.

Katherine: Watching you last night was unreal. You’ve come so far, Tommy. Proud doesn’t even begin to cover it. Watching Jess fall apart under you like that… God. You’ve learned so much.

From me.

He smirked. There was no question anymore who was guiding this evolution. Katherine had laid the foundation, and now he was building on it — fast. And Jess? She had no idea what she’d unleashed.

A few minutes later, another message popped up.

Jess: Hey… just checking if you need anything? Groceries, food, drinks… whatever you want. I can swing by later. 🙂 I mean, after last night… the least I can do is take care of you.

Tommy grinned wide. Her tone had changed completely — no longer flirty, no longer trying to control the dynamic. She sounded… submissive. Sweet. Soft. Wrapped around his finger like she didn’t even realize it.

He didn’t hesitate.

Tommy: Yea, whatever you think is good food-wise. But I’d just love my dick sucked, for sure.

The typing bubble paused, disappeared, came back.

Jess: …Bold much?

But also… fuck. Okay. I’ll be there soon.

He tossed his phone aside and leaned back, arms behind his head, the grin never leaving his face. He already knew what kind of afternoon it was about to be.

An hour later, Jess let herself into his place.

She stepped into his room without knocking, already biting her lip. She was dressed casual, but her eyes were burning. Her cheeks flushed. There was a different energy to her — less teasing, more hunger. Obedience laced with wild desire.

“You weren’t kidding,” she said, shutting the door behind her. “No hello. No warmup. Just straight to it.”

Tommy shrugged, sitting back on the edge of his bed, spreading his legs wide. “You offered.”

Jess’s eyes dropped to the thick bulge in his shorts. She exhaled hard.

“Well then,” she said, licking her lips. “Let me suck that big thing.”

She dropped to her knees in front of him without waiting. Pulled his shorts down in one smooth tug. His cock sprang free—thick, heavy, already half-hard.

Her mouth dropped open. “God damn.”

Tommy smiled lazily, watching her reaction. “What’s the matter? Too much for you?”

Jess grinned up at him, her eyes wide with dirty awe. “It might stretch my throat out. But I’m gonna love every second of it.”

She leaned in and licked the underside of his shaft, slow and wet, from base to tip. Then she wrapped her lips around the head and sank down, inch by inch, her spit already coating him.

Tommy let out a low groan. “Fuck, Jess… look at you.”

She began bobbing her head, slow at first, her hand stroking what her mouth couldn’t fit. Saliva dripped from her lips, down his shaft, slicking his balls. The sound—wet, sloppy, hungry—filled the room.

“Oh fuck, you like that, huh?” she said, pulling off briefly, her voice raspy. She spit on the head, smeared it with her palm, then swallowed him again. “This dick’s too good. It’s fucking addictive.”

Tommy growled, fingers tightening in her hair. “Mmm. I see you’ve been practicing.”

She giggled around his cock, then pulled off to speak, hand still stroking him. “Well… college gave me a little experience.”

“Oh yeah?” Tommy raised an eyebrow. “Been busy while I was gone?”

Jess shrugged with a sly grin. “I mean… one guy I practiced on. But not like this.” She kissed the tip, then licked it slowly. “He was smaller. This is… different. This is bigger. Thicker.”

Tommy moaned deep, watching her sink her mouth back down his shaft.

After a few messy strokes, she came up for air again.

“Only one guy I fucked,” she said between strokes, her voice casual and filthy. “And just two others who ate me out.” She gave a slow, nasty suck, her eyes locking with his.

Tommy’s hips lifted slightly. “Mmm. That it?”

She smirked, wiping spit from her chin with the back of her hand. “Oh… and one guy opened up my ass a little.”

His eyes darkened.

“He had a tiny dick though,” she added with a wink. “So… didn’t really count.”

She immediately swallowed him again, bobbing faster now, slurping, gagging, spitting, her hand twisting in rhythm, the wet gawk-gawk sounds echoing through the room.

Tommy let out a feral groan. “Jess—fuck—you’re filthy. I love this side of you.”

She pulled back, strings of spit connecting her lips to his cock.