Pretty smoothly, all things considered

Jen wanted to be present, to make sure that Jack didn't hurt her daughter, but Emery refused, assuring her that things were going to alright. Reluctantly, the mother let her daughter step into the third room with Jack, and no one else was allowed in.

Emery awkwardly started stripping, until she noticed that Jack was just sitting on the bed, not doing anything. "Um, you too, Jack."

Jack looked at her, with her shirt hiked up over her bra, and woke from his depressed thoughts. "Yeah, sorry, Em." He stripped quickly, unbuttoning his shirt and then slipping his underwear off along with his pants.

Emery blushed, staring at his flaccid penis with wide eyes. After a brief pause, she continued removing her clothes while Jack politely looked the other way. When she was down to just her plain bra and cute pink panties, complete with a cartoonish, black cat face stamped on the butt, she stopped undressing and moved onto the bed, behind Jack.

Jack turned around and saw her hesitant face, her hands drawn up, covering her white bra. She stared at him, and without saying anything, willed him to take the initiative. Jack crawled toward her across the bed and held her hands while looking into her wide, blue eyes.

"You ready?"

She nodded. "Mm."

"Have you done it before?"

She shook her head. "Unh-uh."

"Is it okay if I make it wet first? It should hurt less."

Emery blushed. She'd only touched herself a handful of times, and she'd never shown herself to another person. After a brief pause, she nodded.

Jack ignored her bra and went straight for her panties, removing them without even looking at the design on the back. She covered herself with her hands, but he gently pried them away, revealing her smooth slit. Her blonde pubes were thin and short, but Jack wasn't sure if that was because she was just eighteen, or if it meant that she shaved them every once in a while.

"Try to relax," he said, as he spread her slit and licked her. The taste was salty, and slightly acidic, a bit stronger than Anne's had been. Jack closed his eyes and focused on eating out the girl in front of him, toying with her clit and gently pushing inside of her with his tongue.

Emery moaned quietly and ruffled Jack's hair with her hands, overwhelmed by the sensations she was experiencing for the first time. She thought he would stop after she got wet, but he kept going, harder and harder, even using his fingers to stimulate her near her entrance, until she felt her first orgasm nearing.

"Stop," she cried out between moans, "Too much!"

She squirted on his face, surprising him with a powerful spray of sexual fluids, while clamping down on his head to keep him there as she came. The fluid covered his face and even went up his nose, but he continued to swirl around her clit with his tongue, helping her to ride out the pleasure.

After a minute of squealing and jerking her body, Emery finally went limp and released her grip around Jack's head. She hardly noticed as he got up and went to the wall, pulling out a small towel that he used to dry himself. When she realized what she'd done, she blushed again. "Oh my god, I'm so sorry!"

Jack put the towel down on the nightstand. "Don't worry about it."

Emery frowned, very worried about it. "Umm."

"Seriously. You're cute, Em." Jack tried to get her to relax for what was coming next.

Emery blushed harder and covered her face with her hands.

He lined himself up with her, until his hard cock hovered only an inch away from her exposed pussy. "Do you want to take this off first? You don't have to if you don't want to." Jack reached around to unhook her bra, waiting for her to answer before moving further.

"Um, okay," she said quietly, letting him unhook it and take it off, but quickly putting her hands back over her face. The sides of her boobs peeked out underneath her arms.

Jack thought for a second, making sure that they were both ready. "Should I use a condom?"

Emery peeked out from between her fingers. Her blue eyes were once again wide, and afraid. "You need points too," she squeaked out.

Jack nodded. "I guess so. But are you using any birth control?"

Emery nodded back, still hiding her face. "Yes. I started taking the pill on the first day, just in case. I just finished my period, too, so, um… it should be safe…"

"Alright." Jack touched the tip of his dick to her entrance. "I'm putting it in, then."

She tried to say okay, but her voice caught in her throat. She nodded and made a small noise instead. "Mm."

"I'll be gentle," Jack assured her, as he pushed himself into her wet folds. He didn't feel any significant resistance inside her, but he saw Emery twitch in pain, and move her hands to grab at the sheets above her, as he bottomed out. "Does it hurt?"

She nodded. "Mm."

"Want me to pull out?"

She shook her head. "Unh-uh."

Jack smiled at her. "Okay, Em. Let's take it slow."

He moved slowly inside her, a gentle in-and-out, until she stopped gripping the sheets so tightly. After a few minutes, he picked up the pace, and Emery wrapped her hands around his back, unable to stop her voice.

"J-Jack! It feels good!"

He put one hand on the back of her head, holding her against his shoulder while softly kissing the nape of her neck. The other hand, he held against her waist as he thrusted harder and faster, grinding his crotch against hers to stimulate her clit.

When he felt himself getting close, he focused and slowed down, switching his hand from her waist to her clit, and gently sliding his fingers over it while he pounded against her. A few more minutes of slow rocking, as he quickened the pace of his fingers against her clit, and Emery began to tremble, clenching down on him intermittently.

She called out Jack's name, stuttering, before gasping and moaning loudly, reaching her second orgasm with his cock still thrusting in and out of her tightening pussy. Her clenching brought Jack over the edge, and he let out a soft groan as he released inside of her, his dick pushed as deep as it could reach.

They held each other for a few breathless minutes, recovering from their shared orgasm, before he let her go and pulled out, dripping a string of cum onto the sheets. He grabbed a tissue from the nightstand to clean up, and offered her another for herself.

"Thanks," Emery blushed, taking the tissue and shifting her hips away from him. She could barely feel her legs.

"That should do it for the points," Jack noted, sitting up against the headboard. "Do you want to shower first, Em, or should I?"

"Um." Em's cheeks grew even redder. "Would it be alright if we, um, cuddled, for a little while? And then maybe we could… shower together?"

Jack was silent for a few seconds, looking away. "Sure," he said finally, pulling the comforter out from underneath them, and then settling in against her. She quickly wrapped herself around him and rested her head on his chest. Jack ran a hand through her neat, blonde hair and she hummed happily.

Em knew that she couldn't replace Anne for Jack, but she appreciated how kind both he and Anne had been to her, and she wanted to cheer him up. She didn't know how she would go about making him happy again, but she enjoyed listening to the thump of his heartbeat against her ear and having his gentle fingers play with her hair. For now, basking in the afterglow of her first time, she felt that just holding him was good enough.

A while later, before their time was up, they got up and went to the shower together. In the third room, the bathroom was more spacious, using Tim's excess funds to purchase a large bathtub in addition to a wide shower, but at least for now, the tub was left unused. Em tried to see if Jack would go for another round with her in the shower, turning around and showing him her nice, tight ass, but, although his cock reacted, he didn't make a move on her, instead reaching for a bottle of soap and washing her back for her, perhaps spending a bit more time than absolutely necessary massaging her butt cheeks.

When they got out, Jack dried off and let his erection soften on its own, tugging on his pants and rebuttoning his shirt. Em was a little disappointed that her advances were so easily and casually refused, but when Jack smiled at her on the way out of the room, her heart fluttered, and she beamed in return.