Lorelei tried on her bridesmaid dress when she got home from the rehearsal dinner. She wanted to make sure that it was okay before bringing it to the hotel tomorrow morning to get ready.

Jesse was sitting on her bed watching her. She twirled in the dress, watching the material billow out around her feet. Jesse smiled as he watched her do multiple poses in the full-length mirror in her room.

"You look beautiful," he said.

"You think so?" Lorelei asked. "I never usually wear pink."

"You look good in it."

Lorelei giggled as she crawled on top of Jesse so that she was straddling his lap. She couldn't spread her legs too far apart because of the dress. Jesse ran his hands up her sides as he kissed her.

"I want to rip that dress off you," he said.

"Molly would be pissed if we ripped this before the wedding," she said.

"So take it off carefully," he said. "So that I can rip off your underwear."

"I'm not wearing a bra."

"Even better."

Lorelei lifted her hair above her head and turned her back to Jesse. He pulled the zipper down and she slipped out of the dress. She hung it back up on the hanger before turning to face Jesse. She was surprised to see that he was not staring at her anymore but instead going through his backpack.

"I got you something," he said.

Lorelei grabbed a shirt off of the floor and threw it over her head. She sat on the end of the bed next to Jesse. He pulled a small box out of the bag. He opened up the top to reveal a silver chain. It reminded Lorelei of the ones that she saw Jody and Lexi wearing around their necks. She clutched at her pounding heart as she looked up at Jesse.

"I know we never talked about collars," he said. "And you don't have to wear it if you don't want to."

"You bought this for me?" Lorelei asked.

"Yes," he said. "I would love it if you wore it."

Lorelei smiled as she threw her arms around Jesse's neck. She could hear Jesse sigh with relief as he wrapped her up in a hug.

Lorelei turned and lifted the back of her hair up. Jesse fastened the chain around her neck. She let go of her hair as she turned back around. The chain was tight against her throat, but not uncomfortable. It was like the chokers she used to wear in high school when her Dad said she was "going through a phase."

"Thank you," Lorelei said.

She brought her fingers up so that she could touch it. She was happy to take a reminder of Jesse everywhere she goes. It did not dangle, so she was excited that she could even wear it to work. He grabbed her fingers that were fiddling with it and kissed the back of her hand.

"I'm glad you like it," he said.

His smile turned into a smirk, and Lorelei knew that his mind was wandering as he stared at her bare legs.

"Lie down on the bed," he said.

She nodded and without saying a word laid down on the bed. Jesse went through his backpack before looking up at Lorelei.

"You've been very open," Jesse said. "You haven't told me about anything that scares you yet."

"Scares me?" she asked with a nervous giggle.

"Yes," he said. "What have you always wanted to try, but it makes you nervous?"

Lorelei sucked in her bottom lip as she thought. She had tried so many new things with Jesse, but there was always one thing that was on her mind. She blushed as she thought about it.

"Tell me what it is, baby girl," he said, sensing her hesitation.

"Anal," she said.

Jesse's smirk returned as he held something out in his hand. Lorelei sat and then picked it up to examine it. It was a piece of metal that was almost cone-shaped. The end was a red jewel. Lorelei raised a brow as she looked at him.

"What is this?" she asked.

"It's a butt plug," he said.

"Excuse me?" Her eyes went wide. "This is going to go in my ass?"

"Only if you want it to."

"Isn't that going to hurt?"

He took the plug out of her hand. He held it up so that it was between them.

"It's going to hurt a bit," he said. "But if you want to get your ass ready for my cock then you're going to want to use it."

Lorelei let out a shaky breath. Jesse reached out and put his hand on her knee.

"It's okay to be nervous," he said. "We don't have to do anything you don't want to do."

"I want to do it," she said.

"Turn around then."

Lorelei turned so that she was on her hands and knees. She arched her back so that her ass was in the air. Jesse hooked his fingers around the waistband of her thong and pulled it down. She could already feel her sex growing wet at the thought of what he was going to do.

She jumped when something cold touched her ass.

"Relax," Jesse said. "It's just lube. Never stick anything in your ass without lubrication."

Lorelei nodded, unable to speak. His fingers spread the lube over her asshole.

Her fingers curled into the sheets when she felt the tip of the plug. She squeezed her eyes and tensed as she felt the plug enter her ass.

"Lorelei, you need to relax," Jesse said.

She let out a deep breath she tried to relax her muscles. Her fingers stayed curled in the sheets in front of her body.

Jesse slowly worked the plug in and out of her ass. She bit down on her lip to stop herself from crying out as she felt her ass stretch. He pushed it forward, and the pain disappeared.

Strange did not even begin to describe how she felt. The sensation was odd in her ass and she squirmed as she tried to get comfortable with the feeling. Jesse put his hand on her ass and rubbed her cheek.

"How does it feel?" he asked.

"Weird," she said. "Like, really weird."

"Try to keep it in for a little bit."

Lorelei pushed herself up so that she was on her knees. She hissed as she felt the plug shift. She was afraid to sit down, worry that it would hurt her again.

"Have you ever done this before?" Lorelei asked.

"Put a butt plug in a girl?" He asked.

"No, had something up your ass?"

Jesse shook his head as he laughed.

"No," he said. "I have not."

"I don't think this is fair then," she said.

"Want me to take it out?"

Lorelei shifted her hips as she continued to try and get used to the feeling. It was an odd sensation, but she wanted to get used to it. Her thighs clenched at thought of Jesse fucking her ass one day.

"Let's keep it in for a bit," she said.

"Good girl," he said. He reached for his belt and began to unbuckle it. "How about you get on your knees in front of me?"

Lorelei smiled and nodded. She moved carefully as she got down onto her knees. Jesse ran his fingers through her hair before continuing to undo his belt.