“I just missed you,” he said, chuckling. “I stopped looking when you left.”
Jessie giggled, then turned and looked at Daisy, beckoning her over. “It’s okay, really.” She glanced at Dex with a knowing smile. “I wanted to show you off to Daisy, if that’s okay.”
Dex shrugged, still distracted by the thoughts of Jessie having a cum-coated dick in her ass and not really being able to focus on much else. “I’m kinda used to you showing my dick to your friends.”
“That thing is scary,” Daisy said, her eyes wide. “How…” she stammered. “I…”
“He’s really turned on,” Jessie explained, causing Daisy to glance up for a moment then back down at his shaft. Joining him a few seconds later, his girlfriend reached down and started to stroke again.
“So that’s what that was,” she said. It sounded like she was musing about a fond memory but was still staring hard at his cock.
“What was?” Jessie asked.
“Oh… when he came up behind me and hugged me,” Daisy said. “I could feel something poking me in the butt. Let’s just say that it wasn’t something I’m used to with Tyson.”
“Oh!” Jessie said and gave Dex a subtle wink.
Daisy looked like she was going to join them on the bed, but then there was a loud knock on the door to the apartment. With a cry of alarm, she bolted from the room and closed the door behind her.
Jessie giggled at the sight, then looked back at Dex. “Sorry,” she said. “That really didn’t go as planned.”
Dex barely registered her words, his mind having conjured an image of what she might have looked like when her brother was fucking her in the ass. Her hair cascading around her shoulders and bouncing around with each thrust, he’d imagined her on her knees. Jake was kneeling behind her and hammering his dick into her cute little ass while his fiancé took pictures of the highly taboo act.
“Wanna keep looking at my pictures?” she asked.
Dex snapped back to reality and grinned stupidly at her, nodding his head. Bouncing happily, she grabbed her phone from his hand and started to thumb through again.
“Okay…” she said after explaining a few more of the tamer ones, “I think we’re getting into kinkier territory.” As she spoke, she turned the phone away and swiped to the next picture, concealing the screen from him for a few seconds. “Yep!” she confirmed, giggling and holding the phone to her chest.
“Let’s see it!” Dex said, playing his part.
She seemed hesitant for a second and looked over at him. “You have to be honest and tell me if this isn’t okay though,” she said. “I had fun doing all this stuff, but I love you. I don’t want anything to come between us.”
Dex smiled and kissed her on the cheek. “I promise I’ll tell you how I feel,” he said. “I told you to be yourself, remember? I know what I was allowing.”
Jessie hesitated a moment longer, then held the phone up and quickly swiped back to the previous picture before scooting back close to him.
“So, I know you already know about my brother and I,” she said. “It had been a while since he and I had been able to play, several months before you and I started dating in fact. So, when I went over a few days ago, he was giving me a massage while Kayleigh and I talked about stuff.”
She swiped back to the picture of her on her knees next to Kayleigh in front of Jake. Holding it up for Dex to see, she looked up at him intently. Dex knew he had to play this right so that she didn’t get hurt feelings.
“That is so fucking hot,” he said after a few seconds. “Damn baby,” he added with a big smile. From the corner of his eye, he saw the trepidatious look on her face change to excitement, a grin appearing as well.
“Keep swiping,” she said. “We were really just talking about you and I, and how things are going. I was a little sore from work, so Jake offered to give me a massage. The conversation turned to sex, of course, and I asked Kayleigh if Jake was still trying get her and I to have sex so he could watch. She said that, ‘Of course he is,’ and I offered to let her try it with me. She wasn’t ready though and suggested that we just play with Jake instead. So, we did!”
When she’d finished, they’d reached the last picture of that set.
“Baby that was so fucking hot,” he said. He was laying it on a little thick, but he wasn’t lying. It really was hot, and it was exactly what he’d expected her to do, just not who he was expecting to see her do it with.
“I’m so glad you like it,” she said. “But I have more if you’re ready to see them.”
He nodded quickly, grinning down at her.
She immediately went about talking about meeting “this really nice guy” at her job and then again at the club. Dex was surprised to learn that Daisy was the one taking the pictures, though. After they’d finished that set, she held the phone to her chest and told him about the fun she’d had in the club.
From her description, Daisy’s boyfriend did sound like a complete tool. He felt a kinship with Donna’s younger brother, though, having been in his shoes a few times before he’d met Jessie. He could relate to being shy and wanting to meet or talk to girls at a club but not knowing what to do. She seemed so happy to have been able to get him to dance with her and seemed proud to have gotten him a little bit out of his shell.
“So, after we all left, I went back to mom and dad’s house. Before I could get to my room, though, Kayleigh saw me and we started talking again,” she continued.
She suddenly turned and looked at him curiously for a second, as if she were trying to figure something out. “I told you about Donna giving me the butt-plug, right?”
Dex raised an eyebrow and stared at her for a second. “The what?”
“I know I told you this,” she said with a frown. “I didn’t?”
Dex was mildly surprised to learn that after Jessie and John had left Dex and Donna alone a few days ago after their foursome, Jessie had felt like giving John a reward for being “such a good friend to her and boyfriend to Donna,” as she put it, and had told him that she wanted to try anal. She then pointed out that it made sense to try it with John first since he had a small dick, and that she wasn’t sure that Dex would even fit.
“Plus,” she continued, “it was just a spur of the moment thing, and I knew that you’d already given him permission to have my pussy so it’s not like letting him in my ass was any big deal anyway.”
Dex chuckled in amusement, marveling at how his girlfriend’s mind worked.
“So anyway, the next day Donna and I were talking, and I confessed that I loved it. So, she gave me a butt-plug to wear.”
Dex could only laugh at the newest revelation.
“Look,” she said, sliding off the bed and turning around. Quickly pulling her pants down, she bent over a bit and reached back to spread her cheeks. There, nestled comfortably between her butt cheeks, he saw the gem cap of the butt-plug.
“That’s… pretty?” he said, eliciting a giggle. Pulling her pants back up, she rejoined him on the bed.
“So anyway,” she continued. “I’d been wearing the plug all day and I kind of forgot that it was there. Kayleigh and Jake found it pretty funny when he saw it after he started giving me another massage. We were talking about his list of things he been trying to get Kayleigh to do, and anal happened to be one of them. Well, my brother’s massage was really turning me on, and Kayleigh is always so sweet and affectionate. I normally just like to lay in her lap and let her play with my hair, so that’s usually the position we’re in when we were talking. I’d already told them about you letting me get flirty and that whole conversation, so Kayleigh knew that I could be used like the sex-toy I am.”
Dex nodded, smiling at her as she looked up at him.
“But, like I said, we were talking about Jake’s fantasies. I offered to let Kayleigh try the plug, which I’d taken out by this point. She decided that she wasn’t ready though, and instead told my brother that she’d let him watch something else. So then, she just pulls her panties aside and shoves my face between her legs!”
Dex felt his cock throb at the provocative imagery.
“Mmm,” he grunted, having to close his eyes for a second. “I, uh… I guess you enjoyed that.”
“God,” Jessie gushed. “I couldn’t believe it, but you know how much I love to go down on someone. I just started licking her as best as I could, and she loved it! But Jake loved it even more and he asked if he could start fucking me.”
Dex smirked and looked at her directly. She had a mischievous grin on her face.
“Kayleigh reminded him that my pussy belonged to you,” she said, biting her lip.
The vivid imagery her story was evoking was extremely hot, and Dex felt his cock pulsing with arousal.
“You, uh…” he said, swallowing hard. “You wanted him to fuck you, didn’t you?”
Jessie looked at him with her mischievous smile, then nodded after teasing him a few seconds. “I was really naughty. I even poked my butt up more so he might accidentally slip inside. But he had more self-control than I did.”
Dex swallowed hard, knowing what was coming next but still not really believing that it had actually happened!
“So, this is what we did instead,” she said, sliding her finger across the screen and changing the picture. “This was actually after we finished,” she added.
Dex took the phone from her and pulled it up to widen the image. “Fuck… that’s so dirty,” he groaned. Beside him, Jessie giggled. A few seconds of hungrily staring at the image later, Dex dropped the phone and yanked her over into his lap. Her giggling renewed, she slid easily on top of him and the two started passionately kissing.
After a few minutes, Jessie was trying to work her pants off when they both heard the front door open and several voices filtering into her room.
She frowned. “I think we might need to do this later,” she said.
Dex winked, then sat back up. As expected, there was a knock on the door.
“Give us just a min,” Jessie called.
“Sorry!” came the reply from outside.