A couple of weeks passed by, Kelsey coming over three more times for D&D sessions. The fourth time was a Friday night and she and Bran holed up in his room as normal. The session ended early, at 10:00 and Brandon and Kelsey sat and talked. Bran was at his desk in front of his computer, Kelsey on his bed, sitting cross legged, wearing a t-shirt and knee length skirt. As they talked, Brandon’s attention drifted to trying to see up her skirt whenever she shifted, but not making it obvious.
“So, did you have a boyfriend you left behind when you moved here, Kelsey?”
“Not really. I dated a few guys, but I mostly had online relationships. I’m not doing either one right now.”
“Online relationships?”
“Yeah, we’d video chat and do like sexting stuff and watch either other get off.”
Brandon felt his face flush at her plain words. “Oh. I guess I didn’t realize that was really a thing.”
“Yeah, I’m a little shy with new people, but the online stuff makes me more confident, I guess. And speaking of… could I see your dick?”
“What?!”
“It’s no big deal. I like looking at them. I’ll show you my boobs.”
Brandon dropped his voice to a whisper. “My mom’s right outside watching TV.”
“You and I both know she’s asleep by now.”
Brandon tip toed out in the hall and peeked into the living room, seeing the form of his mother, laying down on the couch. He couldn’t see if her eyes were closed or not, so when he came back to his room, he closed his door most of the way, leaving it open 6 inches or so.
“You’re serious? You really want to see my dick?”
“Yeah, let’s see it.”
“And you’ll show me your boobs?”
“Yep.”
Brandon nervously glanced at his door, then stood up and unbuttoned his jeans, unzipping them, pulling them down to his hips and pulling his cock out. It was half erect as his nervousness warred with his arousal.
Kelsey leaned forward. “Ooh, you have a nice one. You should trim your pubes, though. It will make everything look… neater. And bigger. Not that you’re small. You’re not at all.” She continued to peer at it, watching it grow as Brandon stood there in front of her. “It really is a great dick, Brandon.”
“You think so? Really?”
“I like it a lot. Okay, time for me to pay up!” She lifted her t-shirt up, exposing her braless breasts. “I know they’re not very big, but I’m actually a c-cup.”
Brandon stared in surprise at seeing her with no bra. Her breasts were not what anyone would consider large, but she was right in that her cup size wasn’t small. They weren’t exactly conical, he thought, but they were maybe umbrella shaped? In any event, they didn’t sag at all. Her nipples were small and her areolae were puffy and pink. They were totally unlike his mother’s boobs and he was fascinated. He caught himself as almost told her they were ‘neat.’ He would have died of embarrassment. “Wow, they’re really great, Kelsey. I like them.”
“Wanna watch each other get off, Brandon?”
Brandon whispered fiercely, “But my mom!”
“She’s asleep. Let’s do it.”
“Gosh. Um… okay. Do I just sit here in my chair?”
“That would work great. Take your shirt off too for me.”
Brandon, feeling shy, felt his fingers tremble as he peeled off his shirt, pants and underwear, sitting in his computer chair wearing only socks.
“For God’s sake. Take your socks off, Brandon.”
He complied, watching her intently. She removed her shirt all the way, then sat on the edge of the bed, wearing only her skirt and spread her legs. She slowly moved her skirt up to expose her panties and rubbed her crotch through the green material, nodding as Brandon took his cock in hand.
“You can use lotion or whatever you normally use to jerk off.”
Brandon grabbed bottle of lotion from a desk drawer and squirted it in his hand, smearing it all over cock. He watched Kelsey bite her lower lip and pull her panties to the side, exposing a shaved bald pussy, the inner labia barely visible.
“Wow, you shave! My mo…” Brandon caught himself before he said something crazy about his mom’s hairy bush and stammered, interrupting himself. “My mouth is watering looking at that pretty pussy, Kelsey.”
“Ooh, dirty talk. I wasn’t sure you had it in you. That’s important for this. I love watching you jack that big cock, Brandon.” Kelsey lifted her ass off the bed and removed her panties, hiking her skirt up to her waist and pulling her knees up so Brandon had a good view of her clean and neat looking pussy. He couldn’t help but compare it to his mother’s, which was so different with the big dangling labia, the dark bushy hair that promised musky wet pleasures. Kelsey’s was sexy in a different way. Unspoiled, maybe virginal. Young. He stroked long and slow as he tried to come up with some talk that didn’t sound dorky.
“I’m imagining plunging my tongue deep in that pretty pussy. Licking you up and down, tasting you, smelling you…”
Kelsey’s eyes were half closed as she watched Brandon jack off and listened to his words, which were a turn on for her. She had been tracing circles around her clit and moved her hand to slide her middle finger deep inside her wet pussy, moving it in and out. “Your cock looks so fucking delicious. I’ve never given anyone a blowjob, but I want your cock in my mouth, sliding that hard beauty past my lips inch by slow inch.”
Brandon became unsure if they were role playing or if she really wanted to suck him off. He started to stand with a questioning look on his face. Kelsey shook her head and gestured for him to sit back down. He did so, feeling his face turn red that he misunderstood. He gave her an awkward thumbs up, then got back into the role play. “God, I’d love to be in that hot fucking mouth of yours, watching you take me deep, feeling your tongue work my cock head until I explode hot cream into your mouth.”
Kelsey had two fingers in her snatch now, producing soft squelching sounds as she watched Brandon stroke himself. “Play with your balls for me, Brandon. And don’t think I don’t see your eyes drifting down to my tight little asshole, you dirty boy. I’d love to lay you down on this bed, sit on your face, and make you tongue fuck my stink hole until I creamed all over your chin.” She removed her fingers from her pussy, reached behind her leg, and lightly rubbed her juices over her sphincter, watching Brandon closely. He moaned softly when she touched her asshole, and she smiled to herself at finding a hot button.