Venus School of Sex Ch. 04

***

Justin had thoroughly had enjoyed watching Jessica's slow turn from fear to a sexual awakening of her deepest, darkest desires. Her delightful ass was meant to take a cock, and often. The way it had gripped his fingers, her insides convulsing around them, trying to suck him further into her body, had told him everything he'd needed to know about what a fantastic ride she was going to be.

Now he just enjoyed her complete submission to him. He couldn't wait for her first BDSM class, she was a natural submissive and he was going to thoroughly enjoy showing her all the pleasures that he could give her. But that was for later, at the moment he focused on the pleasant feel of her asshole rippling around him as he continued to play with her body. Her steady breathing with the occasional hitches told him that she was enjoying it to.

"Do you know what a butt plug is, Miss Swift?" he asked, although he was loathe to part his fingers from her body.

"Yes," she responded back, so quiet he almost didn't hear her.

"I'm going to put one in you now. It's going to stretch you just a little more than my fingers are, and it might not be completely comfortable at first - like my finger wasn't, but it won't hurt and it's going to help keep you stretched and flexible. You need to keep it in at least for lunch time, and if you can keep it in for longer that's good but at the very least just until the end of lunch."

"Ok," her voice was rather muffled. She sounded hesitant, anxious, but not scared, and her ass was still relaxed, she wasn't clenching her cheeks at all. That was good.

Reluctantly he pulled his fingers from her grasping body. "Stay right here," he told her, "I'm going to go get the plug."

Every student got a new plug, and they'd be able to take it home with them at the end of school. He chose a medium sized one, she'd be able to handle it and it would help her out more in the end.

Returning, he found that she had done exactly as he told her to, and she was resting with her eyes closed. He caressed her butt cheek gently and her eyes flew open. Grinning down at her reassuringly he showed the plug. Her eyes got a little big but she didn't protest.

Kneeling down behind her again he spread lubricant over the entire length of the plug, and for good measure spread some more on his fingers and pressed them back into her ass. Her hole had closed up a little, but not much, and she moaned and lifted her hips a bit as he pushed his fingers back in. Yes, he thought to himself happily, Jessica was going to be quite the slut for anal sex by the time he was done with her. He let his fingers slide in and out of her accommodating hole before pulled them out entirely and pressed the tip of the plug to her.

***

Jessica felt completely wrung out, and a little anxious about the size of the plug that Mr. Flood seemed so excited about forcing into her tight crevice, but the thought did turn her on, and she could see that it wasn't quite as big around as a dick, so she should get used to the idea now. She was glad that it wasn't quite as girthy as a dick, now that she knew a little more about anal she wanted to feel a bit of a stretch when he took her cherry. And she was glad that she would have the same teacher for each of these classes this week, after all the wonderful sensations he'd made her feel today, she trusted Mr. Flood to make the popping of her anal cherry very erotic and very pleasurable.

His fingers quested deep inside her again, and despite her exhaustion she felt the stirrings of arousal deep in her belly as he plunged back into her depths. In fact, if he wanted to take her anal cherry right now, she'd probably just lay here and take it... and enjoy it. But after a few thrusts of his fingers he pulled them out and she felt something cool and hard at the entrance to her back door.

Slowly he began to work it in and out, it wasn't as flexible as his fingers but it wasn't so hard it was painful either. She did whimper a little as her ass began to stretch, the widest part of the plug was definitely thicker than his fingers. It felt good and slightly uncomfortable as her tight hole opened much wider than it was accustomed to, like an itch that hurt to scratch but felt satisfying too. He worked the plug back and forth, letting her hole get acquainted with the wider part before sliding back to the narrow, and then back up to the wider, pushing a little bit more of it into her body each time.

Finally her ass closed over the largest part and she let out a little cry as the plug settled snugly into its new home. Her ass clenched around it, and she panted as she tried to get used to the sensation of this hard object inside of her. Mr. Flood massaged her thighs and butt cheeks as she clenched her ass over and over... part of her wanted to expel it, but the widest portion wasn't leaving her body without help right now. After a few minutes of massaging and her ass grappling with the plug, it settled in and she was able to relax.

Mr. Flood helped her to her feet, and the plug moved inside of her. Although her skirt was covering her ass again, she couldn't help the flush that spread across the face as the plug shifted inside her with every movement. There was no forgetting that it was there.

"Thank you very much," she said, moving her weight from foot to foot as the plug twisted and jolted her insides a bit. She was having trouble concentrating.

"My pleasure," he responded. "I look forward to our next class tomorrow."

"Me too... ah," she glanced at the erection that was threatening to split open his pants. "Can I... would you like me to..."

Glancing down he saw the object of her intent. "No Jessica," he smiled his amusement. "Have you taken the Basic Intercourse class yet?" She nodded, not realizing that he'd memorized her class schedule and knew that she had, and had already talked to Mr. Winter about how it had gone. He leaned forward, his face warm against hers as he whispered in her ear. "Remember, anticipation makes consummation all the sweeter."