Page 206 of Entering Stronghold

“What’s that?” she asked, pointing at his hand. “I mean, I kind of know what it is because I recognize the bag, but what exactly is in it?” The look on her face was one of eager anticipation. He should have realized she’d recognize the black bag with its distinctive gold bars since she’d been there earlier in the week to get clothes.

Still, that only added to the anticipation. Rick grinned. “Let’s sit down and I’ll show you.”

Except when they got to the couch, Rick sat and then grabbed her hand, easily pulling her over his lap while she was off balance and teetering slightly in those devilish heels. They looked like they could do serious damage to a man’s back and Rick wondered if he’d let her leave them on later and risk it. Although if he tied her legs down then he could still enjoy the visual effect...

He shook himself slightly, bringing himself back to the matter at hand as Maria twisted slightly to glare up at him. “What are you doing?”

“Showing you what’s in the bag,” he replied cheerfully, pushing the skirt further up to expose her bottom. She was wearing a cute little black thong, the thin fabric bisecting her ass cheeks perfectly. Too bad it was going to have to go. He pulled it down and off of her legs, leaving her bottom half completely exposed. Even though she was muttering under her breath, he could see how turned on she was already. Letting his fingers drift up her inner thighs and to her pussy, he used his other hand to pull a small bottle out of the bag. Massaging her pussy, just above her clit, he flipped open the cap and expertly let a few drops of fluid slide out onto his finger.

Dropping the bottle onto the couch, he brought his wet finger down to rest on the crinkled little star of her anus. Maria jumped slightly, one of her hands wrapping around his ankle to grip it tightly.

“What are you doing?” She looked up at him again, this time her face slightly more worried.

“I want you to wear a couple of things for me tonight when we go to Stronghold,” Rick said, massaging both her clit and her anus at the same time, watching her pupils dilate as her body registered the pleasure. “I’ve got a small plug, a very small plug, for your ass... do you think you can handle that?” He pushed his finger in, just slightly, and smiled as she moaned.

Her body hung over his lap, her head going back down towards the ground as he manipulated those two small bundles of nerves. If she’d never done any kind of anal play before then she was probably struggling a bit with the new sensation of pleasure in an area she’d never experienced before. Deciding he’d spread enough lube around it, he pushed his finger in again slightly, feeling the tight grip of her muscle clench down around it.

“Relax sweetheart, open up for me... I promise it’s going to feel good.”

A little feminine whimper came from down near the floor, and then he felt her body relax slightly. Using tiny increments, Rick pushed his finger in and out, continuing to stroke her pussy with his other hand so she was becoming more and more aroused as he played with her tight little virgin asshole. Even though she wasn’t saying anything, he could tell she liked it, because her pussy was becoming soaking wet. His dick was hard as a rock, pressed against her side, but he knew he wasn’t going to be getting any real satisfaction for at least a couple of hours.

However, he was going to have the satisfaction of tormenting her and he could be happy with that.

Eventually he worked his entire finger into the hot, tight vise of her ass. She squirmed on his lap, her breathing heavy, as he fucked her with his finger. Damn, she’d liked this way more than he’d expected... one day Maria was definitely going to give up her ass to him. Not tonight, maybe not any time soon, but eventually it was going to happen.

This was so strange and so wrong and so hot. Maria hadn’t really thought she’d like anything anal. Sure, she’d been kind of curious, especially after the frank talk she’d had with the other girls in the locker room during her first visit to Stronghold, but she really hadn’t expected to actually like it. Rick’s finger felt invasive, like it wasn’t supposed to be there, but also good. It stretched her in a way she hadn’t experienced before, drawing a surprising response from her pussy. While she could probably blame some of that on the way he was stroking her wet folds and clit, she knew at least part of it was from the way he was fingering her ass.

The nice thing about being over his lap was that it took away some of her embarrassment. She didn’t have to face him or see him while he gently probed a hole she’d always thought of as a big N-O. All she had to do was let him take control of her body while she drowned in the sensations.

When his finger slid out, she actually whimpered a little and he chuckled.

“I knew you’d like that.”

The things he knew about her body always surprised her, cuz she definitely hadn’t known she’d like it. Then again, he just knew a lot more things than her period. There was a sound like plastic splitting apart and then a couple of seconds later something cool and wet nudged against her anus. Maria groaned as it pushed it, much faster than Rick had done with his finger, stretching open the tight hole and making her shiver as the cool toy entered her.

“That’s it sweetheart, just relax.”

It felt huge, even though she knew it probably wasn’t. Maria clenched a bit and then felt her muscles relax. They burned slightly as Rick pushed it all of the way inside her, until it felt like there was a slight pop and her sphincter closed around the base. She could feel the flat part that was outside of her, in between her cheeks, and she clenched again, this time experimentally. It felt... surprisingly good.

“Good girl. There’s one more thing I want you to wear for me tonight.”

Panties. He was slipping panties up her legs. Maria scowled. She’d put on a hot little thong, just for him, and he was having her wear real panties? Sighing a little bit, she didn’t protest as he settled them into place. There must be a reason.

One which she found out as soon as he pushed her back up to a standing position and she felt something firm and nubby settle against her clit. “Oh!”

Eyes glinting with appreciation, Rick stood. With her dress still up around her waist it was easy for him to cup the mound of her pussy, pressing whatever was in the panties more firmly against the sensitive little nub.

“Feel that sweetheart?”

Maria clung to dark blue shirt he was wearing, nodding her head. “What is it?”

“Something for later.”

Frustratingly, he wouldn’t say anything else. He just led her down to his car—which was an experience in and of itself. The plug felt like it was jostling around inside of her and she automatically clenched to keep it from falling out, making walking even more difficult in her high heels. Now she knew why Angel had been walking weird last weekend. It felt so full and strange, but also exciting in a darkly sensual kind of way. The hard bump at the front of her panties rubbed against her clit with every movement she made; sexual distraction at its worst.

Then Rick started the car.

Maria felt every bump, every turn, every divot in a way she’d never experienced before. She tried to keep up her conversation with Rick, but she was all too aware she wasn’t tracking all of the time. The sensations were just too distracting. Sitting on the plug wasn’t exactly comfortable, but at the same time the discomfort just turned her on even more. She had to sit with her legs slightly apart, despite the super short skirt, or put too much pressure on the panties over her clit. Added on to all of that, was Rick’s hand on her bare thigh, his fingers gently caressing her skin. She’d put her hand on top of his, but that didn’t stop the tiny sweeping movements of his fingers.

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