Page 99 of Entering Stronghold


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But yeah... she really, really wanted to do it with Adam.

Time to bargain her ass out of jail.

Adam

This kind of foreplay was utter torment. Of course, keeping Angel caged up behind the bars was as fun as it was frustrating. Especially the expressions crossing her face as she slid back and forth between trying to role play and being amused. Granted, role play wasn’t always his favorite thing in the world, but it was fun on occasion. And he was enjoying bargaining Angel down to entry into that luscious ass of hers.

Seeing her glance at the door to the jail again, he wondered if she was going to make a break for it. If so, he’d know she wasn’t ready to do that with him yet. Although, of course, she could always say her safe word too, but he had a feeling Angel would rather make a jail break than say her safe word. Most submissives got a sense of pride out of never having to say it, and a good Dom never pushed so far that his submissive should feel the need to.

Angel licked her lips, dragging her teeth over the plump lower one, and he suddenly knew what her decision was going to be.

Those bright eyes almost glowed as she started unsnapping the straps of her outfit. Holy shit. If he’d known how easy it was to take that thing off of her, he would have ripped the damn, teasing thing off of her before shoving her in the jail. Although at that point she might not have made it in.

His cock was pulsing behind his zipper as he watched her little strip tease, her body swaying gently back and forth to the music which was always in the background, although he didn’t think she realized she was doing so. The straps fell easily away to crumple onto the floor below her, leaving her completely naked except for those bright red heels on her feet... and separated from him by the bars.

Adam’s arms tensed as he forced himself to remain still.

“You got something you want to offer, sweetheart?”

“Yes Sheriff,” she said, cupping her breasts and pinching her nipples, which were already hard. At least he knew he wasn’t the only one turned on. “Sounds to me like you need a good, tight ass for that cock of yours.”

He had to stifle a groan as electricity seemed to shoot straight through his body. Angel was going to offer up her ass to him. Even though she’d marked it as something she had experience in on her survey, he knew it was still something that, for most women, required extra trust. A bit of extra intimacy beyond what regular sex needed.

Standing up, he went over to the door of the jail, keeping his eye on Angel as she trotted over to the entrance.

“Alright sweetheart, come on out, bend over my desk and show me what you have to offer.”

She purposefully rubbed herself against him as she exited the jail, smiling happily although he could see she was nervous too. That little thrill of anticipation, of anxiety in her eyes with a hint of fear, was like an aphrodisiac for him. There was nothing sexier than a submissive who was aroused, excited, and apprehensive all at the same time.

Then Angel bent over the desk, resting her arms on its surface and exposing every inch of her gorgeous pussy. The heels she was wearing put her ass at the perfect height for him. Between the mounds of her ass cheeks, her tight, dusky little hole winked at him and Adam could feel his blood surging down to his cock. It was amazing he had enough running through the rest of him to keep his body moving.

Walking over to the desk, he opened the top drawer where he knew the lube was kept. Angel’s head was turned slightly, watching his every move. He winked at her and moved back around so he was directly behind her.

Crouching down, he kissed the inside of her thigh, smiling a bit at her gasp of surprise. Working his way up her inner thighs, he eventually reached the wet heaven of her pussy. She was moving her hips up and down slightly, her legs spread far enough that he had easy access to her pink inner lips. Her little clit was poking out of its hood, swollen and eager. Adam flicked his tongue over it and enjoyed the way she moaned in response.

Lubing up his fingers, he continued to lick and suck on her pussy lips, getting her even more aroused. When he pressed one wet fingertip to the entrance of her asshole, circling it a little bit to tease the nerves, Angel groaned and pushed back against him. Damn that was hot. She obviously was more than ready to have something inside of her ass.

Obliging her, he sank his finger deep into her without any further ado. The taut ring of muscle at her entrance clenched down around him as he teased her clit with his tongue. Angel moaned, moving her hips with his finger as he began to slide it back and forth in her tight hole, loosening her up a little bit. When he added a second finger she gasped and shuddered a little bit. He could feel the strain in her body as she adjusted, and he realized she probably hadn’t had anal sex in very long time.

Which only made his cock ache even more than it already was.

He sucked her clit into his mouth and felt the tremor shake her entire body. Fuck. Releasing her from his lips, he ignored her mewl of disappointment as he stood.

“Uh uh, sweetheart, you’re not going to cum until I’m deep in that hot ass.”

She whimpered again as her ass clenched around his fingers. Yeah, she liked that idea. Watching his fingers slickly gliding in and out of her ass, the tiny hole shiny with lube, he used his other hand to undo the front of his pants. There was something incredibly hot to him about taking Angel’s ass for the first time while she was completely naked but for her fire engine heels and he was fully clothed.

Her tight little hole gaped slightly when he pulled his fingers out, giving him enough time to spread some lube over the length of his cock, line it up to her hot entrance and begin to press in.

Fuck.

Both of them gasped at the same time as the head of his cock was sucked into her, her body spasming around the intrusion. Adam rubbed her lower back soothingly, stopping his progression and giving her time to adjust to his cock, it was a hell of a lot thicker than his fingers. She had let her upper body slump onto the desk, her head turned to the side and her cheek pressed against the wood. He could see the fluttering of her lashes and her parted lips as she panted through the discomfort.

Watching her endure the discomfort, the slight flashes of pain, all for him was both humbling and wildly arousing. It was one of the biggest reasons anal sex was such a turn on for him. He loved watching the struggle, knowing she was doing so to please him, and it was going to eventually bring both of them incredible pleasure.

Angel

The stretch burned... fuck... she hadn’t considered Adam’s cock was a good bit thicker than anyone she’d ever had anal sex with. But it felt so good too. Toys didn’t do the same thing. They were hard, more unyielding and they didn’t pulse and throb inside of her the way he did. Angel moaned as he receded a bit then pushed in deeper.

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