Emmie Does Anal

Smiling back at her, Mark brought her legs up to his shoulders and saw her eyes widen in surprise. Grasping his cock, he finally removed his fingers from her virgin asshole and pressed the tip to the slightly gaping rosebud.

"Mark! NO! Wait!"

"Shhh... you're keeping your virginity, Emmie. You're getting everything you want... now it's my turn." He groaned as he pushed inward, the tightness of her asshole fighting him. "Just relax, it won't hurt as much."

The look of fear and strange anticipation on her face was almost too much for him to bear. Then her features screwed up and a few tears leaked from her eyes as the head of his cock forced its way past her grasping sphincter. Putting his hands on her hips to hold her firmly in place beneath him, Mark groaned and paused for a moment to enjoy the sensation of her virgin asshole having been broken in and the way it was clenching around the crown of his dick. It was like being held in the tightest vise imaginable, so tight that he was almost worried she'd cut off circulation to the tip of his dick.

Then he pressed down on her hips and pushed in deeper, groaning again as she whimpered. Not wanting to be unkind, he began to rock his hips back and forth, getting her used to just the little bit of cock that was deflowering her asshole.

"Mark, Mark, please nooo... it hurts... oooo... it's burning... You're too big, I can't take it!"

Even as Emmie thrashed her head back and forth, she wondered if she really wanted him to stop. She was begging him, but she wasn't fighting, she wasn't trying to dislodge the burning rod from her dark hole. It did hurt, his penis was far too big, and yet she found that she was still tingling from her orgasm.

"Shhh, you're doing such a good job Emmie... fuck your ass is so tight... just try to relax, I'm going to loosen you up and then I'm going to fuck this tight little ass so hard..."

Tears slipped down her cheeks as Mark slid deeper inside of her, her clenching anus no match for his lubricated rod.

"Ow, ow!" she cried out as her stomach cramped, the burning discomfort going deeper. It felt like he was shoving a brick up her backside, the stretch of her muscle was so painful it felt like any moment it might tear... but instead it just strained and burned as her body adjusted. The way her leg muscles might burn as she pushed for a last sprint in a long distance race or her lungs might burn if she was running out of air. Except that it was in a far more intimate space and she'd never felt anything like it in that area before. "Mark please, it hurts!"

"Shhh, princess, you'll get used to it... I promise... fuck you feel good..."

Emmie moaned, realizing that Mark was going to take her virgin hole no matter how much begging and pleading she did. And wasn't it only right? After all, he was leaving her hymen intact, she was still going to be a real virgin... so she'd thought she could get away with a blowjob and hadn't realized that something like this might even occur to a man, that didn't mean she got to choose how he took his pleasure.

As he pushed deeper, the feeling of fullness amplified along with the uncomfortable burning sensation, making her insides tingle and spark with sensation.

"OW!"

"Fuck that's good..." Mark groaned as he bottomed out.

The tears on Emmie's face, the way she was biting her lip, her pleas... and especially the submissiveness of her body despite her pleas, was absolutely fucking perfect. He could see every emotion in her open expression, watch every flutter of her eyelashes, and enjoy every little jiggle of her tits as he rocked deeper inside of her. Her asshole was so tight, so hot, he knew he wasn't going to be able to hold out much longer.

"Oh yeah..." He pulled halfway out, just enough to check and make sure he hadn't torn anything during his defloration of the tiny hole, and then shoved back in, hard enough to make her squeal and clench around him. "Fuck Emmie... your asshole is so hot..."

The squeals and tears continued as he pulled back out and then slid back in, making every thrust long and hard. Emmie writhed at the strange sensations; it felt almost stranger as he withdrew than when he filled her. Not like a bowel movement, because it was too fast, too uncontrolled. It made her feel like the pit of her stomach was dropping out of her, as if her body was actually being pulled away from her. Every thrust made the tight ring of muscle at the entrance to her body burn even more, the slick glide of his cock still creating friction despite the lubrication because she was so tight.

Gasping, she dealt with the discomfort as best she could, surprisingly aroused by Mark's groans and the way his muscular body heaved over hers. As her body adjusted, his thrusts came harder and faster, and the burn was slowly morphing into something else... something more pleasurable.

She surprised herself with a moan as his hand slipped down from her hip to press his thumb against her clitoris. The little nubbin ached as he touched it, toyed with it, and her tunnel clenched around him, feeding more sensation into both of them.

The fact that Emmie was clearly starting to enjoy herself, whether or not she realized it, that she was lifting her hips and squeezing his cock for all she was worth, over and over again, had Mark's knees feeling weak. She was so fucking hot. So fucking perfect. He held back his own orgasm, rubbing her little clit while she grinded back down on him and gasped.

"FUCK!" Her asshole squeezed hard and Mark's willpower broke.

Shoving into her, deep and hard, he groaned as his cock jerked inside of her, thickening and lengthening as his balls tightened and his cum began to spurt. Something about it must have set her off, because Emmie screamed out his name, her body writhing as her ass began to spasm around him, like it was sucking on his cock and trying to draw out his cum. Mark groaned as his knees actually buckled and he slumped over her body, his hips moving, rocking slightly as he pumped streams of cum into her deflowered ass.

Emmie's soft body was practically folded in half beneath him, but she didn't protest as she moaned and shuddered with the last remnants of her own orgasm. He could feel the wetness of her pussy pressed against his groin and he grinned. Still a virgin pussy. Hot damn.

"Hey Emmie?"

"Mmmm?" She moved slightly against him, making his soft cock fall from its warm haven and he groaned a little in disappointment.

"How would you like to be my personal sorority girl this year? I can promise I won't take your virginity," his hands drifted down to cup her ass cheeks, "but I'm going to fuck this ass as often as I can."

It didn't take more than a second for her arms to come up and wrap around his neck. "That sounds nice, Mark."