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Emmie Does Anal

Category: Anal Sex
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Emmie paced around the small room rather fretfully, wondering what on earth she was going to do. She desperately wanted into the sorority that she’d applied to, even though she’d known from the getgo that it required its freshmen members to sexually satisfy the frat brothers of a neighboring house. That fact was the worst kept secret on campus. But every girl wanted into the sorority; it took good care of its sisterhood, other than the sex stuff. And Emmie needed someone to help take care of her.

If she got into the sorority then she would have a place to live, food to eat, and help with her studies. As a scholarship student who’d been forced to take out several loans, that was a big deal. Emmie was well aware that a lot of money flowed into the sorority from the fraternity next door, although of course it was never said that sex was part of that, everyone knew that it was. She supposed that might make her a bit of a whore, but as long as she got through her education without being completely buried by loans, then did it really matter?

That was what she’d told herself, the justification that she’d come up with, although secretly there was another truth, another reason that she’d chosen this particular sorority, even if she couldn’t admit it to herself. Yes, it was the one that would provide the most benefits for her, yes it was the one that would happily take care of her basic needs for all four years, yes all of her worries would cease once she became a sister…

But even more so, Emmie was turned on by the idea of being forced into a kind of sexual servitude.

Although the eighteen year old was beautiful and had gotten plenty of attention from guys all her life, she’d always been too shy to do anything about it. Her senior year, her prom date had kissed her and she’d run. Literally run. Ended up catching a ride home with one of her friends. Daughter of a single mother who never dated and who had been overprotective of Emmie her entire life, she had no idea how to talk to or relate to guys. Not really. And her mother had always harped on how Emmie needed to make sure never to let a guy take advantage of her, unless she wanted to end up alone and pregnant like her mother had.

Since Emmie had graduated high school, her mother had left her on her own, saying that she was going to find a new place to live and Emmie was now an adult and had to care for herself. Emmie had stayed on friends’ couches until school started. It was pure luck that she’d won a scholarship for the first semester of school that covered almost everything, but the loans would kill her in the long run. Helping her get the loan had been the last thing that Emmie’s mother had done for her, but it was in Emmie’s name. She absolutely did not want to end up like her mother, which was why she needed this sorority. But she was scared of actually having sex, because what if she ended up pregnant? Then she’d not only be like her mother, but all of her dreams would go up in smoke.

So she was really hoping that the guy she’d ended up with would be happy with just blow jobs… not that she’d ever given one of those, but she could learn. It would still be better than finally giving up her virginity and risking pregnancy. But she was also hoping that the frat brother she was expected to umm…. service would be understanding of her lack of experience and be willing to lead her through the steps.

In the back of her mind, Emmie had always fantasized about being forced to do sexual things… heck, it was probably the only way she’d ever be able to do them at all. Going along willingly made her feel like a bad girl, thanks to her mother’s upbringing, and her sexual fantasies had always involved being held down. When she’d gotten a little older and had listened to her friends and explored on the internet some more, they’d become more involved and elaborate, involving rope or blackmail… although she ignored this when she joined the sorority, pretending that it wasn’t why she’d chosen this particular sorority.

Dana, the sorority sister in charge, had listened to Emmie’s concerns and had assured her that she had the perfect guy for Emmie. Which is how Emmie had ended up in Mark’s room, the VP of the frat, pacing back and forth as she waited for him. She was dressed up the way Dana had chosen to dress her, in a virginal white silk nightgown that had scratchy lace over her nipples, keeping the little nubbins hard, and was barely long enough to cover her bottom. Emmie wasn’t entirely sure that it was covering her bottom, in fact, it felt as though her cheeks might be peeking out from the hem… but at least she couldn’t see it.

And a guy would probably think it was sexy, wouldn’t he?

Biting her lip, Emmie studied the pictures that were up on a bulletin board in the room. Mark was a definite hottie… tall, blonde hair, green eyes… he looked like a teenage heartthrob actually. She knew that he was a Junior and that he played lacrosse for the college, going by the books on his shelf she guessed that he was probably majoring in business. Unfortunately none of that told her what to expect when it came to what he might want in bed. Dana had seemed sure that Mark would have no problem with Emmie’s desire to remain a virgin though… maybe he was gay and she would just be a beard?

She didn’t know whether she would feel relieved or disappointed about that. Probably both, but, she admitted to herself, probably more disappointed than anything. Emmie desperately wanted to know more about relations between a man and a woman even if she didn’t want to lose her virginity. She’d be willing to try other things though.

When the door finally opened, she spun around, a bit wild-eyed, to see the man himself walking into the room. While she’d seen him around before, she hadn’t actually been this close to him and she hadn’t realized exactly how tall he was. Or maybe it was just because he was fully dressed and she was wearing nothing but a nearly transparent tiny slip of fabric that made her feel so vulnerable.

He was between her and the door and there was no escape… her nipples had been hard before, now they were fully engorged and slightly aching as a strange throbbing began between her legs. Emmie had never felt anything quite like it. Of course, she’d never been in a situation quite like this either.

Staring up at him, she realized that she was definitely attracted to him. That was a plus.

“Hi-i-i,” she stuttered, and then fell silent not knowing what else to say.

Mark grinned. The cute little brunette in front of him didn’t seem to know whether she wanted to be terrified or turned on. Not entirely surprising. This wasn’t his first time doing the exchange with the sorority and most of the girls were nervous their first night. And this one had more right to be nervous than any others, considering that she was a virgin and didn’t want to lose that status.

She definitely looked the part, in that white slip, even with how see-through and short it was. The hard little buds of her nipples were completely visible through the lace over them and Mark felt his cock hardening. Knowing that she wanted to keep her cherry had only made him more excited while he’d been on his way to meet her; seeing her was even better than he’d imagined.

Very cute and curvy, adorably nervous, and willing to do anything to keep herself virginal. Yeah… he liked that.

“Hello Emmie, it’s so very nice to meet you,” he said, shutting the door behind him and striding forward. She backed up automatically, her head tilting back as her dark brown eyes widened. The fear and anticipation on her face made his cock rock hard. “I hear you’re a virgin and that you’d like to stay that way.”

Although Mark’s blunt talk made her blush, Emmie was grateful that he brought up the issue that concerned her the most immediately.

“Yes,” she said, her blush deepening. Although when she did lose her virginity, she hoped it was to a guy as hot as Mark. But she didn’t know him and that so wasn’t going to happen. No matter how hot a guy was, she was going to stick to her convictions. “Um… Dana said that you would have an alternative.”

She said it almost like a question, the hopefulness in her voice was obvious even to her. Would he be insulted? To her relief, Mark just chuckled. As he brought his hand up to cup her cheek, his knuckles grazed over her nipple and she gasped at the electric sensation.

“I do indeed have an alternative,” Mark said. Dana knew all about his preferences, although he doubted he’d be the only guy in the frat to use that alternative enthusiastically. “No worries, sweetheart, we’re going to have fun this year.”

Before she could ask any other questions, his hand was sliding around to the back of her neck and he was lowering his mouth to hers. Emmie gasped in shock – she’d known what tonight was about but she’d honestly thought there’d be more preliminaries. Using her gasp, Mark slid his tongue into her mouth, kissing her deeply and overwhelming her senses. From the way her hands fluttered against his chest, he knew that she didn’t have a lot of experience, and he relished subjugating her mouth to his.

Emmie moaned as his other hand reached around her body, gripping her bottom in hard fingers and pulling her forward so that she was flush against his body. He was incredibly muscled, his chest hard underneath her fingertips, and what was digging into her stomach was even harder. Yeah… so not gay. The realization that this incredibly hot man wanted her made her go all fluttery and warm inside, while his kiss made her tingle all the way down to the tips of her toes.

It wasn’t that she’d never been kissed before, but she’d never been kissed quite like this – with the expectation that it was definitely going to go somewhere. Mark wasn’t hesitant, he didn’t ask permission, he didn’t take his time and make sure she was okay with each step… he just took. And she gave, her nipples aching as her pussy became slick and swollen between her legs. Moaning, Emmie gave herself over the kiss.

Slowly backing her against the bed, Mark could feel the petite freshman relaxing against his body and he inwardly crowed. Not just a virgin, but obviously attracted to him and willing to follow his lead. This wasn’t just going to be satisfying, it was going to be easy as long as he didn’t give her time to think. Emmie was a fruit that was more than ripe to be plucked. Hell, if he wanted to, he could probably pop her cherry tonight – he had no doubt she’d go along with it. Her body was moving against his almost uncontrollably, trying to rub against him in the way a woman did when she was hot and unbearably horny, unable to think because she was too swamped by sensation. Innocents were the easiest.

Fortunately for her and morning-after-regrets, he was after a different cherry altogether.

When her legs hit the bed, Emmie found herself falling back, gasping for air. Her lips felt almost bruised from Mark’s kiss, her pussy was so wet that the tops of her thighs felt wet as well, and she was shocked by how aroused she’d become. Never in her life had she been so turned on before. Was it just Mark? Or was it the way he was behaving? She had to admit, she’d always had a secret passion for romances with hot alpha males who took what they wanted. So was it the situation or was it just him?

“Ooooohhh…” she moaned as he yanked at the top of her slip. The flimsy straps dug into her shoulders and then they tore, allowing him to pull down the silky material. The lace scraped over her swollen nipples until they were bared to his gaze. Immediately, Mark leaned over her, taking one of the pink buds into his mouth as his other hand latched onto the opposite breast, squeezing the soft mound of flesh.

Emmie grabbed hold of his head, holding him tightly against her breast as his tongue lashed the tiny bud that he held between his teeth. The sharp bite only seemed to enhance the pleasure, a shock of electricity going straight to her core. Moaning, she moved her hips up and down, and she felt her swollen netherlips scrap against the rough material of his jeans.

The position had him between her legs, his thighs pressed up against the edge of the bed so that she couldn’t close hers, and the slip had ridden up to her hips. Writhing beneath him as he suckled at her breast, Emmie realized she was getting more of an education than she’d bargained for – she really hadn’t known what to expect, but it certainly wasn’t this wild, chaotic, uncontrollable passion that was roaring through her veins right now. This was better than any of her fantasies, although the situation was very close to ones that she’d had a million times before.

“Such sweet titties,” Mark murmured, switching nipples in his mouth. Emmie’s skin was so soft, her breasts so heavy and full in his hand. He loved the way she writhed beneath him, how her fingers dug into his scalp as he sucked hard on her nipple. The smell of her musk was already filling the room and he didn’t doubt that she was getting pussy juice on the front of his jeans. It just turned him on more. His cock was achingly hard and he desperately wanted to free himself and just ram into her. But that wasn’t the way to start off this year – and as he was determined to keep Emmie to himself, he preferred that she come and offer her body to him willingly on a regular basis.

At least she definitely like a little pain with her pleasure, that would help her. As he bit and sucked hard on her nipples, she mewled and clutched at him, moaning more like a porn star than a virgin. He didn’t doubt that his roughness was hurting her, just a little bit, but she seemed to like it – Emmie didn’t seem the type to fake reactions like this.

Deciding that he wanted to leave the torn slip on her – it add just that little bit of extra debauchery to the situation – he reluctantly left her breasts and crouched down between her legs. Not surprisingly, Emmie’s face turned beet red and she tried to bring her thighs together, but he kept a palm on the inside of each one to keep them well apart.

“Don’t worry, Emmie, I just want to taste this virgin pussy,” he said, grinning at the idea. Keeping his elbow on her thigh to ensure her legs would remain spread, he used two of his fingers to spread her pussy lips as she moaned with embarrassment… but now that he’d reassured her, she didn’t try to close her legs again. “Has anyone ever eaten you out before?”

Too embarrassed to actually speak, Emmie shook her head. She was looking down the length of her body to where Mark was staring intently at her splayed privates. Just looking at herself made her feel slightly ashamed; her breasts were covered in red and pink marks from his fingers, her nipples were incredibly swollen and a much darker pink than usual, and she could see the slight sheen of wetness on her inner thighs from how turned on she was. The look on Mark’s face made her feel slightly better though, he looked like a man enthralled.

Something stroked along her inner lips and she gasped and moaned, her entire body tingled in response.

“And definitely a virgin. You are amazing Emmie.”

This time she flushed with pleasure, relieved by the sincere admiration in his voice. After all, she was within his hands. If he wanted to take her virginity forcibly, she knew he could. He wouldn’t even need a lot of force, she was so aroused. But if he admired her for being determined to remain a virgin, then he wouldn’t take it, right?

So what did he want?

Just as the question went through her mind, Mark lowered his mouth to her and she shrieked as his tongue swept up the center of her nether lips, slipping around her clitoris with a flourish. It was the most incredible thing she’d ever felt and all of her thoughts immediately went flying from her head as her hands gripped the sheets on his bed. Then his mouth began licking and nibbling all over her tender flesh and she thought she might actually pass out from the pleasure.

“Mmmm, so sweet,” Mark said as he lapped at her cream. Emmie tasted like woman and peaches, tart and sweet on his tongue. He’d been rather fascinated to see her hymen, just like in pictures on the internet. So she had never had anything inside of her, not even a toy… and never had a man’s mouth on her either.

Yet she was his, all his, to play with and debauch – to a certain extent. Mark groaned as he sucked more of her pussy into his mouth, nibbling on the delicate folds as Emmie gasped and writhed. Draping her legs over his shoulders, he continued his oral assault as he reached out with his left hand, opening the drawer of the end table next to his bed, his hand unerringly finding the tube of lube that he kept there.

Emmie was so responsive, so wet, that it was no hardship to unbutton his shirt with one hand, then unbutton his pants and free his cock while still licking at her pussy and making her moan for him. He probably could have done just about anything to her swollen pussy and she would writhe for him, she didn’t need a focused assault and so he was free to ready himself.

Coating some lube on his finger, he pressed the tip against the tiny rosebud of her virgin anus and made little circles. Immediately Emmie’s hips lifted as the strange sensations richoted through her.

“Mark! What-?” She groaned as the tip of his finger slipped into her body.

“Don’t worry, Emmie, this will feel good,” he said, before his wicked mouth went right back to doing what it had been doing.

Releasing the sheets, she grabbed at his hair as the strange sensation of something actually entering her backdoor shivered through her. It didn’t hurt but… it felt so very strange. So wrong. So… so… good. She moaned against as his tongue flicked against her clit and the finger pressed a little deeper, working itself back and forth and igniting a whole new set of nerves that she hadn’t known existed. The stretch of her tight ring of muscle was the most uncomfortable part – other than mentally – but Mark was right. It did feel good too.

Especially as she relaxed and gave in to him, making it easier for his slick finger to glide back and forth in the tight space. His mouth moved up her body slightly, settling over her clitoris, and he sucked the swollen nub between his lips. Emmie thrashed on the bed, her insides spasming, clenching against his finger as the itching, burning need inside of her began to swell even larger.

Sensing the approach of Emmie’s orgasm, Mark pushed his finger back and forth, stretching out the tight virgin asshole. Pleasuring her helped, as did the fact that she’d relaxed. As he continued to flick her clit with his tongue, drawing little circled around the nubbin, he pulled his fingers out and began to press back in with two fingers.

“Oh Mark!” Emmie’s head thrashed back and forth, her hands in his hair tightening around his head. “I can’t… oh god… I’m so full!”

Not as full as you’re going to be, he thought wickedly. He sucked on her clit, steadily, over and over again, like a baby at its mother’s breast, and the steady rhythmic sucking made her scream. The walls of her rectum spasmed around his fingers, the same way her pussy was spasming around emptiness as she came. Mark sucked and flicked at her clit, listening to her cries of pleasure as his cock began seeping pre-cum in excitement.

The orgasm was tightening her sphincter, but as she began to come down from the incredible high of pleasure, it loosened around his fingers. She stroked his hair, sighing in feminine repletion. It was exactly the way he wanted her.

Using his left hand to coat just a bit of lube over the tip of his cock – he wouldn’t need much considering the amount of her juices that were spilling down her crack and the lube he’d already used on his fingers to loosen her up – Mark pulled his mouth away from her pussy and stood up. Emmie smiled up at him, a lazy smile of a satisfied female.

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.


“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.”

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