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Introduction:

A girl gives his boyfriend the best birthday present there is.

*Warning: May contain kissing*

Cindy sighs. She’d been waiting for the inevitable, and her new boyfriend didn’t disappoint. Being a girl of short stature with relatively modest breasts, there is one particular feature of hers that tends to attract men more than any other. And much to her dismay, it isn’t her love of the arts and sciences, or her glasses that announce such things to the world. It is that which her mother gave her. Which, itself, does not refer to her penchant for emotional honesty, her taste for fantasy fiction or her appreciation of the scientific method, but instead to an anatomical property that is pleasing to the eye. Which, again, does not refer to her red hair or her green eyes, typical familial traits that are inherited in simple genetic patterns that can be mapped out by Punnett squares, but instead to a property that is only indirectly inherited through a complex interaction of genetics, lifestyle and…

It’s her ass. She’s got a big, round ass. You could call it a big, fat, round ass, if she wasn’t in earshot.

She doesn’t mind particularly that the men who chat her up with sex or even a relationship in mind probably sneaked a peak at her from behind (though the cat calls and the weird, random sexual solicitations she could do without), but she never made the connection between admiring her rear end and wanting to put it in her butt. Unquestionably, that was the elephant in the room, whenever she asked a boyfriend if there was anything they wanted to try. She couldn’t quite understand the logical leap from like a big, round rump to wanting access to option number two. Still, Cindy was willing to try anything once. Or a few times. With each boyfriend.

Well, while she’d led her current boyfriend to believe that she’d never done such a thing before, this wasn’t entirely the truth. Or, anything like the truth. The reason for the deception was two-fold: first, because she didn’t want her relatively vast experience with the practice to mislead someone into thinking she was unbreakable, and second, because she didn’t want to cultivate a reputation as the type of girl that takes it up the bum. It was inevitable that she be asked, after all, and she didn’t think it was very fair to say no, arbitrarily, as she was perfectly capable of doing it. Still, she never wanted to hear that one of her guy-friends saw “Cindy is an anal queen” on a bathroom wall and would she very much mind confirming or denying that she “took it in the arse?” So she didn’t exactly want to admit to just anyone that she’d actually done it more times than anyone could reasonably keep count.

And, yet again, her boyfriend of several months, who’d so far been the nicest and most patient man she’d ever been with, had brought up the issue in the roundabout fashion that men seem to mistake for subtlety.

“Isn’t it weird that anal sex is, you know, a thing?” he had said, one lazy early-summer evening, while the fan in the room hummed and she lay silently in his lap, browsing through e-books on her laptop. It was probably the most abrupt way anyone had ever brought up buttsex to her, and she had to hold back laughter when she finally put together what he’d said. He was idly stroking her hair at the time, and when she looked up at him, he was staring off into the upper corner of the room, a blush evident.

“Uhm… in what way?”

“Well.” he said, getting back on script, as if she’d just responded “who’s there” to “knock-knock.” “It’s just that, it’s totally doable, you know? And there’s no real evolutionary purpose for it, right?”

“It might be for male bonding,” she had said, trying to hide how amusing she found it to derail his tortured interest probe, “since pygmy chimpanzees do it for that and a bunch of other reasons, and historically, that’s how humans have used it, too. Bit of a chicken or egg, though, since the properties that make anal sex possible are basically just the properties of a functioning rectum.”

He had nodded, utterly defeated, and had gone back to stroking her hair without saying anything. Taking pity on him, she’d given him an opportunity to follow up.

“Why have you been thinking about it?”

“Oh! It’s just, you know how it is. Brain misfires… just random stuff. I’ve just been thinking about it for a while. Trying to model… human behavior and, uh, sexuality. In my head.”

“How’s that working out for you?” she had said, stroking his chin with her fingers.

“Could be better,” he’d said, deflating. “So… you don’t think that men and women should, uh, do it?”

“Anal? I mean, I don’t think what ‘nature intended’ should really factor into it.”
“Oh,” he had said, a bit relieved, “so, would you do it?” He didn’t get around to saying the “with me” part, probably because he wanted a generic theoretical answer, first.

“Me? I… haven’t thought about it, much.”

“Oh.”

And that had been the end of it. Cindy now knew that her boyfriend wanted to fuck her butt, and had desperately wanted to ask her about it. Looking back on it, she sighs again. What else can she do?

They’d gotten to the “spare key” stage pretty early, so she was waiting in his place for him to get home. She had spent the day eating the food in his fridge and hiding from the midsummer heat, because she didn’t handle heat very well, her body not being designed for shedding it. That was the principle: tall and skinny, sheds heat well, short and plump, you come from the subarctic.

Still, though, she’s willing to make a sacrifice for him. She’s wearing her most formal jeans-and-tshirt combo, and a pair of heels that she’s certain she could last maybe three, four hours in. When she hears his key in the door,she positions herself in front of it, so that when he opens it, she hugs him around the neck and plants a kiss on his lips.

“Happy Birthday,” she says, while his eyes adjust to the darkness of the cave that she’s created for herself. He reaches over to the light-switch to turn it on.

“Hey, Cindy, I’ve been calling you all day. Is your cellphone dead again?”

“Uh… maybe.”

He sighs. “So, you want to go out tonight? It is my birthday,” he says, exaggerating it. He had told her previously that he didn’t particularly care about his birthday, and didn’t really expect to receive gifts from people.

“We could go out…” she says, still hugging close to him, her breath on his neck, “if you want to. I’ve got a restaurant picked out… your favorite… my treat. And after, we could go see that new Ricci brothers movie you’ve been so excited about. And then we could buy a loaf of bread, and sit by the bay feeding the ducks until the sun sets…”

Slightly distracted by her seductive demeanor, he doesn’t respond at first, but after a moment, he seems to agree.

“…or… we could stay inside, and you could fuck my ass.”

He freezes. He tries to read her expression for any sign of a “got ya!” but all he can notice is a faint, haughty smirk and a hint of anticipation. She suggested a romantic night out on the town, and he certainly wouldn’t mind going to his favorite restaurant, seeing the movie he’s been waiting to see for months, and then relaxing by the seaside… but… but… butt…

She doesn’t say anything to ease the tension. She watches his mind jumping through hoops. Watching him turn himself inside out was probably worth it. Had he heard her wrong? He suddenly becomes very aware of her weight sitting in his lap. His hands are on her back, but he could answer her without saying anything… but what made her change her mind? Had she changed her mind? Is it a trap?

“We could… we could go to the movies…” he says, half-committed to his decision.

“We could… but don’t you want to stick it in my pooper?” she says, and he whimpers. “ I know you’ve been wanting to for… well, since you first told me, but I’m sure it’s been at least a little longer than that.”

He remains silent. Again, she watches the wheels turning. Just as he’s about to speak, she slips off of his lap and turns away towards the door. “Alright, movie it is,” she says, walking deliberately away from him. Before she has a chance to turn and see his reaction, his arms are around her, and he pulls her towards him with so much force that she’s nearly lifted off her feet.

“H-hey!” she admonishes, not wanting to lose control of the situation. He lessens his grip, somewhat, and starts to kiss at her neck, apparently under the impression that he should be doing his best to romance her. She appreciates the effort.

She bends over to touch her toes and is nearly knocked to the floor in thanks, as he nearly barrels her over in his excitement. “Let’s… ungh… go over to the bed,” she stammers out while he humps her from behind. He releases his hold on her, and blinks half-mindedly, as if recovering from a daze.

“Is this for real?” he says, though out of genuine incredulity or boyish glee she isn’t sure.

“No promises,” she says, draping her arms around his neck again, leaning up to kiss him, “but if you play your cards right,” she continues, turning around with her arms still embracing him.
“What do I have to do?” he says, and the way he says it makes her consider giving him a list of her enemies. She walks over to his bedroom door, and leans against the frame.

“Kiss me,” she says, with a bit more hesitance than she thought she would.

She expects him to bound over to her in a single step and smash his lips into hers, but he calmly, if deliberately, walks over to where she is, leans low and kisses her softly. She closes her eyes, and puts her hand on his chest.

“Not there,” she says, though with less of an edge than she thought she would, when they part. She’s not sure if it’s because he’s trying to “play his cards right,” as she’d suggested, but the way he’s acting is making it difficult for her to keep the breaks on.

Which is to his advantage, as the very next thing she knows, she’s face-up on the bed, and her shirt is off. So is his. She’s halfway between the headboard and the foot of the bed, and he is before her, pulling her legs up. She motions to unfasten her pants, but he’s already done it, and is now pulling at her pant legs, taking off her underwear simultaneously. He doesn’t even bother to remove her socks before she feels his breath on her sensitive parts. She absentmindedly places her hand on his head, urging him forward, and when his tongue makes first contact she grips at the sheets, having already worked herself up more than intended. Her heart is racing and her lips are trembling. She squeezes him with her thighs while he licks her up and down, soft and teasing at first, and then growing more and more insistent, pausing occasionally to try and thrust the tip up inside of her vagina. To his credit, he manages to keep his focus there, showing a greater level of self-restraint than she currently is, thrashing her petite upper body in ecstasy while her lower half keeps him pinned in place, her wet warmth robbing him of breath, while he ignores any and all discomfort in favor of continuing his pace, which stays steadily even as she grows more and more tense, ever more and more soaking. If he needs to come up for air, her thighs are ensuring that he can if and when she gets what she wants. And she does, as her body goes completely tense, and he feels her legs constrict around him once, twice, thrice, and she buries her face in a pillow and moans heavily, her first orgasm of the night a short, intense one.

Her eyes still adjusting to the post-orgasm world, she looks down at him between her legs, and remembers what it is she agreed to. Were it not his birthday, she would have little hesitation asking for another go, but instead, she rolls over onto her belly, and fishes through his nightstand for the tube of lube that she’d hidden there previously. If he notices this forethought, he doesn’t mention it, and instead rubs his face ungracefully against her backside, taking special care to kiss her beauty mark, which he’d already confessed was his favorite spot of hers. Having a conspicuous spot on the part of her that men were already particularly focused on made her self-conscious, as knowing she had a mark there was an embarrassing tidbit that always seemed to make its way through the grapevine, like it was the only important thing to talk about. Pushing that thought aside, she comes upon the lube, and hands it off back to him, and he accepts it.

A squirting noise, and then in short order, his hands are working between her cheeks, making her backside as sticky and lubricated as the front.

“Easy now,” she says, having regained her composure, and having previously learned the danger letting a lover get too excited prior to the actual buttsex.

She doesn’t feel him for a second, and turns to see what he’s doing. He’s hesitating.

“Do you… want to be on top? It might be easier, you know, if you can control it…”

“What? Oh… sure,” she says, flipping over, trying not to get lube on the sheets. He leans back, and she crawls over to him. He watches her hips sway side to side as she crawls, and she climbs on top of him, and sits on the base of his cock. Her cheeks are sticky, and she can feel him erect against her tailbone, but he hasn’t lubed himself yet.

“You need to lube yourself up, too,” she says, taking the bottle from him. She squeezes out a handful, reaches behind her, and grabs hold of his shaft, running her hand up and down it. He moans at the touch, and she notices that he’s harder than he’s ever been. She also makes a note that, despite her history, this will be the biggest one she’s done anal with. Most girls wouldn’t let him NEAR them with that thing if that was his intention, but here she is lubing up the full length of it. She hopes that he appreciates the effort, as well.

“Now, no sudden thrusting, okay?” she says, and waits for him to nod. Instead, he gets a funny look on his face.

“Have you… done this before?”

The question catches her off-guard, and she just sits in stunned silence for a second. He chuckles to himself, which breaks the tension, but her cheeks redden. He looks her up and down, as if deliberately “resizing” her, and so to steal back the reins, she pushes him over, and sits up, holding his cock underneath her.

“Here,” she says, emphasizing “here” by putting him up to her puckered anus, “I’ll show you how it’s done.” With that, she starts to lower her weight onto it, but the head is too large for immediate entry. She watches him watch her with intense interest, as she pushes the tip of his cock up against the entrance to paradise. He grabs hold of her waist, and for a brief, terrible instant she thinks he’s going to pull her down onto it, but instead, he seems to be making it easier for her to hold up her own weight. She smiles a clumsy smile of gratitude and keeps trying to get the tip in, relaxing her body and pushing out, but his big, stubborn dick refuses to go. In frustration, she presses harder than she knows she should, and she yelps with success as it pops into place, her anal sphincter simultaneously held open by and clasping onto his upper shaft. Her breath becomes erratic and she grunts a bit in discomfort as she gets used to the challenge of it, but he doesn’t take much notice in his reverie. She takes her hand off of it – her sphincter is doing a fine job holding it in place, and puts her hands on his chest, steadying herself at that height above him. She breathes in through her teeth, as does he, but for different reasons. When she finally does start to move, only a tiny bit, he lets out a loud moan of appreciation, and she smiles in spite of it.

She gradually uses the movement to open her up, so she can lower herself onto it. Because he’s holding her up partly, she’s having an easier time of the cowgirl position than she had in the past, since having to hold herself up and relax her muscles at the same time was nearly impossible. Still, his size is an obstacle, and she’s glad that he’s smart enough not to make fun of the face that she’s making while trying to get used to the overly-stuffed sensation of his oversized member. Still, she doesn’t like the way he seems to enjoy seeing her sweat and grit her way through it. He does find it a little funny, and a little cute, but he keeps that to himself. Instead, when she’s about halfway down, he whispers “I love you,” and she slaps him hard on the chest. He flinches, and in playful retaliation, he sits up, places a hand in the small of her back, and then slaps at her big, fat cheek with the other. She yips, more out of surprise than anything, because he didn’t really put any force behind it, but as revenge she bites gently into his shoulder. This proves to be a miscalculation, as the ante-raising doesn’t end there, and he slaps her again, more of a true spank now, and then again. She bites him less playfully, but doesn’t actually tell him to stop, and so he holds his hand a long way off to the side, and she watches as it disappears behind her, and feels the burning sting of it before she hears the thunderclap, and the jolt in her loins as she comes to discover something new about herself. She leaves teethmarks in his shoulder, more out of reflex than spite, and then releases him. He rubs at the bitemark, and sees that she her eyes are tearing up.

“Are you alright?” he says, concerned, not realizing that a combination of a shock, pain and little bit of cumming caused the tears, and not sadness or betrayal. Partly because she doesn’t want to have him feel bad about it, and partly because she’s a little drunk on lust, she responds in a wordless way that raises the stakes tremendously, as she puts her hands on her own cheeks (feeling the warmth on the left one), and starts to sink down on him. She looks at him between matted bangs, biting her lip and maintaining eye contact while she slides down over him, or while she takes him inside, depending on the perspective. She nearly takes the whole thing from half of it, and she knew it would be uncomfortable, as she grits her teeth and sucks in air and her rectum protests, but the pain is surprisingly invigorating, and the look on his face would be impossible otherwise. Her insides are churning, telling her to expel the intruder, who has much too much girth for a petite girl like her, and far too long for just about anyone, but what did her insides ever do for her, anyway? She looks down at him, breathing heavily, shaking a bit.

“Say it again,” she says, sweetly.

“I love you,” he says, straining a bit from the sensation, but still as sweetly as he can in kind.

“You mean that?” she says, starting to move, slightly, again, placing her hands on his chest again.

Without warning, he pulls her up by the hips, and they separate, him popping free of her ass with a comical finger-in-mouth noise, which embarrasses her a bit. The sudden exit makes her rings spasm, and she’s about to chastise him until she sees that his face is composed and certain.

“I love you,” he says, again, and pulls her onto his chest, holding her head against it.

“I love you too,” she says, and is about to fall deep into the moment until she remembers what they were doing. She pushes herself up, again, into her sitting position, and then lines his cock up with her entrance again. “Now, you don’t belong there,” she says, pushing his head back inside, and then rearing up. “You belong in here.”

She starts to ride up and down, longer strides now than she had before, and he grabs onto her waist again, but this time he takes a more active role. She knows that if they do this often enough, she’ll be able to fit snugly around him with only minor discomfort, and then they can really go wild, but for now, she’s still keeping him to an even, half-shaft pace. Still, he presses up against her walls with a force, as she’s too tight to accommodate how thick he is. Another girl might consider them mismatched lovers, what with his fat cock and her necessarily petite, taut options, but Cindy isn’t a quitter.

She wonders why she keeps acquiescing to these requests, aside from just her good nature and her desire to keep her partners satisfied in all the ways she can. Here she is, bouncing up and down on another stiff cock in her ass, when she could have just stuck to her guns and ignored it. Of course, while she doesn’t like to admit it, she knows the real reason why. She knows her body’s best feature, and she knows that she likes it when a guy goes crazy for it. Most of all, though, she knows that she likes the feeling of it disappearing up her chute, over and over again, or she wouldn’t be able to stand how big this one was. Or sit on it, for that matter.

He has her stop for a second, which leaves them in the awkward position of having him inside of her ass while she sits on him, still, while he fumbles around on the floor for something, which amuses her. He comes back up with a remote in hand, and uses it to turn on the stereo. He clicks it a few more times, and starts playing one of her favorite songs. Without saying another word, they resume their pace.

She thinks that it’s a sweet, romantic gesture… until she notices what he’s using the bass beat for… and then she has to admit that it’s kind of hot. She also likes the position, as from a doggy style position (which is what guys usually request), she has to stimulate herself, and from any reverse position, she can’t watch her boyfriend’s face while she’s coaxing it out of him. She also likes that he’s helping her do the work, which all in all, means that she’s enjoying it quite a bit. She can’t have the full sheet-ripping orgasms from before, but she feels herself building to something all the same.

Without thinking, she coos “right there…” to him a few times, and he responds by putting his hand underneath where she’s rubbing against him. Him touching her clit sets her off, and she sighs through a small, satisfying one, constricting around him involuntarily in the middle of it.

He’s smugger than before. “You like it in your ass, don’t you?” he says, reaching up to her face, and slipping a finger into her mouth. If it wasn’t his birthday, she’d give him a piece of her mind, but instead, she just smiles coyly. She doesn’t want him getting too full of himself, but a little riding high was good for anybody. In the past, a few guys had played up the “you’re a little whore” angle too strongly, and she’d left them high and dry. Right now, though, she didn’t want to have a prideful temper tantrum, along the lines of standing up just as he’s about to finish, as if to say “I’m taking my butt and going home.”

Instead, seeing that he’s quickly approaching his limit, and is trying to stammer out that he’s about to fire off like a geyser, she has a different ending in mind. He dutifully gave hers, without hesitation or complaint, and so she’s more than willing to return the favor, a final birthday gift that he won’t soon forget. At the height of his stroke, nearly slipping free, she sits down, or perhaps more accurately slides down, burying him in all the way, nearly sitting on his sack while he’s suddenly now pushing open twelve inches of her protesting rectum that are definitely going to feel it in the morning. Her soft weight is resting down on him, and while normally she’d be a bit self-conscious about it, in that state, with him lodged in her most vulnerable place, she looks down on his face, covered in sweat and contorted in ecstasy, and has a quiet moment of triumph all to herself. She squeezes her sphincter around his base, and his eyes nearly roll up into his head. She enjoys knowing that with just a quick few squeezes, she could squeeze it out of him like toothpaste. Or lube. She considers saying “yes, I like it in my ass. Don’t you?” but decides to save that for another time. Instead, she rears up, all of her weight supported on her big round tush, pressing it down on his pole, and feigns concern. “What’s the matter?” she says, shaking her hips and butt a bit, knowing that he’s in absolutely no position to answer. She stretches and turns to look back at where he’s penetrating her, and she can see that his cock is pulsing at the base. A twin pair of devil and angel appear on her bare shoulders and tell her both to stand immediately and to sit still for a belly-filling moment longer, and she’s not even sure which is which. It’s quickly a moot point, however, as though the pair of figures remain nearly perfectly still, he groans, and she can see it on his face a second before she can actually feel him erupt in her ass, a sudden impact, and then building pressure, as he fills her now-sticky bowels with a desperate deluge of thick, teased-out sludge. She suddenly finds it difficult to breath, and she realizes that in his excitement, he’s squeezing her waist so tightly that she’s locked in place. She feels a little twinge of embarrassment at his eagerness, and a little bit of pride, and more than a little bit of excitement, herself, knowing that she’d have no choice in the matter if she had decided differently. Then again, she’d already made her choice, and once it was made, he didn’t have a chance to pick out an alternate ending. She thinks to warn him that he’s hurting her, but he relents before she does, and pulls her down from her position on high, bringing her face close to his.

She pulls her face away from him, and he kisses her neck in unconscious desire. “You want to kiss my face while you’re shooting in my ass?” He grabs her by the nape of the neck and pulls her into a kiss that she barely fights before returning it in earnest, knowing full-well the sorts of names he’s picking out for her in his head as he frenches her while nutting in her butt. Still, his kiss is affectionate, and she can’t fault a boy for wanting to think of her in that way while literally further in her than a thermometer. She wouldn’t let him see her blush, though.

When the twitching stops, and he’s filled her up as much as she can, to the point where she can feel it sloshing around, she kisses him again. “Did you like it?” she says, knowing that anyone would have a hard time giving him a better experience with anal.

“When can we do it again?” he says, eyes lightning up, and she grabs his chin and shakes his head.

“Now you’ll have something to look forward to your next birthday for,” she says, eyes narrowing, and she can see his terror. “Maybe Christmas, if you’re good.”

“But… I thought… did you not like it?”

She sighs. “I’m kidding. Yeah, I liked it… just don’t get any ideas. I only let gentleman fuck my ass.”

He smiles. “My lady, you will find that I am of the highest order of gentleman,” he says, and then reaches behind her to slap her ass again. “Sometimes.”

“That’s fine,” she says, running her finger along his chest until it touches his hand, “you’ll find that I am of the highest order of lady,” she says, taking his finger into her mouth, and sucking the tip, “sometimes.”

“I… yeah,” he says, still shellshocked.

She looks behind her again, and then back at him. “You ready to come out?”

“Yep.”

She leans forward, and pulls him out slowly. The head pops free like a champagne cork, and she resists the urge to let his copious gift follow. It will take her a bit to get back to a less open state, and as it is, she’s glad she didn’t have a big lunch. Like clockwork, and just like all the others, he eagerly requests to see his handiwork. She pushes aside the thought that he resembles a fresh-faced young boy who had a new toy to play with, noting that she’d probably have to admonish him after all was said and done that her puckered anus is, in fact, not a toy. A bit indignant, as is her usual demeanor directly before, during and after a rump-roast, she spins around on him, reversing the position, which she liked to think of as “slutty cowgirl.” She sat on his abdomen, which was hard, with her backside, which was soft, and she had to admit that the odd skin-on-skin contact was pleasant. She knew he was running his eyes up and down her body, or at least, up to the small of her back. Looking over her shoulder, she confirms her suspicion, as he makes no attempt to look up at her face. She rubs her bottom on him, and he finally meets her eyes.

“This is what you want to see, right?” she says, rolling her eyes, before leaning forward, grabbing onto his ankles, hiking her rear-end up in the process. She shakes it in his face, and swears she can feel him release more cum onto her stomach as a result. He gets an eyeful of the full, naked moon that he’d been denied viewing while they were actually going at it, as well as a proper view of the place where he’d left behind a few billion sperm. Her anus gapes slightly, looking every bit as indignant as its owner, and for a brief flash imitates the amount it was forced open when he was inside of it. Having satisfied his request, Cindy dismounts abruptly, before he has a chance to stick his finger inside. She thinks that his tool can’t be much smaller than a fist, but she’d rather not bet her ass on it. When she starts to walk over toward the bathroom, he lunges after her, hugging his face to her rear. Before he has a chance to motorboat it, like some kind of moron, she spins to face him, and instead he grabs around hips (his hands, of course, finding their way to her cheeks) and holds onto her. She pats his head, half-affectionately, half-impatiently, and he eventually relinquishes his bear-hug. Her legs wobbly, her knees slightly knocked, she marches ungracefully to the bathroom, closing the door behind her. She could hear him half-heartedly complaining that she wasn’t being very romantic, and she muttered to herself that if he put it in her front, their lovemaking wouldn’t conclude with a passionate trip to sit on the toilet and drop his load a second time. She feels his sperm swimming around in her belly, getting anxious, so she takes a seat, and waits for his birthday present to finish its journey.

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