G!P Regina George x fem!reader
CW: butt plugs, brief mentions of masturbation, anal sex, reader is described as enjoying the pain, very vulgar language, dom!regina, mentions of a safe word but it isn’t used, clitoral stimulation, vaginal fingering, condom usage
A/N: okay so a while back i did a nsfw alphabet for regina and for one of the letters i said that her dirty secret was that she really wanted to try anal but was too embarrassed to bring it up and i had a couple people request that i write about that so here it is :)
It all started when Karen Smith, the well intentioned, but utterly naive girl that she is, gifted you a card game for your birthday, claiming that she’d found it online and that it was a super fancy Prussian version of Uno. You didn’t have the heart to ask her why the hell she would gift you the foreign version of a very popular card game that you already owned, or to inform her that the country of Prussia ceased to exist long before she was ever even born, so you just put on a smile and opened the present.
Much to your surprise, (and dismay) the card game Karen had bought for you wasn’t any version of Uno from any country, past or present. It was a card game for couples to spice up their sex lives.
You and Regina were mortified, and after Gretchen ushered Karen into another room to explain to her that she’d essentially just gifted you the equivalent of a sex toy that you’d just opened in front of all your friends, the blonde girl returned to apologize and sheepishly explained that she couldn’t return the game because her credit card had been put on hold again due to ‘suspicious spending.’
So the game sat in your closet for months after that, only serving the purpose of being something you laughed about now that the initial embarrassment had faded. You hadn’t opened it, and you never planned to. You figured that one day you’d sell it online for five bucks and get it off your hands and out of your closet.
But then on a rainy Friday night, which was typically date night for you and Regina, you invited her over to order in, bake brownies, and watch a couple of movies since the weather had spoiled your original plans (and because you knew she much preferred cozy nights in anyway, even if she’d never admit it.)
While the brownies were in the oven and you were halfway through a movie you’d already seen a thousand times, Regina grabbed the remote, turned down the volume, and turned to look at you with a playful smirk. “Remember that weird, horny card game Karen gifted you that she thought was Prussian Uno?” She asked.
You rolled your eyes. “Ugh, yes. How could I forget that? I love the girl, but that was so humiliating.” You shuddered slightly as the embarrassing memories came flooding back, that was something you’d replayed more times in your head than the movie on your TV screen.
“You still have it, right? You should go get it.”
Your head snapped towards her, your eyes narrowing in both annoyance and confusion. “What, do you think we need to spice up our sex life like some straight couple in their mid to late fifties? Why the hell should I go get it?”
Regina rolled her eyes and clicked her tongue. “Of course I don’t think we need to spice up our sex life. And please never compare me to a straight person ever again.” You couldn’t help but laugh at that, and while it made your girlfriend smile, it didn’t keep her from continuing to push this topic. “I just want to look at it, that’s all. I bet there’s some really funny shit in there.”
You pursed your lips together, considering her suggestion. While you’d avoided even opening the game because of how weird you found it, you couldn’t deny that you were curious as to what it entailed. And Regina was right – there probably was some really funny stuff in there…
“Fine,” you huffed after a minute, trying to pretend that you weren’t also excited to see the contents of this game. “I’ll go grab it. You stay here and keep an eye on the brownies.”
Regina smiled victoriously and nodded her head, mumbling her agreement as she watched you walk away.
Not even a minute later, you returned with the game in hand and sat across from Regina on the couch, quickly tearing the thin plastic sheet off the box and opening it to reveal countless white cards neatly stacked inside.
Regina frowned in confusion as she stared down at the stacks of cards. “Is that it?” She asked. “It’s just… cards?”
You rolled your eyes, although you weren’t actually annoyed, and said, “Yes, it’s just cards. It’s a card game, babe. What, did you want some fuzzy handcuffs included or something?” You teased.
“No, I don’t want any fuzzy handcuffs!” She denied immediately, a frustrated huff leaving her lips. She tried and failed not to turn beet red at your little joke. “I just figured there’d be more… substance, I guess.”
“Well, we haven’t even read the rules yet,” you pointed out, feeling weirdly defensive over your perverted card game. “Maybe there is more substance.”
Regina shot you a skeptical look and grabbed the small booklet from inside the box, flipping through it until she found the gameplay rules. She skimmed through it briefly, her perfectly plucked eyebrows furrowing in concentration, before she closed the booklet and tossed it onto the coffee table. She looked up at you and said, “It’s literally just would you rather.”
You were surprisingly disappointed to hear that. “What? How do you determine who wins?” You asked, leaning over to grab the rules off the coffee table. You turned to the very last page and scoffed at what you saw. “You’ve gotta be fucking kidding me. ‘At the end, the real winner is the couple who has a revitalized and passionate sex life?’ That’s such a cop out.”
Your girlfriend started laughing, both at how shitty the game was and how frustrated you seemed by it. She shook her head when you glared at her. “What? You can’t seriously have been expecting anything better. Who knows what kind of sketchy ass website Karen bought this from?”
“It’s not that I was expecting anything better,” you explained with a shake of your head as you crossed your arms over your chest. “It just pisses me off that there’s someone out there profiting off of such a shitty product. I mean, there are vulnerable people out there. Like Karen, for example. She doesn’t know how to tell if a website is legit or not, she didn’t know her own middle name until last year!”
Regina sighed softly and smiled at you, reaching out to pat your shoulder. “There’s a lot of injustice in the world, babe. But very little of it has the chance to be really funny. So come on, put down the pitchfork and laugh at these stupid cards with me, okay?” She offered, trying to gently get you to see that you were being a tad bit dramatic.
Luckily for her, she actually got through to you, and you just sighed and said, “Fine, fine, we can look at the stupid cards. But they better actually be funny…”
With that, you and Regina began to look through all of the cards, and even though you were both laughing and treating it as a joke, somewhere along the way you started to play somewhat seriously.
Most of the cards were pretty stupid and tame; stuff like ‘would you rather see me in lingerie or nothing at all?’ and ‘would you rather have sex in the shower or in the pool?’
But eventually, you pulled one that actually made you laugh out loud in surprise. Regina smiled and laughed softly herself. “What? What is it?” She questioned, reaching out for the card only for you to hold it against your chest.
“It’s just so intense,” you explained, still laughing softly. “I mean, this game has been pretty PG 13 so far, but this is straight up R rated.”
“Y/N, come on! What does it say?” Regina groaned, impatient as always.
“Okay, okay… it says,” you started, staring down at the card again while stifling laughter. “‘Would you rather have anal sex with me or watch me touch myself?’ Like, what kind of an escalation is that?”
Immediately upon hearing those words escape your lips, Regina’s face fell and her eyes widened. She could feel the growing heat of arousal stirring in her gut as her cock gave an interested twitch in her boxers. She swallowed dryly and looked up at you, her baby blue eyes darkening. “Anal?” She asked shallowly.
“Yeah, ‘would you rather have anal sex with me or watch me touch’ – wait a minute,” you interrupted yourself, a knowing smirk stretching across your lips. “Why did you have such a reaction to the mention of anal? Are you… are you into that?”
Regina looked at you like you had lost your mind, but her face was redder than you’d ever seen it. “What?! No! Of course I’m not into that, Y/N, oh my God! That’s… that’s so… perverted and gross.”
Maybe it was the fact that you knew her better than anyone, or the fact that she’d spent all four of her high school years turning her nose up at the theatre kids and all their school plays and as a result her acting skills were less than adequate. Whatever it was, you could tell that she was lying through her teeth.
“Oh my God,” you chuckled softly, covering your mouth with your hand like a middle schooler hearing an inappropriate joke. “You are into that!” You really weren’t trying to make fun of her or make her feel insecure about it, you just found it so surprising that you couldn’t help but laugh. You always thought Regina seemed like the type to think anal was gross.
“Babe, shut up,” the blonde whined in embarrassment, collapsing backward onto the couch and covering her tomato red face with her hands. “It’s not funny. It’s humiliating.”
You frowned, your heart sinking as a wave of guilt washed over you. Your first instinct was to reassure her, but you were briefly taken aback when you noticed the hard ridge of her cock straining against her sweatpants.
‘Damn,’ you thought to yourself. ‘She really is into this.’
Pushing aside the heat you could feel building in between your legs, you clicked your tongue and moved to straddle your girlfriend’s thighs, being extra careful that you didn’t touch her very obvious erection.
“Gina, babe, look at me,” you said, grabbing her hands and pulling them off of her face. “You don’t need to be embarrassed, okay? Plenty of people are into that, there’s nothing weird about it. I didn’t mean to humiliate you. I’m sorry for laughing.”
Regina’s demeanor softened a little, (except for that one thing, of course) and her shoulders seemed to relax as you assured her. Hesitantly, she reached out and placed her hands on your waist. “You don’t… find it gross or anything?” She asked in a whisper, making it obvious that she was still a little unsure about this.
“Of course I don’t find it gross. To be honest, I’ve never really even thought about it. But you’re obviously pretty into it, and… it does sound kind of hot. If you want to, I’d be willing to try it out…” you said, raking your nails gently up and down your girlfriend’s arms as she tried to keep her head from exploding.
All of a sudden, Regina’s mouth felt dry, and she nearly choked on air as she tried to swallow. “You… you’d let me fuck you in the…” she couldn’t even finish her sentence, her blue eyes trailing downward like she had some sort of X-ray vision and could see your ass through your front. Her hands trailed down slowly until she was groping your ass through your clothes.
You hummed in satisfaction, smirking at the way Regina was touching you. “Of course I would. I kind of like the thought of you filling me up from the back for a change,” you confessed, watching your girlfriend’s jaw drop as you shifted forward to settle your weight over the bulge in her sweats and leaned down to kiss her.
You stole all the air from her lungs as you pressed your lips to hers passionately, the way you always did when you were anticipating getting fucked. The feeling of your ass in her hands and the way you were grinding down just slightly against her straining cock made her head spin. She wanted nothing more than to give in – to flip you over on your hands and knees and fuck your ass like she’d been dreaming of. And now she had your permission.
But still, she knew this wasn’t the right way to do this.
So, with the hesitation of a woman denying herself a taste of heaven, Regina grabbed your shoulders and gently pushed you back. She swore at herself inside her own head as she saw the confused look on your face as you stared down at her, trying to catch your breath. “What is it? What’s wrong?” You asked.
Regina shook her head swiftly. “Nothing’s wrong, baby, it’s just…” she sighed defeatedly, her hands falling to your hips. “This isn’t something we can just… do, you know? If we did this tonight, you’d just be in a lot of pain, and I don’t want that. I want you to enjoy it, too. We’ll have to take a couple days to uh… stretch you out, I guess.”
Your eyes widened in surprise, and you could feel your face heat up with embarrassment that you hadn’t realized that. “Right, of course. We’ll just stretch me out.” The thought of that made your insides twist with arousal, and maybe a little bit of fear. “How exactly are we going to do that?”
Your girlfriend chuckled softly under her breath, finding your reaction cute. “We’ll look online. I’m sure there are tons of articles about how to prep for this. And of course, there’s always toys, lube, things like that. I’ll order some stuff.”
You nodded your head, feeling embarrassingly aroused at the concept of using toys to prepare for this. “Okay, sounds good…” you agreed before hesitantly adding, “As long as you promise I’ll have your dick in my ass by the end of the week.”
Regina groaned at the sound of that, her cock pulsing at the idea. She scrubbed her hands over her face. “You can’t just say things like that, baby. You’re gonna be the death of me…”
“Okay, okay, I promise. Of course I promise. God, I want this more than you do. I’ll fuck your ass by the end of the week, baby, I promise you that. Just need to get my girl nice and ready to take me…” she mumbled, reaching down to squeeze your ass once again. Then, like a complete cockblock, the oven started beeping, startling the both of you. “But for now, let’s get those brownies out of the oven before they burn.”
As soon as Regina left your place the following morning, (after fucking you all night long in the old fashioned way) she headed straight home and did some research about how to properly prepare you for anal. She knew that preparation was vital, as the last thing she wanted was to see you in pain because you just couldn’t handle her size. She needed a way to stretch you open… gradually, of course.
So she bought you a set of butt plugs that included five different sizes, ranging from small to fairly large. With that, she bought a bottle of anal lube, which was a lot thicker and more slippery than regular lube.
Unfortunately for Regina, you felt too shy to use them in front of her, but you promised that you’d wear one all day, every day, gradually sizing up until you were eventually wearing the largest one with the hopes of your girlfriend’s cock soon replacing it.
You were nervous the first day, but you still made good on your promise, coating the small toy in lube and carefully pushing it inside of you until it was all the way in. You were pleasantly surprised by the way it felt. It wasn’t big enough to hurt, but it was just big enough for you to feel the slightest stretch, which only reminded you of why you were wearing it in the first place and turned you on.
The second day provided only a slight size increase, but it was enough of a difference to make you feel rather scandalous. You went through your day with bright red cheeks and a suspicious nature about you. You couldn’t help but wonder if people, somehow, could tell what you were doing. Deep down, you knew that thinking was illogical, and that everybody was oblivious to the fact that you were literally wearing a buttplug in the office or in the grocery store, but the paranoia still loomed in the back of your mind. It was sort of like the worried feeling you always got when you were on your period and you just knew that everyone knew, (even though they never did) only kinky.
By the third day, the plug was a good bit bigger than the first, and you could really feel the stretch. It was painful when you first put it in, but once the stinging sensation subsided, you found that you actually really enjoyed the feeling. You felt completely perverted all day long at work, sitting at your desk and grinding back and forth slowly in your chair just to feel the plug pressing against the walls of your ass. The lube you’d used in combination with your own arousal had you soaking through your panties, and you considered taking your lunch break early, calling up Regina, and begging her to come fuck you already. But as the front of the box containing the little gift set your girlfriend had so lovingly (and perversely) given you said, patience is a virtue.
Day four was much the same as day three, only the size of the plug in your ass had increased yet again. It was big enough now that it made you painstakingly horny. All you wanted to do was fuck yourself with it, but it wasn’t long enough for you to actually accomplish that, it was only wide and round enough to stretch you out so you could be fucked later on. You barely got any work done that day, opting to take a fifteen minute break every hour to lock yourself in the bathroom and touch yourself. You’d slump against the wall, spread your legs, and use one hand to rub your throbbing clit over your panties while the other trailed down your backside to push the plug impossibly deeper. But no matter how many times you tried, you couldn’t manage to finish. So you decided to just go home early and take a cold shower instead.
Finally, after four days of torturing yourself, it was day five – the day Regina would finally come over and replace the inadequate plug in your ass with her more than adequate cock. You just had to get through one more day. But of course, as most things in life are, that was easier said than done. This plug was the biggest one in the entire boxset that your girlfriend had gifted you, and the difference even between this one and the last one was noticeable. You doused the thing in lube, spread your legs, took a deep breath, and slowly pushed the object inside yourself. A shaky gasp left your lips as you practically doubled over, grabbing onto your bathroom counter for dear life. The pain was immediate, but the four days of preparation you’d done beforehand dulled it enough that you could feel the pleasure too.
You tried your best to push through the sheer neediness you felt as your asshole clenched desperately around the plug, your hands trembling as you got ready for work. But when you saw your face in the mirror as you applied your makeup, cheeks flushed, eyebrows furrowed, and lips parted as little huffs of desperation escaped, that was the final straw.
You swore under your breath, grabbing a makeup wipe and clearing off the haphazardly applied concealer, (which was all you managed to do before giving up) and fishing your phone out of your pocket.
You called your boss first, briefly informing him that you wouldn’t be coming in today for ‘personal reasons’ before hanging up and calling your girlfriend instead.
It took her four rings to answer the phone, but as soon as she did, the grogginess in her voice made it obvious she’d been asleep. Of course she had, it was only 7 AM and she was unemployed, which was just one of the many perks she was enjoying throughout her college years as a courtesy of having rich parents.
“Regina,” you breathed out lowly, causing her to sit straight up in bed as she heard the seriousness in your tone of voice. Unsure what to say next, (you hadn’t exactly been planning this phone call, after all) you quietly admitted, “I called in to work today…”
“What? Why? Are you feeling okay?” Your girlfriend asked, showing off her caring side that only you got to see.
You were fed up with beating around the bush. You’d been stretching yourself out for her for almost an entire week. And this time, you weren’t gonna skirt around what you wanted.
“Because I want you to fuck me, Regina,” you stated simply, walking out of your bathroom and stripping out of your work clothes before climbing back in bed, your phone still pressed to your ear. “I’ve been shoving these stupid plugs in my ass all week, and I’m getting impatient. I want you to come over and prove to me this wasn’t all just a waste of time.”
You heard her breath hitch on the other end of the phone, and she swore silently under her breath as she hurried out of bed, her sheets crinkling audibly. “You want me to fuck you in the ass, baby?” She breathed out, arousal evident in her voice. “You’ve been enjoying the little gift I got you, hm?”
“If that’s what you call it…” you grumbled, squirming around in bed as the butt plug remained snug inside you. “I’ve been horny for fucking days, soaking through my panties at work… I had to come home early yesterday because I couldn’t keep my hands off of myself. So are you gonna come over and fuck me or what? That’s what the point of all this was, right?”
Regina’s cock hardened to its full length inside her silky boxer shorts, her balls pulsing with every beat of her heart as precum beaded at the tip already. Her eyes darted between her en-suite bathroom and her car keys on her dresser as she tried to decide between taking a quick shower and making you both wait or heading straight over and sliding into you from behind like she’d been dreaming of for far too long now. Needless to say, it didn’t take her long to make a decision…
“I’m on my way. I’ll be there in fifteen minutes.”
Regina managed to make her way to your apartment in a little over half that time, and gladly let herself in with the spare key you’d given her. Already knowing where you’d be, she made her way down the hall to your bedroom and walked in to see you lying in bed, just as she’d predicted.
“So,” she started, leaning against the doorframe with a smirk as she eyed your almost nude figure shamelessly. “Skipping out on work now, are we?”
Your head snapped toward her, and in an instant, you were out of bed and on your feet, walking over to her. Without giving her a verbal answer, you cupped the back of her neck and pulled her face down to yours before kissing her passionately.
Regina’s eyes widened a little, but she kissed you back nonetheless, her arms wrapping around you loosely enough to allow her hands enough leeway to trail down to your ass. She grabbed two handfuls and squeezed, tugging your body closer against hers.
You gasped at the feeling, pulling back before the kiss even managed to get heated. Before she could complain about you cutting your little makeout session short, you took a fistful of her shirt and yanked her towards you, not even trying to prevent her from falling when she stumbled. Once she steadied herself, you gritted out, “You think this is funny, don’t you? You make me keep a fucking plug up my ass for a week and then you come over and want to get handsy with me? I didn’t invite you here so you could kiss me and squeeze my butt, Regina. I want your dick up my ass. Is that clear enough for you?”
The blonde looked briefly taken aback, but your little display of dominance was no more intimidating to her than a tiny kitten hissing. Her perfectly plucked eyebrows rose then fell, the corner of her lips quirking up afterward. “Well, someone’s feeling feisty, aren’t they?” She teased, grabbing hold of your arms and keeping you in place before her just to prove that she could. “I’m gonna give you exactly what you want, baby. There’s no need to be a brat about it. But I’d like to have my fun with you first. I spent a lot of money on this little gift for you, you know?”
You frowned, your eyebrows furrowing frustratedly as you realized you’d been out dominated by your own girlfriend once again. You wanted to struggle out of her hold, you wanted to be a brat about this, but her hand trailed down to your backside so quickly that you didn’t get the chance.
Your eyes nearly bugged out of your skull when her fingertips found the base of your butt plug through your panties, and you yelped obscenely when she pushed it into your ass even deeper, letting you feel the toy pressing against the walls of your ass.
Regina chuckled smugly as you lurched forward and collapsed into her chest, your legs shaking as she gently manipulated the toy inside of you. “You are wearing it, aren’t you?” She asked rhetorically, pride riding the edges of her voice. “You’ve been stretching out this tight little hole for me just like I asked. I guess you can be a good girl when you feel like it. Or is it just when you’re getting something out of it, too?”
You glared at her, and she just laughed dismissively. “Bend over your bed,” she demanded, smacking your ass hard enough to make it jiggle when you turned around. “You’re getting fucked.”
You gasped at the sharp sting of her palm against your flesh. You practically threw yourself over your bed, gripping your sheets and pushing your ass out obscenely. You wiggled your hips a little, daring Regina to come and take it.
She slotted herself behind you with zero hesitation, grabbing your hips to still them before grinding against your backside. You sucked in a sharp breath when you felt her erection through the fabric of her sweatpants – a hard, rigid line that made it very obvious how much she wanted this.
She draped her body over yours just slightly, grabbing your jaw and tilting your head to be in just the right position as she leaned down and kissed you. You moaned into her mouth, the feeling of her tongue laving against yours making your head spin, especially with the way the incessant grinding of her hips was pushing the butt plug into your ass over and over.
You pulled back with a gasp, your lips swollen and your face flushed. “Oh my God, Regina,” you said breathlessly, your pussy dripping despite the fact that the focus wasn’t on it for once. “Just fuck me already. Please…”
All she gave you in response was a growl as she hurried to tear off your clothes. The little pointelle tank top went first, with Regina pulling it over your head so fast it nearly made you dizzy. Next were your slutty little pajama shorts, the ones you never wore around Regina unless you were planning on getting fucked. She tugged them over the curve of your ass and all the way down your legs swiftly, your panties going with them.
“Jesus Christ, baby…” the blonde groaned from behind you, her cock pulsing in her boxers at the sight of you before her, naked and bent over. She reached out and gave your ass another squeeze before carefully pulling the perfect globes of flesh apart to reveal exactly what she was after.
Nestled snugly inside of your puckered hole was the largest of all five butt plugs Regina had gifted you. It was so deep inside of you that all that was visible was the red heart shaped gem on the base of the toy, and the small trickle of lube dribbling down the side of it.
“That is so fucking hot,” Regina growled in a way that was almost feral, and you could hear the rustle of her clothes as she quickly tore them off. “Does it feel good, baby? Having something stuffed inside of your tight little ass?” She asked, more for herself than for you.
You whined desperately, grabbing fistfuls of your bedsheets in anticipation for what was to come. “It feels so good, Gina,” you whimpered, knowing that nickname drove her crazy every time you said it. “It makes me wonder what your dick would feel like inside of me instead.”
“Oh, yeah?” She grumbled, trembling with excitement as she reached over to your bedside table and pulled out a pack of condoms, a bottle of lube, and a hand towel. “Well, you’re about to find out, baby. Take a deep breath in for me. I’m gonna take this plug out.”
An intoxicating mixture of excitement and arousal sparked through you, and you nodded eagerly. Gripping the sheets tightly, you sucked in a deep, albeit shaky, breath in preparation.
Still, your body surged forward as Regina began to carefully pull the plug out of your ass, a guttural gasp falling from your lips as your slick hole clenched around nothing but air desperately.
“Fucking beautiful…” your girlfriend complimented under her breath, barely holding herself back as she came face to face with the thing she’d been wanting so badly for months. She chuckled in aroused amusement as she watched your asshole flutter, clearly in need of being filled once more. “Mind if I put a couple of fingers in?” Regina asked.
As soon as she had your permission, the blonde trailed two perfectly manicured fingers down your ass and pressed them against your needy hole. She made sure to coat them with the warm lube seeping out of you before carefully pushing them inside of you, savoring the sharp gasp you let out.
Her other hand came to rest on the curve of your lower back as she slowly filled you with her fingers. Once they were all the way in, she leaned down and pressed a kiss right between your shoulder blades. “Is that good?” She whispered huskily. “Not too much, right?”
“I-it’s good,” you sighed breathlessly, your eyes half lidded as you clenched around your girlfriend’s slender fingers. “Not too much at all. It feels… really good actually.”
Regina smirked softly at your answer, and began to carefully scissor her fingers inside of you, earning a sound from you that was somewhere between a moan and a gasp. “Good, baby. That’s exactly what I want to hear…” she praised you quietly.
Slowly, she started to pump her two fingers in and out of your hole, growing increasingly fascinated with how different, and yet in some ways similar, it was to your pussy.
Just when the novelty of having her fingers stuffed inside of you was wearing off and Regina began to grow overwhelmingly desperate to stuff her cock inside of you instead, you looked over your shoulder and pleaded, “Gina, please. I-I’m stretched out enough to take you now. Put your dick inside me, baby, please?”
Regina had never felt so in love as she did the moment you said those words, and it manifested in the way her cock was aching with the need to be buried inside your ass.
“Fuck, fuck, okay…” she whispered frantically, carefully pulling her two fingers out of your asshole and wiping the lube off on the hand towel she’d gotten before grabbing the string of condoms next. She tore one off and ripped open the packaging, sliding the latex ring down her rock hard member. Finally, she grabbed the bottle of lube and poured a generous amount over her shaft. She spread it around with a pump of her hand and poured even more directly onto your puckered hole.
“Alright, baby,” Regina said shakily, gripping her hard cock and pressing it against your asshole. “You ready for me, pretty girl?”
You whimpered in anticipation and nodded your head, your body shaking with both nerves and adrenaline. “Please, Regina,” you begged brokenly. “I’m ready for it. Please just give it to me…” you stuck your ass out a little more as if to prove your desperation, and it took everything in the blonde’s power not to shove herself inside of you right then and there.
“Okay. Just relax for me, baby,” your girlfriend instructed, although the tension in her own voice made it clear that you weren’t the only one who needed to relax. Regina’s entire body was tense, a taut wire ready to snap. But still, you happily obeyed her, taking in a deep breath and letting it out slowly as you willed your muscles to loosen up.
“Good girl,” Regina purred in your ear. She held one of your hips tightly, her other hand splayed across the curve of your lower back. Your body was intoxicating, and she felt utterly drunk off of you. Desperate for more, Regina gave one last command. “Deep breath in, my love…”
Again, you breathed in deeply, but this time all the air was stolen from your lungs when Regina slowly began to push her hips forward.
You gasped dramatically, your eyes practically bugging out of your skull as the blunt head of your girlfriend’s cock pushed past the tight ring of muscle. Tears pricked at the corners of your eyes, and you scrambled to grab fistfuls of the sheets just to have something to hold on to as you cried out in shock.
“Shh… that’s it, baby,” Regina grunted from behind you. Her hands were shaking violently as she held your hips. She’d managed to nestle just the tip of her cock inside of you, and the sensation had that familiar bliss gathering in her lower stomach already. “You’re being such a good girl for me. You’re taking it so well. I know it’s just so big, baby…”
You let out a guttural moan of both pain and pleasure, your cheeks turning red at her filthy praise. Your asshole clenched around her intruding member rapidly, almost as if it were trying to sus out whether or not the invasion should be allowed. But you’d already made up your mind. You wanted to feel your girlfriend rearrange your guts, and your body would just have to get used to that idea.
“M-more,” you choked out, surprising both Regina and yourself. The stretch and the sting of just the first few inches of her cock hadn’t yet subsided, and yet here you were pleading for the rest of it…
Regina let out a breathy laugh. She felt as if she must’ve died and gone to heaven. “More?” She repeated in disbelief. “Fuck, baby, are you sure you can take it? I don’t want to hurt you…”
“Regina, I’m sure!” You whined pathetically, your cunt clenching around nothing as your ass had its turn at being filled for once. “I can take it, okay? This is what I’ve been working for all week. Just give me your dick, baby…”
With a shaky hand, you reached behind yourself to grab Regina’s hip in a desperate attempt to get her to go deeper.
Luckily for you, your girlfriend was more than eager to give you every single inch you could take…
She swore under her breath and grabbed your hips in a vice grip, angling them upward just slightly before delving in further, giving you both exactly what you wanted.
“Ohhh, Jesus Christ,” Regina moaned as she stuffed the first half of her cock inside of you, the tight rings of muscle nearly giving her a heart attack. “God, you’re doing so well, baby. Taking this dick like you were made for it…”
You moaned pathetically at her words, your heart hammering in your chest as you stretched to accommodate your girlfriend’s thick length. The pain was intense and searing, but it was worthwhile. Still though, you weren’t satisfied…
“A-all of it, Regina…” you demanded through gritted teeth. “G-give me all of it.”
She nearly blew her load right then and there. “All of it? God, baby, you are fucking insatiable,” she teased, knowing she loved every second of it. “But no, sweetheart. Not right now. I think I’d split you right in half if I gave you all of it right now.”
Your head whipped back to glare at her over your shoulder, and she couldn’t help but notice the way your eyes were almost completely glazed over with lust. “I didn’t spend an entire week shoving stupid plugs up my ass just for you to act like I can’t handle your dick,” you snapped, your tone as bratty as you could manage. “I’m a big girl, okay? I can handle it. So just fucking give it to me, Regina!”
“Fucking brat,” the blonde spat out, yanking your hips back and burying herself all the way inside, savoring the pained yelp you let out when she did so. “There you go… you like that? Big fucking dick in your ass? You can handle it, huh? Why don’t you show me how fucking well?”
Your entire upper body collapsed forward, your cheek resting on your mattress as drool slipped down from the corner of your mouth. It was like Regina was fucking the brain right out of your head. “Nnghh…” you moaned incoherently, nodding your head stupidly. “Yes! Yes, give it to me!”
Regina chuckled darkly. “What’s your safe word?” She asked, splaying her hand over your lower back.
God, she was obsessed with this view of your body…
She smirked in satisfaction, a deep purr sounding from her chest. “Good girl…” she praised, grabbing your hips to ground herself. “Now, show me how well you can take this dick, baby.”
Regina didn’t make you beg this time, whether it was because she wanted to show you mercy or she was too worked up to hold herself back, you’ll never know. Regardless, the way she pulled halfway out before shoving back into you relatively roughly had your brain melting from the pleasure.
“Oh, G-God!” You cried out, your heart slamming against your ribcage as your chest pressed flat against the mattress, your tits spilling out to the side from the pressure.
The feeling of your girlfriend fucking in and out of your virgin asshole was intoxicating. Each thrust stole the breath from your lungs, and the way she filled you to the absolute brim hurt in the best way possible. The stinging stretch was painful and intense, and it was enough to bring tears to your eyes, but somehow it only served to complement the white hot pleasure you felt from being fuller than you ever thought possible.
Regina growled, goosebumps breaking out over her suntanned skin from just how good it felt to be buried inside of you. “Do you like that, baby?” She asked in a sultry tone. “Do you like me fucking your ass? Huh?” She punctuated her question with a smack to your ass, which earned a help from you that made her dick twitch with excitement.
“Fuck, yes!” You cried out, your voice breaking. You could feel her cock deep in your gut, and for a second you wondered if she wasn’t literally rearranging your organs. But whatever. It felt way too good for you to worry about that. “I-I like it, Regina, I fucking love it!”
Regina couldn’t help but moan at your answer, her pleasure only intensifying when you confirmed what she already knew – you were enjoying this almost as much as she was. “Good girl…” she praised, thrusting into you a little harder. “I love it too, baby. You’re so tight for me. You’ve never let anyone fuck this ass before, have you?” She already knew the answer, but God, she just wanted to hear you say it.
Luckily, you were perfectly keen to give her just what she wanted. “Never! You’re the only one who’s e-ever done this!” You assured, stroking her ego in a way she definitely didn’t need.
A mixture of pride and pleasure surged through Regina’s chest at your confirmation, and she could feel her orgasm beginning to bubble up in her lower belly. She really hadn’t been fucking you for that long, but she just couldn’t help herself. Your pussy was divine, of course, and she’d be perfectly happy if that was the only hole in your body that you let her fuck for the rest of your lives, but your ass was a completely different experience. It was tight in a way she’d never thought humanly possible, and it lacked the natural stretch of your pussy, so it squeezed her shaft deliciously. Your cunt was designed to make room for her, to allow her inside, but your asshole wasn’t like that; she had to force it to accommodate her cock, and she was incredibly grateful that you seemed to get off on the pain that inevitably accompanied that.
“Mmm… That’s so sweet, baby,” your girlfriend cooed, her thumbs tracing soft circles in the skin of your hips as she held them tight. “Letting me be the one to fuck this perfect ass for the first time… you really love me, don’t you?”
You let out a vulgar, broken moan. Your face and chest were completely flushed pink, and your head was spinning from the feeling of having your ass drilled. But the response you had when Regina asked if you loved her was always the same. “I do! I-I really, really love you, Regina!”
If it weren’t for the state of absolute bliss she was in physically, your sweet profession of love would’ve made Regina’s heart melt. But right now, she was too busy trying to empty her balls to focus on any of the sappy feelings. Still though, she’d always say it back to you. “I love you too, sweetheart. I love you so much. God, you’re incredible,” she cut her sentence off with a moan as your ass clenched around her tightly. “Letting me f-fuck you in the ass like this… fuck, I love you.”
She could feel her orgasm building rapidly as she slammed in and out of your tightness, her heart pounding in her ears as the pleasure threatened to overtake her. Your ass was so hot, in terms of both temperature and sex appeal, and Regina knew she wouldn’t be able to hold back for long, especially with the noises you were making and the obscene clapping of the fronts of her thighs hitting the backs of yours. “You’re about to make me cum, baby,” she panted out a warning, her balls drawing up impossibly close to her body. “Fuck, Y/N, you’re gonna make me cum…”
You moaned at Regina’s admission, feeling sparks shoot through your tummy as your own orgasm began to build. “Fuck, yes!” You cried out, shoving your hand between your thighs to rub your needy clit. Your hips jerked at the feeling. “C-cum for me, Regina! Cum in my ass!”
Your girlfriend groaned and almost allowed herself to tumble over the edge before slowing down just enough to temporarily stave off her orgasm. “No,” she growled, her cock twitching wildly inside of you as if to protest her slower pace. “I want you to cum first. I need to see you cum from having my dick in your ass. Think you can do that for me, princess? Think you can cum with my cock shoved all the way up your ass?”
“Yes! Yes, I-I can cum from this,” you rambled brokenly, rubbing your clit in quick circles as it pulsed against your fingertips. With Regina’s thick length fucking into you so deep, and the stimulation of your fingers on your clit, your orgasm was so close you could taste it. All you needed was a little more, a little push over the edge…
Almost instinctively, you pleaded with your girlfriend for help. “Regina,” you whined, tears pricking at the corners of your eyes in desperation. “I-I need something else. I’m so close, I just… I don’t know!”
The blonde shushed you soothingly, her hips picking up the pace. “I’ve got you, sweetheart,” she panted, close to cumming herself. “Let me take care of you.”
You nodded desperately and Regina took one hand off your hip and brought it down between your legs before shoving three fingers into you without warning. You were so wet from both the lube dribbling down from your ass and your own arousal that her fingers slipped in with zero resistance, giving you nothing but sheer pleasure. And when she pushed her fingers knuckle deep and curled them against your g-spot, you were sent headfirst into the most intense orgasm you’d ever had.
“Regina!” You screamed brokenly, mind warping waves of ecstasy crashing over you with the force of a tsunami. You tried to tell her you were cumming, but when you opened your mouth all that came out was a guttural, animalistic moan. But it didn’t really matter; Regina could tell you were cumming anyway.
“That’s it, baby,” she praised breathlessly, watching with pride as your arms gave out and your upper body slumped against the mattress. “Good girl… cum for me.”
You couldn’t have stopped even if you wanted to. Your eyes rolled back in your head, your jaw dropping open and your tongue lolling out of your mouth like a fucking hentai character. You’d had plenty of orgasms before, most of them at the hand (or cock) of Regina, but you’d never had an anal orgasm before, and it was a completely different experience. It was bigger, deeper, and it felt so much more rewarding because of the pain you first endured to get here.
Just as the last waves of your orgasm were lapping over you, Regina’s hips began to stutter, her thrusts turning desperate and sloppy as she let out quiet swears and moans. Her cock began to twitch inside of you like it had a mind of its own, and you realized what was happening before the words even fell from her lips.
“Fuck! Fuck, I’m cumming, baby!” Your girlfriend moaned, her voice cracking pathetically. Her grip on your hips grew impossibly tighter as she buried herself all the way inside your ass and let go. “Ohhh!” She moaned in relief as she slumped over your body, her hips giving tiny little thrusts to thoroughly milk her cock as she spilled inside the condom.
You let out a pleased hum as Regina’s orgasm slowly tapered away, her hips rolling shallowly as her cock began to soften. She breathed out a contented sigh in your ear and collapsed on top of you, pinning your body underneath hers on the mattress.
She was the first to speak after a few minutes of radiant silence, letting out a simple, “Holy fuck,” that earned a laugh from you. “I’ve never cum that hard before in my life. That was… Jesus, baby…”
You giggled tiredly, tapping her hip to signal for her to get off of you. “That good, huh?” You asked, shuddering softly when she pulled out of your ass.
“That good,” she nodded in confirmation. She pulled you into her arms and you lay against her chest, listening to the rapid beat of her heart. “What did you think? Was it worth the week of butt plugs?”
You chuckled softly and leaned up to press a soft kiss to her lips. “Without a doubt.”
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