This is my first Glee fic, it's a fill to a prompt on the glee kink meme. I can't link to it here obviously but this was the prompt:
Santana is getting herself off when she suddenly remembers something Brittany said about anal sex. She then decides to try it, since she's alone and pretty curious. She teases her ass while fingering herself before actually fingering her ass.
She's never had anal before so please have her building up to it and feeling kinda nervous about it maybe? But she really enjoys it.
Bonus: Same again but with more fingers/toys.
Note that I don't know much about anal but I'm guessing she would need some kind of lube and wouldn't just push right in, please be realistic, plus the buildup is the best part ;)
I could possibly be pursuaded into doing a sequel, or maybe even turning this into a series if there's enough interest. Let me know :) I would love to get some feedback!
Anything He Can Do, I Can Do Better
Santana grunted in frustration as the ache in her wrist began to overpower the ache between her thighs. She'd been going at it for almost a half hour now and every time she felt near to climax her thoughts would shift from the blondes on her laptop to the blonde she wished were in bed with her, and the pleasure would instantly turn tail and head the other way. Honestly, at this point she wanted her orgasm simply because she couldn't seem to reach one, and not because it felt even remotely enjoyable anymore.
At this very moment, while she was laying naked on her bed with her hand between her thighs and her laptop propped on some pillows next to her, Brittany was on a date with Artie. It was her fault too, for refusing to sing a stupid duet with her, and now the girl she was madly in love with and had been since kindergarten was boning someone else.
Actually, she was still boning her too, but it felt different, like Brittany wasn't as into it because technically what they were doing was cheating. Not that that had ever mattered in the past, to either of them, but then she supposed she had never actually felt threatened by any of Brittany's so called "boyfriends" before. Not that she was threatened by Artie! No, she was threatened by what it was that the boy was capable of giving her. Things like feelings and eye contact and the like.
There were other things too, the non sexual type, like public displays of affection and biological children, but at the moment all Santana could focus on was what the blonde had told her earlier that day while they were fooling around in the janitor's closet after lunch. She had mentioned how during her last "sleepover" with Artie, he had tried something that no one had ever done to her before.
Apparently Professor X had an anal fixation, and had managed to convince the girl to let him finger her back there while she rode him reverse cowgirl style. But what was worse than the resulting horrifying mental images she still couldn't erase from her mind, was the fact that Brittany had liked it. Or, as the girl had put it, "It felt so fucking good San! I don't think I've come so hard in my life!"
The memories of that conversation were what was keeping Santana now from being able to finish her own self off. Every time she tried to concentrate on either the building pleasure in her groin, or the two hot blondes on her computer screen, her mind would suddenly flash to an image of Brittany taking a finger in her ass. At least she had managed to erase Artie from the picture, and so that finger was more often than not her own tanned digit.
She had never really thought about anal before and so the fact that it was all she was capable of thinking about now really wigged her out. If Brittany were with her right now, would she try it with her? Could she actually do it? Would it feel weird? Or dirty? Would she hurt the girl? Would Brittany want to do it to her?
Wait, what? Santana stilled her hand completely, leaving her three fingers still wedged inside of her mainly dry opening as she processed the thought. Would she let Brittany finger her? In the ass? "Fuck..." She whimpered as she realized that the answer to that, while not a resounding "yes", also wasn't a definitive "hell to the no".
Would she like anal? She had thought that she was an "exit only" type of girl, but then the topic of that type of sex play had only ever come up when she was with a guy, and the last thing she wanted was for a dude to stick his schlong into her ass. She could barely stand to have that thing inside her vag. But Brittany wouldn't be using a hunk of meat as thick around as her wrist, she'd be using her finger. Her teeny, tiny, slim, ickle little finger. She could totally handle a finger up there, right?
As if the adware on her computer could read her thoughts, a banner for a site dedicated to lesbians and anal sex appeared at the top of her web browser. Did she dare, though? What if she clicked on it and her screen was flooded with images of gaping assholes and things being put into them? She didn't want to be scarred for life by the fetishes of some people, but she also knew that the site she was on wouldn't have anything even remotely close to what she was now envisioning.
Rolling onto her side, she wiped her hand on her bed spread and moved her laptop's pointer so that it was hovering over the banner. She was home alone so she didn't have to worry about the volume, and it was her own personal computer that no one but herself and Brittany knew how to unlock, so there was no risk of anyone ever stumbling upon her browser history. Biting her lip she hesitated for a second and then tapped her trackpad.
Luckily what came up wasn't what she had been afraid of. There were no guys, or their dicks, no close ups of vegetables being shoved into someones behind, the usual things she tried ever so much to avoid. There were just images and video previews of a bunch of really hot girls, most of them blonde, and she was definitely okay with this. In fact, she quickly bookmarked the site into her secret "lolcat folder" before finding a video link that sounded promising and clicking on it.
Five minutes later and she was tearing up her closet looking for that bottle of lube she'd stashed away in there for reasons she must have had at the time. Far be it from her to admit that she was desperate, but there was no way she was trying what she'd seen in that video without the stuff, and there was no way she wasn't not trying it. She hadn't felt this turned on since discovering her pulsating shower head had three settings.
Finally though she found the tiny black plastic bag she had stashed the bottle in and quickly made her way back to her bed, belly flopping onto her mattress. Scooting her way back towards her laptop she tore off the cap on the tube and squirted a generous amount of the cold, slippery liquid onto her left hand. Pressing play with her other hand she settled back into her pillows and watched the girls on the screen show her exactly what to do.
Thankfully being on the Cheerios meant her diet was pretty restricted and so the chances of there being anything "back there" that she didn't want to encounter were pretty slim. But just to be sure, she inserted two fingers of her non lubed hand into her vag and felt around for any telltale signs. Satisfied that she was, indeed, empty, she focused now on the sensation of her slippery pointer finger circling around the ridged flesh of her back opening.
Having no idea the type of resistance to expect she pushed a little harder than what ended up being necessary and her finger was immediately swallowed up to the second knuckle. "Ohhhhh fuuuuck!" She hissed, bucking her hips wildly at the myriad of feelings, both painful and pleasurable. Pulling her finger out she let her head roll back on the pillow as she realized how hard she was breathing. How could this possible be turning her on so much? Maybe the girls in the video weren't exaggerating their vocalizations? Maybe Brittany was right about having never come so hard?
Fast forwarding the video to a different scene, Santana let herself calm down a little as she watched one blonde slowly tease the other with the way she only inserted her finger for a brief second before pulling out. She wasn't even going in that deep and the girl on the receiving end was practically convulsing. Okay so maybe they were exaggerating a little.
She needed to think differently about this though, because in the end this wasn't about finding new ways to enjoy her forever aloneness. No, this was about being able to top, or at least match Artie in what he was capable of giving Brittany. Yes, she wanted her orgasm, but she also needed to learn something from this. She didn't want to approach Brittany with the idea next time the girl was alone with her, only to look like she had no clue what she was doing. Fingering herself was easy since she could feel what she was doing, fingering someone else was going to be the tricky part.
Then again, Brittany wasn't exactly the hardest girl to please. Pinch her nipples hard enough and she'd come from that alone. But to get her to come "the hardest she had ever come in her life" was the task she was taking on and the hell she was going to come in second to Stubbles McCripplepants.
Rewinding the video to a particularly vocal part, Santana began to mimic what she was seeing on the screen. Slowly she would insert the tip of her finger, hold it there for a second or two and then pull out before repeating the action again. As it would turn out, the act of repeatedly causing ones sphincter to clench and release was a huge fucking turn on for her, and she almost felt guilty for all the gay male sex bashing she had spewed out over the years. Apparently guys weren't lying when they said it felt good to be stretched in that way.
Not that she needed to be thinking about guys right then, not while she was knuckle deep inside her own ass once more. "Nnnnngghnnn..." She found herself moaning along with the girl in the video as she experimented with curling the tip of her finger inside of herself. It was definitely no where near as stretchy as her usual hole, but she was starting to think that she could actually possibly even get a second finger into her and like it.
Not wanting to ruin the entire experience by hurting herself she took the bottle of lube and squirted even more onto her fingers as well as some over her back opening itself. Not even paying attention to the video now, Santana tentatively pressed the tips of her first two fingers against her hole and began to push. It was definitely not as easy going as one finger had been and she almost stopped multiple times when the sharp, stinging pain that occasionally shot through her caught her off guard.
Once she was in past her ring of muscles, progress was a little faster, though she was still hesitant to simply thrust her fingers deeper like she had done when she was using only the one. It hurt the way her body was stretching around the intrusion, but it also felt good in a way she would have to come up with words for later when she wasn't so in the moment. Right now she needed to focus on the end result which she could already tell was shaping up to be a pretty fucking spectacular orgasm.
It was slow going but eventually she found she could pump her fingers in and out of her at a speed that matched the throbbing she felt elsewhere in her groin. Taking her other hand she began to rub at her clit, her hips rocketing her upwards at the suddenly desperately desired added stimulation. So maybe she couldn't come from anal alone but that's why god had given her two hands, right? Not to mention the box full of sex toys she had hidden also in her closet. She very much wanted to see Brittany riding her reverse cowgirl now.
She kept these newer, much more appealing thoughts in her head as she sped up both of her hands. She was breathing erratically now, her head thrashing back and forth on the pillow, her laptop completely forgotten about on the pillow next to her. She could feel it coming, the orgasm she had been chasing all afternoon, and as she had predicted, and hoped, it was going to be fucking magnificent.
With a few more thrusts and passes of her hand, she finally toppled, screaming out her ecstasy as she convulsed on the bed in much the same way the girl in the video earlier had been doing. Stilling her motions, she groaned into her shoulder as she felt her insides clenching around the two fingers she still had lodged in her ass. It wasn't the rhythmic pulsating she would have felt inside her pussy, but it was still hot as fuck and kept her from removing her hand until her body finally calmed down completely.
Once the waves of pleasure had passed and she had managed to regain control of her breathing, Santana slowly worked her fingers from her ass and let her legs collapse down to the mattress as her body essentially went limp. She was exhausted but in that "just fucked into oblivion" type way and she was considering simply falling asleep like that, naked and everything on top of her blankets. Her parent's knew better than to enter without knocking.
Or so she thought. Freezing up like a statue, the girl's eyes travelled to her bedroom door which was now being pushed horrifyingly wide open. Only where she had expected to see one of her parents shocked and mortified faces, she saw Brittany's devilishly grinning one. "That was hot, San." The blonde told her as she entered her best friends bedroom, turning to shut and lock the door. "But you know what would be even hotter?"
Santana wasn't sure she was breathing as she shook her head to the girl's question. This wasn't necessarily a bad thing. It was certainly better than having to explain to her parents what she had been doing, if such an explanation was even necessary. Her parent's weren't prudes, they must know what teenagers did while they were naked and alone in their beds in what they thought was an empty house. Failing that, the very obvious "porn sounds" coming from her computer would have clued them in.
Brittany had been watching her best friend through the crack in her door for the better part of ten minutes and was now practically gushing between her own thighs. Her date with Artie had ended early since he had gotten an offer to play Call of Duty with his guy friends and had told her that he wasn't feeling well enough to go to Breadstix with her as planned. He didn't think she knew the truth but she did since Puck had sent her the txt invitation as well. Not that she'd really minded anyway. She'd have much preferred spending the evening with Santana.
Which was why she had been standing outside the girl's bedroom door watching her frantically fuck herself in the ass. Which was also why she was now climbing up onto the still stunned silent girls bed, begging her to "do that again", only this time to her. It didn't take much more convincing than that to get the latina to nod and before Brittany could even blink she was being flipped over onto her back as a pair of hands began to tear eagerly at her jeans.