This is another one that was published elsewhere anonymously (I think I had a different title for it there, though). This one was an attempt at a fill for the GKM, since it should be clear now I have a certain fondness for filling prompts and I was looking for a fun challenge, and at the time this was the one that caught my attention just to see if I could do it. It was written basically in one sitting.

By way of warning of the content, this was the original prompt:

"Brittany really wants to try anal sex for the first time ever, but is afraid Santana won't agree to do it. She ends up asking Santana but puts her idea down in the process. She doesn't even wait for Santana to answer, but instead tells her that it's a stupid idea anyway and that Santana shouldn't listen to her.

First Santana is a little perplexed by what is going on, but then she realizes that Brittany is embarrassed and scared and insecure. Santana interrupts Brittany's rant and tells her she would love to try something new.

In the end, Santana rims Brittany and takes her anal virginity with a strap-on.

Bonus:
- sweet!sex
- understanding/whipped Santana wanting to please her girlfriend"

So, if doesn't sound like your thing, I completely understand. If it is, I hope you like it.

Santana can tell by the way she fidgets that there is something on her mind. She does her best to convince herself not to worry. The landscape of Brittany's mind can produce anything from the inspiration to cure cancer with fairy dust to an almost eerily accurate prediction of the new fall trends in footwear. Even though she can't help but still be just a little bit nervous, waiting for the moment when Brittany's attention might wander to someone else, she tries her best not to dwell on it.

She has, for the moment anyway, the person she's always dreamed about, the relationship she always wanted, even before she would have admitted it to herself. And whatever is on Brittany's mind will spill out eventually, she just has to be patient and wait for it.

As it happens, her patience is rewarded much sooner than she would have imagined. They are in the bleachers, watching the rest of the Cheerios running endless circles around the gym. It's good to be the Captain. Or the Captain's girlfriend. So long as they are in top form during competition, Sue allows it. Santana thinks she might still feel a little guilty for her part in getting them outed, but she's not going to complain. Wind sprints suck.

They are fun to watch, though, which she does dutifully so she can say she fulfilled her leadership role. She gets a few dirty looks and wonders with a smirk if they really think the glare of a sophomore with cottage cheese thighs is supposed to bother her.

Brittany feels no particular need to watch the torment. She's laying on her back, ankles crossed with her head pillowed comfortably in Santana's lap while her mind wanders off to whatever mysterious places it is drawn to.

"Hey, Santana?" She begins quietly, taking one of Santana's hands in hers and playing idly with her fingers.

"Hmmm?" Santana's reply might seem distracted, but in reality she has an almost laser like focus on her girlfriend.

"Do you ever want to try things?"

"What kinds of things?"

"I dunno. Just, you know, things."

She frowns now, because something that vague can lead to all kinds of dangerous territory where Brittany is concerned.

"I need a clue here, Britt." She says carefully, now ignoring the panting cheerleaders and giving all her attention to the girl in her lap.

"Like, sex things." She says the words quietly, focusing her attention on the hand she still has trapped between her own.

Santana blinks, gulps, then shoots a quick look to make sure no one else is close enough to hear their conversation.

"What kind of sex things, Britt-Britt?" She asks, feeling almost timid, trying not to admit how much the potential answer worries her. She and Brittany both have a great deal of experience when it comes to sex, so anything Brittany is actually nervous to bring up she finds an immediate cause for alarm. "I mean," she clears her throat nervously, "I think I'm pretty open minded about things."

The more Brittany starts to fidget, the more nervous she gets.

"Just, you know, things we've never tried before." She's almost mumbling now and Santana's nerves are officially climbing to dangerous levels. Because they've done a lot of things together, and the list of things not included is relatively small. She braces herself, ready to gamely try nearly anything Brittany might be curious about. So long as it doesn't involve a third party, she figures she can stomach just about anything. Within reason, that is. And maybe a few things not within reason, if Britt really wanted to try them and there was a shower very close at hand.

"We can try anything you want, Britt." She almost cringes as she says the words, praying silently that she can make good on her promise. Knowing that she probably would agree to just about anything her girlfriend wanted.

"Even if it might be a little gross?" Santana sighs, her stomach twisting slightly.

She takes one of the hands that's still fiddling with hers and uses it to pull Brittany up and then around to face her. But her cheeks are now a little more than pink and she doesn't want to meet Santana's eyes.

Now officially worried, Santana tugs her up, surprises the still sprinting Cheerios with an early reprieve and tugs Brittany down the steps and out toward her car. Brittany comes without protest, shrugging on her jacket and looking entirely too timid than she would ever be about anything related to the topic of sex. Her girlfriend has always been something of a free spirit when it comes to things like this, which is part of what lead them to hooking up secretly for the last few years before she actually admitted to herself that Brittany was all she wanted. They've done threesomes, went at it in the showers, once she even let Britt finger her in the back seat on the way to a concert when both of their dates were sitting up front talking about football.

By the time they make it out to her car, Santana decides that she's too distracted to drive. She unlocks her doors a few feet away and opens the door to the back seat, pulling Brittany in behind her and firmly onto her lap, pointedly ignoring the stares of a few teachers making their way out to their own cars.

Brittany eyes are a little wide, but she settles against Santana without protest, still looking down almost shyly even as Santana ducks her head and tries to catch her eye.

"Okay, Britt. Spill." She's too nervous now to be anything but blunt. "I promise, whatever it is, we can talk about it. I know talking isn't really our thing and everything, but really, just tell me."

Brittany squirms and sighs, glancing up once at Santana's face before leaning over and resting her head against the shoulder of her jacket.

"It's nothing really…"

"Oh, no. It's not. I promise, I won't get upset about whatever it is."

And then she waits. It takes a few minutes, because the labyrinth of Brittany's mind isn't something that can be hurried through without getting hopelessly lost. It takes time, and sometimes meticulous patience. But she figures so long as it doesn't involve permanent scarring, or the participation of Lord Tubbington, she can probably talk herself into just about anything.

When Brittany finally starts to quietly ramble, she just hangs on and waits.

"It's just that, I was thinking about something and there's a part of me that things it's kinda gross, but then I know it's kinda not because guys do it and they seem to like it a lot and I was thinking maybe it would be hot to try. I mean, it might hurt a little bit, but that can be okay sometimes too and I just thought you know if we didn't like it that would be okay because I don't want you to think we would have to do anything or anything like that, but if we did I know you have to like, prepare for it and I totally would…" Brittany looks up to see the look of utter confusion on Santana's face and quickly starts to backtrack, "but I mean, never mind. I'm sure it's a stupid idea and we don't have to.."

"Whoa… Britt." The word 'stupid' in Brittany's rant seems to shake Santana out of her stupor and she reaches up to grab her girlfriend's face with both hands. "Whoa, okay, just slow down for a second."

Stopping abruptly, Brittany's shoulders are slumped and she tugs one of her lips between her teeth as if trying to force herself into silence.

Santana's mind races for a few seconds, trying to piece together the clues. When it dawns her, she almost starts laughing.

"Are you talking about anal?"

Brittany's eyes bulge a little bit and Santana has to grab her tightly to keep her from squirming off her lap. She waits until she gets a slight nod of embarrassed acknowledgement.

The relief she feels is almost instantaneous. The arousal follows quickly. She's never given a lot of thought to the subject before, because letting a guy near her ass was somehow even less appealing than letting them do her any other way, but now that the subject is out there, spinning around her brain like a new discovery, she can't say she doesn't find it a little bit intriguing. And given all the other things that could have been Brittany's secret sexy wish, she's so far beyond relieved that she'd probably be willing to have a go at it right here and now, if they were properly equipped for the situation.

"Okay, c'mere." She tugs, pulling Brittany's compliant body until she is straddling her lap and looking her fully in the face. "We can try that, if you want."

Blue eyes rise bashfully towards hers, a small smile curling the corner of her lips.

"Yeah?"

"Totally." She smiles back. "You just need to tell me.. I mean, was this something you wanted to do to me? Or…?"

Brittany's eyes bulge again, and the color returned to her cheeks. "I didn't think about that. Would you want to try it, too?"

Santana laughs so hard her head hit the back of the seat. "I'd be open to the possibility." She grins as she says it and Brittany grins back at her in response, the sparkle back in her eyes. "But what you really want is to try it on you, right?"

Still looking a little embarrassed, Brittany's head nonetheless nods faster than a bobble head doll going over train tracks.

Wrapping her arms around strong shoulder, Santana leans forward, pressing a soft kiss on her cheek and working her lips toward a bright pink ear.

"Do you want me to fuck your ass, baby?" Brittany's whole body shivers at the words. "I think I could manage that."

Brittany pulls back nearly squealing with excitement before kissing her fiercely. Santana leans back and enjoys it. She hears catcalls from a few hockey team pervs heading out to their car and flips them off over Brittany's shoulder.

It takes a few days of planning. Including getting a little extra cash to go make the kind of purchase she could never allow to show up on her father's credit card bill. But her mom is headed to Vegas for a long weekend and when she invites Brittany over on that Friday night, she double checks the list she's got three times to make sure she's prepared.

They get take out from Breadstix, just so they can enjoy the bottle of wine at home she bribed Puck into getting for them.

The sweet, romantic dinner turned into a long, hot shower where she got on her knees and pulled Brittany's thigh over her shoulder, licking softly the entire length of her sex, nudging further back with each pass until her tongue was probing gently at Brittany's ass ever few seconds. The deep groans she heard above her were insanely hot, and Brittany's hands tangled into her wet hairs, gripping almost painfully when she tried pushing her tongue just a little inside. Before long, Britt's strong thighs were quivering around her, threatening to no longer hold her upright. Santana grinned, pulling back and standing up before taking a wash cloth and carefully giving both of their bodies a thorough cleansing.

Brittany's entire upper body is flushed, from the combination of alcohol, steam and arousal as she leads them out of the bathroom and toward her bed, covering it with clean towels before laying her girlfriend's still damp body down and crawling slowly on top of her. She enjoys the way Brittany's eyes grew darker as she watched her, feeling like a predator stalking a completely willing prey.

Holding her eyes, she leans over into her nightstand and pulled out a small assortment of objects. The blue eyes that follow her movement grew wider with each one, and she gulps nervously at the last one as it was placed beside them.

Santana pauses, trying to fight back a twinge of nerves.

"Is that okay?" She asks quietly.

Brittany doesn't answer for a moment, too caught up in staring at the new addition to their sex life. When her response finally came it was sit up quickly, mashing their lips together in a sloppy kiss before twisting around until she was the one between Santana's spread thighs.

"I get a turn too, right?" She pulled back long enough to ask breathlessly. "I mean, you don't have to… like that…. but I really want to just…" her hips pumped meaningfully into Santana's and she can only giggle at the enthusiasm.

She reaches up to still Brittany's excited movements and looks her deeply in the eye.

"You can fuck me any way you want to, Britt." Her pulse races at the positively lecherous look that covers her girlfriend's face at the offer, and Santana decides that the strap on had indeed been a wise purchase. "But," she murmurs meaningfully, reaching around clamp her hands on the firm cheeks of Brittany's ass, "you first."

The wide, almost silly smile that greeted her makes Santana want to melt into a happy puddle. The cool, wet strands of blonde hair fall around their faces, shrouding them from the world and it is easy to forget that anything existed except the two of them and the way they make each other feel.

Brittany shifts until she is straddling her hips and then sits up, grinding down into Santana with a look that somehow manages to be innocent and carnal all at once. Hands still on her ass, Santana urges her upward, stealing one last quick kiss before guiding Brittany up her body until her soft thighs are around Santana's head and she resumed the gentle licks she started in the shower. This time, she let her attentions wander back more often, teasing and probing with her tongue while the thighs around her head quiver and soft sighs and groans float down from above her.

Reaching over, she pats around until she finds what she's looking for, grabbing the tube of lubricant and popping the lid. Brittany jumps slightly at the sound, and then giggles nervously as she looks down into Santana's dark eyes.

She pulls back just enough to offer one last, "Are you sure?"

Brittany nods almost frantically and she grins, nipping at her hip as she squirts some lube onto her fingers and then slowly goes to work. The first press of her finger inside Brittany's ass goes smoothly, popping inside and causing a whimper in response. She takes her time, exploring with one finger, then two. Licking at her occasionally and enjoying the way it makes Brittany loosen even more around her. When she had three fingers inside, spreading and pumping them with an easy, gentle rhythm, she unexpectedly clamps onto her clit with her lips, causing Brittany to jerk and moan, squeezing her exploring fingers tightly before her whole body seemed to soften and open up like a dark flower blooming in the moonlight. Santana pushes as far as she could inside one last time, causing a deep, hungry groan before pulling out.

Brittany groans again at the loss, but looks down without protest as Santana squirms out from beneath her and reaches for the strap-on.

"How do you want to do this, Britt-Britt?" She asks, tugging the straps up over her hips and securing them in place. She rips open a condom and slides it on, carefully covering it in what is probably way too much lube while Brittany watches her like she's in a trance. "Britt?" She asks again, when she's ready, waiting as it seems like there are too many dirty thoughts floating around in Brittany's mind for any one of them to make its way to the surface.

Finally, her patience runs out, and she slides back over, her legs gliding back between Brittany's until as she scoots downward until her new appendage is nearly pressed between Brittany's legs. Moving her hands to her hips, she urges her upward, but instead of going too far back, she presses the round tip along the length of Brittany's sex. Unwilling to pass up the chance to tuck it inside and enjoy the way Brittany's eyes flutter closed. Soon Brittany's hips take over, pressing down firmly until she is flush against Santana's lap, the unexpectedly pleasurable pressure against her own clit makes Santana's eyes roll back, her back arching as she presses up even more firmly. Brittany is panting now, starting a rhythm with her strong hips as she begins to ride. Each motion drives Santana along with her, higher and higher. She reaches back to clutch as Brittany's ass again, letting her slick fingers explore the crevice even as it moves above her. When she presses one finger back inside, Brittany freezes, gasping in shock before she begins to shudder. She grinds down harder against the dual invasion of her body and Santana responds eagerly, pumping her finger inside much harder than she intends, but soon is rewarded by Brittany coming apart above her, slumping down over her chest. Her harsh breath tickles the sensitive skin of Santana's neck, makes her writhe endlessly, the toy strapped to her waist moving as well and causing Brittany to jerk and whimper erratically.

Not able to take the waiting any longer, Santana moves again, pulling out from under her girlfriend, leaving her slumped over as she crawls up to her knees behind her. She grabs the cheeks of Brittany's ass, spreading them slightly and taking in the slicked, softened opening between them. She chews her lip for a moment before adding one last slathering of lube for good measure before taking hold of the slippery dick and pressing it against her target.

Brittany groans again, pushing backward. She takes hold of her hips firmly, almost shocked at how much this is turning her on, and then slowly presses inside. Maybe it's the thought of what they are doing. Maybe it's the almost certainty she feels that she's the first one to be with Brittany like this. Or then again, maybe it's just because she's ridiculously in love with this girl and anything that makes her writhe and moan like this couldn't be anything less than amazing.

She hears gasps and whimpers, the sweat trickling down her neck as she waits for any sign of pain or hesitation from Brittany. After the first few inches, she goes almost painfully slow, rocking gently bit by bit until she is flush against pale, quivering cheeks.

"Oh my God, Britt." She whispers. There is a mumble of acknowledgement from beneath her, as Brittany reaches back and clutches at one of her hands. "Are you okay? Is this okay?"

Instead of answering, Brittany's body surprisingly lurches forward and then nearly slams herself back into Santana's hips, causing an explosion of heat through her groin. Her head falls back for a moment before she gets hold of herself, takes a better grip on Brittany's hips and begins her own rhythm. After a few minutes, she rocks harder, pushing and pulling them both, feeling the amazing burst of sensation every time the toy grinds into the cheeks of Brittany's ass.

"So good." She's not sure if the words are out loud, or if Brittany could even hear them. She feels like some kind of animal, rutting against its mate, pumping and jerking in a primal, timeless rhythm, faster and faster, harder and harder until Brittany is grunting and crying out every time their bodies slap together.

Surprised to feel herself lurching erratically toward an orgasm, she leans forward, reaching around to fumble for Brittany's clit. She can't manage grace, but as soon as she finds her target, Brittany's whole body jerks and spasms wildly, nearly knocking them both over as she falls onto her face, hips pumping wildly and screaming into the jumble of sheets beneath them. So close she can't stop herself, Santana plants both hands on the bed and pumps her hips over and over again until her own body jerks and seizes up, collapsing onto Brittany's strong, sweaty back.

The body beneath hers is limp, and she wonders if Brittany actually blacked out. Gathering her strength, she pulls back, wincing at the now angry red surrounding Brittany's ass. She pulls back carefully, earning a low groan as she pulls the toy out before slipping it off her hips and crawling back up to collapse beside her girlfriend.

After a moment, Brittany shifts, nuzzling into her shoulder with a few incoherent mumbling noises and planting lazy kisses across her chest.

"You okay, BritBrit?" Santana pants, waiting for her heart to quit racing.

"Mmmhmmm." She smiles at the muffled response, kissing the damp hair before laying back.

"Soon as I can feel my legs again, it's your turn."

Santana's eyes pop open widely, and she gulps and feels her own ass give an involuntary clench. But she knows she would never say no.