Summary: Brittany wonders what it's like to be a gay guy, so Santana lets her strap-on fuck her in the ass.
It all starts after Kurt breaks up with Brittany. After sighing heavily for about half an hour over the loss of the most sensitive, caring, and non-sex-obsessed "boyfriend" she's ever had, Brittany's attention turns elsewhere. Unfortunately, in this case, "elsewhere" does not mean "Santana's boobs." Rather, she becomes fascinated by gay men — specifically, by how they have sex.
They're lounging on Santana's bed, sort of watching Jersey Shore, when Brittany suddenly speaks. "Do you think Kurt would like me better if I was a guy?"
Santana doesn't even look away from her phone. "Yup."
Brittany rolls over to look at her. "Why?"
Glancing up, Santana raises her eyebrows at her best friend. "Because then you would have a dick."
"Hmm." Unable to argue with that logic, Brittany rolls onto her back again. After a long pause, she muses, "If I was a boy, I think I'd be gay."
"Oh, yeah? Why?"
"Because I'd probably still like penises. You know?"
Actually, Santana doesn't, but she can understand the sentiment. "I guess."
"But I like girls too, so maybe I'd be bi."
Santana laughs. "So you'd be a bi guy?"
Brittany giggles, and thinking the subject is finally over, Santana returns her attention to her phone. However, a few minutes later, Brittany speaks up again. "Did you know that people write these stories online about TV shows and stuff?"
"Really?"
"Yeah, I was reading some the other day. They were all about the guys from Supernatural being gay together."
"Huh." That's kind of bizarre. Some people really have no lives whatsoever.
"Yeah, it was weird. Anyways, they kept talking about how one guy was a top, and one guy was a bottom. Like, one guy likes to take it in the ass, and the other guy likes to give it."
"Huh," Santana says again, not sure where this is going.
"So I was thinking, if I was a gay guy—"
Santana groans. "Really, Brittany?"
Brittany pouts at her, then continues. "I don't think I'd want to be the bottom, because I tried anal that one time, and it sucked."
Santana looks at her. "That was Chad, right?"
"Ugh, yeah." Brittany rolls her eyes and nods, but Santana looks thoughtful.
"He kept trying to get me to do that too. I swear that guy's obsessed. Maybe he's gay."
"Maybe." There is a long pause as both girls contemplate the possible sexual orientation of a mutual hookup. Brittany really doesn't want to let her idea die, though. "So I thought maybe I'd want to be the top."
"Okaaaay…" Santana is starting to get an idea of where this subject might be headed.
"I'm not sure, though, because I've never fucked someone in the ass before, so I was thinking—"
"No."
The blonde pouts again. "You didn't even let me finish."
"I know what you're going to say, and I can tell you right now that the answer is no."
Brittany's blue eyes slowly widen. "Are you psychic?"
For one brief moment, Santana considers saying yes, just to distract her. "No. And the answer is still no."
"What number am I thinking of?"
"I told you, I'm not psychic."
Roughly 20 minutes later, a fully nude Santana is watching as Brittany, already wearing a strap-on, pulls on a latex glove.
"I'm…not sure about this," Santana says.
Brittany turns to her with a seductive smile on her face. "Just relax," she purrs, then leans down to kiss the brunette.
Santana tries, she really does. At first, it's easy; making out with Brittany and having her boobs felt up always helps her relax. When Brittany's hand dips down south, however, she starts to tense up again.
"Relax, baby," Brittany reminds her, then kisses her again, hot and heavy with lots of tongue. Brittany gently bites her lower lip and pinches her nipple, getting a soft moan in return, then pulls away. Santana watches with hooded eyes as Brittany slathers lube all over the glove.
"I—" Santana starts to say, then squeaks when the other girl runs a cold, lubed finger down her slit.
"Are you okay?" Brittany whispers, her breath warm on Santana's lips.
"That's really fucking cold," Santana whispers back.
"How about this?" the blonde asks, starting to make gentle circles on her clit.
"Oh fuck," Santana moans. "Yes, m-much better." As Brittany increases the pace and pressure, Santana feels herself clenching around nothing, desperately wanting more. "Britt, please."
"Are you ready?"
"Yes. Please. I want you inside."
Suddenly, Brittany's hand disappears from her clit. Santana opens her eyes to see the blonde applying more lube to the glove.
"Britt, hurry u — AAAHHH!" Brittany's finger suddenly plunges knuckle-deep inside her ass. Her face contorting in both pleasure and pain, Santana clutches at Brittany's arms, her toes curling. It stretches and burns in a deliciously painful way.
"I thought it'd be better if I didn't give a warning, like when you get a shot," Brittany says innocently.
"Hnnnnnggh." Santana's only answer is a half-groan, half-moan.
After giving her a few minutes to get used to the feeling, Brittany starts to gently move her finger in and out. Santana's eyes flutter closed again as her stomach clenches, and her gasps, pants, and moans fill the room. Suddenly, it's stretching and burning in all the right ways, and when Brittany slowly slides in another finger, Santana makes a noise that Brittany has never heard before, deep in her throat. Curious, she makes a scissoring motion with her fingers, and Santana makes that noise again — a groan that seems like it's being torn out of her.
"God, Brittany, I…mmm…Jesus! Fuck, just…" Apparently, having two fingers barely moving inside her ass has rendered Santana completely incoherent. Fascinated, Brittany starts to rock her hand, slowly thrusting in and out. Santana's head lolls as her back arches, and she immediately starts rolling her hips to meet Brittany's hand. "Holy…ugh, God…Britt!"
Brittany's barely touching Santana, and she's already at the part where she can only say one syllable at a time! Shifting to get a better angle, Brittany suddenly realizes how wet she is. She doesn't want to take this slow; she wants to take Santana now.
As Brittany pulls her hand out, Santana groans again and cracks one eye open. The blonde is hurriedly pulling off the glove and trying to open the bottle of lube at the same time. "Put a condom on," Santana manages to gasp out. At Brittany's confused look, she clarifies, "I'm not putting that through the dishwasher again."
"Oh yeah, your mom was pretty pissed." Brittany giggles at the memory, then yanks open Santana's nightstand drawer and snatches a condom. As quickly as possible, she rolls it on and pours an egregious amount of lube into her palms. Grabbing the strap-on, she starts to spread it. Santana bites back a moan at the sight: Brittany, jacking herself off with both hands, her eyes desperate and wild and fixed on Santana's.
When everything is prepared to her satisfaction, Brittany grabs Santana's hip with one hand and angles the strap-on with the other. With one quick roll of her hips, she plunges halfway in. Santana's head flies back, and she screams. Really, honestly screams. Her eyes are squeezed shut, but they snap open when Brittany begins to ease the rest of the dildo in. Santana feels like she's splitting apart in the best way, her body stretched and full in a way she has never felt before. When the strap-on is finally all the way in, buried deep in her ass, Brittany's pubic bone brushes against Santana's clit, and she shudders and comes hard with a cry.
Brittany is so shocked that she stops moving for a second. Did Santana really just…? But all of the signs are there: Santana is moaning loudly and gasping for breath like she just ran a marathon, her eyes are shut tight, her thighs clenched, her hands clutching the sheets tightly, her toes curled. Her orgasm seems to go on forever, her sounds of ecstasy echoing through the room as Brittany slowly thrusts back and forth and rubs her clit with the lightest of touches.
Finally, as aftershocks shiver through her, Brittany stops moving, her own arousal trickling down her thighs. Suddenly, she has the best idea ever. She pulls out all the way, and Santana moans. "Roll over," Brittany whispers, and Santana scrambles to obey, legs flailing wildly. In no time at all, she's on her hands and knees, still panting heavily as she presents herself to Brittany. Taking a second to appreciate the sight, Brittany palms and squeezes a firm buttock, moaning at the feeling. Then, getting to her knees, she grabs Santana's hips and thrusts deep into her ass once again.
Santana immediately falls to her elbows, burying her face in the sheets. She gives another one of those crazy moans, spurring Brittany on. It takes a few tries to get the rhythm right, but soon, Brittany is thrusting hard and fast, pulling a wild groan or moan out of Santana each time she bottoms out inside of her. For her part, Santana just tries to match Brittany stroke for stroke. She can feel another orgasm building inside of her, so big that it might kill her. The indescribable fullness inside of her, the slap of her thighs against Brittany's, and the hands on her hips, pulling her roughly backwards to meet every push, are almost more than she can take.
Brittany is actually listening so closely to the noises Santana is making that her own orgasm takes her by surprise. She thrusts erratically, grinding herself against the strap between her legs, as wave after wave of pleasure washes over her. As she comes, her arousal drips down her legs, almost certainly making a mess of the sheets.
Finally, after trembling with the last of her aftershocks, she takes a deep breath and resumes thrusting. She begins to speed up, and immediately, she can hear the difference in Santana's voice.
"Ohh, Britt…ah…oh…oh!…OH!" Santana is getting close, and Brittany reaches around and thumbs at her clit. She circles it once, twice, then pinches it hard, and, with a muffled scream ripped from deep inside her chest, Santana comes so hard she blacks out for a little while.
When she awakes, she is sprawled loose-limbed on the bed, face down and ass up, and Brittany is worriedly checking her pulse.
"'m fine," she mumbles. She wants to bat Brittany's hand away, but her arms and legs have mysteriously turned to rubber.
"Okay," Brittany says, slightly dubious. Still, she retracts her hand and begins to fumble with the straps around her waist. Santana watches with one eye, still enjoying the complete and utter relaxation in all of her muscles. Once Brittany has removed the harness and tossed it aside, she turns back to the exhausted brunette. "Hey." She smiles.
"Hey," Santana murmurs.
"You just came really hard."
"I know."
Later, they sit at Santana's kitchen table, eating popcorn and (in Santana's case) shifting around to try and find a comfortable way to sit on a bag of frozen peas.
"Y'know," Brittany says, breaking the companionable silence. "I really can't believe how hard you came from anal."
"Shut up, Britt."
"Like, seriously. I'm gonna make a Glist, except instead of a Glist, it'll be 'The List of Things That Make Santana Come Super Hard,' and number one will be anal."
"I'm serious, Brittany. Knock it off."
"Fine. But next time, I want—"
"There isn't going to be a next time, Brittany."
"Okay, fine," Brittany says. Really, she's thinking to herself, Santana is such a difficult bottom, it's a good thing she's such an understanding top.