A/N: This was originally a fill for a prompt on the GKM. Enjoy!
Brittany hadn't always thought that Santana wanted to try anal play. But that was because Santana never really wanted to try anything new in bed. Or at least she never talked about wanting to try anything new. That was Brittany's job. Santana usually always agreed to experiment, and even more, she almost always ended up loving the new things they did. Like the first time Brittany had tried fingering her from behind. As she lightly bit into Santana's left butt cheek as she climaxed, Brittany couldn't help but internally smile at the fact that Santana had never come so hard before.
Santana's ass had always been Brittany's favorite part of her body. It was one of the main reasons that she liked when Santana rode her fingers while sitting in her lap. That position meant that Brittany could run a hand down Santana's spine to her ass. It meant that she could squeeze and knead Santana's ass, pulling sweet, soft moans from both of them.
It was in this position, with Santana slowly riding Brittany's fingers above her, that Brittany first realized that Santana might want to try anal play. In time with Santana's slow speed, Brittany ran her free hand across every inch of Santana's sweat slick ass before she made her way to the middle where she ran her pointer finger up the first couple inches of the crack. Santana whimpered as her whole body shuddered and she began to ride Brittany's fingers just a little bit faster. Brittany's focus shifted between Santana's eyes and her own soaked fingers as Santana took them all the way in before lifting her hips and repeating the action all over again.
Once Brittany felt that she was no longer in danger of coming at the satisfying wet sound that filled the room every time Santana dropped down on her fingers, she ran a free finger up the very top of Santana's crack again. Santana let out a strangled moan as she fell forward, breaking her fall by grabbing Brittany's breasts. Unable to keep a slow pace, Brittany began thrusting her fingers up into Santana harder and faster. Santana met Brittany thrust for thrust, not slowing until her walls clamped down around Brittany's fingers.
Once Brittany and Santana had caught their breath, they started giggling softly as they looked at each other. They repositioned themselves so that they were lying side by side.
"That was really good, Britt," Santana breathed. An airy smile played on Brittany's lips as she stroked Santana's cheek.
"Good. I didn't know you liked that." At this, Santana tried to hide her rosy cheeks by turning her head into her pillow. But Brittany would have none of that.
"What's wrong, baby? Don't get shy on me," Britt said as she pinched the tip of Santana's nose. Santana couldn't meet Brittany's eyes. So instead she ran her fingers over Brittany's collarbone.
"Nothing. Nothing's wrong. I just—I don't—It's not that I'm into that… I think just being with you made it feel good."
Now it was Brittany's turn to blush. "Oh… I thought—It seemed like you liked it…"
Santana did not respond. She just continued running her fingers along Brittany's collarbone. Sensing Santana's shyness and not quite believing that she hadn't liked it, Brittany tried a different approach.
"Well, I liked it. You were so hot, Santana. Maybe we can try it again sometime?" Santana swallowed audibly, eyes still focused on Brittany's collarbone. "And maybe next time I could go further down, you know?"
There was still no response from Santana, but Brittany didn't want to give up just yet. "Like…maybe next time I could actually touch your—"
"Britt!" Santana gasped out in shock as she finally met Brittany's bright blue eyes. "I don't—that's not something I want to do."
Brittany didn't buy that for a second, but she also didn't want to upset Santana, so she backed down. The conversation ended with a kiss to Santana's forehead and a suggestion that they take a quick nap.
Brittany thought that she would get the chance to bring the topic of anal play up again, but it hadn't worked out that way. Every time she'd tried to bring it up, Santana artfully changed the subject. She tried to just go for it again when they were having sex, but Santana would move Brittany's hands anytime they got anywhere near her ass.
Brittany was about ready to give up a few weeks later when Santana paused the Sweet Valley High DVD to tell her she was leaving town for New Year's Eve.
"What!" Brittany screeched.
"Yeah… My parents just told me last night. I guess my aunt's kind of pissed because she hasn't seen me in two years," Santana said from her position in between Brittany's legs. Brittany let this new information sink in for a minute before she sighed and relaxed against the couch.
"Bummer. You're gonna miss Rachel's New Year's Eve party."
"Oh, what a shame," Santana said as she rolled her eyes. Brittany giggled at her girlfriend. She knew Santana liked Rachel more than she'd ever dare to let on.
Santana's eyes brightened as she seemed to remember something. "Oh, and there's an upside to all of this!"
"Yeah?"
"Yeah! I'm going to have a room all to myself this year," Santana said as she began to draw circles on Brittany's thighs with her fingers.
"Is that so," Brittany asked with a teasing coyness to her voice.
"Uh-huh," Santana said as she turned her head to smile at Brittany. And you know what that means…"
"Nope, uh-uh. What does that mean, Santana?"
"It means that you can, you know, call me at night."
Deciding she wasn't done playing, Brittany said, "I couldn't have called you if you were sharing a room?"
Santana rolled her eyes and laughed as she playfully slapped Brittany's thigh. "Stop it, Britt! You know exactly what I'm trying to say."
The room suddenly felt 30 degrees warmer as Brittany ran her hands over Santana's and kissed her at the base of her neck.
"Okay, baby. I can't wait to call you."
As Santana snuggled closer into her, Brittany couldn't stop thinking about how perfect this situation was. It would be way easier to make Santana feel comfortable with exploring anal play during phone sex. At least she hoped so.
A few weeks later, Santana left Lima for her aunt's house. Brittany headed straight to the drugstore after they had said their goodbyes. She needed lube if her phone sex date with Santana was going to go as planned.
Brittany waited until her sister and parents went to bed before she called Santana. It started off like a normal conversation—they talked about how their days were and how much they missed each other. Things started to get a bit more heated when Santana complained about being cold in the guest room and Brittany offered to help her warm up. Brittany knew that Santana was going to have to be super turned on for Brittany's plan to work. So she worked her up for a few minutes and made Santana put the phone to her sex so she could hear the sound her fingers made as they made contact with her wetness. When Santana asked Brittany what she was doing to herself, she knew it was time to put her plan into action.
"I'm touching myself," Brittany breathed out.
Santana let out a quiet moan of approval before asking, "Where? Where are you touching, Britt?"
"Guess." It was always fun to tease Santana and that was exactly what Brittany planned to do tonight.
"Mmm, I bet you're tugging at your nipple. The right one, 'cause it's more sensitive."
"Nuh-uh. Lower. Much lower."
"Are you rubbing your clit?"
"Nope. Lower," Brittany hummed. She was beginning to worry that she was going to ruin her plan by coming before Santana even guessed what she was doing to herself.
"You're inside already, Britt?" Santana chirped.
"No, baby. Lower."
Silence.
Brittany had expected a moan or a question, but not complete and utter silence.
It took a few seconds for Santana to speak again in a very tentative and shy voice. "Are you touching your… What are you—what are you doing exactly?"
Brittany was relieved that her plan seemed to be working. "I'm making really light circles around the hole with my pinkie finger. It feels so good," she breathed out. "I'm so sensitive there." Brittany could have sworn she heard Santana try to hold back a moan before she started to speak again. "It feels so good. So much better than I thought it would. It's making me so wet; I wish you were here to see this, baby."
Santana swallowed audibly and all that could be heard on the line for a few seconds were Brittany's soft pants.
"What are you doing now? Are you still making circles?" Santana finally asked. Her increased excitement served to turn on Brittany even more.
"I want to—Ah," Brittany moaned. "I want to put my finger inside."
"Won't that hurt, Britt?" Santana asked in a high-pitched, slightly cracking voice.
"No, no. Don't worry; I bought—I'm using lube," Brittany barely managed to get out. It was getting harder and harder for her to concentrate on talking. "I'm gonna do it. I'm gonna put my finger in."
Brittany was unable to control her moan or the arching of her back as she slowly slid her pinkie into her hole. "God, Santana. It feels so, so good! I wish you were here; I wish you were doing this to me." Brittany was panting harder now as she rapidly approached her climax.
"I wish I was there too, baby," Santana moaned out. "Pull—pull your finger out and push it back in."
Brittany did as she was told, slowly at first to avoid pain. As she got more comfortable, she began to pick up speed. "Oh, Santana! It feels so good—Ah! Are you touching yourself too?" Brittany didn't need to even ask that question. She could hear the tell-tale wet sounds of Santana fucking herself over the phone.
"Yeah, I am," Santana panted. It was getting harder for her to speak, too. "I'm rubbing my clit and fingering myself." The sound that came out of Brittany's mouth at the admission made Santana's clit throb even more than it already was. "Could you—I mean, would you want to—Can you…"
When it was clear that Santana was having trouble completing her request, Brittany decided to encourage her. "Can I what, baby? What do you want me to do?"
After a couple seconds, a shy but extremely turned on Santana said, "Could you put the phone between your legs? I want to hear what it sounds like."
Brittany had to stop moving her finger and squeeze her legs together in order to not come at the request alone. She did as Santana asked and with a fumbling hand put the phone on speaker before resting it between her spread legs. After applying more lube to her finger, Brittany continued thrusting her pinkie into her hole and began rubbing her clit in tight circles with the middle and ring finger of her free hand.
The sound of Brittany's wetness and the thrusting of her lube-covered finger were like music to Santana's ears. She just couldn't get enough. "Faster," she begged. "Go faster, Britt. You sound so hot."
Brittany's eyes fluttered closed as she followed her girlfriend's instructions. When she felt she no longer had any control over what her hips were doing, she knew she was close. "I'm gonna—I'm gonna come," she moaned.
"Me too, baby," Santana replied. "I'm so close." She paused to catch her breath. "Come for me, Britt."
That was all Brittany needed to hear. Her hips jutted forward and upwards a few times before her whole body momentarily stilled as her climax took over. Brittany's body began to shudder as she rode out her orgasm. She loved the new yet familiar feeling of her pinkie finger being squeezed inside of herself. Brittany was so caught up in her own climax that she did not even realize that she'd missed Santana's own. All she heard was the heavy panting of the aftermath.
Brittany wanted to know how Santana liked what they'd done, but she didn't want to scare her again, so she settled on, "That was so hot, Santana."
"Yeah," Santana said, still trying to catch her breath. "It really was, Britt."
"Mmm, I'm glad you liked it."
"Yeah," Santana said, nervousness evident in her voice. "Do you think we could maybe try that again sometime? When we're together?"
Brittany couldn't help the bright smile that overtook her face. "Sure, baby," she whispered. "I can't wait."