Day 13 - Anal Strap-on/First-Time Anal

Day 13 - Anal Strap-on/First-Time Anal

The atmosphere in their hotel room was soft, intimate. They had just come back from dinner, and the quiet hum of the city outside was the only sound in the room. This was the first vacation they had actually managed to schedule and take without being called back into work. It was the perfect setting to try something new.

It started with a few teasing touches at dinner, a playful hand on JJ's thigh under the table, a smirk shared as Emily whispered something dirty in her ear. They loved the tension, the subtle hum of arousal and need that seemed to permeate the air between them whenever they weren't working. It was how they dealt with things.

Were they sex addicts?

Garcia had certainly given them pamphlets about it after catching them using her bathroom for sex during her Halloween party, but who in their line of work didn't need an outlet. And it was not like it was all safe, sane, and consensual.

JJ was already naked, lying on the bed, her body draped in a thin sheet, her golden hair spread out over the pillow within one minute of being back in the room. Momma grizzly was eager tonight. Her girlfriend sat at the edge of the bed, gazing down at her with a soft smile. She couldn't believe how lucky she got sometimes. "Are you sure you want this, love?"

The blonde woman smirked up at Emily. The older woman was normally the one that took control in the bedroom, though not always. She was still always so soft to begin with. No matter what scene they were going to go for, whether erotic roleplay or some good old fashion BDSM, Emily always checked in with her partner first.

"Yeah." JJ smiled into the word. There wasn't even a tiny part of her that didn't want Emily. "I want you to. I trust you."

The brunette's hand moved up, gently cupping the other woman's cheek and brushing the soft skin with her thumb. "We'll take it slow," she promised, her voice full of tenderness. She pressed a soft kiss to JJ's lips before she sat up, reaching for the bedside drawer.

The younger woman's heart pounded as she watched Emily pull out the strap-on, the one they'd used before, but tonight it wasn't just for JJ's pussy. Tonight, Emily was going to be her first for anal. Every guy she had ever dated had wanted it. They were seriously obsessed with her ass. Perhaps it was because of how perfectly muscular it was because of running and soccer, or maybe it was a domination thing. Either way, JJ had had no interest. But with Emily, as with all things, this was different.

As Emily slipped the harness on, her eyes stayed locked with JJ's, that gentle dominance Emily always exuded wrapped around the other woman like a warm blanket. She felt safe. She felt cared for. The blonde woman trusted her partner implicitly—trusted her to push her boundaries, to take her somewhere she's never been, and to keep her safe while doing it.

Once the strap-on was in place, Emily climbed onto the bed, positioning herself between JJ's legs. Her fingers trailed down JJ's inner thighs, teasing her, making her body ache for more. "Relax for me," Emily whispered, her voice low and soothing as she gently spread the blonde's legs wider. "I'll take care of you."

JJ let out a soft breath, her body already starting to relax under Emily's touch.

Emily's hand moved lower, her fingers gently parting JJ's folds as she found her clit, rubbing it in slow, soft circles. JJ moaned softly, her hips instinctively arching up into Emily's touch.

"Just like that," Emily murmured, her fingers tracing lazy patterns on the sensitive nub. "Let your body relax."

JJ's body responded to Emily's soothing touch, her muscles relaxing as Emily's fingers expertly worked her clit, building the pleasure but keeping it gentle. "Em…" the younger woman gasped softly, her body already trembling with need.

The brunette smiled, her free hand slipping through the other woman's folds, collecting as much of her arousal on her singular digit as possible "You're doing so well," Emily praised, her voice full of warmth as her finger slipped between her cheeks to the tight ring of muscles, not yet pushing inside. "I'm going to stretch you out first, okay?"

JJ nodded, her breath coming a little faster as she felt Emily's finger gently press against her tight entrance, pushing just the tip inside. Emily moved slowly, only allowing the first knuckle of her slicked index finger to push in. The whole while she kept working her partner's clit, no longer just making lazy patterns but spelling out naughty words, each pass over her clit a letter spelt out only by touch.

"Tell me if it's too much," Emily murmured, her voice soothing as she slipped her finger up the second knuckle.

The blonde's body tensed slightly at the unfamiliar sensation of Emily's finger inside her. But it wasn't uncomfortable. It just made her feel full in a different way. "I'm okay," JJ whispered, her voice trembling as her body adjusted.

Emily smiled, pressing a soft kiss down on her lover's lips as she reached for the lube on the bedside table. Quickly uncapping it, she added some to the finger slowly rocking into JJ as well as two more. She had plans tonight, and JJ was going to need to be really ready for them.

"That's my good girl," Emily cooed, her voice full of affection as she started to let a second finger slip in. She had a feeling the blonde was going to like this. They had never played with insertion before back there, but Emily had used her tongue on occasion and every time her lover went practically feral at the sensation.

JJ's moans grew louder as her body started to adjust, the pleasure from the older woman's fingers on her clit helping her relax even more. "God, Em… that feels so good…"

Emily grinned, her fingers moving a little faster, stretching JJ more as her other hand palmed JJ's clit, making her gasp. "You're so beautiful like this," Emily murmured, her voice full of awe as she watched her lover's body react to her touch. "You're taking it so well."

"I need you…" JJ gasped, her hips arching up into Emily's touch. "Please, Em… fuck me with your cock."

Emily's eyes darkened with desire. She loved hearing the younger woman beg for her, loved the way her body responded to every touch, every command. She was built to submissive the way she begged for her strap. "Not yet," Emily whispered, her voice low and full of control. "I need to add one more finger, and I want you to come for me first. Get your body all nice and relaxed for me."

With that, Emily worked in one more finger, not bothering to take as much time to let her stretch. JJ's body was accepting her fingers without protest, letting them take her deep. They sucked them in as if they never wanted the brunette's fingers to leave.

"Come for me," Emily murmured.

The blonde was helpless but to obey. Her body arched off the bed, her head tipping back as the orgasm hit her hard, her entire body trembling with the intensity of it. She cried out, her hands gripping the sheets as wave after wave of pleasure crashed over her.

Emily's fingers kept moving, working her woman's body through the orgasm until she was shaking, her breath coming in short, ragged bursts. When the other woman finally came down from the high, her body slumped back against the bed, her chest heaving as she tried to catch her breath.

"Good girl," Emily whispered, a smugness in her tone as she slowly withdrew her fingers. "You did so well."

JJ's breath was still shaky, her body still trembling from the aftershocks of the orgasm, but she wasn't done. She needed more. "Please, Emily…" JJ whispered, her voice trembling. "I need you."

Emily's eyes darkened at JJ's words, her body already responding to the desire in JJ's voice. "I've got you," Emily whispered, her voice low and full of promise as she reached for the lube, coating the strap-on before positioning herself behind JJ.

"Relax for me," Emily murmured as she pressed the tip of the strap-on against JJ's entrance, her hands gently gripping her lover's hips. "I'll go slow."

The blonde's breath hitched as she felt the strap-on press against her, her body tensing slightly with anticipation before forcing herself to relax. She knew it would hurt if she didn't relax for it. They had watched enough of those videos together on JJ's phone while working their heads out of work mode and into something more pleasant. JJ had always noticed how the girls practically moaned for it when they relaxed.

The older woman moved slowly, the tip of the strap-on pushing inside just a little, stretching JJ in a way she'd never felt before. "That's it," Emily whispered, her voice soothing as she gently worked the strap-on deeper, inch by inch. She kept her hand on the other woman's hip, using her thumb to make soothing circles.

"God, Em…" JJ whined, her hips bucking. "It feels so good…"

Emily grinned, her hands tightening on JJ's hips as she thrust a little deeper, the strap-on filling her completely. "You're taking me so well," Emily murmured, her voice thick with desire as she started to move, her hips rocking against JJ's, slow at first, then harder as JJ's body relaxed into it.

"Fuck, Emily…" JJ moaned, her body trembling as the strap-on stretched her in ways she'd never imagined. "I need more…"

"More?" Emily's voice was thick, teetering into her work 'I am badass FBI Agent Emily Prentiss' voice. The blonde moaned immediately. She loved that powerful, in control voice. Emily was all too happy to oblige. She loved the way her girlfriend begged, loved seeing her usually strong and composed partner unravel beneath her. With a smirk, she thrust her hips a little harder, the strap-on sliding deeper into JJ's ass. The sound of JJ's sharp intake of breath spurred her on, her hands tightening on the other woman's hips as she started to pick up the pace.

JJ's head dropped to the pillow, her body trembling with every deep thrust. The pressure, the way Emily filled her, was like nothing she'd ever felt. It was intense but so good. "God, yes, just like that," JJ gasped, her fingers gripping the sheets as she tried to ground herself in the overwhelming sensation. "Don't stop."

Emily chuckled softly, thanking the universe for her fitness. She could keep this up even when JJ was a moaning mess beneath her, three orgasms in, which the dark haired agent was hoping for tonight. "You're such a good girl," Emily praised, her nails dugs into the soft flesh at JJ's hip, marking her. "Taking me so well."

The praise only made JJ's body react more intensely. Every nerve in her body was on fire as Emily stretched her out, the pleasure intensifying with every thrust. She could feel the heat building inside her again, coiling tighter and tighter in her core.

Emily's hands moved up, gently tugging at JJ's hair, pulling her head up just enough so that she could lean down and press a kiss to the back of her neck. "You want to come again, don't you?" Emily whispered, her voice dark and full of promise.

JJ let out a shaky breath, her body trembling as she nodded. "Yes, fuck, yes…"

Emily's hand slid back down JJ's body, her fingers finding her clit again, rubbing it hard and fast circles as she continued to thrust into her. The combination of sensations—the fullness of Emily inside her and the pressure on her clit—was overwhelming.

"Fuck, Em, I'm so close…" JJ moaned, her voice breaking as her body started to tighten again, the pleasure threatening to tip her over the edge. She felt so full, so utterly claimed, and she never wanted it to stop.

The older woman grinned pushing her full weight into each thrust. "Come for me," she growled softly, her voice filled with command as she leaned down, biting gently at JJ's shoulder. "Come on my cock, Jen."

The roughness in Emily's voice, the way she said "my cock," pushed JJ over the edge. With a strangled cry, the blonde's body arched off the bed, her entire body trembling as the orgasm crashed over her, wave after wave of pleasure tearing through her.

"That's it, baby," Emily whispered, her voice low and full of satisfaction as she slowed her thrusts, her fingers still rubbing gently over JJ's clit. "You're doing so well."

JJ's body slumped forward, her cheek pressing into the pillow as the aftershocks of the orgasm rippled through her. She felt utterly spent, her breath coming in shallow gasps as she tried to catch her breath.

The dark haired woman slowly withdrew the strap-on, leaning down to press soft kisses along her girlfriend's back as she moved her slowly. JJ's legs were still trembling, her body still humming with the aftershocks of the intense pleasure.

"You okay?" Emily asked softly, her voice filled with concern and affection as she cupped JJ's cheek, brushing her thumb gently across her skin.

The younger woman nodded, her breath still shaky but a small smile tugging at her lips. "I'm better than okay," she whispered, her voice full of warmth as she looked up at Emily with half-lidded eyes. "That was… incredible."

Emily grinned, leaning down to kiss JJ softly, their lips lingering in a soft tease. "You liked anal," she whispered against JJ's lips, her hand resting gently on JJ's thigh, stroking her skin soothingly.

JJ chuckled softly, her body still trembling as she let out a contented sigh. "I think I'm going to feel that for days," she joked, her voice light and teasing as she looked up at Emily.

Emily laughed, pressing another kiss to JJ's temple. "Good," she murmured, her voice low and affectionate. "That was the plan. Although we could keep going…two is such a low number for you."

The blonde whined, swatting at the other woman's hand which had started to edge closer to her center. "I can't…"

"Fine, fine," she chucked. Though if they had not just introduced something new, she would've kept going until her girlfriend used her safe word. 'Not now' and 'no' were more suggestions unless the safeword was invoked in their bedroom and then everything stopped.

They lay there in silence for a few moments, their bodies still pressed together, the afterglow of their lovemaking wrapping around them like a warm blanket. Emily's hand continued to gently stroke JJ's skin, soothing her as she came down from the intense high.

"I love you," JJ whispered, her voice soft but filled with emotion as she gazed up at Emily, her fingers reaching up to brush a strand of hair from Emily's face.

Emily's eyes softened, her smile full of affection as she pressed a gentle kiss to JJ's lips. "I love you too," she whispered back, her voice full of warmth and sincerity.

They stayed like that for a while longer, wrapped up in each other, before Emily finally shifted, moving to grab a towel from the bedside table. "Let me clean you up," Emily said softly, her voice full of care as she gently wiped down JJ's body, her touch gentle and soothing.

JJ let out a soft sigh, her body completely relaxed as she let Emily take care of her. "Thank you," she whispered, her voice full of affection as she smiled up at Emily.

Emily smiled back, her eyes filled with love as she pressed another soft kiss to JJ's forehead. "Anytime, you know I will always take care of my momma grizzly."