Day 5: Anal Sex/Strap-On

Day 5: Anal Sex/Strap-On

Ava stood in front of the bed, her heart pounding in her chest as she stared down at Deborah, who was lying back against the pillows with a smirk on her face. The room was dimly lit, casting soft shadows across the space, but the tension between them was palpable. Ava's fingers twitched with excitement as she adjusted the strap-on around her waist, the harness snug and secure against her hips. This was something she had been waiting for, begging for, for months , and now it was finally happening.

Deborah, of course, had been playing coy about it the entire time. Teasing Ava, pushing her buttons, always making her work for it. But tonight was different. Tonight, Deborah had given in, and it wasn't lost on Ava that this was a birthday present—a gift she had been dreaming about for what felt like forever.

"Happy birthday to me," Ava muttered under her breath, her voice thick with anticipation as she ran a hand over the silicone shaft of the strap-on. "I can't believe you're finally letting me do this."

Deborah chuckled softly, her voice low and full of amusement as she leaned back against the pillows, crossing her arms over her chest. "Well," Deborah drawled, her eyes gleaming with mischief, "I figured you've been begging long enough. Might as well see what all the fuss is about."

Ava grinned, her heart racing as she stepped closer to the bed. "Oh, you're gonna see," Ava teased. Her voice was playful. "I've been practicing for this. You're gonna love it."

Deborah raised an eyebrow, her smirk widening as she glanced down at the strap-on Ava was wearing. "Practicing, huh?" she teased, her voice dripping with sarcasm. "I'm almost scared to ask who you've been practicing on."

Ava huffed, rolling her eyes but unable to stop the grin from spreading across her face. "Relax," Ava soothed, grabbing the bottle of lube from the bedside table. "I've been... studying. And, trust me, I know exactly what I'm doing."

Deborah's smirk deepened as she shifted slightly, her body relaxing into the bed. "Ah so that is why I found 'Princess Gets Her Ass Railed by Mistress Chloe' in your browsing history" Deborah teased. "You know I'm not going to make things easy as Princess ."

Ava's cheeks colored. She knew she shouldn't have done that on Deborah's laptop but her downgraded phone didn't exactly allow for porn watching. "I wouldn't expect anything less."

The younger woman squeezed a generous amount of lube onto her fingers, her eyes locked on Deborah as she stepped closer to the bed. Deborah watched her with hooded eyes before turning over onto her stomach so as to give Ava more room to maneuver. "So," Deborah said, her voice low and almost purring, "you've been begging for this for months. Let's see if it's worth the wait."

Ava's hands trembled slightly as she knelt on the bed, her fingers slick with lube as she ran them lightly over Deborah's skin, teasing the soft flesh of her ass. The sight of Deborah, so relaxed and yet so in control, made Ava's heart race even more. "You're gonna love this," Ava whispered, her voice full of promise as she gently pressed her fingers between Deborah's cheeks, spreading the lube carefully.

Deborah let out a low hum of approval. "You're already doing better than I expected," Deborah praised, though there was a teasing edge to her voice. "But you haven't even started yet. I guess that shows how confident I was in you."

Ava grinned, her fingers moving slowly with care as she circled Deborah's entrance, pressing just lightly enough to tease her without going too far. "Don't worry," Ava whispered, her voice low and thick with anticipation. "I am going to wow you."

Ava slowly pushed a finger inside, her breath hitching slightly at the tightness. She went slow, careful not to rush, knowing how important it was to make sure Deborah was fully ready for what was coming next.

Deborah's breath caught slightly, her body tensing for just a moment before she relaxed again, her eyes fluttering closed as Ava worked her fingers deeper. "Mmm," Deborah hummed, her voice low and full of satisfaction. "I've gotta admit, you're not half bad at this."

Ava bit her lip, her fingers moving with slow, careful precision as she added more lube, easing a second finger inside. The wetness made it easy to slide in, but Ava took her time, wanting to make sure Deborah was as comfortable as possible.

"You like that?" Ava whispered, her voice thick with excitement as she curled her fingers inside Deborah, feeling her body respond to the touch. "Feels good, right?"

Deborah let out a soft, satisfied moan, her hips rocking slightly against Ava's hand as she adjusted to the intrusion. "You're getting cocky again," Deborah shot back, though her voice was strained with pleasure. "Don't think you've won me over just yet."

Ava grinned, her fingers pressing deeper as she worked Deborah open, the slickness of the lube making it easy to stretch her. "Oh, I know I've got more work to do," Ava whispered, her breath coming in short, shallow bursts as she watched Deborah's body react to her touch. "But I'm just getting started."

Deborah chuckled softly, her hips rocking slightly as she adjusted to the feeling of Ava's fingers inside her. "You'd better hope you've got more in you," Deborah muttered, her voice low and teasing. "Because right now I'm not impressed."

Ava's heart pounded in her chest, the excitement of the moment almost overwhelming as she added a third finger, stretching Deborah even more. The tightness around her fingers, the slick heat of Deborah's body—it was everything Ava had imagined and more.

"Deborah..." Ava whispered, her voice full of awe as she worked her fingers deeper, feeling Deborah's body tighten around her. "You're so... tight."

The older woman let out a low groan, her hips rocking harder against Ava's hand as she adjusted to the sensation. It felt surprisingly good the way her fingers curled. "Just wait until you use the strap," Deborah whimpered, her voice thick with arousal. "Then you'll see just how tight I can be."

Ava's breath hitched, her heart racing as she imagined what that would feel like—Deborah, stretched around the strap-on, completely at her mercy. "You're gonna love it," Ava whispered, her voice trembling with excitement as she worked her fingers faster, stretching Deborah even more.

With her other hand, Ava moved it around Deborah's body, fingers brushing over Deborah's stomach as she reached down between her legs, finding her clit with slow, deliberate movements. The touch was gentle at first, teasing, but as she circled Deborah's clit, Ava could feel the way Deborah's hips started to rock, her body responding to the combination of sensations.

Deborah let out a low, throaty moan as her hips moved in rhythm with Ava's touch. "Mmm, you've definitely been studying," Deborah muttered, her voice thick with pleasure. 

Ava grinned, her fingers working faster now, both inside Deborah and against her clit, drawing out more of those soft, breathy moans that made Ava's heart race. As Deborah's hips rocked harder, Ava knew it was time to take things to the next level. With a slow, deliberate motion, she withdrew her fingers from Deborah's ass, wiping her slick hand on the towel beside them before reaching for the bottle of lube again.

Deborah let out a soft, frustrated moan as Ava pulled away, her body trembling with the loss of contact. "Don't tease me," Deborah said, her voice full of command, though the edge of need was clear.

Ava chuckled softly, squeezing more lube onto her hands as she positioned herself behind Deborah. "Oh, I wouldn't dream of it," Ava whispered, her voice low and full of promise. "I just want to make sure you're ready ."

She spread the lube over the strap-on, coating it generously, her eyes locked on Deborah's body as she imagined what was about to happen. The silicone shaft was slightly larger than three of her fingers, just enough to stretch Deborah even more without overwhelming her. Ava's heart raced as she ran her hand over the length of the strap-on, her excitement building with every second.

Deborah shifted slightly, her body tense with anticipation as she glanced over her shoulder at Ava. "If you're going to do it, do it," Deborah muttered, her voice full of impatience. "I didn't agree to this just for you to take your sweet time."

Ava smirked, positioning herself between Deborah's legs again, the slickness of the lube making it easy to guide the tip of the strap-on to her entrance. "I know you like to be in control," Ava whispered, her breath hot against Deborah's skin as she leaned down. "But tonight... I'm the one in charge."

Deborah let out a low growl, her hips shifting slightly as she pressed back against Ava, clearly eager to get the show on the road "Just shut up and fuck me," Deborah muttered, though her voice was thick with arousal, the need in her tone unmistakable.

Ava grinned, her heart pounding as she slowly pressed the tip of the strap-on against Deborah's entrance, teasing her for just a moment before easing it inside. The tightness around the silicone was immediate, and Ava had to bite her lip to keep from groaning herself as she watched Deborah's body stretch around the strap-on.

Deborah's breath hitched, her body tensing before lightly rocking back against Ava, stretching herself. It helped the stretch, helped her adjust. "Mmm... that's more like it," Deborah muttered, her voice full of approval as it began to feel more natural.

Ava took her time, inching the strap-on deeper, her hand resting on Deborah's hip as she guided herself inside. The wetness from the lube made it easy, but the tightness around her was almost overwhelming, and Ava had to remind herself to go slow, to savor the moment. This was her birthday gift after all.

"God, Deborah... you feel so tight," Ava whispered, her voice trembling with excitement as she pushed deeper, feeling the slick heat of Deborah's body welcoming the intrusion.

"Well yes, it's not like I just let anyone do this," Deborah muttered, reminding Ava that she had in fact never let anyone take her ass. This was something she allowed Ava, a very very special gift for her birthday.

Ava grinned, her heart pounding as she finally pushed the strap-on all the way in, her hips pressing flush against Deborah's as she filled her completely. The sight of Deborah, stretched around the strap-on, moaning softly with every movement, was enough to send a thrill of satisfaction through Ava's entire body.

"How does it feel?" Ava whispered, her voice thick with anticipation as she gently rocked her hips.

Deborah's breath hitched, her body trembling as she adjusted to the feeling. "It's... good. Just very…very full."

"You're doing great," Ava whispered, her voice full of encouragement as she thrust a little harder, feeling Deborah's body respond to the pressure. But Ava could sense the tension in Deborah's muscles, the subtle way her hips shifted, as if she was trying to adjust to the stretch. The tightness around the strap-on was intense, and though Deborah was clearly enjoying it, there was a slight edge of discomfort.

Ava leaned forward, her chest pressing against Deborah's back as her free hand slid down her body, fingers finding Deborah's clit with practiced ease. She knew exactly what to do, how to ease the tension, how to turn that stretch into something that would drive Deborah wild.

Deborah let out a soft gasp as Ava's fingers brushed over her clit, her hips jerking slightly in response. Ava's fingers worked their magic, the tension in her muscles starting to melt away as the combination of sensations took over. The stretch from the strap-on, the pressure on her clit—it was almost too much, but in the best possible way. Her hips began to rock in time with Ava's thrusts, her body responding instinctively to the rhythm.

Ava's heart pounded, her fingers moving faster now, circling Deborah's clit with just the right amount of pressure, drawing soft, breathy moans from her lips. The discomfort that had been lingering in Deborah's movements was fading quickly, replaced by the growing pleasure that Ava could feel building inside her.

"You like that?" Ava whispered, her breath hot against Deborah's ear as she thrust deeper, her fingers working in perfect sync with her hips. "I told you I knew what I was doing."

Deborah groaned softly, her body arching slightly as Ava's fingers pressed harder against her clit, sending jolts of pleasure through her with every movement. Deborah's body shook with the intensity of the pleasure building inside her. She could feel the stretch, the fullness of the strap-on, but now it was mixed with the overwhelming sensation of Ava's fingers on her clit, pushing her closer and closer to the edge. Every thrust, every stroke, sent waves of heat coursing through her, making it impossible to think of anything but the way her body was reacting to Ava's touch.

Ava's heart raced, her body trembling with the effort as she thrust faster, her fingers moving with more intensity as she pressed harder against Deborah's clit. She could feel it—the way Deborah's body was tightening, the way her breath hitched with every movement, the way her hips rocked harder in response. She was so close, so close to falling apart beneath Ava's touch.

Deborah's moans grew louder, her body trembling as the pleasure built inside her, the combination of sensations finally pushing her over the edge. With one final thrust, Ava felt Deborah's body tense, her breath catching as the orgasm ripped through her, her hips bucking uncontrollably as wave after wave of pleasure crashed over her.

Ava didn't stop. Her fingers continued to circle Deborah's clit, her hips still rocking in slow, deliberate thrusts as she rode out the orgasm with her, watching with satisfaction as Deborah came undone beneath her.

Deborah let out a low, throaty moan, her body trembling as the intensity of the release overwhelmed her. She pressed her face into the pillow, her breath coming in short, ragged gasps as the waves of pleasure finally began to subside.

Ava grinned, her hand slowing as she gently withdrew from Deborah, her fingers still lightly brushing over her skin as she whispered, "How was that for a birthday present?"

Deborah groaned softly, her body still trembling as she lay back against the pillows, trying to catch her breath. "I hate to admit it," Deborah said, her voice weak but full of affection, "but you might've just outdone yourself."

Ava laughed softly, her body relaxing as she lay down beside Deborah, her hand still lightly trailing over her skin. "You think so?" Ava whispered, her voice full of playful excitement. "Think you might let me do this…more regularly?."

Deborah chuckled, shaking her head as she glanced over at Ava, her eyes gleaming with amusement. "Don't push your luck," Deborah muttered, though there was a smile tugging at her lips. "You did good, but let's not get ahead of ourselves."

Ava grinned, leaning in to press a soft kiss to Deborah's shoulder. "I'll take that as a win," she whispered, her voice full of satisfaction.

Deborah smirked, her hand brushing lightly over Ava's arm as she whispered, "Happy birthday, Ava."