olicity + first time anal (Anonymous)

"Oliver, look at me," her voice snaps him out of the trance he's been in since she stepped into the bedroom wearing that thing around her thighs. It looks completely out of place against the soft curves of her body, the straps hugging her legs tightly as the long piece of silicone juts out from between her thighs. His eyes have been transfixed on it ever since she left the bathroom, and when he spots the worried look on her face, her teeth gnawing on her lower lip in hesitation, he realizes too much time has passed since he spoke.

"Yes," Oliver chokes out, his voice a little more strained than he expected. After all, he was the one to suggest this, the one who wanted to try it after accidentally stumbling upon the images in the Tumblr app on her phone. He'd gotten hard, watching the gifs of men being dominated by their women wearing the exact device she currently has strapped to her hips now.

He swallows, watching her step up to their bed. The thigh high stocking with matching garter belt and the black bra covering breasts only add to his anticipation as he lays there, his eyes never leaving hers, until she's finally at the foot of the bed. His breath catches as he takes her in. "Jesus, Felicity," he whispers, his fantasy suddenly becoming real.

"Do you still want to do this?" she asks, staring down at him to gauge his state of mind, to make sure he's all in, that this isn't something he's going to regret later on.

"I do," Oliver replies without hesitation.

"Alright, then," Felicity affirms. "Just remember, if you want me to stop, you can always use the safe word. Do you remember what that is?"

"Red," he answers.

"Good." She reaches over, grabbing the bottle of lube that rests near his ankles, and pours a generous amount in her hands. Once they're completely coated and glistening in the soft glow of the incandescent lights spilling from the bedside lamps, Felicity's head rises, her chin jutting out, and she takes on the air of the mistress she promised to be tonight. "On your stomach," she orders.

Oliver does as he's told, rolling so he's face down on the bed, and waits for his next command. "Come closer," Felicity says, and he inches his way towards her on his hands and knees. As he nears the edge of the bed, her slick fingers on his ass make him pause. "Stop," she commands, and he stills, back straight, arms and legs taught, eyes staring at the headboard of their bed.

Her fingers slip between his cheeks, slathering the lube all over where she plans to use him, paying special attention to his anus as her fingers probe the tightly puckered hole, stroking round and round until Felicity says, "Relax, baby. Just remember, you can tell me to stop anytime."

Oliver nods his head, but ends up getting a hard slap on the ass in response. "Ah-ah! Use your words. I need to hear you say it," she admonishes, reminding him of the deal they'd made before the evening started.

"Yes, Mistress," he replies, still feeling the sting radiating out from where she'd hit him. He forgets how much training she's had in the past few months, and although he's not too happy that she's using it on him, he's proud that she now has power behind her hits. It brings him strange pleasure to feel the pain of her hand against his ass, and he readies himself for what's to come.

Felicity's fingers haven't stopped playing with his ass, and now that he's relaxes, he feels her begin to press against him. Slowly, gently, her forefinger penetrates him for the first time. The sensation feels strange, but pleasurable, and Oliver moans, letting her know she can keep going, and she does, until she's in him up to the second knuckle. He lets out a shuddering breath, pleasure overtaking him as she strokes his inner walls with her finger.

"Do you like that?" Felicity asks. "Does it feel good?"

"God, yes!" Oliver groans, his head falling against the soft duvet as he grabs fistfuls of the fabric to hold onto while she continues stroking him, her finger pulling out before pushing back in, over and over again, until his body is practically vibrating from the pleasure that radiates through him. He has no idea what she's doing, but whenever her finger presses down, she hits a magical spot that makes his back bow and his eyes squeeze tight.

Precum dribbles from his rock hard cock the more Felicity prolongs her torture, stroking that spot over and over, until he can't take it anymore. He's about to cry out the safeword and beg her to give him the release he so desperately craves when her finger pulls out of him completely, leaving Oliver feeling empty and dissatisfied. Fuck, he needs her inside him again! His cock continues to ooze, and he starts to reach down in an effort to get some relief, but she smacks him again, harder this time, and he immediately pulls back.

"No touching!" Felicity orders. "Your cock is mine tonight. Understood?"

"Yes, Mistress," he complies, keeping his head down. Then, he feels a new sensation against his ass, harder, smoother, larger than her finger. It presses against his anus and Oliver immediately relaxes, the lube coating its head allowing it to glide into him with ease. The deeper it pushes into him, the wider it gets, stretching his ass until he feels the smooth skin of Felicity's thighs against the back of his own.

That's when Oliver realizes, she's finally used the dildo that's strapped to her hips. He shudders as Felicity pulls back, leaving only the tip inside him, then she does something and it begins to vibrate softly inside him. The new sensations send jolts of fire through his veins, making him moan and shudder in absolute pleasure. He's never felt anything like this, never thought he'd find it so arousing or erotic. Felicity dominating him with a strap-on is his new favorite thing, and when she begins to push into him again, the pleasure increases tenfold.

"Oh, fuuuuuck!" Oliver moans, his eyes squeezing shut. She thrusts deeper, until she's balls deep, and all of a sudden, his whole body goes into an almost trance-like state. An absolutely incredible feeling of orgasm without ejaculation washes over him and it's amazing. He lays there, shuddering, and Felicity remains seated in him, the vibrator doing all the work. For a second, he thinks, 'Okay, that was fun,' but less than a minute later, it's happening again, then again, then again. The feeling is incredible. It's as if he's lost total control of his body, feeling the pleasure from the top of his head to the tips of his toes.

Oliver has no idea how many times she makes him come like that, but he's practically spent when she finally turns the vibrator off. It remains buried in his ass, though, as Felicity leans over him and presses soft kisses to his back. For a moment, he thinks the torture is over, and he can slump into bed, but she's not done with him yet. Her hand wraps around his cock and squeezes, and he can't stop the shuddering groan that escapes his throat.

He's still rock hard, precum pooling on the sheets beneath his dick, on the verge of blacking out as his girlfriend's hand begins to milk him. She's rough and fast, jerking hard, and suddenly the vibrator clicks on again. Oliver's vision goes white, his teeth sinking into the duvet as his hands grab hold of it, hanging on for dear life. Just when he thinks he can't take it anymore, she leans over him and whispers into his ear, "Come for me, baby."

The vibrator hits that spot as her hands squeeze his cock and balls, and Oliver shoots the biggest load he's ever seen come from his dick. It oozes from between Felicity's fingers, dripping onto the bed, and he's done. She shuts off the vibrator and slowly pulls out of him as he slumps into the mattress, his body spent and languid. He drifts in and out of consciousness, not noticing that she has left to room until she returns with a warm washcloth to clean up the mess they've made. It's wiped all down his ass, cock, and thighs, ridding him of the lube and semen that coats his sink.

When she's done, Felicity wanders off again, this time returning in her all her naked glory. She's ditched the stocking, bra, and strap on, and slides into bed beside him. "You did so well," she cooes, her hand gently stroking his cheek as Oliver gazes at her in wonder. "How was it?"

"Absolutely amazing," he mumbles with a dopey smile. "Ten out of ten, would do again." She leans in to kiss him softly before settling against his shoulder.

"Good," Felicity replies.

"Was it good for you?" Oliver tentatively asks, hoping she had as much fun as he did.

Her bright smile confirms what she says, "Incredible. I'd love to do it again if you're willing."

"I'm always willing to do anything, as long as it's with you." His sappy response gets a little giggle from her as she presses her lips to his once more before pulling away. He bands an arm around her waist, pulling her close, and they fall asleep like that, sated and content.