content warning: anal penetration
December 9th
"Is that an anal plug?" he asks, curiously eyeing the toy in her hand. It's black and cone-shaped and has a loop at the thicker end.
„I think so. It's very smooth. Here." She replies, handing the small item to him. Harvey lets his hand glide over it.
He agrees. "It is." He looks at her closely, sensing her discomfort. Harvey cups her cheek with his hand, gently stroking it with his thumb. "Donna. It's okay if you don't want to use it. I know that you are not always in the mood for anal."
Truth be told, they only tried anal twice in the few months of their relationship, but they did it with his fingers only. The first time they had spoken about sexual practices prior and found out that they both tried anal sex with other partners before. Donna admitted that it was sometimes a little uncomfortable for her, but she liked it in general. They both wanted to try it with each other again. Harvey was extremely tender and caring and it's been a great experience for both of them.
The second time she explicitly asked him for it. He was fucking her from behind that day, massaging her ass cheeks in the rhythm of his thrusts into her core. She gasped loudly and asked him to put a finger in her ass. He almost came on the spot but he was able to hold it back, Donna on the other hand came pretty fast after his finger sunk into her slowly and he continued pounding into her core at a steady pace.
After that, he sometimes played with her buttock while he moved inside her or when he went down on her, knowing that it would be beneficial to her arousal. But he never went further since then. Simply because he didn't feel the urgent need and she didn't ask for it.
"But," Donna says now. „I think I am in the mood for it today. At least I was thinking about it more than once over the last few days." she says smugly, trailing her fingers over his naked body and raising a seductive eyebrow at her boyfriend.
„Are you sure?" he wonders, still stroking her cheek. He didn't want to give Donna the impression that he really wanted to try it although she didn't want to. But Donna reassures him that she wanted to try it too.
„I am. I'm just not sure about this thing but maybe we could give it a try." she states, pointing to the toy in his hand.
„Ok, we'll try and you just tell me if you want me to stop. And we could make use of the lube from door two." Harvey suggests and Donna nods. She smiles at him and places a soft kiss onto his lips.
When they part for air he softly asks „Do you want to lie down on your belly?" and she nods, shifting so that she is lying flat on the mattress. Harvey gets the lube from the nightstand.
He pats her butt. „Maybe I can put a pillow under your pelvis?" "Sure," she says and places a pillow there to lift up her center and grant him better access.
The arousal is already building up in Harvey, Donna's perfectly shaped backside towering in front of him increasing the anticipation for what is to come. He knows very well that Donna needs some gentle caresses to fully relax before trying any anal action. So he also gets some massage oil from the nightstand and asks her if she is comfortable. As she confirms that, he starts massaging her back body and her butt cheeks until he can sense some tension leaving her muscles and she hums sweetly. He massages her ass cheeks further as his dick starts to grow.
His hands travel down her thighs and gently spread them. He starts sliding two fingers through her slit, making her wet and spreading her moisture. He circles her clit several times, her body relaxing more and more under his ministrations as her moans are getting louder. He slides a finger into her slippery center, just to try how ready she is for him and thrusts in and out a few times.
He then lets his fingers glide over her perineum to her buttock and he massages the surrounding flesh. His dick is at full attention now and a part of him just wants to fuck her, but the bigger part of him is so giddy for pleasuring her with the small toy.
So he continues, spreading some lube over her buttock, slowly trying to slide his index finger inside. Donna gasps and he sinks inside, but her walls clench on reflex and bring his thick finger back out. „Relax", he whispers and gently massages her ass, placing soft kisses on the small of her back. Gathering some more lube he tries to enter her hole once again. This time he can bury it into her deeper and they are both moaning on the sensation.
"It feels so good Harvey," she whimpers, after he let his finger sink into her as deeply as possible. "Wanna try the plug now?" he asks tentatively and she just makes an incoherent sound but he takes it as a yes. He slowly removes his finger from her and she grunts on the loss. He takes the plug and covers it with a generous amount of lube, also adding some more onto her back entrance. Once again he firmly strokes her folds and clit to keep her relaxed and increase her arousal.
Donna didn't know how close she had already been until Harvey touches her clit again. She is sure that she will come within the next few seconds if he doesn't stop teasing her there, but she wants him to continue with the original plan.
So she pants „Harvey", begging him to keep going and he gets the hint and returns his attention back to her butt. He inserts the plug ever so slowly, never stopping to knead her cheek with his other hand. He pushes a bit stronger, slowly stretching her, but at some point her constrictor reacts once more and brings the toy back out.
„Keep going," Donna spurs him on, not wanting him to stop even if it's a tiny bit uncomfortable. But her pleasure is bigger and her body is adjusting fast to the stretch. So Harvey tries it again, but at the same time he starts placing open mouthed kisses onto her butt cheeks and gently bites the soft flesh. And this time it works, accompanied by her sweet moans the toy slowly disappears in her butt completely, even the thickest part, and only the strap is left sticking out.
"Oh god," she gasps and Harvey asks with a strangled breath from his own arousal „You like that? Does it feel good?" "It feels amazing." she groans.
He moans and his kisses travel down to her folds again, as he still watches the end of the plug poking out from her stretched buttock. And he is pretty sure that this is one of the hottest things he has ever seen in his whole life.
"Harvey," Donna states and he hums a question. "I would really like to feel your dick in me right now." He needs to reassure himself by asking "Are you sure?", but is already shifting his body on the mattress.
Donna gets onto all fourth and he gets on his knees, grabs her hips and slides in, slowly and carefully. They both groan loudly on the sensation. „Oh fuck!" Harvey whimpers. Donnas walls have never felt tighter around his cock and Donna has never felt better filled before.
The picture of Donna in front of him, clutching to the headboard of their bed, with his dick buried deep in her pussy as the end of the black anal plug sticks out from her butt cheeks, combined with the new level of tightness around his member is so freaking hot that it almost takes Harvey's senses away. He is sure that he won't last long.
But as he starts thrusting slowly she beats him to it, surprising both of them by suddenly exploding around him, screaming „Oh god Harvey, oh, fuck, yes."
Her walls are fluttering around his length, her legs are shaking heavily, her hips buck erratically. Harvey isn't even sure if it's only one orgasm, but he just helps her through it by gently stroking her back and ass, until she collapses onto the mattress, losing contact with his dick. Harvey didn't come, but it doesn't matter right now. Currently he is fully enjoying Donna's immense pleasure and he is sure that he will get his money's worth later.
"Fuck..." she mutters next to him, breathing heavily, barely able to catch her breath. She is lying on her stomach and Harvey lays down on his side next to her, still stroking her back. "Gosh, Harvey… I came so hard… That was so good." she whimpers as she tries to steady her breathing.
„I know Donna, I know. I'm here. Just breathe." he answers and kisses her shoulder.
It takes her a while to recover, but after that it is not long until she makes him come just as good as she did.
