Cassie and Mr. Craig

You kiss Cassie on the lips and place both your hands on her ass. She moans at your touches and kisses, and lifts her leg to wrap around your thigh like she did before. This time, you place a hand under that thigh, signaling to her that you’d like to carry her. She obliges and wraps her legs around your waist, as you support her weight with both of your hands under her thighs near her ass. Her arms wrap around the back of your neck for additional support, but also not wanting to let go of your lips that have been bombarding her with pleasure.

You carry her inside the room, and without looking, search for the door with one of your hands. Once you get a hold of it, you flick your wrist in an attempt to close the door. Not wanting to delay any further, you walk blindly towards the bed whilst carrying Cassie, not breaking away from making out with her. Once you can feel the bed frame on your shins, you fall on the bed gently with Cassie underneath you. Cassie’s moans are becoming more frequent now, and you notice that she might be getting close just from this, and will probably orgasm if you continue.

You decide to break away from her instead, and go upright. You don’t want her to orgasm just because of ‘Magic Touch’ or the ‘Great Kisser’ traits you bought for yourself. You want some semblance of control over these traits, now that you have an idea of how they work and what they’re capable of.

You take off your shirt and Cassie looks at you hungrily. She responds by hiking up her dress so that it goes above her waist, showing you her white cotton panties, before she sits upright and takes off her dress over her head before throwing it to the floor.

She’s topless and only in her panties beneath you, and the image makes the tent in your pants uncomfortable. She notices this too and begins to unbuckle your belt while kissing your naked torso. As soon as your belt is unbuckled, you unzip your pants and take them off as well as your underwear at the same time.

You’re naked in front of her now, in front of ‘Cassandra’, as she’d liked to be referred to during this roleplay. As she shifts her body on the bed so that she’s on all fours with your dick right in front of her face, you look at her once more. As much as you’d like to pretend that this ‘Cassandra’ is someone entirely different, all you can see is Cassie; and when she looks at you, with your dick in her hand, the longing look you’ve seen her have is replaced by a look of hunger. A look of hunger that would be impossible to get in a night, no matter how wonderful the date was. She can’t hide that she looks at you with the eyes of a woman who is finally achieving something she’s dreamed about for years; not someone who only just met you.

She takes your dick into her mouth, slowly and gently wrapping it with her lips, while her tongue plays with the tip. The pleasure makes you moan, and look away from her for a moment, or the image of Cassie giving you a blowjob might push you over the edge quicker than you’d like. As you look away, and see inside your bedroom, something you would consider weird happens — you don’t feel weird about this at all.

You look down on Cassie still pleasuring your manhood, and you look at your surroundings again, thinking the sight of Cassie giving you head inside your own bedroom would bring back flashes of the past… but it doesn’t. Like an idiot, you start laughing to yourself; which causes Cassie to stop what she’s doing.

“What’s so funny, Jay?” Cassie asks, having paused her blowjob, but still stroking your dick with a steady pace.

“I’m just laughing at how stupid I was being.” you tell her, and she raises an eyebrow in curiosity.

“What do you mean?” she asks.

You grab her by her chin and direct her body to go upright like you are so you can be face to face. You give her a strong passionate kiss, hugging her back tightly, and then surprise her by pushing her onto the bed.

“I mean, I was stupid for being scared of what could happen; when there was nothing to be afraid of.” you tell Cassie, but she still doesn’t really understand what you mean.

You position yourself in between her legs and lift them up so you can take off her panties. As Cassie lays naked beneath you, you take in her natural beauty. Her erect nipples that you’re tempted to devour, her toned torso you run a hand across as you feel her sweat on your palm, and her cute shaved innie pussy that’s glistening with her juices.

“Cassie—” you moan, as the anticipation of penetrating her is building, resulting in your dick becoming fully erect. “It’s Cassandra” she tries to correct you. You go on top of her and kiss her once again. You quickly move down to her neck, planting kisses and licks as you move your fingers to her entrance to feel how wet she is already.

You go back upright, and tease the entrance of her pussy with your dick. “No, Cassie. I don’t need to pretend. I want this. I want you.” as you move your hips slowly to penetrate her. The heat of her pussy enveloping the head of your cock.

“Oh! Mr. Craig! I want this too! I’ve wanted it for so long!” she shouts, as she wraps her legs around your waist and sits up with her hands on the bed propping her up. Cassie doesn’t wait for you to set the pace, and starts gyrating her hips and grinding on your lap.

The sensations it sends your dick is intense as her movement and pace are constantly working the glans of your dick. If she goes any further, you feel it’ll take you over the edge as well. Before you reach the point of no return, Cassie stops gyrating and just plain vibrates, as her body shakes with her first intense orgasm. “FUUUUUUCK!” she shouts as her arms lose strength and could no longer prop her up. You catch her in your arms, so she doesn’t fall on the bed.

The momentary pause in her movements gives you the opportunity to explore her body with yours. She places her arms around your neck to support her, giving you the opportunity to cup her breasts in your hands and start sucking and flicking her nipple with your tongue, alternating between each nipple.

As Cassie regains her energy back, she starts moving her body up and down on your shaft. Stimulating your dick once again. You return to kissing her, and her hands grab your face as she hungrily makes out with you. Her lower body movements have been slowed down by having to multitask, so you grab her waist and start moving your own hips to fuck her at your pace.

“Oh God, Mr. Craig! This feels incredible!” she starts shouting. “I never want to let you go. I have goosebumps in every inch of my body.” she adds, before her moans become louder and louder with every pump of your dick inside her. “Don’t stop, Mr. Craig! I’m about to cum!” she shouts, but she catches her breath momentarily and tells you in a softer voice “But don’t stop until you cum inside me”, right before she groans a loud guttural groan to signify her climax.

Not wanting to disappoint her, you increase the pace of your pumps as you grip her waist even tighter for support. She rests her head on your shoulder now, her arms still around your neck, and bites your shoulder before she climaxes once more. The pain from her bite sends mixed signals in your brain as the pleasure you’re experiencing with your dick is getting close to the edge, while there’s a stinging pain from your shoulder.

In an effort to mask the pain, you pump into her even faster, shaking your entire bed as you do. Once Cassie rides the final wave of her orgasm and releases her bite from your shoulder, you feel your climax coming ever closer.

“Cassie —” you try to warn her. “Don’t stop Mr. Craig, I’m on the pill.” she replies understanding what you wanted to say. Without any more reason to hold back, you release your seed inside your daughter’s best friend with a loud groan of pleasure as you do. “I feel it inside me, my body feels so warm” she tells you in between deep breaths, her exhaustion obvious.

“I love you, Mr. Craig” she says as she stares into your eyes with a deeply satisfied and euphoric smile.

“I love —”

~ DING DONG ~

~ DING DONG ~

~ DING DONG ~

~ DING DONG ~

Stupid-fucking-piece-of-shit-doorbell