Chapter 12

He nods his head yes to her question. “It was pretty fun actually.”

“Even though I wasn’t there?” Jessica asks, raising an eyebrow up at him.

Casey’s face turns a shade of red as he suddenly feels a little guilty and dishonest for a moment. “I wish you were.”

“You don’t have to fret, Casey,” she says, placing a hand on his arm and squeezing it gently. “I set it up so that I wouldn’t. I wanted you to be you and not having to worry that with me there you might do something wrong.”

“So you knew Bart was bisexual?”

Jessica shakes her head. “Well, I mean, it should be obvious with what this place is and all.”

“What exactly is this place?” Casey asks.

“A place where people discover their sexual needs,” she answers. “It is a place where one goes to learn to lose grip of societies rules on sexuality. Where you go to discover who you are, not what you told that you are.”

“How did you find it?”

“Well, for one I’m a therapist,” she says smartly. “But is has been around for a very long time.”

“How long?” Casey pushes. “And why haven’t I heard of it?”

Jessica shakes her head. “It doesn’t matter. All that matters is that it is helping us—helping you.”

“Us?”

Jessica puts her finger to his lips and whispers, “Shhh...” Then she pulls up her dress to reveal a harness around her waist. “I’ve got a little surprise for you. I know you were hoping for more this afternoon, so I am going to make up for that.”

“Is that a...” he begins.

Jessica is already turning around, back to him with a large dildo in her hand. “No more questions right now,” she says. “Let us continue with improving the situation so that we can finally move forward in our lives.”

Casey stares at the toy in her hands. It is a good sized one with a nice girth. It is the kind of dildo that can be presses up against something, or because of the flat base, is also designed to easily click into place with the average harness ring of a strap-on. Jessica slowly brings the silicone toy down and slides the ring aside as she pushed it through and locks it into place. It then juts out from her body and curves upward like a banana.

Jessica strokes the dildo with her hand as she stares right back at her boyfriend. He is breathing heavily as he stares back at her. “I had it custom made. I figure the curve would make it a little more interesting, especially for your first time.” She smiles and asks, “How do I look?”

“You look ... fuck ... you look fucking hot,” he answers. Casey is suddenly so aroused that his cock is as hard as steel in his pants.

Jessica can see the outline as nothing is hidden at all. “Get naked,” she says, pulling off her own dress. “And get on your belly.”

Casey does as he is told and lies on the bed. Jessica is right behind him, swinging her legs over his and sitting right at the top of his thighs where they connect to his ass. Casey is completely hypnotized by what she is doping to him. As the toy rests between his ass cheeks Casey moans a little. Jessica smiles to herself and bites her lip with an intense craving. She spreads her legs further and Casey moans as he feels the silicone tip firmly presses up against his crack, enjoying the way it feels. Her hips gyrate a little into him, the toy driving against him with a definite suggestiveness that this is really going to happen.

Jessica does it again, but not so subtly. Then she starts to do it more. She sits up all the way and then pushes forward with a little more intent into her backside. As it becomes clearer and clearer, closer and closer to happening, Casey becomes incredibly nervous and aroused all at once. All he can do is wait to see what she does next. Every second grows more exciting as she rubs the toy along the crack of his ass. The next time she lies down on him, she brings her lips close to the side of his face and speaks into his ear after he moans deliriously at the hard push, asking if he is ready.

“Yesss...” he hisses.

Jessica kisses his ear sweetly as she pulls herself back up from his body. She grabs a bottle of lubricant and squirts it along the crack of his ass and then begins massaging it in. Casey begins to moan even more and she loves every sound he makes. She spreads the lubricant all over his crack, working his cheeks so that she gets a clear view of his backdoor. She runs her fingers over him as Jessica herself is on overdrives. Casey is completely under her direction.

Her fingers begin to dip down into his crack and she runs them all the way down his ass to his inner thighs. Casey’s erection presses into the bed as she continues to pass ever so closely to his balls. On the next pass, she allows her fingers to travel back up through his crack, around his asshole and then across the soft flesh. Casey’s breath catches. His asshole pulses, showing her that he really wants it. She smiles to herself knowing that this will set him up for what is to come starting tomorrow.

Finally, she runs her fingers all the way up the inside of his thighs where they stop at the base of his sack. Casey groans into the covers. Her fingers run up his crack to stop at his sphincter. She frags a fingertip around the puckered entry and Casey groans even louder. Just as quickly though, she pulls her hand away and grabs the bottle of lubricant, squeezing a bit into her hand so that she can lube up the silicone toy strapped to her luscious body. She tosses the bottle aside, angles the toy and spreads his cheeks apart with her greasy hands. Casey feels it pressing against his opening and his prick is throbbing with anticipation.

Jessica rocks back and forth. He feels the tip push past his ring of muscle. And then the toy is in him. He clenches his teeth while marveling at the powerful pleasure of his girlfriend using his ass how she wants to. Casey moans in the naughtiest way. His ass presses back against the dildo and Jessica just continues to slowly press forward into him.

When it is half inside his backdoor, Jessica leans in and whispers into his ear, “Do you want my big dick?” Her voice is the sexiest he has ever heard it. Most of all he loves how she called it her cock.

Casey moans into the bed. He wants it, all of it. Her movements, her words, open up his mind just as her hips slowly work his ass open. Precum leaks profusely from the tip of his prick. It’s not slowly down any more than Jessica is with her pushing. Then suddenly, she pulls the toy back out. Casey gasps as his ass pulses.