"Good choice, Tom. You won't regret it," Lindsay praised him for agreeing to take her strap-on up his ass.
They stood there for a moment, recognizing the significance of what had been said: Him standing there awkwardly, still holding her dildo in his hands, his erection bulging in his pants; Her stroking his cock through the fabric, grinning wickedly at him, victorious.
She grew impatient first. "Let's move this to the bedroom. Bring my cock with you."
As they entered her bedroom, she took the strap-on back from him. He seemed eager to be rid of it, if only temporarily. Lindsay was about to put it back in her drawer, when she changed her mind and positioned it on top of the dresser, still in the harness, sticking straight up with pride.
"Get those clothes off," she instructed. While he stripped, she went back to her drawer and retrieved the next part of her plan.
"I'm such a nice girlfriend. You don't even know how lucky you are," she remarked dramatically as she passed him an unmarked black plastic box.
"I have some idea," Tom replied smiling at her as he accepted the box, standing buck naked in front of her. When he opened it, he found six burnt-orange colored butt plugs of various sizes.
"These are the softest, squishiest butt plugs money can buy," Lindsay proudly informed him. "Only the best for my boyfriend's tight virgin boypussy."
"Boypussy?" Tom asked with a raised eyebrow.
Lindsay gave no sign of retreat and confidently responded, "Yes, your boypussy. You know, the hole where I fuck you, where you submissively accept penetration from my big girlcock."
Tom looked uneasy but said nothing.
"Oh Tom. You know I love fingering your tight little asshole, but I'm positively creaming my pussy thinking about fucking you. So when all my talk about your little boy pussy makes you uncomfortable, I need you to be strong, to swallow your pride, and to bend over and take it like a good girl."
Lindsay sat on the edge of her bed, spread her legs, and rubbed the mattress in front of her crotch. "C'mon baby, stop thinking so much. Come sit between your Mistress's legs."
With an embarrassed smile and a slight flush in his cheeks, Tom sat between her legs, facing away from her, naked as the day he was born, leaning back against her fully clothed body.
With the mattress sagging slightly at the edge under Tom's weight, Lindsay could just get her chin over his shoulder to look at him in the mirror that rested on the floor, leaned up against the wall in front of them. "I bought that mirror at a garage sale yesterday. I saw it and it made me think of you. Do you know why?"
She ran her hands all over his bare skin, though she carefully avoided his cock, teasing him, trying to drive him crazy and succeeding. Tom melted into her touch, closing his eyes and letting his head fall back over her shoulder. He played along, "Why?"
"Look how nicely I can see you while I play with you. Like without the mirror, when I do this, (she slid a finger down the crack of his ass) I wouldn't be able to see you blush like a virgin. But the pose I was actually thinking of when I bought this mirror was you on your knees on the floor before me, my hand in your hair, guiding your face in my cunt, while I stare at the reflection of one of these plugs peeking out from between your butt cheeks."
Tom's eyes shot open now. "This woman is possessed by a succubus," he thought to himself, not for the first time.
"In fact, there's no time like the present to start stretching that butthole. Why don't you pick out one of your new toys to model for me tonight?"
"I thought we came in here for me to get a blowjob," Tom protested.
"And you will, provided you don't fuck it up," Lindsay answered him with an edge in her voice.
Tom managed to hold her gaze for all of two more seconds before he stood back up and opened the little box of anal toys again. He looked through them quickly, selected one, and reluctantly held it out to her.
She gave him a look of mock disappointment and took it from him. "The smallest one in the box, imagine that."
Tom stood before her, naked and sheepish, waiting to hear what else stood between him and his precious blowjob.
"Come lay across my lap like the naughty boy you are," she said with a smile after shucking off her slacks.
Tom loved her smile. He loved making her happy. And he loved how easy she made it for him, telling him exactly how to please her.
As he crawled onto the bed and over her lap, he discovered that this position made him feel like even more of a dirty pervert than he already did. She placed him where she wanted him, her hands on the scruff of his neck and on his ass, guiding his rapidly hardening erection between her bare thighs. She ran her hand idly over his full buttocks, admiring her property.
Tom looked back over his shoulder to see what she was up to, but she brought her hand back to his neck and pushed down, scolding him, "Keep your head down, slut." A hand pushed down on the small of his back. "Arch your back more, lift that ass high in the air for me." Then Lindsay returned to fondling his derriere, commenting to herself in a breathy voice "such a sexy ass...".
Tom was beside himself with arousal. His position, her words, her touches...all culminated in a rock hard erection throbbing where it was trapped between Lindsay's legs. He worried that he might cum like this and miss out of her promised dick sucking, but he couldn't bring himself to ask her to stop.
Then he felt her grip his butt cheek firmly, her thumb digging into his crack and spreading his ass wide. He knew his asshole was exposed and she was probably looking right at it. The thought sent a chill through his spine and another throb through his cock.
Her fingers began to move up and down the inner valley of his cheeks, pressing on this side and that side, but skillfully avoiding his hole. She seemed wholly unhurried, like she was completing a daily chore. Like she was a craftsman, constructing pure eroticism. He admired her patience and restraint, but it made him face the fact that he was waiting for her fingers to press up against his anus, that he wanted her to do it, badly wanted her.
He was on the verge of asking for it directly when he felt what he thought was the pad of her thumb cover his opening completely and push his entire ring deeper between his buttocks. A little whimper escaped his lips as he grappled with his surging arousal.
Lindsay was having the time of her life. She was just playing with him exactly the way she wanted, and judging by the firmness of the dick she felt pulsing between her thighs, it was exactly what he wanted too. She opened a little bottle of lube with an audible pop, spread his tush with one hand, and poured a gratuitous portion over his asshole. She watched his little hole tighten, shocked by the cool gel. She felt some of the lube drip onto her thighs. Some would probably get on the bed, but she didn't care. Her panties felt like they were soaking through anyway. She spread the lube around his hole and just inside with the tip of her finger before taking another moment to stare at his anus, glistening like the randy pussy she was training it to become.
She pushed one hand down on his lower back and he responded as she wanted, arching his back a little more, offering his slutty ass to her for penetration. She placed the tip of the middle finger of her other hand against his opening and slid inside him to the second knuckle.
Lindsay smiled as he grunted and involuntarily clenched his sphincter tight around her finger. After a few breaths, he relaxed and arched his back again, swallowing a little more of her finger with the movement. Slowly she started sliding it back and forth a millimeter at a time.
She took a moment to enjoy the scene. A sexy boy she loved, bent over her knees, moaning like a whore with her finger up his ass and his dick clutched between her thighs. Lindsay congratulated herself on every decision that had brought her to this point. In short, she had won. Either she was a master chess player or just incredibly lucky, but what she wanted was literally in her lap and she had complete confidence that this was just going to get better and better. As fantasies flashed through her head, she wondered if he had any hard limits that she wouldn't eventually be able to push through and how far she would be willing to go looking for them.
She pulled her finger free before his sphincter had a chance to realize what was happening and clench down again.
"Alright Tom, I think your horny ass is ready for the plug." Tom said nothing, but Lindsay chuckled a little as she noticed his back arch a little more for her. She lubed up the silicone toy and brought it to where it was just barely kissing his anus.
"Do you want it, Tom?" she teased.
"I want it," he responded impatiently, hoping he wouldn't be required to say more humiliating things.
"Do you want me to stretch your asshole?"
"Yes."
"Yes, what?"
Tom sighed. So much for hoping. "Yes, I want you to stretch my asshole."
