The Right Kind of Girl for Him Ch. 05

"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."

"Beg me to help you stretch your ass so that your girlfriend can butt fuck you," Lindsay pushed, confident he would say it for her but enjoying it all the same.

"Please stretch my ass so my girlfriend can butt fuck me," he said in a pleading voice accompanied by another little push of his dick against her thigh.

"Sure thing, sweetie." She pushed the plug against his little asshole, gradually increasing the pressure. Lindsay watched in rapt fascination as the muscular ring slowly lost out to her force and spread around the widening sex toy. His sphincter clenched hard trying to push the plug back out, but she held it steady. She heard his breathing quickening and she coached him, "Slow, deep breaths baby. You're doing so good. Almost there."

As instructed, his breathing slowed and his anus slowly loosened again. She increased the pressure and as he took the widest point inside him he yelped and tried to clench again, but it was too late. The squeezing of his asshole now only served to pull the plug deeper inside him, seating itself firmly in his rectum.

Lindsay caressed his ass cheeks and praised him, "Good boy."

She gave him a little spank and told him to get on his knees on the floor. He did as he was told, kneeling on the hard wood. She thought about leaving him like that, but she wanted his focus on his tongue and newly plugged asshole, not on his knees, so she dropped a pillow on the floor for him to kneel on.

"Now I'm not going to tie your hands, but I want to you put your palms on your thighs and leave them there. No hands allowed right now."

Tom put his palms on his thighs and looked up at her. His face was flushed and wore a pained expression that seemed to be a mix of humiliation and uncontrolled arousal. His dick stuck up in front of him ridiculously at a 45 degree angle. Lindsay took his face in her hands and kissed him gently on the lips with her mouth closed. Then more lewdly, sucking on his lips and thrusting her tongue deep into his mouth.

With a handful of his hair in each hand, she pulled his head back to glimpse the dazed but happy look on his face and then pushed his face between her legs, pressing his nose against the damp crotch of her panties.

"Breath deep, Tom. Smell how wet I am for you."

She watched him inhale and then groan with want. For the first time tonight, she didn't have to prompt him to use his words.

"Please..."

She waited for him to continue, "Yes, Tom?"

"Please let me lick your fucking pussy." He said it with need, with desperation, perhaps with a little bit of anger at being denied. Lindsay thought about teasing him further, but something in his tone told her that she might be close to losing control of the situation.

She stood quickly. "Take off my panties, Tom." She'd expected him to reach up and rip them off, but was pleasantly surprised when he took the hem in his teeth and tried to drag them down. He got the front of them down to the point that his nose was pressed into her bare slit, but her ample bottom wouldn't allow the back hem to slip down.

She watched him struggle for a moment, igniting her passion further, then decided she couldn't wait any longer. "You can use your hands to take them off, but not after."

Tom pulled her underwear down to her ankles but didn't wait for her to step out of them before shoving his face into her mound to feast on her.

Lindsay felt his tongue lash into her vulva with raw, hungry strokes. She immediately grabbed him by the hair and wrenched his head back. "Gentle!" she admonished him before bringing his face back to her sopping quim. He licked more carefully now, slicking her lips fully with his saliva and her own juices. She looked to her mirror on the floor behind him, but the angle was wrong with her standing, so she pulled his head away from her again, stepped out of her wet rolled up panties and sat back on the edge of the bed, guiding his hungry mouth back to her cunt as she did.

She ran her fingers through his hair lovingly as he ate that pussy with abandon, his eyes closed, his lips vibrating when he intermittently moaned directly into her crotch. She glanced up into the mirror and saw that she'd recreated her fantasy perfectly. The butt plug stuck out prominently between his cheeks like a flag claiming his ass as hers.

Lindsay decided to experiment with the control she now had. She pulled his head right then left to focus on each of her labia. She pulled his head up so his tongue was whipping about directly over her clit. "Open your eyes, Tom." His eyelids parted and he stopped licking and tried to move back to better look at her, but she held his head tightly against her mons. "I didn't say stop." His tongue got back to work as they held eye contact.

"Do you realize Tom how much I own you? Let me describe it to you. You're butt naked on your knees on my bedroom floor with your tongue in my cunt. Your asshole can't close because my plug is deep in your ass."

Tom's eyes closed and a deep, guttural moan left his throat.

"EYES OPEN!" Lindsay shrieked, pulling on his hair for emphasis. They stared at each other again as he continued to pleasure her with his mouth, his submission leaking out of his eyes into hers.

"I love how you surrender to me Tom, and I know you love it too." Lindsay's orgasm was close, her voice now quivering with need. Without breaking eye contact, she pushed his head lower and his tongue started pumping her love tunnel. She had no plan now, working purely on instinct. As she looked into his submissive eyes and felt her orgasm approaching, she pushed down ever so slightly on his head again. Her eyes held a question, not sure what he would do. His eyes read hers for a moment, then his tongue dipped down and licked her asshole.

"FUUUUCCCKKK!!" Lindsay screamed as she came. She crushed his head between her legs, holding onto his skull for dear life, as wave after wave of ecstasy crashed over her. "Uhhh, uhhhh, uhhhh," she moaned with each contraction as she came down from the pinnacle.

Finally her muscles relaxed and she was able to sit back, press a foot into Tom's chest and push him back. He fell back onto his hands and looked up at her, panting to catch his breath. For a moment they stared at each other like wild animals before her face broke into a wild grin and she started cackling like an insane woman.

"Hahaha! Fuck yes! What a man you are, Tom, you bad bad man!"

Tom smiled back proudly from the floor.

"Come lie down up here. I want to suck that dick."

Tom scampered into her bed with Olympic speed.

She straddled his chest and finally took off her top and her bra. She enjoyed how dirty it felt to grind her bare pussy on his chest and spread her juices on him. Then she moved down his body and shoved her tits in his face. He took her nipple in his mouth and sucked like a babe. At the same time, she pushed his wrists above his head and told him to keep them there. She kissed her way down his neck and chest, taking a nipple between her teeth briefly before continuing down his belly.

When she got to his cock, she let her hot breath blow against it for a few breaths to tease him. "Are you sure you want a blowjob, Tommy?"

He surprised her by thrusting his hips up off the bed, the tip of his dick glancing off her cheek.

She gasped with exaggerated indignation before taking his balls in her hand, gripping firmly and pulling him back down to the mattress. "You're lucky you just gave me the best orgasm of my life," she chided.

Lindsay pressed her tongue flat against the base of his cock, pinning it against his belly, and slowly dragged it up, pulling off just before she got to his crown. She planted a wet kiss on the head. Then she went down and started licking his balls. When she sucked a testicle gently into her mouth, Tom luxuriated in the unique sensation. Then he felt her tugging on the plug in his ass. He felt his anus reflexively squeeze down on the squishy butt plug, which he admitted to himself felt delicious.

Lindsay let his testicle pop out of her mouth. "Oh Tom, it looks like your ass doesn't want to let go of this plug," she teased him while she alternately pushed and pulled on the rubbery toy. Then she pulled gently but firmly until his now loosened ring lost its grip and the plug popped out of him.

She set the plug aside and then, for the first time that night, took his penis in her hand. She felt its warmth, how it was hard at its core but covered in delightful softnesss, how it flexed in her hand like a mythical creature. She angled his dick away from his body now and slowly traced the tip over her own lips. She let her tongue flutter out and lick at the precum oozing from his slit.

"Now Tom, in a minute, I'm going to make you cum in my mouth. I'm going to drain you dry, baby. But first, you need to tell me something. I'm going to let you decide this. Do you want an empty asshole when you cum or do you want to feel your pretty asshole contracting around my finger as I push on your prostate and suck out your seed?" Lindsay knew any good lawyer would object that she was leading the witness, but she'd decided she would let him enjoy the end of his blowjob however he wanted.

Always dependable, Tom answered, "Your finger. I want your finger."

Lindsay smiled knowing that she would soon have him literally wrapped around her little finger. "That's my baby. Now grab your thighs and pull your knees up to your chest. Spread yourself for me."

When he did, she pulled his dick back so that it was taut, sticking up between his legs more than 90 degrees from his belly. She took the first several inches into her hot wet mouth. She stroked the base in time with her bobbing head as her other hand fondled his balls and teased his perineum. She stopped bobbing her head and let her tongue explore the meat in her mouth as she hooked a finger on the lip of his asshole.

She slid her finger deep in his ass, surprised at how loose he was now. "Butt plugs work," she thought as her finger grazed his swollen prostate gland, which protruded from the wall of his rectum.

She pulled his dick from her mouth with a pop from the suction of her lips. "I'm going to make you cum now baby. Cum for me." She took his dick back into her mouth, not going for depth, but rather positioning her tongue to stimulate the underside right under the head. She worked the finger in his ass in the classic 'come hither' motion, stroking his prostate. She sucked gently on his fat cock as she wagged her tongue under his tender head.

Finally, she felt his cock strain between her lips, so she sucked hard and smashed her anal finger against his prostate, flattening the engorged gland back into the walls of his rectum and triggering a massive orgasm. His pelvic muscles spasmed in unison. His dick jumped in her mouth and blasted a jet of hot cum against the roof of her mouth. His asshole clenched down hard on her finger like it was trying to break it off. When he started to relax, she released his prostate and focused on sliding in and out of his rhythmically contracting sphincter. She stroked his dick into her mouth, draining him of all his backed up cream.