The Right Kind of Girl for Him Ch. 04

Tom had never been good at dirty talk. But he liked that Lindsay obviously was. He smiled even as his cheeks flushed with embarrassment. Her long slender finger was on an out thrust as he fully embraced slut mode and clenched his sphincter around her, trying to keep her from leaving, simultaneously humping his whole pelvis towards her hand. He tried to think of something naughty to say in response, but his thinking functions seemed to be disabled at the moment. "Please make me cum," he said weakly as a half-moan.

Lindsay smiled and went for it. Careful not to jump the gun and go for it directly. She steadily increased the speed of her finger fucking in and out of his slutty butt hole, lengthening her strokes of his manhood, pushing harder against his prostate with each thrust. She felt his climax approaching, every muscle in his body tightening, his back arching. Then she smashed her finger against his gland trying to flatten it back into the wall of his rectum.

Tom saw stars. His asshole slammed closed tightly around her digit. His mind went white with blinding pleasure. He felt the first shot of cum splash under his jaw as his cock twitched in Lindsay's hand. She kept up the rhythm, stroking his member, sliding her finger in and out of his clenching ass, emptying his balls, and utterly conquering him.

When it finally ended, Tom relaxed the extreme arch of his back that had driven his chest up and his head back and looked down between his legs to see if Lindsay had survived the cataclysm.

"Good boy," she praised with a smile.

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Things were good. Tom had never imagined that his fantasy girl would actually exist in real life. Or that if she did, he'd ever have a chance with her. Lindsay was the hottest woman he'd ever had, hell ever seen, in porn or elsewhere. It wasn't how she looked, though she was objectively attractive, but it was her presence in the bedroom. Her confidence, her lack of hesitation. She knew exactly what she was doing and when to do it. She was like a supernatural creature, a once-in-a-generation talent for driving him wild in bed.

Still...even in paradise there were things that could be better. Since that first night of life-changing sex at his place, he'd seen her five times. The day after. The day after that. Then, he'd worried about appearing needy, clingy, pathetic - all those adjectives employed by people not in love. He'd forced himself to go 48 hours without contacting her. When they'd met up the next day, she'd asked him about it.

"So Tom, why didn't you text the last couple of days?" she'd inquired while fixing him with a piercing stare.

"Oh...just that I've been a bit busy...and I mean we have been seeing quite a bit of each other," he'd replied lamely.

Lindsay looked skeptical. "It's fine if you were busy or if you need some space, but is that the truth?"

"Well I didn't want to seem clingy," Tom admitted, flustered from being called out.

"So you wanted to see me, but you didn't text because you didn't want me to know that you wanted to see me?"

Tom turned red, surprised by how ashamed and guilty he felt now.

"That seems foolish, doesn't it Tom?" she questioned.

Not wanting to admit total defeat, Tom gave her an apologetic look and shrugged.

"From now on, if you want to text me, text me. If you need space, tell me you need space. And I'll do the same. Ok?"

"Ok," he'd sheepishly agreed.

A few minutes later, something occurred to him.

"Hey, why didn't YOU text ME?!" he accused.

For an instant Lindsay looked caught. Then, she broke into a smile and said, "Cause I'm not a clingy, little bitch." She'd laughed and followed up with, "No more talking! Time for you to get naked."

The sex that night had been glorious.

Still, in five nights together, he'd yet to fuck her. He hadn't even gotten a blow job. Tom wrestled with whether to bring this up, not wanting to mess up a good thing - the best thing he'd ever had. Each time they'd had sex had been better than anything he'd had before her, but it nagged at him. Would she EVER suck his dick? Would she ever take his cock inside that tasty wet pussy? What if she had some weird aversion to the idea, like it wasn't 'dominant' enough for her? Could he live with that? The volume of this internal monologue had now become deafening. He needed to know. So the next night, shortly after they'd gotten back to her place, he asked.

"Listen Lindsay, I like you a lot. I'm pretty sure I'm falling in love with you. You're so good in bed that you've probably ruined me for other women anyway. But...you've been direct with me and you've encouraged me to be direct back...so I need to know, when am I gonna get to fuck you?"

For a moment, she looked surprised by his little speech. Then she recovered and gave him that same wolfish smile that made him love and fear her at the same time.

"You mean, when are you going to get to put your pecker in my perfect little kitty?" she teased in an exaggeratedly high-pitched voice.

"Yeah, when?"

"Soon I hope. I'd be lying if I said I hadn't imagined how your big, throbbing johnson is going to feel inside me." She grabbed his crotch with one hand and gave him a little squeeze. She put her lips close to his ear and continued in her most whorish voice "Your massive phallus, your huge manhood, your..."

"Alright, alright," he pushed her back where he could look her in the eye and removed her hand from his crotch. He enjoyed her naughty talk, but this was serious and he wanted an answer.

"When?" he asked calmly but firmly.

"Just as soon as you take my cock inside you."

His eyebrows went up questioningly.

"My strap-on cock I mean."

Tom said nothing. He hadn't prepared for this. He'd actually fantasized about her fucking him with a strap-on. But he'd imagined this would happen 'someday.' Like someday far from now. Not right now. Not before he got to fuck her.

In a low quiet voice, he asked, "How big is it?"

Lindsay smiled at him and went to her bedroom. She returned holding a purple rubber dildo attached to a black cloth harness. She handed it to him, looking nervous and hopeful.

"It's big," he noted.

"Not as big as you."

"Your vagina is bigger than my asshole."

She touched his arm and gave him a conciliatory look. "That's why it's not that big for your first time. And look, I'm not going to leave you to figure out how to take it all on your own. I'm going to train you to relax. I'll teach your asshole how to submit and loosen up. I promise I won't fuck you until I think you're ready."

It felt weird holding her dildo in his hands. He thought about it fucking him. He gulped, finding it suddenly difficult to swallow his saliva.

"Have you ever fucked someone with one of these before?" he asked, basically just stalling at this point.

"No. You'll be my first."

He took in the innocent, vulnerable look on her face. It wasn't a look he had seen often.

"I really want this, Tom. I think you'll really like it too."

After a few moments of silent contemplation, he knew he was going to say yes. But maybe he could get something else out of this.

"Ok, but since we're going for the spirit of equality, taking turns being the fucker and the fuckee, then it seems like you owe me a blow job. I've gone down on you loads of times but I've never felt your hot mouth wrapped around my dick."

He tried to keep a poker face as he waited for her reply. She in turn stared him down in silence with an unreadable expression on her face. A minute passed.

Then she said, "Hmmm, that's not quite right. I...I don't want equality exactly. I mean I want us to have equal respect for each other, but I don't want our roles in the bedroom to be the same, I don't think you do either. So I don't want you to misunderstand how it will be the first time I take your dick inside my cunt. It's not like I'm going to let you bend me over and pound my brains out."

"So how will it be then?"

"I'll be the fucker in both cases. When you give me your ass, I'm going to take you. I'm going to spread your legs and penetrate your tight little virgin hole with my dick. Of course I'll take your feelings into consideration, the sounds you make, your cute little facial expressions," she smiled up at him, "but I want you to give up control, to surrender that to me. I'll be controlling the pace, the angle, the depth. There will be no doubt in our minds that it was you who got fucked that night."

His facial expression was hardening a bit now, his guard starting to come up as his limit for vulnerability was approached. She ran a hand across his cheek and into his hair, caressing him lovingly. Then she continued, "Then, when it's time for me to take the penetration, perhaps on the following date, I'll accept every inch of this big, fat dick," she lightly stroked his erection through his pants, pleased he had become increasingly hard as she spoke, "into my tight, wet pussy." She paused for a moment to let him picture it. "It's going to feel so good for you, buried deep inside me, clutched between my velvety walls, the strong muscles in my cunt squeezing you and pleasuring you." She grinned as his cock throbbed and he let out a little moan. "But..." she said giving his cock a little squeeze, "you'll be on your back, your wrists and ankles will be tied to the four corners of this bed, you'll probably have something in your ass. I'll be controlling the pace, the angle, the depth. I'll be fucking your cock with my cunt."

Her pussy clenched at the little pout on his face now. An interesting mixture of disappointment and lust. She cradled his face in her hands and gave his frowning lips a little peck. She giggled and brought her lips right to his ear, "Oh poor baby. You know you'll love it. Your dick is rock hard right now. I'm going to give you pleasure that you never even dreamed of," she took his earlobe into her mouth between her teeth and then gave a teasing lick to his ear canal.

She moved back to look into his eyes again. She'd given him full disclosure to make an informed decision. Now, she slid her hand down to his dick and resumed stroking. No harm in helping him make the right decision.

"Hurry up and decide so we can get to that blow job you mentioned," she prodded.

Tom already knew what his answer was. She probably could have asked him to cut off a finger and he would have eventually agreed. But he didn't want to look like a slut, not to her, at least not in an easy, desperate way.

So after what he deemed an appropriate amount of time to weigh the decision, he gave her a reluctant smile. "I'll do it."