The Right Kind of Girl for Him Ch. 03

Tom checked himself over in the mirror one more time. The man looking back at him looked half-deranged, smiling at 1000 watts. He couldn't help it. He still couldn't believe his good luck.

Sure it had been a little embarrassing, fleeing the park with Lindsay's jacket tied around his waist in an obviously strange configuration covering more of his crotch than his butt. But he had smiled and laughed to himself at his situation as he ran to his car.

He'd made it half way home before his internal monologue started peppering him with questions. Was this a relationship or just sex? Did she really like that he came in his pants or did she think that was pathetic? How did she know Megan? What would happen tonight?

Tom remembered that he was supposed to text her his address so she would know where to pick him up. He typed it in and stared at the unsent text. Should he say something more? Something witty and endearing? Maybe an emoji. Heart emoji? No, too effeminate. Peach emoji? Best not to push it until he understood her tastes a bit better. He settled on, "Can't wait to see you again," with a smiley face after the address. Solid.

He had several hours until their date and his frenzied thoughts showed no signs of slowing down. Was she out of his league? Should he dress formal or casual? Should he shave his balls? Was her bush shaved? Would she ask him to do things he was uncomfortable with? Should he propose they have a safe word?

He decided to go for a run to clear his mind. He changed out of his cum-stained pants and underwear and put on some loose running shorts. Tom wasn't really much of a jogger, usually found it too boring, but he sometimes used such rote exercise to burn off nervous energy. He was nervous but still felt good. Maybe 70% excited, 30% scared.

As he let his legs carry him in a random path through his neighborhood, he tried to get some perspective. Yes, she seemed to be perfect for him. Yes, she was a sexually dominant goddess who'd made him cum in a public park. Yes, she'd said that she wanted to finger his asshole. But, they'd only just met. He told himself not to get his hopes up. Better than likely they had some immutable incompatibility that would reveal itself soon. Hell, maybe she wasn't even interested in him apart from sex? He hoped she wanted more, but told himself that just sex would be fine too.

The way she had taken his hand and guided him through the park. The way she had crawled on top of him and kissed him. He had never been pursued like that before. It had been great. He'd had no anxiety about what move to make; he'd simply followed her lead and loved it.

Tom wondered if he was a slut. Had he given in too easily? Should he have put up some sort of token resistance? He'd never considered it. He tried to picture a scenario where she wanted something sexual from him and he chastely refused, "No, honey, not yet, maybe when we're married." He burst out laughing as he ran. That seemed ridiculous.

Still, he didn't want to seem desperate. He tried to remember movies he'd seen where mothers gave sage advice to their young, horny daughters. "If you give away the milk for free, no one will want to buy the cow...," or something like that. But he was just so happy she wanted his milk...

At least, Tom thought, he should come up with some limits now, ahead of time while he was still thinking clearly with blood in his brain instead of his dick. Bondage was out for tonight, he decided. At least bondage that he couldn't quickly get out of himself. He wasn't ready to give up that much control to someone he'd just met. No other limits came to mind, but he felt reassured that he'd been responsible and at least thought about it.

He was getting tired now and headed back home. He stripped off his sweaty clothes and went to the bathroom to shower. Before stepping in, he looked at himself in the mirror. He turned around and looked at his ass in the mirror. He reached behind him and spread his cheeks, bending over to try and glimpse his asshole. He always felt embarrassed in this absurd position. He'd never seen anyone in the movies trying to look at their own assholes. But he wanted to make sure he looked...presentable. He certainly didn't feel attractive there, but he'd never understood how women could find a hairy dick to be attractive either, so he didn't worry too much. Still, he thought, he should trim a bit so that there wasn't too much hair there.

After manscaping with particular attention to the area behind his balls, he douched his rectum clean with tap water and then took a shower and dressed.

***************************************************

Lindsay felt like a new woman. She liked the girl who had taken the lead in the park. She thought back to how she'd taken exactly what she'd wanted...and he hadn't rejected her. On the contrary, he came in his pants. Ha!

Now she brainstormed her game plan for the evening. The truth was this was her first ever "conquest" and as well as things had gone so far, she knew they could fall apart at any moment. She was faking it till she made it, pretending to be a confident, experienced conqueror of men.

Lindsay went to her bedside table and opened the bottom drawer. She lifted out a strap-on harness and dildo. She'd bought it months ago, almost as a gag, something to fantasize with but maybe never use. She ran her fingers lightly over the purple, plastic penis. It was smaller than any guy's penis she'd ever been with, much smaller than Tom's, judging by the bulge she'd seen and felt in his pants. Still, it was quite a bit bigger than her finger, and she imagined it could be challenging to take up the ass. She'd never let any guy butt fuck her and some self-exploration with fingers had convinced her that she wasn't interested in having her own ass fucked.

She bit her lip as she tried to imagine Tom on her bed, submissively kneeling and facing away from her. In her mind's eye, he looked shyly over his shoulder at her, his face flushed with embarrassment and arousal. She took her time surveying his naked body as she idly stroked her rubber dick. He bent forward to grab the headboard and stick his butt out at her. She reached forward to fondle his muscular buttocks. She ran her hands up his sides, down his spine, back to his ass, kneading his cheeks. He arched his back appreciatively like like a pet enjoying a caress from its owner. He looked back at her again with a nervous smile. She smiled back hoping she conveyed both enthusiasm and restraint, rather than than just the raw lust she felt.

Lindsay paused her mental fantasy long enough to put the strap-on down, slide her pants off, and get comfortable on her bed. She slid her hand down between her legs to better enjoy her fantasy.

She imagined teasing a finger down his ass crack, wiggling it between his cheeks, getting him used to being touched there.

"Stay," she said as she shuffled over to grab the little bottle of anal lube off the bedside table. Lindsay coated her right middle finger and slid it between his buttocks, smearing the cool gel around his anus. With her left hand she lightly slapped his inner thighs to get him to spread his legs a bit more.

Then she clutched his erection tightly and pulled it so it pointed straight down, almost behind him. She didn't stroke him yet, just enjoyed feeling him throb in her grasp as her other hand anointed his tight asshole with oil. She moved the tip of her finger in slow circles around his rim, watching him, teasing him, waiting for him to get impatient.

He tried to thrust his dick in her hand, but she let her hand move forward with him, denying him the friction he sought. She gave his cock a little squeeze to admonish him as she continued to tease his back door with her finger. Now he started to thrust his hips back. She would let him press himself back against her finger, allowing a little pressure to build up, before sliding her finger away from his opening. He grunted in frustration and continued to hump back against her with increasingly vigorous thrusts. Finally, she let him have it, kept her finger rock steady as he thrust back, and watched her finger slide in to the first knuckle. The sudden penetration made him gasp and freeze.

She hooked his ring and pressed the rest of her hand against his ass cheek to control the depth of any further penetration. She didn't enter further but started to stretch his tight ass in different directions as she granted his cock a few slow strokes. She made sure his dick was rock hard so that he was in full slut mode before she resumed the penetration. She pleasured him with both hands, watching with growing arousal as he started pushing back against her finger, taking more inside him.

His cunt belonged to her; it felt hot and tight yet supple. Lindsay's finger was sliding in and out of him now. It seemed that Tom was trying not to make noises apart from his breathing and some masculine (he hoped) grunts, but a few little moans leaked out of him as well.

She pushed the tip of a second finger in alongside the first.

"Oooh that's too much. I...I don't think I can take that," he warned, thrusting his pelvis forward in a bid to avoid further penetration. His escape was limited by Lindsay's firm grip on his penis.

Lindsay didn't retreat, but halted her advance for the moment. "You're okay. Just breathe baby," she pacified. She heard him try to take some deep breaths as she felt his cute butt hole clenching on her fingers. "I know it hurts, but I won't hurt you and it'll feel better soon. Just let me stretch you. Be a big, strong man for me and take it. Can you do that for me?"

Tom didn't say anything, but he didn't move away either. He kept breathing and she felt his clenching get a little less tight.

That was all the permission that Lindsay needed as she eased more of her second finger inside him. Encouraged by his acceptance, she slid her dick hand up to his base and moved her index finger around his dick to encircle his ball sack with her thumb. This fixed her hand at the base of his dick so she couldn't stroke him, but she could pull on his cock and balls as a unit. She pulled him towards her with this hand while driving her two fingers deep into his ass. He whimpered but didn't protest again.

She began to slowly slide in and out of his ass, fucking him with her fingers. "Fuck that's hot, Tom. I love your ass. Give it all up to me baby. Surrender your asshole to me."

Lindsay pulled her fingers from the tight grip of his anus and watched it clench shut. He looked back at her questioningly. She held his eye contact, but said nothing. They both knew it was time.

She shuffled forward now between his legs. She put her arms around him in a light hug as she humped her pelvis against his ass. Her plastic cock pushing awkwardly against his buttocks. Keeping one hand on his hip for balance, she slid her other hand into his hair and kissed the side of his neck. She slowly tightened her grip in his hair, pulling his head back as she sucked on his neck, making him arch his back for her. Tom ground his ass back against her.

Lindsay slid her hand out of his hair, down his spine to pinch the meat of his left buttock, spreading him to get a better look at her target. Her other hand guided her dick to his asshole. He instinctively tried to move forward, away from the rubber dick pushing against his sphincter, but she held him firm by his butt cheek. "This is how you take it for me. Show me that you belong to me baby," she told him as she pressed in through his tight ring.

Back in the present, Lindsay had passed the point of no return, her finger frigging her clit in a frenzy, her orgasm now inevitable. "Oh fuck! Tom, you slut!," she cried to her empty bedroom as she experienced a petite mort.

As she lay on her back panting, she looked back over at the strap-on and it's harness. Best to hide that well before she brought Tom back here tonight. She knew he liked anal play but didn't know how he'd feel about being pegged with a rubber cock. Something to considering broaching with him down the line, with any luck after she'd got him eating out of the palm of her hand and the slit of her cunt.

She showered and prepared for their date. What to wear? For their initial meeting, she'd gone with a hot pink baseball cap, a denim jacket over a low cut white blouse, and a white ruffled skirt with sneakers. Lindsay had found it odd that many of the femdoms she'd read about in erotica dressed in dark colors. To her, men had always seemed the most vulnerable, the most powerless, the most ready to be dominated when presented with pinks and lace.

For this evening's date, she decided on a knit pink mini dress. As she studied her reflexion in her bedroom mirror, she was pleased with how the dress hugged her curves like a tight sweater. She thought she was probably a little overweight, but luckily it was distributed in strategic areas. The dress teased only the very top of her cleavage, but exhibited her breasts well with how form-fitting it was. Her thighs looked good where they exited her hem well above her knees.

She pulled up a relatively plain pair of white panties. She'd briefly considered going all out with thigh high stockings, garter belt, and lacy lingerie, but she didn't want to look like she was trying too hard and she didn't plan on taking the dress off for him tonight anyway. Her outfit was functional, she thought as she imagined pushing him to his knees. From there, he'd be able to service her without removing the short dress. He'd be able to see her arousal clearly through the white panties.

*************

Tom was daydreaming about falling in love with her when a honk from outside interrupted his reverie. He spied Lindsay through the windshield of an older, but well-maintained Civic that was parked outside with the engine running. He came out and waved before descending the stairs.

"Hi!," he said smiling as he hopped into the passenger seat.

"I assume you like Thai food?" Lindsay inquired, returning his smile.

"Yes!" he said like an idiot. 'Why did I say that?' he wondered to himself. He had no idea if he liked Thai food.

"Great!" she said and they sped off into the night.

It turned out Tom did not like Thai food. At least not whatever he'd ordered. It had sounded like some kind of chicken soup, which he thought would be light enough to keep him ready for the after-dinner pleasantries he hoped were in store. But after tasting the first spoonful, he realized that the stuff was spicy enough to need a warning label. Not wanting to admit his mistake, he said he wasn't very hungry and didn't order anything else.

The lack of food was even more of a problem since Lindsay had ordered cocktails for both of them when they'd first sat down. He'd initially ordered a Coke, but she'd overruled him with some crack about how he wasn't in grade school anymore.

Their conversation flowed easily enough, though it stayed superficial. Tom still hadn't learned anything about Lindsay's connection to Megan, which seemed to be an important clue in his quest to understand Lindsay's interest in him. He felt like he might be falling for her, but an increasingly strong sinking feeling in his stomach told him that she wasn't interested in him beyond some casual sex. He recognized he had no hard evidence to base this feeling on, but there were little things. Like how quickly she'd made the relationship sexual or how she hadn't come to his door to pick him up and just honked instead.

When Tom tried to ask her about her connection to Megan, for the second time that day, she dodged the question again.

"Let me give you some free dating advice, Tom. Don't bring up your ex-girlfriend on the first date," Lindsay told him.

"This is technically the second date," he'd retorted playfully but persistently.

"Don't bring up your ex-girlfriend at all then," she said dismissively, "Let's get you another drink," as she looked around for their waiter.

"Oh no, I'm good. I'm a bit of a lightweight when it comes to alcohol actually, and besides," he said catching her eye and moving his hand across the table to touch hers, "I want to be fully aware tonight." He hoped it came across as romantic.

"Nonsense. Don't be a buzzkill, Tommy. I promise I'll take good care of you," she laughed at him.

It stung. He felt a lump in his throat. She didn't care about him, he felt sure now. She wasn't answering any important questions. She thought he was a buzzkill. She didn't respect him.

He went silent, focusing on keeping his eyes dry and dealing with the sour taste in his mouth as he balanced on the cusp of his emotions overflowing.

Lindsay appeared not to have noticed, still looking around for their waiter to order the next round of drinks. Still without looking at him, she added, "Besides, if you get a little buzzed, you can blame the alcohol for being a little slut and coming back to my place to get fucked. I'll still respect you in the morning." She chuckled as she finally returned her attention to him. She quickly noticed something was wrong.

Anger had now been added to the hot disappointment bubbling over in Tom's mind. As much as he wanted exactly that, to be a slut for her and get fucked at her place, he still respected himself. If his past romantic failures had taught him anything, it was that no woman was worth compromising his principles or losing his self-respect.

He stood up suddenly. He held her eye contact and they stared at each other incredulously. He didn't have a plan, but it occurred to him that he didn't want to be here anymore. He was hungry from the stupid spicy soup. A headache was beginning to throb from the alcohol and the emotion.

"I want to go home," Tom said, to her and to himself. 'Am I really going to give up on this amazing girl just because of a few things she said?' he thought to himself. He was so upset that his hopes for this night had been so dashed that he was practically shaking.

"I'm not a buzzkill. I just don't want another fucking drink. And as curious as I am about who you really are, what your association is with my ex-girlfriend, and what it would have been like at your place...I'm not that curious," and with that he stepped out of the booth.

"Wait, Tom!" Lindsay tried to interject.

He pulled up short and turned to her again, "I said I'd buy you dinner." He pulled out his wallet and threw some bills on the table and then turned and walked out of the restaurant.

***************************

"FFFUUUCCCCKKK!" Lindsay thought to herself. This was not how this was supposed to be going at all. She realized now that channeling her inner dominant, macho asshole had not been the way to go. It had felt shitty to her as she was doing it, but she had imagined that she was coming off as dominant, confident, and powerful to Tom. Now it became obvious to her that instead she had been arrogant and selfish.

Tom was walking towards the door, away from her. She glanced down at the money on the table, looked back up at Tom's swiftly departing form, and took off after him.

When she got outside, she saw him about 20 yards down the sidewalk from her.

"Tom, wait!" she called out as she took off in a run to close the distance. A passing family looked at her like she was a crazy person.

"Tom, hold on. Let's talk about this," she tried as she caught up.

"Just leave me alone," Tom replied without looking back. She wasn't sure, but she thought she'd heard his voice crack with emotion.

"Hey c'mon, I'm a jerk. I'm sorry," Lindsay apologized, still hopeful that this could be turned around.

"I just wanna be by myself," he said as he kept walking. His voice had definitely cracked that time. It sounded to her like he was trying to keep his voice gruff and controlled, but he was clearly upset.

"Just stop a second," she demanded as she grabbed his shoulder and spun him around.