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.
