Don
Friday night
He made sure to shave as carefully as he could after he'd finished his shower. He didn't need any cuts on his face tonight and was already as nervous as he'd been in a long time. After styling his hair and putting on a minimal amount of cologne, he went to find something suitable to wear. Thumbing through his closet, he swore quietly.
"Shoulda had Jessie pick something out," he muttered to the modestly sized selection of button-down shirts.
As he perused the selection, he tried to dismiss the worries roaming around in his head about screwing the evening up. Was all this effort really worth it? He could end up hurting someone else, and he was just then coming to terms with the incident with Jessie. He still felt like a complete piece of shit for what had gone down between them.
He wanted to be able to blame her completely. For one, she'd been relentless in her teasing and obvious attempts to get a reaction out of him. Multiple times she'd told him that she'd be happy to give him a blowjob or maybe let him jerk off to her. The moment that she'd found out that he was aroused just by the mere presence of her, it seemed to have started a never-ending series of sexual teasing and outright begging for him to use her. Not to mention the fact that she was the sexiest woman that had shown him any interest in him in a very long time.
Still, he knew that what he'd done
should
have been unforgivable. He'd thought that she would come to her senses and hate him, and he wouldn't have blamed her. Even when she didn't, he'd was convinced that his son would, but he'd been wrong about that as well.
Jessie herself had talked to him that very night and had somehow convinced him that it was all going to be okay, even telling him that it was mostly her own fault. In the end she'd told him that she was okay with what had gone down between them.
She was as baffling to him as she was gorgeous.
For a while
he
felt like he deserved to be locked up and forgotten. When she told him that Dex was okay with own father hauling his girlfriend off the counter and fucking her brains out, he'd been stunned. What's more, she'd convinced him to do it again that same night.
That had to make it okay, right?
He honestly didn't know anymore. In the times that he'd been tempted, even begged by her and had managed to decline, it had taken everything within him to do so. He continued to feel like a complete shit for weeks after that, though Jessie was as happy and flirtatious as she'd always been. He'd forced himself on her, and she was still an absolute delight to be around.
To tell the truth, the last couple of months had been the most fun that he'd had since his wife had died. He knew for a fact that she was the reason for it. Between her cleaning naked, trying like hell to get him to let her suck his dick or to fuck her again, and the couple of times that he'd been around her roommate Donna, Don's life had been far more exciting the moment she stepped into it.
The second time that he'd let things get too out-of-hand, Jessie had spent the entire night in his bed. He told himself that he was helping Dex and Jessie both for the reasons that they'd given. Deep down, though, he'd known that he'd
really
wanted it to happen again. God help him, he did.
Once you'd been with the little succubus it was damn near impossible to get her out of your head, especially when she was pleading to let her take care of you. She had so many talents in that regard, it was unbelievable.
The young vixen was incredible at giving head, of that there was no doubt. He'd only been able to enjoy her skills during the night that they'd spent together, but that had been enough to tell him all he needed to know. She seemed to know every trick and skill there was to sucking dick. The sheer joy she seemed to take from it was something he knew was an extreme rarity in women.
Oral sex wasn't her only gift though, and he could vividly recall the way her juicy little pussy had felt when they'd been together. It was tight, thoroughly soaked each time he'd had the pleasure of fucking it and felt incredible when it was contracting down on him in an orgasm. Even when he was fucking her, it seemed like she was intent on making him have more pleasure than she was, and each little thing she did seemed to be geared toward that goal. Her emphatic moans and encouraging whispers in his ears, her hands pulling his hips down harder and harder, even her legs as they wrapped around him when he was plunging in and out; every action had seemed to be begging him to have as powerful an orgasm as he was capable of.
He would chuckle to himself each time he thought about one of the times that they'd had sex, but then immediately regretted letting it happen at all. After a while, he got to where he was determined not to let it happen again.
And so, each morning he would wake up and go stand in front of his mirror. He'd look into it and tell the bastard staring back at him, "never again." It felt silly, of course, but it had worked so far, especially since she'd never stopped her attempts to make sure he was sexually satisfied.
He didn't hold it against her, though. It was just who she was, and he understood that.
Jessie was a large part of the reason that he'd started actively trying to meet a woman. Sure, he was lonely and figured that it was time he saw what was out there, but he felt sure that having another woman around would also help convince the young minx that he was doing okay. He didn't need anyone to worry about his sex life but himself.
He'd initially had some high hopes about finding a good woman to be with. There were lots that seemed at least somewhat interested in him. But unfortunately, the few dates that he'd been on ranged from mediocre to outright laughable. He'd almost gotten to the point that he was ready to throw in the towel.
All of that changed when he started talking with Candy. Even just from texts alone, he could sense that she was a different story altogether.
Apparently, she was the mother of one of the girls that had been at Dexter's party, though he honestly wasn't clear which one she was the mother of. Her daughter and Jessie had conspired to set them up with each other's phone numbers and after texting steadily for a few days, he'd gotten to the point where he'd thought about asking her out to dinner. Before he could work up the nerve though, she asked him if they were even going to meet in person.
So, that's how he found himself in his current predicament. He was steadily approaching 50 and standing in his closet wondering what to wear out on a date with a woman that he hadn't seen or verbally spoken to. He began to wonder if he was crazy for doing this.
After ten more minutes, he finally decided on an ensemble. After putting it on, he left to go and pick her up for dinner. As he walked up toward the door, he saw her step out and smile as she came toward him. He was immediately taken with how beautiful she was. Urging himself to keep it cool and not make himself look like an idiot, he tried his best to do just that. It turned out to be a complete failure.
"Hi," he began. "I'm gorgeous. You must be..." He stammered to a halt as he realized what he'd said, then closed his eyes in embarrassment.
Without missing a beat, Candy burst out laughing and put her hand on his shoulder, almost as if she needed to have help staying upright from laughing so hard at his bone-headedness. From that point on, he'd felt like a kid on the first day of school.
"Hi, gorgeous," she said, highly amused. "That... was adorable."
"Can I try that again?" he asked, shaking his head in embarrassment
"Not for anything in the world," she told him, and he took comfort in the sight of her genuine smile.
Still blushing, he walked her to the car and opened the door for her, then went around to his side quietly hating himself. Taking another deep breath before opening his own door, he steadied himself in an attempt to regain his composure.
The drive to the restaurant that they'd chosen was short, but they were already conversing easily with each other on the drive over. After they parked and went in, Candy asked the hostess if it was possible for them to be seated where they would be able to talk and not be disturbed. The girl did her best to find them a table in a secluded part of the restaurant, and Don quickly became quite taken with his date. They talked a bit up until they ordered drinks, then conversation just started again to flow freely between the two. He began to feel a real connection with her and was dumbstruck at how easy it was to converse.
