Sugar Daddy Chronicles Part 1

It was Friday afternoon and his work was done for the day. He had a whole weekend free. Normally, he’d be spending at least a part of the weekend with Primary Sugar Baby. But, they’d been together Monday and Tuesday and that encounter, though mostly beautiful, had ended on a rough note.

Now, Primary Sugar Baby wasn’t returning his texts. Or, at least not in any substantial way. She certainly wasn’t available to meet him anytime that weekend.

He’d met Primary Sugar Baby two years before on a site dedicated to helping facilitate such connections. She was brilliant and beautiful and they’d been on and off since those first few messages. He liked her a lot. And, if there was a consistent man in her life over the past two years, it had been him.

Anyway, there would be no Primary Sugar Baby this weekend. Still, he was feeling tense and stressed. Plus, he really hated to think of Primary Sugar Baby being upset with him.

So, he logged back on to the site where he’d first been introduced to this type of arrangement. He knew there were a variety of women there. He was fairly sure he could find someone to help him get through days or weeks of whatever was going on with Primary. Who knows? Maybe he’d find another to take Primary’s place.

In just a few hours, he had a number of interesting names and profiles in his inbox. He’d begun texting with a few of them. Exchanging initial pleasantries, pictures, and discussing what type of arrangement might get them started.

He went out for a drink and kept an eye on his phone. No, he would NOT be meeting in a parking garage in someone’s car for $100 and a blowjob.

He did, however, have a few possibles. Among them, a particularly eager nursing student named Kat. She was 25, dark hair and eyes, and seemed both funny and rather smart. He liked her appearance, but especially enjoyed the way she made him think. Plus, she was naughty without being gratuitous.

He’d had too many drinks to drive home by the time he left the bar, so he walked to a hotel downtown and got a room for the weekend. This would also allow him to meet someone and take her to “his place” without taking her to his home.

Back in his room, he watched a basketball game and made some more effort at finding a weekend sugar baby.

Kat kept texting him, and as the night wore on, she described in some detail the things she’d like to do to him.

He showered and then sent her a pic of him with a towel placed strategically. She liked his look - he was a bit nerdy in clothes, but with no glasses and freshly showered, she could make out the outline of muscle in his arms and shoulders. She also admired his relatively flat stomach and defined pecs. He was a runner, and it showed. Plus, without his glasses, his dark eyes seemed to invite her into the scene with him. She would have guessed him at least 10 years younger than the 45 he claimed. He was intense. She imagined him kissing her, imagined tasting his skin with her lips.

He asked if they could meet Saturday afternoon or evening, but she said she was doing a project with some friends at school.

So, he spent Saturday checking out some games, having a few drinks, watching a bit of porn, and playfully teasing the two other women who’d caught his attention. Perhaps one night the following week, they’d get drinks. For now, he wanted Kat.

Sunday came, and he looked at his phone when he woke up. Kat had sent him pictures already and told him she wanted to see his body without the towel. Since he was naked and in bed, he took the opportunity to take a pic of his semi-aroused dick under the sheets. She texted back that she wanted him inside her.

He said she was welcome to it. They agreed to meet for drinks later that night after Kat revealed she had Monday off from school and work. They reached an agreement on an arrangement and also agreed they’d start with drinks.

They met at the bar across from his hotel - the one where he’d been drinking on Friday. They connected easily, and he could tell she’d be willing to join him in his room.

He led her across the street and took her to his room.

They talked for a minute sitting on the bed, but he couldn’t resist her face and he touched her cheek and pulled her to him. He tasted the sweetness of her lips, savored the essence of her skin.

Almost immediately, her hand was on his lap, gripping his cock through his pants. He loved the feel of her, the scent of her perfume. He loved the way she wanted this, wanted him.

He pulled the shirt over her head, she unfastened her bra and released her lovely breasts. He immediately felt them in his hands, let his mouth taste the skin of her nipples. He wanted her, loved her scent, her skin, her heat beneath his lips and tongue.

He placed kisses on her shoulders, her neck, her breasts, and his hand worked the buttons on her jeans. She pushed them down, off, kicked them to the ground. His hand covered her center, felt her heat through black lace. He placed a finger between the pink folds of her pussy and then brought it to his lips. He was on fire for her, his head now between her legs, his lips parting pink, tasting the inside of her. Now, his lips on her clit, his fingers inside her, rocking her body in rhythm as her hands gripped his head. She was cumming, and cumming hard. He kept licking and sucking and tasting and pleasing. He could not get enough.

After her climax, she leaned back on the bed and he climbed over her, tasting her lips, letting her taste her juices on him. His cock was rock hard, against her thigh, and she stroked it with her hand.

He grabbed the base of his cock, placed the head against her clit. He looked down at her, and their dark eyes met. He looked at her, watched her expression as his throbbing member penetrated her flesh, felt the tightness of her. She told him she was going to cum again - the sensation of him on her, the kissing, his thick cock - all of it was too much and exactly perfect.

He told her to cum for him, to cum on his cock. He felt her cunt squeeze his member, felt her body tense, and he fucked her. Fucked her hard and all the way through her orgasm. Then, he kissed her as he held his cock inside her, kissed her as he was thrusting in and out, kissed her as he ground against her body, kissed her and then pulled his hard, wet cock out of her, held it in his hand, shot his hot load of cum on her stomach.

He nearly collapsed on her. She held him, hugged him. Their bodies stuck together.

She told him that was round 1. Then, she got up and poured them both drinks from the bottle of bourbon on the dresser.

The would drink and fuck through the night, and she woke him in the morning with her mouth on his cock. She took all of him, his cock and his cum, then wiped her lips and kissed him goodbye.

He texted to tell her how amazing the night was. She texted to tell him she hoped to see him again. Then, she checked her Venmo. He’d met their agreement and then added generously to it.

She couldn’t wait until next time.

He filed her away as a very, very suitable replacement for Primary if that ever became necessary. For now, he was going to sleep.

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