It was a cold April day and Jackson Judemann had a date. He wasn’t sure he really felt like going. It had been a long day and he didn’t really want to go out. He was a journalist and he had been out covering stories and conducting interviews all day. The last thing he wanted to do was go meet a girl he probably wouldn’t like in a bar. Their mutual friend, Keyara had set them up. He had known Keyara a while and had always had a mild crush on her. She was single at the moment so he wasn’t sure why she had set him up on this date with Isabella, but whatever. They hadn’t ever really dated before, but they had made out once or twice when they had been drunk.
He sat down on his living room couch, closed his eyes, and wondered why Keyara hadn’t just given him Isabella’s number. Instead she had arranged this date. He took a deep breath, opened his eyes, and got up off the couch. Since had been conducting interviews, he was all dressed to meet someone so there wasn’t much for him to do to get ready. He puttered around the apartment a bit though because he knew he would fall asleep if he stayed on his couch much longer.
Jackson kept his apartment abnormally neat and tidy and he didn’t have a lot to do. He looked at the clock and realized that he still had half an hour before he would need to leave. That wasn’t nearly enough time to get involved in anything. It wasn’t enough time to watch a TV show. But it was enough time to jack off. Jackson’s favorite thing to do to pass the time was jacking off. There were times when he honestly believed that he liked jacking off better than a girl going down on him or even having sex with a girl. He couldn’t figure out why, except maybe because he knew what he liked and a girl just didn’t. He had tried teaching girls to jack him off like he did himself but it never ended up well so he had stopped bothering.
He unbuttoned and unzipped his slacks and dropped them to his ankles. He really didn’t need them to be off all the way so he didn’t bother to remove his shoes. He leaned back on the couch and wrapped one hand around his cock. He groaned involuntarily at the feeling. It truly was his favorite thing.
He began to stroke softly and gently. He grabbed some lotion from the side table drawer and used it to lubricate his hand. Then he slid his hand up and down on his rapidly hardening cock. With the lotion, he was able to slide easily on his dick. He was average sized, about 5 inches. Not too large, not too small. He stroked slowly, relishing in the feeling of his own hand. When he started to feel like he was really rock solid, he quickened his pace. He was moving rapidly now up and down, squeezing at just the right place and releasing when it was time.
He had to stop and add some lotion after a bit but then he was right back to it. He did this often enough that his arm was strong and he had no trouble moving up and down quickly without stopping. That was probably his biggest complaint about girls. They were done too quickly. They would have to change positions or change activities before he was ready. Plus, a girl couldn’t tell how close he was. There was nothing more frustrating than being so close to orgasm and not being able to get off. It was just one more reason why he preferred to do it himself.
Jackson could feel his orgasm boiling up from his balls and he groaned as he felt the first spurt of cum. He moved upward on his cock like he was helping the cum exit his body and then stilled his hand. He was so sensitive right now that he couldn’t handle stroking like he had been but he desperately wanted to be. As soon as he felt he could, he stroked down and back up, but he paused again at the tip. He repeated this process a few more times until he felt that he had no more cum to expel.
Then he grabbed a tissue from the box next to him and got himself cleaned up. He had pushed his shirt out of the way before he had gotten started so he was able to clean up completely and put his clothes back on so he could leave for his date.
He took a cab to the restaurant they had agreed to meet at and he arrived ten minutes early. Perfect. He checked in with the hostess and found that he was the first to arrive. He found a chair to sit in to wait in the lobby of the restaurant and busied himself on his phone playing games. Then the most beautiful woman he had ever seen walked into the restaurant alone. He grinned. That must be her! Jackson was tall, 6’1” and this woman would almost match his height from what he could see of her compared to the hostess. Yet she still wore heels. Confident. Her hair was pulled back into a bun. She was talking animatedly and the motion of her hands was swaying her hips. He felt his cock twitch at the sight. And then his thoughts were interrupted.
“Hi! You must be Jackson. You’re just as Keyara described!” It wasn’t the tall beauty at the hostess stand talking to him. It was a tall-ish girl who had large hips and big breasts looking down at him.
He was so thrown off, he didn’t respond for a long moment. Then he got hold of himself and said, “I am, are you Isabella?”
“I am!” she said brightly and he couldn’t help but smile at her. She wasn’t the most beautiful woman he had ever seen but there was something about her. It wasn’t necessarily a beautiful something but it was definitely an intriguing something. He stood and shook her hand. “It’s so nice to finally meet you. Keyara has told me so much about you!”
Funny, he thought, Keyara hadn’t mentioned Isabella to him at all until she set them up on this date. Even then, Keyara hadn’t had much to say about the other woman. He hadn’t been expecting more information but he was thrown off by the fact that Keyara had clearly given Isabella more information about him than she had about Isabella. He was starting to recover himself though and he replied, “I hope it was all good.”
“Yes, all good, don’t worry.” She giggled and he smiled at her. He couldn’t help it. She was so cheerful.
“Would you like to go sit down?” he asked.
“Sure!” she said and they walked together to the hostess stand. The hostess smiled and sat them immediately. Jackson had made sure he had a good reservation so he could feel like he was impressing Isabella. He wasn’t sure how much of a difference it made for him to have a reservation, but he wasn’t taking any chances.
They were shown to a booth in the back of the restaurant. It was very private. Perfect for a first date, especially a blind date where they really needed to get to know each other. They sat across from each other and looked at their menus. He couldn’t help but think it was awkward that they weren’t really talking now. But they did need to look at their menus so maybe it wasn’t as awkward as it seemed to him.
The waitress came over and they ordered drinks. A few minutes later they ordered food, and then there was the time in between that they needed to fill with small talk. They were pretty successful at it. They talked about work and the weather. Nothing too serious. He found himself surprised that he was having a good time with her. After they finished dinner, she surprised him by sliding over into his side of the booth.
“I hope you don’t mind if I’m too forward,” she whispered in his ear. “I’m just so curious about you.” She winked at him and then she reached over and slipped her hand onto his crotch. She applied enough pressure that he knew she could feel his cock beneath his trousers. Damn!
“Oh!” he said in surprise.
“Shhh,” she scolded with a wink.
“Well you took me by surprise,” he whispered in her ear and then he nibbled lightly on her earlobe. It was somewhat more obvious than what she was doing under the table, but it was more publicly acceptable. Plus they were so far in the back of the restaurant, the only person who could see them was the waitress and she would have to come close to their table to see what was going on. He knew that there was a fairly significant risk of that though, since they had finished their meal and would either want dessert or the check. It seemed like she had the check in mind so they could fool around, but maybe she was happy just fooling around at the table.
She giggled at him and whispered, “That tickles,” when he began to nibble on her neck.
“Sorry,” he whispered back but he nipped at her again anyway just to hear her giggle more. He was starting to lose his focus though because she was underneath his pants now. She had managed to get the zipper down and the button undone with one hand and she had now guided his cock out of the opening. She was stroking him gently and he could barely keep his composure. “Wow,” he whispered. She didn’t respond but she began to stroke a little faster and he found it hard not to buck his hips in response.
She wasn’t bad, really. He still preferred him own hand to hers, but she was doing a good job. He knew that if she kept it up, he was going to cum right here at the table. He wasn’t sure that was a good idea.
“Isabella,” he hissed, “you need to stop or you’re going to have a mess on your hands.” Literally.
“I don’t care,” she whispered in his ear.” He felt his cock spasm at her words. She really didn’t mind having his cum all over her hand right here in a restaurant. He didn’t say another word. If she wanted to deal with the mess, who was he to tell her no?
He continued nipping her neck and earlobe while she jerked him off. He knew that it wouldn’t be long, but she had had fair warning.
“I’m going to cum,” he whispered and he felt her pace quicken. Apparently that was her goal! She stroked him and he bit his lip, trying to contain his grunts of pleasure. He wanted to cum so badly but suddenly he worried that the waitress was going to come over right then. He had involuntarily closed his eyes, trying to contain himself, but he opened them now so he could make sure no one was coming. To his relief, he couldn’t see their waitress. Maybe she was on break or something, but whatever the reason, no one approached their table.
He felt his orgasm build and then break and he was at the point of no return. Even if she stopped stroking now, his orgasm would be ruined but he would cum anyway. He silently hoped that nothing would get her to stop at that point and then he felt the first wave of cum release. He wasn’t sure how far he shot but he knew that he was drenching her hand at least.
For her part, she caught as much of his cum as she could. She brought her hand up from under the table and began to lick his cum off of it. He groaned quietly at the sight. It was hot to watch her licking his cum off her hand. “Wow,” he whispered and she grinned at him and kept licking. Then she kissed him and he knew that his cum was still in her mouth as she did.
At first, he was repulsed by the idea but then it became suddenly very attractive to him. He opened his mouth to admit her tongue and she pressed cum into his mouth on her tongue. Their tongues danced until she pulled back, breaking the kiss. “Thank you,” he said, not sure if that was appropriate or not.
“You’re welcome,” she said and she slipped around to the other side of the booth.