Jack wondered what Amy had in store for him. She was planning their date, just as she had planned their previous encounter at her house with five other women, bondage, and public humiliation. Well, she was definitely a take-charge sort of woman, in keeping with her persona as a dominatrix. He decided to just ride the wave. He decided to call. “Hi, Amy. I was wondering what you might be planning for our date Friday? Or do...

Jack was getting sick and tired of looking for jobs that didn’t seem to exist, or were already filled by the time he got there. He scanned the want ads again one morning, hoping to find something, anything. Oooh. There was an opening at the library, at the circulation desk. He already had some library experience from when he was in college. He could certainly check out books until something better came along. He reorganiz...

On Monday morning, Jack called Charlene to see what she wanted to do on their date. “Hi Charlene, how are you?” “Oh, I’m doing wonderfully! I’m glad you called. I was going to call you today.” “Good. I wanted to ask you if you wanted me to bring anything tomorrow night.” “About that. I think I’m going to have to cancel.” “Oh, I’m sorry. Is everything okay?” “Yeah. Um, let me just tell you straight out. I met somebody, and...

Jack was glad he had an extra day to recover from his date with Sue. She tired him out. He thought about her on Friday morning as he washed his face and brushed his teeth. Then he considered Amy. So different in so many ways, but Amy was more of a mystery. Tall, slender, with long red hair, her striking appearance seemed at odds with a reserved personality. He wondered what his date might be like. He decided to call her....

Jack had a date with Sue for Thursday night. Dinner at her place. That should be cozy. He was still recovering from Saturday’s performance, or orgy, or whatever the hell that was, followed by some playing around with Aunt Peggy. She didn’t want to have intercourse, but lots of other things were possible. He lay on his bed, and thought about everything that happened on  Sunday evening. It was all a swirl of amazing sex. He...

Jack settled in for a round of masturbation in the bathroom. He had all his equipment: his laptop, tuned to his favorite porn, his Aunt Peggy’s bra and nightie, a pack of her Winston Red 100s, a couple of belts to tie up his man boobs so they stuck out more while he teased the nipples with his fingers or the cigarettes. Quite some fetish he’s developed. He was glad to be out of the college dorms, and happy to not have to...

They sat in the coffee shop on their second date. A book group wasn’t the worst place to meet interesting people. Jack had asked her out, and Valerie was curious enough about him to agree. There was something about him that she liked. She wasn’t sure what it was. The first date was nice, dinner and a movie. They were becoming comfortable with each other, and Valerie decided to reveal herself a bit. “Oh, this coffee is rea...