The Challenge - Sex Stories

The Challenge

... bedroom and the video feed would go directly to me and only me.” Julie closed her eyes and exhaled deeply. She opened them and stared at Bob. A weak smile came across her face. “I thought you were going to ask me to eat shit or something.” “Ha! Oh goodness no, my dear! Never! I’m a pervert but not that perverted.” Bob laughed. Julie chuckled softly. “Why my son? Why would you want me to do that?” “Truthfully I’m not sure. Perhaps a psychologist would need to figure that out and give you an answer. Maybe if you were my mother, I’d make love to you. Maybe your son came across as awkward and shy to me when I met him last year and perhaps I feel he needs a woman to show him a thing or two. Maybe I wished I had an older woman in my younger years to teach and guide me. It could be any of those reasons and more.” Julie sat in silence, slowly turning around, facing away from Bob to look out his bedroom window, “I don’t know what to say,” she whispered. “I’d say that 20 million is more than enough to support you and him for the rest of your lives, granted you are responsible with it,” Bob paused, nudging her ribs, causing her to jump out of her trance. “You could live comfortably, and not blow it on houses, cars, boats, or whatever. He would have to get a job after college, and not live off that money. If you do all these things I’m sure he’ll have some left to pass on to his children one day.” Julie slowly nodded in agreement. “So you’d install a camera in my room?” “Yes. One that ...

... you can turn on when you see fit. The video feed would go directly to my personal laptop, sort of like a webcam, but in your bedroom.” Bob explained. “Am I the only one you are giving these challenges to?” “Oh I don’t know dear,” Bob said, running his fingers up and down her back. “I’m sure I’ll come up with something for someone else, should I get bored.” “I don’t know, he’s – " Julie trailed off. Her son wasn’t exactly a ladies’ man. They never really talked about sex. “You can take as long as you need, there’s no deadline for this. I’ll pay for whatever new clothes you want, or makeovers, or vacations you want to take him on - whatever you think will help you and him be able to do this.” “What if he doesn’t want to do this?” Julie asked. “Well it takes two to tango, dear.” Julie smirked, looking down to her lap, sighing deeply. She closed her eyes, thinking more about the money, the request, and her son. “A penis is a penis,” she told herself in her head, trying to rationalize this challenge. “If you want to think about it, you can. Let me know what you decide, or don’t. Your silence would be the answer. If I install a camera, and months, or years pass and if doesn’t happen, that’s fine too. As I said there’s no deadline. If my surveillance software captures video footage of you and him having sex, then you get the money. Also, rest assured, I would not upload the video to the internet. I’m not even sure how to do that to be honest!” The old man joked. Julie shook her head ...