Disciplined By His Assistant - Sex Stories

Disciplined By His Assistant

... him what age the woman was, because, for him, a spanking was a spanking and was intended to hurt, and, frankly, women much younger than him could hurt just as much as women much older than him.

So, almost reluctantly, he replied, "No, Hannah, I was never spanked." He decided not to explain what his fantasy was.

Hannah took the answer together with the websites he watched as meaning that he wanted to be spanked. So, she replied, "Well that's a pity, but I still think that is a very good way to punish someone who has done what you have done. Tell me though, were you ever caned by any of your teachers or headmaster?"

Tony replied, "No, I wasn't caned either." He didn't add that his fantasy included being caned by a headmistress because he was definitely only fantasising about being submissive to a woman.

Hannah then explained, "As you know I live in a flat just a hundred yards away, and so if you want to know what would satisfy me in this terrible situation, we will both go there, you will take off your trousers and underpants and go across my lap, and I will give you a bare bottom spanking. I will then give you twelve strokes of the cane followed by another bare bottom spanking."

Hannah again looked at Tony to see his reaction and saw that he was actually thinking about it. Well, she knew that she had used Tony's computer at the office and wasn't surprised that someone his age didn't realise his search history was kept.

Tony was thinking, and in fact, thought ...

... just how close that was to one of the favourite videos that he watched at the office. He thought about that for a few moments but then thought about the alternative Hannah had threatened of him being reported to HR. He knew which one he would prefer, and had even fantasised about being spanked by Hannah. He had pictured himself so often across her lap and he was being offered that exact experience right now.

Tony was still worried because whilst he would get the experience he had wanted for so long, he was concerned that it would also get around the office, and so he looked at Hannah and asked, "Would it just be our secret?"

Hannah managed to keep a straight face, albeit she was surprised that Tony seemed about to agree to her truly outrageous demands but supposed that as he was the worse for drink, he won't have been thinking all that straight. However, she replied, "Yes, Tony, I won't be telling anyone."

Hannah also saw the bulge that appeared in Tony's trousers and that confirmed to her that he was going to go ahead with her demand.

Moments later Tony was blushing but also trying not to smile as he replied, "Okay, Hannah, then my punishment it is."

Hannah was surprised at the suppressed smile and saw it as a challenge to wipe the smile off his face before she was finished with him. The thing was, she didn't actually mind him groping her as few men did, given her small breasts, but that wouldn't stop her from making Tony suffer.

So, Hannah replied, "Okay ...