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Views: 1217 Created: 2022.01.23 Updated: 2022.01.23

Anal August

Anal August - Jill receives a punishment - part 1

It was a beautiful August day, very warm but with a comfortable cool breeze. A perfect day to take her out wearing only a dress. They had just finished breakfast, she was wearing a long t-shirt and a pair of lacey shorts style panties. As they were cleaning up the breakfast dishes he told her he was taking her out and to wear one of her summer dresses and nothing else, one of the shorter ones about mid thigh in length. After cleaning up she headed to the bedroom to get dressed, he followed behind her after a minute or two. He found her in the bedroom deciding which dress to wear, he pointed one out telling her he liked that one. "You're wish is my command, Sir" she said with a very obvious hint of teasing sarcasm. The sarcasm peeking his curiosity, he asked her if she had taken her enema this morning. She hadn't asked him to help her with it and he seen her go into the bathroom for any length of time.

"I'm sorry Sir, I forgot" she replied, again with the teasing sarcasm but mixed with just a bit of I guess you could call it respectful remorse. She was definitely playing the game!

You know what that means don't you. Now I will have to delay my plans for the day and punish you.

You don't have to punish me, sarcastic emphasis on have. We could just go and do my enema later.

Crossing the room to where she was standing, he grabbed her by the hair pulled her close to him and tilting her head to face him.

You're right I don't have to. But you know I am going to don't you.

Yes Sir she answered softly, her eyes cast down.

In fact you want me to, don't you?

Yes Sir she answered even more softly.

Maybe you don't need an enema today, I'll have to check to see he said with a smirk. Turning her around to face the wall he instructed her to bend over and place her hands on the wall. He pulled her panties down to her thighs and pulled her t-shirt up over her head. I think some Vicks is in order along with a spanking to start your punishment, he said as he removed the stretching plug from her ass. Stay put he instructed as he went to the bathroom to get the Vicks. Returning from the bathroom she heard the distinctive sound of rubber gloves being put on then felt the cold jelly being applied to her hole. The stretching plug had done its job, he was able to insert two lubricated fingers fully into her ass with a single thrust with out any pain. Only a slight sense of stretch and fullness. He move his fingers in and out, bending and twisting them inside her for a minute or two before commenting, Well I don't feel any solid wast in there, I'll have to look more closely after your spanking. Then she heard the cap being unscrewed from the Vicks, she knew it was Vicks because she could smell it, he applied a generous amount to her hole making sure he got it well inside her fucking her ass with two fingers. She could already feel it start to burn, the KY still in her ass added to its effects. Then she felt the stretching plug being reinserted followed be a sharp slap to her ass. Bend over a little more and spread your legs as far as you can, he instructed her. I want a good view of your ass and pussy.

He spanked her ass for several minutes until both cheeks were a nice shade of pink, pausing every so often to pinch and pull on her nipples and smack her pussy and breasts with the riding crop. I think that's enough spanking for now he said, let me take a closer look in your ass. I just need to get the anal speculum and flashlight.