Chapter 3: A New World

The first weeks were the hardest. For a month, I was managing the office on my own, with difficulty. I was caught off guard by how much of the workload the sisters handled. But then I hired a man and a woman, who were both very capable. I invited Bailey to come meet them, just to reassure her.

Duncan was young but a hard worker, and Leila was a grandmother with custody of her daughter’s ten-year-old boy. I was happy to give her an altered schedule so she could be home early after school to watch the youngster. In her 50s and flat-chested, Leila posed no concerns for my wife. And she powered through her tasks impressively.

I was back to coming home in a good frame of mind and able to play with my son with a smile on my face. Bailey taught and supervised in the kitchen, while I made dinner wearing the apron as she demanded, exposing my bare ass.

Afterwards, in our bedroom, it was a different story.

“You overcooked the vegetables, Monkey!” This was her favorite name for me now. “Get on the bench!”

I was wearing only boxers, which I knew to take down. All my tighty-whities were long gone, trashed in favor of boxers. She’d gone through them and scissored out the snap fasteners, leaving the fly gaping and exposing my dangling dick.

In our bedroom, we had a padded bench at the foot of the bed. I would sit there to put on my socks and shoes. Now, it was moved out enough so I could straddle it with my legs apart and my chest against the fake-leather surface and my cock and balls hanging out off the end.

For serious misdeeds, the first step was handcuffing my hands together under the bench, leaving me unable to escape. Then, along with whipping, she would punish my poor dick or squeeze my balls hard enough to cause terrible pain. She had a leather strap, a cane made of flexible wood, and a paddle with holes. (The holes let the air whistle through, making each strike easier on her and harder on me.)

On the other hand, on a day that I pleased Bailey, I got light slaps with her bare hands and loving squeezes of my butt cheeks.

After the more severe punishments, Bailey would demand sex, always with her on top. If I ejaculated before her orgasm, I had to eat pussy until she was satisfied. I also earned a severe whipping the next night.

Where did all this come from? One night, a few weeks into the new regime, Bailey explained her “going to the dark side.” While I was neglecting her, she was looking around the internet for “inspiration” to aid with masturbation. Inevitably, she found all kinds of BDSM stories and videos. Her lusty reactions surprised her. But it seemed the internet offered a 9 to 1 ratio of men dominating women.

When she did come across exciting scenes and stories of women over submissive men, even women-dominated households, she was hooked. She actually overdid her jilling off to the point that her clit got sore, and she had to lay off for a while.

“When I discovered you were cheating, it was a terrible blow. But you convinced me; I believed your apologies and promises. I saw your regrets and tears were all over your face. But you needed punishment. Am I correct, Monkey?”

“Yes, mistress.”

“Should you be punished more for how you hurt me?”

“Yes, mistress.”

“Are you satisfied now with my smaller and milkless breasts?”

“Very satisfied. I love them, mistress. I love you!”

“Ooh, you have pleased me. I want old-fashioned missionary sex after you eat my pussy and play with my tits, tonight only. Would you like that?”

“Very much, mistress.”

I was completely reoriented from my former self. By this point, I wasn’t stewing with guilt, but I was getting off on the punishments. Chemicals must be flooding my brain; I was hooked—as if I was dosing myself with street drugs.

Months after the beginning of Bailey’s regime, I was making breakfast as usual, wearing only an apron. She beat me the night before, leaving visible marks on my bare ass from dropping and smashing a porcelain baking dish. Danny was talking now, not yet in full sentences but making steady progress.

He pointed to my bruised butt and said, “Owie!” My wife demanded I come close. She said, “I’m going to kiss it better, Danny,” and gave my ass several noisy kisses. From that day forward, I wore boxers under my apron. We both agreed our nighttime play should be kept away from our son’s little eyes and ears.

That night, Bailey instructed me on her new policies.

“I’m going to be beating you less often. Instead, I’m going to start ‘pegging.’ That means I’m going to strap on a dildo and fuck your asshole. To start, you’re going to sit on the toilet and push out any shit. Then, you’re going to use two of these, one after the other, to clean yourself out (she showed me two boxes of enema kits). Make sure you’re empty when you come back out.

“Get on your knees and elbows in the bed. I’m going to grease my cock and your asshole. While I’m fucking, you’re going to jerk off until you are about to come. Tell me, then flip over so I can eat it. Are you ready to be my butt monkey?”

“Yes! Yes, mistress.”

“Very well, go into the bathroom now, and take these kits. Leave the door open; I don’t want you masturbating in there, and your shit won’t disturb me as long as it stays in the bathroom. Get moving, and go move your bowels, Monkey.”