[This story involves spanking, whipping, and caning. If that is not to your liking, please read no further. The characters and overall plot were introduced in Chapter 1, and further developed in Chapter 2, but it's not necessary for you to read either before this one. All characters are well over 18.]
My wife Elaine was nice enough to tell me about her private get-together in our bedroom with Gloria Palmer, the young, severe writer and also Assistant Secretary of Women's Affairs in the government. Gloria had put me through some discipline before her session with Elaine. She had me serve her both ways in the tub as she squatted over my face and she also put me in diapers, complete with a locked diaper cover, which had been one of the things I feared most when Elaine began her behavior modification program for me.
It turned out Gloria went both ways. Elaine said it was delightful being in bed with her and I could see my wife's face still flushed from her orgasming with Gloria. I was proud of Elaine for asking Gloria if she needed to be disciplined herself. Surprisingly to me, but not to my wife, Gloria said she'd like Elaine to take charge of her.
Elaine told her she had been naughty and would be whipped. Just being told that I'm going to be whipped arouses me and scares the hell out of me as well. Not only did Elaine whip Gloria on her bare bottom, but she flicked the cane once very lightly up between her legs after ordering Gloria to hold herself open there.
This must be as painful and scary for a woman as being struck on my male equipment would be for me. I don't even like to think about it. But I do have incredible respect for my dear wife Elaine, even if she's putting me through this behavior improvement program, because she obviously can deliver a cruel stroke on a lady's bits down there without injury.
Yesterday, Elaine told me that she would have to be away for work for a few days starting Tuesday. I was surprised when she said that she would be sending me over to her friend Amy's house again. Last time she sent me to Amy, I was introduced to serving Amy when she excreted--both ways. She also wields a mean cane and hairbrush.
Elaine then genuinely surprised me. She said that I would be under the supervision of Amy's younger daughter, Holly, who is 18 and home from school on intersession break. It turns out that Holly has joined a sorority and when Amy mentioned that I'm sent over to her for supervision when Elaine is away, Holly said she would love to be my babysitter.
"I assume I can spank him if he's naughty," Amy reported her saying to her mom. I'm sure Amy told her about how she made me lie in the bathtub and stare up at Amy's orifices, not knowing which one might open and release her pee or poo or both, or even her period flow.
"Mom," Holly then apparently asked Amy, "you mean you had him lick you down there when you had your...period?"
Amy said that she grinned and told Holly that she needed to start acting like a big girl if she expected Elaine's husband, i.e., me, to obey her as his supervisor and disciplinarian. "I did have him wear those tight girly undies I had you wear when you were a naughty girl, Hols," she emphasized.
"Oh, that was terrible, Mom," Holly remonstrated with Amy. "But it might be amusing to have him wear those if he dares to act up with me. I did bring my sorority paddle home, too." Amy told Elaine that she had spoken quite seriously with Holly as an adult who would be undertaking an assignment demanding that Holly behave as a mature young woman.
I learned when my program began that it is not wise for me to argue with Elaine about specifics. I didn't like the idea of Holly supervising me. For one thing, being under the thumb of a teenager doesn't do much for one's self-esteem. Second, Elaine had been making me wear panties; I'll still have them on when I go to Amy's place.
How would Holly react to my having panties on? Might Elaine, despite any pleas I might consider making, make me wear Holly's little girly ones? Would I keep my cool if she decided to conduct a panty inspection like Amy had?
My questions would soon be answered. Elaine told me to get ready to go. She had packed a small case with my toilet articles, underwear, and sport shirts, slacks, socks, and various pairs of shoes. I asked if the underwear meant panties. She nodded yes with a smile. I didn't know that she had spoken with Amy and Holly about what kinds of clothes they could have for me to wear.
I found out only when I arrived at Amy's that I was destined to wear Holly's older sister Elizabeth's schoolgirl uniform from when she was in parochial school. This costume included the well-known plaid skirt, little white blouse, MaryJane shoes, white socks, little white panties, a white training bra, and a school tie.
When I arrived, Amy and Holly greeted me very pleasantly. Amy commented that Elaine had entrusted them with monitoring my behavior, but she had told them that I had been behaving well. She added that she hoped I would cooperate with Holly, who would be totally in charge.
This meant, she explained without any rancor, that Holly would decide what I would wear, where I could go and when, what I would get to eat, and when I would use the bathroom. Holly added that she would decide what time I would go to bed, based on how I had behaved. She noted that if I were being punished with an early bedtime, I would not be allowed to have a light on and would be forbidden from reading, using my phone, or watching television.
"You are specifically not allowed to masturbate, Jay," Holly intoned. "If you break this rule," she continued, "you will be disciplined, and one potential punishment will be putting you in diapers with a locked diaper cover."
She informed me that she would monitor my use of the toilet. "You will ask my permission to use the bathroom," she outlined, "and then when you are given permission, you will ask me to allow you to lower your panties. I may decide to allow you to sit on the toilet with your panties up, as a form of training. When you are given the signal to go, you will urinate and defecate promptly in the sitting position.
"Your panties will not have flies," she informed me. "I will supervise your wiping. If you stain your panties, you will be given points in your behavior book and receive punishment. I know this all sounds grim, but I do hope we will have a good time together."
I smiled and said that my own wife and her mom had engaged in a great deal of effort training me to behave better. I hoped I would please her with my conduct.
Amy excused herself, which I then thought was good, because she had been very dommy when I had been placed under her control previously. Holly smiled and said we would go to her room. When we got there, I recalled my stay there when sent to Amy's home when Holly was away at college.
Holly was wearing a casual outfit common among college girls: flannel skirt, nice white blouse, a thin cashmere sweater, and those chunky shoes younger woman enjoy, possibly because their mothers find them far too uncomfortable to wear for very long. She has shortish (neck-length) dirty blonde hair and attractive legs made more so by her sheer thigh-hi hose. (I suppose I shouldn't even be commenting about how far up her legs her hose goes!)
I wouldn't call Holly a hottie, but she did have that nice college girl look. Her clothes were casual, yet she looked well put together. Actually, she didn't really look like a teenager anymore. She had a nice figure, which made her appear like the kind of girl you'd have wanted to know, and date, and yes, fuck, when you were in college.
"When you were staying here and sleeping in my bed, how did it feel to be using a teenage girl's bedroom?" Holly asked me.
"Your room was very comfy," I said, "and I tried to respect where you had left things. I did not disturb any of your clothing you had left here. Your mother had removed all your underwear and lingerie, so there was no way I could perv with your things. I hope I would have resisted any temptation to do that out of respect for you as a person."
"Mom told me she had required you to serve her in the bathroom," Holly observed. "Will you be willing to do that without being forced? I will admit that it's not something I'm accustomed to--from girls or guys--but may want to try."