Modeling Punishment Uniforms Ch. 02

Double Penetration

[Readers will likely find this story more enjoyable if they have read the first chapter These stories include subjects such as bodily functions and sometimes severe discipline. Those who do not want to read about those topics should read no further. All characters are over 18.]

Jan was 45 and pleased that she had recently earned a promotion at the company where she had started at an entry-level job and risen to be Executive Assistant to the boss. Steve, who owned and ran the company, and was in his early 50s, had taken a liking to her and their working relationship was excellent, she thought.

So, when one day he asked her out to dinner and took her to one of the better places in town, she was still amazed when he proposed to her. They were married in a small ceremony a few months later with Steve’s immediate family present and Jan’s sister and her husband.

Steve had three children: Deirdre, 25; Steve Jr., 23, and Kate, just 18. the first two were in college and Kate was applying this year. Their mother, Steve’s first wife, Gloria, had ruled the roost, Jan soon learned. She totally dominated all of them and held weekly sessions where she informed them of how they had failed to meet her standards that week; Gloria then proceeded to discipline each of them, beginning with Kate, and then Steve Jr., Deirdre, and her husband.

Everyone being punished had to lower their panties or underpants and get across her lap. If she were truly peeved, she would take out her thin cane, which none of them was pleased to see. Steve confessed to Jan that he had loved Gloria and that their life in bed had been terrific but that he was hoping for a closer relationship with Jan.

Jan reflected on how well Steve looked for his age and decided she wasn’t in bad shape herself. She had a nice figure, dressed well, and had an inviting face. Steve’s hair had not yet grayed, and he was in good shape from working out.

It was not long, however, before Jan tested the waters in terms of asserting some dominance in the house. She started with her husband, telling him one day as they got ready for bed that he had taken to leaving his dirty clothes spread over the room. He promised to do better, and she responded sharply, “Maybe I should reinforce that with some time across my lap.”

Steve did a double take, but then smiled as he looked at Jan and managed to say, in a small voice, “Yes, Ma’am, I’ve been thinking that you need to take control of this situation.” She sat down on the stool by her dressing table and patted her lap. She had put on her nightgown and it rode up so that when Steve, who had taken off his slacks and now pulled down his undershorts, lay across her lap, his penis was easily caught when Jan closed her strong thighs.

She looked at his pale bottom and began spanking. Their master bedroom suite was located far enough away from the rest of the family so that her loud spanks on his bottom went unheard outside the room. She spanked Steve harder and found he let out some moans but there was no resistance or whining.

Now and then, Jan ran her finger down Steve’s anal crack and teased his anal rosette before running her nail over his scrotal sac and up his firm erect shaft. She finally finished off the spanking when she saw that his bottom had become quite red. She took him by the hand and led him to bed. When she lay back and opened herself to him, he responded as she hoped he would after being spanked: she was definitely wet from spanking him so when he plunged his cock deep into her, she just loved it.

Jan had always been sensual and had known a fair number of men who were very able partners in bed. She could apply her inner vaginal muscles to press on his cock and she then whispered to him that he could cum inside her only when she told him she was ready.

She liked how she was taking control. This was one of her best lovemaking times she could remember, and she told Steve how much she loved him. He responded by telling her that he loved her more each day and he was very happy she had asserted herself.

Soon, she called in each of her three stepchildren and informed them that when they were home, she expected them to help out with keeping the house neat and tidy. Then she added that she was going to hold a session that Friday night at which they were expected to be in attendance.

She asked each of the girls about their experience with their late mother. Deirdre told her that Gloria had been a bitch on wheels and that Deirdre already felt so much better with Jan joining the family. She added that she wasn’t trying to get on her good side but that all three of them would benefit from Jan’s friendship and “supervision.”

Kate was more reserved but said that she had not been as involved until her last birthday when she turned 18. “Mom decided that I could now be punished with Steve and Dee,” she noted. Jan concluded that of all of them, Kate already looked to have a dominant side, which Jan decided deserved to be encouraged.

Steve, maltepe escort Jr., was good-natured and laughed as he said that he understood why others in the family might feel his late mother was a bitch on wheels.

“She was a tough cookie,” he admitted. “And she was a looker, too, Jan. She had a lot of confidence. You’ve seen already, I suppose, that we men in this family are, to be honest, submissive. Among men, we’d be called—pardon the expression—pussies.”

Jan smiled. “I’m not annoyed at that,” she responded. “I know that that’s how a lot of men talk—and think.”

“Let me just suggest one thing, Jan,” Steve Jr. answered. “Everyone really likes you. We like how you’ve brought our dad out of his misery. And we’re glad you’re a part of us. No one will be put out when you assume the reins. If you run things with some kindness, it will go a long way.”

He smiled and said that her coming to join them was one of the best things that had ever happened in the family.

Jan prepared for the Friday meeting. She got together with Kate and talked frankly with the youngest of the brood.

“Kate,” Jan began, “I can already see that you are the outlier here, you definitely have the makings of a dominant. I’d like to help you move into that role here. I don’t mean that I’m giving you any special privileges that the others will be denied, but I like your spirit and your knowing what you’re about.”

Kate looked a bit surprised and even fearful. “I’m pleased you feel that way about me,” she replied. “I’ll try to help and hope you’ll see me as a support, even though I’m the youngest.”

“Let’s start tomorrow, Thursday, if I can take your time for about an hour or so,” Jan responded. “I’m planning on making a trip to the re-education center to get punishment uniforms for everyone. In the morning, before everyone leaves, we’re going to measure them.”

Kate grinned. “I think this could be fun, Jan,” she said, “if you don’t mind my saying that.”

“Not at all,” Jan said in response. “Let me go over what we will be doing. I have a tape measure and a few other devices we may use. We will take chest, waist, and hip measurements of everyone, male and female. They will be told in turn when to take their underpants or panties down. We will measure the penises, flaccid and erect.”

Kate broke out into a wide smile. “That is so cool, Jan,” she gushed.

“Then,” Jan continued, “I’ll have you and Deirdre lie down and spread your legs and we will measure the length of your vulvas. Finally, and I want you to help with this, I have a small rod that will be inserted to measure how deep each one’s rectum is.”

“Jan,” Kate answered, “I’m overwhelmed. You do have a cool side to you. I hope you will keep seeing me as a helper.”

“I do, Kate,” Jan said brightly. “I’m depending on you, in fact.”

The next day, Jan and Kate first met with the two Steves. Jan explained that they both would be measured and that some of the measurement would be intimate and probably embarrassing.

Neither seemed fazed so Jan ordered them to strip to their undershorts. Steve Jr. had the currently popular men’s briefs that came in colors—his were blue—and his dad wore traditional white boxer shorts.

Kate was assigned to measure around their chests and waists. She then measured their inseam and shoe sizes, discussing the sizes with them to ensure that the measures resembled the sizes they actually used to purchase clothes.

Then Jan told them to drop their drawers.

“This may be embarrassing but regard it as part of my regime,” she stated. “I’m going to measure the length and girth of your masculine equipment—your cocks, and first I’d like them flaccid and then erect.”

“This won’t be easy, Jan,” her husband said. “This is definitely stirring us to get hard.”

“Well, think whatever you need to do to lose the hard-on,” Jan said quietly. “I’ll leave you erect so you can deal with that later on your own.”

She took her tape measure and saw that Steve Jr. was flaccid. She quickly measured his length and girth and turned to his father. Steve had managed to lose his erection, so she quickly ran her tape around his cock and then from its glans to the base.

Jan was glad that this part was over. She asked if they needed help getting erect. Both decided that wisecracks were not likely to be welcomed.

Soon she was faced with two stiff cocks. She quickly measured them and then gave what she knew would be a humiliating order. She took out her little measuring rod and told them that she was going to check their anal and rectal size.

“Yes, bend over and assume the position,” she said coolly. They both complied. Jan put on a plastic glove and took a dab of Vaseline and inserted it in her husband’s anus. Then she slid the rod into his anus and slowly pressed it until it was all the way in. She then withdrew it.

There were some smudges on the rod, and she did not embarrass her husband by mentioning them. Instead, escort maltepe she wiped the rod and dipped it in the container of rubbing alcohol. She changed her glove and inserted the rod now after the Vaseline daubing into Steve Jr.’s bottom-hole. She saw that it resulted in his becoming erect again. Then she withdrew it and told both they could get dressed.

They then departed and Deirdre arrived. Jan told Deirdre and Kate to strip. She then used the tape to measure Kate’s bust, waist and hips. She had Kate measure Deirdre’s same places. Then she asked both to pull their panties down and off and lie back on the bed with their legs spread. She took the tape and measured how long Deirdre’s vulva was. Then she turned and measure Kate’s slit. Both were then asked to turn over and spread their cheeks.

Jan again donned her plastic glove, changing it after she did the first insertion, into Deirdre’s anus. The rod emerged clean, but Jan again washed it in the alcohol and inserted into Kate’s small anal rosette again after rubbing the rod with Vaseline. Kate winced and Jan slowed down, realizing that Kate undoubtedly was an anal virgin.

Finally, they were finished, and Jan told them that they could get dressed and go. Kate remained with her.

“Jan, that was a real trip,” she said/ “I can’t believe we measured Steve’s and Dad’s cocks and plumbed everyone’s asshole, much less checking the size of our cunts.”

“Thanks, Kate,” Jan said with a smile. “Come with me now to the re-ed center.”

They arrived at the center and were directed to the clothing counter, where women could obtain punishment uniforms. Jan explained that she was the responsible woman for her family: a husband, a son, and two daughters.

The clerk, a dark-haired Correctional Services officer named CPL Georgia, seemed pleasant and ready to help them. Jan showed her the measurements she had taken and CPL Georgia went back into the stockroom and emerged with a bunch of clothing. She went over every item. For the women, there were tight bras, shiny white panties, little socks and yellow thigh-his, and appropriate skirts and blouses, as well as brown oxford shoes.

“Would you like the bloomers too?” she inquired.

Jan said they would and CPL Georgia then went over what she called “the optionals.”

“I can give you the locks and ties that you can use to lock the panties,” she began. “And we can provide buttplugs in all the sizes you have listed. There are also penis sleeves if you’d like those. They also come with snap locks.”

Jan nodded her assent to all the items CPL Georgia had mentioned. The officer again went back to the stockroom and returned with all these items plus the bloomers, panties, skirts, and blouses for the two men, along with little socks, pink thigh-his, and “sensible shoes.” The officer took out two large cardboard boxes and packed all the clothing, shoes, and “optionals”.

She then produced a printout of the items and asked Jan to sign for receiving them, which was done. She then thanked Jan for coming to the center and said she would be happy to help with any future needs.

Jan thanked her and asked for the name of her superior so she could convey her appreciation.

CPL Georgia smiled and answered that she had a new superior non-commissioned officer “from headquarters” who was spending a few months at the center, SFC Linda. She added that SFC Linda had been a member of cadre at the unit at headquarters that retrained delinquent Correctional Service officers. Jan wrote that down and thanked her again.

When they returned home, everyone was there, waiting for dinner. Jan asked Dee and Steve Jr. to get a light meal ready. Dee looked out of sorts and Jan took her aside and into the bedroom, closing the door behind them.

“You looked annoyed with my asking you to help prepare dinner?” Jan asked her.

“I thought it was not nice that you let Kate off from helping,” Deirdre responded, with tears from the emotions she was releasing. “Just because you took her to pick up the uniforms, does that mean she’s our boss?”

Jan took her in her arms and held her until she calmed down.

“Kate doesn’t need to be controlled to the degree that you and Steve and your dad want to be given direction,” Jan explained. “You thought your mother was a bitch on wheels, but you also grew to feel loved and comfortable with her running the show even when she was quite nasty.”

“She was indeed,” Dee replied, “but then after she spanked us, we all got into bed together. Of course, Kate was involved in all of this only when she turned 18.”

“I think you will all be happy when I get through introducing you to the way I will run things,” Jan said quite plainly.

After dinner, Jan called them all into the master bedroom and went over the weeks’ record. She gigged Steve Jr. for not keeping his room tidy and Deirdre for coming home late when she had duties to perform at the house. Kate was told she left the bathroom in a mess after maltepe escort bayan her shower and then Jan turned to Steve and told her husband that he needed to take care of his chores without having to be reminded.

“So, you are all going to be spanked,” Jan announced, “not that that is new for you. I think you will find my approach to be less demeaning than you endured in the past.” She called Deirdre and Steve up and told them to place themselves over her lap. Steve motioned to Deirdre that she could go first, following traditional etiquette.

Jan told Dee to pull her skirt up over her waist and lower her panties to her knees. Deirdre did what she was directed to do, exposing her dark muff and when she lay across her stepmom’s lap, he broad bottom. Jan proceeded to spank her with her hand, soon producing redness and louder groans and cries from Deirdre.

But soon the spanking was over, and Steve Jr. dropped his trousers and briefs, then replaced Dee on Jan’s lap. Jan looked at his lean bottom and began spanking. She let her finger move down into his anal crack and teased his bottom-hole, then ran her finger further and felt that he was now erect.

“Don’t spurt,” she ordered him.

He was finding her stimulation hard to resist in terms of getting aroused, but he thought of anything else and persevered. Soon he was sore, and Jan told him he could get up and pull up his pants.

It was now her husband’s turn and he too dropped pants and shorts. He also was in good shape and the girls sighed at seeing their father’s frame across Jan’s lap. Jan spanked him hard and he couldn’t resist breaking into some sobs, which did embarrass him. Jan forbore from teasing him between his legs.

When she let him get up, he kissed her on her mouth and she then smiled at him. Then she summoned Kate with her finger and as the 18-year-old yanked her tiny panties down and climbed across her lap, Jan admired her athletic torso and noted her bare pussy. She spanked Kate quite hard but was unable to break her as Kate did not moan or cry. Jan also let her finger touch Kate’s anal crack and her bottom-hole before moving down her furrow into her quim. Finally, Jan said she could get up.

She then told them that she and Kate had secured the punishment uniforms that were now available to the responsible woman in a family in the Women’s Republic and had Kate hand them out to each of them. They had used plastic bags to put everyone’s clothing and shoes separately into a bag. Thus no one saw what the next had received. Kate alone knew what was in hers as she had seen Jan receive all the clothing and then had helped her put them into the separate bags.

“I will have you wearing the punishment uniform if you earn what I regard as an unacceptable number of demerits each week,” she informed the family. “I’m not going to tell you how many you have received but you will need to focus on doing what you have been asked to do around here.

“When you are told to put the uniform on,” Jan continued, “you will not be told for how long you have to wear it. That will be determined based on your behavior once you are wearing the punishment clothing. You have all been informed about the particulars of the uniform. For those of you tempted to misbehave, be aware that I have panty locks and locks for penis sleeves as well, along with butt plugs.”

Later that evening, Jan happened to walk into the living room just as Deirdre was giving Kate a piece of her mind. She told her that she’d better think twice if she was going to be just a little helper for Jan. Kate looked as if she were about to burst into tears.

Jan came in and shot a glance at Deirdre.

“You wouldn’t have talked like that when your mother was in charge now, would you?” she asked Dee.

Deirdre drew a breath but rallied.

“Kate wasn’t involved in disciplining the rest of us when Mom was alive,” she answered.

“No, and now she’s of age and I’ve decided what role she may play here,” Jan responded.

Dee realized she was digging herself in deeper. She tried to retreat.

“I’m sorry, Jan, but it just got to me,” Deirdre now said in a soft voice. “This will never happen again. I’m really sorry, Kate, and Jan.”

Jan decided this was just the time to settle this issue for good.

“No, it won’t, Deirdre,” she snapped, “because now you’re going to take down your panties and lift your skirt. Right now!”

Deirdre realized now that she was truly in trouble. She did what Jan ordered, and she was standing with her panties down, her skirt up, and her hairy pussy on full display.

Jan handed Kate her thin cane. She ordered Deirdre to bend over the back of the couch. Then she issued Kate her instructions.

“I’d like you to give her five nice strokes with that cane,” Jan said coolly. “Make sure they are on the top, middle, and base of her naughty bottom.”

Deirdre now understood that her worst dream had come true. Her younger sister was caning her at her stepmom’s direction.

Kate was just getting past her own inhibitions about punishing her older sister. But she moved behind her, lay the cane across Deirdre’s broad behind, drew it back, and flicked it right across the middle of her sister’s bottom.

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