Humiliation Weekend Pt. 01: Jason and Meg

This is the story of a mother of twins who is unable to pay back a substantial loan.

The backers of the loan want a return of their money or if that is not possible, they will accept something in lieu of the money - like quality time with Sally's eighteen year old twins.

Sally, middle age mother, who owes the money

Jason and Meg, the eighteen year old twins of Sally

Sharon, middle age sister of Sally and mother of twenty-one year old Joan

Bess, who lent the money and mother of twenty year old Jonathan, who is gay.

Paula, Doris, and Karen - three middle age ladies who backed the loan and are friends with Sally, Sharon, and Bess.

Please note: This story is a fantasy - it is doubtful that it could ever happen in real life. But we can dream - thus the fantasy. Also, this is part one of a series. Each part follows this format but will involve different people who are humiliated at Bess's mansion.

When Friday arrived, Sally knew she was in trouble - the debt to her sister Sharon was due and she could not pay it back. The two sisters were very close so this was awkward, even though the money lent wasn't her sister's money. Sharon was the front for someone else to whom the money belonged.

Sharon: "Bess is the one who lent you the money, Sally. Bess is my boss and she didn't want you to know she was the lender. That is why the money came through me."

Sally: "I know her - her son is Jonathan, correct?"

Sharon: "Yes, that is right. I had forgotten that you knew her. Maybe that is why she didn't want you to know she was behind the money. She is your friend. Well, Bess has partners, so she can't just say 'okay', we will forget the loan. She will want her money back or something of equal value."

Susan: "What does that mean?"

Sharon: We are going to her office and find out what that means."

When the sisters arrived at Bess' office, Bess put them at ease and they talked a bit about their kids and what they were all doing before getting down to business.

Bess: Here is the deal, Sally. I have partners who backed the loan and they must be paid off. All these ladies happen to know you, and your children. Now, Meg is eighteen - in fact, she and Jason are twins, correct? Yes, and both are entering coll

Sally: Yes, that is so. Jason and Meg, who are very close to each other, also begin college in a few months."

Bess: "Perfect. You now have the chance to cancel the entire loan if you agree to bring Meg and Jason to my estate tomorrow. Primarily Jason, but also Meg to some extent, will have to obey every command that I or Sharon or even you, Sally, give them. No hesitation and no disobeying. If Jason does resist, the deal is off, and you still will have to pay back the money. You will be given extra time to pay it off and the interest will increase, but having the loan canceled will help you and will give all of us, plus my three backers, the thrill of our lives. Now, since both Jason and Meg are legal adults, they can just refuse our requests and walk out. So you, Sally, have to convince them to cooperate."

Sally was not very sure either of her children would go along. She told them that it should be a fun day - bathing suits are required - and Jonathan and Joan would be there, also. Then she had a long, quiet, and serious conversation with the twins and they learned the financial plight of the family, and how their participation could solve all their financial problems. So, they went along and agreed to attend and to 'obey' all instructions given by Bess, Aunt Sharon, and herself.

When they arrived at the mansion on Saturday morning, everyone was smiling and George, after hugging everyone, took Joan, Meg, and Jason for a swim in the indoor pool. While they splashed around in the water, Bess, Sharon, and Sally had coffee. Bess began the discussion by commenting how beautiful Meg and Jason were.

Bess: I mean, your daughter, who looks a couple of years older than her twin brother, is fantastic - solid bosoms and thin hips. And your boy - gosh, he is absolutely gorgeous and a #10 cute face. This is going to be a great day for all three of us. Actually, six of us as my three backers for the loan will also be present. If they were going to forgive your loan, Sally, they wanted to see your kids."

Sally: "That is fine with me."

Bess: "Their names are Paula, Doris, and Karen. And, here they come '' The six ladies introduced themselves and they all sat and got acquainted while the children were swimming. Then Bess got back to business.

Bess: "First, George will not be with us all the time today as he has to work a couple of shifts at his job. He is here now, with Joan, Meg, and Jason, getting them comfortable and at ease. He is also explaining about the obedience thing. Sally, do your children know what is expected of them?"

Sally: "They understand obedience is an absolute requirement, and Jason understands that he will be the only male here (when Jonathan is out) among six adult females and his twin sister."

Bess: "The twins look to be in great shape."

Sally: "Jason was on the swim team at school, and Meg played basketball and soccer. Both plan to continue these sports at college in September."

Bess: "That is great, but now for the tough part. We three run things. Meg and Jason, must adhere to our orders - obedience in all things.

Sally: "I understand."

Bess: "What you don't know is that today is going to involve some nudity."

Sally: "I gathered that was where this was going."

Bess: "And I assume that neither of you have a problem with that?"

Sally: "I know this will sound a bit wicked but I like nudity."

Bess: "So do Sharon and me, especially in young and beautiful people."

Sally: And I know this will sound perverted but I want to see my children, now that they are adults, naked, especially Jason - I bet his cock and balls are as cute as his pretty face."

Bess: "Then we all are a little perverted. Sharon and I feel the same way. Now that George is an adult, I want to see him naked.

The three ladies had some good laughs while this discussion was taking place. But, dear reader, you can imagine how excited Sally was at the prospect of seeing her children in the nude, and to see, and perhaps, touch their delicate sex parts. And soon the four arrived from their swim, dressed in shorts and shirts. George stood behind his mother. He knew what was going to happen and he was practically in love with Jason. Indeed, as the ladies would agree, he had never seen a man this handsome.

After everyone fulfilled their social requirements on seeing old friends (all the middle aged women knew the children), Bess led everyone into the common room where a wrestling mat was set up, surrounded by chairs.

Bess: "Jason and Meg, you are here to settle your mother's debt to your aunt Sharon, to me, and to my backers, Paula, Doris, and Karen. You know all of us and we know you, so you understand we would never do anything to hurt you or cause you pain. Your activities today are designed to pleasure us, and if you do, the debt, which is a considerable amount, will be forgiven. You must obey any of us without questions. If you don't, the debt will not be forgiven and your mother will be in great financial difficulty. Think of it this way - you will be doing it for your mother because you love her. So, will you obey unconditionally?" Meg and Jason said they would and Bess asked Sharon to continue.

Sharon: "Jason, George goes to work in a few minutes so you will be the only male in the house till he returns. Now nephew, you are very special and may receive more challenges than your cute sister. But we all think that you are a beautiful man, so pretty. Now, don't blush like that - you are very cute and we are going to have fun with you. So again, are you prepared to obey unconditionally?"

Jason got very nervous. He was embarrassed at being called beautiful, although he knew he and his sister were. but he didn't like being called pretty. One of his teachers recently told him he was prettier than any of the girls in the school. That stung, although he kind of liked the compliment. But he was eighteen, a legal adult, and greatly preferred 'handsome' rather than 'pretty.' He looked over to his mommy for some help but she pleaded with him to obey.. So, looking down at the floor, he quietly said yes to Aunt Sharon's question.

While this was going on, Meg had her own conflicting feelings. She, like her twin brother, loved being complimented for her beauty. A couple of weeks ago, she overheard two of her female teachers commenting on her pretty face and gorgeous body. At eighteen, she knew her breasts, while not as large as some of her classmates, were perfect for her body. The teachers then commented how perfect her body was and the body of her twin Jason. Neither were skinny nor were they stout. Just perfect for their age. Meg was thrilled hearing herself being talked about like that by two adults. And these two female teachers made it clear in their overheard conversation that they wanted to see Meg naked.

Meg was developing the feeling that she liked being naked and being seen naked. She confessed her feelings the previous evening to her twin and he laughed, saying he felt the same way. Both secretly thought it would be cool if the other stripped right then so the twin opposite could see everything. But Meg thought better of it and Jason thought he was too shy to really strip for his sister. It was a fantasy thought for him and he never imagined that he ever would do it. As it turned out, he never would do it. Someone else was to strip him: Meg and his mother. At the time he never dreamed it would ever happen at all, never mine that his sister and mom would do the honors. Meg's thought process was interrupted when she heard Jason answer Aunt Sharon's question, that 'yes', he would obey.

Bess: "The first activity will be a wrestling match between George and Jason and the loser will have to do ten jumping jacks and ten sit-ups." The room got quiet as all the ladies, knowing that this was a set-up, waited for Jason's reaction.

Jason: "But George is much bigger than I am - this is not a fair match." Bess smiled at this, and Sharon and Sally shook their heads because they knew Jason had fallen into Bess' trap. She pretended to be angry when she got up, got right into the Jason's face, and pulled him up by his shirt and said "Are you questioning the order right after you promised absolute obedience?"

Shocked and surprised by Bess' reaction, Jason mumbled "No, ma'm, I'm sorry."

Bess: "Too late for sorry. For your information, George was going to use only one arm, not two, so as to even things up. I also am angry that you didn't trust me when we all promised you that you wouldn't be hurt or physically abused. You dared to question my order!!"

Aunt Sharon, Paula, Doris, and Karen all joined in saying how disappointed they were in Jason that he would think any of them would do him any harm. He talked back to say he didn't mean it that way but it was too late. Bess grabbed the boy's hand and she and he stood in the middle of the wrestling mat with everyone else seated around and close to the mat.

Bess: "Jason, your punishment for questioning my order and insulting these ladies is that you will wrestle in the nude." The room got silent in a hurry. Jason looked at Bess in horror, turning very red. Meg, with a slight smile, thought 'At last, I get to see Jason's cock and balls - oh, my god!!' Sally didn't hide her smile - she grabbed her sister's hand and thought "I am going to see my boy naked - I am getting wet just thinking about it." The others, including Jonathan, were thinking on similar lines.

When Jason had recovered himself, he said "I can't do that. I can't get naked in front of my sister and mom."

"Really?" said Bess, ignoring that the boy was questioning and disobeying her. "Do you love them?"

Jason: "Of course!"

Bess: "And yet you would ruin them financially just to avoid being a little embarrassed? Don't they love you?"

Jason: "Yes, they do but that doesn't mean they should see me naked."

Sally knew she had to help out. She needed the money and Jason had to do this. But to be honest, Sally wanted her son to strip, she wanted to see her pretty son naked before her eyes. She grabbed Meg's hand and they went up to the boy who was near tears.

Jason: "I can't do this. I don't want you to see me naked."

Sally: "Jason, Meg and I love you - we don't care what you look like naked - only our love for each other counts. And we need to cancel this debt."

Meg, taking Jason's face into her hands and kissing him on his smooth cheek: "Brother, I love you and don't give a shit if you are naked, clothed and upside down."

Jason, almost in tears, nodded his assent. As Mom returned to her seat, Bess ordered Joan to join Meg on the mat. "Joan, take Jason's shirt off," Bess ordered. Joan looked at her cousin in the eyes and then kissed his cheek, moist with tears. She raised the boy's arms and slipped the shirt off. She smiled when she saw the small batch of soft brown hair on his armpits and even gently tugged on them.

Bess: Jason, put your hands on the top of head - we don't want the view obstructed. Meg, you will have the honor of finishing stripping your brother."

Readers - what a scene that I am trying in my own inarticulate way, to present. One scared eighteen year old was having his genitalia exposed to his mom, sister, aunt and cousins, including one very gay young man who was about to cum without even touching himself. Can you imagine the expressions of anticipation on everyone's faces as Jason, hands on his head, stood there with everything private on his body exposed for them to look at. Meg thought that her brother looked sensational and stared at his male package, admiring his glistening pubic hairs and estimating that he brother's cock was a good three inches long. Imagine Sally, Jason's mom, whose debt caused her son to be so embarrassed, staring at her son's perfect sex organ, noting how perfect it fit with his body. Jason's aunt Sharon was admiring her nephew's scrotum, seeing his balls hanging loose and low, and how she would love to massage those balls.

Sally looked at her son's face. His eyes were closed and he looked so unhappy. Did he feel humiliated? Embarrassed? Violated? Oh, how she wanted to just hug him and tell him that everything was okay. But she couldn't do that but what she could do was to admire the beauty of her son. While she and her daughter, sister, and niece were soaking in the image of beauty before them, Bess called her son Jonathan to her.

Bess: "Now, my son, be careful wrestling Jason. I don't want any injuries, especially to his penis and testicles. Understood? And, most important, when you flip him, hold him down in a way that his mother and sister can see everything he's got. You know, legs sprayed out so that his entire undercarriage is visible."

Jonathan: "Are you wearing your small camera?"

Bess: "You mean the one that no one can see?"

Jonathan: Yes, you know which one I mean - make sure you get a good picture of Jason when I get him in place."

Bess: "Just for you, sweetie." She gave her Jonathan a kiss and whispered how much she loved him. "Okay," Bess continued, "George and Jason on the mats. Sally and Sharon, you and your daughters are to sit next to the mat so you see everything up close."

Poor Jason. Here he was supposed to wrestle his good friend Jonathan. But Jonathan was going to be fully dressed and he was going to be fully naked. He couldn't even look at his family sitting close enough to him to touch him, but he just knew that they were staring at him, in particular, his cock and balls.. The two began the match by crouching and circling each other looking for an opening. Meg could not take her eyes off her brother's genitals. She was fascinated how his cock and balls swayed this way and that way.

After a minute, George suddenly grabbed Jason and lifted him up and did a soft slam dunk on the mat. The seven ladies sitting right in front got to see Jason's entire sex organ flop every which way as he landed on his back with his legs toward them George quickly spread Jason's legs wide open so that Jason' scrotum, perineum and butt hole were in full view of his family. When Sally saw her son's small, puckered anus, she gasped. All of the ladies were looking at all the intimate secrets of Jason's body, secrets he had tried for years to keep hidden. And George held Jason sprayed out long enough so that everyone had a long and memorable view of Jason's sexual parts and so that his mother could get a couple of pictures taken.

George finally lifted up Jason, who was red with humiliation. Sally came over to her naked son and hugged him tightly. Meg patted her brother's butt. Bess suggested time for a quick lunch and that Jason could get dressed. As the younger set walked out, Bess called all the ladies around her and they all saw the pictures of Jason on the ground and displaying all his sex. The ladies seemed fascinated at what they were watching. Butt hole,perineum, scrotum, penis - they could see all. The ladies giggled and laughed but also knew they were watching something very beautiful.

Bess was having the best time. She had done this sort of thing with individuals or couples, but never a family and never with her relations. She even had a term for the event: Humiliation Weekend. And what a start - to do this with her extended family, to people she had known since their births. After lunch, Bess announced that because of these intense activities that Jason and Meg were going to be required to do, they would have to undergo a short physical exam to be sure they are healthy enough to do the challenges safely. Now, Sally and Sharon, as well as Doris, Paula, and Karen, knew this was just a sham - just another game for the mothers to enjoy and was less an exam and more an intimate massage. Elizabeth Hold, a friend of Bess, was a real doctor and often participated in these 'humiliation weekends' and she arrived to conduct these 'exams'. So everyone proceeded to the playroom where Dr. Elizabeth Holt was set up.

"Now," Elizabeth announced, "I will examine Meg first. And moms and friends will be attending to make sure I do a thorough job." The two subjects were taken aback by these arrangements but knew enough not to question. And really, how surprised could they have been?

"Meg, dear," Dr. Holt said, "you will be first and I need you to get on the table and lie on your stomach. But first, we need you to be very naked."

Meg knew this was coming and although very nervous, accepted her fate. But her twin brother's reaction was much more excitable - finally, he was going to see his sister naked, something he had been dreaming of since puberty came along. Bess then said "Sally, you will have the honor of undressing your daughter."

"How appropriate," said Dr. Holt.

"How wonderful," thought Sally.

"How I wish I was stripping her," thought Jason.

Quickly, mom got her daughter down to just her bra and panties. She stepped behind Meg so that everyone had a great view when she removed Meg's bra. When Meg's perky, and petite bosoms were revealed, Jason almost had a meltdown. And Doris and her friends, as well as Bess and Sharon, were a bit overwhelmed seeing the girl's ample breasts with her pert nipples. Then off came the panties, and Jason was looking at his twin sister's vagina for the first time. He just kept staring and admiring his sister's soft pubic hairs and just being able to see her luscious labia lips. Stunning. And being the only one naked made the sight of Meg's nudity even more stunning. Now she knew how her brother must have felt when he was the only one naked.

"Jason," Dr. Holt said, "I want you to sit at the end of the table so you have a close-up view." The doctor helped Meg up on the table and placed her on her back. "Jason, it is time that you saw and learned about the mysteries of the female sex, and who better to display these mysteries than your own twin sister?"