Mother-in-Law Discipline Pt. 05

In the following months David and Mary's sex life was very active. That is to say, he was unlocked, teased and edged to the brink of orgasm many times a week but rarely allowed to cum. Mary, of course, came many times in each session, mostly from his oral attentions, and especially during her "time of the month".

The most challenging for David was when he was allowed to enter her pussy but not allowed to cum. The penalty for cumming without permission while in Mary's vagina was 24 cane strokes, twice as many as cumming without permission during edging. Not only was the punishment a fine incentive for developing stamina, but the edging practice actually was helping him enjoy the arousal plateau and not rush to orgasm.

For her part Mary was also learning the subtle signs that David was close to cumming and how small reductions in her stimulation of him could hold him back from crossing the line. As grueling as the edging sessions were for him, David was beginning to see that her strict regimen was actually improving their sex life. It was, as she often pointed out to him, one of the reasons why the Female Led Relationship was better for both parties.

It was no coincidence that David and Mary's careers both found a lot of new clients and investors taking an interest in their work. The women in Ann's circle might not be actively involved in the day to day of the businesses they invested in, but their voice still carried a lot of weight. They were a powerful behind the scenes force and it was clear that belonging to their circle made a lot of difference in David and Mary's standard of living. Of course it came at a price; Ann as well as the rest of the women seemed to be much more involved in David and Mary's life, and on some intimate details.

Many of the women had no one to mentor in the lifestyle. Consequently, as the youngest member of the group, Mary was frequently the object of unasked for advice from the older women. Mary was gracious about it, and actually found some of it to be quite helpful in her training of David. Ann's stature as Mary's sponsoring member was also increased, which naturally made the relationship between Mary and her mother much closer, which also had its pros and cons. Most of all, as the only member with a living spouse or submissive there was almost continual talk of having her arrange more entertainment with David as the star attraction.

Mary had taken that idea to heart and thought that her stamina training might be just the thing to show off to the group. Things had progressed rapidly since her admission to the group and she no longer found it necessary to get David's sign off on her plans, though she sometimes still went through the motions to make him feel better about what was going to happen anyway. For his part, whenever David started to have reservations or doubts about the arrangement he had only to be reminded that he was getting more sexual activity than he ever thought possible, not to mention the variety.

It was like this when Mary brought up the idea of showing him off to the women of the group. When he had been orally servicing the women of the group he got the idea that many of them would have liked it if he could have penetrated them with more than his tongue. So David was amenable to the idea from the beginning. Even though Mary would technically be the hostess for the event it made more sense for the location to be at Ann's. Even though Ann was uninterested in seeing erect penises, or having any sexual contact with them, many of the other ladies did, and Ann would not object as it was Mary's party.

Mary and David greeted the guests as they arrived and David served cocktails and hors d'oeuvres in the living room. For all appearances it could have been any ordinary party of friends. Only the smiles and anticipatory twinkles in the eyes of the guests hinted that there was more in store than good conversation, food and drink. After everyone had arrived and had a little time to snack and drink Ann stood up to make an announcement.

"As you know, our newest member, my daughter Mary, has asked to provide us some entertainment this evening. She has been working very hard training her husband and would like to show him off to us, and for us. Well, those who are interested in sampling him," she smiled. Gesturing to Mary, Ann yielded the floor.

"I've been working on David's stamina, and I believe we are at a point where he needs to be challenged on his endurance. So tonight I will be the first to put him to the test, and then as many of you as would like, may enjoy his penis. The rules of the event are as follows:

1. All sexual contact has to exclusively include penile stimulation,

2. He is not allowed to orgasm,

3. If he does he gets 24 cane strokes and must clean up the cream pie,

4. If he attempts to hide his orgasm he gets 36 strokes instead of 24,

5. Any woman he cums in may administer the cane strokes if she desires,

6. In the event of his orgasm as soon as erection can be restored he must again resume servicing the women; unless the Mistress of Ceremonies, me, determines that he will not be able to continue.

"That's about it, shall we go to the 'play room'?"

The crowd began to move to Ann's basement with eager anticipation. For the event a small day bed had been set up next to the spanking sawhorse. The chairs were still there, arranged around the bed and sawhorse. Apparently all of the intercourse was to be witnessed.

"Those who wish to actively participate should disrobe and take one of the chairs closest to the bed," Mary announced as she and David were stripping.

Mary had given David every chance to make a good showing. She had given him a high dose of Viagra and a quickie ruined orgasm before they arrived so he could control his arousal easier. It really was something for both of them to be proud of, and he wanted to make a success of it as much as Mary did. They both knew that he would ultimately fail to hold off his orgasm before finishing all of the women, but he still agreed because he wanted to see how far he could go. The idea of performing in front of others might have seemed off putting at first, but it soon became clear to him that every one of the women in the group had seen him beaten and humiliated before, and he had orally serviced most, if not all, of them, so there really wasn't any reason to be modest or embarrassed.

Mary lay back on the bed and spread her legs invitingly. David was already hard and he could see that she was already wet and ready. He entered her and quickly slid all the way into her warm, wet pussy. As they had previously discussed, their technique was more "business like" and less like their actual love making. David's thrusts were regular and steady, full length penetrations. Since they both wanted the demonstration to be a success they were faced with a bit of dilemma; the less time he was in Mary the longer he would be able to last with the others, but he needed to be in Mary long enough to surpass usual limits for anyone to be impressed with the stamina training. Once he passed the five minute mark he was doing better than 50% of the male population. Mary was having to hold herself off from cumming as well, they had discussed this and wanted the focus to be on how long the intercourse was lasting. At seven minutes Mary let herself go, and with loud moans and shaking she reached her orgasm while David continued to steadily plow her love tunnel. Mary experienced several more shudders and "after shocks" while David was clearly still erect and penetrating her fully. At ten minutes she indicated he should pull out. He was still erect and clearly had not cum. At this point his performance was already better than 75% of men. The women applauded.

Not to take anything away from David's already stunning performance, but he and Mary had already completed what they thought would be the most difficult part - the initial length of time and lasting through her orgasm. Mary assumed that the older women wouldn't be able to stand penetration for long before the thin and delicate skin of their sex would feel raw, so David shouldn't have to last too long with any of them. Then the break between partners should give him a chance to cool down a little.

There might have been a rush for the bed but for some sort of predetermined order everyone abided by. The first taker was a plain and stern looking lady in her late 40's with a tall, thin face. She had on a light green coat, which she threw open to reveal that under it she was only wearing black net stockings and a halter top of the same material. Her bush was sparse, except right around her inner labia, which were thick and long. David would have loved to suck on those lips, and tickle her clit with his tongue but tonight was not about those pleasures.

He doused his member with some lubricant and entered her. She was tight, as he expected but it soon became clear to him that something else was happening. She was clenching her pussy muscles. She was trying to make him cum. She wanted to see him caned!

"Come on," she encouraged in what was supposed to be a seductive tone. "Cum in me!"

Despite her words there was an undertone of vicious meanness. That only made David resolve to fight harder. This was no longer just about sex and stamina.

He adjusted his position to ride a little higher, letting those long labia catch on his cock and pull on her clit with each thrust. Soon he could feel that she was wetter. He kept up his efforts now that he could see his plan had a chance of succeeding.

She had her eyes and mouth closed tight, it was clear she was trying to resist the stimulation that was propelling her toward orgasm. David knew his plan was working, if only he could hold out longer despite the tight grip on his penis. Suddenly he had the idea that he should turn her verbal tactic against her.

"Your lovely pussy is so tight. Do I fill it nicely for you?" he asked in a soft and complimentary tone.

Her forehead wrinkled in a frown and a small squeal came from somewhere in her throat. Then she was shaking all over with her climax.

"NO! Oh GOD NO!" she cried out.

When it was over she indicated he could pull out. David had never seen a woman look so disappointed after an orgasm.

Next was a plumpish woman in a simple flower print smock which she raised to reveal her nakedness. Her bush was large in area but thin. Her labia were small and almost completely obscured by her slightly puffy outer lips. She peered at David through her glasses but didn't reveal much about her mood.

He entered her as he had the woman before and was immediately struck by how loose her vagina felt. David's size was on the upper end of average so clearly she had stretched herself, either recently or over time. There was very little stimulation for his cock and that's when he figured out her game. Although there were no specific rules about him losing erection, the sooner he did, and if he could not regain one in sufficient time, the sooner the whole demonstration would be over. Was that what this woman wanted? It certainly seemed so. David figured out his best strategy was to get her to call an end to his penetration. And since it was unlikely to come from an orgasm he would have to find another way. That's when he figured rigorous thrusting might make her tender pussy skin too sore to continue. Keeping the thought of the last woman's tight cunt, and his lovely Mary in mind, he managed to stay erect while he pushed to one side and another of this woman's vagina. Soon a disappointed lady was telling him he could withdraw, and again without cumming.

The next lady was completely nude and with a welcoming smile that told David she was actually looking forward to some cock. Her bush extended from her triangle down the sides of well defined labia of average size. Like many mature women the bush was not thick but it was natural and she spread herself unashamedly ready for the experience.

It was quite a treat to be with one of the women who wasn't there with a hidden agenda to make him fail. He fucked her slowly and sweetly and when she came he held her close and slowed his movements in time with her de-escalating shivers from her orgasm.

When he withdrew, still erect, she gave him a big kiss right on the mouth and told him thanks.

His next encounter was another woman completely nude and in the mood for real sex. She was wearing a choker of pearls and nothing else. Her bush was downy and extended part way onto her legs. Her outer labia were large and hid her inner lips which were small, but love tunnel opened easily to reveal a wet, pink interior.

As David entered her, she moved to meet his thrusts. The combination of their movements continued and meant David didn't tire so quickly in his legs. Paradoxically that made his concentration a little more difficult. But he focused on the good feelings all over his cock, and not just the head. They worked as a team for almost ten minutes until she screamed her orgasm at the top of her lungs. When David pulled out it was clear he had not cum. Most in the audience were amazed, and a few even thought he might be able to go through all of the women who wanted sexual contact without cumming. Private side wagers were made.

Next was a much older bespectacled woman. She reaffirmed that the rules called for penile stimulation, not necessarily vaginal. After that she removed her false teeth and set about giving David a blow job. Some of the women were shocked, but those who knew her assured the others that she was quite dominant, but just enjoyed the power of having the man's organ so directly under her control.

From David's perspective it was an incredible blow job. He had never had one so good. She knew exactly how and where to put the pressure and how to use her tongue to torment his aching cock. Without teeth she could use her gums to provide unique pressure without risk of the sudden sharp edge of a tooth giving pain that would back him off of his stimulation. Her technique was so good that David felt himself moving inexorably toward an orgasm. He could not control the pace, as he could with intercourse, and his concentration was breaking. He had been in her mouth more than five minutes but it seemed much longer and he was struggling.

At last David could hold out no longer, he grunted and groaned and it was clear that he was climaxing. The old woman kept her mouth glued to his cock until all of his spasms subsided, then she motioned him to open his mouth as she let his load drip from her mouth into his. For a moment the onlookers were stunned to silence then some cheered and others gasped.

In no time David was strapped across the punishment sawhorse. The older lady had deferred to Ann to conduct the punishment. Ann was pleased, David's behavior around her had been exemplary so she hadn't had a reason to discipline him. Not wishing to waste this rare opportunity, Ann really laid on the cane with a vengeance.

The first stroke burned and reminded him how much more a caning hurt after cumming. He gritted his teeth through the next five strokes, but his breathing was loud and labored. At the 7th stroke he screamed out. The pain was so intense. The 8th stroke found that 'sweet spot' where the ass and the thigh meet. David let out a yell that completely expressed the horrible pain and surprised even him with its intensity.

His screams softened some even though the pain did not. He was reaching that breaking point where the body just accepts more pain and can no longer attempt to fight it or resist it. By the 12th stroke David was whimpering. When the 18th stroke connected with his red, striped ass he broke down and started crying, the pain was just too much to bear.

"Please!" (sob) "No more, please!" (sob) He couldn't even beg more because his sobbing was so steady.

Of course Mistress Ann was not moved by the begging and laid on the last 6 with even more force, if that could be imagined. By the 24th stroke his ass was bruised and bleeding in several places, and David was only making incoherent sounds.

Removed from the spanking sawhorse Mary applied some cream to his tender ass and began to rub his member to see if an erection could be restored. Thanks to the cream dulling the pain and the ED drugs in a few minutes he was sporting another erection, though arguably not as hard as his original.

A few of the next ladies opted for giving him oral stimulation, based on how well that had worked before to put him over the edge. But they had neither the talent nor the enthusiasm of the first woman, and no one succeeded in making David cum again. It soon was clear that his erection was losing its firmness, and Mary decided to call a halt to the festivities. When he got as flaccid as he could it was still red and swollen like half erect. To make it up to those who were still expecting sexual contact with David, he was offered for their oral service.

Returning home afterwards Mary was all smiles.

"I just want you to know that I'm very proud of you," she said. For his own part David was pretty proud of himself as well. There was no way he would have been able to hold out like that before Mary's training.

"Thank you! I owe it all to you, dear," he answered. She squeezed his hand affectionately.

"I don't think you are up for me to show you appreciation in the usual way tonight, but I promise in a day or two when you are up to it, we can have a lot of fun," she said with her sexy twinkle in her eye. She was right, sex was the last thing on David's mind at the moment.

"You may not realize it," she said thoughtfully, "but my membership and your part in its success has much larger implications." She paused waiting to see if he would ask any question about it. Then she continued. "Because it has worked out, the ladies are considering recruiting younger women to join their circle." She paused to let that sink in. "You could have some younger and more attractive partners in future events."

"Really?" David answered a little dumbfounded by the prospect but also cautious about appearing too eager at the thought.

"Not only that, but some of them would likely have husbands or boyfriends, so you wouldn't be the only 'whipping boy' in the future!"

David had to smile at that, it would be nice not to have to take the brunt of the entire group's desire to have some male ass to whip. Then Mary dropped the other shoe, so to speak.

"Of course you know that some of the women would really like to see two men together, especially if they aren't gay..."