Sly Mother-in-Law to Be

Robert had met Sandy's mother once or twice before they were engaged. Then there was the ritual meeting for Char's blessing. Char was getting a little middle-age heft, but she was about as attractive as she might ever have been, that is 'average'. Robert felt slightly guilty, it seemed harsh, but he couldn't help thinking about the contrast between her and her gorgeous daughter.

Sandy embraced the modern feminism, but she wasn't fanatic about it. For example, she didn't require him to wear a chastity device, preferring him to be on the honor system. She said his word should be enough. Likewise, securing her mother's blessing on the wedding was mostly about respecting her mother's wishes, and less about giving her authority over Robert. In fact, Sandy's instructions had been to perform the oral service, but that he was not allowed penetration or an orgasm and that mother would not have the right to ask for these services again. All of which was fine with Robert. He'd heard stories of guys who even had to please their fiancé's grandmothers and accept that they might require that service at any time in the future. He had apparently done well enough because Char was happy to give her approval to the union.

This was the first time they had seen her mother since seeking her blessing. Robert wasn't thrilled with the idea of them spending the night at her mother's but it made the most sense. They had been visiting his family, and it was just too long a trip back home without a stopover. Char was about half way. It just made sense to stay with her for the night. She had a large two story house, kept in the divorce from Sandy's father many years ago. Sandy had never volunteered any details about the breakup, and it seemed like a non-issue, many of their friends' parents were divorced.

Char was being a bit 'old fashioned' and insisted that the young lovers have separate bedrooms. Robert's hopes for a 'midnight' rendezvous were quickly dashed.

"Sandy, you will have your old bedroom. I've kept it just like you had it when you moved out. Robert, I turned the guest room into a craft room. It was just so easy for me to work in there at night and then just a few steps to bed when I was tired. There's a den downstairs with a sleeper sofa. I hope you'll be comfortable." Then almost as an afterthought she added, "Oh, kids, just so you know, living all alone I'm used to taking certain precautions. I keep the alarm on at night. There's a motion sensor on the stairs."

"I'm sure it will be fine, Ms. Sanders."

Dinner conversation was mostly between Sandy and Char and centered around the wedding plans. There were subtle questions from Char about the degree of control Sandy was going to exercise with Robert, but it was gentle persuasion. Robert knew enough to simply be quiet and respectfully support whatever Sandy said if she indicated he should chime in. Quietly, Robert was beginning to see how very grateful he should be that Sandy wasn't as hardcore as her mother. In addition to being in strict chastity, his number of orgasms would be severely restricted from what he and Sandy were currently enjoying. Robert liked being on the honor system, it felt good being loved and trusted; but it also felt better to be able to cheat, just a little, if things got a bit too frustrating. He rationalized that masturbation, especially if he didn't cum, wasn't really violating his promise to Sandy.

Everyone went to bed early as it had been a long day. Robert couldn't sleep though. The sofa bed was comfortable enough, but all the innuendo about sexual control and the fact that he couldn't be next to Sandy had him horny. If they had slept in the same bed, chances were they would have both fallen asleep immediately; but being denied the opportunity had him imagining that she might have at least allowed him to eat her to orgasm. He was already learning to take some sexual satisfaction from her sexual pleasure. Sandy was pleased at this development. Right now, in this moment, all he could think about was how his dick needed to feel some stimulation. He quickly clicked his phone over to one of his favorite porn sites and gently stroked his penis to a nice, full hard on.

"I didn't realize you were still awake," Char said calmly. "I came down for some warm milk to help me sleep and saw your light on."

Robert was startled and rushed to cover himself. Then he noticed that Char was standing over him in a see through yellow night gown. Her large breasts and dark pubic patch were visible. Her expression was a little stern, and he panicked wondering what she would do next.

"That looks like an erection you're trying to hide. Does Sandy permit you to masturbate?"

"No, she doesn't want me to. But I wasn't really...I mean I don't cum, usually." His flustered responses sounded like lame excuses even to himself.

"So what, exactly, are her orders or your promises, however you two like to refer to them?"

"No playing with myself," he answered shamefacedly, "certainly no cumming."

"So you were breaking the rules, and if I understood what you meant when you said 'usually', it sounds like you have broken the big one in the past too."

"Yes, Ma'am," he answered ashamed and afraid. "What are you going to say to Sandy?"

"I don't know, yet," she said coyly. "It depends on how well we understand each other and our relationship."

"What do you mean?" he asked uncertainly.

"Do you know why the tradition of sexually servicing the mother of the bride-to-be came about?"

"I suppose it's to honor the woman who gave birth to the woman he wants to marry and to show respect for her authority in the family."

"Nicely quoted from the marriage guides. Anything else?"

"Well I suppose some are right when they say it's to ensure that the man knows how to please a woman."

Char laughed, "Yes, that too. But there are other reasons that are more practical. The man learns early to appreciate and please a woman who is no longer in her youthful prime so he will still love his wife when she too is past her youthful beauty, and the older women of the family can still enjoy the attentions of a young and fit male, all within the safety of their family. But Sandy has turned her back on that. I don't care if she doesn't require chastity of you. I think it's stupid to trust a man that completely, but that's her business. I was hoping to still enjoy sex a little, without having to take silly risks picking up men for a little fun."

"I see," Robert said as slowly he thought he knew where this was going.

"Since you have already demonstrated that you have little problem breaking my daughter's rules, breaking the one about further sexual contact with me shouldn't be too difficult for you. Or I can just tell her what I found you doing."

"Please don't say anything to Sandy!" Robert wasn't sure how Sandy would react, but deep down he felt sure it wouldn't be good - since the promises were secured only by his word, it would be worthless; if it wasn't already. And after all, he would just be doing what lots of other men were required to do. "I'll do anything you wish, just name it, Ms. Sanders."

"Not so formal, dear. When we're alone like this call me Char. Ms. Sanders or Ma'am if I have to punish you."

She smiled and pulled up her gown revealing an ample breast and her bushy pubic triangle.

"Oh, in case you are thinking that confessing your 'minor' infractions of her rules will not be a big deal to her, you're wrong. Breaking promises, and generally not being trustworthy were the reasons her father and I divorced. Sandy was terribly disillusioned with him, it took a lot for her to be able to believe any men could be trusted."

"But if she found out about this, wouldn't that be worse?" he asked dumbfounded.

"Certainly for you! A man who can't keep his promise not to masturbate could hardly be believed if he claimed I came on to him. All the more reason to be careful and keep your mouth shut, wouldn't you say?"

"Yes, I suppose so." Robert knew he was defeated.

"Good. Now as I recall you had no trouble performing with me before. Let's start like that again."

She let her night gown drop back down while she positioned herself over his face. He was looking up at her furry nest and the full lips he had suckled on not long ago. A lot more than her approval for his marriage rode on his performance tonight. He dove in with his tongue determined to give her a better orgasm than he had before. Char must have been horny herself, because she quickly responded with low moans and grinding of her hips. His tongue probed her vagina, then licked her labia, inside and out in flat strokes. He used his lips to draw hers out so he could gently pull on them, indirectly stimulating her clit. Then his tongue was curling around her hard little nub. Char's breathing got heavy and he could feel the muscles in her legs tense up. Soon was covering his face with her fragrant juices and shuddering to a massive orgasm that must have lasted at least 30 seconds. When she finished she raised up from his face and grasped his rock hard cock.

"Now you are going to get to put this in me, as deep as you can go. But you don't have permission to cum. Got it? If you cum, I'll tell Sandy about the other stuff."

She lowered her sex on his pole and he watched as it disappeared deep in her moist folds. The sensations were exquisite. He thought her pussy was remarkably tight for a woman her age, though he didn't really have any experience to compare it to. Several times he got close to cumming and begged her to let him, but Char just shook her head and slowed down and let him recover his composure. One time she added, "I won't go against my daughter's control of your orgasms, besides I think she lets you have too many as it is." She rode him to a couple more orgasms before she got up complaining that her knees were not up to any more. She cradled his balls in her hand.

"Are these sore?" she asked with the tone of a caring mother.

"Yes, I've got a terrible case of blue balls," Robert answered honestly.

"Good, dear. Now remember, no cumming. And I'll know if you aren't in pain at breakfast."

The next morning at breakfast Robert was sitting down gingerly because of his sore and swollen balls. He passed it off to Sandy as having slept in the wrong position on the strange bed. Char just smiled and apologized for the old sofa bed. He was getting away with it and he'd paid to secure his other secrets. He was done. He could forget about everything that happened last night. Then the bomb dropped.

"You know, Sandy," Char said, "I've been thinking. I should sell this house and move to your city. One day you two may have a child and I could be your free babysitter. I don't need this much room and I have no friends left here anyway."

Robert was frozen in silence.

"Oh that would be wonderful, Mom!" Sandy exclaimed. "Wouldn't that be great, Robert?"

Char looked at Robert with a knowing glance.

"Why yes, dear. It would be wonderful," he answered with as much enthusiasm as he could muster.

***

Robert could see how this had to play out. It was a brilliant move. Char would continue to blackmail him into servicing her sexually. Their continuing activities would increase their chances of being discovered. If discovered it would be disastrous for his marriage, but it would be his marriage that failed, not the relationship with Mom, she probably had a way of making it look like Robert initiated it. Sandy would be in the perfect place to adopt a stricter stance with regard to men in the future, just as Char had always counseled. If Char was successful lobbying Sandy to adopt a role that allowed Robert to take care of her needs then she wouldn't have to worry about discovery but she would still have blackmail power over Robert because of his cheating on the masturbation rules. Robert's only way out of being blackmailed was to lobby Sandy for the use of chastity. He would have to sell it not as a substitute for his trust, but as something else, a hot reminder, something. Frankly it seemed more likely that Char would succeed in getting Sandy to allow her use of Robert. But even if Robert was successful, she could still force him to service her orally blackmailing him based on their previous encounters. Either way, Char had it wired to work out to her benefit.

His friends had been right - look at the mother; one way or another that's who you are marrying, directly or indirectly.