Diane Milking Sean Ch. 03

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Nis 24, 2023 // By:analsex // No Comment

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“Priapism is a potentially painful medical condition, in which the erect penis or clitoris does not return to its flaccid state, despite the absence of both physical and psychological stimulation, within four hours.”

Setting the rules: Sean

A few months into the marriage I went to visit my daughter Samantha and her new husband, Sean. All was going very well in their marriage but a mother-in-law always needs to stop by and get a first-hand impression. They loved each other, both were quite successful, and of course, they spent a great deal of time together enjoying common interests.

One evening after dinner — and here it’s my fault — a little too much red wine Sean approached me as we were doing the dishes in the kitchen. With that silly smile of a male who’s had a bit too much to drink and not enough sex that day, he asked, “So, Diane. Any chance of another massage anytime soon?”

I spun around, looked at my son-in-law square in the eyes, and slapped his face as hard as I could. Standing a good two inches taller than his six feet, I glared into his eyes and told him in no uncertain terms, “You are a married man now. If I ever want to do it, I will order you. Otherwise, keep your thoughts to yourself and your prick for my daughter. Is that clear?”

Reproached males have a dejected look, but Sean’s was that of sheer terror. He rushed out of the kitchen and ran into their bedroom. Samantha looked quizzical and then apologized for her husband, “Sean’s had a bit too much wine and he needs to get up early tomorrow to fly on a business trip.”

All night I felt terrible about the whole scene. Yes, maybe I had been to harsh on Sean, but then again a mother-in-law must set the rules of sexuality in the house. On the other hand, milking Sean’s prostate had been a first for me, and having a man lose his anal virginity in my hands had been a momentous experience for me. It was almost dawn when I made up my mind: I was going to “make nice” with my son-in-law. Tiptoeing out of my room I went downstairs where Sean had left his suitcase by the door. Like a thief in the night, I opened it and right on top I placed the panties I had been wearing. Just like that: smack on top, still smelly from me. And with that, I went to sleep feeling a lot happier.

Sean came back two nights later. Apparently his trip had been excellent and the deal he closed was enormous. Samantha and I were happy and we shared a nice meal together. After dinner I went for a walk with their huge dog. When I came back and went to my room to change for the night, I saw that Sean had already been there. Under my nightgown he had placed the panties I had given him. Only now they had been hand-washed in a scented soap. There was a little piece of paper with a simple line, “Thank you.”

I knew one of the reasons for his success was his secret cross-dressing in my panties

I knew we had made peace.

I knew he wanted me.

I knew I wanted him.

And I knew I had set the rule: it would be on my terms only.

I flew back home the following afternoon. There was a lot to plan and it had to be done so carefully now!

Setting the rules: Lisa

Lisa had been dating my son while they were in college. Things cooled off a bit when he went on some super secret armed forces special unit who knows where. She remained loyal to him and now that he was back, they got married a few weeks after Samantha and Sean.

The thing with Lisa is that she is ultra-shy and incredibly insecure. If my husband is to have a happy marriage and a successful life, I really need to get Lisa to wake up. Lisa is petite, standing at 5ft 2in, weighing a mere 110lb. She has small 32B breasts, and long blond highlighted hair. She is very fit, having been a gymnast for many years while in college here in Tennessee, and still keeping physically very active.

A few weeks after my visit to Samantha and Sean, I flew off to spend a week with Johnny and Lisa. All seemed very harmonious with them. But there was something I saw in Lisa, something I had not detected before. It was a change in her expression. She looked different. She acted different. There was no other way I could describe it when I called my husband to report. Lisa was a cute little nymph!

She avoided all talk about sex with me, blushing and running off to do something or other around the house. With Johnny it was next to impossible to get any information of any kind. But I knew like only a mother-in-law can know that Lisa’s sex life was a bit different than I would have guessed when they first met. And I was determined to find out.

It happened by sheer accident. One morning while they were both at work and my laptop battery died I ventured into the study and picked up her laptop. The history bar showed that the cute little nymph Lisa had been spending hours, days, and weeks reading erotica!

That was all I needed. That afternoon when Lisa came home, I confronted her. She started to cry and said Johnny seemed to have çankırı seks hikayeleri lost sexual interest in her. And just now her own desires were starting to awaken. Sob, sob, sob.

My arousal was getting more intense with every sob of hers. I held her close to me, a lot closer than a mother-in-law normally would, and told her that I was going to let her into the secrets women in our family passed on from generation to generation to keep our husbands interested, in line, and at home.

But she would have to do what I said.

She balked. All I had to do was to look down twelve inches, stare into her eyes, and whisper, “I set the rules in this family.”

She understood exactly what I meant.

Good. Now I had both Sean and Lisa all to myself!

Sean and Lisa look at each other

The entire family came over to our house for a three-day weekend. My husband offered to take the two siblings, Johnny and Samantha, to visit his aging mother. Asking if we all wanted to go, I nicely pointed out that Sean and Lisa really had nothing to do with Nanna, and besides, too many people would confuse the old lady. My husband agreed. Saturday morning the three of them drove off for the day to see her.

No sooner had they closed the door behind them and driven off, that I turned to Sean and Lisa, standing next to me in the foyer. “Take off your clothes. Now.” I told Sean in a calm, cool voice.

“Here, Mommy Diane?” he asked.

My icy stare was enough for him to understand that yes, it was here. And now.

He obeyed. His tall, slim body was a beauty to behold! The three, deep scars on his back gave him an added look of strength. I motioned him to turn around this way and that and he complied. His seven-inch uncut cock throbbing nicely in thin air made him look even more handsome than I remembered.

Lisa too was staring. I turned to her very sweetly, “Sean is quite nice, don’t you think?”

Lisa stammered, “It’s just that I’ve never seen another man except Johnny.”

I really was not expecting this at all! Lisa had only been with Johnny! No wonder she needed a lot of coaching and training and practice if she was going to have a happy marriage!

Just as sweetly I asked her, “You too take off your clothes, Lisa.”

She stammered again, “It’s that… it’s that… it’s that… Mommy Diane, it’s that…”

I was losing it with her, “Lisa, it’s that WHAT?”

“Mommy Diane, it’s that Johnny is the only person that’s even seen me without clothes.”

“Listen and listen carefully, Lisa. Either you take off ALL your clothes NOW, or else it’s going to be a lot more people other than Sean and I that are going to see you stark naked today. Like all the bikers at the bar downtown.”

Lisa turned away from us. Trembling and quivering, she took of her blouse. Ever so meticulous, she folded it nicely and placed it on the floor very neatly. She wiggled out of her jeans. Same neatness in folding and putting down. Cotton panties with Snoopy on them. Cute but let’s grow up, I was thinking to myself. Still with her back to us, her trembling hands were fumbling nervously with her bra snaps. And when she finally managed to get it un-snapped she seemed unsure what to do with it. I was losing my patience. Sean seemed frozen in time and space staring at her lily-white, petite body.

She looked over her shoulder to me. I nodded. She and I knew what the question was. Her entire body was shaking like a leaf. Her legs were wobbly. She acted as if she had never taken off her panties before, first one trembling leg, then the other, a bit too careful not to lean over, doing everything possible to delay the inevitable.


“Turn around, Lisa.”

Her right arm covered her meager breasts. Her left hand covered her pube. She turned slowly, eyes wide open like a fawn’s at dawn.

Sean was staring at her like the idiot males always are at this moment in time. I walked over to Lisa, stood behind her, and slapped her ass with an open palm, slapped her as hard and as a fully as I could slap her derrière. “Hands at your side, Lisa.”

“Yes, Mommy Diane.” She had tears in her eyes. And now both Sean and Lisa knew that I meant what I said. And that any infraction of my wishes would be met with a vicious slap. Sean’s face and Lisa’s derrière had been the first for each. The first of many more to come and they both knew it.

I let them both stand face to face, both with their hands at their sides, each looking and staring at the other. Sean’s eyes raced up and down Lisa’s petite figure, taking in her soft skin, her slender neck, her small breasts, her nipples darkening and perking up, her flat tummy and beyond as far as he could see. Lisa too was admiring Sean, mostly watching his cock. I could almost feel her pretty face bobbing up and down with every throb. I was giving them time and space to learn each other really well!

The anal discovery

I let them stand there while I went upstairs, fetched the bottle of baby oil, and brought it back down to put under running hot water in the kitchen. I took my time, calling Joel to make sure they were well on their way, that the road was free of snow, that they were looking forward to seeing Nanna, blah blah blah just to make sure I had the entire day to myself.

When I came out of the kitchen and asked Sean and Lisa to the living room, I had the baby oil bottle with me, wrapped in a towel to keep it warm. Sean saw it and a smile came across his face. Lisa did not see the smile: her eyes were elsewhere. All she saw was a strong throb and a droplet of golden pre-cum ooze out.

“Lisa, sit down next to me. Sean, masturbate.”

“Mommy Diane, how do you want me to…”

“Sean, don’t start on me. Pull back your foreskin. All the way. More, A bit more. Good, now hold it back with that hand. Use the other hand to pour baby oil on your cock. And let Lisa and I see you stroke it. I want to see long, slow, complete strokes, up and down, slide over, up and down, slide back, up and down.”

“Yes, Mommy Diane.”

Lisa’s eyes were popping out. I had Sean step closer and turn this way and that to give Lisa a more complete view of Sean’s masturbation. I was staring at Lisa. But she was lost in her concentration. She was squirming on the seat, crossing and uncrossing her thighs, not quite knowing what to do with her posture.

I saw that Sean’s pee hole was dilating a bit too close to the brink of a premature ejaculation. I made him stop. Turning to Lisa, I asked her point-blank, “Lisa darling, now it’s your turn. Show and tell. Do you want to show or tell?”

She panicked, “Mommy Diane, may I please tell?”

I laughed, “Of course, darling, you will tell. Later you will have to show, too. Understood?”

She nodded. Bravely she stood up and walked in front of me. I asked Sean to l sit next to me. She inhaled, swallowed deeply, and got the courage to ask, “Mommy Diane, what shall I tell?”

“Lisa darling, what’s the kinkiest, strangest thing Johnny makes you do?”

Again, she panicked. Her body was shaking and trembling. She fidgeted and fought her self-control. She was desperately buying time. She wanted the world to come to an end. She wanted to leave to another universe. Finally, she blurted it out.

“Mommy Diane, Johnny makes me wear a plaid skirt and an embroidered blouse. He says I was a naughty schoolgirl and that I have to take of my knickers. He makes me bend over the table and he spanks me with the ruler. Then he…”

She was sobbing. “Then he what, Lisa?”

“Mommy Diane, then he takes me from there.”

Sean was practically drooling pre-cum all over the place. He looked at me and I smiled back.

I had to ask her, “Lisa, Johnny fucks you up your ass while you’re dressed like a schoolgirl in a plaid skirt and embroidered blouse?”

“Yes, Mommy Diane,” her eyes lowered.

“Lisa, look at me and say it loud and clear so Sean and I can hear you.”

“Mommy Diane and Sean, Johnny f-f-f-f-f-f-fucks me up my a-a-a-a-a-a-ass.”

“That’s better, Lisa. And do you like it?’

“Yes, Mommy Diane,” her eyes lowered.

Amazing discovery!

The cute little nymph was into anal sex!

And Sean was into prostate massages!

The day was taking a totally different turn than I had planned!

What a fortuitous discovery this had been!

Breaking in and training — both Sean and Lisa

My mind was racing: there were so many interesting opportunities. With both Sean and Lisa into anal sex, I could have countless hours of endless enjoyment. But I knew I had to calm down and proceed slowly and deliberately. I had to be strategic and plan things perfectly. If all went well, this could be the first of many, many more anal sessions. I decided to go for the cute little nymph first. Ordering her to lie down in the living room floor, I told Sean to bring over two chairs. Lisa put her legs up on the chairs and Sean spread the chairs so that Lisa ended up with her knees wide apart and her legs up high.

Motioning Sean to come closer, I told Lisa so spread her labia. Sean was staring intently as she opened herself up. At first Lisa was shaking and very insecure about it. This made it all the more exciting for me.

Once she had spread her labia very far apart, as far as they would go, I ordered Lisa to unhood her clit. She was very uncertain what I meant, so I repeated it, this time in a softer, icier voice. Gently she started to pull back the protective hood. It was very uncomfortable for her, I could already see how sensitive Lisa really is. After some time and quite a bit of whining and struggling, she finally managed to pull the hood back all the way.

Leaning over to get a closer look, I was surprised to see that for such a petite woman, how fully formed and well developed her clit was! I instructed Sean never to touch a woman’s clit until she is screaming to be relieved of her repressed orgasmic agony. Woman have infinite erogenous zones: use and abuse all of them before attacking our clits.

With Lisa thus spread apart on the floor, I told Sean to kneel next to her pretty face. While Lisa stared in amazement, I told Sean to pull back his foreskin all the way. This time I told Lisa to hold off touching the glans until the very end — if at all. Men will do anything in the world just to have that last inch touch. Leave it alone until you got what you wanted — anything you wanted!

It was time to get started. Lisa was wetting profusely; Sean was dripping incessantly. I took them upstairs to my bedroom. Again I started with Lisa. Ordering the cute little nymph to kneel by the bed and place her torso on the bed, head on a pillow, I made her spread her knees wide apart. Telling Sean to pour warm baby oil on her ass, I taught him how to tease and taunt a woman’s derrière. Warm baby oil dripping down her crack, Lisa moaned and purred. Granted, Johnny fucked her ass regularly so she was not the anal virgin I would have preferred — but today she would learn interesting variations.

Sean looked at me and I nodded. His finger pressed against her ass. Lisa was moaning. Quite simply, I told Sean to push it in. All the way in. No teasing, no foreplay, no preparation. Just go in.

And I taught him a lesson he will use the rest of his life. Just as he is about to thrust into her ass, slap her derrière. Just once. Really hard. Invariably, the woman will be caught so totally off-guard she will have no control over her sphincter and will open right up. Sean smiled and continued to caress and tease her lovely derrière. When neither Lisa nor I were expecting it, Sean slapped her derrière and his finger went all the way in!

The look of surprise on Lisa’s face was priceless!

I taught Sean how to slide his finger all the way into her ass and almost all the way out. Never go all the way out. Women have very sensitive nerve endings around our anal areas and can feel everything. Leaving even just the tip of his finger in her ass keeps those raw nerves stimulated.

Lisa was moaning and purring like a kitten. She was trying to move her hips to one side or to the other. Sean quickly learned to have his finger follow her hips as they swayed from side to side. Let Lisa feel that no matter where she goes, his finger remains up her ass! Lisa tried to move her ass back, seeking deeper penetration. Again, Sean learned from me to keep his finger as deep or shallow as it was and just follow her ass. He has to set the depth of penetration, not she!

More baby oil, lots of it actually, and Sean learned how to use TWO fingers up her ass. It’s not just a question of more-is-better but a question of TWO fingers moving independently up her ass, giving Lisa totally new and unexplained sensations. Open the finger wide apart inside, move them side to side, feel her anal muscles struggle and tense up and relax.

Sean asked me, “Mommy Diane, should I touch her clit?”

I laughed. That’s all men think of! Here was Lisa moaning and purring like a kitten, ready to go on for hours with such intense stimulation: make her ride the wave!

But as a woman I could sense that soon Lisa might lose interest. Gently and patiently I taught Sean how to use his other hand. Again, extremely careful to avoid her clit, I showed him how to slip two fingers into her pussy and touch those up her ass. Sean seemed to struggle with this. I tried it.

Lisa’s pussy was even tighter than her ass! I had never seen a woman like that before, with a pussy far tighter than her ass. Must be all the gymnastics she did.

I asked her if she did her Kegel exercises on a regular basis. In the midst of her anal purring her moaned, “Yes, Mommy Diane, every morning and every night.”

So there it was! The cute little nymph that so much enjoyed anal sex had a pussy so muscular and so tight she could actually control a man! More about this would come later!

I taught Sean how — still keeping TWO fingers highly active and deep up her ass — how to reach into her pussy… there were two things I wanted him to find: the tiny urethral duct and her G-spot… all men think that fingering a woman deep up my pussy feels good… well, Sean learned right then and there just how sensitive the first two or three inches are… after that, we really cannot feel much difference…

By keeping his pressure on her tiny duct, he could keep her from bursting… but it had to be done just perfectly… and Sean was learning just by learning from me how to “read” Lisa’s body language as she moaned and squirmed and gasped…

And Sean also learned right then how and where to find Lisa’s G-spot… after that, it was almost straight downhill! He learned from me how to use his two fingertips to gently press down on that spongy mass of tissue… press and release, press and release, press and release…

Lisa had lost complete control. She had lost her dignity. She was desperate. Amid the throes of her passion, I softly whispered in her ear, “Lisa, you are an anal whore. You are an anal slut. You are an anal bitch. Say it. Load”

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