An Affair with an older married lady... and the aftermath...

[Shrouded]

Originally Posted by ozymandias

Dear Shrouded.

Thank you for your candour and sharing. In a sense you are right they should both well both Alpha females see a psychiatrist but as they have not put themselves under the chair I will endeavour to do my best. These will be at best a guesstimate so as always take it with a pinch of salt. Based on the details you have shared and you have put forth.

1. Ann is a Catholic , probably a convent girl and from her expressed sexuality , probably IJ or KC and based on driven personality and corporate personality , top class , top girl , in those respective schools and if not IJ or KC then St Nicks.

2. She married her husband because of an accident and because it was the right thing and possibly because he was more comfortable family wise and offered a chance at a better life. She and her could be of equal SES or social economic status when they got married and if so the analysis will shift but I will leave it at that.

3. Husband probably grew up in the East. Highly likely SJI or St Pats , and likely the family was in the Car Business or in the Car Dealership Business. Beating up the BF of your wife seems more like SJI or St Pats then any other school I know off.

4. The marriage was one of convenience but she hoped to fall in love after, The kids following were an attempt to build a family and then love. That attempt failed and hence her loneliness which she pushed into work and family but not her marriage.

5. Lovers were many but love not there. You offered a discreet safe relationship away from her industry and social circle. Its one thing to have an affair within her SES , its another to flaunt it. She has separated or with her daughter separated sex and emotion and in this modern day and age its common which is why for some reason with you sex came with emotions which she could feel again,

6. I do not think she expected to fall in love with you and as to why you , well perhaps sincerity and because with your normal sincere heartland roots you reminded her of what she had or what she left behind.

7. She married for money perhaps and thus in a way is using money to buy love, accepting gifts to willingly degrades that love which she needs and wants from you.


8. Money is not love and sex is not love , she is not willing to let you go but wants to make sure that she has you not because of money and not because of sex.

Wow. This is a very in-depth analysis.

1. I don't think she's Catholic. Didn't see any crucifixes or altars in the house. She and her kids don't go to church either. Not sure if she's an IJ girl, never really asked. Nor if she was in a top class, top student etc.

2. Not sure about this. She did say it wasn't an accident. I never asked about her SES either but it seems like she's more than capable of attaining a higher status regardless of whether or not her ex husband is of a high status.

3. Totally no clue on this. But yes, St Pat's and Katong Convent are relatively near to where she lives. I never really probed into her past life.

4. Don't think it was for convenience, but she did say there was no love and she thought kids might help there.

5. Yeah. Many lovers. Sort of. But this analysis is exactly what I was looking for and trying to comprehend. The separation of love and sex.

6. You know, up till this day, I don't really know if she loves me or not. I'm clueless at that aspect.

7. I'm not so sure about the reasons for this either. Maybe you're right. She has lots of money and isn't afraid to use spend it. Whether on herself or her kids or even me. But whether she is buying love, I really dont know.

8. Don't know about this either. But I think I wasn't sticking around because of money, sex or maybe even love. It was more of a sense of comfort and belonging I guess?

But you know what will be interesting? Maybe you could do an analysis on me as well. Haha...

[Shrouded]

If I was supposed to be their underwhelmingly average sex toy, I was doing a pretty good job of it.

I left the pillow on my face, half wishing somebody would put me out of my misery. Except I wasn't miserable. Maybe I could get used to having an audience.

After blowing me till I was hard again, Ann started riding. At least I assumed it was Ann. At that point of time, I really couldn't care less. She could use me however she pleased as long as it made her happy. Amanda sitting there watching her didn't seem to affect her much as I felt her ride and grind herself to orgasm.

I tilted my head to the side, still under the pillow, facing where Amanda was to try to catch a glimpse of what she was doing. Then I realized the chair was empty. Wild thoughts ran through my mind. Perhaps it was Amanda who was riding me? But it couldn't be the case as I never felt Ann get off me.

Then I felt it. She sat on the bed. I was tempted to remove the pillow to see what was happening. I felt a hand running up my body and ended up at my nipple. It was most definitely Amanda's. Highly unlikely that Ann's hand was that long.

The pillow flew off. A naked Amanda was staring at me.

Amanda: Hi!

Me: Thank god.

Amanda: What?

Me: It's still your mom riding me.

Amanda: Oh. You wanted me to do it?

Me: Er…

Amanda: It would satisfy me… marginally.

Me: Right.

Ann was lost in her own orgasmic world.

Amanda: You know what a cock sleeve is?

Me: Not really..

Amanda: Can add a couple of inches.

Me: I don't need one. Your mom is satisfied.

Amanda: But I won't be.

Me: I'm not fucking you.

Amanda: For now.

Me: Right.

She lay down next to me with her phone. I saw she was browsing through Aliexpress. She showed me a couple of sex toys.

Amanda: Think this penis pump will work on you?

Me: Funny.

Amanda: Ah here's the cock sleeve. If I get one will you try it out?

Me: With you?

Amanda: Yes.

Me: No.

Amanda: You're no fun.

Suddenly, she cuddled up next to me and struck the pose with the "v" sign took a selfie. Her naked upper body was pretty obvious in the picture.

Me: Hey!

Ann: What are you doing now?

Me: Delete it please.

Amanda: I'm not posting it on social media.

Ann: Delete it.

Amanda: Fine.

She deleted it and put her phone aside.

Suddenly, she climbed onto me and sat on my stomach.

Me: What now.

She brought her chest closer and closer to my face. I did nothing.

Amanda sighed.

Amanda: Guess you're not a boobs person.

She turned around, thrusting her butt near my face. I caught a whiff of the familiar scent.

Amanda: Maybe you're a butt person?

Ann: Stop teasing him.

Amanda: But you're having all the fun!

Ann: And he said he won't fuck you.

Amanda: Fine.

She inched closer and closer.

I don't know what possessed me but I grabbed her waist and pushed her off slightly. Luckily, her great sense of balance was still there, otherwise she might have collided with her mom mid-ride, and possibly snap my dick off.

I spanked her ass lightly, she purposely let out a seductive moan. It was the first time I intentionally touched her. She got off the bed with an evil grin on her face.

Amanda: I think he's into BDSM.

Me: What? I'm not!

Ann: I never really experienced it with him.

Amanda: He just spanked me!

Me: Lightly?

Amanda: So you can spank me, but you won't touch me anywhere else?

Me: Er..

She grabbed my hand and placed it on her chest. I retracted it immediately.

Amanda: Weirdo. I'll probably have more fun with my toys.

Me: If I never met your mom, you might have a chance with me.

Amanda: Wow. Somebody's suddenly very confident.

Ann: Unfortunately, the chances of you meeting him are slim to none.

Amanda: Yes mom. And the chances of you fucking my guy was also slim to none. Only difference was that guy couldn't keep it in his pants.

Ann got off.

Ann: You wanna fuck him? Go ahead.

I took the opportunity to cover my dick. And hoped it would go down immediately.

But somehow having two ladies fight over me was kind of a confidence booster.

Amanda: Don't think I won't! But he's covered in your juices. Where's the wet tissue?

Ann: No way. He's mine. You can just watch.

Ann pulled my hands off and mounted me again. Amanda pretended to sulk. But somehow I could tell she was secretly enjoying herself. Probably biding her time until she got me alone.

I didn't know how much more of this I could take. Physically I was fine, but I was sure this would definitely affect my mental health.

But again, I could have stopped all of this yet I didn't. Maybe it was something I really wanted to do just to make Ann happy. Assuming it was something that really made her happy.

And all this while the wise words of Bro EoS was playing at the back of my mind. I was definitely seizing the day. Or in this instance rather, the day was seizing me.

[minelover]

Wish you'd fuck Ann hard and make her scream haha

[DDAMn]

Well bro...wat a headache sitrep ur were in.

[xAhKingx]

your constant updates is greatly appreciated.

[ozymandias]

Originally Posted by Shrouded

Wow. This is a very in-depth analysis.

1. I don't think she's Catholic. Didn't see any crucifixes or altars in the house. She and her kids don't go to church either. Not sure if she's an IJ girl, never really asked. Nor if she was in a top class, top student etc.

2. Not sure about this. She did say it wasn't an accident. I never asked about her SES either but it seems like she's more than capable of attaining a higher status regardless of whether or not her ex husband is of a high status.

3. Totally no clue on this. But yes, St Pat's and Katong Convent are relatively near to where she lives. I never really probed into her past life.

4. Don't think it was for convenience, but she did say there was no love and she thought kids might help there.

5. Yeah. Many lovers. Sort of. But this analysis is exactly what I was looking for and trying to comprehend. The separation of love and sex.

6. You know, up till this day, I don't really know if she loves me or not. I'm clueless at that aspect.

7. I'm not so sure about the reasons for this either. Maybe you're right. She has lots of money and isn't afraid to use spend it. Whether on herself or her kids or even me. But whether she is buying love, I really dont know.

8. Don't know about this either. But I think I wasn't sticking around because of money, sex or maybe even love. It was more of a sense of comfort and belonging I guess?

But you know what will be interesting? Maybe you could do an analysis on me as well. Haha...

Just Pmed you.

[BroRelax]

Thank you TS for the constant update.
read until so steam...

[otamay]

Originally Posted by DDAMn

Well bro...wat a headache sitrep ur were in.

Yes, Mark is in a real fix and fuckup position which can be fuck by Amanda any moment.

Camping here for more juicy updates please.

[Shrouded]

I gotta admit. It's fucking weird having a woman's daughter in the same room when you're fucking her. Or being fucked by her. And the daughter is naked as well.

By the time Ann was done using me, and Amanda was done teasing me, it was way past lunch time.

I wasn't hungry though. All I wanted was to lie in bed and not move. Physical exertions aside, I was a soldier, I could handle it. But the mental toll was a little harder to describe.

Maybe I unwittingly entered a family of female sex demons and this was the hell I was thrown into for eternity. But if this was hell, I surely didn't mind going through it over and over again.

Ann left me in the room while she went to shower. Amanda cheekily stayed behind. I felt a little abandoned to be honest. Ann left me behind to deal with her spawn. The naked demon who was now sitting in the chair and staring at me. I was having naked conversations with Amanda.

Amanda: Wanna have a quickie while mom's away?

Me: No.

Amanda: She's not here, you don't have to pretend anymore.

Me: Pretend what?

Amanda: That you don't want to fuck me.

Me: But I don't.

Amanda: Mom's ok with it you know.

Me: That's what she says. I don't want her to regret.

Amanda: Regret?

Me: This whole situation is weird. Can I ask, honestly, how did you feel when you found out she slept with your guy?

Amanda: Well…

Me: Honestly.

Amanda: If your father fucked your girlfriend how would you feel?

Me: Hmm. I don't know. But he wasn't your boyfriend right?

Amanda: Nah. Just a fling.

Me: So how did you feel?

Amanda: At that time we all knew she was sleeping around already. Can't blame her though. She was forced to leave you. Then dad died. I think she went through quite a tough time and no one was there for her.

Me: I sense a but somewhere.

Amanda: But. I sort of liked the guy. Might have been more than a fling. After mom slept with him he didn't want me anymore. Like I was lousy in bed or what. I felt-

Me: Betrayed? Lousy?

Amanda: Something like that. But she only slept with him once. So I guess it wasn't so bad.

Me: And?

Amanda: Of course we became closer after that incident. Mom and I. She felt bad. She blamed alcohol. But I think it was her poor impulse control and decision making. I tried to understand her and give her time and space. We all tried. Maybe Alicia didn't try as hard.

Me: Did she really say you could take revenge by sleeping with one of her guys?

Amanda: Of course not! Haha… I was the one who said I'll fuck her guy so she knows how I felt. I was only half serious.

Me: And?

Amanda: You're the first she chose to bring home. She's issuing me a challenge.

Me: Really?

Amanda: Nah. I think she feels really comfortable around you and I think you feel the same way.

Me: Both of you make me uncomfortable now. How did the decision to test me come about?

Amanda: Quite randomly actually. I was asking her how come she brought you home to meet us. She never did that before. I figured you must be someone special. Or really good in bed.

Me: And?

Amanda: And so I said let's test you? If you passed then good. If you failed then maybe I got to have good sex?

Me: Right.

Amanda: She really likes you, you know?

Me: I don't know. The way she treats me sometimes…

Amanda: Like how?

Me: She uses me for sex?

Amanda: Does she really? Don't you get to enjoy too?

Me: Well I do.

Amanda: Then? Guys are supposed to be simple. Give them sex and they're happy. End of story. Why do you have to make it so complicated?

Me: You know she used to give me money after we had sex? And she wants to buy things for me?

Amanda: OMG. You're her sugar baby. Hahahahaha.

Me: Why does she need to do that?

Amanda: Who knows. Who cares? She's happy right? Why can't you be?

Me: I don't know. Not used to it.

Amanda: Get used to it. She has money. She decides how to spend it. If she wants to spend it on you just take it. If I wasn't rich, I wouldn't mind a sugar daddy as well.

Me: Right. Why does she like to, how you say, put me down sometimes? Insult me?

Amanda: You mean about your small cock? Haha.

Me: Yeah. That's one thing.

Amanda: Haha! I do it too. What's the big deal. For me it's a way to control the guy's ego, to put them in their place. It's a control thing, you can't let the guy feel like he's king all the time right? Otherwise they'll just take you for granted. Even that 7-inch guy, I told him he was small.

Me: Oh? How did he react?

Amanda: He fucked me so hard I almost forgot my own name.

Me: Really?

Amanda: No. I'm kidding. But wow, when he's fired up, I came so many times.

Me: Did you learn that from her or she learn from you?

Amanda: I don't know. It came naturally.

Me: So actually I'm not that small right.

Amanda: You're normal I guess. The guys I've been with, minimum above 6 inches. I don't take anything less. But for you I'll make an exception.

Me: Right.

Amanda: Why do you even need the validation?

She suddenly sat next to me on the bed, her hand wandering to my soft dick.

Me: Hey!

Amanda: Mom's still showering. I won't tell her.

Me: I didn't clean it. No wet tissues here.

I hoped she wouldn't go digging in my bag.

Amanda: Damn.

Me: You really want to sleep with me just to prove a point with her?

Amanda: I'm not a vengeful person. And I'm damn impressed at your self control.

Me: That's not a good enough reason.

Amanda: True. But you'll never know what may happen in this house.

Me: Yeah. I don't.

Amanda: Get up.

Me: Why?

Amanda: These sheets need to be washed.

Me: Right.

She removed the sheets. There were numerous wet patches all over.

Me: Actually I have another question.

Amanda: Shoot.

Me: Is Alan gay? Your mom may have mentioned something like that.

Amanda: Oh. Didn't know you liked guys too. You bi?

Me: No. Just wondering.

Amanda: Well… he's… undecided I guess. But I can confirm he's a virgin. Haha.

Me: You would know because?

Amanda: Ok fine..I don't know. I only know he never had a girlfriend before. He's in love with exercise and the army. He rarely goes out, even with friends. I can't even catch him masturbating or watching porn. He's like the angel in this family.

Me: I see.

Amanda: You probably can get along well with him. Considering how you can get along with me. He's just like me, only with a dick and not interested in sex.

Me: Right.

Amanda: Good luck with Alicia though. She's a mystery. Nobody can figure her out. I don't think she really hates mom, but she's really upset about many things mom did. I'd be surprised if she didn't sneak in here at night and cut off your dick.

Me: Would she do that?

Amanda: I'm kidding again. But I don't think she really likes you. Surprised she asked you to drive her to school. Maybe she's growing up.

Me: Maybe.

She gathered the sheets and put them on the table before turning around and hugging me, her naked breasts on my chest, her bald pussy rubbing against my dirty cock.

Amanda: Bloody hell. Still no reaction. You don't like young girls?

I merely smiled at her.

We didn't bother getting dressed and walked to the backyard naked where she dumped the sheets into the washing machine. They had a dryer too so I guess I could use the same sheets that night.

Ann came down shortly to see us chatting in the living room.

Ann: Did you two…

Amanda: No mom. We didn't. Really. He's got a problem with his penis. I wish you luck.

Ann: Ok. Maybe you should go wash up?

Me: Yeah. Can I use your bathroom?

Amanda: You can shower with me…

Me: You know this won't work on me right?

Amanda: Still trying my luck.

She skipped up the stairs.

Ann came to me.

Ann: Nothing happened? Really?

Me: Yeah.

Ann: Are you for real?

Me: I'm quite real.

She took me by the hand and led me up the stairs to her bathroom.

Ann: Let me clean you up.

I wondered if I had enough left in me should she want me again.

[Brunoferz]

Haha nice one

[diputs1269]

Amanda is so tempting, I can't hold reading for more. Cheers!

[Neoguri]

Bro Shrouded,
Looking forward to your posting everyday!
Exciting story!

[Jjcoolidge]

Never fails to amaze me how TS has developed this story. Support Bro Shrouded! Keep the juicy updates cumming!

[newyorker88]

Really a weird family. I really wonder if this is for real or half half. But nice story

[glozz]

Very interesting story; and I've been reading it not for the sex elements. However, since you've expressed disbelief with your situation, I've actually known very similar people/families, although I'm not aware of their sexual details. I'm assuming here though; that this story is real and not fake.

Are you familiar with Maslow's hierarchy of needs? Obviously in this case, Ann's family is well-to-do and has no "real" issues with their fulfilment of all the basic needs.
Which only leaves the ones at the top of the pyramid. Now, like it or not; people from rich background are never simple due to these factors. It is a mixture of these factors which make people "strange", "unique" or "weird".
And incidentally, it would seem that these factors are driving the situations that you are encountering.

Ann is probably the "simplest" among everyone else. It would seem that hers is just a case of neglecting herself (I agree with most of bro Ozymandias (except the specific points around being Catholic, JC, IJ, etc. I don't believe in generalizing) over the years in favor of building something lasting. When that failed, her frustration led her to start focusing on herself; the easiest being her sexual desires. This eventually led her to emotional fulfilment - you. Which is why she is staying with you. Your loyalty over the years coupled with her emotional attachment gives her the "cinderella/princess" feeling that she never had/experienced over the years and as she is now free of her obligations, she is pursuing her desire for finding/fulfilling what she has missed.
Her giving you money, wanting to secure your security; is her form of exchange. Obviously, she doesn't want to feel that she is using you; which is why she makes you feel that she is, because you feel that money is not something easy. For her, money is the easiest way to return the favor; as she could not be emotionally invested previously. It is also her way of "making up" for all the lost years.

I could probably explain the daughters' behavior later, but at this juncture; there's insufficient information for too much typing. And my information above may not be accurate.

But, to give you some ideas; the girls are young, and to them; you're a very interesting challenge and trophy; as they would like to understand what their mom sees in you. What humans can't get, they want even more. So; expect the tests to intensify, and honestly; if you want to continue in this situation, keep up your good work and focus on their mother.

For the minute you give in to temptation and fuck the daughters; the whole "arrangement" will collapse. Trust me on this. It's the same reason why ONS exists and why lust fades after sex.

In any case, this is assuming the whole story is true. If not, then this is just a random wall-of-text.