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

[BroRelax]

Ann: Only Time Will Tell


Yes, indeed time will tell and time will wash away alot of things..

Thank you TS for continuing with the story.

[otamay]

Originally Posted by DDAMn

I'm more interested to know wat mark future will be in that family quite interesting...

Yes me too.

Camping here for more juicy updates please.

[Shrouded]

Ann: So do you want to go for a staycation or not?

Me: Nah. Save the money.

Ann appeared disappointed.

Me: We should talk to Amanda though.

Ann: About?

Me: What she's doing? Or trying to do.

Ann: You're going to talk to her?

Me: Erm. You're her mother.

Ann: And you're the naked guy walking around my house.

Me: That's not fair.

Ann: I guess I sort of deserve this.

Me: What do you mean?

Ann: I couldn't control myself. Maybe I hurt her somehow when I fucked her guy.

Me: Was he good?

Ann: Is that all you can think of?

Me: I'm curious.

Ann: What's there to be curious about? She probably inherited some of my flaws?

Me: Like promiscuity?

Ann: You ass.

Me: I don't judge.

Ann: But that incident really brought us closer.

Me: Ok. I'm really curious now. Did you both sleep with him at the same time? Like a threesome.

Ann: What?? Of course not. I had him after she had him. Then that was it.

Me: It was really a one night thing for both of you?

Ann: Well, like I said he kept coming back for more but I wasn't drunk.

Me: And Amanda?

Ann: She rarely stuck to the same guy for more than a few weeks.

Me: So… how do you know she wasn't hurt? You know because he wanted you more than her?

Ann: I don't think it works that way.

Me: Maybe she's trying to make me want her more than you?

Ann: Again, that's not how it works. In the first place, do you even want me badly?

Under the table, she stretched her leg over and ran her foot up my calf. I nearly jumped.

Me: Hey!

Ann: I'm gonna fuck you so much you won't have anything left for anyone else.

She probably said that a little too loudly and I could feel the judging eyes of the other coffeeshop people staring at us.

Me: Well… as long as you're happy I guess I can live with that.

Ann: Haha… I'm just teasing you.

Me: Sometimes I really can't tell.

Ann: I better not catch you with any viagra or other pills.

Me: I don't think I need them.

Ann: I mean so that you can fuck my daughters as well.

Me: I really don't think they're interested in me.

But who was I kidding. Amanda was openly flirting, and Alicia wet her shorts while innocently cuddling with me in bed.

We finished our breakfast and headed back to the car.

Ann: We probably need to discuss a couple of things.

Me: Yeah.

Ann: Do you want to move in with me?

Me: What? Why?

Ann: So we can be together? Like a couple?

Me: And give your daughter more chances to take revenge?

Ann: I already said I will allow it. I deserve it anyway. But I will be jealous. You have to manage that.

Me: Let me get this straight. You want me to move into your marital home, as your lover, but if your daughter wants to sleep with me you'll let it happen but be jealous?

Ann: Something like that.

Me: That's really confusing. And it kind of bothers me a little.

Ann: Then you'll know how to react when it happens.

Me: You obviously don't want it to happen, but you're creating opportunities for it. Have you considered how I might feel about this? I already feel like sometimes you're just using me for sex. And then you'll be jealous if I sleep with your daughter but you allowed it. Can you understand the confusion I am feeling right now?

Ann: I got nothing to say. We're all adults here. Whatever happens is between consenting adults.

Me: I just don't think it's right.

Ann: I just don't want it to happen behind my back.

Again, I thought about Alicia and what happened last night. Should I be upfront with Ann and let her know what happened? Her relationship with Alicia was already kind of strained. I didn't want it to get worse. Then I realized something. Maybe Alicia was also doing this as some sort of elaborate revenge on her mother. The more I thought about it, the weirder it seemed. Maybe I needed to talk to her.

Me: I won't let anything happen with Amanda behind your back. If something is going to happen, I'll make sure you know about it?

Ann: That would be good. Let's keep the communication open and honest.

Me: Sure.

Ann: Ok. So, are we officially a couple?

Me: How official do you want it to be? I think this is the most serious relationship status you have ever discussed with me.

Ann: I don't know. We'll see how things go ok?

Me: Ok. Please think about how you're going to tell your kids.

Ann: Yeah. Alan and Amanda I'm not so worried. But Alicia…

Me: I'm sure she'll come around one day.

[olala123456]

Thanks TS for the update. Cannot wait for the next juicy update.. Back to the cave now.��..

[newyorker88]

A foursome on the way? What a family. Sooner or later, all the females in the house will be screwed by TS

[soulrapper]

Damn exciting... 3some? 4 some? Updates please!

[haikim999]

Hi shrouded, is your story real and still ongoing?

This sounds very interesting and exciting...

Do you have lookalike pics for Ann, Amanda and Alicia?

I wonder if it's a coincidence that all 3 ladies have names that start with 'A'?

[diputs1269]

Originally Posted by soulrapper

Damn exciting... 3some? 4 some? Updates please!

Yes and finally no more lonesome, cheers!

[Shrouded]

We went to Parkway Parade again after breakfast. I think Ann was attempting to help me transit out from my Army life by taking me shopping.

We went to Isetan, looked at some polo tshirts and pants, both casual and formal. Some business shirts. It's like she was really expecting me to end up as a Grab driver. Perhaps it wasn't such a bad idea. I would get a car, a job to pass the time, a house to stay in. And all I needed to do was satisfy her in bed, be attentive to her needs, manage her jealousy, and perhaps, pleasure her daughter(s) with her permission. It sounded like a pretty interesting career path, and not one I envisioned at all.

After picking up some new clothes, we headed back to her place. Alan wasn't home, probably already left for school. Alicia was obviously still in school. Amanda, well, apparently she had no classes, and was simply lounging around the house watching Netflix in just a t-shirt.

We sat down next to her.

Amanda: What's up?

Ann placed a hand on her shoulder.

Ann: Look… we know what you're doing.

Amanda: What?

Ann: You keep flirting with Mark. You're upset at me for sleeping with your guy.

Amanda: Uh-huh…

Ann: You want to sleep with him so I'll somehow feel what you felt?

Amanda was quiet for awhile, then she burst out laughing.

Amanda: Hahahahaha. What?? Are you serious?

Ann: Yes. We had those talks. But I wanna know what you're thinking now.

Amanda: Hahahaha… wait wait….. this is so funny…

Ann: Well?

Amanda: Ok. Look mom, I think you like this guy. I think you believe you can have happiness with him. And yes, I was fucking pissed with you back then and maybe I wanted to teach you a lesson. But hey, I'm glad I got your genes. I can have my pick of any guy I want.

Ann: And?

Amanda: I want you to be happy mom. But to sleep with him just to prove a point? Not my style.

Ann appeared deep in thought.

Amanda: I admit I was flirting with him. But I'm testing him. I guess.

Ann: Really?

Amanda: Yeah. Let's put it this way. The guy you slept with, my guy, do you seriously think Mark can compare?

Me: Ouch.

Amanda: I mean, you're ok looks wise. But that guy. Wow. A good 7 inches. Lasts long. Fucked so hard I thought he tore something. Pure sexual pleasure. And what I saw last night, I highly doubt you're anywhere near that size, even when aroused.

Ann: You got a point.

One thing for sure, was that Amanda had the same sharp tongue as her mother.

Amanda: Don't worry mom, you have nothing to worry about. Not from me anyway.

She turned to me and slowly lifted her t-shirt, revealing the bottom of her toned thighs. I just watched.

Ann: What are you doing???

Amanda: Teasing? Testing?

The t-shirt went higher. She wasn't wearing anything below. I finally caught sight of her waxed clam.

Ann: Hello??

Amanda: Hold on mom.

She lifted the t-shirt over her head, her firm b-cups literally waving at me.

Amanda: Like what you see?

Ann turned to me.

Ann: Do you?

Me: Err..

Side by side, Ann and Amanda probably could pass off as sisters. Ann being the much older sister of course. Body wise, they were super toned, the effect of too much gym and cardio I guess. Both of them were b-cups, and their regular exercise ensured that their breasts weren't sagging, but instead sat nicely on their chests. Amanda's nipples were lighter coloured though, I recalled reading somewhere that older women's nipples got darker due to breastfeeding, but I couldn't be sure.

Ann: Well?

Me: Good genes.

Amanda: Want to touch me?

Me: No.

I was looking for a way out of this, hoping somehow my phone will ring and there would be something important I needed to attend to. It didn't happen.

Ann came up to me and grabbed my crotch.

Me: Hey!

Ann: Ok. You can get dressed. He's not hard.

Amanda: So it's still small and cute?

Ann: Haha! yes.

Me: Very funny.

Amanda put on her t-shirt.

Amanda: See mom, I don't think you have anything to worry about.

Ann: Not from you. Maybe I overworked him last night so there's no reaction now.

Me: Wait. That was a test???

Ann: Yeah. We sort of discussed this last night.

Me: Hilarious. You two are crazy.

Amanda: Wait mom. We need to really test him.

Me: Seriously???

She took off her t-shirt again. Ann unbuckled me and pulled down my berms and boxers.

Amanda stood up and stood right in front of me. She pushed me back onto the sofa and straddled me.

Ann: Hey! We didn't agree on this!

Amanda: Chill mom, he's still soft.

She was right. At this crucial time, my dick decided to behave and stayed asleep. Amanda's breasts were mere inches from my face, tempting me to reach out and touch them, caress them, suck on them.

Ann: Well?

Me: Well what?

Ann: What are you going to do?

Me: Nothing?

Ann: Aren't you going to push her off? Or are you going to sit there and do nothing?

Me: I will give her a stern warning?

Ann: Very funny.

Me: What do you want me to do then?

Ann: What do you want to do?

Me: I think I want to see a psychiatrist. Or maybe the two of you need to see one.

Amanda: Haha! Mom he's not very fun. And he's still soft. You sure he was actually fucking you?

Ann: Maybe you're not as appealing as you think you are.

Amanda: Maybe he likes ancient pussies.

Ann: Maybe we should stop testing him.

Me: Maybe you two are right.

Amanda reluctantly got off and put on her t-shirt again.

Amanda: Well that was fun. Now I know I should avoid guys 35 and above. Seems like some of them have erectile dysfunction.

I didn't say anything but pulled up my boxers and berms and headed back to the guest room.

Ann followed me in and hugged me from the back.

Me: What?

Ann: Nothing.

She pushed me onto the bed.

Me: I'm not in the mood.

Ann: I am.

Me: How? Why?

Ann: I'm surprised you had no physical reaction to Amanda.

Me: I don't like the way you're testing me.

Ann: Are you angry?

Me: No… but you really just make me feel used.

Ann: Why didn't you stop her? Or me?

Me: I don't know.

Ann: Maybe you secretly enjoy it?

Me: What?

She pulled off my berms and boxers again and immediately went down on my flaccid dick.

Slowly but surely, her swirling tongue and light suction brought the blood flowing back there.

Ann: See! It's working fine.

Me: How far were you going to go with that test?

Ann: I don't know.

She wanked me slowly, occasionally licking the head. I was already at full hardness.

Me: Did you really need to test me this way?

Ann: I wanted to know. And I wanted to know if I could control my feelings as well if something did happen.

Me: Your feelings? Or your jealousy?

Ann: Mainly jealousy. I don't know if I'll feel hurt or anything.

Me: Do you really need to know?

Ann thought about it for awhile.

Ann: AMANDA!

I heard the footsteps and the door opening.

Me: What the fuck!

Amanda: Yes mom? Woah!

Her eyes went wide as she saw the hard stick between my legs.

Ann: You still want to test him?

Me: Hey!

I swear Amanda was licking her lips, like some hungry wolf about to devour a prey.

Amanda: 10 seconds. I'll be right back. Need to get something.

She quickly left the room.

I wondered what could be so important that she needed to get it. Maybe condoms. Or lube. I doubt she was wet. Ann kept me hard by wanking and blowing me.

Me: Don't do this.

Ann: I want to know. Really.

Me: I'm not your toy.

Ann: But you're not stopping me.

She was right. I wasn't stopping her. Maybe I wanted to teach her a lesson as well. 10 seconds were long over and Amanda had not yet returned. What in the world was she looking for?

[newyorker88]

A threesome w some sex toys!!!

[Shrouded]

Amanda came back a couple of minutes later and re-entered the room just as Ann was in the midst of blowing me. She stopped.

Amanda: Don't stop! I wanna see how you do it.

Ann: Why?

Amanda: see if I need to improve? Maybe you do it better than me?

Me: Every guy is different you know.

Amanda: are you daring me to blow you?

Me: No. Just stating a fact.

She came over to the bed brandishing a ruler.

Amanda: Move mom.

Ann stopped blowing me and moved aside. Amanda knelt in front of me.

Me: What the fuck.

She grabbed me by the base of my dick and placed the ruler there. It was a normal short stationery plastic ruler, the 15cm kind.

Amanda: Oh. Ok. You're a grower. But still smaller than the other guy.

She fondled my balls, as though she was examining me. And I thought that Alicia was the one studying to be a doctor.

Amanda: Nicely shaven. Ok thickness. Nice and veiny.

Ann: Since when did you become a sex therapist.

She wanked me, the same way her mother did, slowly, bringing the foreskin back up over the the head, before bringing it back down.

Amanda: Nice and clean. Quite hard.

She let me go.

Amanda: But he couldn't get hard for me just now. Why? Most guys just need to see some boobs, or be touched lightly and then they're rock hard and ready to go.

Ann: Maybe he only has feelings for me? Maybe he thinks the emotional part is more important?

Amanda knelt down between my legs again.

Amanda: Let me try something.

Positioning her head above my rod, she dribbled her saliva onto it, rubbing it around the head and down the shaft, while wanking me again. She blew lightly on the head and down the shaft. I twitched slightly.

Ann: I don't think that's why it's called a blowjob.

Using all the willpower I had, I focused my thoughts on other random things. Sure enough, my dick deflated.

Amanda: Ok. He's really good at this. He just made himself soft while I'm touching him.

I turned to Ann.

Me: Well?

Ann: Well what?

Me: Are you jealous? Hurt?

Ann: She's barely doing anything. I bet you get touched like this when you got for dirty massages anyway.

Me: I don't go anymore. And besides, they do a lot more.

Amanda wanked me faster, but I was too soft.

Amanda: I don't think he wants me to make you jealous mom.

Ann: You're right.

Amanda: Maybe he needs more motivation.

Ann: Like what?

Amanda took off her t-shirt again, and was fully nude in front of me. She leaned forward and wrapped her breasts around my soft dick. Part of me wanted to laugh. Her b-cups weren't small, but I was pretty sure I wasn't big or long enough for her to successfully fuck me with her boobs. Alicia on the other hand… now those boobs would have been perfect. But I was deviating from whatever was happening at that moment.

Ann: Oh. I never tried that.

Nothing happened. I stayed soft. My willpower was winning this battle, hopefully passing the test, and maybe easing Ann's fears that I would eventually prefer her daughter(s) over her. Assuming that fear was actually real and they weren't just toying with me.

Amanda: He's really good. I'm kind of impressed.

She got up, her cleavage showing the remnants of her saliva and possibly my precum.

Ann ran her finger along my shaft, ending at the head, she brushed against it. It twitched.

Amanda: He responds to you. Can tell he's really controlling himself.

Amanda cradled my balls again. Ann wrapped her lips around my head. I got hard. She released me and Amanda grabbed the shaft again, wanking me.

This time, somehow I could not will my erection away. Amanda added more saliva to the head and she played with it.

Amanda: Ah. He's staying hard.

Me: What do you expect? The two of you are just playing with me.

I tried to be angry, but I think secretly every guy wants this.

Ann removed her clothes as well. Now both mother and daughter were in front of me, naked, and playing with my hard dick. Somehow I wondered why Amanda wasn't blowing me. Perhaps it was some sort of respect to her mother.

Ann: So what do we do now?

Amanda: I don't know mom. He's really a strange one.

Me: Are you done yet?

Amanda: Mom, shall we take this all the way?

Ann didn't say anything but looked at me instead.

Me: Can we not?

Amanda: You sure you don't want this?

She got up and climbed onto the bed, straddling me with my dick mere inches from her pussy. With her free hand, she inserted her fingers into it and removed them.

Amanda: Look, I'm wet from just playing with your dick.

Ann wasn't stopping Amanda. I tried to read her face to see what emotions she was experiencing but her poker face was on point.

She lowered herself slightly, I was one inch or so away from the entrance. Her balance was immaculate. The mattress was rather springy yet she could hold that squatting position without losing her balance. I was rather tempted to just grab her hips and impale her on my throbbing cock. Fuck her hard, the way she said she liked. But this was a test. A very fucked up test. And perhaps it would be wise to just let them use me whatever way they pleased. I was horny as hell though, thanks to their constant teasing.

I didn't move. Amanda moved forward and knelt in front of my face. Her pussy, coated with juices was now inches from my mouth. She looked at me.

Amanda: You good at eating pussy?

Me: Ask your mom.

Amanda looked over. Ann rolled her eyes.

Ann: He's ok I guess.

Amanda obviously smelt different from her mom. There was this clean scent. Probably from her feminine wash. She likely went to wash up while she was getting the ruler to measure my dick.

Amanda: I'm going to sit on your face.

Me: I'm not going to eat you.

Amanda: Really?

She moved closer, her awesome balance coming into play as usual. The scent was truly alluring. Ordinarily, I might have just taken her there and then. But her mom was watching, and I was a good soldier. I follow the instructions of the superior officer. And the superior officer was silent.

After what seemed like ages, Amanda finally got off me. She bent over and kissed my cheek.

Amanda: You're a weird one. But I kind of like you.

Me: Err thanks?

Ann: So… you're not going to do anything?

Me: No.

Amanda: I would love to, if you don't mind. But it's obvious he's not willing.

Ann: Ok.

Amanda turned to me.

Amanda: If mom is ok with it, can we? I'm really really interested to find out why you're different.

Me: Er…

Ann was smiling.

Ann: Now I know where his heart is. I don't mind.

Amanda: If he's really that good, I will continue you know.

Ann: I'll consider it.

Me: You both need to see a shrink. Right now.

Ann: It's just a physical thing. Right?

Amanda: Of course.

I was rendered speechless by the brazen openness of these two.

Amanda: Well have fun. I shall not tease him. For now.

Amanda got dressed and left the room.

Ann got on top of me and slid it in. I was still relatively hard. I wondered why she was so wet. Was she turned on by Amanda teasing me?

I pushed her off and flipped over, pinning her to the bed.

Me: You're both crazy.

Ann: Maybe.

I plunged in hard, going as deep as I physically could.

Ann moaned loudly.

Ann: YES! FUCK ME HARD!

I kissed her forcefully, she kissed me back and dug her nails into my back.

Her loud moans filled the entire room. I was sure Amanda could hear and was possibly listening. I stopped.

Ann: DON'T STOP!

I started again, but went slowly, letting her feel every inch of my dick as it went in and out of her wet pussy. Somehow my mind wandered off and I started thinking about how tight Amanda was. She was definitely wet, as she had shown me. But was she tight? I was getting pretty aroused thinking about Amanda even though I was inside her mother.

Ann suddenly grabbed my hand and placed it on her throat.

Ann: Choke me.

Me: What?

Ann: Gently.

Me: Huh?

I squeezed lightly. She moaned louder, to the point of almost screaming. I was almost at the point of no return. The increased pace was making want to empty my balls.

In the midst of it all, we both never noticed the door open slightly.

Me: I'm gonna cum.

Ann: Inside.

I came, spewing my seed inside her, then collapsing onto her. We kissed, then noticed Amanda standing there.

Amanda: Wow. He's got erectile dysfunction and ejaculates prematurely too.

I pulled out, my thick creamy sperm spilling out of Ann.

Ann: How long have you been watching?

Amanda: Long enough. I like the way he fucks hard. Then slows it down to torture you.

Ann: Impressive right.

Amanda: But mom, cumming inside?? Are you making another sibling for us?

Ann: He can cum anywhere he likes.

Amanda: I won't let any guy cum in me. No way. Even though I'm on the pill.

Me: Err…. Are you just going to stand there?

Amanda: Why not? I wanna see if you're going for round 2.

As if on cue, Ann scrambled up and went to work on my dick again. It was as though she was showing off. Or showing me off. Amanda dragged the chair from the study table closer to the bed and sat down.

Me: Somebody kill me please.

I took the pillow and placed it on my face. Whatever was going on now, I really didn't want to know. But again, I didn't stop her and just let it happen.

[JAXXX]

I see a recurring theme here.... The women in this story belittle the TS' manhood at any chance they get.

[Shrouded]

Originally Posted by JAXXX

I see a recurring theme here.... The women in this story belittle the TS' manhood at any chance they get.

Yes. You are right. Haha.

[cutecuteboy]

Foursome please.. just no Alan.

[ozymandias]

Originally Posted by Shrouded

Yes. You are right. Haha.

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.