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

[SerflySGR]

Originally Posted by Neoguri

I should go back to Singapore and work in a local company!

Please don't come back, Bro Neoguri.

You come back, we no chance already. Heh heh!

[Shrouded]

I really didn't want to have to sleep with Natasha again. It wasn't because it wasn't pleasurable. I mean, come on, who doesn't enjoy sex? But I didn't want it to become a habit.

I wish Shirlyn didn't join us for cycling, then she wouldn't have gotten to know more about Darren from the girls. It wasn't that I was afraid that I would lose her to him. I knew I was still able to pleasure her the way she wanted. At least until she actually tried Darren.

But she was right, I really was too accommodating. I would just do anything and everything they wanted me to do, no matter how absurd it could be sometimes.

We awoke nearing the evening as the rain let up slightly. I thought it would be best if I left before her family came home.

I shook her awake.

Me: Hey…

S: Did he reply when he is free to meet?

Me: Is that seriously the first thing you want to ask me?

S: Well… Do you want to have sex again?

Me: Sure.

S: But when does he want to meet?

Me: I haven't checked my phone.

I pretended to check my phone. I knew Darren probably wasn't going to be free unless he literally just dumped his kids at his in-laws and went off to do his own thing after that.

S: Well?

Me: Hang on. I'm asking.

So I texted him for real.

D: After 11pm. But where? Are you meeting Nat?

Me: Yes I will.

D: Great! She's really excited!

Me: Shall we get a hotel room or something? It's not convenient to do it at your place right?

D: I only have one master bedroom.

Me: That's what I thought.

D: Unless you take the living room?

Me: Are you serious?

D: Why not?

Me: How about we get a hotel room?

D: Save the money bro. Just come over. Entertain Nat while I get to know your friend. Then we'll see how it goes. Worst case, borrow Jasmine's bed.

Me: I'd rather not.

D: Understood.

Me: I'll ask her.

I put my phone down.

Me: He's free after 11pm.

S: Great!

Me: Location?

S: Here?

Me: Isn't your family coming back?

S: Nope. I sent them on a staycation again.

Me: For real?

S: Well… I sort of planned this.

Me: Planned what?

S: Getting you into my house again.

Me: Wow. I'm speechless. Did you plan for a threesome as well?

S: Obviously not. I just wanted a weekend of sex with you.

Me: And then a big dick appears.

S: I still want a weekend of sex with you. Just that maybe he's a commercial break?

Me: What?

S: I obviously didn't know you need to pleasure his wife in order for me to meet him.

Me: And yet you still want it?

S: Why not? Commercial break for both of us. Do you want to cancel it?

Me: And deny you the big dick experience?

S: It is intriguing.

Me: You're ok with me pleasuring his wife?

S: Why not? You're not my boyfriend. I'm damn sure you're going to run away after this again. So you aren't really my fuck buddy either.

Me: And if I don't?

S: Meaning?

Me: I'll be your fuck buddy.

S: Ya right.

Me: If you really want it.

S: I've been asking you ever since that day even though I know eventually you'll want to go back to Jasmine.

Me: And?

S: You seemed so reluctant. Don't know what's wrong with you. Free sex but you don't want.

Me: It's complicated. Even you didn't know what to expect from this kind of relationships.

S: I think I've given it enough thought these few weeks. Have you?

Me: I wanted to be with Jasmine. But she's changed. Asked me to see others until her divorce is finalized. Says she won't see anyone else.

S: Kind of sus don't you think?

Me: I don't want to think anymore.

S: Good. Don't think. Just do.

Me: It's not that easy.

S: It is. Go fuck his wife. He comes over and I get to see what the fuss is all about. Then you come back and we fuck till tomorrow.

Me: I'm not superman.

S: I'll make you hard.

Me: And what if you find my dick too small to satisfy you after that?

S: Then I guess you'll need to find someone else then?

Me: You see how damaging this is?

S: To your ego?

Me: Yeah.

S: Put yourself in our shoes. You sleep with us. Then you go sleep with others. Don't you think we wonder why? Or question what we did wrong to not be able to hang on to you?

Me: Ok.

S: You appear to be so experienced in this. Fuck buddy or friends with benefits relationships. But in fact you're not. You can't handle the emotional fallout. But you hide it very well.

Me: And you can handle it?

S: I never had a fuck buddy before. I'll learn. We're all constantly learning don't you think?

Me: I guess so.

S: So yeah. Go fuck his wife and report back to me later.

Me: Report?

S: Don't you need to report things in the army?

Me: Yes?

S: I'm your commanding officer now. And I'm giving you an order. Submit your verbal report of the incident to me later.

Me: Very funny.

S: I think this is fun.

Me: Right.

S: Lick me till I cum.

Me: What?

S: That's an order.

Me: Really?

S: No I'm kidding. Let's just rest. You need to perform tonight.

Me: Honestly, she does most of it.

S: What? Then you just lie there?

Me: Sort of. We only did it once. And Jasmine sort of took over.

S: Wah. Threesome.

Me: That was goodbye sex. Sort of. I think.

S: Show her what you've got la. She will appreciate it.

Me: Why are you even encouraging me?

S: Because I want the big dick?

Me: Urgh.

S: I want to try doesn't mean I'll like it ok?

Me: Then you still want the threesome? Double penetration?

S: Maybe.

Me: You're all making me go crazy.

S: I'm sure you can handle it. You've been a tool for so many women. No point stopping now.

Me: Fine. Don't regret your decision.

S: Live with no regrets. Don't regret yours.

We cuddled for a while longer before heading out to the prata place for dinner.

I texted Darren her address and told him I'd head over to his place at 11. He told me to liaise directly with Natasha instead so I texted her.

Me: Hey Nat, I'll be coming over at 11.

N: Can't wait. Thank you.

I wondered if I should get any supplements, considering I had already cum a couple of times today. I really wondered if I would be able to pleasure her well. And Shirlyn was expecting me to return to her afterwards. Part of me was beginning to wish I was 10 years younger.

[jwat]

Hope Mark will bring two filet o fish to N house.

Damn. Saw it coming. Mark cucked again. Sort off. The possible real pain, when Mark go back to serve Shirlyn, and Shirlyn unable to ..., and just maybe can cuddle, or only the wrong hole. Or Shirlyn walking weird.

Take care Mark. Hope you don't have performance anxiety. Camping the Darren and Shirlyn episode (will Shirlyn voice call you ? during thier deeds ?) This is overnight ?

Camping for disastrous Mark and Rebecca and Mark and Karen episode.

At this point, why not.

[ouzo18]

Originally Posted by jwat

Hope Mark will bring two filet o fish to N house.

Damn. Saw it coming. Mark cucked again. Sort off. The possible real pain, when Mark go back to serve Shirlyn, and Shirlyn unable to ..., and just maybe can cuddle, or only the wrong hole. Or Shirlyn walking weird.

Take care Mark. Hope you don't have performance anxiety. Camping the Darren and Shirlyn episode (will Shirlyn voice call you ? during thier deeds ?) This is overnight ?

Camping for disastrous Mark and Rebecca and Mark and Karen episode.

At this point, why not.

Lol, ya he should have duck rice for dinner, then filet o fish for supper. Then the whole night rock hard, fuck until both of them surrender. And we will call Mark.....The God Of Fuck...lol

[junior_cannibal]

Mark and Darren are really orgy. Though in a separate places but with common partners.
If a woman has a big dick to fill her up before, just for sex sake, she's less likely to want a smaller one. Disregarding the skill and experience, and maybe the BFE.
Whatever that's being termed, what commercial break and stuff.
Anyway, Mark, as you are not exclusive to anyone, a Jasmine included, you really better to enjoy all these while they last.

[sexcision]

Originally Posted by Shrouded

S: Good. Don't think. Just do.


S: Put yourself in our shoes. You sleep with us. Then you go sleep with others. Don't you think we wonder why? Or question what we did wrong to not be able to hang on to you?


S: You appear to be so experienced in this. Fuck buddy or friends with benefits relationships. But in fact you're not. You can't handle the emotional fallout. But you hide it very well.

I really think Shirlyn make some really good points there.

Regarding the supplements, just get it from Darren. treat it as referral fees hahaha

[EnigmaofSorrow]

Originally Posted by sexcision

I really think Shirlyn make some really good points there.

Regarding the supplements, just get it from Darren. treat it as referral fees hahaha

Based on the last few updates, Shirlyn also is not as innocent and drama-free unlike what some bros mentioned.

Therefore, not the ideal candidate for a proper relationship.

But, there may be a chance she is like this as she is adapting to the situation. Or Mark's situation.

[sexcision]

Originally Posted by EnigmaofSorrow

Based on the last few updates, Shirlyn also is not as innocent and drama-free unlike what some bros mentioned.

Therefore, not the ideal candidate for a proper relationship.

But, there may be a chance she is like this as she is adapting to the situation. Or Mark's situation.

I agree, she did mentioned that she had thought it over the last few weeks and also the introduction of all the "I have been fucked by Mark" ladies seems to have opened her eyee and mind. She might not be like that previously considering her last sex partner is her ex bf. And most importantly, she is not exposed to these lifestyle.

So in a way, I do believe Mark himself is the triggering points for all the ladies evolving with exception to Ann and Felicia whom had already evolved before meeting Mark. Or rather, they are the one who evolved mark who than evolved jas and Shirlyn.

[asean12345]

Originally Posted by EnigmaofSorrow

Based on the last few updates, Shirlyn also is not as innocent and drama-free unlike what some bros mentioned.

Therefore, not the ideal candidate for a proper relationship.

But, there may be a chance she is like this as she is adapting to the situation. Or Mark's situation.

Non of the girl are ideal candidate. Even Mark are not an ideal husband material. No one is losing on this arrangement. Until Mark can control his own lust and have strong determination, nothing change.

At end of this whole episode, everyone are winner.

[sexcision]

Originally Posted by junior_cannibal

Mark and Darren are really orgy. Though in a separate places but with common partners.
If a woman has a big dick to fill her up before, just for sex sake, she's less likely to want a smaller one. Disregarding the skill and experience, and maybe the BFE.
Whatever that's being termed, what commercial break and stuff.
Anyway, Mark, as you are not exclusive to anyone, a Jasmine included, you really better to enjoy all these while they last.

BFE = Boyfriend Experience which takes after GFE Girlfriend Experience

[bondage]

This complexity is beyond imagination. No one is really in control or self-control. Go with the flow then.

[Shrouded]

I headed over to Natasha's place slightly earlier than expected.

The guard let me in easily as expected.

I dropped her a text to let her know I was early.

N: Come up. I'm getting ready.

I wondered what she was getting ready for.

I headed up and rang the door bell. The door opened and Natasha stuck her hand out, pulling me in.

She was completely naked and pushed me onto the sofa, ripping off my clothes.

Me: Woah. Slow down.

N: I haven't had sex the whole week.

Me: Oh.

N: I want you in me.

Me: Slow down. Let me pleasure you.

N: What?

I sat her down and spread her legs. She was freshly shaved, so that was what she meant by getting ready.

I kissed her neck, working my way slowly down her small chest. Her nipples were already hard. I flicked at them and they moaned. They were like those pencil erasers. I moved down her flat stomach, then her thighs. She spread her legs wider in anticipation. But I ignored her, moving my mouth and tongue further down, to her calves.

She grabbed my head, pulling slightly at my hair, as if she was trying to get my face to her pussy. I resisted, and instead went up the other calf and thigh, planting soft kisses, and running my tongue along.

She gasped as the tip of my tongue first touched her labia. I ran it down then up the other side, I could feel the freshly shaved feeling.

I slid a finger in, she was already soaking wet. I planted my mouth on her clit and teased it with my tongue, my other hand slowly moving upwards to her breasts. I gave it a light squeeze before taking a nipple between my thumb and forefinger, rolling it around, flicking at it, while alternating between licking and sucking lightly on her clit.

I slide another finger in, curving them upwards and feeling around for the mound of flesh that supposedly was the g-spot. I glanced up and realised she was squeezing her other breast, and stimulating her nipple. Her soft moans grew louder and she started to clamp around my head with her thighs, but at the same time trying to push me away. I didn't give in and increased the pace of my licking and fingering.

She gave a little shriek as her lower body trembled vigorously. I refused to stop and her moaning/breathing got heavier. The trembling became more powerful and she was somehow sliding off the sofa.

I stopped for a couple of seconds to push her back up, before attacking her again.

She held onto my head.

N: Why are you doing this? Stop.

Me: I'm pleasuring you.

N: That's longer than anyone ever has. Even Darren.

Me: It's only been like 10 minutes?

N: I already came.

Me: That's good.

I pulled the hood back and tongued her swollen clit again.

N: Let me pleasure you. Please…

Me: Oh I'm feeling lots of pleasure now.

N: You're weird.

Me: I know.

She came again from my mouth and fingers.

N: You drained my energy.

Me: Ah. Oops.

N: I wanna suck you but I can't move.

Me: It's fine.

N: I think you're over-compensating.

Me: Am I?

N: You think your dick is small. Compared to Darren perhaps it is. But your willingness is madness.

Me: Shouldn't you be pleasured as much as the guy?

N: If I was a feminist I'd be sitting on your face all the time. But…

Me: But?

N: You have a nice cock. And I want to suck it. At least I can deepthroat you without gagging too much.

Me: With practice you probably could deepthroat Darren too.

She laughed.

N: I've had nearly 2 decades of practice. Trust me, I can't. I should be able to fit him nicely into me, I can't.

Me: Practice more?

N: Oh please. He cums so fast. I'm nowhere near cumming and he already blows his load. He recovers fast but the feeling is gone.

Me: But he still recovers fast.

N: You last long. I'll give you that.

Me: Condoms help a lot.

N: Are you conning me to do it raw with you?

Me: No… I didn't mean that. I'm just saying it helps to desensitize. Maybe get Darren to use them?

N: And why the hell do I need to use condoms with my own husband?

Me: Trying for third kid?

N: Haha. It would be magic if I get pregnant again.

Me: Oh?

N: Tied my tubes. He didn't want to get a vasectomy.

Me: I see.

N: So technically… we could do it raw.

Me: Sorry. I'm not comfortable with that.

N: Yeah. I'm not with you either. You've had so many partners.

Me: Darren insists on condoms with the rest anyway.

N: Yes. That's how we protect each other.

Me: So you never had it raw with anyone else?

N: Honestly? Jason came inside me once.

Me: Really?

N: Darren doesn't know. So don't tell him.

Me: Oh.

N: He was being really dominant that day, even choking me a little. It turned me on a lot.

Me: Ah.

N: So I told him he could remove the condom and shoot inside if he dared to.

Me: And he did.

N: Yeah. And he came in less than 5 thrusts.

Me: Oh. Well, you're tight. Even for me.

N: If anyone my size isn't tight, I really wonder what's going on down there.

Me: Well, I respect your decision.

N: And I hate it when guys cum too fast.

Me: Thankfully I don't. Condom or not.

N: Still sounds like you're conning me.

Me: Haha. I'm not. I'm just bragging.

We got up and proceeded to the bedroom. She asked me to lie on the bed and she gave me a catbath, licking me all over, before heading to the desired destination. It felt like she was trying torture me the way I did to her but it wasn't working. I had already cum more than once earlier and while I could get hard, especially from the vacuum cleaner sucking, I was pretty sure I wouldn't cum so easily, or even cum a lot.

I flipped her into a 69 as she blew me, teasing her with my tongue and fingers, and distracting her from her task. I think she was getting a little irritated that she could not blow me properly.

She got off the bed, grabbed the condoms, I saw it was a 001 version, capped me and got on, sliding in with ease.

While the condom really made a difference in sensitivity, the thinness of the condom played a part too. I guess the previous time she used normal condoms as this time I felt so much more of her insides. Maybe I shouldn't have bragged about lasting long earlier. With this condom, there was no way I could last. But at least with her on top and controlling the flow, I would definitely last longer than 5 thrusts.

She rode herself to two orgasms before getting off and ripping off the condom, going down on me again.

Me: Hey… I'm still hard you know.

N: I know. I just really love sucking your cock.

Me: More than when it's inside you?

N: Yes. I really like the size.

Me: So I guess Jason and the other guy is about the same size?

N: Would it comfort you to know that you're slightly bigger? Since you seem to be having issues with your size.

Me: I don't have issues with my size.

N: Ya right.

She continued slurping on my cock noisily.

N: If you don't have issues, why do you keep talking about bigger cocks?

Me: Envious maybe?

N: Bigger cock doesn't mean better skills. Although with your skills, your willingness to please, if you had a bigger cock, I'm sure there's a long line of women queueing up.

Me: How would they even know about my skills and whatever else.

N: You know they say don't kiss and tell right?

Me: Yeah?

N: Everybody does it. Trust me. Your lady friends definitely all talk about Darren, and you, and probably every guy they slept with. Darren tells me about them too. Like how Alicia is needy, Felicia is crazily horny.

Me: What about Jasmine?

N: I don't think he knows much about her. I think they only slept together twice. And once was with you, and Alicia.

Me: She keeps talking about wanting a bigger cock to fill her up. Even wanted me to introduce EoS to her.

N: Hahahaha. That doesn't mean anything. Besides, even if she was sleeping with Darren, or EoS, or anyone else for that matter, why should you bother?

Me: It bothers me. I don't know why.

N: It's obvious you like her a lot. And she likes you to. She's going through a difficult phase of her life right now and the best thing you can do is to be supportive of her wishes.

Me: I am. I'm trying my best. But I'm afraid she'll find someone else.

N: Yet you're here right now. You say you don't want to but you still do it. You had sex with another girl this afternoon. Don't be a hypocrite. Either you enjoy the sex you're having now, with whoever you're having it with, and stop beating yourself up over it, or you can just go be alone and wait for Jasmine. Everyone has their own way of dealing with their issues or needs.

I really didn't have a reply.

N: If you're so concerned about what Jasmine is doing, then you should be with her 24/7. Don't give her any space at all. Who cares if she isn't divorced yet? Just spend all your time with her. Let her know you are there for her.

Me: I can't do that.

N: Why not?

Me: I should give her time and space to work out her issues right?

N: Is that what you want to do?

Me: Yes.

N: Then don't bother about what she's doing. And don't bother about what she thinks you're doing. When the time is right, if she still wants you, she will come back to you.

Me: You make it sound so easy.

N: And you make it complicated.

She stopped blowing me and got on top again, sliding it in.

Me: Erm. Condom?

N: Shit. You distracted me.

She got off and unwrapped another condom, unrolling it over my dick, before sliding it in again.

N: Do you feel a difference?

Me: Yup. Definitely.

N: Too bad for you then.

She rode herself to another orgasm before getting off.

N: Ok. I'm done. Your turn.

I started going down on her again but she pulled me up by my ear.

Me: Hey!

N: Use your cock please.

I positioned and slid in with some resistance.

N: I'm dry. Weird.

Me: I think it's because we talked too much.

N: Ya la! Who has heart to heart talks during sex? Weirdo.

Me: It's ok. I can make you wet.

I went down again but she pulled me up.

N: Forget it. Just put it in, it will get wet eventually.

I shrugged.

Me: Ok…

I pushed in again, it must have been uncomfortable for her as the dry condom rubbed against her inner walls. There was so much friction.

But she was right, with each sandpapery thrust, I could feel the resistance getting less and less as she self-lubricated.

Soon enough, I was pounding away at her and rubbing her clit and nipples while she grabbed the sheets.

She took my closer hand and placed it on her neck.

N: Gently? I trust you.

Me: You mean choke or fuck?

N: Choke la! How you going to fuck my neck?

Me: Right.

I squeezed her neck gently as I pounded her hard. She dug her nails into my back.

Within minutes I wanted to cum, she was so tight, and the contractions were coming quick and fast. She could sense that I was going to cum so she wrapped her legs around my back.

I released whatever I had left in the tank into her.

Suddenly her eyes widened.

N: Erm. I think the condom broke.

Me: Oh?

I pulled out and true enough, only the shaft was wrapped. My dickhead was bare.

N: I felt your cum spurting in me.

Me: Ah… it was so tight I couldn't tell the difference.

N: And fuck. Where's the rest of the condom?

Me: Somewhere inside?

N: Well help me dig it out?

I inserted a finger in and probed around, trying to find the broken rubber.

Nat squirmed as I fingered her.

N: Fuck la! Why are you trying to make me feel good when you're trying to find the condom??

Me: Not on purpose.

I finally found the offending piece and fished it out.

N: So you came inside me accidentally.

Me: Probably shouldn't have forced it just now when you were dry.

N: Who knows the condom will break so easily?

Me: It's 001. Very thin.

N: Maybe you fucked too hard.

Me: Well at least you won't get pregnant.

N: Did it feel good?

Me: Cumming inside?

N: No. Raw sex.

Me: Not sure if condom breaking is considered raw.

N: It is la. Your dickhead was rubbing inside.

Me: Really can't tell the difference just now.

N: It will never happen again.

Me: It won't.

N: I'll get tested. You should too.

Me: Ok.

N: Do you still want to do it?

Me: You mean right now?

N: Yeah.

Me: I don't have the same recovery speed as Darren.

N: What a pity.

Me: You did enjoy yourself right?

N: Yes. You need to stop seeking validation from others. Be confident in your abilities. You can tell from our reactions if we enjoyed ourselves or not.

Me: I'll try.

N: You're good enough. Trust me. And everyone else you're fucking. Haha.

We showered separately and I left. It was nearly 12am. Had we really been talking and fucking for that long? Time seemed to fly.

Shirlyn had texted me at around 1130.

S: We're already done and chatting. What time will you be back?

Me: On my way now.

There was no reply so I headed back to her place, mentally preparing myself for a threesome with Darren.

[entering]

Originally Posted by Shrouded

There was no reply so I headed back to her place, mentally preparing myself for a threesome with Darren.

So weird reading this after watching Rurouni Kenshin. It's like the whole image and scene have become a Japanese drama for me with very good looking lead actor and super pretty japanese wives.

[JosephM]

Amazing story, support support!

[funfox]

Awesome all round sex. It’s like mass orgy but each couple at different locations.
Odd to fuck and have serious conversations but as long as it works for Mark, fuck it I guess. Hahaha 🤣