Caught Cheating and Made to Pay

Caught Cheating And Made To Pay

"The thing with Gary is, he expects to have his cock sucked every night and I'm left high and dry." Janet says, sipping the froth from the top of her hot chocolate.

"Mmm. He's still doing that, is he?" I ask, remembering, we've been here before.

It's a wet Tuesday afternoon in our local town centre. Janet and I are catching up after a tumultuous weekend left her sleeping on her settee. Her and her boyfriend are not getting on at the minute.

When she texted and said she needed a catch up, I suspected it would be about Gary. They've been together for four years. She loves him. I know that much.

Since him and Janet had this dry spell, caused by his selfishness, he's been on the swinger's site my husband and I use to find dates.

Janet doesn't know this.

The problem I have, how do I tell Janet about her boyfriend cheating on her. We've messages on the swinger's site we screen-shotted to show her but it feels a bit of a blunt way to do it.

"I'm sure he's having an affair, the bastard!" she says, stirring her coffee a little too fast.

"Janet..." I say, trying to broach the subject.

"Yes?"

"He is." I say, placing my hand on hers.

"He is what?"

"Gary is playing around behind your back."

"He's what! How do you know?"

"I got this message on a site we use, last night. He started messaging Tony and I last week. We haven't replied."

I show Janet the messages.

"What site is this? Are you and Tony on a dating site? Why are you two on a dating site?"

"It's not a dating site. It's a swinging site. Tony and I are swingers. We meet men so Tony can watch me, you know, and sometimes he joins in too."

Janet slumps back in her seat, staring at her coffee.

"I have been wracking my brain, trying to tell you. How to tell you. When to tell you." I say.

"But we're not swingers. Gary and I aren't into that." she says.

"The site has lots of single men and men who are married or in relationships. We don't meet them." I say, trying to reassure her

"How long have you two been doing that then?" she asks.

"Long enough to be able to smell a cheat." I say.

"So what do I do?" she asks.

"What do you want to do? It says here, in his message, he is into pegging. Is that something he has ever said to you?"

"What's pegging?" Janet asks, twisting her face a little.

"You know, pegging... you wear a strap-on and you put it inside him, instead of him putting his inside you."

Janet's hand shoots up to her mouth.

"No way! Really!"

"You know about pegging, don't you?" I ask.

"Yes. But it's people who wear leather with studs in. Kinky folk. Isn't it?"

I laugh.

"No. I peg Tony all the time. Well, sometimes. He likes it. It gives him a prostate orgasm."

"A prostate orgasm? What's that?"

I lean in. "It's one of the best orgasms a man can have. It's like their g-spot."

"Ah. I see. And Gary wants some of that, does he?"

"Looks like it." I say, looking up from my coffee cup.

Janet looks out of the window. Spots of rain land here and there. It wasn't supposed to rain this afternoon. Good job I brought my umbrella.

"What do I do?" she asks.

"I dunno. You could say he's trying to cheat on you. But you could also look at it from his point of view. You too aren't having sex and he needs it."

"Sounds like it needs more kinky stuff as well." she says, her eyes wide at the prosect of indulging him.

"Why don't you talk to him about it." I say.

"And say what? How do I know about it? I would have to tell him you told me. And I would have to say it's you he tried to message."

"We don't show our faces on the site. No one knows it's us."

"Doesn't matter anyway. Send me the screen-shots and I will use them as evidence, if I have to."

"So you're going to give it a try?" I ask.

"I am. I have to. I don't want to split up over this. I might even enjoy it." she says, smiling for the first time since we started chatting.

----

"Are you sure you want to go through with this?" I ask Janet as we stand in the hotel room.

"I'm sure. We have to sort this. And it has to be in a way Gary will remember." Janet says, the gimp mask in her hand while she strokes the ten inch strap-on fastened around her hips.

It's two weeks after Janet and I chatted about Gary over coffee. She hatched a plan and here we are, playing it out. We expect Gary any minute.

A knock on the hotel room door is Janet's signal to hide in the bathroom. She fits her gimp mask as she opens the bathroom door.

"Hi. Come on in. I'm Jane. Sorry my husband couldn't make it today. I do have a friend though." I say, as Gary makes his way across the room to hang his coat up.

"Thanks for meeting me. I realise it's only been a few weeks." he says, checking me out.

I've dressed as I always do, as I won't be me playing today.

"I hope you don't mind. I've a girlfriend who's simply dying to test out her new strap-on. She loves the idea of fucking a guy right in the ass. Is that okay?"

"Of course. Ready when you are!" Gary says, beaming with excitement.

"Let's have those clothes off then. Assume the position. There's towels, ready on the bed." I say, loud enough so Janet can hear. That's her signal. When she's sure he's undressed and lying prone on the bed, face down, that's her cue to come out of the bathroom.

He has a skinny build. His ass is tiny. It's an ass I could cup in my hands. But I don't.

"I hope you're ready for my friend." I say, seeing his girlfriend emerge from the bathroom, looking every inch the dominatrix.

Her shiny red PVC boots look perfect with her glossy, black PVC basque. The cups hide her 36D boobs in a way Gary can't tell it is his girlfriend.

We've agreed I'll do the talking so Gary doesn't recognise Janet's voice. For this part of the meet, Janet's name is Mistress Lisa.

"Okay, Mistress Lisa. I hope you've got plenty of lube for this one. His ass looks very tight indeed. You might have to force it in."

Janet nods. She did think about ramming it in dry but she couldn't bring herself to be so cruel.

The shiny end of the dildo strapped to her waist gleams with lube as she lowers it between his ass cheeks. Pulling his cheeks apart, she aims the tip of the dong directly at her boyfriend's ass hole.

He tenses up.

"Don't tense up." I say, watching the action unfold. "You'll make it harder for Mistress Lisa. And it will be more painful for you. Now relax."

He relaxes and the ten inches of rubber slides inside him, an inch at a time. He gasps and pants as the thick tip drives inside. Janet pulls out and her boyfriend gasps again. She sinks it back in. And withdraws. Back in. And out.

Gary's hand scrambles under him and pushes his semi-erect cock out, between his legs. His balls are a tight sack on top of his dick.

Every time Janet drives her strap-on inside his ass, his dick flinches. He looks back over his shoulder to check out the woman fucking him so mercilessly.

"Eyes on the wall, please." I say, smiling at Janet.

Janet builds her rythmn until her boyfriend squirms beneath her.

His orgasm is muted by the pillow against his face. By the time his orgasm arrives, he is bucking back against the thick tool invading him. He is no longer being fucked, he is fucking the strap-on by pushing his ass onto it.

Janet pulls him down onto his knees and makes him watch as she pulls the condom off the dildo. He watches the rubber pull off, an inch at a time. She makes him kiss the tip.

"That's a good little slut. Kiss my strap-on." Janet says, opening her mouth for the first time. All I can do is watch and wait.

Gary looks up. He looks confused. He looks like he recognises the voice behind the gimp mask.

Janet pulls the mask off in one swoop.

Gary look up at her, afraid. He looks over at me. He looks back up at his girlfriend.

"I can explain." he says, realising he has a LOT of explaining to do.

"Can you?" Janet says.

"Err, no." he says, his head dropping, owning the shame.

"I think you had better get that thing hard because I have this room for the night and you've got a lot of making up to do." Janet says, winking at me.

I pull my coat from the hook by the door and reach for the door handle.

"You two going to be okay?" I ask, before pulling the door open.

"I think we understand each other now." Janet says, looking down at her boyfriend and smiling.

Things worked out in the end. I hope the next time I see them both together, Gary is walking at least a little bit awkwardly.

What do you think?

Do you think Janet did the right thing?