Why not try the back door
This is part of an ongoing series. If you don't read the earlier episodes, you are missing out. I recommend starting from the beginning. Each one builds on the other.
My name is Ben and my sister-in-law, Jane, are having an affair. We have tricked my wife, Sara and Jane's husband Ron into sleeping together. Originally it was to cover our tracks, but now it has become a salacious game. And Jane wants to see if we can get them to go further.
*****
Jane has laid out her devious plan to me to try and see if we can coerce our spouses into having anal sex together. As before she is going to work on Ron and I am to work on Sara.
When Sara comes home after her weekend with Ron, I greet her and give her a nice big kiss and squeeze her ass. I asked her, "how did the soccer tournament go?"
She says, "it was good the girl's team made it to the championship game but didn't win."
"That's a shame, I'm glad to hear Ron was so helpful. Did you two get along alright?"
Sara looked a little shocked at the question, "how do you mean?"
"Well, we are usually all together. I just wondered if it was weird, it just being you two?"
"No, not at all. You know we are all comfortable around each other."
"I know it's great. I was happy to share you with him for the weekend. I'll have to thank him for taking such good care of you."
I let several days pass, but started touching her ass occasionally. Not so much it was obvious but more than usual.
The next time we have sex, I start by eating her pussy. I stick two fingers in her after she is good and wet, I continue to push my index finger in and out, but I let my middle finger slide out and into the crack of her ass. It slides back and forth in her crack as I push my index finger in and out of her pussy. I can feel her react when my finger crosses her anus. I make it look like it is unintentional and she has no objection. We continue on to have missionary sex.
Later that night when she is sound asleep, I go into my usual routine but change it to accommodate the new objective. I whisper in her ear, "sex with Ron was great. Ron loves your butt too." And I place my hand on her butt. I rub and fondle her butt. "You like Ron's hand on your butt."
The next morning when she is cooking breakfast, I come up behind her and grab a handful of one of her ass cheeks and kiss her. "Good morning. You know you are a sexy woman." She looks at me a little funny but continues on making breakfast.
Two weekends later Ron and Jane come over. As I greet Jane and kiss her, I grab her ass with one hand being sure Ron sees, but Sara doesn't. They kiss a little warmer than usual and we all go in.
After dinner, there is a championship ball game on the TV. Ron and I go to the den and watch it and drink beer. The girls go off somewhere and are chatting.
Jane tells me later, she asks Sara, "I bet you have never had anal sex, have you?"
Sara said, "absolutely not, have you?"
"Hell yes, and girlfriend let me tell you, it is something else."
"Does it not hurt?"
"It does at first, but once you get past that, let me tell you, full-on pleasure."
"I don't think I could ever do that."
"I didn't either, but I was reading this article and it talked about the extreme pleasure a woman could receive from it. It also gave advice on how to do it so it would be less painful and helpful tips and positions to try. So, I decided what the hell and went for it."
"So, Ron has had anal sex with you?"
"Who else do you think, silly?"
"Yeah right, I didn't know Ron would. I'm just trying to imagine it... I mean with you and him. You know, sorry."
Jane looks at Sara devilishly and says, "sounds like you are thinking about trying it."
Then out of modesty Sara whispers to Jane, "I don't think I could do it with Ben, he is so big. It would have to hurt."
Jane pretends to be shocked, "really? How big is he?"
"Well, he is much bigger than..." Sara catches herself. She can't believe she about let the cat out of the bag already.
"Bigger than what honey?"
"Well, um, bigger than most men. I mean from what I have read and the few I have been with."
"Wow, lucky you. Now you make we want to see it. Anyway, I just thought I should let you know how exciting I found it to be. I will send you that article and you can decide what to do."
Meanwhile during half time of the ballgame Ron and I go get another beer. We are standing there talking and I say, "hey Ron, let me ask you something. Have you and Jane ever had anal sex?"
He says, "yes and she loves it. Hell, I do too. I couldn't believe it when she first told me she wanted to try it. I actually was a little hesitant at first, but man after we did, I was hooked. Why do you ask?"
"Well Sara has done a few things to make me think maybe she wants to try it, but like you I am hesitant."
"Really, what has she done?" And then he tries to temper his excitement. "I mean what makes you think she wants to try it?"
"Well, I don't know, it just seems like subtle hints. I may have it all wrong. I don't think I could do it anyway."
Then halftime is over and we finish watching the game.
That night in bed with Sara, I continued my subliminal messaging. I tell her Ron is rubbing her butt as I do it. That Ron thinks her butt is so sexy. Her butt makes Ron get hard. Then I take my finger and slide it up and down her crack and then rub her anus. I am shocked that she immediately releases a sensual moan. I then whisper in her ear. You love Ron playing with your ass. It makes you feel so good.
The next morning when I kissed Jane good morning. I rub her butt and then look over to Ron and wink as if to say I can't believe you tap that.
When we leave and say our goodbyes, I am sure to be positioned where Ron can see me rub Jane's butt, hoping he will soon take up the practice with Sara.
After a few weeks Jane and I worked out a way to get Ron and Sara together alone at our house for a night. We want to see if they are still hot for one another. We have hidden cameras in our house now too, so both are wired to be able to see what happens regardless which house is being used.
When they are talking at first you can see Sara is still a little hesitant to continue an affair, but also clearly does not want to stop. Ron is all in at this point and has no concern. They have hot steamy sex and try a couple new positions.
Later that week in my arousal session at night with Sara, I lubricated my finger just enough to not make a mess I can't clean up. I then stimulate Sara's anus. Ron's cock feels so good rubbing against your ass. You want Ron's cock in your ass. You have to have Ron's cock in your ass. And then I push my index finger in ever so slightly. She gasps and I quickly remove it in the fear I have awakened her. She moves around a little restless but she does not wake up.
I decided to not push it anymore tonight, but I think I felt her ass trying to accept it. Hopefully this is giving her erotic dreams about Ron fucking her ass.
The next weekend we are over at their house. I hug Jane and have Ron see me hold her ass as we kiss. When Ron hugs Sara, one of his hands is much lower than usual. It is not quite on her ass but it is very very close. I think it will be no time now before he is grabbing it.
After supper and before we start playing games, Ron says he is having issues with his car. I say let's go look at it. As we are checking out his car, I say "remember when I said I think Sara is interested in anal sex and you asked me why I thought so?" He says he remembers.
Then I tell him, "Well the other night we were having sex doggy style. Sara takes her hand and rubs her asshole a time or two and then sticks her finger in. I have never seen her do that before. And it seemed to really set her off."
Ron looked at me wide eyed, "Really."
"Yes, don't you think that is a clear sign she is interested in anal?"
"I would say so. You should help her out man."
"I don't know Ron, I mean I want to please my wife, but that has always been so taboo I'm not sure I can do it."
Meanwhile Jane asks Sara, "did you read that article I sent you?
Sara says, "yes I did. It did make it sound very interesting but I just don't think I can do it."