Brother Sister Roleplay

Part 1

It was my first date with Megan. We had been spending the last week chatting via Tinder, and so far we were quite compatible. We were both married, similar age, both had two teenagers at home, both blonde and blue eyed, even worked in similar fields. And we were both looking for partners to explore various roleplay fantasies. I especially enjoyed Megan’s penchant for naughty costumes and sharing pictures. She remarked that she was appreciative of my filthy and vivid imagination.

So as we sat there in the coffee shop on a Sunday afternoon, just out of earshot of the other customers, I was surprised that she proposed something that shocked even me.

“Did you notice that we kind of look alike?” she asked.

“I guess we do. Similar hair, eyes, similar features. Except for me being a foot taller.”

“Right, but do you think someone might look over here and see us and think, like, maybe we were brother and sister?”

“Considering how much we’ve been playing footsie, they would probably think married couple, or at least a couple on a date.”

“Ok, but lets say they didn’t see that, or see us holding hands” as she said that she took my hand in hers, “Or see us making out in the parking lot a few minutes from now. Do you think we could convince a stranger that we were siblings?”

Before I could answer the waitress came back and asked if we wanted anything else. I was feeling playful and asked “Do you need a refill, Sis?”

She flashed me a devilish smile and said “No thanks, I think my brother and I are all set.” The waitress, unimpressed, exited without comment.

“So is that something you’re into?” I asked. “A role play scenario you want to explore that you’re too nervous to ask your husband about?” I leaned closer. “You want to get fucked by your big brother?”

“Yeah, pretty much, but there’s more.”

“So you don’t just want me to fuck you while pretending you’re my naughty little sister?”

She leaned closer. “Fuck, I like it when you say it like that. But there’s more.”

“I’m still here. Tell me.”

And she did.

Part 2

Now it was our second date. We found ourselves in my car, driving to a nearby address. She was wearing the kind of dress that would be perfectly placed in church on Easter or on the floor of a Las Vegas hotel room. Our destination was more of the latter.

“Are you excited?” I asked.

“Hell yes! I can already feel my panties getting wet.”

“Can I feel them too?” I asked playfully. With that she spread her legs and I reached over, gently rubbing her through her wet panties, hitting just the right spot to elicit a gasp.

“I should probably just leave them in the car when we get there.”

“No complaints from me.”

“There” was the home of another couple we met via Tinder. They were a married couple looking for another couple for a foursome and swap. Pictures had been exchanged and wants discussed. The plan was to have a drink and relax and then let nature take its course. They were Tammy and Eric. And they were lead to believe that Megan and I were a FWB couple, experienced swingers and both married to others not in the lifestyle. We gave them just enough information to entice, telling them about our long experience together, our enjoyment of watching each other play with others, etc.

What we would soon be letting slip was the key to Megan’s secret fantasy. She wanted to tell them that that we were siblings, that we enjoyed a sexual relationship together, starting when we were teens and continuing to present, and that we enjoyed group sex where we both participated. But the real key to her fantasy was in their response. Would they hesitate, would they need to be convinced to go through with it. Would they call us sick and kick us out. Would they be ok with it and even encourage it? I admit that I was really interested in what would happen too.

We pulled into the driveway of the nice looking house. “Yep, these panties are definitely staying her.” She wiggled out of them and put them in the cup holder. Then we made our way to the door and rang the bell.

They answered together, Tammy in a crop top and mini skirt, Eric dressed more casually like me. Eric guided us in with a hand on Megan’s back, and Tammy took my hand to lead me to the living room. They were already set up with a pitcher of margaritas and soft music. The sun was just starting to set, so the room was dimly lit.

We sat across from each other to start, drinking and talking and laughing. Of course my hand caressed Megan’s thigh, occasionally moving her dress higher. She wasn’t shy about uncrossing her legs and letting the others see her lack of panties. We kissed each other a few times, deeply and passionately, like long time lovers. On the couch across from us, Eric and Tammy did the same, touching and kissing and teasing each other throughout our conversation.

Megan put our plan in motion when she asked Tammy to tell us the story of the first time she and Eric had sex. Tammy said they grew up in a small town in a rural area, where the weekend norm was a field party with a keg of beer. She said they ended up in the back of a pickup, naked and loudly fucking while 20 other teens watched them and cheered them on. They knew that as long as they were together, group play was going to be something they explored. After moving out of that small town, they learned to be more discerning and discreet without being less kinky.

Now it was our turn to tell our story. I started. “Well we knew each other as teens also, and did some stuff then, but didn’t really start getting kinky until we reconnected as adults. So which story should I tell?”

Megan grabbed my thigh and said “You tell the story about when we were teens, I’ll tell the story about reconnecting.”

“Ok.” As I started, Tammy nuzzled against Eric and started rubbing his crotch through his jeans. Eric moved his arm around her shoulder and started massaging her nipple through her shirt.

“So, typical story, parents are out for the evening. We order pizza, watching a movie, and something just came over us. I remember you were wearing really short shorts, and you kept waking in front of me showing off your ass.”

“Ha, yeah, I loved how my ass looked in those shorts. I used to love sending pictures of me in those shorts to guys I had crushes on.”

“I never got a picture.”

“No but you got to see me in them every day.” She playfully hit my chest and let her hand fall into my lap. She then started mirroring Tammy and rubbed me through my jeans while parting her legs and letting her dress fall open.

“Finally I couldn’t take it anymore. I reached out and hooked a finger under the waistband and pulled, and they just slipped right down. And of course you weren’t wearing any panties. You stood there in front of me, completely naked from the belly button down. And you smiled. And you asked if we were finally gonna do this. So I just grabbed you and threw you down and buried my face between your legs and licked you until you came.”

“My first orgasm by the way, except for self-induced.”

“And then you told me it was my turn and got on your knees and proceeded to give me what remains to this day the best blowjob I’ve ever received.”

“Oooh,” Tammy interjected, “the night is still young.” Eric pinched her nipple and she leaned in for a deep wet kiss. That prompted Megan to give me one of the same before I finished my story, as we planned.

“So then the parents came home and we pretended like it was just another boring night before going to bed.” I noticed the first hint of puzzlement from Tammy at that point. She asked “so they let you sleep over?”

Before there could be an answer, Megan chimed in. “There were a few more nights like that when we were home alone, but then years pass, we go off to college, we get married to other people, move away. We still see each other on holidays and talk regularly, fondly remembering that childhood experimentation. And then we just decided to go for it. We planned a weekend away, just the two of us. We both told our spouses that we had to travel home for family reunions, and they both eagerly opted out, as we planned. I checked into a nice spa resort-type place using my maiden name. And we spent the long weekend like a honeymoon. The staff treated us like two newlyweds, and we just drank wine and fucked and used the hottub and sauna and got massages… When we were too tired to fuck we laid on the balcony naked and told all of our fantasies, and we just decided that we weren’t going to let others tell us what to do. We were going to do what felt good for us.

“And it’s so cool” she continued, “to be able to connect with other like-minded hedonists like the two of you who won’t judge and who will help us fulfill our fantasies.”

“And on that note” Eric said, standing from the couch and moving over to the other side of Megan, “I have a few fantasies that I want fulfilled right now.” He sat next to Megan and slid his hand up her thigh, and gave her a deep kiss. While he did that, Tammy came over and knelt between Megan and I, first kissing Megan, then me while sliding one hand under Megan’s dress and the other into my pants.

This was the moment that our plan was building toward; the big reveal. “Tammy, I want you to know that my entire body is available to your husband and to you, to do whatever you want… And I need to know that your entire body is available to me and to my brother to do whatever we want.” And she punctuated that statement by giving me one more giant wet kiss while sliding her hand into Eric’s pants and grasping his cock.

Tammy spoke first. “Oh my god… brother and sister… that’s… that’s…”

Then Eric “That explains the resemblance.”

Megan responded “Please don’t stop, let’s just keep going, we all want this…”

Tammy, still on her knees between my legs looked up to Eric. “Should we?”

“You know what I think. Tell them…”

Tammy’s face lit up, she was beaming as she unzipped my pants and took my cock in her mouth. She let it pop out just long enough to say “Eric and I are cousins. Well, second cousins, and it didn’t slow us down. So it would be a little hypocritical to judge, I guess. So let’s do this.”