Brother sister roleplay sex story
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.
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.”
Now it was Megan’s tur to be shocked. “Wha…” she started to exclaim before Eric grabbed her and kissed her. He scooped her up in his arms and she gave in, wrapping her arms and legs around him, kissing deeply. He lead her to the other side of the room and laid her down in front of the fireplace, then kissed his way down until his face was buried between her thighs.
Tammy sucked me off a bit more before standing and taking me by the hand, leading me to the bedroom. I looked over my shoulder for one last look of Megan pulling her dress off and grasping the back of Eric’s head, pushing him deeper into her.
Several hours later, the house was quiet as Tammy and I lay naked in bed. The blankets were AWOL, and the sheet barely still clung to the mattress. Tammy’s hair and makeup were a mess, and flakes of cum still clung to her cheek and chest. Half my body and most of my face was still a sticky mess.
“We should check on them” she said. We slowly got out of bed and she grabbed something from the nightstand. She took my hand and we went back to the living room. Still on the floor in front of the fire place, on top of a large blanket, Eric spooned Megan, their bodies blending together and illuminated by only the flames.
We approached and they welcomed us. “Trade places?” Tammy asked, and Megan reluctantly rolled away from Eric, giving him one more deep kiss in parting. Tammy took his place, kissed Eric, and assumed the spooning position. He wrapped his arm around her and pulled her back against his stiffening cock. I lay down and Megan spooned back against me, facing Tammy and leaving just enough distance to let her lean forward for kisses. I nestled by cock between Megan’s cheeks and felt some more stirring.
“Tonight was perfect” Megan started. It went even better than I’d hoped. I hope you had fun too.” With that she reached out and traced her fingers up Tammy’s stomach, stopping and her breasts.
“Mmmm, yes… we both picked out some pretty good cocks” Tammy responded. “Your brother really knows how to fuck.” They giggled. Megan responded gleefully “So does your cousin. And thanks again for not judging us. That really would have ruined a wonderful night.”
Eric added “Hopefully not just one night though. This could be a regular thing.” The rest of us simultaneously agreed.
Tammy and Megan started kissing a little, lightly at first, just teasing each other and touching tongues, but then their hands started roaming and the kissing became more passionate. “I have a strap-on I could use on you, if you like,” she said. “It’s in my nightstand.”
“Mmmm… definitely next time, but not now. There’s something else I’m kinda craving.”
“Well don’t be shy now, tell us!”
“Ok, well, I want the two of you to watch while my brother fucks my ass.” As soon as she said it my cock sprang to attention. We hadn’t talked about this, and she gave no indication that she was into anal sex. So I decided that this was more role play and decided to go with it.
“Really sweetie? We’ve never done that before. You always told me that your ass was off limits.”
She rolled to face me. “Well, we’ve done a lot of things tonight that I never thought we’d do. I never thought we’d meet another couple ok with us being brother and sister. I never thought I’d lick your cum off another woman’s cheek. But here we are. I’m going to get on all four, you’re going to fuck my ass, Tammy is going to spread her legs and make me lick her pussy, and Eric is going to fuck her mouth. Sound good to you, big brother?”
Tammy grabbed the thing she’d brought from the bedroom and sat up. “I’ve got lube warming by the fire. I suspected at least one of us would need this.” Megan got on all four, and Tammy spread the warm lube between her ass cheeks, slipping a finger in and making Megan moan. Tammy took me in her hand, lubing me up and guided me in before laying back and positioning herself under Megan’s mouth.
The lube was perfect, and I slid in surprisingly easy. I slowly entered and withdrew while watching the scene in front of me unfold. Megan’s tongue dipped into Tammy, eliciting groans, before she focused on Tammy’s clit, lapping at it and sucking it between her lips. Tammy’s back arched and her head rolled back, already on the verge of an orgasm. Eric leaned in and whispered into her ear “Do you want to suck your counsin’s cock, you nasty little slut?” She nodded and gasped “please!” just before he slipped it into her mouth. She opened wide, taking it in deep, and he grasped the back of her head and proceeded to forcefully fuck her mouth. They’d clearly practiced this.
Soon we were all in a rhythm, thrusting, licking, groaning, and the only question was if we could all cum together. Within just a few minutes we were all reaching a crescendo together when it happened. I filled Megan’s ass with all I had left to give, while Megan’s body shook and convulsed in her last orgasm of the night. She kept her tongue locked on Tammy’s clit, and Tammy’s body also started convulsing, just it had for me several times for me earlier that evening in the bedroom. And while Tammy was gasping Eric withdrew and stroked out one more spurt across Tammy’s cheek and chest.
We all collapsed, gasping and laughing and marveling at the perfection of the evening. One by one we drifted off to sleep.
The next morning, after showers and coffee, Megan and I got back into my car and started the way home. She took the panties out of the cupholder and wiggled back into them.
“I think that went pretty well” I remarked. She was quiet, looking out the window. I added “What do you think?”
“Yeah, it was good, but…” I waited. ” She finally added “I was kinda hoping they’d be disgusted with us, that they’d shun us and we’d have to work to convince them, drag them down to be as filthy as us. They were too quick to accept…. But god the sex was amazing.” She grabbed my hand and gave it a squeeze. Then added “Next time, I want a really nice couple, maybe a really religious couple. I want to corrupt them way beyond anything they thought possible.”
“Im in. Let’s start looking.”