u/BartDPP

Your sister, Melanie(21), and me, Hannah(22), have been in a long comitted relationship. It was obvious to anybody around us, that our relationship consisted of a lot of fun and love. From the outside everything seemed so perfect. Yet, it wasn't.

Unfortunately your sister's insecurities got the better of herself from time to time. She feels like she's not good enough for me, and that I would probably cheat on her the first chance I'd get. At this point it's started to affect our relationship too.

At a desperate last effort Melanie reaches out to you: her trusted sister. She asks you if you could try to seduce me to see if I was actually loyal to her or not.

Even though you were skeptical at first, the idea started to grow on you. Surely, the more you thought about it, the more it seemed like a win-win. Even if I didn't fall to your temptations, you could simply blame your sister for putting her up to it. And if I did? Melanie wouldn't need to know you finally got a first hand taste of all that loud fucking that's been keeping you up at night.

So you agreed and hatched a plan. You sister would invite me over, in the apartment that the two of you shared, to come hang out. Shortly after arriving, she would pretend to receive a call from her boss, claiming there was an emergency he needed her in for. She'd ask me to wait for her before stepping out the door.

And that's exactly how it all played out. Melanie had just left the house 5 minutes ago, and would be staying night with a friend, giving you all the time to properly test my loyalty. Meanwhile I was calmly seated on the living room couch, scrolling through my reels.

What will you do?

===================

Hello! Thanks for making it all the way down here!

This is a scene I've had in mind for a little while now and I'd love to hear your thoughts on it. I'm completely flexible on your own interpretations or changes you have in mind!

Maybe you'd want to turn this into a blackmail roleplay, where you explain the situation to me and threaten that she will claim my infidelity if I didn't do exactly as you say.

Maybe your intentions weren't for a one night stand, but rather for an fuckbuddy that will continue to fuck you behind your sister's back?

Maybe you were actually looking to have a little addition to the family as you plan on getting impregnated that night!

I would love to hear your thoughts!

\*I am 18+ and all participants and characters must be 18+\*

It was a hot summer day and the plane had just touched down at the airport in Hawaii. We were there on a “business trip” to discuss a couple of things with potential clients for my company. It was more like a paid vacation however since they paid for a week and what you had to do would only take about a day. Officially you were there as my personal assistant, my intern. Unofficially you were there as something completely different.

It had started just a few weeks prior. We just finalized a giant business deal and to celebrate I invited you to my office for a glass of whiskey. The good stuff. One glass became two. Two became four. And four became... well, stains on the floor as we knocked them over while fucking on my desk.

Turns out alcohol was quite the aphrodisiac for us, but not as much at the recklessness of it all. Sure, both of us wanted to be careful and didn't want any unintended consequences for our little escapades. Yet when push came to shove, grabbing a condom was the furthest thing on either of our minds. We simply craved that raw, natural feeling of bareback. We craved for that sweet release, that deep creampie that symbolized a good fuck. Sex between us didn't feel quite complete if it wasn't running down your thighs after the fact.

We had to remain secretive about it though. If this leaked out while my divorce was still being finalized, it could lead me to losing everything to my wife. I made sure we were very careful about this trip as well. I even purposely booked two separate hotelrooms, so the cheque would reflect that, both of us fully aware that one of those rooms would remain unused, while the other would certainly be not.

Down on the ground I ordered a Uber black for us which was going to take us to our hotel. Getting into the car brought us our first moment where we weren't surrounded by tons of poeple after a 12 hour flight.

"So, how's your first business trip going so far?" I ask, turning to you. I place my hand on your thigh.

=========

Hello! Thanks for reading this fun idea I had for a roleplay!

When I originally wrote this, it was intended for a middle aged man and his younger intern. That, and any other details in the prompt, can be changed if you have a fun idea in mind!

I would love to hear your take, and your thoughts on all of this, including your kinks and limits!

For those that are interested,

I would love to explore a slightly altered version involving baby-trapping. In that, your character would be actively trying to get pregnant on this trip. Whether through purposely hiding condoms, begging for raw sex and 'forgetting' to stop while riding, or even outright leglocking me right before I can pull out.

*I am 18+ and all participants and characters must be 18+*

It was a hot summer day and the plane had just touched down at the airport in Hawaii. We were there on a “business trip” to discuss a couple of things with potential clients for my company. It was more like a paid vacation however since they paid for a week and what you had to do would only take about a day. Officially you were there as my personal assistant, my intern. Unofficially you were there as something completely different.

It had started just a few weeks prior. We just finalized a giant business deal and to celebrate I invited you to my office for a glass of whiskey. The good stuff. One glass became two. Two became four. And four became... well, stains on the floor as we knocked them over while fucking on my desk.

Turns out alcohol was quite the aphrodisiac for us, but not as much at the recklessness of it all. Sure, both of us wanted to be careful and didn't want any unintended consequences for our little escapades. Yet when push came to shove, grabbing a condom was the furthest thing on either of our minds. We simply craved that raw, natural feeling of bareback. We craved for that sweet release, that deep creampie that symbolized a good fuck. Sex between us didn't feel quite complete if it wasn't running down your thighs after the fact.

We had to remain secretive about it though. If this leaked out while my divorce was still being finalized, it could lead me to losing everything to my wife. I made sure we were very careful about this trip as well. I even purposely booked two separate hotelrooms, so the cheque would reflect that, both of us fully aware that one of those rooms would remain unused, while the other would certainly be not.

Down on the ground I ordered a Uber black for us which was going to take us to our hotel. Getting into the car brought us our first moment where we weren't surrounded by tons of poeple after a 12 hour flight.

"So, how's your first business trip going so far?" I ask, turning to you. I place my hand on your thigh.

=========

Hello! Thanks for reading this fun idea I had for a roleplay!

When I originally wrote this, it was intended for a middle aged man and his younger intern. That, and any other details in the prompt, can be changed if you have a fun idea in mind!

I would love to hear your take, and your thoughts on all of this, including your kinks and limits!

For those that are interested,

I would love to explore a slightly altered version involving baby-trapping. In that, your character would be actively trying to get pregnant on this trip. Whether through purposely hiding condoms, begging for raw sex and 'forgetting' to stop while riding, or even outright leglocking me right before I can pull out.

I am 18+ and all participants and characters must be 18+.

Your sister, Melanie(21), and me, Bart(22), have been in a long comitted relationship. We met as teens and were eachother's first everything. First love, first kiss and even first (and only) fucks! From the outside everything seemed so perfect. Yet, it wasn't.

Niw, years later, your sister's insecurities got the better of herself from time to time. She feels like she's not good enough for me, and that I would probably cheat on her the first chance I'd get. At this point it's started to affect our relationship too.

At a desperate last effort Melanie reaches out to you: her trusted sister. She asks you if you could try to seduce me to see if I was actually loyal to her or not.

Even though you were skeptical at first, the idea started to grow on you. Surely, the more you thought about it, the more it seemed like a win-win. Even if I didn't fall to your temptations, you could simply blame your sister for putting her up to it. And if I did? Melanie wouldn't need to know you finally got a first hand taste of all that loud fucking that's been keeping you up at night.

So you agreed and hatched a plan. You sister would invite me over to hang out in the apartment you and your sister share. Shortly after arriving, she would pretend to receive a call from her boss, claiming there was an emergency he needed her in for. She'd ask me to wait for her before stepping out the door.

And that's exactly how it all played out. Melanie had just left the house 5 minutes ago, and would be staying night with a friend, giving you all the time to properly test my loyalty. Meanwhile I was calmly seated on the living room couch, scrolling through my reels.

What will you do?

===================

Hello! Thanks for making it all the way down here!

This is a scene I've had in mind for a little while now and I'd love to hear your thoughts on it. I'm completely flexible on your own interpretations or changes you have in mind!

Maybe you'd want to turn this into a blackmail roleplay, where you explain the situation to me and threaten that she will claim my infidelity if I didn't do exactly as you say.

Maybe your intentions weren't for a one night stand, but rather for an fuckbuddy that will continue to fuck you behind your sister's back?

Maybe you were actually looking to have a little addition to the family as you plan on getting impregnated that night!

I would love to hear your thoughts in your reply.

Your sister, Melanie(21), and me, Hannah(22), have been in a long comitted relationship. It was obvious to anybody around us, that our relationship consisted of a lot of fun and love. From the outside everything seemed so perfect. Yet, it wasn't.

Unfortunately your sister's insecurities got the better of herself from time to time. She feels like she's not good enough for me, and that I would probably cheat on her the first chance I'd get. At this point it's started to affect our relationship too.

At a desperate last effort Melanie reaches out to you: her trusted sister. She asks you if you could try to seduce me to see if I was actually loyal to her or not.

Even though you were skeptical at first, the idea started to grow on you. Surely, the more you thought about it, the more it seemed like a win-win. Even if I didn't fall to your temptations, you could simply blame your sister for putting her up to it. And if I did? Melanie wouldn't need to know you finally got a first hand taste of all that loud fucking that's been keeping you up at night.

So you agreed and hatched a plan. You sister would invite me over, in the apartment that the two of you shared, to come hang out. Shortly after arriving, she would pretend to receive a call from her boss, claiming there was an emergency he needed her in for. She'd ask me to wait for her before stepping out the door.

And that's exactly how it all played out. Melanie had just left the house 5 minutes ago, and would be staying night with a friend, giving you all the time to properly test my loyalty. Meanwhile I was calmly seated on the living room couch, scrolling through my reels.

What will you do?

===================

Hello! Thanks for making it all the way down here!

This is a scene I've had in mind for a little while now and I'd love to hear your thoughts on it. I'm completely flexible on your own interpretations or changes you have in mind!

Maybe you'd want to turn this into a blackmail roleplay, where you explain the situation to me and threaten that she will claim my infidelity if I didn't do exactly as you say.

Maybe your intentions weren't for a one night stand, but rather for an fuckbuddy that will continue to fuck you behind your sister's back?

Maybe you were actually looking to have a little addition to the family as you plan on getting impregnated that night!

I would love to hear your thoughts!