The two couples get to the hotel and after checking in they go upstairs to the double suite they will share for the following two weeks.

Lauren and Charles are more comfortable with the situation. They have been in the lifestyle for eight years now and without waiting any longer than necessary Lauren says to him "alright go to have a shower and then drop your male clothes here and wear the more appropriate female clothing that suits you better. You were allowed to use your old male's clothing for the travel to here but from now on you will only behave as a woman" Charles with his chin up replies "That's alright Mistress Lauren, I will be a true woman now"

Kelly and Alex have more nervous faces. They are new to all of this. They have been convinced by their best friends to come for a holiday where Kelly can join Lauren in sissifying their husbands. Lauren has been talking to Kelly about all the benefits of such a relationship and Charles has told Alex about all the fun that it entails and how much it brought the two of them closer together. They are now ready to discuss the last few details and then to start this adventure that will change their lives for good.

Hi and thanks for reading my idea for this roleplay where an experienced couple brings their best friends to a resort where the wives will be sissifying their husbands and together they will be seducing other men and cuckold their sissy husbands. I'm interested in seeing here the difference between the two couples and how they get into their next adventure together.

Lauren and Charles will bring on all their previous experience. Charles will become a full on sissy, locked in chastity, having bisexual activity with real men that will be fucking Lauren and he will enjoy playing with their cum and eating it.

Kelly and Alex will need to be guided through this to overcome all of their insecurities and understand the advantages of being in an open sissy relationship.

For this roleplay I will provide detailed replies. I do normally provide one reply a day on average. I'm happy to play as one of the two couples. If you would like me to guide the roleplay then it's better for me to play as Lauren and Charles. The names are just randomly chosen, you can change them to anything you'd like. I play only on Reddit DMs so please make sure to message me there if you don't want your message to go to waste.

Kinks I would like to include in this roleplay are: sissy, cum play, sph, anal sex, blowjobs, handjobs, pegging, double penetration, verbal humiliation. Looking forward to starting this with you