Non-Coerced Feminization Roleplay Ideas

Roleplay scenarios are a fun way to enjoy feminization. Men enjoy dressing in feminine attire for one or more of a myriad of reasons.  Seeking out a strong woman for the purpose of feminization can include a desire for sharing, support, and encouragement.  Advice, and an environment of openness and lack of judgment are further reasons. Regardless of motivation, fashion the following scenarios  to suit your individual needs.

Sissy Roleplay Idea #1

Sissy Roleplay Idea #1: Mistress Dresses Her Sissy Maid For a Dinner Party – You pride yourself on being a model domestic sissy. You complete every task given to you, attend to every fine detail, and always aim to please your Mistress. Mistress just informed you that she is planning to have a dinner party.  You need to dress perfectly for company.

You LOVE getting all dolled up for your Mistress. But… On this occasion, she is not going to simply tell you what to wear and leave things to chance. No. She is going to dress you herself! Depending on the look she wants, she may dress you as a “traditional” classy sissy maid.  Or, on the other hand, a provocative sissy maid. And you can hardly wait to see what look she chooses for you. This non-coerced sissy scenario can include body worship, strap-on sex, cocksucking, and/or chastity. Other scenarios can focus on humiliation [teasing, spanking, cum-eating, panty puddles, public display].

Sissy Idea #2

Sissy Roleplay Idea #2: Mistress Dresses Her Slutty Sissy For a Night Out – Mistress has plans for a night out on the town – and you are going to be accompanying her. Of course, she may not be the only one going out in search of a “real” man. Therefore, you are going to be dressed like a hot, slutty sissy-on-the-prowl. Ready and willing to flirt, seduce, and be used as a sissy man-toy. Mistress will choose just the right spicy lingerie. Barely there top and skirt (or trampy dress), and towering heels for you. Then she’ll dress you for the outing.

This scenario can focus on the experience of being slowly dressed by Mistress, being shown off and pimped out by Mistress, and/or being a helpful sissy slut girlfriend, who is more than happy to be a fluffer for Mistress’ chosen lover. (Assplay/strap-on sex, public display, domme-guided bi/cocksucking, cum-eating, cuckolding can all work well in a slutty night out scene.)

Crossdresser Roleplay Idea #1

Crossdresser Roleplay Idea #1: Trying On That New Outfit – There is nothing more exciting that buying a brand new ensemble, including a new bra and panty set, garter belt, nylons, little black dress, or pencil skirt and billowy blouse, with some sexy stiletto heels. If there’s anything that happens to be more titillating that making the purchase, it is getting home.  And then slipping into your gorgeous new things.

What better way to enjoy, get opinions on, and receive some assistance with your new attire than to have Mistress join you for the fun. She can hand you each item, help hook your bra or buckle those ankle straps for you. You can also model your full look for Mistress and get her feedback on the fit, style, colors, and so on. (A dress-up role-play like this easily accommodates the following elements: guided masturbation, tease and denial, chastity, public display, edging, cum-eating, and/or assplay/strap-on sex.)

Crossdresser Idea #2

Crossdresser Roleplay Idea #2: Shopping Trip Fun – Before you have a fashion show featuring your new feminine treats, you have to go shopping for them. Why go alone? Solicit Mistress to go along and show you how much fun a fantasy shopping trip can be! When Mistress accompanies you on a clothes-buying outing, you have your own personal stylist, advisor, and expert on-hand to ensure you don’t forget anything you need.

Whether it’s focusing on one shop or store-hopping your way around the mall, Mistress can give you suggestions, offer tips and tricks, and help you try on items in the dressing room. Now, that’s a fun day out! (Tease and denial, chastity, guided masturbation, public display, and/or cum-eating can be well-suited elements for a shopping trip fantasy.)

Enjoy these roleplay scenarios? Give one of our feminization Mistresses a call, today!