Sissy Would You Rather Questions: 60 for Couples and Solo Play
By Aria Wilde · updated 2026-11-05 · 5 min read
Would-you-rather games work because a forced choice is easier than an open question. "What do you want?" is hard. "Would you rather wear lace or satin?" is easy. These sixty questions run from soft to spicy, with rules for playing as a couple or alone, and a way to turn the answers into something useful.
How to play
- Choose a setting. Relaxed, private, no rush. Wine is optional, pressure is not.
- Start with level one and move up only if both of you want to.
- Answer honestly, not impressively. There are no right answers.
- Veto freely. "Neither" and "pass" are valid replies.
- No judging. No laughing at an answer. Curiosity only.
- Mark answers as yes, maybe or no on paper. This becomes your limits sheet later.
Playing alone? Write your answers in a journal and add a sentence on why. That reasoning is the interesting part. Sissy journal prompts are a good follow-up.
Level one: soft
- Would you rather wear silky pyjamas or a soft cotton nightie?
- Would you rather paint your nails a pale pink or a deep red?
- Would you rather be given a girly nickname or a new feminine name?
- Would you rather wear matching underwear under your normal clothes or keep it only for private evenings?
- Would you rather have a skincare night or a makeup lesson?
- Would you rather pick a perfume or pick a lipstick?
- Would you rather practise a soft voice for a minute or sit in a feminine posture for a minute?
- Would you rather wear a headband and robe or a ribbon in your hair?
- Would you rather be told "good girl" or "pretty thing"?
- Would you rather read a story about a first makeover or listen to one in audio?
- Would you rather get a manicure or a pedicure?
- Would you rather dress up for a quiet night in or a photo set no one else sees?
- Would you rather pick the outfit yourself or be handed one?
- Would you rather start with socks and tights or a camisole?
- Would you rather your partner help you dress or watch you do it?
Level two: medium
- Would you rather be given a daily feminine task or a weekly challenge?
- Would you rather wear a wig for an evening or a full outfit for one hour?
- Would you rather follow a dress code at home or a written list of rules?
- Would you rather practise walking in heels or practise sitting and posture?
- Would you rather be asked to curtsy or to serve tea?
- Would you rather be called a sissy as a pet name or only in a scene?
- Would you rather wear a maid outfit for chores or a dress for a date night?
- Would you rather be interviewed with questions about your feelings or given a quiz?
- Would you rather record a voice message in a soft voice or write a letter in character?
- Would you rather ask permission for small things or be given a daily schedule?
- Would you rather wear lingerie under work clothes or keep it for home?
- Would you rather lose a game and accept a mild task or win and choose one for your partner?
- Would you rather make a vow in writing or say it aloud?
- Would you rather have a "no touching" evening or a "no talking" evening?
- Would you rather practise makeup alone or with guidance?
Level three: spicy
- Would you rather be teased and denied for an evening or given a reward with a condition?
- Would you rather wear a chastity cage for a few hours or follow strict rules about touching?
- Would you rather be tied to the bed or blindfolded?
- Would you rather get a firm instruction or a whispered one?
- Would you rather be told you are not allowed to finish or told to wait until you are given permission?
- Would you rather be praised for obedience or corrected for slips?
- Would you rather train with a strap-on toy or wear something under your clothes all day?
- Would you rather be put in a collar for an evening or wear a private symbol?
- Would you rather spend a night in a full outfit, playing a role, or have a scene built around one object?
- Would you rather be edged to the brink or given a long massage?
- Would you rather receive a punishment you choose or one chosen for you?
- Would you rather serve at your partner's feet or be placed in a corner to wait?
- Would you rather be told a fantasy in whispers or read one aloud?
- Would you rather hear a hypnosis track together or have it played for you?
- Would you rather be rewarded with an orgasm or a long cuddle?
Questions for talking, not playing
- Would you rather talk about your fantasies before a scene or after?
- Would you rather set limits in writing or by conversation?
- Would you rather use a safeword or a colour system?
- Would you rather check in every week or after each scene?
- Would you rather keep this private forever or tell one trusted friend?
- Would you rather have aftercare with a blanket and a drink or with talking?
- Would you rather go slow or decide a pace in the moment?
- Would you rather start with audio or with clothing?
- Would you rather have a plan or a surprise?
- Would you rather ask for what you want or be asked?
- Would you rather repeat a favourite scene or try something new each time?
- Would you rather a gentle scene or a strict one?
- Would you rather your partner lead or share the lead?
- Would you rather keep a journal or leave notes for each other?
- Would you rather stop here tonight or carry on tomorrow?
Turning answers into a limits sheet
Copy every question onto a sheet with three columns: yes, maybe, no. Review it together once a month; preferences change. A "maybe" means "talk first, go slowly". The kink yes/no/maybe list is a longer version if you want more detail.
Playing safely
Consent is ongoing, and you can change your mind mid-scene. Agree on a stop word before spicy questions move to action, and never push a partner to answer something they skipped. If the game brings up shame or anxiety, pause and talk. Sissy shame and acceptance helps with that side.
What to do next
If the answers were mostly soft, a calm audio session such as sissy hypnosis for beginners is a natural next step. If you leaned toward structure, the Sissy Academy gives you a free path to follow, and sissy training with your girlfriend covers playing together.
Frequently asked questions
What are sissy would you rather questions?
They are forced-choice questions about feminine clothing, tasks, roleplay and play, designed to reveal preferences without pressure. They work best as a conversation starter between consenting adults, or as a solo journaling prompt.
How do I use them with my partner?
Start with the soft level in a relaxed setting, answer honestly, allow passes, and mark each answer as yes, maybe or no. Move up a level only when both of you want to.
Can I play alone?
Yes. Write answers in a journal and add a sentence on why. The reasoning often tells you more than the choice itself.
What if my partner says no to something?
Accept it without argument and mark it as a limit. A no is useful information, and respecting it builds the trust that makes other yeses possible.
Should I turn answers into actions straight away?
No. Review the answers, pick one low-risk item and try it later with a clear way to stop. Talking first reduces regret.
Listen next
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