---
title: "20 Anal Dares for Him, Level 4 Bold"
description: "20 anal dares for him at Level 4, for nights you both want to remember. Free to play online with no signup. Pick one below or spin the Wheel of Kinks to get a random prompt."
url: "https://www.theforeplaygame.com/all-cards/anal/4/male"
markdown: "https://www.theforeplaygame.com/all-cards/anal/4/male.md"
updated: 2026-07-17
---

# 20 Anal Dares for Him, Level 4 Bold

20 anal prompts for him at Level 4 (Bold), for nights you both want to remember. Browse the full list below, or spin the Wheel of Kinks for a random one. Lower the level if you want a warm-up first, raise it when you are both ready.

## Prompts

1. Partner A, would you be excited seeing Partner B wear an anal ring?
2. Partner B lies on her stomach, arching her back and gripping her ankles. Gently massage her anus with your finger until she can no longer bear the pleasure and releases her legs.
3. Partner B lies on her stomach, arching her back and pushing her hips up. Apply some massage oil, lubricant, or coconut oil to your finger and slowly slide it inside her anus, massaging it with a gentle touch.
4. Gently insert one finger into your anus and keep it there until you fulfill the task that your partner has chosen for you.
5. Partner B lies down on her stomach, propping up her pelvis with a pillow. She then opens her legs wide and you begin to tantalize her anus with a different finger each time, using lubricant. See if she can guess which finger you are using correctly three times in a row. Make sure to wash your hands before and after the game!
6. Tie Partner B's arms and legs securely to the corners of the bed, with her pelvic area propped up by a pillow. Gently lubricate one finger and begin to massage her anus. Spank her butt with your free hand, counting out the month and date of her birth. If you want to add an extra thrill, insert a butt plug and if available, use a vibrator but be sure to clean it thoroughly afterwards.
7. Go to the bathroom/other room. Put your finger in your anus (don't forget to lube before) and take a picture on your phone. Then show/send the photo to your partner. After the game, delete it all!
8. Partner B lies down on her back, and you tie her wrists to her ankles (the right wrist to the right ankle, left to left). Then tease her vulva with one hand, place a pinky finger of another hand into her anus and play with it gently.
9. Partner B stands on the floor, puts her hands behind her head, and widely spreads her legs. You blindfold her with a scarf, kneel behind her, and slowly place one or two fingers inside the vagina. Then play with her while kissing her on the butt. (Don't forget to lube!)
10. Partner B takes off her panties, sits on her heels with her legs slightly apart and lies forward on her thighs (if she practices yoga, it's child's pose). Tie her hands behind her back, put lubricant on your finger and place it entirely into her anus. Then hold her firmly on her hands or hair and play with her for a while with your finger inside.
11. Partner B stands on the floor and leaves her hands next to the body. You take the belt, wrap it around her hands in the belt area and tighten it up. Partner B then kneels in front of the bed and lies down on her face. Spread her butt apart and play with your tongue around her anus.
12. Position 69+1. Lie on the side, next to each other upside down, and pleasure each other as you would do in classic 69. However, Partner B raises the top leg, and you will tantalize her anus with a finger.
13. Partner B lies on her belly, puts her legs underneath, and pulls her butt up. Take a lot of massage oil or lubricant, place one finger into her anus and gently massage it.
14. Partner A, take Partner B and gently slide one of your fingers into her cute behind.
15. Partner A, Partner B can choose any object she would like to stick up your butt. Never done this before? Be sure to use some lube!
16. Partner A, spread your cheeks apart so Partner B can get in there with her tongue.
17. Partner A, get down on all fours. Partner B, go behind him and enter him with a sex toy held at your waist.
18. Partner A, Partner B will use her finger to enter and exit you from behind. Tell her the level of deepness that feels the best.
19. Partner A, lube up Partner B's pointer finger so that she can stick it up your butt and move it slowly back and forth. Partner A, tell Partner B if you want her to add her middle finger!
20. Partner A, let a little spit drip from your mouth onto Partner B's bottom. Then spread it around with your tongue.

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