---
title: "19 Massage Dares for Him, Level 2 Flirty"
description: "19 massage dares for him at Level 2, a little flirtier, still clothes-on territory. 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/massage/2/male"
markdown: "https://www.theforeplaygame.com/all-cards/massage/2/male.md"
updated: 2026-07-17
---

# 19 Massage Dares for Him, Level 2 Flirty

19 massage prompts for him at Level 2 (Flirty), a little flirtier, still clothes-on territory. 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. Have you ever explored the pleasure of prostate massage with your partner? What sensations did it bring? If you haven't experienced it before, would you be willing to try it out? How might that experience be for both of you?
2. Partner A and Partner B, it's time to play a little game I like to call "Sock Fight!" The objective is to steal socks from the feet of your sock's rival, but be careful not to lose your own in the process. All techniques and tricks, including tickling, are fair game. Just be careful and gentle! The winner gets a glorious foot massage.
3. Partner B should lie on her stomach and slowly slide her pants/skirt off. Take some time to give a soothing massage to her buttocks, using coconut or massage oil for extra relaxation.
4. Using massage oil, warm it up using the heat of your hands and gently knead her feet.
5. Take your time to give your partner a soothing massage. Start with slow, gentle strokes of your palms from the top of her body to the bottom. Let your fingertips lightly caress her skin, creating a peaceful and calming sensation.
6. Partner B and you will share a romantic, erotic experience. She will read aloud a sexy story of your choosing from an online source, while you provide her with a gentle body massage.
7. Partner B should recline in a comfortable position. You will provide her with a full body massage, avoiding any contact with her pelvic area.
8. Both of you kneel in front of each other, embrace your partner, hold her butt and caress it kindly for a while.
9. Put your hand under your partner's blouse/shirt and caress her breasts for a while.
10. Caress and kiss your partner's breasts over her shirt until her raised nipples show off.
11. Partner B sits astride a chair, you stand behind her back and massage her shoulders and neck.
12. Place your hand into her panties and caress her butt for a while.
13. Partner A, massage Partner B's feet but use your whole hand so it doesn't tickle.
14. Partner A, stroke Partner B's body ever so softly with your fingertips.
15. Partner A, give Partner B a sensual massage.
16. Partner A, fondle two of Partner B's body parts at the same time.
17. Partner A, hug Partner B's butt. Don't rush, make it really sensual.
18. Partner A, massage Partner B's thighs for 20s.
19. Partner A and Partner B, press up against each other and stroke each other's butts.

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