Strap-On for Beginners: Positions and Games

Strap-On Truth or Dare

Talk about it first, then try it.

Play “Strap-On Truth or Dare” →

Truths

1. Have you ever fantasised about being pegged?
2. Which position would you want to try first?
3. What makes you nervous about it?
4. Would you rather be slow and gentle or be told what to do?
5. What size would you start with?
6. What would you like her to say while she does it?
7. What is the first thing that comes to mind when you think of a strap-on?
8. Would you rather she take control or you guide her?
9. Have you ever explored with a finger or a toy alone?
10. What would make you feel safest the first time?
11. Do you want to watch in a mirror?
12. Would you rather she be dressed or naked?
13. What do you want her to do with her hands while she’s behind you?
14. Do you want to be stroked during it?
15. Which would turn you on more: begging for it or being told to take it?
16. What do you think it feels like for her?
17. What warm-up would you like most?
18. Have you ever watched pegging porn? What did you like?
19. What would you call her during it?
20. Would you rather be face up or face down?
21. What would you want for aftercare?
22. What do you think would surprise you most?
23. Would you want to try it again the same night?
24. Which of your fantasies would she enjoy most?
25. What harness or toy colour would you choose?
26. Do you want her to talk dirty or stay quiet?
27. What is one thing that would make you say stop?
28. How do you think it will change how you see her?
29. Do you want to plan it or have her surprise you?
30. If you had to describe the experience you want in one word?

Dares

1. Let her put a finger in for one minute
2. Help her put on the harness
3. Use your mouth on the strap-on for 30 seconds
4. Kneel and ask her nicely
5. Lie face down and let her massage your back and bottom
6. Ride the strap-on for one minute
7. Let her tease you with lube and fingers for two minutes
8. Bend over the bed and wait for her
9. Wear a small plug until your next turn
10. Let her grind against you with the strap-on
11. Say exactly what you want her to do
12. Hold eye contact while she enters slowly
13. Let her set the pace for one minute, no complaints
14. Stroke yourself while she watches
15. Kiss her while she holds the strap-on
16. Let her guide your hips
17. Get on all fours for 30 seconds
18. Let her spank you while you ride
19. Thank her after each slow thrust for one minute
20. Ask her for more, out loud
21. Let her blindfold you for the next round
22. Lie back with your legs up for her
23. Let her use a vibrator on you at the same time
24. Tell her how it feels, in detail, while it happens
25. Spoon with the strap-on in for one minute, no moving
26. Kiss her neck while she’s behind you
27. Let her put the cock ring on you
28. Beg her not to stop
29. Let her choose the next position
30. Pick a dare for her, she must do it with the strap-on on

Strap-On Positions Deck

Positions that work well with a strap-on. Skip any that don’t feel right.

Play “Strap-On Positions Deck” →

1. Classic: He is on all fours, she kneels behind. Easy to control depth.
2. Face to Face: He lies on his back with a pillow under the hips, legs up. Kiss while you move.
3. His Ride: She lies back, he lowers himself on top and controls everything.
4. Reverse Ride: Same as his ride, facing away. She can reach around.
5. Spoons: Both on your sides. Slow, close and very gentle. Good for beginners.
6. Flat Out: He lies face down, a pillow under his hips. She lies over him.
7. Standing: He bends over the bed, she stands. Needs a good height match.
8. Chair: She sits on a sturdy chair, he sits on her lap facing away.

Strap-On Dice

For couples who peg or want to start. Warm up generously, the receiver sets the pace.

Play “Strap-On Dice” →

Warm-up

1. Long back massage
2. Oral
3. Fingers, slowly
4. Small plug first
5. Rimming
6. Vibrator outside
7. Kissing while she straps in
8. Receiver’s choice

Position

1. On all fours
2. On his back, legs up
3. Spooning
4. He rides
5. Face down, pillow under hips
6. Standing, bent over the bed
7. Edge of the bed
8. Kneeling, facing a mirror

Pace

1. Barely moving
2. Slow and deep
3. Steady
4. Faster when he asks
5. Stop and start
6. He moves, she stays still
7. Grinding, no thrusting
8. Only shallow
9. Deep and still
10. He begs for each thrust

Extra

1. She strokes him
2. Hands tied
3. Dirty talk
4. Cock ring on
5. He touches himself
6. Eye contact
7. Slow kisses on his back
8. Nothing else
9. Plug for her too
10. She pulls his hair
11. Spanks
12. Wand on her

For

1. 2 minutes
2. 5 minutes
3. 10 minutes
4. One song
5. Until he begs
6. Until someone finishes

Finish

1. He finishes during
2. She finishes first, with a toy
3. Both
4. Nobody yet
5. Hands-free attempt
6. She decides