Update: We tried this and aside from a few missteps it was absolutely amazing.

This is a task or scene for any BDSM couple interested in anal and anal play. It is also an excellent vanilla exercise (just remove the bonds) for anyone interested in anal training and play. Make sure to discuss this activity with your sub or partner first. If they agree, this is a great way to gauge interest and explore anal play.

If your sub or partner becomes uncomfortable, uses a safeword, or is in distress, STOP. LISTEN. You may have to soothe some fears or comfort them. You should not be upset if you need to stop or scrap the exercise entirely. This happens and it may be something you can table and explore further later but it can be overly stimulating or your sub or partner may just not like it.

If you are the submissive or bottom partner, then do not be afraid to say your safeword.

This is not the time to push limits or to punish your sub, it is a time to explore your sub or partner’s desire to engage in anal play.

I am kind of excited to try this one and will be adding a follow-up once we have. RU (my dominant) may also have something to add to it on all counts. I will make note of things to add in or leave out if you want this to be a bit more vanilla.

First and foremost, make sure this is safe, sane, and consensual play! I will be using sub but if you are doing this with a vanilla partner just replace sub with partner.

You do not have to follow this exactly, the important thing is to read the whole thing through before you try it and most of all…
HAVE FUN WITH IT – you can modify it to your play style and desires just as long as you stay within the confines of safe, sane,

Things you need

LUBE – the kind that is safe for the toys you play with – DO NOT FORGET THIS!!!!

Note: LUBE and you don’t want to use anything that will numb the area and prevent them from feeling if something is wrong. A lot of people recommend using a numbing lube but this is dangerous, pain is a way to tell you if something is wrong.

Things You May Want

Anal cleansing kit (for clean play)
Your favorite ties and anchors (rope, silk, leather, whatever you like)
Pillows (for propping up and better access)
Vibrator or Dildo (Female)
Cockring or Dildo (Male)
Small Anal Toy
Medium Anal Toy (only if your sub or partner is used to a medium toy)
Sensation Play Items (This can be anything from hands to floggers to feathers)

What to Do

1. Have your sub clean themselves (or you can clean them) with the anal cleansing kit if your sub’s agreeable you might want them to shave as well.
2. You can insert a dildo, cock ring, or vibrator now or wait until you have them positioned, or simply use your hands for stimulation.
3. Position your sub on their stomach with their hands and legs bound. Use a pillow or three under your subs stomach to make sure the area you want is exposed for you
4. Edge your sub or partner at least two times to make sure they are nice and ready
5. Check with your sub, check the bonds
6. Start on the outside using sensation play items, although you can do this for however long you want, I would suggest not more than 10 minutes. Take cues from your sub or partner to see when they are ready to move on. If your sub starts lo lose interest before the 10 minutes you might want to consider a shorter time between edgings
7. Check with your sub check their bonds
8. Edge your sub at least two more times. Don’t forget to excite yourself as well all throughout this process.
9. Move towards the inside not touching the anus continue with sensation play items but softer, these tissues are very sensitive and can be easily damaged. If your sub is new do not use any form of impact play here. Again take cues from your sub to make sure they are comfortable with things and not for more than 10 minutes. Make sure your sub is not ticklish while you are doing this.
10. Check with your sub, if bound do a circulation check.
11. Edge your sub again at least two more times, don’t forget yourself as well. add lube
12. Move to the anus and use your fingers to gently play with the opening.Take cues from your sub but do not do this too long. Your sub can get sore or you can scrape your sub with a fingernail creating an unpleasant experience for everyone.
13. Here you can edge your sub and play with their anus gradually increasing pressure without full penetration.
14. Check with your sub before inserting anything! If bound check circulation. add lube
15. Use a lube applicator or your fingers to work lube into your sub not just around the outside of the anus. Do this very slowly. If you think you are using too much lube double it. You ultimately want to be able to insert your finger or small toy into your sub with little resistance. If you think it is too much lube add more.
16. This is where you are going to need to get creative and watch your sub carefully. Once they are comfortable with the object or your finger, start to move slowly and carefully. You might want to make sure your sub stays excited by masturbating them if you can, or you can use a vibrator, dildo, or another favorite device.
17. Check your sub and check circulation add lube
18. You can let them cum with just a toy inserted or you can move onto a bigger toy or your penis (if you have one) ONLY if you’ve discussed this before you started.
19. After you both are satisfied or if your sub has asked you to stop, be sure to gently clean up your sub and provide any aftercare necessary.

Notes

• You can cum at any point during this exercise but you always want to make sure your sub cums at the end of this. You do after all have them spread out for your viewing pleasure. Remember the point of this is make anal play pleasurable and therefore exciting for both of you.
• It is extremely important that short of the person on the receiving end wanting to stop you follow this all the way through. You do not want this to be in any way a negative experience for the person receiving this. This exercise is designed to help increase interest in anal sex and make it a fun activity for BOTH of you. Stopping can cause a negative emotional reaction that may discourage anal play in the future.
• This will work no matter what kind of couple you are as long as you are both interested in anal sex.

Variations: