Introducing anal play to a relationship

Connie asked:

My boyfriend and I are having trouble with anal sex. We have both done it before with other partners (me only once before) but for some reason we can’t seem to nail it together. We’re both enthusiastic to try it out with one another so you can see how distressing this is! I was reading that a good way to “ease into it” was to use buttplugs … What’s your advice for this kind of situation? I’ve read the 10 Rules and the Anal Play articles you have posted but there isn’t anything specific about the use of buttplugs – only hygiene and trust related advice.

Advice Grrl answered:

Hi Connie,

Partners, anal play and buttplugs can all take a while to come together and work successfully – although I entirely understand wanting to work it into your repertoire, because it’s a whole lot of fun once it does!  So, here are some specifics for you. Some may sound like repeats, but they are all vital, I promise:

  • Take it very slowly. Always use lots of lubricant, and reapply liberally. You really cannot use too much lube.
  • If you are more comfortable with having had an enema or douche first, there’s nothing wrong with that. It isn’t essential, but may help you feel more relaxed during play.
  • Make sure you’ve been to the bathroom first!
  • For the first few times you are playing anally (whether your bottom or his), only use fingers to tease the area. Touch around the outside of the anus, circling the pucker. Tease the opening. Enter a little way – gently – and let the area get used to the intrusion. Make sure your nails are short and smooth. Wear gloves if you’re more comfortable with this. You can apply lubricant both to the anal area and to your fingers/hands.
  • Pay attention to the reactions of the partner whose bottom is being played with. Ask for verbal feedback if you’re not getting enough information from bodily reactions.
  • Move slowly. Anything you insert, insert slowly. Anything you remove, remove slowly. If you’re turning a finger or a toy inside the anus, turn it slowly. There are a lot of nerves in the anal area (only the clitoris has more) and they will all be sensitized by this.
When you feel ready to move onto buttplugs, experimenting with a partner is definitely easier than playing solo. However you may wish to experiment on your own to get used to the sensations. There is nothing wrong with either approach.
  • Always ensure that you choose a buttplug that has a flared (wide) base. This is essential, as the intestines are not a closed system – you do not want to lose a toy up there!
  • Use lots of lubricant. Apply primarily to the tip of the buttplug, circling down to the toy. Don’t apply it to the base, as you need to be able to hold onto it.
  • Cover the toy with a condom if this makes you more comfortable. However if the plug is made of medical-grade silicone or glass it is able to be sterilised.
  • You may need to experiment with positions. This can vary from person to person and from toy to toy. The most simple are on hands and knees with the rump in the air, and on the back with knees raised (sometimes with a pillow beneath the upper bottom).
  • Again, be sure to communicate. You will need to work together to get the correct angle of insertion (often it’s not possible to see what you’re doing at this point)!
  • Insert slowly. Different plugs are shaped differently – but the majority are slim are the tip and then increase in size. So begin with minimal insertion.
  • Move at the speed that the partner being penetrated is comfortable with.  Deep breathing combined with gentle pressure may helpful for easing the plug in.
  • Once the plug is in, the penetrated partner may feel like they need to do a bowel movement. Having been to the bathroom prior to play (and/or had an enema) will reduce the stress at this point. If the feeling persists, however, or is particularly strong, it may be a good idea to remove the plug and go to the bathroom.
  • If/when they want the plug removed, or pulled back, do so slowly.
  • Keep the lube handy, and reapply if the plug starts to stick, or not move as easily.
The anus does not retain the stretching it receives from play, so each time you approach anal play you will need to warm up again. That means fingers, small toys, and then moving on to larger toys or body parts if you so wish.
And of course, the main things to keep in mind is that this should be fun, should not hurt, and should be a great experience for the both of you!

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