Advice – I want to try anal, but cannot relax. [NSFW]

I’ll start this off by saying, my fiance is an ass lover. He is OBSESSED with my ass. It’s not large by any means but during sex he always compliments it, loves doggy because he loves to see my ass, likes when I wear leggings so he can rip them open and fuck me behind, told me that he loves when I sit on his face , etc.

He has been wanting to do serious anal for a long time, he has mentioned it before a lot and I am not opposed to it, I would love to be able to enjoy anal and be able to please him that way, however I cannot relax enough during it for it to feel good.

I like when he puts his fingers in my ass while doing PIV and it always feels good when he does it with a finger, but all the times we have attempted with his dick it just doesn’t feel good, it is painful as hell and I can’t relax. I don’t know why or how to make this better. We use TONS of lube when we try so lube is not the problem. I would love to be able to do anal with him and fulfill one of his fantasies but I just can’t do it.

I am looking for good tips to try and ease the process. We have talked about getting a butt plug and having him use his fingers and work a plug in and do PIV to see if it helps ease my butt, though I’m not sure if that will actually help? I think his size and being an anal “virgin” intimidates me.

I would also like to mention that I also can’t get over the feeling that it makes me feel like I need to poop, even after using the restroom beforehand and cleaning out I always have the “I need to poo sensation” when he puts his dick in.

Please leave me any advice, tips, or tricks.

Terry, Reddit.

Dear Terry,

A very common mistake among anal newbies is that you can go straight from little to no stimulation to penetration. This is a particularly dangerous myth because your sphincter is just not ready for that type of action without the proper warmup. When it comes to proper anal intercourse warmup, there are three major components.

The first component is lubrication. Some folks don’t know that an anus don’t self-lubricate the same way a vagina does. It sounds like this part you’ve already got down. But I think it’s also very important to consider multiple different types of lubes. Sex With Emily goes into great depths about the differences between silicone-, water-, and oil-based lubes that I think you should take a look at. In short, silicone-based lubes like Uberlube are more suitable for longer plays while water-based lubes like Lube Life are easier to clean up. If you find that you keep having to reapply lube, you might benefit from switching to a silicone-based lubes.

The second component is training. Not many folks know this, but sphincter is a muscle! And like any other muscle, you are going to need to work it out and stretch it out to make sure that you can have penetrative intercourse. You’ve already mentioned anal plugs, and I think that would be a great idea. But I would also suggest anal training sets like this set from Babeland or this set from Adam & Eve to start training your interior and exterior sphincter for penetrative play. These flared-base anal trainer sets are especially great because they vary in size. Depending on your fiance’s penis size, you should absolutely practice. It is also very important to keep in mind that silicone is not at all like flesh of the penis. So what I’ve found helpful is to warm up the trainer plugs in warm water or – even better – a partner’s mouth before lubing it up for penetrative play.

I’ll also mention here that you should never use an anal toy that doesn’t have a flared base. You wouldn’t want to have an awkward trip to the emergency room because you lost your plug in your butt, right?

The final and the most important component is play!

The more pressure you put on your anus to perform, the more difficult it is going to be to actually be in the mindset to have anal sex. If you find that anal sex is always in the context of PIV, it might be beneficial to temporarily dock PIV so that you can enjoy anal play that doesn’t immediately involve genital penetration. You mentioned that you’ve enjoyed digital stimulation from your partner. So incorporating more of that into your sex life without his penis being in the equation at all should help you get more comfortable with anal play in general.

Just take it a bit slower.

I also want to touch on being an anal virgin. Our culture already has such a weird and warped standards around virginity as is. And often times, it is incorrectly associated with purity and sanctity. We don’t need to take those toxic beliefs forward in our relationships today. A lot of folks misunderstand that virginity is not a physical aspect you lose when you have penetrative intercourse with your reproductive organs. Instead, it might be more beneficial for you to reflect on your virginity as a spectrum, rather than a binary. You’ve already had your fiance’s finger in your ass. And in that specific way, you are no longer an anal virgin in the same way that having anal sex as a “God’s Loophole” doesn’t make you a virgin either.

As for the “needing to poop” sensation, that is also natural! It’s your body’s way to expel that which don’t naturally belong in your rectum, which in your case is your fiance. For your fiance, that generally translates to a gripping sensation that should provide an intense pleasure for him through his penis. For you, that “needing to poop” sensation is one directional – out of your ass. But practicing with the trainers and his fingers should definitely help with managing that reflex in the context of anal sex. Your brain just needs a little help rewiring the sensation from anal stimulation as something other than poop-oriented, that’s all.

Good luck!

Tea Time with Tomato is an informative relationship and sex advice column for both monogamous and polyamorous folks. By submitting your post, you agree to let me use your story in part or in full. You also agree to let me edit or elaborate for clarity.

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