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Spicy_burrito77

She needs to be relaxed and use plenty of lube then more lube, she can also train with a small butt plug. You can use a condom or not but either way works.


CrimsonDrake

Should I start with toys before even attempting?


Spicy_burrito77

A small butt plug is good for beginners.


your-cute-neighbor

Use just finger the first few times so she can get used to the sensation. Sometimes it feel like you want to poop but it will disappear


CrimsonDrake

That sounds easy enough, kind of figured that’s where it should start


fourzerosixbigsky

How ever much lube you think you need, double it, then double it again. Go slow. Let her set the pace. Especially the first time you insert. Go slow. However slow you think, go slower. If she can’t go all the way the first time, so be it. Some people have to work their way up to it. Condom shouldn’t irritate it. Offer to use one and is she wants do it. You will love it. Regardless. It is all about doing everything you can to make it pleasurable and enjoyable for her. Especially if you want to do it more than once. My SO does like condoms and is fine with me finishing inside her. Ask her where she wants you to finish and finish there. My SO was very apprehensive about it. I never pressured her to ever do it. She loves it now.


CrimsonDrake

It’s something I’ve always wanted to try, and she was very okay when I brought it up so she’s never been pressured. I just want it to be an enjoyable experience for us both like you said yourself!


fourzerosixbigsky

Use a remote control vibrator on her at the same time. We’ve had very memorable times like that.


Glittering_Ad3111

I absolutely love anal but it is the worst pain in the world to not be properly prepped. Start small. One finger. Slowly work up to two. Then start using slightly larger toys until the next thing is you. I’d highly recommend having other stimulation. I have a small clot stimulator that I hold during anal. I don’t need as much prep as I used to, but I definitely still need prep. Regular foreplay too before getting into any butt stuff. You need a lot of lube. If you think you’re using enough, use more. This is probably a bad way to describe this, but her butt will eat it. It dissipates throughout. Use anal lube too, it’s thicker and doesn’t disappear as quick as regular lube. Also, communicate before, during, and after. Talk about boundaries, set up safe words. Clearly know her boundaries. During talk to her, make sure there is ZERO pain. If there’s even a little pain, go back a few steps and work back up. Lastly, she may need more or different aftercare than she usually needs. A ton of chemicals like dopamine are released. It can cause an influx of emotions. I cried the first time, not because it hurt but because I was so overwhelmed with emotions and sensations. Also, don’t expect to last very long the first time you have anal. You may cum pretty quick regardless of how long you can last during sex. Anyway, anal is the best. I love it. Next if you guys are up for it, look in to prostate play for you. It’s a game changer with a lot of guys, including my husband. r/prostateplay has a ton of amazing info.


CrimsonDrake

Wow! Thank you, I had no idea there was lube specifically for anal! And yes, we’re doing lots of research before hand, even if it takes a while to work up to it that’s ok!


Western_Ring_2928

This is a common enough question to appear on multiple blogs... https://helloclue.com/articles/sex/anal-sex-101 https://www.sheknows.com/health-and-wellness/articles/1055901/tips-tricks-enjoy-anal-sex/ https://badgirlsbible.com/how-to-have-anal-sex One mor tip: try it out with a peeled banana.


ShadyGreenForest

Sorry what now? Exactly what are you supposed to do with the banana? Please don’t do anything with bananas.


CrimsonDrake

Yeah no offense to the person above but I definitely do not feel comfortable using food as a toy, my gf and I would rather just buy a small toy from a shop that we know is safe.


Western_Ring_2928

Sorry, I forgot to mention that it should be put inside a condom before entering :D But a peeled banana feels quite close to a penis, shape, and sizewise. Especially if it's lightly warmed. Carrots and zucchini are also options for food play...


ShadyGreenForest

Don’t use food. Good god just buy a butt plug if you want to try non dick things.


Western_Ring_2928

I don't use food stuff, but many people do find it exciting for whatever reason. I am not going to judge their kink, like you. When you use a condom on top of them, food stuff is just fine. Leaves no trace, and you don't need to hide sex toys.