I'm reposting this from a response to another comment. Here's some instructions to having anal orgasms if you're not experienced enough.

To start off, don't force it, if you don't have enough experience you really cannot force it even if you want.

What you wanna try is abstain from cumming for a few days (3-5) to let your prostate build up enough cum and swell a little, making it more sensitive; and when you do anal, just enjoy yourself for a little while (like 30 of playing with your butt) and obviously do not touch your clitty, you want ALL of the pleasure to be focused on your ass, or well most, the rest could be in your body, but not on your clitty.

If you haven't came by then and you wanna cum soon (if you don't wanna cum yet then by all means just keep playing :P), then I'd suggest changing to a strong pleasure position, my favorite is laying on my side, but prone is also really good, and missionary with your legs up and crossed while you hold them to your chest, is also incredibly strong.

If you lay on your side, I'd recommend you start with your legs at a decent angle (70°-110°), close together, and just fuck yourself at a regular pace aiming at your p-spot for a few minutes (like 5 , don't rush it), once you feel enough pressure built up, ignore it a bit and just keep going at the same pace for a few more minutes, maybe just slightly faster and harder.

Once you can't take it anymore, I recommend adjusting your legs to a steeper angle (150°-180°) and fucking yourself faster and harder at a steady pace, increasing a little bit as you go on, and also clenching. Something very important is that you shouldn't strain yourself, if you overextend, your arm or ass will get tired and you will lose the orgasm, that's why maintaining a steady pace is crucial. If you know your limits, just stick to them and you'll cum pretty easily.

If you follow these instructions correctly, then you're guaranteed to have an anal orgasm (I would know, this is how I used to cum all the time before I mastered how to please my asspussy, lol).

Though if it still doesn't work, there's one way to 100% cum without fail, and it's this video: [Go Fuck Youself] in Xhamster, it's a dildo hero that lasts for like 2 hours and uses a lot of ass-grip changes and a bunch of dildo techniques. There is absolutely no way you do not cum by playing it, even I with all of my experience could only last 45ish minutes before I came, and I was actively trying and forcing myself not to cum!

Hopefully this post helps you achieve your first sissygasm if you've never had one, or helps you be more consistent at them going forward! If you have any doubts or anything, I will be checking all comments, anal sluts gotta help each other!

Edit: Added some links!

Edit 2: Since I tend to link this guide some other stuff, I figure I'd bundle them better. Here's a comment with an anecdote, with a link to more anecdotes and advice, it's a bit spaghetti, but feel free to check it if you need more guidance https://www.reddit.com/r/Sissy/comments/t2g495/building\_stamina/hymfjcf/?utm\_source=share&utm\_medium=web2x&context=3