Sweetie, anal orgasm are way more difficult to reach but WOW it's an experience ! 2 things that helped me A LOT were:
- Weed (it is not for everyone but I would recommend give it a try): It helps relaxing and the stimuli from the hypnos seems WAAAY more intense (and your ass seems to take the dildo more naturally when you're stoned (a little bit like poppers). Weed gets me 100% in the mood to reach anal pleasure... it's really hard for me to reach it without being stoned because you have to give yourself fully to it.
- DO NOT touch your dick, simply forget it exists. Be fully focus in reaching pleasure from your butt. And enjoy the trip. Don't seek the orgasm itself, it will come naturally as you enjoy yourself.
- Be patient. Sometimes it takes hours (that's right HOURS !) to reach the anal orgasm but every second of it is worthy.
- You can get 2 types of anal orgasms : with or without cum(dry
orgasm). So if you don't cum (you shouldn't be searching to cum, FORGET
your dick !) you're actually lucky ! You can play for hours and have
many (dry) orgasms if you don't cum...and the horniness will build up
for the next time !
I think it's as much a mental process as it is a physical one, a vanilla straight male may not be used to being penetrated unless he has had a kinky girlfriend who perhaps probed his boi-pussy with her fingers etc.
If you can get relaxed enough and put yourself in a feminine mindset then with good lube and the right sized toy you should be able to have a very pleasant experience. I myself prefer to affix the toy to a surface and move my body back/forwards or up/down against it and leave my hands free but I did start with a regular hand held Dildo which happened to be too big for a tight ass noob so I would say don't go crazy with size if your new.
I think what you maybe should try is a prostate massager, they are shaped a little differently to a regular dildo to stimulate the prostate more. There are many sensitive nerve endings inside you and if you find the right spot then a repeated motion against these pleasure spots will eventually make you orgasm or at least bring you very close! . . I'm not sure if you remember the first time you learnt to masturbate? assuming you're not one of the lucky ones who's first orgasm was during sex then you may remember it was a strange learning curve . . I would say the same applies to anal for a straight male.
The good news is we now have the internet so it's possible to get advice from like-minded folks, back when I started there was no one I could learn from except the female shop assistant in Ann Summers where I was forced to shop in person, I'm pretty sure I tried to cover my tracks by saying I was buying it to use on my girlfriend but I think she figured it out :) . .
Panties & Tights (body stocking etc) really help change the male " mental process" into a more feminine mindset, along with being relaxed and horny, good anal lube, the right toy and the right sissy-hypno you will be very much wanting to be penetrated and feel that wonderful sensation from the constant motion against the nerves and prostate inside your boi-pussy . . good luck!