I’ve been with a number of men and women and done a lot of the basics. Here are some items on my list going forward:

Get fucked by a real BBC.

Suck 5-10 cocks at a glory hole and swallow all their loads.

Have at least 4 guys fuck me in a gangbang, preferably without condom, leaving their loads in me.

Spend a whole weekend, maybe a week, as a man’s sissy girlfriend, in chastity or at least not allowed to cum.

Be a dominant woman’s sissy maid for a some extended time (minimum three days).

Have a sissy/trans girlfriend, ideally new to it, and I train them.

I perform creampie cleanup for a woman/couple.

Get fucked as a sissy in an alley or gangway.

Be a cuckold sissy maid/attendant for my partner as she gets fucked by a dominant bull.

Have a dominant woman give me a gloved handjob while I’m restrained and then she ruins it, possibly onto her boot/shoe for me to lick up.

Have a true sissygasm, even better if from sex with a man, or woman with strap on.

Spend a weekend away in another city crossdressed the entire time, including going out for dinner, bars, swimming, spa.

Be a sissy whore for a trucker and get fucked in his sleeper cab.

Be a submissive for a MF couple, going down on her while he fucks me from behind, or going down on him while she fucks me from behind with a strapon.