>> How to decide if you enjoy bottoming. Anyone with experience on how it was the first time?
Am trans. I don't know how you CAN'T enjoy being bottomed.
Your prostate is up there. If you pay xlose attention to your body while your penis is being stimulated, you can feel that the best part of the feeling as you approach climax is actually coming from your prostate. But you're only getting like 10% of it. Getting bottomed is stimulating your prostate directly, the entire time. It's like trading in a sparkler for a fireworks show. If your hitting the prostate, then you are getting that really good "right before climax" feeling the entire time.
Also, the anus stretching feels good. In and out of the rectum feels good. Going deeper past your prostate feels good too. You get lots of good feelings all at once. Different positions get different feelings depending on what's being hit or rubbed against. On good days these feelings can travel all over your body.
The first few times you have something up there, your body is going to think you have to go to the bathroom. You'll get over that after awhile. Your body will have to learn the difference between having to go, and taking something. :)
Just clean everything out with your shower hose first until the water coming out is clear. There are fiber supplements you can use to make this easier. Don't go anywhere for an hour, because what goes up must come down and you don't want water running down your leg while you're in line at store. :P
The less you eat, the longer you stay clean. When I was eating one meal all day I was clean for a day at a time. I'd just do my business in the morning and clean out in the shower, and I'd still be good after working a twelve hour shift. When I'm snacking all day, or eating 3 meals, not so much. Common sense.
If someone else is going to top you, instead of using a toy on yourself, it helps to prep beforehand. Be clean and use a plug to stay stretched. It also helps your partner if you've gotten over your body thinking you have to use the bathroom as mentioned above.
There's nothing painful about it unless you are doing something horribly wrong, like going in dry and/or with a big object too soon. And it's not dirty unless you are. You wouldn't kiss a woman with a mouth full of bile or vomit. We brush our teeth and use mouthwash every day to keep that hole clean. Stay clean down there and you'll be fine. The cleaner you are in general, the easier it gets to prep. Also, life feels nicer in general when you're clean and empty up there!
>> How did you get to the point where you could cum from bottoming?
If you go at it long enough, and you're doing it right, AND you didn't already nut, you will cum. You can cum again later too if you have any left, and just keep going. And you might just pre-cum. You might not cum at the first orgasm, but how many orgasms you have is up to you. It never stops feeling good until you aren't lubed (getting sore), or you are just too tired. It feels better the longer you go because you start to swell up and get even MORE sensitive. Then the feeling can last for hours after because your swollen insides are rubbing against each other.