First time

Finding the right guy is always the challenge, there are hook up sites, gay bars / clubs, saunas etc

preparation, a bit of self-training with toys (dildoes butt plugs), use of a douche

How does it feel ........... difficult to put words to it ..... butt once you have been fucked by another guy you'll just want more. The actual sensation is slight pain (not much) some pressure and then as he rides you sheer pleasure
 
I started with my fingers and a good lube. Be sure you learn how to clean out your ass before you do any anal play, even if it's with your self. Find a few objects or dildos and explore, see what hurts and what feels good. As I got older, I found places that men (tops and bottoms) love to visit, places like adult video stores with gloryholes and sex clubs with rooms and/pools with nude tanning. Being a petite, cute young Latino man, not very masculine looking....it wasn't difficult finding a man that wanted to fuck my ass. I am grateful that the first five or so were not well hung men. I would say they were about five to six inches in length and normal girth. It gave my ass a chance to be accepting of cock and a man that just kept pounding away in my ass, even those first five were slightly painful.

I was about twenty-one or so when I encountered my first large cock, married guy looking for a lil more than what he was getting at home. Probably a good 9 inches and thick as fuck. We needed lots of lube and patience, the pain was unbearable at first, I remember making loud whimpers, he had to cover my mouth. This went on for about five minutes before he started working it deeper and harder. After that my hole body had a rush of pleasure. Took him a good 30-40 minutes to shoot his load. From that point on, my ass was broken in, and any other big cock wasn't as hard to accept, even though this gentlemen and I developed a sexual relationship over a year or two, he broke my ass in real nice. I never had to worry about someone being too big for my ass.
 
The first time... I had been in a blo and go relationship with a guy for a couple of months. Went over one Thursday AM and he was sucking me. I felt his hand go between my ass cheeks and play a bit with my hole. I did not discourage him as he had fingered me before. He reaches over to the nightstand and get some lube. I thought he was just going to finger me some more. He is still sucking me when he pulls back gets between my legs and I see him lubing his cock and he gets two fingers in me. His cock is not thick but he has a good 7 inches. He raises my legs onto his shoulders and then I felt his cock enter me and then he was balls deep in me. It did not hurt unlike some since. He pumps his load in me and I cum all over my chest and stomach. It felt amazing. I knew I would keep doing it from that time on.