"just the tip" is the first great challange, the first step, every bottom knows: there is no return...no matter how much it hurts,
I never played "just the tip". When I gave up my ass cherry, both me and the top knew I expected to be fucked before we met. I knew beforehand that once he started serious ass-play, it probably would not stop until he had finished inside me. I guess the final "point of no return" was when he positioned me, on my back with thighs open and knees bent. He had already rimmed and fingered me and worked lube into me. He crawled up along my body and pinned my body under his. That's when I knew, "I am going to be fucked by a man and inseminated with his sperm."
Then he kissed me. A long, deep kiss. I could feel his cock brushing against my pucker and I knew what it was going to do. But he kept kissing until I relaxed a little, then he started probing my hole and finally he pressed his cock firmly against my anus. As he increased the pressure, the discomfort also increased. I think I said "Ouch!" . . . . then "OUCH!!".
a real top will go deeper, hold still the first moment wenn he entered the head , than slow, but envenly entering, no matter the bottom is whining or complaning.
Yes, he was very controlled and deliberate as his erection urged my sphincter to yield. I don't think anybody automatically opens up on their very first time, which is one reason you feel the jab of pain when the cock pops through.
My anal muscles went into painful spasms when his cock broke through. He held both himself and my body in position, not moving. I know I tried to writhe away from the cock violating me, be his body held me down. My face scrunched up in a grimace, my legs kicked, and my hands clawed the sheets. I moaned in discomfort, and said "It HURTS!" but he didn't say or do anything. (Afterward he told me that almost every virgin says the same thing: "Ouch!", "OUCH!!", "It HURTS!".)
I was still spasming a little when he completed the insertion to full depth. For the next inch or two it felt strange - pleasurably strange - to fell something going the wrong way through my anus and sphincter. Then it started to hurt, not at the sphincter but deep inside me. Before he was all the way in I was crying . He never spoke or let up - just continued to take what he came for.