Did you practice anal on your own or were you thrown in the deep water and had to swim on your own the first time you had anal with a partner?
First time my girlfriend coaxed me for a few days before letting her fuck me with her strap on. Immediately after that she began coaxing me to let a guy fuck me. At that time I had recently, during an MMF threesome, touched and sucked another mans cock. Before that I didn't have thoughts of anal, now I think about it a lot
I had played with myself from a very early age. I never had the real thing until my mid 30's during a mfm experience. Nothing I had done prior prepared me for it. He surprised me that night, and even though I wasn't expecting it, I let him do it. I felt him come up behind me, and pushed on my ass with his cock. I freaked out in my head, but let him continue. I was fucking a woman when he shoved his cock in me with no warning. He wasn't really gentle, and it did hurt at first. After a few balls deep pumps, it started to feel good...then it felt great...then I came all over the woman that we were sharing. She watched him fuck me. I had an orgasm after I had already cum from my cock. He got excited when he saw me cum, and fucked me hard for a good 10 minutes. I felt him swell, and heard his moans as he filled me with cum. We kicked back for an hour or so, and I gave him my first blowjob before he left.
After my first anal/prostate orgasm there was no looking back. I knew it felt out of this world and went from a finger in my ass and dildos, getting bigger all of the time. My wifes asshole was offf limits, but she had no problem putting something up my ass.What started with her original White hard plastic vibrator, developed to larger , smooth dildos to life like silicone cocks, to the anal explorer and Manhandler dildos. Bouncing off a suction cup dildo in the shower is a regular thing. My wife just calls me a big anal slut that will do anything to get fucked. She's right. Whats not to like? Its like taking physical sexual pleasure into another dimension.
I never practiced on my own, but neither was I thrown into deep water the first time, my first time was as gentle as it could possibly be with plenty of lube by someone who really cared for me. That person progressed anal sex with me each time until I could eventually take a good pounding and both giving and receiving anal became a regular part of sex.
The first time for me was with a much older mature woman. I was a young lad at the time and the tightness around my cock was immense, she had a great ass. The second time was with a lovely looking Indian girl, when I entered her she said it felt uncomfortable and that I was very big. I went with her for a couple of months we slept together and I lubed up before I fucked her. She never felt comfortable but for me it was amazing .
She does it for me because I need the prostate stimulation and physical release of an intense orgasm. Not as much as I would like, especially if I have a friend around. She would much rather watch me suck and fuck a good friend.
My wife was forced to take it anally in college, and that was her one and only experience. It will never happen again.
My fwb has been with dozens of men but had only one anal partner so we started off with anal beads well lubricanted and then I entered her. She was so tight but she took it and came as I used a vibrator on her clit. Now we sometimes use a vibrating dildo in her as well. My fb who is bi loves anal and just a little lube and I enter her with ease
It took us several minutes before I could get most of my penis in. Keep in mind, I'm intact, so that helped a little. I fingered her, lubed her hole and took my time. Btw it was her idea. Once I got past the head, I could push till I was in all the way, then humped SLOWLY and not all the way out. Please don't think I'm hung - just normal.
