DW, Id just wear a condom.
I would not risk myself by entering in unknown unprepared channels
I will tell you a case, which is called:
an introduction to anal by Jose
When I was about 19, I had a very cute girlfriend, smooth and balanced facial features, slim, small breasts, butt positioned in a negative angle with relation to the back (in this coordinate axis, shit exit sets the positive direction).
She lost her virginity with me and she was very ashamed of her body in the beginning of our sexual life. She was thinking she was too skinny but that is exactly my preference. I am also an ironing board type of person, by the way, kind of an androgynous one.
To me, she was perfect, it was hard for her to get used to vaginal sex, so tight, while my penis is a mighty powerful wagon. On the other hand, I’m a gentleman, very loving, and I wanted to print myself forever in the memory of that sweet girl by being the best that I could be. This meant that everything was about her, to give her pleasure, regardless of mine.
During days, I stayed grooming her, being a kitten, licking her with love, and exercising her with my fingers, stretching the muscles, building her self-esteem by telling and showing her how beautiful she was and how she was driving me crazy, which she could literally prove by sucking my hard dick. When an ardent girl discovers the pleasures of life, she becomes a mettlesome nymphet.
Whenever we got together, she begged to be penetrated, she wanted to be mine, be possessed, no longer a girl but now a woman. Her face when my dick touched her vagina, priceless, transfigured eyes, needing an exorcism. In the first times, only the head of my penis was entering, an unyielding virginity, hard to break through it, but who needs to hurry? With patience and love, everything can be eventually solved.
Abbreviating, this angel, this previous God’s soldier, this divine trumpet player, became the wildest horsewoman, a Devil’s soldier, wanting to sin, wanting to loop my neck, tie my arms, and use my body for her pleasure, suffocating me while seated on my face, drowning me into her majestic liquid that dripped from her fruit. Screaming Oh jose, Oh jose, Oh jose, makes me yours, please!
The next step was naturally anal sex…