Have him give himself enemas. Use lots of lube. Start opening his anus with your fingers and then proceed to butt plugs and dildos. Go slowly. Spanking is a good way to excite as well as relax him. Make a big deal of the moment when you start to penetrate his anus with the dildo. He’s losing his anal virginity, something a lot of men don’t have the courage to admit they want. Be loving but firm and make it pleasant and memorable for both of you.
I edited this image from the comic book Hilda by Hugdebert, so I’m posting it fresh. (Besides cropping, I added the wrinkles to the guy’s asshole!)
It’s so exciting to be exposed and vulnerable to your lover. She is looking right at your anus. She knows your secret desire and loves you for it.
The only thing as nice as having your lover lick your anus is licking hers.
Good girlfriends lick ass.
Something about this pic sets it apart. It’s partly the expression on her face, which seems to combine urgency, pleasure, and a delicious distress (that’s a big cock in her asshole). I like her intensity in sucking that cock. She exhibits every sign of wanting both her mouth and her rectum filled with hot cum.
It’s going to be a very long night ……..
I’m intrigued by that long, skinny, translucent vibrator on the left. I’m pretty tight so that’s the toy I’d want inside me. I’d love to feel it sliding, and the tip would feel fantastic against my prostate, especially if the vibrations are strong.
I like to see anal toy collections laid out like this, especially when the lady is in the picture.