I've had several great sessions this way, usually loosely cupping my balls with my right hand as I hump the sheets. I did this a LOT in my teens, actually. When I feel like I'm about to cum, I try to catch the semen in my left hand but sometimes get some sheet drips. When that happens, I usually use a cold, damp cloth and rub those out soon after. I also have some nylon/fake silk sheets that are soft, smooth and slick as I writhe my naked bod around inside.
Are you reffering to bedding hanging outside on a clothesline or on a bed. If you are referring to bedding on a bed then no. If you are referring to bedding on a neighbor's clothesline then...maybe, I can't remember.
My preferred method of Prone Masturbation has always been to fold my quilt into 3 lengthwise, then roll it into a 'doughnut' form. You can then use the central hole as your 'vagina' However, bare skin against fabric is not advisable, as it can cause injury and/or long term numbing. A condom can provide a degree of protection or, as in my own case, push a FleshLight into the centre of the 'doughnut' & you're all set to hump away.
As a teen, I'd insert my prick between the bottom mattress and the top mattress, kneeling on the floor. Nice and tight, but the stains I made. Whoops. I think a lot has to do with the angle of your erection. Depends on if your a "straight out" dude or a "curvy." Seems like a curvy would have all the pressure on the head, whereas, like me, a straight out dick would get rubbed all around. Humm, sounds like an experimental science project.