Shoesession

I think the least troublesome would be to get a discarded store dummy. Or one of those inflatable rubber companions. The last works very well as one fellow at this forum has proven. I used to put a paperweight or other heavy object in the foot area of the boot and a piece of stiff pasteboard folded three times lengthwise to keep the shaft full and upright. Usually the boots would stand up smartly without the tops flopping over. Then I could blast away.

i use old clothes to fill my boots and then i use a belt to keep them together

These are all pretty good tips! Now I just gotta make sure no one in the house sees my boot collection lol

I stuff them with those air pillows used for packaging sensitive goods

gumboots wrote: Wed Jul 24, 2019 8:41 am I stuff them with those air pillows used for packaging sensitive goods

Those air pillows rolled up and with a bit of oil added are rather nice to fuck on their own as well

It's still way better when my GF does it for me, right?

boot.perv wrote: Thu Sep 19, 2019 11:34 am It's still way better when my GF does it for me, right?

Yes, the girl has full control over things and with a bit of practice can make it an exquisite experience. A skilled operator should be able to have the guy writhing all over the place. Also she controls when the guy is going to 'come'.

Take them to a hooker / escort and have her boot job you to cum shot ending

The. See the owner of the boots in them soon after not knowing what you’ve done

Hey, a girl is always nice, but it was about giving a bj yourself...
Latest thing i did was cutting some plastic foam block into a foot/leg shape for stuffing and it was awesome! Especially when the foam is soft... wooohoo

Dr. Bootjob Cowboy presents: Fun With Boots

Tonight's episode: The Bruichladich Octomore Sigle Malt & Sorel Medina Bootleg

The smokiest whisky combined with one the best soles and heel for a bootjob!

Let's have some bootfun tonight! Yeeha!