How Not To Lose A Sports Bet

They say “when you’re in a hole, stop digging” and the same goes for doubling down on a losing bet, I do believe:

naked woman bound in a helpless position to a baseball bat and menaced with two dildos

The speech bubble caption reads “When I said double or nothing, this isn’t exactly what I had in mind!”

Elsewhere on Bondage Blog:

Rope Bondage Plaything

This reluctant rope bondage plaything is (I think) a screenshot or publicity still from a Japanese movie, as seen in Seijin Eiga #84, a Japanese magazine from January 1973.

worried looking japanese woman in rope harness being toyed with by two japanese men

Elsewhere on Bondage Blog:

Sadistic Bondage Anal

Nobody but a sadist draws a cock that large doing a dry-ish anal insertion unless pain (for her) is the point of the game, right? At which point, putting a steel clothespin on her clit is, what, gilding the lily? Adding insult to injury? I’m not sure of the correct metaphor, but it does seem almost gratuitous:

huge cock going up an ass where it looks to be a very tight fit

Artist is Kamitora.

Elsewhere on Bondage Blog:

Punishment Cage

This cage, quite simply, is too small to put a person in for more than an hour or two. There’s no way to settle comfortably in that space. Would it work as a punishment? Absolutely! But care must be taken with timing, to preserve the line between “fits the crime” and “unreasonably cruel.”

woman wearing shackles inside a small heavy steel cage

The photo is from Simply Restraints, a site that’s been gone since about 2018.

Elsewhere on Bondage Blog:

Three, Ready For Doggy

These three gagged women are on their knees and chained by the neck to a convenient steel bar. The doggystyle bondage sex party can start at any time:

three women chained for slave service

I recognize the venue as a Kink.com set, but I don’t have a site/channel/shoot ID.

Elsewhere on Bondage Blog:

Bondage Toilet Stall Blowjob

Rope bondage and a blowjob in a doorless toilet stall — that’s pretty squalid, and squalid can be hot:

toilet stall bondage blowjob

Photo is from Chanta Rose’s old Twisted Factory Fucked And Bound site.

Elsewhere on Bondage Blog:

Old School Bondage Brunette

This vintage brunette in rope bondage and a sheer negligee and stockings is in the style of the mail order bondage photos of the Irving Klaw era, but I have no idea of this photo’s actual source.

vintage bondage woman on a bed with hands and wrists tied

Via Vintage Lust.

Elsewhere on Bondage Blog: