Cuckoldest

Cuckoldest Review

Cuckoldest features experienced, older swinger couples or solo women playing with younger men in their twenties in MMF situations. Since our last review in 2022, we've returned to see what's changed, and if the site has been updating with new content. The name itself may sound unusual—cuckold isn't a word you hear every day—so here's a quick refresher. In Renaissance and Shakespearean times, a cuckold was a man unaware his wife was cheating. In porn, however, the man is usually well aware because he's watching another man fuck his wife. He's often not allowed to participate, which can be a source of humiliation. But cuckolding can also be about the thrill of watching, and the scenes on Cuckoldest generally lean into this latter theme.

The younger men playing the virile studs are a variety of well-known Czech performers from the gay porn scene. Blond Chris Hollander appears in most of the scenes. He's a good looking, 27-year-old stud with a muscled body and a good-sized, uncut cock. Hollander is joined by fellow Czech hunks Pavel Sora, John Barber, Martin Dajnar, Ryan Cage, and Ivo Kerk. The older men and grandpas are not credited, but they appear to be in their fifties and sixties, some in decent shape while others are sporting some middle-aged spread. The women are a mix of types and appear between their thirties through fifties, and some are in decent shape while others are chubby. In a few of the more recent updates, the husbands or wives or both are in their early thirties and are joined by a man of a similar age.

The action is mostly MMF threeways while a few are larger groups. Seven of the early scenes feature two younger guys sharing an older woman. The guys suck each other's cocks and there's some pussy eating (but not a lot), then the guys fuck the woman and often one another. The newer scenes feature a younger guy playing with a much older man and woman. I wouldn't classify these as cuckolding as the older men actually help service the younger guys. I didn't see the older men doing any fucking, although a couple of them did get fucked. Some of the latest episodes have four to six people licking and fucking.

The scenes are mostly filmed in a sort of sex club / bath house where couples rent rooms to explore their sexual fantasies. In one scene called "Having Fun with Dirty Grandpa", they do it all. Blond guy Chris Hollander arrives and is directed to an older woman's room. She sucks his cock while an older grandpa stands in the hallway watching. He finally joins them, and the trio head for the couch while the older man sucks the younger guy's cock. After some more head from the woman, the pair of men spit roast her. Chris also fucks the man's ass before the couple take turns sucking the blond's cock. Chris jacks himself off and the man gobbles up his cum load.

Cuckoldest now offers 91 exclusive videos in MP4 format. They can be streamed or downloaded in 2160p (4K, Ultra HD), 1080p (Full HD), 720p (HD), and 540p (SD), with overall good quality. Some scenes are a bit on the dim side, but most look solid. The 4K files are very large—over 5 GB each—so if you’re on a slower connection or using an older computer, you may prefer streaming or downloading the 1080p or 720p versions.

All but one of the videos come with a picture set. These sets offer digital stills sized at a whopping 2667x4000 but shown smaller in your browser or on your monitor at good amateur quality. If you expand the pics to their full size, the quality isn't as good, but since these pics are so big, you wouldn't be able to see the entire pics at full screen. You can download pic sets in zip files or save your favorite pictures individually, and both slideshows and pic-to-pic navigation is available.

When it comes to updates, Cuckoldest has clearly grown since our last review. Back in July 2022 the site had 36 videos, and now in September 2025 it offers 91. That's 55 new scenes added over about 38 months, which works out to an average of roughly 1–2 new videos per month. Looking at the dates on the content, the site generally seems to add two updates per month, though the pace can vary slightly.

Cuckoldest members get access to a massive porn network with 152 sites and over 32,000 videos. There are tons of straight sites including some that feature older men or mature women like Dirty Gunther, Granddad, Grandmam, and Mature Van. There's also a good-sized gay porn network, Cockin, with several gay sites including Club Bang Boys, Raw Euro, Manalized, Man Up Films and more.

There are some issues. There's a pre-checked offer on the billing page, although it's easy to uncheck. The membership prices are only given in Euros, and neither the join nor the billing page mention if the memberships recur, although the site terms say that they do. By joining the site, you automatically agree to receive commercial emails with no way to opt out when you join. When I logged in, I was hit with a pop-over, but it was easy enough to close.

But possibly the biggest problem with this network is organization and navigation. If you get lost in the network, which is easy to do, click STUDIOS at the top of any page and look for Cuckoldest. Or you can browse all the sites, which they call studios, from there. They push their live cam chat network called Secret Friends. While you can browse the chat, having much fun is going to require you buy tokens.

Cuckoldest offers some scenes with horny older men joining in as their mature and horny wives have sex with a younger guy while the older videos offer daddies and grandpas watching as their wives get fucked by two studs in their twenties. And a few of the newest vids offer husbands and wives in their thirties getting it on with another man or in a group. There are 91 exclusive videos to download and stream on your desktop and mobiles, and there are pic sets, too. Updates are irregular, but most months the site adds one to two videos. And you'll find several sites among the 150+ sites that features older men with younger women or mature women with younger men. You'll also want to check out the bisexual, trans, and gay-sex sites in the network, and if you're looking for straight porn, you'll find plenty of that here.

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