Dating My Stepson

“I’m Dating My Stepson” is something of a loaded phrase, and it’s going to elicit different responses depending on who’s speaking and who’s listening. It could be the stuff of daytime TV, some scandal for Dr. Phil to parade in front of his studio audience. You probably ain’t going to be happy if you hear it on a hookup app like Tinder, and you’d be even more upset if the words fell out of your wife’s mouth. On the other hand, if you’re a pervert looking for some family roleplay content to shake your dick at, those words might work like magic, turning soft, spongy flesh into raging hard wood.

You probably already guessed from the name, but yeah, DatingMyStepson.com is peddling premium taboo MILF pornos. The tagline calls it a “MILF Dating Reality Show,” adding a new twist to the usual scenarios we’ve all seen trotted out time and time again. I’m not saying there’s anything wrong with the classics, but who doesn’t appreciate a little variety? DatingMyStepson is a brand-new site, launched in September 2024, but I already had high hopes the moment I pulled up the tour page. Let me tell you all about it.

Dating My Stepson, Loving Your Mom

DatingMyStepson has all the sparkle and polish you expect from a high-end paysite launched in 2024. The pink on white color scheme and heart in the logo give the joint kind of a wholesome girly vibe, the kind you might expect from your mom, though the imagery itself is far from wholesome. There’s a MILF riding a lucky younger dude’s dong in the header graphic, and it only gets more explicit from there. Scrolling down the page, I’m met with thumbnail images of shapely stepmoms bending over, getting their pussies stuffed and slurping on sausage, cum dripping down those pretty faces.

Dating My Stepson is part of the MomLover network, which I’ve talked about here at ThePornDude a time or two. Membership currently includes access to 9 different mom-oriented taboo sites. The last time I looked, there were only 8 sites, and that was just a couple months ago. Most of these networks tend to keep expanding outward, so the number may be even higher by the time you take a peek for yourself.

Clearly, this ain’t the company’s first rodeo. That’s evident not only from the existence of those other sites on the network, but also from the quality of the material all over the tour page. The shots are all crystal clear, beautifully framed and well lit, and you can tell they sank some money into those flashy sets and setups.

There’s also the matter of casting. DatingMyStepson shoots with some truly gorgeous and talented pornstars, and there’s a good chance you’ll recognize some. Pristine Edge, Cassie Del Isla and Bunny Madison all showed up at their naughtiest during the site’s first month online. Other recent scenes on the MomLover network have featured girls like Penny Barber, Jennifer White and Skylar Snow. I even spotted Anya Olsen, Lauren Phillips, Jesse Pony and Armani Black, all of whom I’ve gotten to know quite well on the PornDudeCasting couch.

MomLover keeps it old-school with the perks, so unlike a lot of modern paysites, DatingMyStepson will let you watch some video previews for free. The sample of their debut flick, Massage and More, runs a good five and a half minutes. I know some of you cheapskates are just going to rub one out for free, but the preview got me in the mood for the full ticket. They ain’t kidding about the reality show setup. In this one, a gaggle of MILF pornstars are competing for the affection of a 24-year-old dude named Jimmy, who eats up the attention. What a lucky motherfucker—literally!

Join a Club of Real Motherfuckers

As part of a big-ass network, DatingMyStepson.com is already a better deal than your average one-off premium site. Because the site is so new, they’re also offering a launch sale as I type this up, so the whole thing is a few bucks cheaper than your average paysite. Discounts on longer memberships are even better than you usually find elsewhere, with a yearly rate breaking down to about seven bones a month.

If there’s just one disadvantage to the setup, it boils down to that ripe freshness I keep mentioning. Dating My Stepson was launched less than a month before this review, so there are currently only a handful of flicks with the branding. Releases for the imprint have been dropping at odd intervals; the first couple releases were nearly 2 weeks apart, while others have dropped on subsequent days. This ain’t uncommon on newer sites, as they’re probably stocking the shelves to get things in order.

Five videos alone would be a hard sell for $25, but remember, this is part of a network. MomLover sees multiple updates per week. In recent days, the membership has included new releases from Mom Wants Creampie, Bratty MILF, Mom Swapped and Mom Wants to Breed. If you’re into MILF movies, this is one of the better deals on the market. I’d say their only really direct competitor in this realm is MYLF, who also offer a hell of a MILF-based bang for your buck.

MYLF does have the advantage of having been around longer, which means they’ve had more time to build up their library. That said, MomLover has been at it since 2021, and their stash is nothing to sneeze at. It’s certainly something to cum to, though, with over 222 videos as of this writing. If you subscribe and still end up with blue balls, it’s probably something you should discuss with your doctor.

What Are You Doing to Your Stepson?

Even though there are just five videos to choose from currently, I still wasn’t sure where to begin my official fap test of Dating My Stepson. Every scene looked worthy of at least a handful of lube, so I figured I’d just jump in with the very latest movie on the site. Stepmoms Secret Confession stars the gorgeous Pristine Edge and runs a little over half an hour, which seemed like exactly the amount of time I wanted to spend shaking my dick at the screen.

After a quick network intro and DatingMyStepson.com logo, the video opens with a montage of talking pornstar heads before the lovely Miss Edge takes center stage. They sell the reality show gimmick so well that I wondered how much was scripted and how much was improv, which is honestly how the best reality shows make you feel. “The producers told me the twist of the show was that on the last show, I go on a date with someone your age,” she tells Jimmy, who happens to be her stepson.

The awkward family dynamics are interspersed with little interview snippets with Jimmy and the various pornstars involved. Pristine Edge cuts Jimmy’s chicken and feeds it to him while the other girls say stuff like, “Jimmy’s on a date with his stepmom? That’s kind of weird?” That sexy-ass weirdness really heats up around the 9-minute mark, when Jimmy’s stepmom pulls his dick out and slurps on it.

The production values are fucking stellar, perfectly straddling the line between reality TV and hardcore porno. There’s a vibe shift toward the latter half of that equation once the clothes start coming off, and the camerawork is incredible throughout. It’s kind of ironic: reality TV tends to feel more polished than reality porno, but the hardcore action here retains the multiple angles and steady handheld shots of the former. Suffice to say, I fucking love it!

The unique reality show setup of DatingMyStepson.com is worth a look if you’re into MILFs and want something a little different than the usual taboo scenarios. The membership might be a tough sell with just a handful of flicks currently available, but the inclusion of the full MomLover network makes this one of the better deals out there for fans of Mothers I’d Love to Fuck. The site’s got some of the longer free previews I’ve seen on a paysite lately, so I recommend starting there and seeing how you like the vibe.