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Stephanie May

Shown First Here
Stephanie May
  • Stephanie May is a small-town Ontario country cutie, but don't expect her to take that horse of yours for a ride, because under that cute cowgirl exterior is one hell of a sadistic and dominant trans top. She's been quickly making a name for herself among submissive men and needy tgirl bottoms since moving to Montreal four years ago, and all it takes is one look into her snake eyes and that beautiful cock of her's to see why. As one of Monteal's most intimidating and desired trans tops, her phone is constantly buzzing with subby bottoms desperate to get penetrated and bred. We can't wait to have her back here to bend over one of her favourite tgirl whores so she can really show us what she's made of. From what we've heard, this girl definitely knows how to chew you up, spit you out, and have you on your knees crawling back to her for more.

Stephanie's Scenes

Rating: 5.00

Lazying On A Sunday Afternoon

Stephanie May looks very happy to trade the usual indoor setup for a little sunshine. She settles onto the outdoor couch in a tight dress and brown boots, with the wind playing havoc with everything except her mood. Stephanie’s been keeping herself busy lately — and by busy, I mean getting dicked properly down — so this quieter solo set feels almost like a day off. A bit of sun, a bit of breeze, and Stephanie taking care of herself on the couch. Honestly, that sounds like a pretty good Sunday afternoon to me.

29th Sep 2026

  
16:05 HD Video
& 150 Photos
Rating: 4.67

A Return From Stephanie

Stephanie disappears for more than two years, then strolls back in wearing pants that look like fashion lost a bet. And somehow, she pulls them off. The tatted body, the nice cock, the confidence — all still there, only now with a comeback look that feels impossible to ignore. She has that same easy presence in front of the camera, like the gap between sets was barely a weekend. Some returns are polished. Stephanie’s is weird, sexy, memorable, and honestly much better for it.

15th Sep 2026

  
15:33 HD Video
& 167 Photos
Rating: 4.86

More May!

Stephanie May returns and continues her theme of unusual outfits and matching makeup. There is a bit of a French feel to this, which is appropriate considering she's from Quebec - with the black and white striped top, and sexy black fishnets. May is super excited to be in front of Vee's camera and her cock is hard and throbbing, and she needs to keep stroking it, while showing off the rest of that soft, smooth body with the budding boobs and hard nipples, and sweet ass with smooth hole. Another sexy shoot of this Canadian cutie.

6th Feb 2024

  
18:35 HD Video
& 120 Photos
Rating: 4.50

Canadian Cowgirl!

Stephanie May is our debut model this week. This 30-something Quebecer has a unique look and vibe about her, with a large tattoo across her smooth tummy and chest, her enlarged nipples left bare, as well as a number of smaller tatts and she's in her cowgirl model for this scene. Stephanie's bright red lips stand out against her otherwise pale skin, and jet black hair, the black Stetson crowning her and making the image complete. Fully naked we get to see what a great body Stephanie has, the boobs are budding nicely and her cock is smooth and hard, pink and ready for play. A nice debut shoot from Vee.

23rd Jan 2024

  
19:45 HD Video
& 110 Photos

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