https://www.429men.com/tags/shemale-date/ Thu 16 Apr 2026 13:15:43 +0200 https://www.429men.com/videos/305601/this-is-my-first-time-with-a-shemale-i-found-her-on-a-dating-site-jade-venus-spencer-bradley/
Spencer Bradley has always wanted to make it with a trans woman and finally builds up the courage to go for it via a dating site. Jade Venus has only had sex once with a cis female so this is kind of a new thing for both girls. The date went well and now Spencer finds herself back at Jade's place. When Jade comes back into the room wearing the sexiest lingerie and a stiff cock bulging out she is mesmerized. This is all she ever wanted in life. Immediately the two girls are all over each other and Spencer is slurping down Jade's gorgeous lady stick to the balls. Spencer's pussy is the perfect desert for Jade as she greedily slurps and licks it wet for her to start putting her hard dick into. Spencer comes over and over gazing into the eyes of the beautiful woman fucking her so well and eventually gets a huge facial of lady juice from Jade. What a date. It's everything Spencer imagined and more. ]]> Sun 22 Feb 2026 02:38:43 +0200 https://www.429men.com/videos/305601/this-is-my-first-time-with-a-shemale-i-found-her-on-a-dating-site-jade-venus-spencer-bradley/ https://www.429men.com/videos/381674/chad-has-special-needs-and-finally-finds-a-date/
TS Casey Kisses goes on a blind date with Chad Diamond, and is thrilled when he wants nothing more than to see her cum ]]> Thu 19 Feb 2026 22:46:26 +0200 https://www.429men.com/videos/381674/chad-has-special-needs-and-finally-finds-a-date/ https://www.429men.com/videos/269102/hot-shemale-fucks-on-first-date/
Just an hour ago these two had met for the first time through a dating app and had met for lunch. ]]> Mon 16 Feb 2026 14:24:34 +0200 https://www.429men.com/videos/269102/hot-shemale-fucks-on-first-date/ https://www.429men.com/videos/325040/tori-mayes-and-her-date-take-turns-fucking-each-other/
]]> Sun 08 Feb 2026 12:04:54 +0200 https://www.429men.com/videos/325040/tori-mayes-and-her-date-take-turns-fucking-each-other/ https://www.429men.com/videos/342035/gender-x-gracie-jane-is-his-very-first-trans-date/
Gracie Jane arrives to Sergeant Miles right after he hangs up the phone. This is his very first time with a trans and who would be the better partner than Gracie? ]]> Thu 05 Feb 2026 23:26:37 +0200 https://www.429men.com/videos/342035/gender-x-gracie-jane-is-his-very-first-trans-date/ https://www.429men.com/videos/246659/shemale-date-went-well-sofia-sanders/
]]> Fri 09 Jan 2026 14:43:40 +0200 https://www.429men.com/videos/246659/shemale-date-went-well-sofia-sanders/ https://www.429men.com/videos/68721/two-trans-babe-enjoy-a-date-lena-moon-and-jessica-fox/
The lovers are unable to keep their hands to themselves as they undress, taking the chance to play with each other's breasts. It's not long before Lena eagerly goes down on Jessica's cock, which has Jessica's head in a spin. When Jessica finally sinks her cock into Lena's ass, they lose themselves in the moment. This is the best surprise Jessica's ever gotten... and she's more than ready to show her gratitude! ]]> Sat 12 Jul 2025 06:17:17 +0200 https://www.429men.com/videos/68721/two-trans-babe-enjoy-a-date-lena-moon-and-jessica-fox/ https://www.429men.com/videos/209621/gender-x-roxxie-moth-give-donte-thick-the-first-trans-experience/
Donte Thick welcomes TS Roxxie Moth in his house. She sees that her partner is pretty nervous because this is his first date with a trans. She says he looks like a virgin, but he knows how to use his cock for sure. ]]> Thu 19 Jun 2025 12:34:48 +0200 https://www.429men.com/videos/209621/gender-x-roxxie-moth-give-donte-thick-the-first-trans-experience/