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Valentine's

Jack Ismay

Created on January 20, 2026

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What's the best way to spend Valentine's Day?

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Anniversary Holiday!!!!

This was the best holdiday i have ever been on, to have the privillage to sit on a sun lounge next to this shinning Goddess in a bikini.... wow. I was a lucky man then, will you make me the luckiest man in the world, and be my Valentine?

That one 21st

I can't explain how warm and seen you made me feel at this party, I was completely out of my comfort zone that night, and I feel so lucky that this stunning woman sat down and spoke to me for so long to make me more comfortable Make me even luckier and be my Valentines?

The Jack Ismay Guarentee

You know it by now, Jack Ismay does not offer his Guarentee's lightly. A Valentine's date with Jack Ismay is a guaranteed success! Fancy making him the luckiest man on the planet and be his Valentine...?

Holiday Beach Walk

We had so many great walks on this beech, we were so honest and open during this time too. We also had those crack slushies.... I can't express how lucky I felt on that beech... make me feel luckier in Cambridge on the 14th of Feb by being my Valentine..?

Politics Christmas Ball

The first time I've had the privilege of seeing you in a dress... and to show you off in the best way possible. I felt lucky to have a woman as effortlessly gorgeous by my side that day... make me even luckier by being my Valentine?

Lady's Day 2025

I dont think I can express how beautiful you looked on this day, so beautiful that even lesbians have it close to their heart. Naomi Jones I am the luckiest man alive, would you make me luckier, and be my Valentine?