Cross-Dressing
Hello, my Sexy Perverts! Last year, I wrote about my best guy friend, Alex, and how we both ended up dressing our sexiest, most glamorous best for a New Year’s Eve party. I thought it would be fun to check in with him again and see what his plans are for New Year’s Eve 2025!
Cross Dressing For New Year’s Eve – Take Two
Once again, we had been invited to the fabulous New Year’s Eve party that everyone wanted to be invited to. It was always the best party of the year, and last year, it did not disappoint. Everyone in attendance was dressed up in their sexiest, most glamorous outfits and had an amazing time. And I think that Alex, with my help, was the sexiest, most glamorous girl there.
Last year, Alex had always wanted to try cross-dressing, and the party had been the perfect time to do it finally. At first, I was a bit surprised that he wanted to try cross-dressing, but he was so excited to put together a beautiful outfit and that he felt incredibly pretty, making his first experience dressing up in ladies’ clothes an amazing one.
Lucky for us, it turns out that Alex had so much fun cross-dressing last year on New Year’s Eve, he wanted to do it again this year. And he wanted my help planning his outfit, too. This was going to be so much fun!
Cross Dressing For New Year’s Eve – The Plan
And so, we began to plan his perfect look. And of course, we had to top last year, which would not be easy. Last year, we had decided on a soft, feminine look with a stunning light blue gown in a flowing fabric with subtle accents of sequins and beads that caught the light and added the perfect amount of sparkle. It was a perfect choice for his first time cross-dressing. This year, though, he wanted to go full sexy glam – think old Hollywood with a modern twist. I could not wait to see what we would come up with! As before, we spent the next few days finding the perfect outfit and planning another luxurious day getting ready for the party.
Cross Dressing For New Year’s Eve – Getting Ready
On the morning of New Year’s Eve, we started with an appointment at the nail salon. This year, Alex went with stiletto nails in a classic, vampy red color. For his hair, we went with the same long blonde wig as last year and styled it into glossy old Hollywood style waves with a deep side part.
Next, he indulged in the now traditional relaxing, spa-like “everything shower. It included an aromatherapy shower steamer, body scrub, body wash, and finished with a silky, luxurious body lotion in a warm vanilla scent.
After relaxing for a while with a glass of wine, I started on Alex’s makeup. I started with a matte foundation for flawless-looking skin and some soft contouring. For eyes, I chose a sexy, sparkly, smoky look with gold eyeshadow and glittery eyeliner, and finished with matte deep red lips.
Once his makeup was perfect, it was time to get dressed. He started with a matching set of a black lace bra and panties, black retro thigh-high stockings, and a garter belt. Then he slipped into a gorgeous floor-length black satin gown with a high slit and a plunging V-neck, and black stiletto heels. We kept accessories simple with crystal drop earrings, a stack of sparkly crystal bracelets, and a little black sequined clutch.
Then, we were both ready to go, and we both looked stunning. Alex was thrilled with his 2025 New Year’s Eve look and thanked me for helping him look even more beautiful than last year!
What Did You Think?
So, sexy perverts – what did you think about my take on cross-dressing for New Year’s Eve? Let me know in the comments below!
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