"Jenni starts the night as a sexy pirate and ends as a high school whore on her first time on campus."
The days couldn’t go by fast enough as I patiently waited for the last weekend of October. While crossdressing on Halloween seemed all too cliché, Missy and I had collaborated on quite an outfit that undoubtedly would be my most...
"A year of frustration is finally rewarded in a way Jeremy would have ever imagined."
The hardest part of the school year and the winter was finding opportunities to explore my newfound feminine side. Often times I would sneak my bra and panties into the bathroom and masturbate while I replayed everything that happened in...
"Jenni's Holiday Weekend ends up with a fun time in the back seat of stranger's car."
Who was this girl? Just minutes ago, Missy was giving me an incredible blowjob. Now she was casually reminding me to make sure I turned over to balance out my tan lines as she sipped from her glass of water...
"Jenni's second makeover turns into an unexpected day of fun in the sun."
A day did not go by when I didn’t think about that night at Jimmy’s house. I would frequently wear the black bra and panties Missy gave me when I was alone at home or occasionally out with friends. My...
"It's hard to imagine 30+ years of crossdressing all started with a simple high school dare."
Like many sixteen-year-old boys, I was at that age where I had moved on from department store magazine bra and panties pages to the pages of Playboy magazine. There was not much left to the imagination in these pictures, and...