An Adventure in Crossdressing: First Kiss

Everyone has secrets; Some people just have more interesting ones…

Jared has a particular inclination, and with his roommates out of town, it’s time for him to indulge it.

All but sure his night is wasted, he takes an unlikely chance that will lead him to a kind of confidence he never knew he had…and a night of passion he could have hardly imagined.

Approximate Length: 4,646 words (A short story)

Adult content warning
This ebook contains material not suitable for readers under 18. It also contains scenes that some may find objectionable, including male/male sex, anal sex, feminization, and crossdressing.

Excerpt:

He walked to the bathroom and checked his appearance once more in the mirror. In the intervening hour, he had touched up his makeup as much as possible, spending the majority of time on his offending eye makeup. He even spent 10 minutes or so brushing the long auburn locks that made up his favorite wig. Clad in one of his favored corsets, along with his breast forms and fishnet stockings, he covered the whole outfit with a long, flowing robe for the sake of introduction. He raised a glass of red wine to his lips and took another sip, noticing the stain his lipstick left on the glass. It helped to calm him slightly, even if it was simply nervous excitement that he felt.

After about five more minutes of waiting, he was dimly aware of a shifting glow coming from outside. He withdrew the curtains once again to see the large dark shape of an SUV pulling into the driveway. It sat there for a moment, the lights remaining on. Jared walked over to the door, and flicked the outside lights quickly off and then on once more. Returning to the window, he could see that the driver had turned off the vehicle. A dark silhouette exited the driver's side, and Jared watched him make his way to the front door, illuminated by the light of the near-full moon.

Jared met his guest there, and was at the inside of the door before he could even knock. A brushed back lock of hair was the last nervous tic Jared allowed himself; He took a deep breath and waited for the signal to come.