First Date with a T-Girl

"It was their first date, a few laughs and a quiet drink."

Daniel Deveron was fascinated with Kay Pritchard. Her short black hair framed her face nicely; her slim figure looked amazing in the mid-thigh length, black and white polka dot dress that swirled as she walked. Her breasts, although small, had...

Becoming a Sissy

"Becca is Born."

For the longest time I can remember loving the look of pantyhose on a woman. It made their legs look so sexy and especially when they wore heels. I would always jack off while looking at pictures of women in...

My Crossed Life – Chapter 6: Valleys, Peaks & The Professor

"Jenni makes her return in college - a story of rising up and going down."

The sexual high of Halloween weekend came crashing down three weeks later when Missy stopped by my house unexpectedly. She was in tears. I assumed the worst, thinking something had happened at school. It was far worse. Missy’s brother and...

Pinked

"Brad becomes Pink and finds a hot Daddy."

At twenty-five, everyone Brad knew said he looked a lot younger, more like nineteen. He'd still get carded at bars which both intrigued and annoyed him. He had a good if boring office job and had his own apartment. Like...

It’s A Family Affair

"Oh The Shame... The Shame!"

It wasn't unusual to receive a phone call from Rebecca at eleven o'clock in the evening. Since her recent divorce, she often called for a chat with my wife Linda. "Hey, gorgeous!" I answered the call on the landline.Rebecca, aka Becky,...

My First Walk On The Wild Side

"It was forty years ago when I first ventured out as Michelle."

It wasn't until I was in my mid-twenties that I plucked up the courage to leave the house dressed as a young woman. Initially, it was short walks to the end of our street (a relatively quiet suburban road in...

My Crossed Life – Chapter 5: A Very Happy Halloween

"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...

My First Sissygasm

"Taking a next step towards femininity"

 This is a true story about the first time I felt the sensation of cumming like a girl.  I don’t mean a prostate orgasm, where you ejaculate through anal penetration, but my first time feeling what I can only describe...