My Life with Tess McGregor Ch. 01 - Sex Stories

My Life with Tess McGregor Ch. 01

Ch. 01 Tess Moves in Next Door

My name is Brad Collings and this is the story of Tess McGregor. It may not be THE definitive story of Tess, but it's my story, and I'm pleased to share with the world my experiences with this extraordinary woman.

Tess was born Thomas Elvin Sanger Stewart in 1980 to a wealthy family in San Francisco, California. Tommy was a bright and articulate child. He was always interested in art and fashion. Like his best friend, Nathan Campbell, he wasn't like the other boys in school. Tommy and Nate knew they were different and struggled at times to fit in.

Nate was not supported by his middle-class family. They didn't understand why Nate would rather play dress-up with his sister's dolls than play outside with the other boys. Consequently, he spent much of his time at Tommy's house where they were given the freedom to be who and whatever they wanted to be.

Tommy had older sisters who taught him a lot about what it was like to be a girl. Nate followed along as they both grew older and less worried about society's expectations to be young men.

A few years after graduating high school, Tommy and Nate moved to Los Angeles. They rented an apartment together near Hollywood.

It was decided between the two of them that moving to Los Angeles would allow them to trade in their old identities for new ones, and that included a new lifestyle. They continued to grow their hair out. They donated most of their male clothes after they made a ...

... significant clothing purchase. They wanted to be who they felt they were deep down inside. Women.

Tommy changed his name to Tess, using the initials of his full name, and took her mother's maiden name of McGregor. Nate altered her name to Nataly.

They were almost complete. Just a couple more alterations and they would be satisfied with their transition.

They took estrogen for a while and with the help of Tess's family allowance, they both were able to get breast augmentation surgery.

Their voices started to change. Their mannerisms were more feminine as they became more comfortable in their new bodies. They both would often comment to each other just how passable they had become. Tess was taller and more slender than Nataly. Nataly was bustier, but both had curves and soft feminine features.

A few weeks after their surgery, Tess and Nataly were posing in front of their full length mirror, admiring the work they just had done. Tess's hair had grown to a length that, to her, was very pleasing. Her dark brown tresses fell just past her shoulders in large pretty curls. Nataly's hair was silky, blonde and straight. It also fell past her shoulders.

After years of learning from Tess's sisters how to apply makeup, they were very adept at choosing the right foundation and colors that accentuated their skin tone and features.

Tess and Nataly giggled at the way they looked in the mirror. They were in love with their new bodies and were anxious to get out and show the ...