Matty Caff
Note: Obviously no one likes my true outings story; so I won't be posting the other four.

I have been going out dressed as a female since I was 18 years old in 1972. This is a 'hobby' I still do often today at age 64. All my stories have images; and although some of the images of me are completely un-retouched (no photo-shop), many were edited to various degrees to fit the stories; but all use my actual face. My true stories are as true as my memory can recall, some stories start as true then diverge to fiction, and some stories are completely fictional. I will try to make it clear which are which. They vary from G-rated to XXX. ;-) My YouTube videos are all of me at home and out in public from the age of 57 through now. I also have a Facebook page so feel free to contact me. :) mattycaff@gmail.com
Member Since: 12/17/17 Membership status: Member
Average Review Rating Given: starstarstarstarstar


Stories by Matty Caff
It is better to read Bedazzled first before reading this sequel. This story continues with Matty returning from her first date with a man and follows her path through new adventures and life changing decisions.
Rated: Explicit 2 Reviews starstarstarstarstar Completed Story Reads: 3789 Words: 18413 Chapters: 2 Table of Contents
I worked odd jobs for years, and finally at age 24 saved enough to start my education at the university; but not enough for all four years. Being the somewhat sissy nerd I am, it is a great surprise when I am asked to pledge the fraternity Sigma Epsilon Chi. I'm told I am in a special category, and they will only select one pledge as a brother next year from those pledging in my group.
Rated: Explicit 0 Reviews starstarstarstarstar Completed Story Reads: 4883 Words: 8978 Chapters: 1 Table of Contents
I'm a man who laughs off the idea of hypnosis, and I share an apartment with 2 girls. Who's laughing after they prove me wrong? Not every story has to be serious, so I hope you enjoy this simple little fantasy tale. Also, I hope to surprise you with a twist near the end.
Rated: Adult 0 Reviews starstarstarstarstar Completed Story Reads: 6185 Words: 6861 Chapters: 1 Table of Contents
I always wanted to be as pretty as Mommy. She never thought I should have been a boy. Mommy is always right. This fictional tale is told year by year, from age 5 to 18, as Mommy slowly guides me more and more into the world of femininity.
Rated: Explicit 0 Reviews Completed Story Reads: 4316 Words: 14969 Chapters: 1 Table of Contents
Just a sexy fluff piece for fun. Matt just isn't fitting in at work and his friend Carol helps him make some changes. This is the story and pictures of the six-month changing of Matt into Matty and a sexy life ‘he’ never expected but ‘she’ learns to love.
Rated: Explicit 2 Reviews starstarstarstarstar Completed Story Reads: 3959 Words: 7762 Chapters: 1 Table of Contents
Matty makes permanent changes to her new gender; but how far will she go? Experiencing lust and love, she is conflicted before she makes her final commitment. Each “Matty’s Life with William” story is written to stand alone, but together will make a series of accounts of our times together and how my life progressed deeper and deeper into femininity.
Rated: Explicit 0 Reviews Completed Story Reads: 2662 Words: 9732 Chapters: 1 Table of Contents
Matty now out living as a woman moves in with William. She has many new adventures, including the major event of meeting William’s family. She also explores her new sexuality and experiences seduction from both points of view. Becoming just one of the girls takes an erotic twist. Each “Matty’s Life with William” story is written to stand alone, but together will make a series of accounts of our times together and how my life progressed deeper and deeper into femininity.
Rated: Explicit 0 Reviews Completed Story Reads: 1761 Words: 14580 Chapters: 1 Table of Contents
Matty continues even deeper into the world of femininity. Now living full-time as a woman she faces the difficult task of revealing her changes to friends, family, and especially William; as well as giving in to temptation. Each “Matty’s Life with William” story is written to stand alone, but together will make a series of accounts of our times together and how my life progressed deeper and deeper into femininity.
Rated: Explicit 2 Reviews starstarstarstarstar Completed Story Reads: 1925 Words: 9728 Chapters: 1 Table of Contents
Matty continues deeper into the world of femininity. Thinking more of herself as a girl; she begins publicly dating her boyfriend, meeting new people who only know her as female, and experiences erotic encounters and new temptations. Each “Matty’s Life with William” story is written to stand alone, but together will make a series of accounts of our times together and how my life progressed deeper and deeper into femininity.
Rated: Explicit 1 Reviews starstarstarstarstar Completed Story Reads: 1899 Words: 6683 Chapters: 1 Table of Contents
Categories: Realistic Gender Change
Characters: Male to Female, Young Adult (20-26 yrs)
Turned Into: Girlfriend
Featured Items: Breast Forms, High Heels, Long Nails, Pantyhose
Locale: College
Motivation for Change: Male Domination, Willing or Voluntary
Personality: From Dominant to Submissive
Sexual Orientation: Becomes Bisexual
Story Type: Includes Images
Story Theme: Beauty/Fashion, Coming of Age, Everyday Living, Romance
Type of Change: Hormonal, Slow/Gradual Change
Series: None
Published: 01/19/18
Updated: 01/19/18
Matty makes some permanent changes to begin living as a woman to be William’s girlfriend. Each “Matty’s Life with William” story is written to stand alone, but together will make a series of accounts of our times together and how my life progressed deeper and deeper into femininity.
Rated: Adult 4 Reviews starstarstarstarstar Completed Story Reads: 4094 Words: 6143 Chapters: 1 Table of Contents
Categories: Realistic Gender Change
Characters: Male to Female, Young Adult (20-26 yrs)
Turned Into: Girlfriend
Featured Items: High Heels, Long Nails, Pantyhose
Locale: College, Formal Dance
Body Modification: Permanent Hair/Skin/Nail Change
Motivation for Change: Willing or Voluntary
Personality: From Dominant to Submissive
Sexual Orientation: Becomes Bisexual, Does Not Change
Story Type: Includes Images
Story Theme: Beauty/Fashion, Coming of Age, Everyday Living, Romance
Type of Change: Drug-Induced, Hormonal, Slow/Gradual Change
Series: None
Published: 01/11/18
Updated: 01/11/18
'True' diverges into fantasy as 'Matty' falls deeper and deeper into femininity and gets her first boyfriend. This is the inspiration for my 5-part 'William Series' of a slow transformation from a straight crossdresser to a bi transgender woman.
Rated: Explicit 1 Reviews starstarstarstarstar Completed Story Reads: 2667 Words: 12638 Chapters: 1 Table of Contents
Categories: Realistic Crossdressing and TV
Characters: Male to Female, Young Adult (20-26 yrs)
Turned Into: Girlfriend
Featured Items: Breast Forms, High Heels, Lingerie, Long Nails, Pantyhose
Locale: College
Motivation for Change: Dared into It, Tricked, Willing or Voluntary
Personality: From Dominant to Submissive
Sexual Orientation: Becomes Bisexual
Story Type: Includes Images
Story Theme: Beauty/Fashion, Coming of Age, Romance
Type of Change: Changed by Clothing, Slow/Gradual Change
Series: None
Published: 01/02/18
Updated: 01/02/18
I described my relationship with my girlfriend, Lori, in my first story. My first dressing experience in public was with her. This story takes place two-years later, and ends about 3 months before my first story “Matty’s Sexy Debut”. Lori and I spent an entire summer living together before my senior year of college. This is the story of some of the different looks achieved and adventures we experienced together (or at times alone), while either playing at home or going out in public. It was an amazing summer of often being two girlfriends and lovers. When in public I would be somewhat conservative in both dress and makeup. Although sometimes a bit sexy, it was never flamboyant or overt. When we were home alone though, it was time to try many various makeup and dressing looks that would be inappropriate for the public. The best part of this though was the opportunity and ability to act upon the urges being a sexy woman stirred in me. Each chapter can stand alone as a separate min-story, but together they are the highlights of a fantastic summer for Matty.
Rated: Explicit 4 Reviews starstarstarstarstar Completed Story Reads: 3614 Words: 8697 Chapters: 1 Table of Contents
A true account of my first time out in public dressed in a sexy outfit.
Rated: Kid-Friendly 3 Reviews starstarstarstarstar Completed Story Reads: 4015 Words: 5140 Chapters: 1 Table of Contents
Categories: Realistic Crossdressing and TV
Characters: Male to Female, Young Adult (20-26 yrs)
Featured Items: High Heels, Long Nails, Pantyhose
Locale: College
Motivation for Change: Willing or Voluntary
Sexual Orientation: Does Not Change
Story Type: Includes Images
Story Theme: Beauty/Fashion, Everyday Living
Series: None
Published: 12/26/17
Updated: 12/27/17
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