Crossdressing

My Mom, My Cousin, and Me: Part 1

It was a scorching June day when this all took place. I was 13 and living alone with my single mom. I was homeschooled, but not sheltered from the world. My mom was my hero - my dad was gone before I was even born, so she raised me solo without any help, all while owning and operating her own successful salon. We did well for ourselves, had a nice house with a pool. Despite her busy schedule she always made time for me, and even though I was homeschooled I never felt coddled or alone with her parenting. I based a lot of my personality and work ethic off of her.

If It Was Your Husband 1 & 2 of 20

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Authors Note: This story is complete and sitting on my hard drive. The novel is 49,188 words long in twenty chapters. I will be posting two chapters per week, roughly 5,000 words per post, on Fridays.


Synopsis

Alex comes home one day and his wife, Carrie, tells him of a problem in Mike and Lisa's marriage. Mike is his best friend since middle school. It seems that Lisa caught Mike cross-dressing and came unglued. She had come to Carrie looking for solace and support for divorcing Mike. But Carrie told her about a Phil Donahue show she'd seen as a teenager featuring married cross-dressers and said that cross-dressing really was no big deal.

Lisa was offended that Carrie wouldn't back her up and said, "If it was your husband, you wouldn’t think it was so cool," and left in a snit; part of her anger now directed at Carrie.

Carrie, on the fly, hatches a plan to help Lisa see that if it was her husband, she'd still think it was no big deal. Alex somewhat reluctantly goes along with it and discovers things about himself that he never knew existed.

Dresses from Diana: A Gradual Feminization Story (Chapter Three)

He’s stumbled upon a collection of Grandma’s old dresses and his cousin insists he try them on. But it's all just for fun... right?

It’s the summer before college, and Madison’s task is to clean out his late Grandma’s entire house before it’s sold. Even worse, he has to do it with his annoying, bratty cousin, Olivia. But while digging through boxes, they discover something unexpected: beautiful, vintage dresses of a wide variety of styles… and Grandma’s unfulfilled dream for someone to wear them. What starts as silly bonding activity for Madison and Olivia turns into much more when they realize how convincing Madison looks as a girl, leading them to take advantage of his feminine looks.

This ~50,000-word novel is available in its entirety for Kindle. This is the third of three chapters that will be shared here as a sample. Hope you all enjoy! :)

-Jennifer

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sissygirl’s journey 5.5

It’s funny how being a little mortified and days later looking forward to the same thing, isn’t it crazy how human emotions can play little games in your head, that’s how I felt about sissy meeting my auntie one minute thinking one way and now really looking forward to it, mom really didn’t say too much just mentioning sissy that would be nice to give our guests a hello kiss just to make them feel welcome.

sissygirl’s journey 5.4

Mom having me kiss my Barbie doll with my freshly applied lipstick I think was just a way to have me start wearing lipstick because she knew i was fascinated with her lipstick and it wouldn’t take much to have me fall in love with wearing lipstick.

Dresses from Diana: A Gradual Feminization Story (Chapter Two)

He’s stumbled upon a collection of Grandma’s old dresses and his cousin insists he try them on. But it's all just for fun... right?

It’s the summer before college, and Madison’s task is to clean out his late Grandma’s entire house before it’s sold. Even worse, he has to do it with his annoying, bratty cousin, Olivia. But while digging through boxes, they discover something unexpected: beautiful, vintage dresses of a wide variety of styles… and Grandma’s unfulfilled dream for someone to wear them. What starts as silly bonding activity for Madison and Olivia turns into much more when they realize how convincing Madison looks as a girl, leading them to take advantage of his feminine looks.

This ~50,000-word novel is available in its entirety for Kindle. This is the second of three chapters that will be shared here as samples. Hope you all enjoy! :)

-Jennifer

DFD_V1_3 (FINAL).jpg

sissygirl’s journey 5.3

The first time mom put lipstick on me when she was tucking me in, up until then she was having me kiss my Barbie doll good night, after she kissed me good night on my cheek or forehead.

That night she said sweetie look in your purse which I usually kept on my bed at night with my Barbie doll, grabbing my purse unsnapping the clasp looking inside and there was a new lipstick tube before my very eyes, I was so excited just looking at that wonderful item of girlhood.

sissygirl’s journey 5.2

My nephew was 4 and I was 7 it’s been about 2 years now since mom and I started down my girlhood journey, I know I’m jumping ahead a little but I’ll get back to the beginning after this little side adventure.

Mom loved me and my girlhood telling me years later she did it for me seeing how I loved girl things and my girl feelings she wanted to help me also admitting she enjoyed it too, even loved having two daughters at home, I think my sister being a jock and not really being very girly had mom really enjoying my feminine side but anyway.

sissygirl’s journey 5

Most of mom’s girl talk with me was when she was tucking me into bed and also a good time to introducing me to other girly things too.

Mom started out being somewhat curious about my interests of girly things and it grew from there, seeing what else I liked and seeing how far she could take it, I think at that point she was really enjoying it.

I always had that girl gene deep inside me and mom pushing me towards girlhood it was more than not a little emotional and embarrassing to say the least but I survived and of course I loved it too.

Dresses from Diana: A Gradual Feminization Story (Chapter One)

He’s stumbled upon a collection of Grandma’s old dresses and his cousin insists he try them on. But it's all just for fun... right?

It’s the summer before college, and Madison’s task is to clean out his late Grandma’s entire house before it’s sold. Even worse, he has to do it with his annoying, bratty cousin, Olivia. But while digging through boxes, they discover something unexpected: beautiful, vintage dresses of a wide variety of styles… and Grandma’s unfulfilled dream for someone to wear them. What starts as silly bonding activity for Madison and Olivia turns into much more when they realize how convincing Madison looks as a girl, leading them to take advantage of his feminine looks.

This ~50,000-word novel is available in its entirety for Kindle. The first few chapters will be shared here as samples. Hope you all enjoy! :)

-Jennifer

DFD_V1_3 (FINAL).jpg

Halloween Romance (6)

Halloween Romance
Sequel to
Mischief Night Magic
Part Six: A Lesson on the Perils of Womanhood

Gwendoline took a deep breath as she closed the heavy wooden doors of the girls bathroom behind her. She then started to walk around every square foot of the bathroom. Once she was sure we were along she turned toward me and heaved another long, drawn out sigh.

sissygirl’s journey 4

As I handed mom her purse she always gave me that cute little smile as with her eyes too, she knew I loved her purses while giving me purse time and still being nonchalant about it, a few times she would quietly say you love it, I knew she was just having a little fun I just stood there and didn’t say a thing but yes I did.

sissygirl’s journey 3

So mom really didn’t get upset or mad about anything but she did let you know if she was not happy and her personal lipstick collection was one of them.

Being a very curious little boy and mesmerized by her lipstick I would always find myself looking through her lipstick collection.

Little boy’s can never put anything back correctly or organized we’re just too focused on the prize and her lipsticks being in a pretty tube I would twist those amazing lipsticks out of their tube and spend my time enjoying all the different and wonderful colors and scents.

Halloween Romance (5)

Halloween Romance
Sequel to
Mischief Night Magic
Part Five: A Cup Of Poison

I felt my hips starting to sway this way and that, all in tune with the music the dj was playing as I waited for my vampire to return with my requested cup of spiked punch. As I waited, I felt small beads of sweat starting to roll down my body, making my costume sticking to me. And I could feel the effects of the alcohol taking hold of me. I was sure I was starting to catch the first rising curls of a buzz.

sissygirl’s journey 2

Hi everyone, before I continue I would like to give a little view into my life at that time.

Mom, what can I say she was a wonderful mother very supportive of everything my sister and I did with all the love she had.

My sis was 3 years older than me and being a real jock she had her own group of friends and from what vibe I got from her she wanted nothing to do with me especially when mom and I were exploring my other side, of course mom always tried to kept it out of sight so nobody got uncomfortable to a certain point as you will see, she was a great mom.

sissygirl’s journey

Being about 5 or 6 I was mesmerized by my mother’s black patent purses and her lipsticks also my sister’s black patent Mary Janes, any chance I had I would go into her closet and reacquaint myself with those beautiful patent little girl shoes.

I would pick them up to get a closer look feeling the shiny smooth patent leather and playing with the buckle just in amazement of how pretty they were, if time allowed I would take them back to my bedroom to wear them.

Family Therapy

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A father and son in crisis reach out to an online therapist who, unbeknownst to them, is actually an artificial intelligence. But after the machine mistakenly deduces that one of them must be transgender—and bound by its programming to maintain its patients' privacy—it ends up feminizing both father and son. When the truth finally comes to light, will this bring the two of them closer together, or tear them hopelessly apart?

Just Do What The Nice Man Says Honey

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Alex lives with his mother Julie and refuses to get a job or to help Julie pay the rent and household bills. When Julie sees pictures of Alex dressed as a girl she sees that Alex has potential for meaningful employment, even though Alex might not want the job.

My Time as a Wife

This is a continuation of "Life's Lottery". Steve is delving deeper into his Sarah persona.
This story contains sexual scenes.

I bit the bullet and took some pictures of myself as Sarah. Nothing
outrageous, mainly just myself in various wigs and underwear. Then I
posted them on a few contact sites. I really did not know what to expect,
and to be honest I really don't know why I did it. I think I was seeking
affirmation that I was acceptable as a woman by men.

Love Story - Chapter 9.5

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