An Early Crossdressing Adventure: The Next Day by SissyDemi, literature
Literature
An Early Crossdressing Adventure: The Next Day
An Early Crossdressing Adventure: The Next Day Since the tale of one of my early real-life crossdressing adventures seemed to spark interest (and judging by some of the comments, some bulging panties), I thought I'd write about the following day and what my friend's step-mom made me do. Again, no real sexual contact in my adventure. As this was 35+ years ago, my recollection of details has been colored by time and fond memories. Thus this (mostly) true tale is lightly embellished by wistful memory and a bit of spice and half-remembered dialogue for reading purposes. To avoid the kind of clunky use of "my friend" and "my friend's step-mom" from the last post, I am going to give them names. These are, of course, not their real names ... or are they? We shall call my friend Geoff and his step-mom Sara. She always told me to call her Sara like Geoff did, though my upbringing caused me to call her Miss Sara as a compromise between her first name and Mrs. "Smith". This was in
Double down (A True Life Story ... Kinda) by SissyDemi, literature
Literature
Double down (A True Life Story ... Kinda)
Double Down (True tales of my childhood. No sex involved. Though a cake was seriously harmed.) Even at a young age, I had always wished my mother would decide to make me dress in cute girls' clothes as my daily attire, though keeping me looking like an obvious boy. To that end, I had formulated (and subsequently discarded) a plan to put that into effect. I'm not sure how it would have played out, certainly not like anything I truly would have desired; fantasy is always so much different than reality when it comes to these things. Plus, at the time, mom was very religious. Her church (our church, though I never liked going) might have squelched things. Alas, I think it all may have just been a long-gestating fantasy that started in the mind of my younger self ... Mom had a punishment system she called Doubling Down. Her version wasn't so much based on the Blackjack terminology, but rather the idea of doing something more, or to excess. She may have gotten the idea from
An Early Crossdressing Adventure (True Story) by SissyDemi, literature
Literature
An Early Crossdressing Adventure (True Story)
An Early Crossdressing Adventure I wrote this somewhat in a rush as a response to someone asking me about one of my stories of wearing a pussy-bow blouse. There is no sexual content, though a brief mention of stupid things teens boys think up includes some nudity. I also cleaned up some of the writing and fixed typos. I was about 13 or so, summertime in Florida, and my best friend and I were staying with his dad and his new step-mom (who was only around 10 years older than us!) at their condo on the beach. We were there for a little over two weeks. Halfway through the first week, he and I got bored and played Truth or Dare. We had played it many times back home and had done some crazy stuff. I was already secretly crossdressing in my mom's and sister's stuff and more than once had manipulated things so he would dare me to dress up in their clothes. I usually did so by threatening him with dressing up or some other stupid, embarrassing dare, but he'd keep taking Truth or using what
Romped
What would you like your new sissy girly name to be Chris?
It can be a take on your real name, Christopher -- Christa Patrice. Would you like to be called Christa? Or maybe you would prefer to be called Chrissy. Sissy Crissy. That has a nice ring to it.
We could go really femmy for your new name. How about, Tiffany? That is a really girlish name for a boy like you to be called. Tiffany Brooke. You could be nicknamed Tif or Tiffy.
Or how about Emma? Do you want to be called Emma Chris? Emma Rose. Em is the short version for that one.
I like Stephanie Allison. I could call you Steph or Stephie in public. Or to make you really embarr
Father's Day by Sissy Demi (TS/TG) by SissyDemi, literature
Literature
Father's Day by Sissy Demi (TS/TG)
Father's Day by Sissy Demi (TS/TG)
Katelyn glanced at her watch for the tenth time in as many minutes. She smiled to herself. Only six minutes left on her shift. It had been a busy, tiring day. Father's Day wasn't quite as busy as Mother's Day, but plenty of families were stopping in to celebrate their Dads. And it was heart-warming to see all the happy fathers surrounded by their loved ones.
It was just this reason Katelyn was keenly feeling the slow passage of time the nearer it came to end her shift. She was going to see her dad for the first time since he and her mom split a year and a half ago. Her stomach was aquiver with excitement.
An Early Crossdressing Adventure: The Next Day by SissyDemi, literature
Literature
An Early Crossdressing Adventure: The Next Day
An Early Crossdressing Adventure: The Next Day Since the tale of one of my early real-life crossdressing adventures seemed to spark interest (and judging by some of the comments, some bulging panties), I thought I'd write about the following day and what my friend's step-mom made me do. Again, no real sexual contact in my adventure. As this was 35+ years ago, my recollection of details has been colored by time and fond memories. Thus this (mostly) true tale is lightly embellished by wistful memory and a bit of spice and half-remembered dialogue for reading purposes. To avoid the kind of clunky use of "my friend" and "my friend's step-mom" from the last post, I am going to give them names. These are, of course, not their real names ... or are they? We shall call my friend Geoff and his step-mom Sara. She always told me to call her Sara like Geoff did, though my upbringing caused me to call her Miss Sara as a compromise between her first name and Mrs. "Smith". This was in
Double down (A True Life Story ... Kinda) by SissyDemi, literature
Literature
Double down (A True Life Story ... Kinda)
Double Down (True tales of my childhood. No sex involved. Though a cake was seriously harmed.) Even at a young age, I had always wished my mother would decide to make me dress in cute girls' clothes as my daily attire, though keeping me looking like an obvious boy. To that end, I had formulated (and subsequently discarded) a plan to put that into effect. I'm not sure how it would have played out, certainly not like anything I truly would have desired; fantasy is always so much different than reality when it comes to these things. Plus, at the time, mom was very religious. Her church (our church, though I never liked going) might have squelched things. Alas, I think it all may have just been a long-gestating fantasy that started in the mind of my younger self ... Mom had a punishment system she called Doubling Down. Her version wasn't so much based on the Blackjack terminology, but rather the idea of doing something more, or to excess. She may have gotten the idea from
An Early Crossdressing Adventure (True Story) by SissyDemi, literature
Literature
An Early Crossdressing Adventure (True Story)
An Early Crossdressing Adventure I wrote this somewhat in a rush as a response to someone asking me about one of my stories of wearing a pussy-bow blouse. There is no sexual content, though a brief mention of stupid things teens boys think up includes some nudity. I also cleaned up some of the writing and fixed typos. I was about 13 or so, summertime in Florida, and my best friend and I were staying with his dad and his new step-mom (who was only around 10 years older than us!) at their condo on the beach. We were there for a little over two weeks. Halfway through the first week, he and I got bored and played Truth or Dare. We had played it many times back home and had done some crazy stuff. I was already secretly crossdressing in my mom's and sister's stuff and more than once had manipulated things so he would dare me to dress up in their clothes. I usually did so by threatening him with dressing up or some other stupid, embarrassing dare, but he'd keep taking Truth or using what
Romped
What would you like your new sissy girly name to be Chris?
It can be a take on your real name, Christopher -- Christa Patrice. Would you like to be called Christa? Or maybe you would prefer to be called Chrissy. Sissy Crissy. That has a nice ring to it.
We could go really femmy for your new name. How about, Tiffany? That is a really girlish name for a boy like you to be called. Tiffany Brooke. You could be nicknamed Tif or Tiffy.
Or how about Emma? Do you want to be called Emma Chris? Emma Rose. Em is the short version for that one.
I like Stephanie Allison. I could call you Steph or Stephie in public. Or to make you really embarr
Father's Day by Sissy Demi (TS/TG) by SissyDemi, literature
Literature
Father's Day by Sissy Demi (TS/TG)
Father's Day by Sissy Demi (TS/TG)
Katelyn glanced at her watch for the tenth time in as many minutes. She smiled to herself. Only six minutes left on her shift. It had been a busy, tiring day. Father's Day wasn't quite as busy as Mother's Day, but plenty of families were stopping in to celebrate their Dads. And it was heart-warming to see all the happy fathers surrounded by their loved ones.
It was just this reason Katelyn was keenly feeling the slow passage of time the nearer it came to end her shift. She was going to see her dad for the first time since he and her mom split a year and a half ago. Her stomach was aquiver with excitement.
Current Residence: Florida Favourite genre of music: Classic Rock Favourite style of art: Manga Favourite cartoon character: Pikachu Personal Quote: "Guys can dress cute, too, right?"
I'm still alive! I have not drawn or written anything in a very long time, however. I was in some chat sites for roleplay for a bit, more recently slouching about Fetlife.
Derp Dragons are my new favorite. so cute! ~^.^~
Thjey are the creation of @jimsupreme, who also is the creator of the popular Changes manga. You can check all of that out at the link.
Thanks to everyone who recently began watching my page. Also, thanks to those of you who have favorited things.
I've been away so long I had forgotten that when my troubles regarding posting and such began (elbow injury, living situation) that I had ...
Hello. I've only been a member here for a short while but I've already become quite drawn to the website. I've just begun to read your story line about "The Bad Little Schoolboy" and am already entranced by it. So far, I'm up to page 8. I look forward to each new page as the story progresses. I just love how this has unfolded so far.