Some of you might be wondering why I am so comfortable with the sissy lifestyle. I actually smile to myself when I prepare my Wednesday blogs, because of how at ease I am when I write about my views about feminization and sissification, emphasizing the sensitive side of things. You should know that it wasn’t always like that! As some of you already know, I was raised in a strict Irish family. Religion was important in my home, as was ‘traditional’ family values. Yes, things were ‘black and white’ for a long time, but all of that changed after high school. And I can’t go any further than that without talking about Josh.
A little backstory…..Joshua: My First Sissy-In-Training
My good friend Joshua had a smile that could melt your heart. (Still does!) Kind and calm, he enjoyed sports and went out with alot of girls, including me! However, Josh and I were better friends than anything else, and I watched him grow in popularity, on and off the field. He seemed distracted when he dated, but he had alot on his plate, too. His folks owned a local business in town, and he was forever flip-flopping about what to do after high school. I had the same dilemma. College offered the possibility of freedom and independent living, but voices at home that were fearful of worldly influences kept us grounded with reminders of family responsibilities.
Josh and I both decided to work after high school, and stay in town but neither of us mad enough to move out on our own. Imagine the shock and surprise of my family when I announced that Josh and I were getting an apartment and becoming roommates. The backlash was what you’d expect, complete with all the drama you can imagine. When all was said and done, I was 18 and free to be me. My family liked Josh, and was happy that at the very least, I would not be living alone. That was true, I would have a protective male friend with me. Things were tense with my folks, but my family hoped that Josh and I would rekindle a relationship. Despite all of that, we liked things the way they were.
My black panties, my red lipstick, and Josh was wearing them!
Everything changed one Friday, when my shift ended early at the restaurant I worked for. I didn’t call home, I just went. Picked up some groceries on the way and planned to make dinner for both of us. When I got home and opened the door, I found Josh sitting on the couch in black panties and stockings, wearing my new lipstick. I was amazed at how natural he looked. The confidence showed on his face, and I stood in the doorway, my initial surprise soon replaced with acceptance of the friend that I loved.
‘We should talk, Amber’, he said with a smile.
‘Yeah’, I replied. ‘How are you wearing that lipstick better than me?’
(You want me to continue, and I want you to come back next Wednesday. My fingers itch to type the rest, but we’ll both have to wait…..)
