I had -- and still do have -- two older sisters. One is somewhat older, so as kids we really did not hang out together much.
The other is just a year older than me, leading me to believe that I was my parents' oopsie! We went through school together, with her in the grade ahead of me of course. By the time we were in junior and senior high school, she was one of the prettiest and most popular girls in school. She always had boys chasing her -- I became pretty envious! -- and always was elected to some sort of student government position, which is pretty much a popularity contest.
But what pertains to my sissy story is that because I was a year younger than her and because I had a girlie body -- meaning skinny arms and legs especially -- we were very similar in build. And that meant her clothes fit me!
At some point around sixth grade I started going through her dresser drawers and putting on her panties when I was alone at home. She liked to wear short dresses and I would put them on too.
I would always hang up the dresses where I found them, but what got me in trouble was that I would take the panties for extended periods to wear them and of course I would not put them back in the drawer but put them in with the laundry. My mother, who did the laundry, did not notice this because my sister could have been wearing them, but eventually my sister did!
So what happened next? She confronted me about it! I don't remember exactly what happened, but I imagine I was quite surprised and upset and very uncomfortable! She did, however, say it was okay and not to worry about it.
The reason why is that it was pretty evident the way I was going to be by sixth grade. I was not some rugged boy. I was not extremely girlie, but I was somewhat effeminate, very shy, emotional, and most of the people close to me still were other sissies, girls or female relatives.
Of course, my sister knew all of this. On that day she confronted me, she was the best sister a sissy could possibly ask for! She told me that she understood and that if she gave me some items I had to promise her to no longer get into her stuff. I certainly agreed! And she came through. She gave me some things she was okay to part with: panties, pantyhose, a bra and a couple of short dresses.
So that was actually when my sister and I became very close and we still live about 15 miles from each other. That was also the beginning of my having a sissy "stash." Did you have one of those!?
Now, there so happened to be another sissy up the street from me who I went all through school with. His name was Timmy. He was a bigger sissy than me. Not larger, but meaning, he talked like a sissy and walked like a sissy. The poor kid got picked on in school a lot more than me. Timmy was always with a group of girls. For some reason they really accepted him. That was true with me too, but especially with Timmy.
So Timmy was one of my closest sissy friends. I would always be at his house up the street. His house had a third floor that was an apartment where his grandma once lived. It had a bedroom, a bathroom and kitchen/dining area. It turned out to be a perfect hideaway and play area for us!
One time -- I'm pretty sure this was still in sixth grade or it could have been the summer right after -- Timmy asked if I wanted to do something really fun. He brings out some of his mother's lingerie, including slips, stockings and a garter belt! So we started dressing up together at that point, a first for the both of us doing it with someone.
What was funny was that when we undressed to put on the lingerie we both were wearing panties already!
So that summer we played dress-up whenever we could. Having my own stash of undies and dresses given to me by my wonderful sister, I of course brought them to our play time and kept some of the stuff there.
So we would dress up and prance around and it was such a good time, as you might expect. We were able to lock the door for privacy once we were up in that apartment area!
This led to our getting into bed together. That started with us being silly and tickling each other and playfully kissing each other. We started getting into bed nakie or in lingerie and cuddling. We would tuck our little sissy clitties and pretend we were girls.
Two things from this:
I thought I was tiny down below. I had something like a little over an inch of clitty. Timmy was even smaller than that. When we cuddled we would get erections because that just came natural but they were very, very feeble erections.
Leads me to think that we were born sissies! I wonder: If you are not born with manly equipment, do you start out thinking that you are not manly? There I was -- sort of a weakling, shy, wanted to be around females, and I had a very little boy thing! Seems to me that had something to do with it.
Where did my cuddling and kissing with Timmy lead us? Although I lost track of him through the years, I know from Facebook that Timmy ended up being married to a man.
And me, well, after finding I was not accepted by the gay community as a tranny, I ended up being a submissive sissy wife to a dominant woman! Talk about a turnaround. As you will see from some of the things I am going to write about during my teen years and years shortly after college, I very well could have gone either way.
The second thing is that Timmy was the first person I ever kissed on the lips! He was just so gentle and they were such gentle kisses. Like girl kisses, actually. And yes, I did kiss some girls after that even though I was a sissy! So I knew what it was like to kiss a girl! Maybe since I did like kissing someone who was feminine is how I ended up being partnered with a dominant woman instead of a man. Who knows!