Hey guys! Long time reader here, but I've never had the courage to share some of my stories around before. I'm not too sure how good a writer I am, so please bear with me, and this story may get a bit too icky for some people in the later parts, so I'll just leave it here for now (better safe than sorry when it comes to internet mods I always think!)
My first experience with TUGs was a few years back when I was in high school with my bf, Mark. We were in year 12, our final year of school and in class we were discussing how to spend our last day at school; all the years before us usually dressed up in a theme (the year before us dressed up as pirates and ran around 'raiding' classes all day long!). Just a few minutes before the bell, one of the girls suggested that guys and girls should swap uniform on the last day. As you can imagine, we all thought this was a great idea, but the guys weren't too impressed.
"C'mon, you'd look great in a dress!"
Mark just rolled his eyes. We were heading back to my place, as we usually did after school to hang out.
"I'm pretty sure no one wants to see my legs in a skirt"
"Oh please, you can try something on when you get back to mine"
He gave me that look; you know the one, eyes squinted as if to say 'Never in a million years', but I had a plan. Mark was always a sucker for a challenge
"Alright, how about this; one round of poker when we get home, if I win you have to try on one of my school uniforms"
"Oh? And what do I get out of it?"
I put on the girliest expression I could, and started playing with a strand of my fringe and said "Well, if I lose, you can do whatever you want to me"
His face lit up with a wry smile, "You're on"