HOME | DD

#highheels #tg #tgtf #tgcaps #kelliberglund #tgcaptionstory
Published: 2021-12-13 20:17:57 +0000 UTC; Views: 24537; Favourites: 173; Downloads: 11
Redirect to original
Description
Fuck I think to myself as I am placed in an impossible situation.The last 24 hours have been some of the worst of my life. For my senior trip my school was going to New York. We had to pick 5 group mates for the free time and we had to pick 6 roommates for the hotels. We had to pick the group mates before the trip and pick the roommates at the hotel. My friend group was made up of 6 people so to keep things fair we decided on a coin flip to determine who would join a different group. I was the loser. I was reassigned to group “D” which coincidentally had 4 of the most popular girls in school. Fuck.
That’s not it, on the way there we got hit by tons of traffic. Leading to a delay in time to arrive. This wouldn’t have been too bad for me except for the fact that because of the delay we no longer had time to choose our roommates. We had to stay roommates with our group mates. Fuck.
Upon further inspection as to why I, a boy, was allowed to be roommates with girls I checked the paper work that we filed out at the start of the trip. As it turns out one of my dumbass group mates checked “girl” for all of our genders, forgetting that I was apart of the group.
Now we are in the present, when I am walking over to my room. The boys and girls were separated into two hallways, on the left were the boys, on the right were the girls. So as I turn right to go to my room I am stopped by a teacher.
“Um excuse me sir, you’re a boy not a girl. No funny business” as she redirected me to the boys side.
As I’m pushed towards the left hallway I panic and run to the bathrooms. I had no idea what to do other than ask Olivia ( one of my roommates) to show the slip saying I am in that room. I call her on the phone and she tells me that she’d be over right away.
I wait outside of the bathrooms, making sure to stay out of sight of the teacher. I spot Olivia coming over and notice something odd. She has brought a suitcase, and the rest of our roommates. “Why would she need all of this?” I think to myself. As she hastily arrives she pushes me into the girls bathroom, into one of the stalls. Making room for everyone else to enter.
“If we’re going to help you, your doing it our way.” She says confidently. Resting her hand on her hip.
“Okay.. what does that mean?” I ask nervously.
“You are going to dress up as a girl in order to sneak past ms grimshaw.” She says smirking. The other three giggling behind her.
“What, as if!.” I say. Starting to panic a little.
“Fine.” She says. “Have fun trying to get past ms grimshaw. Even better, have fun trying to explain why you are grouped with a bunch of girls.” She says cracking another smile.
I panic even more, “she’s right” I think, “there’s no way I can get past ms grimshaw without looking like a total perv and maybe even getting expelled.” I think.
“Fine.” I say reluctantly.
The girls whip out the wigs, makeup, breast forms, and outfit from the suitcase. They start applying everything to me holding me down and attaching things to my body.
When they finished I looked in the mirror and was shocked to see another girl staring back at me.
Before I can do anything else I’m pulled out of the bathroom and escorted to the room by Olivia and the other girls. Ms grimshaw didn’t give it a second thought as the the 5 bubbly girls in highheels and skirts strutted by. The disguise worked.
To be continued