How I [M] started my journey to being a fem boy with the help of a stranger [M]

How I became a sissy in school true story btw
Story doctored to protect names and ages

Sorry for rant I just had to tell the world of how this happened to me. Now I don’t look back and feel blessed!:) I don’t remember everything about this day but this is what I’m pretty sure happened. And again, this is a true story but events are jumbled in my silly head.

I live in California where people are very open minded about gender. I was and in school. I hadn’t began growing any hair on my body and was pretty smooth.

At the start of October the principle gave a talk about how gender bending costumes were encouraged and supported blah blah blah. Being a dumb 18 yr old I thought this meant that everyone had to wear a costume of the opposite gender.

I asked to be wonder women and everyone in my family supported it. I had a black wig, the semi short skirt and corset thing. My older sister even did my makeup and I took one of her panties because It had a wonder women design on it and o thought it would work. (I was dumb)

I was pretty happy on Halloween at school. It was a bit of a shock seeing some guys not in girl costumes but it turns out a good fourth of all guys had some gender bending in their costume so I was not alone.

The interesting part happened when I was using the bathroom during homeroom. I couldn’t figure out how to pee with my skirt on with out showing my panties. An older high schooler, Dan, and known weird kid at the time walking into the bathroom and saw me lifting up my skirt and revealing my prepubescent penis. I turned away kinda embarrassed. I must have not seen dan coming when he subtly grabbed me on the waist and pulled me into the farthest stall from the door. I was seriously weirded out but he told keep it quiet. I kept quiet.

Dan then told me to not make an noise or he’d beat me up. That worried me, Dan was kinda tall but he was very bulky and was pretty strong from what I could tell so I went along with it. He then called me a little sissy boy and a fag and turned me away from him and sat down on the toilet. He told me to lick his finger which was really weird at first but I wasn’t thinking strait. Then he stuck the finger up my butt while he pulled the panties to the side. This paralyzed me and I couldn’t think. My whole mind was going wtf wtf wtf wtf.

He kept calling me a sissy slut and a fag while he began sliding his other hand down my panties and started rubbing my tiny penis. I don’t remember the next couple minutes correctly but I soon began to have an orgasm for the very first time and some cum leaked out of me. This felt unbelievably good and I forget about how weird this situation is.

I told dan omg what was that How’d you do it stuff like that. I’m pretty sure he then stood up and left began to leave the bathroom smirking at me. He told me to give me his number and meet him after school during Halloween night and he would show me more. He then left me sweaty and with cum in my red panties leaking through onto my skirt

That all I feel comfortable saying now but I look back fondly on that day. Lol maybe I’ll put out another post about alll the perverted things that happened to me that night :) no regrets!

Source: reddit.com/r/gonewildstories/comments/hehpdi/how_i_m_started_my_journey_to_being_a_fem_boy

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