Jizz

I was working in an elementary school's file room when I found this...

funny

Honestly I had no idea I was big until I joined swim team senior year of high school and all you guys looked tiny in the locker room. Definitely got laid a lot that year after girls saw me in a speedo. Hot stories will be in comments when this reaches 100

penis

He was none too happy when the other boys took his school trousers, leaving him to go to school in without them.

PublicBoys

My friends in massage school. Thought she was joking when she said she needed a penis to practice on. Fun night!

RealGirls, GonewildPlug, Gonewilds_Secret, WouldYouFuckMyWife

that moment when you accidentally open up r/jilling in the middle of your school library. (sorry for not being jill related. just thought it was related enough. be careful guys)

jilling

Your Mom ran a dominatrix dungeon. She was always very tough on the men that came in, but when your high school bully showed up he was really tough on her throat

mommybully

I was looking at someone I knew in high school on facebook when suddenly.. NSFW

trashy

She was pretty average back in high school, my jaw dropped when I saw her after awhile

jobuds

Hello gentlemen <3 more and more I find myself lusting after assholes and bullies. This is what happens to me when I remember how I was picked on in school by mean boys

RapeFantasy, Misogynyfetish

I was on my way to school like any day when suddenly i passed out. I started to come to, the sound of a running shower in the background. "f...fuck" i said grabbing my head, i noticed the hair and immediately opened my eyes and come to attention. I shriek

AnimePossession

When I hid a live camera in mom's bedroom I finally proved she was lying when she said she wasn't cheating on dad with my high school bully. Sadly it didn't take long for her and my bully to notice the webcam light was still on, and he took pride in fucki

bangmybully, mommybully, GetOutofMYMOM

As a teen, I developed the bad habit of sneaking into my sister's bedroom when she was away. I'd wear her makeup, wigs, and clothes. I told myself I could quit this behavior before I graduated high school, but it wasn't true. In college, I crossdressed fo

EffeminacyAndFaggotry

On school picture day, the male photographer tricked me into posing in girls clothes by saying the lens wouldn't work well for a boy my small size. I knew nothing of cameras and was stupid enough to believe him. But when the school yearbook came out, stud

EffeminacyAndFaggotry

You lived for months in constant fear that I will just show up at your place and abuse your hot Mother. When you came back from school you found your her with legs tied and asshole gaped, dripping in semen. You knew I was there.

IFYM, cuckhumiliation, Cuckik, cuckoldcaptions, cuckoldparadise, GetOutofMYMOM, HumiliationCaptions, mommybully, jerkofftomymom, Latinas4WhiteMen, MomSonIncest, MySluttyMom, raceplay, WouldYouFuckMyMother

I was the smallest boy in high school with the smallest penis, so no one was shocked when they found out I was now living my life fully feminized. Girls even cruelly said, "What girl would have sex with him? His body was obviously designed to please MEN."

EffeminacyAndFaggotry

Every afternoon when I came home from school, I would put on my sister's clothes. I already knew then that I was growing up gay and how I would spend my life in the role of a girl sucking the big cocks of real men and taking it up my ass

EffeminacyAndFaggotry

When I started crossdressing in high school, I thought it was just a phase. But here I am now middle aged and meeting up with other sissies to crossdress and sink into the quagmire of total effeminacy and faggotry together

EffeminacyAndFaggotry

Mommy Dannii Minogue hasn't changed much from high school. If there was club, she was going to be in it. She certainly isn't turning down my invitation when there's a free trip included.

CelebrityMommy

When I hid a live camera in mom's bedroom I finally proved she was lying when she said she wasn't cheating on dad with my high school bully. Sadly it didn't take long for her and my bully to notice the webcam light was still on, and he took pride in fucki

mommybully, GetOutofMYMOM, bangmybully