Just Awkward!
 

Exactly as the title says....

1) Describe your most awkward moment from school.

2) Describe your most awkward family experience.

3) Describe your most awkward sexual experience.

Go!

1) Describe your most awkward moment from school.
Getting a boner in front of everyone when I had my first kiss

2) Describe your most awkward family experience.
My mum finding that I had taken my sisters old bathers to wear and I hid them in my cupboard. She hid them again though

3) Describe your most awkward sexual experience.
First time having sex she was slowly tugging my dick. I came on her dress. Super humiliating

1) Describe your most awkward moment from school.
in my culinary class, I popped a boner and (due to my not so small size and quite skinny jeans) the girl sitting next to me thought I had a dildo in my pants and I got in trouble for "bringing a sex toy to school". I had to explain to the school guidance counselor that I didn't bring a dildo to school, I was just well endowed.
2) Describe your most awkward family experience.
Showing up to the family Christmas dressed as a girl without telling anyone I was a girl now. Lotta awkward smiles and confused looks.

3) Describe your most awkward sexual experience.I hooked up with this dude from grinder. He wanted to fuck my ass but the problem is I'm dummy thick, and his dick was about 2-3 inches long. Like, I had to sit there and awkwardly fake moan while his tiny dicklette fucked my ass cheeks. He couldn't even get it in. It was sad, I was sad, I didn't even wanna tell him how bad he was. Worst part is, he thought that he "tore that shit up"

Exactly as the title says....

1) Describe your most awkward moment from school.
The time in Gym class when I let out the biggest loudest fart I think I ever let out. It echoed the ought the room.
2) Describe your most awkward family experience.
The time mom caught me pleasing myself while naked
3) Describe your most awkward sexual experience.
She was my first girlfriend and I wasn't kissing her properly. She grabbed my head, forced it against her face and her tongue was inserted in my mouth
Go!

1) Describe your most awkward moment from school.

In middle school, I was wearing white shorts one day. That also happened to be the day I got my very first period. Yay...lucky me. I wouldn’t come out of the bathroom because it was so noticeable with my white shorts. I never wore white shorts or pants ever again. I don’t even wear khaki haha. I only wear black or dark blue now.

2) Describe your most awkward family experience.

I went to spend a weekend at a hotel with a guy. I told my family I was driving down to visit one of my friends who lived about 2 hours away for the weekend. While I was gone, they decided to go through my room, they found all three vibrators that I owned at the time. When I got back, they said they found some unmentionables in my room. I couldn’t find those vibrators after that. I found them hidden in a box in another room months later haha.

3) Describe your most awkward sexual experience.

I had car sex with the last guy I dated in the middle of a busy parking lot. The car was shaking violently and we steamed up with windows. When we were done, I got out of the car and there were several guys watching me make the walk of shame back to my car. Of course they probably knew what was going on haha.

1) Describe your most awkward moment from school.
Honestly do not remember anything really awkward... :(

2) Describe your most awkward family experience.
Being home with my parents, I locked in my room and took some nude pics... Dumb enough, I did it with flash, which made my mum curious about what am I taking phots of... She tried to walk in and came to locked doors - weird, as I never locked... I quickly pulled my clothes on and opened the door just to let her tell me I have the t-shirt on the wrong way (inside out)...

3) Describe your most awkward sexual experience.
Just a few days ago, after a fine hour in a gym, I went to shower. Was there alone, so decided to let the steam off... Closed my eyes and masturbated. Once i finished, I found out that I am no longer alone in the showers (two other guys were in close shower-cubicles, at least one of them was going around me, with no curtains on the shower boxes...)

1) Describe your most awkward moment from school.
I was 7 yrs old, in middle of a class, and in that moment i really, really want to go the bathroom, i ask multiple times to the teacher, but she doesn't allowed me to go...the last time i stand up to tell her the urgency of my case, i started to pee myself in front of my classmates.

2) Describe your most awkward family experience.
Well, i told this in a another topic, but well...

When i was 14, i was sitting in my desk in my bedroom at night, watching porn and masturbating, i was denied myself to cum for about 2 hours, i was really on edge, and full concentrated to not cum yet. So, i keep stroking one more time, and then, my mom enters to my room, i didn't have time to cover myself, so my mom could see my erected dick...and that jump scare she gave to me, i couldn't hold it anymore, and she saw me how i came...she didn't speak me again for about a month.

3) Describe your most awkward sexual experience.
I'm still a virgin...but there is a moment, that i could lost my virginity with a college friend, we went to a party and i offered her to take her home, when we arrive, she said to me "i have to compensate this..." in a very sexy way, she tart to touch my leg, kissing my neck, star to unzip my pants...and...well...that's it...y came in my pants...she saw this, gave me a kiss , and left without a word...

Please punish me.

1) Describe your most awkward moment from school.

Went poop, no tp. Went to next stall, didnt have a door. Bully walks in. Stupidly i poke my head around the cornwr and say dont come in here (the stall). Of course bully comes around to catch me with my pants down. At lunch he announces that i called him in there. Oy

2) Describe your most awkward family experience.

I panicked one time i was tieing myself and yelled for my mom who found me shirtless my hands tied behind my back up towards my neck.

3) Describe your most awkward sexual experience.

I was tied face to face with a old fat smoker dude and i didnt know what i was supposed to do but i wasnt in to him. Eww