First Sexual Experience

It was about ?th grade that I discovered masturbation. I was a young, white, blonde haired boy around the age of ?.
I’m not sure where I’d discovered the pleasure that comes from rubbing your dick, but I distinctly recall spending as much time as I could locked away in the bathroom pleasuring myself.

I use to put the fluffy rug that would normally lay on the floor in front of the sink over the edge of the bathtub. I’d then straddle the edge of the tub and hump my little dick against the fluffiness of the rug. I wasn’t ejaculating at that young age so there was no need to worry about staining the rug.

I’d also discovered I enjoyed the sensations I could get from playing with my ass. I couldn’t tell you where I got this idea, but I use to take one of my mothers bobby pins and straighten it out by bending it open. I’d enjoy inserting these up my little ass as I humped the fluffy rug. I enjoyed the tickling sensations I’d get in my ass while I bumped the rug.

I lived with a large family … aunts, uncles, grandparents, sisters all in a big farm house.
The bathroom I use to play in was located on the ground floor. It had a window on the wall. Normally a person standing outside wouldn’t be able to see in through the window because it was high above the ground. But on this particular day I was in the bathroom doing my thing. It was a cold winter day, and in the previous days we’d had 3 or 4 feet of snow I’d guess. It was enough so that when my uncle walked by outside he was able to see me, his young nephew, humping away on the edge of the bathtub.

I don’t know how long he’d been watching me when I noticed him. To say I was embarrassed would be a understatement.
I couldn’t instantly jump up because I had a bobby pin up my ass that I had to pull out first. I reached back pulling it out with one hand while he stood there watching with a big smile on his face. Once I was able to stand up I put my underwear back on and immediately left the bathroom and went to my bedroom. He watched me the entire time.

Over the next few days I’d see him off and on. We lived in the same house so I couldn’t really avoid him. I must have turned red from embarrassment every time I saw him.
Several days later I was in the barn watering my pony when my uncle came in. He made small talk asking me how I was doing etc etc. then he said he’d like to talk to me about what he’d seen me doing in the bathroom. My heart about burst from my chest when he said that. I was so nervous.

The barn had a small room in the corner. Sort of a office. I followed him in there and he told me to lock the door so we could talk in private.
He told me there was nothing to be scared or embarrassed about because it was natural for men to play with themselves. He said he was just concerned that I might hurt myself. He asked what it was I had pulled out of my ass. Embarrassingly I admitted it was a bobby pin.
“That’s what I thought.” He said, as he pulled one from his pocket.

“Like this?” He asked.
“Yes.” I admitted.
“Jimmy I’m going to keep your secret, but I’d like you to show me exactly what you do with this bobby pin. I want to make sure you’re not going to hurt yourself.”

Oh my god I thought. He wants me to do this in front of him? I was so embarrassed.
“Right here? Right now?”
“Yes Jimmy. Right here and right now. No one will know a thing. Besides if you can’t show me we’ll have to talk to your mother about this. We need to make sure you’re not doing anything that’s going to harm you.”

I just stood there. Scared to move. He was sitting on a chair. He reached out and grabbed my tshirt and pulled me toward him. He took my tshirt off for me then told me to take off my pants. I did as he instructed. Standing there in my underwear.
He then said “Take off your underwear to Jimmy.” I did as instructed. I was crying a little from embarrassment.

“Jimmy I want you to relax. You haven’t done anything wrong and you’re not in trouble.” He said this as he was rubbing my shoulders. He did relax me a little bit.
“Now show me how you prepare the bobby pin.”
I took the pin from him and bent it open.
“Now what do you do?” He asked.
“I push it inside me.” I said.
“Do you just shove it in dry while standing up?”
“No, I spit on it.”
“Then go ahead. And get in your hands and knees.”

I got down on my knees and stuck the bobby pin in my mouth getting it good and wet with my saliva. My uncle was beside me rubbing my back as I did this.

“Do you always hump the bathtub Jimmy? Do you ever touch yourself?”
I admitted that I also liked to rub my little dick.

“Now go ahead and insert the bobby pin while you rub yourself Jimmy, and do it slowly so you don’t hurt yourself.”

I teased my ass with the tip of the pin like I always did, and like always it started to excite me. I was playing with my dick with my other hand as I slowly worked the length of the bobby pin into my hole.
My uncle had moved his head closer to my ass so he could watch.
I was still embarrassed but couldn’t help but feel aroused.
Once it was all the way in I kind of stopped out of embarrassment.

“What do you do now Jimmy?”
I told him, “ usually I jump the rug and like how the pin wiggles in my bottom?”

My uncle took hold of the end of the bobby pin and began wiggling it.

“Okay Jimmy. You rub yourself and I’ll wiggle the pin.”

Feeling Uncle wiggle the pin in my ass was sending electric shocks through my body. It felt so good having someone else manipulate the pin. I started playing with my penis while he wiggled the pin in and out of my ass.

“How long do you do this Jimmy?” He asked.
“I keep it up until it feels really really good.”

“Ok let me know when you’re about to feel it.”

I felt my impending climax and I said here it comes. He reached under me with his other hands grabbing my penis as he kept wiggling the pin in and out of my ass.

I orgasmed so hard my hands buckled. I fell forward ass in the air as my uncle kept stroking me and playing with my ass.

I’d never imagined anything could feel so good. No one else had ever touched my dick.

So that was my first ever sexual experience. I’ll tell more if anyone is interested.