Your very first orgasm

[ShadowCat]

I was 14. Ok so my dad had g strings from his and my mom's kinkier sex days there was one with a sheer black sheath in it I never understood what it was for til I thought hey maybe I can get my cock in there and I did! It felt cool and warm at the same time! There was a pleasurable sensation when my finger went from the tip to the base. I liked the way it felt and started doing it with both hands then all of a sudden it felt like I needed to pee! I figured I'd just pee in the sheath and dry it with the hairdryer well this pee shot out but it wasn't pee it was creamy thick and whitish yellow I thought it was pus! In Catholic school they dont tell you anything about masturbation so I thought I had some type of infection but was paralyzed with fear! I tried it the next day and same result! This was Christmas vacation and had no internet at my house so had to wait until the next Monday to figure out what had happened, I asked Jeeves (Dating myself here) and found out that i had masturbated and had my first wet orgasm! Been 20 years now!

 

[Latimer]

I don't remember how old I was, but I had a wet dream. My older brother with whom I shared a room noticed the wet sheet and explained to me what had happened.

I didn't start masturbating until I was twelve, my first year of Catholic boys' high school. The term began with a retreat during which one of the priests gave a sermon talking about sin and eternal damnation that I later realized--because it was on our reading list--was straight out of Joyce's Portrait of an Artist as a Young Man. Perhaps he was even reading from Portrait. You know, the one about eternity and grains of sand, etc., etc. that Stephen Daedalus listens to at his school. It was pretty terrifying. I figured the sin he was talking about was masturbation and I thought, well, if it's that big a deal that he's devoting a whole sermon to it, I need to find out for myself what it's all about. Just once, to experiment. So, one evening after taking a shower, I tried it standing in front of the mirror in my bathroom and realized what the big deal was, but told myself I wouldn't do it again. A few days later I decided I needed to verify the experiment--just once. A few days after that, I decided I needed to find out again if it was good as I remembered it and did so a third time. I was lost.

 

[PrinceCory]

Much like the OP, I was a young teen but I don't remember how young (remember I'm retired now, so I am old). But my first time was in the bathtub. We had no shower yet for our family of 7 all using one bathroom. I was adding warm water to the tub and the water was hitting my dick. I came from that water pressure sensation. Then in the future, in the tub, I started rubbing my dick between my palms (like you would roll a pencil back and forth in the palms) and that is how I learned to beat off. It wasn't until I had my own bedroom at the age of 16 that I figured out how to jack off the traditional way.

 

[nycguydowntown]

Wet dream - maybe 13.

 

[Reischfleger]

Oh boy! It is a bit embarrassing

Wrestling with a cousin that ended in a surprise. Had no idea what cum was until then

 

[rareboy]

Wow.

My first time with another boy...I had no idea what the fuck wa happening when he grabbed my cock and started to pull on it...but several months latanother bud taught me what it was all about...I taught him.....and we had about 6 months of fun together before he found girls.

 

[me203]

^Nothing like that ever happened to me.

When I learned as an adult that it's not uncommon for boys to do things like masturbate together, I sadly realized three things:

1. Part of me would have loved the chance as a teenager
2. But I'd have been too scared of AIDS to do it. (This was the 1980s.)
3. Then, I was so unliked that it wasn't like I'd ever have gotten the chance.

 

[72-Jay]

When was it?

A long time ago. I was probably 19 or 20.

How did it come about?

Jacking off for the first time.

I'll also add a 'where':
In my bed

(oh and I ate the little bit of cum that came out, so no mess made...)