Anyone else ever teach someone how to reach orgasm? I have. I thought it was very hot to teach someone how to enjoy orgasms! Made me so horny I nearly had a spontaneous orgasm just watching them get there! Anyone else have a similar experience? Here are my stories about it:


I was 5 years old when I discovered masturbation on my own and experienced my first dry orgasm. I had a regular jack-off buddy by the time I was 6. Even though I started young, I only had two opportunities to show a buddy how to get the best feeling a guy can have. I also had the opportunity to teach my first girlfriend back in high-school how to masturbate to orgasm. Decades later, I had the opportunity to teach my fiance how to bring herself to orgasm via self-stimulation.

Here's my first story:

A group of friends & I would sometimes masturbate together on sleep-overs & Boy Scout camp-outs. One of the guys never participated. One day while we were at my place, he asked me what 'jacking off' meant. I was 15 & he was 14. I explained it to him, and then asked him if his penis ever got hard. We were in my bedroom at the time. He pulled down his pants & showed me his hard-on. I noticed that his penis was still really small, he didn't have any pubes yet, and his balls hadn't descended.

He asked me to show him how to do it, so I dropped my pants & started stroking. He tried to do it, but said it wasn't working. I asked him if I could try. He said yes. I noticed that his penis was very tight. He had no loose skin at all with which to stroke. I guess the doctor that circumcised him must have removed way too much foreskin.

He wanted to see me orgasm, so I jacked off & finished. He was trying to do it, but still said that it wasn't working for him. He also said that it hurt a little. I went to the bathroom & got some Vaseline for him to use.

Once he had some lube, he was able to masturbate. He experienced his first dry orgasm about a minute later! He was very surprised! This made me so horny, I masturbated again, and came in about a minute. He then asked me about the white stuff he saw when I orgasmed, and wondered why he didn't have any.

I explained the whole puberty thing to him. I thought it was a bit unusual that a 14-year-old guy could be so naive about sexual matters. I put things together when I was about 8, after reading my older sister's college book on human sexuality. But then I was the curious type. I guess nobody had 'the talk' with my friend. Evidently, he had not been curious enough, nor did he have the hormonal drive to learn anything about sex up to that point.

No particular reason, but we never masturbated together again.

My second story:

One of my other classmates & I also masturbated together on occasion. We were 10 the first time we did it together. I noticed that he would quit masturbating shortly after his penis got hard. I asked him what was up with that. He said there was no point in continuing until he was old enough to shoot sperm. He thought that guys couldn't have orgasms until they could shoot! I told him about the wonderful, super-intense dry orgasms I had been experiencing since I was 5, and I told him to keep on going after he got hard. He did, and he experienced his first dry orgasm that day! He was also very surprised! We masturbated together on occasion after that - until we were about 16.

My third story:

I also introduced my first girlfriend to the wonders of orgasm. The first time I fingered her, she had an intense orgasm. She told me that it was her first, and that she had never masturbated to completion, because she thought it was 'dirty'. She changed her mind rather quickly.

My 4th story:

Many years later, I also introduced my fiance to orgasm through self-stimulation. She had experienced many orgasms while having sex, and was multi-orgasmic. She also said that she remembered putting the phone-book in her lap & rubbing on it when she was 8-9 years old, and that she did have orgasms while doing that. However, she said that she had been unable to bring herself to orgasm since those days. So, I did my best to help her out!

Mutual masturbation was always a part of our sexual relationship. She came easily when I fingered her, and often experienced multiples in the process. But for some reason, she couldn't orgasm when she fingered herself.

During one of our mutual masturbation sessions, she decided put her hand on mine so she could figure out what I was doing that made her feel so good.

One day when I came home from work, she was very excited. She told me that she finally did it - she gave herself a powerful orgasm! We celebrated by spending the rest of the day & night in the sack!

I learned to masturbate from my older cousin, then passed the "secret" down through younger generations. It was about what you'd expect from kids fooling around together.

Much later, I did wind up having quite a time with my college roommate over a year and a half. I obviously didn't teach him about masturbation, but we did spend quite a bit of time discussing the relative merits of Playboy vs. Penthouse magazines (this was in the 1980s when the two were in "hot" competition--he liked Playboy I was all about Penthouse).

These talks eventually led to us sharing magazines and masturbating together. Maybe the "educational" component here is that I taught him something about the virtue of stroking to sluttier girls?

I taught my cousin how to wank. We were both eleven.

I've never viewed it from that perspective.

Assuming that every person knows how to masturbate
by his or her own means, I try not to 'teach'
someone how to masturbate; because I don't want to
appear as though I were insulting said person
in some way, regarding 'how to masturbate'.

However, when I'm with a buddy who is giving me
a BJ or a HJ, I like to verbally coach him
along the way of how I like to be pleased.

And whenever I handjob a guy I like to verbally
coach him on how to enhance his receptiveness
and sensitivity to that pleasure...
...how to relax, how to breathe, stay focused,
how to hold back, when to release, PC muscle Control,
and whatever else comes along.
And I also enjoy listening to the guy coaching me.

It makes for a nice quiet or low-volume conversation
during the session.

To clarify -

I'm not talking about attempting to "teach" or coach a sexually-aware friend who already masturbates to orgasm. That's a whole different deal.

I'm referring to actually teaching and/or helping a friend or girlfriend who had never masturbated before and/or wasn't aware of what masturbation was, or had tried it & was unable to climax, experience their very first orgasm (or at least their first orgasm from self-stimulation) - similar to the 4 stories in my original post.

When I was in high school I was cleaning out my room and found a bunch of old worn out cum covered porn mags and I put them in a garbage sack to throw out. When I went to the trash can, I ran into my 12yo neighbor. He was a shy kid with no friends and he always looked up to me. I asked him if he wanted the bag of porn mags and told him "watch out, they are covered with lots of my cum". He had absolutely no idea what I was talking about. I could tell. I asked him if he could ejaculate yet. He had no idea what I meant. Then I asked him if his dick got hard and he said it did. Then I asked him when he jerked off if he got that "tickling feeling" that felt good. He said no.

I felt so bad for the guy and my cock was rock hard, so I asked if he'd like me to show him how to have an orgasm. He said yes, so off to my room we went. I showed him how to stroke it and what cum looked like.

A few days later he came running up to me and said, "I did it! I squirted!". I felt like I changed that boys life.

I had a buddy and we would hang out together talking about sex. One day we both got obvious boners in our shorts. There was no one home at his house and he suggested we go over there and compare our dicks. We went there and stripped down and fooled around. I asked him if he wanted to jerk off and he said he didn't know what that was. So I proceeded to demonstrate and then he tried it. He moved away after that. I wonder what he's doing now?

Yep sure have, can't discuss it here but I taught a M and F. at different times of course.

I've had this opportunity a few times! The first time I've posted on another topic, but here it is again!

My friend Justin when we were 10. Swimming at the pool in his apartment complex, I introduced him to the wonders of the water jet after he caught me mid-spasm! I watched as he clung tightly to the side of the pool. "It feels so good!" he panted, "but I have to pee!" I told him to keep holding it there and watched as his face scrunched up and he started to shake. I knew he was getting "the feeling!" The same feeling I had discovered years earlier! That night in his room he told me he couldn't wait to go swimming tomorrow and get the feeling again, and that his dick was stiff again just thinking about it. I told him he didn't have to wait that long. My penis was hard too so I pulled my pajamas down. Justin did the same. I showed him how to rub it. (At the time I was using my middle 3 fingers to rub the underside of my penis.) I told him it was more comfortable when you're lying down, so we both climbed into his bed. We laid there for a few minutes rubbing our penises and telling each other what felt best. Justin finished first. "Oh God!" He groaned, "it feels so g-uh, uh, Aahhhh!" I came right after. Something about hearing him groan like that and watching his face and body twitch, made mine feel better than it ever had before!

A couple years later, in boy scouts, I showed my tent mate the wonders of masturbation after he asked why I was rustling around in my sleeping bag. We both came a couple times that night and were tent mates on almost every campout after!

Nowadays, most people I come across have figured it out, but I still get off telling and showing people new ways to do it! It's amazing how many guys think hand to cock is the only way! I have a full toy chest and I love introducing boyfriends to fleshlights, Tenga eggs, and vibrators!

My favorite is watching a guy experience his first vibrator induced orgasm. I love watching the scrunched up face, knowing the intense sensation he's getting. They always tell me that they've never cum that hard before!

When I was around 11, my brother had showed me how, but I spent the night with my best friend, we was laying in the bed watching tv, he was in his side facing tv, I was on my side facing him and tv. I got later an info excersize commercial was on, my cock got hard quick. My buddy Josh was sleeping, I rolled over onto my back slide my shorts and undies down then slid cover down my hard thin little 3 1/2" cock was pointing at my belly, I slowly started using my fingers to stroke it, I closed my eyes to imagine stuff, next thing I know I hear Josh go what the hell are you doing? I look he has turned some looking at me. I said I'm jacking off bud you ever heard of it? Josh said no what do you mean? I can't explain it my brother taught me and it makes you feel amazing. Hell I could show you bud I'm telling best feeling ever. Josh said ummmmm I dunno bud. I continued to stroke and moan some. Please I'm telling you, you will love it. Finally he said ok what do I do? Lay on your back, he does, I moved cover back, then hooked fingers in his waistbands and pulled his shorts and undies off. His cock was standing erect at least 6 inches uncut.My draw dropped, why is mine bigger bud, I dunno but that's a big cock.now what? Just let there I will explain and do it for you so you know what to do. I reached out and grabbed his nice, hot, throbbing shaft, I slowly started stroking. Mmmmmm that does feel good, I started pulling his gore skin down and up he moaned. Then I said how's that feel buddy, so good so good, I then leaned down and pulled foreskin back and started licking the head, he was really moaning, then he shot two little gobs into my mouth, we continued to play for several years