Before sex with girls, I masterbated all the time. I always just used my hand, with no lubrication. It wasn't like I had instructions: it was a trial-and-error kind of thing (there is probably material for a mini-blogpost in that subject). It wasn't until a lot of years later that I realized that guys usually used something for lubrication.
I was a kid living with my parents and didn't want to get caught so I tried to get it done really quickly. I even timed myself, and found I could regularly come in about 2 1/2 minutes.
Then one day I read about guys who came too quickly and how it left their partners high and dry. One theory for how they got that way was that they had been in a hurry when masturbating, because they didn't want to get caught, and they had trained themselves to not be able to last a long time. This was of course familiar to me and the last thing I wanted to be was someone who couldn't satisfy their partner. I started training myself to last a long time when masterbating. Soon my masterbation sessions were taking maybe 45 minutes.
When I finally started having sex with girls, I found that they really turned me on and that I loved licking them, but fucking them wasn't that satisfying to me. Its no surprise now really, I had trained myself to need a lot of stimulation and a lubricated pussy wasn't the sensation I needed to come. I probably have only come once or twice my life while fucking someone.
The fact that I couldn't come while fucking a girl meant that I didn't have the problem I had worried about (coming too quickly). I could always fuck her until she came. It did raise a question most guys don't have to worry about: when should I stop fucking her? Its an awkward situation.
To come, I ended up masterbating after we fucked. I think this made my girlfriends tend to feel like they hadn't really pleased me even though I reassured them that sex followed by masterbating led to better orgasms for me than just masterbating. And it was true.
I remember having a girlfriend tell me that I approached sex like no other man she had been with. She wasn't saying it judgementally, she loved having sex with me. Now I think that if she had been with a woman before, she would have said that I approached sex like a woman.
When I got older, I started getting more adventurous about exploring my feminine side, including putting dildos and butt plugs inside of me. It felt good, but in the end, it often didn't feel worth the work and the mess.
When I finally had sex for the first time with a transexual, it was a revelation for me. I discovered how much I loved sucking her cock and being fucked by her. There were no drugs or alcohol involved, but when I got home and parked my car, I was in such a daze that I walked into the my car mirror and bent it backwards.
While she was (is) a woman, a beautiful woman, she brought a man's urgency to sex. Being on the receiving end of that was addicting. If I never fuck someone again, I don't think it will bother me at all.
I haven't been fucked as much as I would like, but a couple of times, I thought I was close to coming just from being fucked. That would be a level of emasculation I can only dream about so far.
