Recently, I was discussing with a friend of mine about our first time having sex. Many of us, even though we are gay, had our first time with a woman. I will admit it, I am not a gold star gay, I have had sex with women. I thought it was the path I was supposed to go. I fantasized about men, but I never thought it was possible to actually let it go any further than fantasy. I am very thankful that I realized that I was wrong about this. This is the conversation we had about our first time:
ME: The first two times I had sex with women sort of defined my ideas of sex. The first time was a lot of fun, far too brief, and with a condom. The second time (and there is a lot of emotional baggage attached to this time), it was without a condom, and it just felt nasty to me. I like the feel of lube, especially silicone-based lube because it does mirror that silky feel, but it was just something about the vaginal juices that just grossed me out. I've tried to go down on women, but the greasy feeling of pubic hair/vaginal region just really turned me off. I've never understood it. That second time, no matter how hard I tried, I was never able to have an orgasm. The ickiness of the feel, and the fact that she was very loose and wet, just didn't allow me to reach orgasm, and we went at it for a while. Is it just me, or do other guys get turned off by this? I assume a lot of gay guys do, but I really would like a different perspective on this. I have had sex with women since those initial two times, but I guess all women have unique vaginas like men and the uniqueness of our penises.
HIM: I was drunk as a skunk my first time fucking and eating a pussy and couldn't even find the hole [fucking wise] - was aiming for the right area but couldn't plant my dick in it. It wasn't a good experience for either. I felt [right after] a complete failure, in the "male" dept. She had to lead my dick to her hole. I wasn't all that hard to begin with. The whole affair was, in my mind's eye, a complete failure. Needless to say, we never continued dating.
ME: I totally understand the trying to find the hole part on the first time you fucked a girl. I am right there with you. It is very difficult the first time. I wonder if all guys have that problem. It's very embarrassing, but oh well, you eventually get over it. When I was older and had sex with a woman again, it wasn't so difficult. Just glad that I wasn't the only one who had that happen their first time.
HIM: I am convinced that every guy the first time he has sex will fumble in some way. I don't care how macho he considers himself. I'd never seen a pussy before and I sure wasn't acquainted with the pussy anatomy - I just thought it was a hole of some kind. And for me the first time was in the dark. It's not like I could look for it or anything. Hell, I didn't know what to be aiming for in the first place. If it's your first time - you just don't know. But after a couple of times you learn how to geolocate one with just using your dick. The pussy hair doesn't help. It hides everything. That's why I so love having sex, exclusively, with another guy. I'm 100% familiar with the equipment, I know what it does, and I know how it works and what works it
The first time I had sex with a guy, I had not problem finding the equipment. The first time I fucked a guy, my dick slid into his ass as naturally as it could be. There was no fumbling, there was just perfect harmony. This may be because I had had sex with several women before this, but I do think that we are more familiar with a man’s body.
So my questions are these: Was your first time with a man or woman? Was that first time awkward? Was it easier when you compared your first time with a man or with a woman? Why? I would love to know your answers guys. I am curious to know if it is universal that the first time is always awkward or if some of us are just born with the ability to be a great lover.