how could I not?

[roostercog]

So I was hanging out with my girlfriend one day, right when we first started seeing each other. At this particular time, I was interested in finding out a couple things, first- what kind of experiences she had had, and second- what she liked, and was willing to do sexually. We were buzzed a little off a few beers so I figured now was a good time to get her to open up to me, and maybe a good chance to make the move. Well in retrospect I'd have to say I was a little buzzed..... based on the conversation I think she was a little drunk.
I started by asking what her favorite position was, in a friendly; joky but flirty sort of way. When she said it was doggystyle, I was thinking "nice". Obviously I love it, as does every man alive. I was also kind of curious about some of her past experience with other men, so I asked how many guys she'd had sex with to start, and she told me 6, which was close to the same as me and I thought that's not bad. I asked her if she had tried anal sex, and she said yeah, but only with one guy. It turns out I knew this guy, and I worked with a girl that had fucked him. I don't know exactly what caused me to say this, but I guess I was just trying to coax some info out of her that she may have been less than honest about if I'd tried another tactic; so I said "my friend Lindsay fucked him, she said it was ok but he had a small dick". She really never said that, but I was just curious to see how Jade would respond. What she said was kind of surprising, and also made me feel a little strange.
"What?!", she answered, "That is ridiculous! He has the hugest dick I've ever seen! Why do you think I let him fuck my ass?" I said I don't know, kind of taken aback, and she responded, "because he made me cum so much. His dick was so big it didn't even look proportionate to his body."
So here's the thing= me and Jade had taken a shower together earlier that day, so I knew she'd seen my dick, and she knew I knew... With this in mind, you would think most girls would play it off, or at least not make it clear that their ex had a much larger penis than you, just so as not to hurt your feelings. In this case, I think I pushed a little too hard for info while she was a little drunker than I thought.... or maybe not.
So of course I continued, " Do you think my dick looks proportionate to my body?" Bear in mind I'm much smaller than this other guy, so my dick being proportionate to my body would make it much smaller than his even if his was proportionate to his body. However she already said his wasn't, being way bigger than it should be. Well, her response to this killed me. She hesitated... for like 10 seconds. With a look and a tone that clearly said "trying not to hurt your feelings", she said "yeah yours looks proportionate".
As if the words were not saying enough, the look she gave me told me she thought my dick was too small for my body. This was very humiliating for me. This may have been where I realized I kind of enjoyed this feeling. At that moment I just felt that her experiences and just her overall sexuality was so far superior to me, like she was above me somehow, and it made me a little aroused.
Needless to say, I played the whole thing off like I wasn't bothered or turned on, both of which I was. We kept drinking and hanging out, and later that night, which was the second night I had stayed over with her (we didnt have sex the first time) I found myself in bed with this beautiful girl. She is about 5'2'', 100 lbs, a little curvy but very tight and very firm. Well I was pretty nervous, but she wasn't. She started making out with me, and started rubbing my dick through my pants, and after a minute I got hard. We had been talking about how we both love it doggystyle earlier that night, and it was great when she pulled away from me, stripped off her clothes, and got back on the bed on all fours facing away from me. I was fucking ready to go, so I got up and moved over to mount her.
It was at this point that she whispered out, "yeah baby, shove your little dick in me". I came all over her ass. She had said, "your little dick." Oh my god, I couldn't help it it. the comment instantly made me feel ridiculous and ridiculously turned on. She didn't realize what had happened for a moment, and when I lay back down she said "What's the matter, aren't you gonna fuck me?" It was terrible to have to say I had cum already. I felt like I had let her down so much. She just told me about how her last boyfriend had made her cum over and over, and here I wasn't even able to penetrate her before cumming myself.
Well I was right, I had let her down, but she wasn't about to let that be the end of it. Even though I have always needed some time after cumming before I am ready to go again, she insisted that she could get me hard again. Well, she was kissing me and stroking my soft dick for a good five minutes before I finally said baby, I need to rest, I can't get hard again for a while. She looked at me very puzzled and said, "I don't understand, every time Josh would cum I would suck his dick and he would be ready again in 2 seconds. He would fuck me 3-4 times until I couldn't even move!"
Bam.
I got hard.
I pushed her back over on her back, feeling good now, feeling ready again, and I penetrated her. Damn it felt great. After a second though, I realized, this doesn't feel like some of the other girls I've had sex with. Funny thing is, most of the girls I'd actually dated in school were either virgins or close to it. With these girls, when I put my dick in them, it felt like their pussy was really hugging my dick tightly, and with Jade, well..... it didn't.
It was at this point that I looked down at Jade's face, and she was looking up at me with no expression other than a hint of some emotion I later realized was her slowly realizing what she was NOT feeling, which was pleasure. I came.
I got up and tossed my second condom in the trash, and lay back down feeling very much defeated and inadequate. Jade snuggled up next to me, like she was trying to make me feel better and let me know it was ok. I shouldn't have asked but I did- "How was it for you?"
She looked like she didn't know how to answer for a second, but said, "I guess it was ok"..... "But do you mind if I masturbate? I'm just really horny and I want to cum".
I didn't know what to say, so I just said sure. She rolled on her stomach and started touching herself, and she looked so sexy I leaned over to kiss her. She seemed kind of annoyed, like I had distracted her, and turned her face away. I was still sitting there feeling useless so I leaned down and started placing some soft kissing on her back and legs and then finally on her beautiful, sexy, perfect ass. "That's it baby," she moaned, "kiss my ass. I like it when you do that"
I kept kissing it, cuz goddamn, it is a phenomenal ass, not to mention I wanted to feel useful in any way I could. She started moaning a little louder, and right when I finally swiped her tight asshole with my tongue, she exploded in a beautiful orgasm, bucking and moaning against my tongue while I fucked her ass with it as deep as I could. When she started to come down from her high, she moved so that my mouth slid down to her pussy, and I ate her for a long time, while she came once or twice more. Finally I realized she was asleep, so I stopped.
I had a raging hard-on at this point, I had gone down on her for almost 2 hours until she passed out. Well, I thought, I'll wake her up with a nice surprise! So I lifted myself up, put my legs on either side of hers, which were close together, and slid my dick into her sweet pussy. She didn't wake up, she didn't move, there was no reaction whatsoever. I realized then she couldn't feel me at all. I was so turned on that I knew if I really started fucking her I would cum, so I just slid in and out as slow as I could, and tried to enjoy it as much as possible. This later became a problem in our sex life, as I always get so turned on by this girl that I know I'm gonna cum, and I try to go as slow as I can so I can enjoy it for more than a couple minutes. The problem is Jade loves to get fucked hard, and with my lack of equipment I need to Really ram her for her to get any pleasure from it. Of course if I do I get too much pleasure from it and can't keep it up long enough to make her cum even once, and I never have. It's even gotten to the point where she will express her boredom after unsuccessfully trying to make me fuck her hard, and she sometimes even falls asleep in the middle of me trying to fuck her. This is very embarrassing but it seems like my dick is always so much harder with this knowledge. I really love my girlfriend.