I don't know. Felt like writing a story. Got this far and feel like sleeping. Obviously, as aptly titled, this is just a beginning/idea that I will pursue further tomorrow.

First of all, I have a terrible habit of losing my overcoat. Secondly, I have a dreadfully pallid countenance—one which is often betrayed by my propensity toward blushing when affronted with the frankness of a female. If my disparaging whims betray a certain sense of dignity you believe a young gentleman such as myself should possess, I shall be the first to apologize and reconcile them. Though I may possess a “dreadfully pallid countenance”, that is not to say I am not at all attractive in anyway, as I fancy myself a fairly handsome fellow. I have “been with” (remember to inquire as to how a gentleman properly tells someone that he has slept with a fair amount of women) multiple women—women who have been quite sought after by many of my peers. It is not with the intention of impressing anyone that I reveal this bit of information, but rather; to reconcile any forthcoming self-deprecations with incoherent bits of confidence.

Look at me! already attempting to reconcile myself to my imaginary reader in order to convey a certain disposition with which I’d like to be associated with. Ugh! It is an awful habit of mine—one which betrays the essence of my character! I do not care if you find me disparaging! Nor do I care if you find it distasteful! I’ve never actually slept with a woman (‘slept with a woman’ must be the gentlemanly way of expressing ones escapades, or so I for now conclude). I’m hardly attractive. I cannot say with any certainty that I am ugly though, and I have at least been granted the privilege of touching the flesh of a woman (no I haven’t).

I know! How can I talk so forwardly about such discreet matters? It is because matters of the flesh hold little meaning. I am inclined to hold sacred an ideal rather than a tryst. To speak indiscreetly of an individual’s innermost “ideal” in the wrong company is much more a tragic betrayal of camaraderie than to disclose sordid details of a sexual affair.
I liked the first paragraph, but the change in character of the second paragraph ( the revelation, if you prefer ), kind of drove me away. I've always liked these kind of proses - a narrator dialoging with the reader ( my favorite book is The Catcher In The Rye ). And the tone is quite good, but I prefered the character on the first paragraph than on the next two. Still, I'd like to see where you're going with this.