Disclaimer: I do not own anyone or anything from Gossip Girl!

Would I be focused on my pleasure tonight or Blair's? That had to be one the hardest question a man could be asked. You see there were pro's and con's to each side of the metaphorical coin. For instance if I was a gentleman and chose to focus on her pleasure I could make sure that she would never forget me. I am not one to brag, wait a minute, I am so the type to brag so I say right out that Blair Waldorf will be screaming her head off in all the best ways if I decide to play nice and for once not be the selfish bastard my father had molded me in to. It would be one way to ensure that Nathaniel was the last thing on her mind tonight.

On the other hand if I chose to direct the queen of Constance in how to give pleasure well I was sure she would be the best possible student I could ever have. I could turn her in to what I wanted and seeing as how I was toying with the idea of making her my queen I needed to be sure that my chosen queen would be able to please her king. Ah there were so many choices in front of me. I supposed that I could be selfish for one night. Who knows? The brunette female may actually end up liking this and that would only be good for me in the long haul. With a smirk I pulled my lips from hers and trailed my index finger down the column of her throat.

"I must say that I am torn as to what lesson I want to teach you first." I stated slowly drawing out my vowels as I slowly let my eyes flicker up and down her form letting her know that I had many different scenarios flashing in my mind. "Knowing dear Nathaniel as well as I do I find it hard to believe that he has actually ever brought you pleasure. Tell me Blair do you even know what an orgasm feels like?"

Immediately her face turned bright red with both embarrassment and anger. "How dare you ask such a personal question? What Nate and I have done in the past is none of your business!"

My smirk only widened as I continued to run my fingers down the length of her pale throat and shoulder. "On the contrary Waldorf I feel like it really is my business. Look at it this way if you will. You are the one who came to me and therefore it shows me that either you were desperate or you wanted someone who could give you something your dear Nate could not. Since I know you did not come to me out of desperation I know it has to be the second on my list. I bet you have to fake it don't you? Well that is if you even get that far with him. Since he has a big mouth when stoned I know you've sucked him off and he says you are quite talented with your mouth. Funny it is the only time he has ever really complimented you before."

"You're a sick bastard do you know that?" She snapped raising her arm to hit me, but I anticipated her move and caught her arm before it even came close. "I hate you."

"Yet you asked me to take your virginity." I shot back with a raised eyebrow before I tugged on her arm slightly extending it so I could run my tongue along the smooth skin of her elbow. "You like that about me though don't you Blair? You like how I am not intimidated by you. You like the challenge that I offer. You may pretend to hate me because it is what is expected of you, but deep down you respect me for not backing down. Someone finally standing up to you and not bending your will sends a thrill down your spine as well as other places I am sure."

Her expression crumpled in to one of utter disgust though her heart rate sped up drastically. I'll give her points for being one hell of an actress when it comes to hiding her emotions under a mask of hatred. "You are sick and I can't believe that I came to you. I have no idea what I was thinking-"

I cut her off while running my left hand up her thigh letting my fingers brush against her panties. "I know exactly what you were thinking. You were thinking that I am not Nathaniel and that is what you need. Now shut up and put your mouth to good use or let me put mine to good use. Don't bother pretending that you want me to leave because you and I both know it is the last thing that you want."

For a brief moment I thought that she may actually ask me to leave. My fears were put to rest though when she grabbed the collar of my shirt and dragged me to her. I actually enjoyed this rough side of her and I was ready to sit back and see how this played out. "You want to see what I can do with my mouth do you? Well prepare to have your world thrown in to chaos Bass because I am sure I will be the best blow job that you have ever had."

"I love it when you talk dirty Blair." I teased grabbing her chin between two fingers and squeezing before releasing her. "It really does turn me on. I have to say that I am looking forward to this life changing experience. Maybe if you do a good enough job then I will reward you. I am not a heartless bastard Waldorf and if you pass my little test I will make sure you get something much better than gold stars."

We had no need for words after that and hey it worked fine for me. Words were overrated anyways. Blair sat still for a moment as if she were debating with herself though I could not be sure considering her mind was not open to me. After a moment of silent debate she must have made her choice because she pushed me back against her pillows and kneeled between my legs. I have to admit that I hadn't thought she would really do it at first. I mean Blair Waldorf doesn't really give off the kind of impression that she is a girl who would sully her perfect reputation by doing something as low as giving a guy head, but then again it is always the ones you don't expect who end up being the crazy kinky (in all the best ways) ones.

I chose to focus all my attention on her as she swiftly undid my belt buckle and yanked down my zipper. She paused to look up at me. "You have Dior boxer shorts? I bought Nate a pair for Christmas, but he told me that they were not comfortable. Sometimes his lack in taste really irks me."

"He must not have worn them because I can say they are probably the most comfortable pair of boxer shorts I have ever owned." I replied before frowning slightly. All this talk about her boyfriend was not setting the kind of mood I had been hoping for. "For future reference it would best if you did not mention his name during these sessions. I doubt you would be happy if I spoke about another girl."

"Fine then I won't say his name again. I am done with talking anyways." My brunette companion stated with a wicked smile as she proceeded to pull down my boxer shorts along with my pants. Now we were finally getting somewhere.

TBC…

AN: I know I ended it in a cliffhanger, but I am tired and so this is what you get, but the next chapter picks up right where this left off. I do need to know if after Blair is finished if Chuck should give her a reward. *winks* Let me know what you all think.

Please R&R like always!