Author's Note: My first story, please be gentle!
Chuck spun back and forth slowly in the worn leather chair behind the headmistress's desk and smiled to himself. If everything went according to his plan, she would be here any minute. She being Blair, the girl he was messing around with behind his best friend's back. He didn't mean for their indiscretion to be any more than a one-time thing, but Blair was making it very difficult for him to stay away from her. There was something intoxicating about seeing the fiery sex goddess unleashed from the most prim and proper girl on the Upper East Side. Blair was an apt pupil, learning every nasty little trick he showed her perfectly and eagerly. Chuck was starting to get hard just thinking about it. But wait, here she was.
Blair knocked on the door and then entered the office hesitantly when she heard no reply. Her eyes narrowed slightly when Headmistress's chair spun around to reveal Chuck Bass. "Chuck? What's going on? I got a note to come here to discuss my grades." She noticed Chuck wasn't dressed in his St. Jude's uniform, but rather a very nice grey suit with and aubergine tie and he was wearing glasses. Something was up, Blair knew.
Chuck smiled his devilish smile and folded his hands onto the desk. "Miss Waldorf, your headmistress is out for the rest of the day. I'm here to go over the application process for Yale. We are very interested in you and understand as a legacy you will be applying to our school next fall. Please take a seat and we can go over the details ." He motioned to the green velvet love seat in front of the mahogany desk.
So he's playing a game? Blair sat slowly making sure to tuck her skirt under her and faced Chuck openly, giving him an inquisitive look before going along with it. "Of course, Mr. Bass. I've been expecting this interview for quite some time." She smiled warmly and crossed her stocking-clad legs appealingly.
Chuck eyed those silky legs for just a moment more than would be considered appropriate and swallowed before speaking. "Miss Waldorf, your records show you are an excellent student, in the top three as far as grades go but I believe you have what it takes to be number one. The problem is that I'm not sure the admissions office believes it." He tapped on a folder lying on the desk in front of him.
Blair nodded seriously, "I know I can get there. If I could only show you how dedicated I am to making this happen . . ." Blair face actually flushed with purpose, she would get into Yale no matter what it takes!
Chuck listened thoughtfully and seeing her earnestness, he took his chance. "Miss Waldorf please get on the desk." He patted the wooden top.
Blair's soft brown eyes widened but she did as she was told, and sat daintily on the edge facing away for him. Chuck stood up and then and walked to the other side of the desk until he was standing directly in front of her. "Miss Waldorf, I need to be sure of how much you want Yale." Gently he grasped her thighs and spread them apart slowly and moved even closer between them. Blair looked up at him with shining hot eyes and hooked her high-heeled legs around his hips. "I need Yale, badly" she said and ran her hands up his arms and over his shoulders ad through his hair to pull him in for a slow but searing kiss.
Chuck moaned as he felt Blair's warm open mouth press against his. He allowed her tongue entrance, and reveled in the half tantalizing, half agonizing feeling of her hot little tongue stroking his. Chuck was surprised that his glasses were actually fogging up from the heat of their kiss. His hand instinctively drifted up her plaid skirt and brushed over the thin triangle of cloth that covered her sweet pussy. He could tell she was already wet from that gentle stroke. She sighed at his touch and pressed herself against his hand over and over, trying to create some friction. With some regret, Chuck removed his hand and took a step back to look at Blair's face. Blair's eyes were somehow darker than usual with lust and her cheeks and lips were tinged rose pink and red.
"Miss Waldorf, you do seem to have some of the attributes we appreciate at Yale but I haven't quite made my mind up." Chuck removed his jacket as he spoke and laid in over the arm of the love seat. He walked back to the leather chair he had been sitting at when Blair first arrived in the room and sat down once more. He pretended to be seriously thinking over Blair's credentials. Really he was thinking she had better get naked quickly but he was playing a game and it was Blair's turn to make the next move.
Blair sat up from the desk and walked towards the office door slowly. As she did she unzipped her uniform skirt and let it slide to the floor. She felt Chuck's eyes rake over the view of the lower half of her lingerie set and felt herself grow wetter with every step. The deep blue panties and garter belt she wore to match her uniform were visible now along with her black Falke stockings.
Blair locked the door and turned back around to walk back toward the desk, removing her neck bow and little white puffed-sleeved shirt along the way and leaving along with black heels.
Blair never broke eye contact with Chuck as she climbed onto the table and sat directly in front him. She let her legs come to rest on either side of his. "Mr. Bass as you can see I have many admirable attributes."
Chuck's hands slid up Blair's slender thighs. "Yes I can see you do. There are two attributes in particular I am interested in a the moment however." He looked meaningfully at her breasts and Blair obediently removed her lacy bra and leaned forward so Chuck could get a better view. His hands were warm as he cupped her breasts firmly in them and his mouth was even warmer as he took one aching nipple into it and began sucking and licking her tits the ways he knew she liked it. Slowly at first and then ever so gently nipping at them.
Blair cried out a soft cry of pleasure as the feelings at her nipples sent a similar sensation to her thrumming clit. Her body buzzed with excitement at the thought of what would come next.
Chuck couldn't take much more of this teasing and looked stood up to look down at Blair. "Miss Waldorf, I need to be sure you can fuck like we do at Yale." He unzipped his pant and his cock sprang forth eagerly. Blair slid off the desk and dropped to her knees in front of him, taking his cock into her mouth as she also slid her little hand up and down his length. Chuck's head rolled back as his hands tangled in her hair. He moaned as she swirled her tongue around him sensually while she hummed "Boola Boola". No, he knew he couldn't continue this way or he would come too soon. "Stand up and turn around," he told Blair huskily as he began removing his pants.
Blair stood up and turned around, bending over to place her hands on the desk. Chuck quickly pulled her panties off and she felt his length sliding between her wet lips. "Now I'm going to see if you can take dick like a good Yale slut." He slammed his cock deep inside Blair and she cried out in ecstasy. She loved that feeling of being filled up with Chuck's glorious cock. It was the only reason she could think of why she had allowed herself to continue meeting him like this.
Chuck was always surprised at how tight and wet and perfect Blair was. "You dirty girl," he called her, "Do you like this?" As he continued thrusting into her over and over, he brought a hand forward and thumbed her swollen clit in time to to his thrusts.
"Fuck. Me. Harder." Blair urged as she rocked her body back to meet his thrusts. Chuck couldn't help but oblige as he began moving into her at a frantic and desperate pace. "So good." he murmured into the shell of her ear as he sucked on one of her velvety white earlobes. "Chuck! Chuck!" Blair cried as she felt herself come undone.
Chuck felt Blair clench around him in her climax. He was almost there himself but not quite. Blair's breaths came out raggedly as Chuck continued thrusting into her. She whimpered softly as he wrapped her long chocolaty waves around his hand and pulled her hair back while he fucked her. His other hand caressed her pert ass. Chuck felt almost at his breaking point but he wanted to look at Blair's face as he came so he withdrew from and lightly slapped her ass telling her to sit back on the edge of the desk.
Blair quickly did so and grabbed him for a rough kiss. She seemed to be getting very worked up from this little game. Chucked continued playing, "now Blair, if you can come one more time before I do I am going to go ahead and mark you down for early admission. But I don't want to make it too hard for you because I do like what I've seen so far." With that he began lapping at her pussy and Blair cried out louder than she really should have given that they were in school, She bit down on her lip to quiet herself. Chuck was amazing at this she had to admit. "Almost there," Blair panted out and Chuck knew it was close so he once more began to thrust into her and they exploded together in a blaze of fireworks.
Even though he didn't intend to, Chuck had his eyes closed, trying to feel the most pleasure possible and Blair did the same. They stayed connected for a moment and held each other through the tiny waves of post orgasm pleasure.
"Mmmm," Blair said appreciatively "you now, I kind of like those glasses on you."
Chuck laughed and began buttoning up his shirt. "Well, don't get used to them, next time you're the one dressing up. Unless of course you want to borrow them for that."
Blair thought about it while she redressed. "I really can't imagine what I would want to dress up as, this really hit the spot for me," she let out a wistful sigh, "Yale and sex."
He let a low chuckle, "Well I must say, you give great interview. You could make Larry King cry."
Blair made a face, "Gross, I do not want that visual. Me interviewing with Larry King." She shuddered for effect and then smiled softly at him. "Well I really need to get back, my committee for the charity trot in the park is useless without me. But you come over later if you like, Eleanor won't be home until very late tonight, she has dinner with a buyer. I might even have a surprise for you."
Chuck grinned at her. "Of course Waldorf. I wouldn't miss it." He watched as she adjusted her headband back to perfect placement and left the room. Then Chuck sank down onto the velvet love seat and pulled a joint from his inner coat pocket. After a rendezvous with Blair he always had a million thoughts that he didn't know what to think about.
Blair smiled to herself as she walked down the empty hallway back to her classroom. She did have her Halloween costume - Little Red Riding Hood. Chuck would make an excellent wolf.