Dr. York and Nicki Pt. 03 - Chaperone

"So why do I need my shoes on?"

"After I peel that dress off you it will be the only thing l plan to hold on to for leverage when I slide my rock hard dick into your ass!"

Nicole was taken aback. York had never talked about fucking her ass before. Sure he had given her the most amazing rim jobs and fingered her butt hole but he had never tried to penetrate her ass with his dick. She had said she wanted him to be impolite. She could already feel the wetness dripping out of her pussy onto her thigh.

"Cat got your tongue?" He asked. York knew he had caught her off guard with that comment.

"But first," he continued, " I want you to come in here and let me devour that delicious cunt of yours."

York reached his hand out for her and led her into the room. He didn't let her get far into the room. He closed the door behind him and pulled her close into him. He kissed her deeply. She responded in kind. The weeks without touching and tasting each other was overwhelming both of them. They continued to kiss until a flicker of reality distracted York.

"Isn't your roommate going to miss you?" A little nervousness in his voice.

"She's my roommate because she uses a sleeping aid to go to bed. Godzilla could walk through the room and she wouldn't know."

That was all the comfort he needed. With that piece of comfort neatly locked away York slipped his arms down to the bottom of Nicole's dress. Slowly he pulled it up until it was just below her pussy and her ass. He slid one hand around to her ass and the other stayed in front to explore the folds of her cunt. As he did that Nicold interrupted him.

"You know we're not in your office. We can use that perfectly good bed over there."

Without a word York scooped Nicole up. He wrapped his arms around her waist and she wrapped her legs around him. Her tits smashed against his chest. She buried her face in his kissing him deeply and biting his lips. York carried her to the bed and stood her up at the foot of the bed. He set her down carefully. He returned to the dress and slowly dragged it up over her head. He took his time so he could feel her skin from her hips to her shoulders. Then he took a step back. He wanted a full look at her. There she stood. Naked. The moonlight lighting her up like a painting. The heels forcing her up on her toes making her calves and ass accentuated because of the precarious position it put her body. Her toenails and fingernails painted a hot pink. He'd have to tell her how much he liked that color on her. He always thought she was more beautiful each time but this moment was special. And she was at her most beautiful.

"You might get tired of me saying this to you Nicole but you are simply perfect." He looked at her hungrily.

"Never." She returned the same hungry stare.

She closed the distance between them. Undid his pants and lifted his shirt over his head. She squatted down in front of him. Balancing delicately on her heels and in one motion swallowed his whole dick. She released it with a pop from her mouth relishing the groan she heard from York. She then held his dick to her face and licked him from his balls up the shaft and swirled her tongue around the head of his dick. Pulling the foreskin down to expose the head of his cock. She had sucked his dick so much she could draw it from memory. She knew exactly what pleased him. There were no more awkward moments figuring out each other's bodies. They each knew each other's bodies as if they had been together for years as opposed to weeks.

York looked down at Nicole with his dick in her mouth perched skillfully on her fuck me pumps as she stroked him in and out of her mouth. Her saliva building up on his dick until it was glistening in the moonlight coming through the window. Harder and harder she sucked. Her mouth was a little dirt devil at furious work to drain him of all fluids. Nicole reached under his shaft with her free hand and cupped and then squeezed his balls. Furiously sucking and stroking his dick while squeezing his nuts was bringing York close. He could feel that all to familiar tingling building. He reached down and ran his finger through her hair. He didn't have to push her head at all. He just loved the feel of her dark curly luxurious hair in his hands as she bobbed up and down on his cock. Nicole wanted his cum so badly. She had missed the taste of him. She knew how to make it happen. She slid her hands from his balls to his ass. She wasn't the only one who lIked a little ass play. With her finger she began to rub around his anus. He obliged by adjusting his stance to make his ass more accessible to her. He knew this would put him over the edge. She sucked him even harder. He was reaching the point of no return. She could tell. His ass cheeks tightened and his breath picked up in pace.

"Uunhhh!! I'm cumming!" He grunted and with that unleashed a huge load of sperm into her mouth.

Nicole never released her mouth from him. She sucked and sucked even when he started begging her to stop. His legs buckled and he bent at the waist resting his upper body on the bed behind her. Nicole still continued to suck his cock. It was less for him and more for herself. These weeks without him inside her made her desperate to not let him go. She couldn't bear not being without him. York was finally able to regain some awareness. He was slumped on the bed with Nicole pinned underneath him between him and the bed. Still crouching on her heels.

"We only have two more nights after this one. How about you give me a chance to return the favor?"

His voice brought her back. She released him from her mouth. He stood up and lifted her up to her feet. Slowly making his way from her neck downwards he kissed her all over. She languished in his attention to her. She ran her hands all over him. She could feel the strength in his arms and back. He used all of the strength in the most purposeful way every time he fucked her. It was a strength that made her feel safe. Protected. Cared for. As York made his way down to his knees he guided her onto her back on the bed with her ass just resting on the edge. The same desire to consume her as she had just done for him began to overtake him. He ran his hands down her legs until he got to her shoes. Wrapping each hand around the heel he pulled her left foot then right foot to him and sucked each pretty pink toe. She giggled for each toe. Her giggles only made him hornier. He raised her legs above his head and spread her open. Without hesitation he delved into the folds of her pussy. Sucking on the folds. Exploring each crevice. But he had a mission. He had a source of nectar that drew him towards the center of her body. When he found the nectar he sucked and licked as much as he could.

Nicole never tired of his mouth and tongue on her cunt. She loved that he loved to drink from her like she was a fountain. But then his licking and sucking became more intense. More focused. More centralized on that very important spot. He attacked her clit with reckless but determined abandon. York wanted her to feel the pleasure of an intense orgasm but he selfishly knew with her orgasm came more nectar. And he was desperate for more. He increased his intensity as groans began to escape her lips.

"Mmmm. Yessss. Goddd yessss. Just like that. Don't stop. Please please never stop. Eat me. Suck me. Devour me. Unhhnn yesss."

She was close he could tell. He wasn't going to deny her pleas. She had no desire to hold out and keep her orgasm at bay. She wanted to come fast and often.

He could feel her legs in his hands begin to push back. Frantically trying to make sense of the building fire within her loins. He pushed her legs so her knees were up near her armpits. Holding her in this way gave him more access to her clit. She couldn't clamp her legs shut when the orgasm hit. He could tell this realization was coming to her now. He held her open as the flow began to increase and the heat from her cunt rose a few degrees.

"Oh god don't stop. Yess! I'm cuuuuuummming!!l"

And with that Nicole flooded his mouth with more nectar than ever before. Her cunt just kept gushing and gushing. Her legs still held aloft York didn't stop his tongue attack on her clit. She tried to wriggle free. Pleaded for him to stop. She needed a break. She tried to pull away but he kept licking and sucking her clit. Then the unimaginable happened. Nicole started feeling the fire in her groin building. She couldn't believe she was on the verge of a back to back orgasm. This had never happened before. But there was the feeling.

"Oh my god you're amazing!" She squealed breathlessly. "I'm going to cum again. Please don't stop!"

Nothing could stop York. He was determined to have Nicole reach the highest peaks of pleasure. Her legs started to flay again. His grip on her high heels would not be broken.

"Unnhhhmmngggunnnhhh aieeee!!"

That definitely woke the neighbors York thought but he didn't give a fuck! Nicole collapsed into the bed still making unintelligible sounds. Breathing heavily and covered in sweat.

"What a first night!" She said in between deep uncontrollable breaths.

"What makes you think this night is over? I do seem to remember promising you I would be fucking that pretty little asshole of yours!"

York reached for her hand and slid it down his belly to his dick. Nicole couldn't believe it. His dick was already rock hard again. She rolled over onto her stomach and turned to look at him.

"Fuck away Dr. York. Fuck away."

York climbed onto the bed behind her and raised her hips into the air. Spreading her cheeks York pressed his face into her ass crack. She thought he was there to lick her as he usually did but she suddenly felt an immense amount of moisture in her ass. What the hell was he doing back there?! Suddenly it came to her. Lubricant! He was spitting on her ass. Wow that was a lot of spit. She could feel his saliva dripping down her ass crack to her pussy and some sliding down her leg. She felt movement behind her. She sucked in her breath anticipating the pain of her first anal fuck. But instead she felt his warm cock teasing her cunt lips. She had not even noticed how much she was also dripping cunt juices. The bed was going to be soaked.

York gently slid his dick into her pussy and held it there. They both moaned. Maybe it was the fucking on a bed for the first time instead of a desk or a rough carpeted floor but Nicole felt his dick deeper than he had ever been before. York was filling her up in spaces she didn't know she had. Had his dick grown on the flight to Chicago? York held his dick inside her for a while. Again she wondered what the hell he was doing. When was she going to clue in. More lubricant. His spit plus her pussy juices would coat his dick thickly. Protecting her virgin asshole. She always knew he would never hurt her. And this was proof. He didn't just mount her and pump away unconcerned about how it felt to her. Or worse wanting her to be in pain and enjoying and getting aroused by her pain. York was no ordinary man. He wanted her to have complete satisfaction in everything they did together. He became most aroused at her complete joy in their sexual acts. He was a consummate giver. He would never take. Unless she expressly told him to.

York slowly withdrew his cock from Nicole's pussy. He didn't want to wipe off her lubricant as he exited. He was going to need it to make sure this first time was as enjoyable for Nicole as any part of their fucking. York spread her cheeks some more. He heard her take a deep breath in.

"Let it out baby girl. I'm going to take good care of you. Perfect care."

And with that Nicole exhaled and all worry left her. She relinquished complete authority to him. He called her baby girl. He'd never called her that before. She knew they were on the verge of a new phase together. Then she felt it. Just a little pressure at first. She felt the tip of his cock pressing against her anus. She could also feel wetness landing on her ass crack and dripping towards her hole. Damn he could sure generate a lot of spit. For some reason she couldn't explain his saliva aroused her. She felt his cock come into contact with her anus and then hold. He was waiting for her. She gently pressed her ass back towards him. Burying her face into the bed and waiting for the pain. But there was none. His cock with the mixture of both their lubricants slowly but surely slid into her ass. York was in no rush. Her anal ring gripped his cock hard but then gradually loosened as Nicole relaxed more. Within moments his whole cock was deep within her. Again they just held their position. Frozen. York giving her the chance to get used to this new feeling.

Nicole had never felt full like this before. It was enjoyable but in a way she could not put words to yet. This was all so new. Then she could feel him pulling outwards. Not a lot and then pushing back into her. She matched his movements. His dick felt like a whole new thing compared to how it felt in her pussy. Slowly they picked up their pace. Not wild but a good steady in and out. She felt one of his hands caressing her back stroking her from where his cock entered her ass to her shoulders. Then she felt his other hand reaching around her hips underneath her towards her unencumbered pussy. He began to flick and rub on her clit. He was going to ruin her with all of this clit attention. She was not about to stop him though.

They were in a good rhythm now. Nicole enjoying the sensations in her ass and the building sensation in her groin as York rubbed her clit harder and faster than they were fucking. As the friction from his dick generated warmth in her ass there was a matching warmth building in her cunt. They didn't talk. Both wanted to be in this moment as much as possible. Their only sound was their breathing. The occasional moan. As the heat inside her built she pushed back faster and more deeply. York matched her movements. Soon they were in perfect sync. Nicole could hear York's breathing increase. He must be close. She raised herself up onto her hands. Dipped her hips. Turned and looked him square in the face.

"I want you to fucking cum in my ass right now! Fuck me damnit!" She ordered him.

That was all it took. York's head went back and he pushed into her as far as he could. Then he held it as the cum began to build in his balls. Nicole continued to fuck for the both of them. Reveling in the fact that her ass alone was going to make him cum. And then her wave hit her. She didn't realize he had not stopped rubbing her clit focused as she was on the dick in her ass. As her orgasm hit her York grunted deeply and unleashed a sizable load of cum into her. It made her insides feel warm. And with one last thust and grunt they both collapsed onto the bed together. York still inside her. She could feel his cock still twitching and shooting out small spurts of cum into her ass.

They lay there spooning with his dick shrinking and sliding easily out of her ass now with a third lubricant. Nicole reached back and held his neck. Pulling him closer to her.

"Baby girl?" She inquired.

"Do you not like it?" He asked.

"I love it as much as when you call my name."

They fell asleep in each other's arms. Luckily York was an early riser. His alarm went off at 5am. Hours before college students considered getting out of bed. He woke Nicole and helped her get dressed so she could get back to her room before anybody noticed. They kissed at the door and then York went back to bed.

York woke a couple of hours later. Exhausted but also energized. He couldn't believe there were two more nights ahead with Nicole. He got dressed in his usual business attire. Suit with bow tie and classic adidas sneakers that usually matched his bow tie. Today it was navy blue tie and navy blue shoes. After dressing he went down to the hotel restaurant where he had agreed to meet all the students for breakfast before heading out to the conference. They were all there. Including Nicole. All smiles. Her smile told him what he had hoped. She too was excited for two more nights. They all ate and discussed the days plans. Register at the conference. Attend morning sessions. Lunch would be on their own. Afternoon sessions. Meet at the conference lobby before deciding on dinner plans. The day went fine for York. He met some old colleagues and made some new professional contacts. He briefly saw Nicole between sessions and they simply said hello. They did not linger to talk. He was distracted all day thinking about her, waiting for the evening when he could be back in her arms again. Finally the day was over and York met all the students. They all had a good day and were eager to debrief over dinner. York was eager to eat Nicole's pussy.

During dinner York listened to the students relaying what they had learned that day. He did enjoy working with undergrads. The students decided they would do some more exploring that evening afterwards. They invited York but he politely declined claiming he had work to do. They dispersed and he went to his room to rest for the work he planned to do later. Not ten minutes later there came a knock on his door. He opened the door and there stood Nicole in a trench coat and what appeared to be taller bright red stillettos than she was wearing last night. She had taken a break during the conference to go buy new shoes. The look on York's face as he locked in on her shoes told her she had made the right choice. She promised herself that her extra money would go to establishing a 'fuck me pump' savings account.

"I suddenly came down with a stomach ache and had to bail on the outing." She said with a fake pouty frown while holding her stomach.

"Well maybe I can help you feel bet.."

York stuttered to a stop because Nicole had opened her coat. Underneath the coat she was only wearing her shoes. Completely naked. York's mouth fell open. No matter how much he saw her naked it was amazing every time. Nicole boldly stood in the hotel hallway displaying herself. Seemingly unconcerned if anyone should walk by.

"Well do you want me to stand out here all night or can I come in." She asked.

"Most definitely yes come in."

York let her walk all the way into the room. She stood with her back to the large window. Opened her coat again and let it drop to the floor. There she stood. Thank god for another moonlit night. Instead of walking to her York went to the bed and sat with his back propped up against the headboard. Not want Nicole had expected. She looked at him with confusion.

" I do remember you telling me during our first encounter that you would masturbate to my faculty profile picture. I'd like to see you do that with the real thing. So I'm going to sit here and you should make yourself comfortable in that chair at the end of the bed and let me watch you please yourself."

York stared at her deeply. Which she returned.

"So tonight is voyeur night?"

With that she sat back into the luxuriously soft chair. She lifted her left leg over the chairs arm and kept the right planted on the floor. If he wanted to watch she would give him full view.

"I have a bit of a confession", she began, "Because of me all of my housemates also masturbste to your photo. One of my housemates caught me and asked me to share the photo. She then shared it with everyone in the apartment. You might know her. Her name is Daphne. It has become something of a nightly tradition amongst us. And I think some of the girls have shared it with other friends on campus. You've been labeled 'King Of Masturbation Inspiration' or simply KMI."

For the first time York focused in on the tattoo on Nicole's inner foerarm. It had to be new. It was small and written in a fancy font. But he made out the three letters. KMI. Then York reflected back on tattoos he had seen recently on young women on campus. How many of them had the tattoo? He would have to place closer attention.