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  1. Whoa! Did That Actually Happen? I
  2. Whoa! It's Still Happening II
  3. Whoa! Sharon's Sister Susan Comes to Visit III
  4. Whoa! The Adventure Continues IV
  5. Whoa! Jason Attends Cheer Practice V
  6. Whoa! Ginger's Visit VI
  7. Whoa! Jenny's New Training Method VII
  8. Whoa! Susan Gets More Than She Wanted VIII
  9. Whoa! Susan Gets an Assignment IX
  10. Whoa! Jason and the Dean Make a Deal X
  11. Whoa! Ginger Visits Dean Malcomb XI
  12. Whoa! Professor Wayne Gets a Lesson in Manners. XII
  13. Whoa! The Orientation of Kelly Ann Black XIII

Whoa! Jason and the Dean Make a Deal X

Categories Fiction, Anal, Blowjob, Cum Swallowing

Author: Lucky Mann

Published: 15 January 2016

  • Font:

Whoa!
Jason and Dean Malcomb Make a Deal

The next morning Jason received a call from Dean Malcomb. “Jason, would you come to my office as soon as you can get free?”

“Yes Sir. I can come over right away.” Jason dropped what he was doing and hurried over to the administration offices. After all, when the Dean calls he expects a quick response. Fifteen minutes later, Jason was admitted to Dean Malcomb's office by a cute young receptionist.

Dean Malcomb rose and stuck out his hand to Jason. After shaking hands the Dean spoke. “Have a seat, Jason. I want to discuss something with you. First, how are you doing in your new position as our Lab Supervisor?”

“I'm doing well, Dean Malcomb. I am getting on well with the scheduling, and the paperwork is getting easier as I get used to it.”

Dean Malcomb hesitated for a few seconds, then continued. “Good! I knew you would do well in that position. Now for the real reason I asked you to come see me. Late yesterday afternoon I had a visitor here in my office. One of the cheerleaders came to see me.”

“Oh really, that's nice, but what does that have to do with me?” Jason asked.

“While she was leaving she said she was a gift from a grateful employee. You are the only employee at this university with recent reason to be grateful to me. Jason, be honest with me. Did you send Susan to see me and to do certain things for me.”

“Well Sir, as you may know, my girlfriend Sharon is a cheerleader. I may have mentioned to her that I felt a debt of gratitude to you for my new position here. Sharon may have said something to Susan who took it upon herself to come see you. What sort of things did she do?”

“Jason, I said to be honest with me. I don't think you have been forthright in your response. Now, try again!”

Dean Malcomb was closer to the truth than he realized. Jason knew he had to come clean with the Dean. But first, he sent a silent message. 'Dean, you really liked the gift of Susan I sent to you. As a matter of fact, you want more gifts like that. You will help me if I help you. From now on we will be honest with each other and not say anything to anyone else about our discussions.”

“Dean, I did send Susan over here. Did you enjoy her, Sir?” Jason asked.

“Oh yes! She was wonderful. She did things my deceased wife would never do. I have just two questions at this time. How do you get so many of the cheerleaders to do as you wish, and can you send more girls like Susan to see me?”

Jason smiled broadly. “The girls follow me because I want them to. They do my bidding because they want to. Yes Dean, I can send more visitors to entertain your needs. Is there any particular girl you'd like to see next?”

“Is it possible to have that tall redhead pay me a visit?” The Dean asked.

“You mean Ginger. Yes, she can come see you. Any woman on campus can be persuaded to come see you. All you have to do is let me know who you want to see. When would you like to see Ginger?”

“Jason, do you mean you can have any woman I want come to see me? How is that possible? Do you have some sort of special hold over women?”

“Dean, let's just say I can have any woman you like come to see you and do anything to please you. To prove it. Let me have Ginger come see you this afternoon. Will 4:30 be alright?”

The Dean seemed to be in shock. “That will be fine, but Jason, how can you promise that?”

“Let's just wait and see if I can get Ginger to come see you. Then we can discuss further what you can do for me. My two requests will easy for you to do. If I can give you what you want, all I want in return is your promise to say nothing about how you get so many young girls coming to see you. Then, when you come across a girl I can play with, send her to me, even if you have to order her to do so. I'd prefer they be virgins, but they don't have to be. That's it! Do those things and I promise you will have all the young girls you can handle. Do we have a deal Dean Malcomb?”

“I don't know what to say, Jason. Yes, I think we have a deal.”

“Good! Ginger will be here to see you later this afternoon. In the mean time, I noticed you have a cute young receptionist. Would you like a blowjob from her?”

“Jane? She's a great receptionist, but a twenty-year-old religious fanatic. She'd never do anything like that.”

“Very well. I'll talk to you later, Dean Malcomb.” Jason shook Dean Malcomb's hand again and sent another silent message. 'Dean, your cock will stay hard as long as you need it to please a woman.' He then left Dean Malcomb's office.

As he passed her, Jason sent a suggestion to the cute girl at the receptionist's desk. 'Jane, you will go into Dean Malcomb's office, drop to your knees, and give him a blowjob. Swallow it all when he gives you his cum. Then come to my home tonight when you get off work.'

Jane and Jason exchanged smiles as he passed. He then left the office. Jason noticed Jane rise and enter Dean Malcomb's office as he left the area.

Jason again attended cheer practice that afternoon. While there he sent Ginger a message. 'Go see Dean Malcome after you finish practice and have showered. Give him everything he desires.'

Ginger smiled broadly at Jason and nodded her head in acceptance of his suggestion.

That evening, a little after six o'clock, Jane knocked on Jason's door. He quickly invited her in. He checked her out as the twenty-year-old college sophomore stepped through his doorway.

Jane was dressed in the same conservative dress she had been wearing at Dean Malcomb's office. It was beige in color and buttoned from her waste to her neck. The bottom hem came to well below her knees. She stood about five feet six inches tall and weighed maybe one hundred twenty to thirty pounds. Her auburn hair was pulled back into a ponytail and exposed her cute round face. Her pale green eyes seemed to sparkle as she smiled. Her lips were just a bit puffy and looked perfect for kissing, or giving a blowjob. As Jason's eyes traveled down Jane's body, he noticed her breast for the first time. They were probably c-cups but were completely covered by her dress. They would certainly provide an enjoyable point of interest while exploring Jane's body. Her hips flared slightly indicating Jane was becoming a mature woman. Her butt caused a nice rise in the back of her dress.

“Welcome Jane, how may I help you this evening?” Jason asked with a broad grin.

“I really don't know why I am here. For some reason, I just felt I needed to come see you after I got off work.”

Jason laughed and replied, “Maybe it has something to do with the blowjob you gave Dean Malcomb.”

Jane gasped. “How...how could you know about that. I've never done anything like that before. I promise I am a good girl. I would never... I don't....” Tears were forming in the corners of her eyes.

“Oh but you did, Jane. It'll be alright. No one but you, Dean Malcomb, and I know about you giving him a blowjob in his office this morning. That blowjob was just the beginning. How would you like to learn how to be the best damned receptionist a man could ever have?”

“I think I'd like that. I really like my job, and it would be wonderful if I were the best at it.

Jason then silently sent Jane a message. 'Take your clothes off, Jane. I want to see your body.'

With tears flowing down her cheeks, Jane stepped out of her shoes. She slowly released the buttons down the front of her dress and let it fall to the floor at her feet. Her pantyhose were the next to go. After peeling off her pantyhose, Jane stood before Jason in nothing but her bra and panties. Her firm c-cup tits didn't appear to need much support from her lacy black bra. Her matching French cut panties accentuated her hips and firm butt.

“Very nice Jane, You look beautiful. Please continue.”

The girl took a deep breath and removed her bra and panties. Jason's first impression of Jane's tits had been correct. They didn't need much support. Her tits stood proudly on her chest and her nipples were erect. Looking down, Jason saw Jane had a large pubic bush that was auburn like the hair on her head.

Jason then sent her another silent message. 'Jane, you are a beautiful girl. However, that forest hiding your pussy has got to go. Go take a shower, and while you're in there, shave that bush. Do a good job and get it all. Then come back out and we'll begin your training to make you the best receptionist a man could ask for.'

Jason took Jane into his arms and hugged her. She resisted him at first but soon gave in to his advances and relaxed in his arms. Jane had begun to smile when Jason told her she was beautiful. She smiled even broader and sighed when he squeezed both of her butt-cheeks. He then gently swatted her butt and sent her to the shower.

Jane returned about an hour later looking refreshed from her days work as Dean Malcomb's receptionist. Her hair was freshly shampooed and again pulled back into a ponytail. Her pussy had been shaved bald as Jason had requested. And finally, she smelled even more enticing.

“Jason, may I ask a question?”

“Of course. What is it?”

“What does any of this have to do with making me the best receptionist a man could want?” She timidly asked.

“Well Jane, I assume you have all the secretarial skills for your job, but there is much more you can do to please your employer. Tell me Jane, did you enjoy sucking Dean Malcomb off this morning.”

“No! I don't even know why I did that.” She hung her head in apparent shame.

“There you have it, Jane. It's that attitude that will prevent you from becoming the most sought after receptionist/secretary. Before you leave here, you will not only enjoy giving your boss a blowjob if he wishes it, but you will happily let him fuck you, shove his cock up your ass, and even titty-fuck you.”

“Oh God, Jason. I can't do all that. My parents and preacher would never forgive me.”

'Jane, never mind your preacher. He isn't paying you. As for your parents, don't you think they want you to be happy and successful? Wait until they see how much money a really desirable receptionist/secretary can earn. From now on, you will willingly and happily allow me or your employer to make full use of your lovely body. You will also freely and honestly answer anything we ask you. Do you understand, Jane?'

Jane nodded then looked up at Jason and smiled. “Yes, I understand. I'll do whatever you or Dean Malcomb want me to do.”

In the mean time, Jason had taken his clothes off as well.

“Good girl. Now drop to your knees and suck my dick.”

Jane immediately lowered herself to her knees. She was afraid of the size or the cock that greeted her, but she did as Jason had told her. Her blowjob was a sloppy one at first. She simply bobbed her head up and down while sliding his cock in her loose mouth. Jane's blowjob quickly improved as Jason instructed her. She was soon sucking hard and swabbing Jason's cock with her tongue. She also took several inches of his cock into her mouth though she was unable to get past her gag reflex and take it into her throat.

“I'm about to cum, Jane.” Jason warned her. “Swallow all my cum as I pump it into your mouth.” He then grabbed the back of her head and pulled her close. He pushed his cock to the back of her mouth and erupted.

She coughed and sputtered a few times but succeeded in taking and swallowing every drop of Jason's cum. When he released her head, she sucked his shaft as she slowly pulled her mouth up and off Jason's cock. She then looked up into Jason's face and and smiled. She kissed the head of his cock and gave it a quick lick.

Jason helped Jane to her feet and hugged her. “Well, what did you think of that?”

“My God that thing is huge. I'm sorry I couldn't get you into my throat. I know you wanted me to do that. I promise I'll get better. Your cum tasted a little salty and was a bit slimy, but I can get used to it. I think I might even get to like it.” She continued to grin broadly.

Jason hugged her tightly and squeezed both of her butt's cheeks.

Jane giggled and asked, “What's next, Jason?”

“Jane, I think it's time you gave up your virginity. Are you ready to get fucked? Are you on the pill or some other form of birth control?” Jason asked.

“No! I've never done anything like that and have never had a boyfriend. So, there was no need to take that kind of precautions.”

“That's alright. Be sure to go to the Student Health Department right away. They will give you some birth control pills, or if you get knocked up before the pills become effective, they can give you the morning after pills.”

“Okay. I'll go there tomorrow.” Then her eyes seemed to light up with anticipation. “Can we still do it now? I really want to give myself to you.” Jane was anxious to get her cherry popped.

“If that's what you want, Jane. I'll be very happy to take your pussy's cherry. Come with me.”

Jason then took Jane's hand and led her to his bedroom. Once there he had her lay on her back. She raised and spread her knees without instructions from Jason. She was indeed ready and willing to give Jason her virginity.

Jason could easily see her tightly closed slit was glistening with her personal lubricant. Her sexual aroma wafted up to his nose. “Oh Jane, you look and smell good enough to eat.”

She giggled and replied, “I've been waiting to do this for years. It's just that my parents and preacher kept telling me it was wrong. I was also too afraid of the pain and the chance of getting pregnant to have sex. But now, for some reason, it just feels right to give myself to you.” She giggled again when Jason laid between her legs with his face near her virginal pussy. “You're going to eat me aren't you?”

“How does a 'good girl' like you know about things like eating pussy?” He asked.

“I've read almost everything I could find about sex. Though I have never done anything sexual, I've read all about it. Getting my pussy eaten always sounded so exciting.”

“Well, let's see if I can live up to what you've read.” He then kissed her freshly shaved pubic mound before giving her one long pussy-lip parting lick from her asshole to her clit.

Jane gasped and thrust her hips up to meet Jason's mouth. Her hands firmly fondled her ample tits and pinch her erect nipples.

Jason then proceeded to lick and suck her vaginal lips until she was writhing on his bed. He probed her pussy as deeply as he could with his tongue until she was approaching an orgasm. Jason then sucked her clit between his lips and rapidly flicked his tongue over it.

Jane cried out and exploded in orgasm. Her hands left her tits and grabbed the back of his head. She pulled his face tightly to her pussy as her orgasm rolled through her body. Jason's face was quickly coated with Jane's pussy juices. As her orgasm ebbed, Jane collapsed onto the bed and sighed. Grinning broadly, she said, “My God, Jason, that was fantastic. Please, let me catch my breath a minute. Then I will give you my virginity.”

“Okay, Baby.” Jason then kissed her pussy and crawled up the bed to lay beside Jane. As her breathing returned to normal, Jason gently petted Jane's pussy and fondled her tits. She kissed then licked his face clean of her own juices. “Is that what I taste like?” She asked.

“Yes it is, Jane. That's your pussy you taste on my face. Do you like it?”

“I think I do.” She then tentatively reached down and began stroking his cock. “My God! How big is that thing? It won't fit in me, will it?”

“It's only nine inches. I promise it will fit in you. You just need to be stretched a little. All virgins need to be stretched to accept their first cock.” Jason felt there was no sense in scaring her any more than the fear she already felt.

“Okay Jason, if you say so. I think I'm ready now.”

Jason could feel her pussy was soaking wet with her juices again. She hadn't even noticed when he pushed a second finger into her opening. She was as ready as she would ever be to give up her virginity.

Jason rolled onto her body and settled between her legs. He helped her raise and spread her knees to give him better access to her virgin hole. He had her reach down and place his cock's head at the opening to her inner treasures.

“Umph!” Jane grunted when Jason gave his cock a gentle shove. His cock's head spread her outer lips as it pressed forward. There was no pain. She felt only a filling sensation. “Umph!” With another push, his cock bumped up against Jane's hymen. With one final hard shove, Jason drove his cock deep and popped her cherry. He buried his cock into her depths and pressed against her cervix.

“Oh fuck! Damn that hurts!” Jane cried out. A single tear from each eye rolled down her cheeks. “Please Jason, don't move.” She begged.

“Okay Baby, we can relax a moment while you pussy gets used to being filled with cock.” He then kissed her lips tenderly and she responded in kind. Jason enjoyed the feeling of the muscles in Jane's devirginated pussy struggling to accept the cock that had invaded its midst.

After a few minutes, Jane gave a gentle upward thrust with her pelvis. Jason pulled his cock partially back before shoving it fully into her and again bumped into her cervix.

“Umph!” Jane grunted again and hugged Jason. “Go ahead Jason. I think you can move in me now.”

He began giving her slow but full strokes with his nine inch cock. “Umph, umph, umph umph.” She grunted with each deep thrust of the cock that had opened her pussy. He firmly bumped her cervix with each inward thrust.

Jane had indeed been ready to give her cherry. In a short time, she was taking all the cock that Jason could give her and returning each of his thrusts. Her orgasm hit first. She thrust her pelvis up off the bed and cried out. “Oh yes! Fuck me Jason! Give me that big cock! I want to feel your cock cum in me!”

Jason soon slammed his cock deep into Jane's cunt and pumped a large load of cum into her freshly devirginated pussy. He drenched her cervix with his cum while she moaned and groaned through her orgasm. “Oh my God Jason, that feels so wonderful. Fill me with your cum.”

He did just that. With his enhanced ability to produce cum, he filled her cunt to overflowing. When he pulled his cock from her, Jane had cum tinted pink from her cherry's blood flowing out of her pussy. It ran down the crack of her ass.

When she could breath normally again she cuddled close to Jason and cooed into his ear. “Oh Jason, I never knew it could feel so fantastic to give myself to a man. No wonder mom and dad and the preacher kept telling all of us girls how painful it would be to have sex. Yeah, it hurt, but the pain faded fast. It then felt so wonderful.” She hugged and kissed Jason passionately. When she broke the kiss, she smiled and asked, “What's next?”

Jason tenderly kissed her and replied. “Your ass, Baby. Are you ready to take it up your ass?”

“I think so. Will you be gentle when you put that big thing in my butt?” Jane smiled but Jason could see a bit of fear in her eyes as well.

“Of course I'll be gentle, Baby. I want you to be a happy little receptionist when you fuck. If I hurt you, you will always be a bit fearful of taking it in your ass, no matter who or how big your boss is. Now, roll over and get up on your knees.”

“Whatever you say Jason. I am a bit afraid of getting it in my butt, but I'll be a happy fuck for you and Dean Malcomb.”

As Jane rolled over and got up on her knees, Jason reached over to his night stand and retrieved his bottle of baby oil. He slowly applied the oil to Jane's asshole and surrounding area. He was soon easily sliding his middle finger fully into Jane's ass. She was moaning and pushing her butt back to accept the fingering. She didn't complain when Jason added a second and then a third well oiled finger to her asshole. He then applied the oil to is cock.

“You ready for this, Baby?”

She cooed and wiggled her ass in response.

Jason put his cock's head to the crinkled brown ring of Jane's asshole and gripped her hips. With a quick shove, he popped his cock's head past her sphincter and partially into her ass.

“Umph!” Jane grunted as the cock entered her ass.

“Are you alright, Jane?”

“Yeah, I'm okay. There was just a little pressure but no real pain when you pushed into me. Go ahead.”

With one slow but steady push, Jason fed Jane's asshole all but a couple of inches of his nine inch cock. He then tightened his grip on her hips and shoved the last of his cock into her backside.

Jane had taken Jason's full cock with little complaint. As his cock slid into her asshole, she lifted her head up off the bed and groaned louder and louder as she took more of his cock.

“Oh shit!” She cried out when Jason shoved the last two inches of cock into her asshole.

He kept his cock buried in her ass and patted her butt. “No Baby, that's not shit. That's cock up your ass. Are you alright?”

“I will be. I feel so full but it didn't hurt too much. Thank you for not just ramming that big thing up my butt.”

He again patted her butt. “Like I told you earlier, I want you to be a happy fuck. Hurting you will not result in a happy receptionist fuck.”

He then began sliding his cock in and out of Jane's asshole. She soon began returning his thrusts. As his orgasm built, so did hers. She pushed back to accept his cock each time he thrust forward. She soon began grunting as he buried his cock repeatedly in her ass. “Umph, umph, umph. Oh God Jason, I think I'm going to cum again. Can a girl cum while getting fucked in the ass?”

“Apparently so, Baby.” Just as he repeatedly drove his cock deep into her bowels preparing to dump his load of cum, Jane cried out. “I'm cuming! Fuck me! Fuck my ass, Jason.”

With one final ram, he planted his cock deep in Jane's bowels and filled her with cum.

She collapsed onto the bed in exhaustion. His cock remained buried in her asshole and continued to ooze cum into her guts.

When he pulled out of her ass, Jane rolled over and cuddled close to him. “Thank you for being so gentle with me. I will try to be the best receptionist fuck there is. Is there anything more we can do?”

Jane was indeed eager to be the best. “Well, to be the best, you will need to clean the cock that fucks you. Not with a wash rag, but use your mouth.”

Without a moments hesitation, Jane turned in the bed and took as much of Jason's cock into her mouth as she could. She licked and sucked all the debris of their evening of sex from the cock that had cum in her mouth, taken her pussy's cherry, and fucked her in her ass.

“Alright Jane, there's just one more thing I want to teach you this evening. I want to titty-fuck you. That's something you can do without removing all your clothes.”

“Cool, what do I have to do?” She asked.

Very little. Just lay on your back and let me show you how a titty-fuck goes.”

Jane did as Jason told her and laid on her back. Her C-cup tits stood firmly on her chest as twenty-year-old tits will do. He dribbled a little baby oil between her tits and laid his cock in the oil.

“Jane, push your tits together so I can slide my cock between them.”

She pushed her tits tightly together around his cock and asked, “Like this, Jason?”

“Yeah Baby. Now keep them like that. You can take my cock's head into your mouth when I push it forward if you'd like.”

Apparently, she liked. She eagerly bent her head forward and sucked on his cock's head each time it popped out from between her tits. She soon had Jason ready to cum again.

“Here it cums, Baby.”

“Oh yeah!” She enthusiastically moaned. Jane then released her tits and hugged Jason around his waste. She eagerly sucked his cock into her mouth. She sucked his cock's head like it was a straw in a thick malt until it began giving her the cum she was seeking. She again swallowed every drop of Jason's exceptionally large load of cum.

When she had all of Jason's cum drained from his balls, she kissed his cock and smiled up at him. “How was that?”

“That was fantastic, Baby. The neat part is you have nothing to clean up afterwards. Well, you may want to swipe a napkin between your tits. I have no doubt you will soon be the best damned receptionist any man could dream of having. That's all I can show you tonight. So, get dressed and go home. Just remember, don't walk into your boss' office when he has a visitor. You want to be his piece, not disturb his peace, or piece. Just make sure he knows you are available if he wants anything from you. You may want to start dressing a little sexier to get his attention.”

Jane smiled at Jason and replied, “Yes, Jason. I will, and I'll certainly be available to please him as he wishes. Thank you for a very informative and exciting evening. I hope to see you again very soon.”

“Oh, you will. I promise you will see a lot of me.”

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Whoa! Jason and the Dean Make a Deal X

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Comments (2)
Norton X — 18 January 2016 23:57
Oh, so very good!! Damn. Hot! And it's written properly too with spelling and grammar and everything! :) Thank you, Lucky Mann.
countrycadillac — 16 January 2016 20:16
This story just get's better and better. I hope the chapters never stop. Thank you !!!!!!
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