Boss’s son takes over Written by The Wraith


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Alyson Webber sat nervously in front of her new boss, and could not believe after she worked 18 years for this company it could end like this. She looked at her new boss, and cringed at the way he now openly leered at her lush body. She was happy when Mr. Ryan said he was going to retire and Alyson thought this was her time to move up to vice president, but when she looked at her new boss, Mr. Ryan’s 18-year-old son, Daniel Ryan, and Alyson felt everything she worked so hard for all these years was about to fall apart. She remembered when Daniel interned last summer he made a lame pass at her, and an hour later tried to corner her in a storage closet, and when she rebuffed him and turned to the exit he grabbed her butt. Alyson slapped him and then told his father, and was so pleased Daniel was fired that same day, but here she was at Daniel’s mercy, and listened to him tell her “his” company was downsizing, and her job was to be eliminated.


Daniel remembered the day he was fired, and how he hated his father, but he never forgot his father’s reaction when he walked into his father’s study later that night and his father yelled at him for being such an idiot. “Boy, I thought I raised you better. I can’t for the life of me imagine you thought that was the way to get into Alyson’s panties, and that she’d fuck you in a closet. Hell boy, that’s an easy peach to peel, and had you come to me right off, you’d be fucking her tonight instead of your hand. Give me a couple months, and she’s yours body, mind, and spirit. There won’t be anything she wont do, and all you have to do is…”


Daniel looked over Mrs. Webber’s body, and he still lusted over this mother of 2. Daniel liked the way she always dressed in conservative business attire. Daniel looked directly at her tits, and rubbed his growing cock, and said, “So Alyson, tell me why you should keep your job.”


“Daniel. I’ve been…” Alyson was startled when Daniel yelled at her.


“Alyson, I’m your boss, and I think a person in your position should show a certain amount of respect. I expect to be called Mr. Ryan from now on.” Daniel said harshly, and he smiled at the way she shivered. He could tell she didn’t like the idea an 18-year-old boy she rejected now had the power to ruin her life.


“I’m sorry Mr. Ryan, as I was saying, I’ve worked hard here for the last 18 years and I feel I have helped this company…”


“Alyson, let’s face it, you’re getting old, and I’ve decided to hire a really cute collage grad that wears short skirts and tight tops, and train her to do your job at half the cost. Alyson, I’m looking for someone that would be so happy to have your job that she’d trade certain favors to keep it. This meeting is over, please go clean out your desk.” Daniel watched as Alyson struggled to not breakdown and cry, and he almost laughed at her emotional outburst.


“Oh God this can’t be happening. Please Mr. Ryan don’t fire me. Please… I don’t know what’s happening, but my life is falling apart a couple days ago my husband was unjustly fired for embezzlement, and now there’s a major problem with our checking account. I can’t lose my job now. I just can’t. Please you have to reconsider. I’m the only one working right now, and if I lose this job the bank will foreclose on my home, and I’ll lose everything. Please Mr. Ryan, I’m a good worker, and I need this job to pay for my husband’s lawyer…” Alyson stopped her ramblings when she saw Daniel look at his watch, and she got scared. She knew her time was quickly running out, and she needed to persuade Daniel to keep her on the payroll. Alyson grew desperate and said, “I can take a small pay cut if that helps to keep my job. Please Mr. Ryan don’t do this to my family. Uhm… I could buy a short skirt and wear it from time to time.” Alyson listened to herself, and could not believe she just agreed to wear a short skirt to keep her job, but she was without any other options.


“Alyson, Alyson, Alyson, I just explained what I expect from the person getting your position, and just wearing a short skirt is not going to cut it. Alyson, you’re a respectable wife and mother, and I doubt you’d want to dress sexy for someone half your age, and would you really want to come to my office every time I wanted sex? But that’s what it is going to take to keep your job. There, I can’t make it any clearer. What do you say Alyson, do you still want your job knowing you’ll have to put out and keep me happy?”


Alyson panicked when she realized her job at this company now hinged on keeping Daniel happy. She made a hard decision and shivered when she realized if Daniel asked her to go back into the storage room with him again, she would go and not utter one complaint to keep her job. She would do whatever it required to keep her family in their home, and her husband out of jail. She tried to look Daniel right in the eyes, but he was looking at her chest, and prayed he would reconsider letting her go and said, “Mr. Ryan, I’ll do what ever it takes to keep my job.” She expected Daniel to immediately accept her offer, and she got scared when he didn’t speak. She noticed he continued to stare at her breasts and blushed when she took a deep breath and pushed out her chest, and tried again, “Please you have to believe me…”


“I don’t know Alyson, you’re not a young woman anymore, and are you sure at your age you can keep me happy?” He loved how she blushed when ask her this question, and he was surprised her face took on a darker glow. This day turned out better than he expected, and knew the hook was set and it was time to real her in.

“Yes! I know I can… I’ll… I’ll do anything you want… Please… Just give me a chance. I’ll make you happy I swear I can. I have to keep this job.” Alyson could not believe after all those years of using only her brain to climb the corporate ladder she was quickly reduced to begging like a corporate bimbo, and felt sick that only her body could keep her job. For a split second she thought about filing a sexual harassment lawsuit, but with her husband in trouble and out of work she didn’t have the luxury of time. She sat there at Daniel’s mercy, and prayed he believed her because if he didn’t her family could be living on the street and her husband would probably be in jail.


Daniel waited, and sat quietly while he let the pressure build in Alyson. “Alyson sit up straight. That’s my girl. So Alyson, you want a chance to prove you can keep me happy? OK Alyson, open your mouth real wide, and form an O. Damn that’s nice. Now, move your head and show me how you’ll use that pretty mouth to give me a blowjob.” He sat at his desk, and watched a grown woman giving an air blowjob, he could tell Alyson was humiliated, and he said, “Alyson, you do know I’m going to use that pretty mouth each and every day from now on. I like bright slut red lipstick on my women, and this is the last time you’re to wear those muted shades. Do you understand?” He waited until she nodded and he continued, “Take off your jacket, and let’s see your tits. If you can prove you’re serious about pleasing me this afternoon I’ll let you keep your job.”


Alyson felt faint, but took a deep steadying breath. She never thought she would be asked to do anything so humiliating, and she felt her face flush as she sat in the chair, and moved her head forward and back. Alyson felt ill when she moved her tongue around her mouth, but she needed to be sure Daniel saw she put some effort into this humiliating display. Alyson knew she would be tested today, and feared tomorrow would be worse, but still leaned forward and took off her tan jacket. She placed it over his desk, and shivered at how her new boss openly lusted after her, and desperately wanted to run out of the room, but she sat there and ignored her boss’s looks that seemed to strip her naked. Alyson wanted to cry because she was about to lose the one thing she thought she would never compromise, but every time she moved her head or licked her lips she felt her dignity slipping away. Alyson leaned back in her chair, and sat up straight and fought not to cry.


“Mmmmm, that’s a nice set of tits you’ve got there Alyson. Why don’t you cup you tits. Oh yea, I like the way you do that. Now rub your tits and moan for me Alyson. No, louder. I want you to moan. Yea, that’s nice. Keep that up and show me how excited you are to keep your job. I’ll just sit here and watch you rub your tits. Don’t forget to moan for me Alyson, oh you sound like such a slut. I love it, and are you my slut Alyson? Are your nipples are hard yet? You’d better make sure I can see hard nipples or I might think you’re not enjoying yourself.” Daniel watched Alyson caress her tits, and grew more excited every time she moaned, and liked how she leaned her head back and pulled on her nipples and moaned like she enjoyed this. He leaned back in his chair, put his feet up on his desk, and just sat there for about five minutes and watched her. She looked so humiliated every time she moaned and it turned him on even more, and loved how she rubbed and caressed her tits, and then he put his feet back on the floor and leaned forward and said, “Stand up, and take off your shirt.”


Alyson felt deep shame as she openly caressed her breasts and pulled on her hard nipples, but every time she moaned she wanted to die, and knew this was only the beginning. She shivered when she thought she was just about to cheat on her husband with a boy that she didn’t even like, and when she once again pulled on her hard nipples and moaned like a slut she wanted to die. She dropped both hands into her lap, and almost fell when she stood up and had to hang onto the chair for support. She felt humiliated to be undressing in the boss’s office, and she prayed her colleagues never learned she debased herself to the boss’s son just to keep her job. Alyson’s fingers shook as she untucked her blouse from her skirt, and then unbuttoned her cuffs. She started to unbutton the top button of her blouse, but it took three tries before she unbuttoned it. She made the mistake and looked Daniel in the eyes, and never felt so ashamed of her actions in her entire life when she saw that he didn’t even try to hide how he rubbed himself under the desk. Alyson quickly looked at the carpet in shame as she unbuttoned the next button, and tried to remember she was doing this to save her family.


Daniel loved how Alyson’s fingers shook, and watched her fumble with each button before she could unbutton her blouse. He watched her carefully as the next button was undone, and he licked his lips when her blouse was fully unbuttoned, and he liked the glimpses of her tits hiding behind her plane white bra. He watched her place the shirt on his desk and stared at her tits, and said, “Take off your bra Alyson and show me your tits.”


Alyson struggled not to run out of the office, and had she had any guts she would have done just that, but she reached behind her back and unsnapped her bra. She took a second to build up her nerve, but as soon as she saw the hungry look in Daniel’s eyes she knew she had no other options left, and dropped her bra on top of her blouse. She stood there and trembled at how low she had sunk in her life, and prayed her children never found out how she sullied herself today. She listened to the rude comments about her hard nipples, “Damn Alyson with those long nipples you could put someone’s eye out.” and blocked out the remainder of Daniel’s crudeness when he made fun of the way her full breasts sagged. She shivered in shame and despair as she stood before an 18-year-old boy topless, and did nothing to cover her nakedness. She was thankful when he said, “Turn around, and lets see your ass.” She gladly turned her back to him, but could not forget the lust in his eyes, or how humiliated she was to be teased about her sagging breasts. She knew she was about to cheat on her husband as soon as she was naked, and prayed she could fake it so she sounded like she enjoyed it.


“You’ve got a nice ass for an old woman. Bend over and hike up your skirt up, and let’s take a closer look at that ass.” Daniel always loved the way her skirts clung to her big ass, and could hardly wait to sink his cock deep inside her. Daniel fought to remain calm, but he wanted to jump up from his desk and slam her down onto his desk, and fuck the shit out of her.


Alyson blushed bright red and was humiliated as she bent over and pulled up her skirt. She prayed he would not utter any more rude comments but knew deep inside that her butt sagged a little due to her age. She never thought she would be in a position like this, but here she was. She could not believe she stood in her boss’s office topless and every time she moved in the slightest to pull up her skirt she felt her large breasts jiggle, and could not stop thinking about how she was about to show her panties to her boss. She struggled with her tight skirt, but couldn’t get it around her full hips. She tried again and again, and was glad her back was to him so he could not see her deep humiliation.


“Alyson, it looks like your ass is just too big, so just take off your skirt, and while you’re at it take off everything. I never want to see you wearing panties under your pantyhose again. From now on you can only wear panties with garterbelts and stockings. You will either leave your panties or hose at home.” Daniel watched intently when she pushed her skirt down, and then pushed down her hose, and he grinned at the way she protected her panties from being lowered with the hose. He watched her struggle to keep her dignity as she lower her panties, and as soon as she bent over to retrieve her panties he said, “Not too bad Alyson. It’s a little big for my tastes, and droops some. I guess you should be very proud, especially at your age, to have ass that doesn’t make me want to throw up. Turn around slowly until I say stop. I want to see every part of you and make sure I still want to fuck you now that I see what you look like naked.” Daniel watched Alyson turn slowly in a circle, and he loved the way she was put together even though she was a little over 30 pounds overweight. There was something exciting about ordering a full-grown woman around, and when she faced him for the second time, he said, “Stop. Now pull your shoulders back, and lets see those tits again.” He watched as Alyson pulled her shoulder back and this motion accented her tits. He liked Alyson’s tits, and thought they were a bit too big with her extra weight, he figured she was a 36D, but if she lost some weight she’d be a perfect 36C “Bounce and shake your tits for me.” He almost laughed when he noticed her deep blue eyes looked like she was about to cry, but he loved the way her tits wobbled as she bounced up and down, and then started to sway side to side as she hopped. He kept her hopping for a few more minutes, “Damn those things really bounce around don’t they? That’s enough, you’d better stop before you give yourself a black eye.” He laughed at how long it took her breasts to settle, and as he looked her over he liked the way her tits still moved with her labored breath, and liked her relatively flat stomach and her full auburn bush. He wasn’t sure he would make her shave her snatch completely bald. He really thought she had a perfect ass made just for spanking, and he intended to try it out before the day ended. “Come here Alyson. Stand before me and let’s feel what you’re made of.”


Alyson was grateful to stop her humiliating bouncing, and as she walked slowly towards her boss she felt her breasts move with every footstep and cursed the way her large breasts swayed. She stood directly between her new boss’s legs and flinched when he touched her naked hips. She felt his hands moved around her back, and cupped her ass. She stood there quietly, but wanted to die and run out of the office when he jiggled her left ass cheek. She suffered her caresses, but almost ran when he slid his finger between her butt cheeks and touched her anus. She felt humiliated when he started to press his thumb into her ass, but sighed in relief when he stopped his intrusion and moved his fingers down between her legs and rubbed her vagina from behind. She shivered when she felt his hands move slowly around to the front of her body and closed her eyes when he ran his fingers through her pubic hair. She stood there and tried to forget this was not her husband touching her, and breathed a sigh of relief when he only fingered her a few times before he cupped both of her tits and started to knead them. She blushed bright red to be naked in his office while he explored her body in any manner he chose. She suffered his caresses in silence for well over ten minutes, but when he spoke she thought she might have a nervous breakdown.


“I like the way your tits feel in my hands, and I never want to feel your bra in the way, so today will be the last day you’ll ever wear a bra to work. I bet whenever you walk anywhere in the office your tits will flop around. I wonder what your coworkers will think about you not wearing a bra to work, and your frequent trips to the boss’s office. He ran his hand along the outside of her large thighs and said, “It looks like you need to workout more and lucky for you I know how to motivate people.” He rubbed her thighs inside and out for a few minutes and said, “Turn around, and lean over the desk.” Daniel reached into the side drawer, and pulled out some K-Y Jelly, and roughly spread it in her pussy, and wiped the excess on her ass.


Alyson felt sick when she felt the cold lubricant applied to her vagina, and it hurt when he roughly inserted two fingers, and worked them in and out three times. She spread her feet when she felt him kick her heels. She grunted, and bit her lips and tried not to scream in pain when she felt him enter her without any warning. Alyson felt sick when he leaned on her back and grunted in her ear while he fucked her hard and fast. She felt degraded, and tears came to her eyes that soon dropped to the desk, and wished this were just a horrible nightmare, and this would be the first and last time she’d be bent over this desk.


Daniel grabbed her shoulders, and speeded up his thrusts. He rammed his cock home, and fucked Alyson hard and fast. “You’ve got a nice cunt Alyson, but you’ve made a mistake. Had you been nice to me in the closet I’d still be in love with you, and would have treated you like a queen, but you made your choice.” Daniel pulled out, and had her turn over so her back was now on the desk. He stood at the edge of his desk and reached down and grabbed her feet and placed them on his shoulders, and then leaned forward fucked her in an agonizingly slow rhythm. He fucked her like that for a few dozen strokes, and then changed tactics again and now pulled out very slowly, and then slammed his cock home as hard as he could, and loved how Alyson grunted and moaned, and her big tits flopped around when he bottomed out. Daniel took her without warning or concern for her pleasure. He grunted with each and every thrust, and soon climbed onto the desk and with her almost bent in half he fucked her with everything he had and soon came deep inside her. Daniel climbed off her, and slapped her left tit, and said, “Get back to work Alyson! And leave you underwear.” Daniel fixed his clothing, and looked at Alyson as she collapsed on the floor and sobbed while she gathered her clothing,


Alyson felt degraded and used. She broke down and cried as she fixed her clothing. She felt numb, and knew nothing would ever erase this. She escaped to the women’s restroom and cried. She sat in a stall for over an hour before she made her way back to her desk. She knew she had made a mistake when she walked into her office and her phone was ringing. She answered the phone and almost started crying again when Daniel ordered her to get her fat ass back to his office right now because he was going to punish her for being away from her desk so long. She knew he just wanted to torment her some more, and prayed she could survive his lust until her husband resolved his legal troubles.


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