A Lesson From His Boss

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This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE

This fictional story is the artistic expression of the author who wrote it. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this story, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
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by clarf

Kate and Shawn had what they considered to be a perfect relationship. He was 30 and she was 26. They were good-looking, healthy and well-educated. Shawn had travelled the world building a successful and lucrative career, while Kate’s natural beauty and elegant dress sense made her the perfect executive’s partner. They had already decided they would get engaged in the near future and, after they wed, start a family.

Recently however, Kate had noticed that Shawn wasn’t himself. She’d seen him stressed before but this was different. He was eating less, wasn’t sleeping well and was going into the office ever earlier and staying ever later. Previously when she asked him about work he’d relate stories of the latest contract win or office gossip. Now when she tried to engage him when he came home, he simply mumbled that it was fine and immediately changed the subject. She decided that she had to get him to open up. She cooked him his favourite meal and when he was done laid it all out in the open.

“Baby something’s obviously wrong. You need to tell me what’s bothering you so I can help!”

“I’m sorry hon, I just don’t want to worry you. There’s nothing we can do about it so I just have to push through.”

“What is it Shawn? What has you so stressed out all the time?”

“It’s my new boss, Mr. Williams. He hates me, Kate. He’s always putting me down and making me do menial tasks. He criticises everything I do and laughs at me. It’s just really hard to take.”

“Well why don’t you call him out on it baby? None of your other bosses ever had a problem with you so just tell him to cut it out, it’s not acceptable.”

“I can’t honey. This guy has my career in his hands, I can’t risk pissing him off even more. He already says I’m incompetent.”

“Isn’t your end-of-financial year gala coming up soon? I can get to know his wife and you can get to know him socially and then he’ll see you’re a decent person and give you more leeway.”

“Yeah, it’s next Friday but he’s divorced. He’s slept with half the girls in the office and not just the single ones. One time he made me clean up the boardroom after he had sex with one of the secretaries on the table during lunch! It’s so demeaning and unprofessional.”

“That’s gross! Look, we can get to know him together and fix the problem. You shouldn’t dread going to work hon. I know we need the money but I’m sure together we can make it better.”

Shawn kissed his beautiful girlfriend and silently thanked God he had such a supportive partner.

The gala dinner was a black-tie affair and Shawn rented a tux. He wanted to treat Kate as a thank you for her support and so bought her a new little black dress. The hem was to the thigh and it plunged on both the back and the front. With her trim Asian figure and small, pert breasts, she pulled it off with an elegant sexiness few could match. The company always went all out with the end of financial year gala. They held it at only the best hotels and invited a celebrity speaker to give a motivational speech. This year’s guest was tennis player Rafael Nadal, one of Kate’s favourite sportsmen. They were both excited at the opportunity to meet him.

As they arrived at the ballroom of the 5 star hotel that was hosting the event they checked the seating chart to see where they would eat. Shawn sighed when he found their names.

“What is it baby?”

“We’re on the interns’ table, at the back of the room.”

“Why don’t you say something Shawn, you’re a Vice President! You shouldn’t sit down the back!”

“It’s no big deal, no point in causing an argument.”

The enjoyed the elaborate dinner and listened to the tennis star recount his insights on competitiveness and the similarity between sport and business. When he was done people began to mingle and Kate asked Shawn to point out his boss.

The man he indicated was standing at the centre of a circle of men and women listening to him speak. He was the tallest of the group at 6’5, and broad of shoulder and chest. Kate guessed he was in his late 40s or early 50s but spent a lot of time in the gym. With a full head of dark hair (greying a little at the sides) and an engaging smile he had an air of fatherly, powerful handsomeness about him. He was holding a cigar as he spoke and when he laughed, everyone listening to him laughed too.

“Come on Shawn, go and introduce me so we can start chatting to him!”

As they approached Williams did a double-take when saw Kate. He made direct eye-contact with her and smiled. Kate felt her mouth getting dry under his gaze. He moved towards the couple and the circle of hangers-on parted immediately. He strolled confidently towards her, took her hand firmly, raised it, and kissed it gently.

“Which one of my employees was lucky enough to bring you as a date tonight my dear?”

Shawn cleared his throat to speak, trying to sound less nervous than he actually was.

“Mr. Williams, this is…”

Before he could finish, Shawn’s boss turned to him angrily, still holding his girlfriend’s hand.

“O’NEILL! How many times to have to tell you – you address me as SIR! Don’t forget your place young man. And can’t you see I’m busy?”

Shawn froze to the spot while Williams turned back to Kate.

“Now my pretty, you were about to tell me who the luckiest man in the room is?”

Kate couldn’t help but smile at his compliments and the way he looked at her. His physical presence and charisma made her feel like she was the only girl in the room when he gave her his attention.

“I’m Shawn’s girlfriend, Kate. It’s nice to meet you Mr. Williams.”

“Ah Kate, I’ve complimented your photograph on Shawn’s desk many times. Please, call me Jim. We’re all friends at this company.”

Shawn reddened as he remembered the lewd comments Williams had made at Kate’s photo, how he said she looked like she wasn’t getting fucked properly and that she’d be much happier if she had a real man satisfying her.

“Where are you sat beautiful? I didn’t see you at dinner.”

Kate explained they were at the table at the back of the room. Jim leaned into her and whispered with a grin.

“I fear whoever placed you so far from my table may have just lost their chance of a bonus this year.”

She giggled. Jim pecked her cheek before saying he would find her again before finally releasing her hand.

“We’re about to give out the annual awards, I’ll come and find you afterwards.”

When he left Kate turned to Shawn.

“I think that went really well baby! He was so nice to me!”

“Yeah, he was…but I still made him angry.”

“Don’t worry Shawn, he said he’ll talk to us again later and then we can make sure you get to show him how nice you are.”

She kissed her boyfriend quickly on the lips and then led him back to their seats as the awards (distributed by the tennis star) got under way. The bulk of the awards were a standard corporate affair – best salesman, employee of the year (both won by Williams), best new employee and the like. Then there were semi-jokey personality awards. Williams picked up two; ‘most likely to be the last man standing in the pub’ and the ‘female choice award’. Nadal looked at the card that described the final award and laughed into his microphone.

“The last award is very special. Least likely to get a coffee order right!”

Shawn cringed visibly.

“And the winner is….Shawn O’Neill!”

The room erupted in laughter as Shawn made his way to the front of the room. Where the other awards had been accompanied by Oscars style trophies, Nadal produced an apron and laughed as he handed it to him. Shawn tried to act like he was joining in the laughter as he took it.

Williams shouted over to him.

“Put it on O’Neill! It will suit you!”

Reluctantly, he put the apron over his tux to howls of laughter from his colleagues and returned sheepishly to his table.

“What was that all about baby?” asked Kate when he returned.

“Oh, one of my new responsibilities is to get everyone’s mid-morning coffee. Mr. Williams says I always mix up who ordered what.”

“Haha, it’s good they see the funny side though!”

“Yeah, I guess you’re right.”

As Shawn lifted the apron over his head Williams reappeared.

“Kate, you divine creature! Tell me, are you a Nadal fan or a Federer girl?”

“Hi Jim! I’ve always been Nadal – I can’t stand Federer!”

“Fantastic. I’ve given my neighbour the boot so there’s a free seat with your name on it at the top table. How would you like to join us? I’d love to introduce you to Rafa.”

“I’d love to!”

She turned to her boyfriend.

“Come on baby, let’s pack up our things and move up.”

Jim placed a hand on her cheek and her stomach fluttered.

“I’m loath to disappoint a face as angelic as yours but no can do. There’s only one free seat.”

He maintained eye contact as he spoke.

“O’Neill! Be a good lad and stay here with Kate’s things while I introduce her.”

He placed her arm in his as he escorted her to the top table.

Kate had tremendous fun for the rest of the evening. She was nervous meeting Rafa but Jim made sure the conversation flowed by talking about his own sporting experiences as a competitive boxer, and telling funny stories about the practical jokes the guys in work play on each other. Shawn was the victim of more than one and Kate found herself crying with laughter. When it was time to go she spoke to Jim:

“I’ve had a wonderful time tonight Jim but it’s such a shame there wasn’t room for Shawn. You’ve probably seen he’s having a bad time in work at the moment and he was hoping he could get to know you a bit better. Maybe you could come over for dinner sometime so you boys can chat? I’d love to give a bachelor gent such as yourself a home cooked meal.”

“It would be my pleasure Kate! I’ve seen that Shawn is struggling. The business world is tough – there’s no room for wallflowers or crybabies and men have to be men. Maybe I can give Shawn a few pointers in that regard.”

“Thank you so much Jim, I’d really appreciate it and I know Shawn would do. I think if he could be a bit stronger like you he’d be fine.”

He kissed her cheek again as they bade goodnight and fixed a dinner date for the following week.

The interns had left long ago and Shawn had sat alone at the back table with their belongings watching his boss laugh with his girlfriend, taking any opportunity to touch her hair, face and back. She was beaming when she got back.

“Baby I had so much fun and was hanging out with Rafael Nadal! Can you believe it?”

He smiled at her excitement.

“And baby the best part is I think we can fix your work problem. Jim is coming over for dinner next week and he’s going to help you turn things around. Isn’t that great?”

Shawn was relieved that it looked like help was at hand. Once again his charming girlfriend had shown how supportive and caring she was.

The evening of the dinner Kate had prepared a delicious Chinese meal and wore her prettiest sun dress. Shawn was nervous again but Kate was looking forward to a fun evening chatting with Jim. When they heard the doorbell ring they went to the door together to greet him.

Shawn opened the door and extended his hand.

“Thank you for coming sir, it’s good to…”

Williams brushed past Shawn without taking his hand and walked to Kate, taking her by the waist as he bent low to kiss her cheek.

“Kate you’re a vision! And if the smell emanating from the kitchen is anything to go by my stomach is soon going to be as satisfied as my eyes are.”

She laughed and slapped his chest, surprised at how hard his muscles felt.

“O’Neill – why don’t you get us some drinks while we wait for dinner.”

Williams dominated the conversation as they ate, alternating between serious commentary on the affairs of the day and witty anecdotes. The young couple barely got a word in but had a fun evening listening to his stories.

When they were finished Shawn was more at ease and suggested they move into the sitting room. He finally worked up the courage to bring up the problem that had been plaguing him for months.

“Sir, I think Kate mentioned my difficulties to you. I’m so grateful to you for coming over. I just want to do better for you and the company and any help you can give me would be great.”

Kate nodded her agreement.

“We’re both grateful Jim. I wish I had a boss like you who took care of his employees.”

Williams sighed, and lit a cigar without asking permission.

“Frankly O’Neill, you need to man up.”

Shawn frowned.

“What do you mean Sir?”

He turned to Kate.

“I’m sorry for being coarse in your presence angel, but it’s important young O’Neill understands this point.”

“Oh it’s fine Jim. Be as direct as you need to be.”

“O’Neill, a manager’s job is to lead those underneath him. You understand that don’t you? It’s like I always say, the only people I need in my team are BSDs.”

Shawn reddened again. Kate interrupted.

“What’s a BSD?”

Jim turned to her.

“A BSD is an acronym we use to describe how leaders behave. It’s rather vulgar I’m afraid. It stands for ‘big swinging dick’. It means that real leaders carry themselves like they know they’re powerful, that they’re big and that they’re in charge. I’m sorry to say Shawn doesn’t do that and it shows. That weakness is what’s causing his problems at the moment. It’s nobody’s fault but his own.”

“That makes a lot of sense, don’t you think honey? You see how when Jim talks to your colleagues he’s so…manly?”

Shawn nodded and opened his mouth to speak but Williams interrupted.

“The thing is O’Neill, we all know you’re smart. You can run the numbers and show us how Excel works. But when we look at you we don’t really believe you’re in any position to tell us what to do. You come across as a geek, a data monkey if you will. To coin a phrase – and I’m sorry Kate – you seem like an SSD…a small shrivelled dick.”

Kate giggled nervously while Shawn tried to hide his embarrassment.

“Thanks for the advice sir, I’ll try to be more assertive” he stammered.

“Anytime. Now – on to more fun topics. Let me tell your sexy girlfriend about the time I took the top performers to Vegas for a weekend. It’s a little blue but I think you’ll enjoy the story. O’Neill, get me an ashtray for my cigar.”

“Oh…I’m sorry sir but neither of us smoke. Here, just flick it into my hand and I’ll drop it in the bin for you.”

“Good man.”

Williams deposited the ash in Shawn’s hand, who then made to move to the kitchen with the intention of retrieving a saucer to make do as an ashtray. Williams grabbed him by the wrist before he could.

“Don’t move boy! I almost got ash on your girlfriend’s beautiful rug! Keep your hand there until I’m done.”

He proceeded tell yet another tale of his exploits that had Kate rapt and soon they were both laughing. All the while Shawn held his hand in place to receive his boss’ cigar ash. When he was done, Shawn went to dispose of it and wash up, leaving Kate and Williams alone.

Jim checked his watch.

“My word, look at the time. Kate, I’m afraid I’ve had too much wine to drive home and I’ll never get a taxi. I think I’d better spend the night.”

“Of course Jim, you’re welcome in our home anytime. Let me make up the sofa bed.”

When she was done she leaned in to kiss Jim goodnight and felt his hand brush against her breast. It must have been an accident, she thought. He’s probably not well coordinated after the wine. It was probably the wine that was making her feel so frisky as well.

As she went into the bedroom she thought about asking Shawn to play with her clit before they slept. The idea of doing that with Jim right in the next room was quite exciting. Kate pulled a black see-through negligee on for bed. The only other item she was wearing was a pair of black, lace boy-cut underwear. Shawn loved the way that particular pair accentuated her tight, round ass and she was hoping it would get him in the mood so he’d want to rub her clit. Her boyfriend had already stripped naked with the intention of taking a shower.

“Thanks so much for getting Mr. Williams to help me Kate, I really appreciate it.”

“No problem baby, he’s a great guy. He’s such a good role model for you! He really is the kind of man you should aspire to be.”

As she finished her sentence the door to their bedroom was flung open. Mr. Williams strode in confidently.

“Kate, my beautiful, my advice to make Shawn more of a man wasn’t complete I’m afraid. The truth is that to be more masculine in work he has to be more of a man at home. It’s important that I show him how that’s done, and I’m quite confident that it will make you happier as his girlfriend too.”

Kate was too stunned at the sudden intrusion to react while Shawn instinctively covered his soft penis with his hands.

Jim took Kate’s hips in his large hands and pulled her to him. He kissed her, this time roughly on the lips, bowing his head to force his tongue into her mouth.

Kate was shocked, this invasion totally unexpected. She was too surprised to resist and by convention rested her hands on her boyfriend’s boss’ big shoulders.

Shawn saw what was happening and had finally had it. It was bad enough that Mr. Williams put him down constantly in work, had told his girlfriend how weak he was, and humiliated him in front of his colleagues. But kissing his Kate right in front of him was too much. He figured this was a test, to see if he could show that he could be a real man. There’s no way Mr. Williams could think this was ok. He stood as tall as he could and approached the embraced pair, placing a hand on his boss’ shoulder, which was about level with his eyes. He made his voice as deep as he could.

“Leave my girlfriend alone! I think you need to leave now.”

Williams broke his kiss from the breathless Kate and cupped her face in his hand. He smiled at her before turning to Shawn. He growled: “Do NOT interrupt me again, boy. I’ve warned you before and won’t anymore.”

He slapped Shawn with the back of his hand, his powerful arm smacking him backwards onto the floor, drawing blood from his mouth. There was no contest between the 6’5 former boxer and the small office worker.

“I’m going to show you how to treat your woman. You need to shut up, watch, and learn.”

He flipped Kate around, still standing, holding her back to his chest. As they both stood he shoved a hand down her panties.

“Something you need to learn O’Neill, is that women get turned on by how you act. Let’s see how young Kate has reacted to being around a real man for a change.”

He roughly pushed first two fingers, and then three into her pussy, making her cry out at the violation but still she didn’t resist. He put his thick fingers into her while pushing his palm back against her clit and without foreplay finger-fucked her forcefully. Kate’s knees weakened as the bigger man touched her. She was already wet and his attention to her cunt excited her even more. Just as she was getting used to his thick fingers inside her he withdrew his digits, and brought them to her mouth.

“You see Kate, you were already wet before I came in here. That’s what happens when a girl is around a Big Swinging Dick. They can’t help it. Taste how wet you are.”

She took his fingers in her mouth, amazed that he was right and her pussy was wetter than she could ever remember.

“Now, Shawn here needs to see how different things are when he acts like a man.”

He turned Kate back to face him and pushed her onto her knees. From his position seated on the floor Shawn (still covering his soft penis) knew what his boss was going to try next but was equally confident this would be the end of their ordeal. In the entire time they’d been together Kate had never got on her knees to give him oral sex. She considered it demeaning, and on the rare occasions she used her mouth on his 4 ½ inch (when fully erect) penis it had been only for a few seconds and mainly involved brief kisses and licks while they lay down.

Williams unzipped his fly and pulled his manhood out. Both Shawn and Kate gasped. His soft cock was already bigger than Shawn’s when hard. He grabbed the Asian girl by the hair as she knelt.

“Suck on that dick, beautiful. Show your boyfriend what you’ll do for a real man!”

Kate was turned on by how dominant her boyfriend’s boss was and, without thinking, took his penis in her hand and sucked on the head, her eyes looking to his for approval.

“Oh yeah baby, that feels so good. Shawn needs to learn. Show him what a cock sucking slut you can be!”

She felt him get hard and bigger than she knew was possible in her mouth as she sucked on him. He used the hand holding her hair to fuck her face, but his size meant he could get only half of his dick in her mouth no matter how hard he pushed. Suddenly, he pulled out.

“Here’s another lesson for you O’Neill.”

Williams lifted Kate easily to her feet and immediately pulled her panties to her ankles. He roughly took her negligee over her head then raised her up in his powerful arms by the thighs, spreading her legs apart.

“You see how wet your dear girlfriend is after sucking on me? Look at that O’Neill, she’s dripping!”

Shawn had been trying to look away but his boss’ command raised his eyes. Sure enough his sweet girlfriend’s juices were flowing down her thighs and it was clear from that and her breathing that she was incredibly turned on as Jim held her in the air in front of her boyfriend.

“She wants it O’Neill, do you see?”

“Yes sir, I can see.”

“Well O’Neill, I’m going to give it to her. It’s what she needs and you need to see how a man should treat a girl.”

Shawn knew now that his boss intended to fuck his beautiful girlfriend right in front of him, and that no matter what her mind thought her body wanted him to do it. This was too much. He gathered as much courage as he could and raised himself up, no longer covering his flaccid penis, no longer afraid.

“Sir, I’ve had enough. Put my girlfriend down and get out of my apartment.”

Williams was laughing as he lowered Kate to her feet. He strode up to his subordinate and pushed his soft chest, easily forcing him to the ground. He picked up Kate’s panties and shoved them in Shawn’s face.

“Smell your slut’s panties boy! See how fucking wet she is for me!”

Shawn could feel the dampness from the cloth against his face, understanding now that he had no choice in the matter. The man who dominated his office was going to dominate his bedroom, and it’s what the love of his life wanted. The thought made him cower and whimper a little.

Williams glanced down and noticed his small penis for the first time.

“Jesus O’Neill, you really are a shrivelled dick! And look at you there, curled up like a little bitch! If you’re going to act like a sissy you may as well look like one. Put these on!”

He threw the panties at Shawn’s feet. Shawn was afraid of being hit again and reluctantly pulled the lace knickers on.

Williams threw the discarded negligee at him.

“This too, wimp.”

Avoiding eye contact with anyone in the room, he pulled his girlfriend’s lingerie over his head.

“Now sit the fuck down and don’t say a word unless I speak to you.”

Williams walked back to Kate and pushed her onto the bed.

“Get on your hands and knees slut, I want to fuck you from behind.”

She never let Shawn make love to her in this position but somehow Jim’s deep voice made her excited to do what he wanted.

“This tight fucking pussy has never seen a real cock before. I’m gonna enjoy this!”

Wet as she was, it was still difficult for Kate to take a man of Jim’s size. He worked the head of his oversized dick between her cunt lips, then forced himself insider her.

“Jim, please be slow…it’s much bigger than I’m used to!”

He ignored the young girl and continued forcing himself in, stretching her pussy on his thick penis. He was about half-way in now.

“Tell Shawn how it feels whore. He needs to hear this.”

Kate moaned, then answered.

“Oh baby, even half his penis feels so much bigger than yours! It hurts but it feels amazing at the same time. I can’t describe it!”

With that Williams withdrew and flipped Kate back over. He lifted her legs over his shoulder as he stood at the edge of the bed and thrust his enormous cock into her wet slit in one go. Kate cried out as he hit her cervix.

He immediately and remorselessly pounded into her.

“I love fucking virgins, and you may as well be from what this pathetic boy has been giving you!”

He huge balls slapped against her ass as he drilled her over and over.

Kate had never felt anything like it, her vagina filled completely and every nerve tingling as the tall, strong man took what he wanted.

“Oh my god! Oh jesus it feels so good!”

He held her by the tits as he fucked into her.

“Tell Shawn what’s happening. Look at him!”

She turned her head to her boyfriend, her tits bouncing obscenely as his boss hammered her pussy. She saw him still sitting against the wall, dressed in women’s lingerie.

“Honey I….oh!…I’m going to orgasm. I’m going to cum on a man’s cock for the first time! Jim is…oh my god!…Jim is such a good teacher for you!”

She couldn’t continue, her eyes closed tightly as she felt the orgasm building. Her only previous orgasms had been from vibrators, and this felt so different. Everything about the situation and the incredible man fucking her made her senses heightened. An explosion of pleasure radiated from her vagina throughout her body.

“Ahhhhh…oh my god…YES!”

Both her pussy and the rest of her body convulsed as her orgasm subsided. Jim stopped his pounding but kept his big dick inside her.

“Thank you so much Jim, that was incredible! I can barely breathe!”

He smiled but didn’t say anything. Pushing her more fully onto the bed, he climbed on top of her in the missionary position.

“Shawn needs to learn, so this time I want you to tell him everything as we go.”

“Ok Jim. I want to help him.”

He started his pounding again, one hand grabbing her by the ass, the other mauling her tits.

“I can feel his big cock inside me baby. It’s still stretching me.”

Heavy breathing.

“He’s touching places I’ve never felt before. It feels so good!”

Moaning now.

“He’s pushing against my cervix, I can feel him up in my womb. It’s so deep!”


“Oh god baby, I’m gonna cum again. It just feels so big!”

Jim was thrusting as fast as he could into her, clearly close too. His pace reached a peak and he roared as the first jet of his load erupted inside her. It was the first time any man had cum inside her pussy.

“Oh fuck baby! I can feel him shooting inside me! I…ahhh!…I can feel each of his spurts hit me…I’m gonna cum….ohhhhh!”

The two lovers came together, Kate’s hands clawing at Jim’s muscular back as their orgasms overtook them.

Jim withdrew his penis and rolled onto his back in the spot that Shawn usually slept.

“Fucking hell Kate, you’re an amazing woman. That was superb.”

Kate was still catching her breath, stunned at what she had just experienced.

“You’re an amazing man Jim! Thank you so much for this, I’ve never felt anything like it.”

Jim reached for another cigar, lit it, and rested Kate’s head on his broad chest.

Shawn was terrified that Kate would get pregnant from the powerful man’s semen currently deep inside his girlfriend. He sheepishly spoke to her.

“Kate honey, don’t you think you should wash up? You know, down there?”

“Baby I can’t move…it feels sore and wonderful at the same time but I need to just lay here for a while.”

Shawn knew he was defeated but also knew what he was about to do was necessary. He climbed onto the bed and went between his recently fucked girlfriend’s legs. He extended his tongue and started lapping at the sperm dripping from her pussy.

“Mmm baby, that feels nice!”

He stuck tongue in, trying to get at the spunk inside her vagina. He could taste both her wetness and his boss’ saltiness at the same time.

“Oh honey, don’t stop. That’s really good!”

Kate felt his tongue on her clit and in her pussy, as she and Jim looked down on her boyfriend still wearing women’s lingerie.

Williams spoke.

“O’Neill! Don’t make me ash on the bed. Put your hand out while you clean your girlfriend.”

Lacking any option, Shawn extended his hand to be used as an ashtray while he sucked his boss’ cum from his girlfriend’s pussy.

She started to moan again.

“Oh baby, faster…right there…that feels good!”

Williams used his free hand to reach over and push Shawn’s face onto Kate’s snatch.

“Oh god YES! There baby…YES, YES!”

The third orgasm of the night overtook Kate as she lay on Jim’s chest getting her clit licked while he held her boyfriend down.

As she recovered, Jim stroked her cheek.

“O’Neill, it’s late. Time for us to get some sleep so give us some privacy.”

Shawn left the room and took his place on the sofa bed. As he drifted off to sleep he thought about how he could learn from the lessons Mr. Williams was giving him.

The next morning, Shawn was woken by his boss shouting from his bedroom.

“O’Neill! Get in here boy!”

He quickly went into the bedroom, still wearing his girlfriend’s panties and negligee. Kate was still dozing on Williams’ chest, his muscular arm enveloping her.

“I gave Kate quite a seeing to last night O’Neill, she’ll be as hungry as I am when she wakes up. Go and make us some breakfast.”

“Yes, you’re right sir. She’s not used to being handled that roughly.”

Shawn went to the kitchen to prepare their food. He cooked the lovers some eggs and poured them juice. When he returned to the bedroom, what he saw almost made him drop the tray.

Both Williams and Kate were awake now, and both were completely naked. Williams was standing on the bed, with Kate kneeling in front of him. He was holding her wrists together with one of his big hands over her head, and she was sucking hungrily on the big cock that had given her such pleasure the previous night.

“Put those things down O’Neill. Come over here and give your cocksucking slut of a girlfriend a kiss good morning.”

Shawn bent down to kiss Kate but Williams didn’t stop fucking her hot mouth. He kissed her cheek, and could feel his boss’ big tool press against it as he thrust into her throat.

“Get down there and eat her pussy while she sucks me O’Neill!”

He positioned himself between her legs as she knelt on the bed. Her cunt was still gaping from the night before, and her hot dampness was clearly visible. He lapped hungrily at her vagina, and sucked and nibbled on her clit.


Kate moaned around the big dick in her mouth.

He continued licking her clit and the Asian girl spread her legs wider to lower herself onto her boyfriend’s face. Williams picked up the pace, trying to force as much of his penis into her willing mouth as he could.

Shawn couldn’t help himself. Seeing Kate enjoy his tongue on her clit turned him on, and his modest erection made a tent in the lace panties he was wearing. Williams noticed the pathetic bulge and laughed. He released Kate’s wrists and withdrew from her mouth.

“Oh you like that, do you O’Neill? Well get up here for a closer look!”

He leaned over and grabbed Shawn by the hair from under Kate, dragging his subordinate to his knees directly in front of him. He pushed Kate’s face back to his crotch.

“Suck on my balls, you hot little whore. It’s time for your sissy boyfriend’s next lesson.”

Kate licked his scrotum before taking each large ball into her mouth, one at a time. Her pussy was still tingling and she found herself hoping that this lesson might end with Jim taking her again.

William’s fist stroked his cock and Kate felt his balls tighten in her mouth. He still held Shawn in front of him by the hair and pointed his penis directly at him. Despite realising what he was going to do, Kate was nevertheless shocked to see rope after rope of thick, white cum spurt from Jim’s penis and coat her boyfriend’s face. Jim grunted as he came.

“Nnnnghhh…let’s see how you like that boy!”

When the last of his cum had been deposited on the smaller man Kate took his penis and loving sucked the end. Jim stroked her head and spoke.

“Look Kate, his needle dick has shrivelled again!”

Kate turned to look at Shawn. Sure enough the front of the panties were almost flat, with only the smallest of bulges visible. She couldn’t help but wonder if dominance came so easily to Jim because of his much larger penis, and whether that made it more natural for the couple to bring a man like him in to satisfy her sexually rather than try to change Shawn. As much as she loved him, and as sensitive and caring as he is, could a guy with a small penis ever really provide that excitement and masculinity in the bedroom? He’s so supportive, she was sure he’d understand. And if Jim was the person to provide it, he could continue helping Shawn with work. It really could work out for everyone.

“I think your girlfriend needs another seeing to. Why don’t you see what you’ve learned and give it to her.”

“Thank you sir, I’d really like the chance to prove myself.”

Shawn pulled his panties to the side and released his penis. He stroked himself to his full 5 ½ inches and then climbed on top of Kate. He slipped into her easily and then leaned down to kiss her but she turned her head to the side.

“Baby you still have Jim’s cum on your face. He came so much! I don’t want to get in my hair.”

“Sure honey, I understand.”

He slowly moved his penis in and out, wanting to show how making love could be just as much a turn on for her as the big-dick fucking she got last night.

“I love you so much Kate.”

“I love you too Shawn…that feels…nice.”

It was true, the familiar feeling of her boyfriend’s small penis slowly moving in and out of her, and his soft torso on top of hers was…pleasant…and reassuring. But she knew now this wasn’t sex. There was none of the hot lust and intensity that Jim had showed her.

Shawn increased his pace, his panty covered ass moving up and down faster now while Kate looked at the ceiling. Williams had had enough of this pathetic display.


He lifted Shawn by the shoulders and threw him off Kate.

“For fuck’s sake Shawn, you can’t take a woman like that! What kind of man are you?”

He cupped Kate’s pussy in his shovel-like hand.

“Kate, beautiful. Do you think he needs another lesson?”

“I think that would be great, Jim! But I’m still pretty sore down there from last night. It was ok with Shawn but I’m not sure I can handle you right now. Your penis is just so much bigger than I’m used to.”

“That happens quite often. It’s not a problem – I’d love to take your sweet ass in any case.”

Kate’s eyes widened. She was an anal virgin. Shawn had begged her to let him have her ass many times but she’d never acquiesced. Could she really give her anal virginity to his boss? It was still scary but he was so dominant she didn’t want to say no. And he was so confident in what he was doing, he must know how to handle her. She would give in to him, and she was nervous and excited to finally try anal.

“Get her ready fag, and plenty of saliva. I don’t want to hurt her.”

Williams lifted Kate’s legs up at a 90 degree angle and pushed Shawn’s face to her ass. He licked and probed for all he was worth, using a mixture of his own spit, Kate’s wetness and William’s semen to prepare her ass for it’s very first cock. In short-order she was well-lubricated.

“I think she’s ready for you sir.”

Williams pushed Shawn off the bed. He placed Kate’s legs on his shoulder and pressed his cock at her tight hole. With difficulty, the first half-inch disappeared inside and Kate felt a man in her ass for the first time.

“Oh god, it’s too big Jim! I don’t think I can take it!”

“Just relax, my beautiful. It will hurt at first but I promise you’ll like it. When I’m done your ass will be as slutty as your tight little pussy.”

He painfully forced inch after inch of his monster inside the slight Asian girl. At last, the entire thing had disappeared into her. Kate had never felt so filled, and the intense pressure erased the pain of her anal deflowering, replacing it with pleasure.

“Oh that’s amazing! Thank you Jim!”

“I’m going to fuck your ass now Kate. Do you want it?”

“I do! Please fuck my ass!”

He started pistoning in and out of her, using a hand to manipulate her clit and slap her pussy as he did so.

“You want me to take your anal virginity while your boyfriend watches, wearing your panties and with my cum on his face?”

“Yes! I don’t care…I just want you to fuck me…mmm…oh god yes!”

He increase his tempo and he could see she was nearing her first anal orgasm.

“Would you have let Shawn put his limp little worm in your ass?”

“Nnng….no…I need a big dominant cock…oh fuck…I need a big dominant man!”

“Who owns your ass baby?”

“Arrrghhh….you do Jim! You own my ass!”

She was screaming in between his questions, his dirty talk and fucking driving her wild.

“Tell your boyfriend what you think of his cock!”

“Mmmm….oh god….I think it’s a….oh fuck yes…it’s a small…shrivelled…DICK!”

She came as she finished the sentence, her body bucking and feet straightening with toes curled. Her back arched and she screamed. Williams pounded her ass for all he was worth and her orgasm dragged out. It lasted a full two minutes under his relentless assault before finally he too reached the threshold.


Kate looked in his eyes as he filled her ass with his cum, just as he had earlier claimed her pussy and marked his dominance over her boyfriend. His large frame collapsed on top of her as they both panted from the exertion of their powerful orgasms.

“Thank you so much Jim, it was better than I ever could have imagined.”

“You’re welcome Kate. I’ve been with a lot of women but I’ve never met one who’s been so neglected in the bedroom who’s so responsive, so sexual. I’d very much like to keep visiting you…and keep helping Shawn of course.”

“I’d love that Jim!”

She beamed and turned to look at Shawn.

“We both would, isn’t that right baby?”

“Umm…yes, thank you sir.”

She wrapped her arms tighter around Jim’s broad back.

“God, I don’t know about you guys but I’m SO hungry!”

“O’Neill, the breakfasts are cold. Go and make some fresh ones.”

Shawn slipped back to the kitchen and started cooking. Kate seemed so happy and he was glad. He admired Jim for how he knew what Kate wanted without having to have it explained to him. As he cracked some eggs into a pan, he wondered what the future would hold with this remarkable man in their lives.

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