Illustrated by: Eduardo
The tie was for the meeting that afternoon and the underwear was for a weekend up in Door County with a guy he had recently met.
2. Doug wasn’t really into this new guy but he was lonely for some companionship and needed a long weekend away.
As a Chicago real estate mogul he worked and played hard but every guy had a limit.He caught a cab to Andrei’s and hopped out and went into the store.
3. Andrei’s catered to the best gentleman in Chicago but from the outside the place looked like a hole in the wall. Inside it was the best Italian and English fabrics with some silks and fine leather in between – kind of a Brooks Brothers on steroids.
4. A young guy in his late 20s was behind the counter but other than that the place was deserted.
Doug was greeted by the handsome young man.
“Yes sir, may I be of assistance?”
“Yeah, um, where’s Andrei?” said Doug sort of impatiently not expecting this young kid to be of any assistance whatsoever.
5. “Mr. Lantini is at his niece’s wedding in New Jersey for the weekend,” said the handsome young man smiling nervously at the powerful businessman.
Doug was not in any humor for a delay. Jared looked nervously at the man.
The guy was built like a linebacker and obviously had great taste in clothes.
6. But he was also the type that unnerved Jared and when Jared was nervous, he got a bit clumsy.
“I’ve got a meeting at Trump in about an hour and I need a tie to go with this cloth – the one I have on my client’s have seen before…I also need some undershorts.”
7. Doug removed the tie and tossed it on the counter loosening the top button on this shirt.
“In fact,” said Doug, I think I’ll need a fresh shirt for this meeting too,” he said unbuttoning the shirt and pulling it up out of his trousers
8. “Of course sir,” he said. “What type of shorts do you prefer sir?”
“Full cut boxers – what else is there – I like small conservative patterns on them nothing wild,” said Doug knowing that Lantini would not have had to ask that question as he knew by looking at a man’s bulge what type of underwear he was wearing.
“Sure sir, I understand,” said Jared feeling his dick tighten in his own shorts as the hunk described his underwear preference.
9. Jared went behind the counter and pulled out a couple of selections.
“You look like a 34 sir,” said Jared handing Doug the shorts.
Well at least the kid knows something, thought Doug to himself noticing the bulge in the young man’s trousers as came from behind the counter. Doug noticed for the first time how hot the kid really was.
10. As Jared handed Doug the underwear their hands did not quite meet and the shorts fell to the floor.
“Oh sir, my bad,” said Jared kneeling down to retrieve the packages that had landed on Doug’s shoes.
11. As he did, a pen that he had in the breast pocket of his shirt fell out and grazed Doug’s trousers leaving an obvious mark on it. Jared was horrified.
12. “Oh fuck!” said Doug aloud. “That’s great, just great you dumbass.”
Jared felt the blood rise into his face.
Mr. Lantini would not like this at all and Jared needed this job to help put himself through the final year of med school.
13. “Oh my God sir, I am so sorry. I think I can lift that out and press the pants,” he said reaching up for Doug’s trousers waist.
“What the hell are you doing,” said Doug his eyes arched and his voice cracking.
14. Jared was on overdrive now and was not even considering the disaster that was about to occur.
The only thing on his mind was making Doug happy and saving his job. His present course of action seemed logical to him.
15. “It will be just a minute sir,” said the young man feeling his erection grow in his pants as he fumbled with Doug’s waist, fly and clasp on the trousers.
As Jared feverishly worked on the handsome man’s trousers, he felt the heat of the man’s turgid penis through the fabric of the pants and undershorts.
16. “No, stop it, you can’t do this,” said Doug watching as the kid grasped the side of the expensive trousers and pulled them down exposing the man’s pressed underwear, his very hairy legs and his garters and socks.
“Oh my God! Oh my fucking God! You shit head!You just pulled my pants down right in the middle of the fucking shop! I’m in my fucking shorts. I’m in my fucking boxers!
What the fuck,” said Doug his face reddening with a look of horror.
17. He looked ridiculous standing there in his underwear with his pants down and his garters holding up his socks. His shorts were white with small blue triangles on them.
Jared’s jaw dropped as he realized that they were out in the main shop and not in the dressing area behind the curtain.
“Oh sir,” said Jared realizing what he had just done.
18. Jared hard on was clearly tenting his pants out as he looked in horror at the handsome man in his underwear.
Doug was frozen in horror…”this can’t be happening,” he thought to himself…”not to me, I’m an important guy in this town.”
Jared would be fired on the spot. Mr. Lantini had warned Jared about Doug by name saying he was very demanding but always spent a lot of money in the shop.
19. Now this powerbroker was stripped of his pants in the middle of the shop, pants that Jared had pulled down!
Doug was swearing and shuffling backwards, his ruined trousers getting twisted and dirty on the floor.
He moved away from Jared shielding the front of his underwear with his hands like something out of a comedy film.
20. This was not enough to hide the fact that Doug was getting seriously aroused by what was happening. The front of his conservative print boxers tented obscenely as he backed away. From the look of it, Doug packed a huge cock in his shorts, one that was in keeping with his huge ego. Jared moved forward.
21. “Here sir, put my pants on,” said Jared peeling down his trousers and revealing his bikini briefs.
“Pull up your pants you idiot, people will get the wrong idea if they walk in here,” said Doug backing away.
22. As he did so, his dick popped through the fly of his underwear and Jared’s shot up above the waistband of his bikinis.
23. Jared found himself removing his own shirt without explanation. He knew he had to take this hot businessman right there in the store regardless of the consequences. Guys like Doug turned him on and he needed to follow through.
24. “What the hell are you doing kid,” barked Doug his face red with embarrassment. He was standing there with his pants down in his underwear being seduced by a hot college kid. This could ruin his career.
25. “I think I’m…I think…I want to touch you sir,” He said reaching for the shop door and locking it and then pulling the shade down.
“What! I’m old enough to be your dad, you dumb twink,” said Doug his hard penis pounding along with the beat of his heart. He was always getting hit on by younger men but he had never gone this far with one.
26. The young salesman ran his hands on Doug’s white started athletic undershirt and looked him in the eye.
“My dad is not as hot as you,” whispered Jared.
“Oh Fuck,” said the aroused businessman as his seduction began.
Both men were standing there in their underwear, undershirts, socks and shoes with their pants down.
27. The only difference was Doug’s was wearing garters and was 20 years the young man’s senior.
The young man looked at Doug and then cupped his hand behind the older man’s neck and pulled him forward kissing his sexy lips.
28. This made a spot of precum form on Doug’s dickhead.
“Oh Fuck, you are really going to do this aren’t you,” said Doug, tipping his head back with closed eyes and a sigh.
“If you want me to,” said the hot young man.
29. “I think you are hot sir,” said the young man running his hand down the man’s undershirt and finally taking a hold of the man’s throbbing erection. “I wanted to rip your clothes off the minute I saw you. I knew I would love what I saw underneath and I think it’s hot that you are in my power in your shorts and garters.”
30. Doug moaned. He silently agreed. The kid had won and he was done putting up any form of protest.
“Just relax sir and let it happen,” whispered Jared.
Jared kneeled down and gently licked the head of Doug’s enormous dick. He rimmed around the head before coming fully down on the man.
31. He loved blowing a guy in his shorts and especially a handsome one like Doug.
Doug’s cock pounded wildly at the touch of Jared’s tongue and he felt his balls tighten with the familiar feeling of impending ejaculation.
32. Doug knew this kid had what it took to make him lose his load and wondered if he should tell the kid he was already close to cumming.
“I think I am going to blow man,” said Doug clenching his teeth.
33. Jared merely looked up and smiled as Doug threw back his head and said “fuck” before losing his seed in the young man’s mouth.
34. Jared has fumbled in his bikinis and pulled his hard cock out stroking it fervently before losing his load all over the man’s legs, garters and dress socks.
35. The two men paused, breathing hard and moaning as the last of the spurts of ejaculate flew out of their hardened cocks.
Jared came close to him and cupped his boxered ass.
Doug’s ass was tight as a dodge ball and Jared loved the feel of the man’s ass through the expensive underwear.
36. Doug turned to the younger man, pulled him close and kissed him deeply.
Jared kissed the handsome man back, smelling Doug’s expensive cologne mixed with his masculine scent and freshly ejaculated cum rising from the man’s shorts.
The two men embraced and kissed then shot their loads one more time while kissing and embracing one another.
37. Doug did buy new underwear that afternoon as well as a brand new suit.
And he did go to Wisconsin for the weekend, but it was Jared who went with him because it was that day that Doug learned who really was the boss.
End Of The Story
WHO'S THE BOSS
Written by: Christopher L.
Illustrated by: Eduardo