Desmond shares with Shaun
"Ok guys Rebecca and I will be back later" Lucy said grabbing her purse.
"Wait, where are the two of you going?" Shaun asked sounding distressed.
"We need supplies Shaun don't worry we'll be back" Rebecca said.
"Oh so I'm stuck babysitting Desmond again?" Shaun's comment was not answered, the girls just left and Shaun turned around to see Desmond sitting across the room staring at him with his arms folded across his chest, his eye brows draw together and an actual pout on his face.
"Why do you always say you're babysitting me?"
"Oh take a look at yourself right now, not only do you act like a child at times, but you actually look like one right now. Tell me Desmond, when the last was time, if ever, somebody put you across their knee and gave you a good spanking?" Shaun turned around to resume his work until Desmond's answer nearly caused him to fall off his stool, "about two months before the Templar's got me."
Shaun turned and looked at him in complete shock; he found it hard to believe that as a grown man he was spanked that recently. Desmond took the chair next to him and spun it around and then patted the seat indicating Shaun should sit next to him. He had a lot of work to do but the idea of hearing this story was just too intriguing to pass up so he went over and sat down next to Desmond.
"I was working at this restaurant/bar in the heart of the business district. Lunch time was our busy time because of all the executives coming in for lunch. The only nights that were busy were Friday and Saturday nights. Anyway I was working this one Wednesday afternoon, it was around five-thirty and I had one customer, his name was Jack. He looked to be in his mid to late forties, salt and pepper hair really a nice guy.
"Can I ask you a question Desmond?"
"Sure, what's on your mind?" Desmond said as he continued to wipe down the bar for something to do.
"Do you take compliments well?"
Desmond stopped and looked at the man thinking what an odd question.
"Um yea I guess so, I mean it's better than an insult right?" The man motioned for Desmond to come closer with his finger so Desmond walked over to him and when he did the man lifted himself up slightly off the barstool and leaned across to whisper in Desmond's ear.
"I have two compliments for you, one your hat and to you have an adorable ass" the man said and went back to sitting on his barstool. Desmond was used to girls telling him they thought he was hot but not another guy and it was the first time anybody ever complimented his ass so he just stared at the man in shock.
"Um well thank you, I have to say I've never heard those things from another man before but sorry I'm straight."
"I didn't say those things to try to seduce you Desmond I was just being honest, my name is Jack by the way" the man said putting out his hand so Desmond shook it so as not to be rude to a customer.
"I was here with some clients for lunch today and you were working then, shouldn't you be done by now?"
"I'm working a double, I need the money. Normally I would find a second bartending job but right now none of the places that pay well are hiring so I'm working as many extra hours as I can here to make as much money as possible." A waitress appeared at the other end of the bar and Desmond was never more grateful for the distraction, after filling the drink order he went to busy himself until Jack called him again.
"Would you like a refill?"
"No one's my limit" Jack said and Desmond watched as the man opened his wallet and saw a large amount of big bills in his wallet. He watched as Jack took five one hundred dollar bills out of his wallet, looked around to make sure nobody was around and then fanned them out.
"Do you see these? You can have them if you let me spank you."
"I said I'm not gay and consider the drink on the house but I really think you should leave now."
"No wait hear me out that is all I ask, please." Desmond doesn't know why but he stood there to actually hear what this man had to say.
"I'm not looking for anything sexual, no kissing, hand jobs, blow jobs or fucking. In fact you don't even have to remove one article of clothing; all I ask is for the opportunity to spank you. Don't say anything now just think about it" Jack said and he put a fifty dollar bill down with a card with a phone number on it and he left.
Desmond just stood there in shock, he had never been propositioned like that before and what was more shocking was that he realized he was slightly hard, like the idea of getting spanked turned him on and he was never into anything kinky. Without thinking he put the man's card in his shirt pocket and forgot about it.
It had been over a week since Jack was in the bar and after working another double with little money to show for it, Desmond noticed the card on his dresser. 'I can't believe I'm actually considering this' he thought to himself but he picked up the card and dialed the number.
"Jack Montgomery speaking" the man said when he answered the phone.
"Um hey this is Desmond, the bartender from last week."
"Oh hi Desmond, I really thought you would have tossed my card away. So does your calling mean you've considered my proposition?"
"Look I need you to understand that I'm not gay and I'm only doing this for the cash."
"I understand Desmond and trust me, if I was interested in having sex with you in any way, shape or form; you are worth way more than five hundred dollars." Once again Desmond was struck by what Jack said; it was creepy but kind of flattering as well.
"So what is involved with this exactly?"
"Just like I said a spanking Desmond, I want to spank you?"
"But why me, why do you want to spank me and pay me for it?"
"I like to spank hot guys with nice asses, especially straight ones."
"Do you get off on this?"
"I won't lie to you, I do get excited by it, but I already told you no sex is involved."
"I've never done anything like this before so what's involved exactly?"
"We meet up, you wearing the uniform you wear at work and I spank you and when I'm done you walk away with five hundred in cash and a slightly sore ass."
"You see that's what scares me, how sore, how are you going to do this?"
"Desmond haven't you ever been spanked before?"
"No not really."
"Ok this is how it will work, we meet somewhere, either your place or mine. I put you across my knee and I spank you with my hand, no brushes, paddles, or belts just my hand. Now keep in mind that the spanking doesn't end until I decide to end it but I'm not looking to brutally beat you within an inch of your life."
"I don't know about this."
"Yes you do, otherwise you wouldn't have called, admit it your intrigued by the idea otherwise you would have tossed my card in the trash after I left."
"I don't think I want you knowing where I live."
"Understandable, I'm still at the office and I'm alone you want to come here?"
"What you mean like now?"
"Sure unless you have plans and want to schedule a date a time?" Desmond was quiet for the longest time, he didn't have anything to do and he was rock hard, his dick throbbing every time Jack said the word spanking.
"I'm in the office building across the street from where you work, take the elevator up to the twenty first floor but if you're coming over now I need to know because there is a security guard downstairs and I need to tell him I have somebody coming over, oh and Desmond, I'll need your last name."
"It's Miles, my name is Desmond Miles and I'll be there in twenty minutes."
"Ok I'll see you then."
'What the fuck did I just do' Desmond thought to himself, why did he say that? Should he call back and cancel? Desmond hopped in a quick shower, why he didn't know and then he dressed like he was going to work.
"Can I help you?"
"Yes I'm Desmond Miles; I'm here to see Jack Montgomery?"
"Oh of course Mr. Miles just take those elevators up to the twenty first floor" the security guard said.
When the elevator doors opened up Jack was standing there waiting for him, he had a blue pinstriped suit on, just the jacket was missing, this tie was a little loose and his shirtsleeves partially rolled up. For a moment Desmond reconsidered the no sex thing because he actually was able to get a good look at Jack and realized he was built rather well.
"Hi Desmond" Jack said with a big smile and shook his hand and the first thing that entered Desmond's mind was if that was the hand that was going to be spanking him. Jack motioned for Desmond to follow him and so he did and he couldn't help but notice that Jack had a nice ass himself.
Desmond followed him down a long hallway, past empty offices; he listened and looked around for signs that somebody was around but it was deserted. They got to Jack's office, "are you nervous?" Jack asked he closed the door behind them.
"A little" Desmond said and the next thing he knew, Jack had taken him by the elbow, sat down in a chair and pulled him down across his lap.
"Hey, what about my money?"
"When I'm done" was all Jack said and his hand came down on Desmond's ass. It didn't hurt like he thought it would it startled him more than anything else. He doesn't know how long he was there or how many times Jack smacked his ass but the hits came at a steady pace, never faster or slower and never any harder. At first Desmond thought it wasn't too bad at all he could handle this, it would be the easiest five hundred bucks he ever made but by the time it was over he was hurting. Jack didn't need to spank him hard because after some time he started hurting.
"So let me get this straight Desmond you let some guy pay you five hundred dollars to spank you and you never had any kind of sexual interaction with him?"
"Nope he shook my hand when I arrived and shook again when I left."
"Were you really that desperate for five hundred bucks?"
"No not really but in total I ended up with twenty five hundred in my saving account."
"Wait what? You mean you did it again?"
"Yes I ended up over his knee a total of five times at five hundred bucks a pop?"
"What stopped you?"
"That's when the Templar's got me."
"If they hadn't would you still be seeing him?" Shaun asked.
"Probably, hey five hundred bucks is five hundred bucks."
Shaun just stared at him in disbelief, he knew there were things he didn't know or understand about Desmond but never in a million years did he ever think he would hear a story like that.
"And guess what Shaun?"
"What?"
"You get to do it for free" Desmond said as he laid himself across Shaun's lap because he knew Shaun had wanted to do this for a long time and Desmond, though he would never admit it, couldn't argue that sometimes he did things that warranted him getting spanked and since he noticed that Shaun was just as hard as he was why deny the guy this one simple pleasure.
When the first smack came down Desmond's eyes opened wide with shock, Shaun was in shape but he was nowhere near the shape Jack was in and that fist smack actually hurt. There was a few moments before the second one came down and soon Shaun had a rhythm going and soon Desmond was squirming and grunting He didn't start doing that until Jack was almost done and with Shaun it started much quicker and he had jeans on which offered more protection than the dress pants he wore as a bartender. He figured Shaun was going too hard to fast and soon his hand would start to hurt and this would soon be over, but Desmond was quickly finding out that Shaun, despite appearances, was freakishly strong and Desmond was on the receiving of the first real spanking of his life. When Shaun finally stopped and let him up he couldn't stop himself from rubbing his burning ass and he could feel the heat through his jeans.
"Let that be a lesson to you that if you start acting up again you'll know what to expect and the next time you won't have those jeans on" Shaun said as he got up and went back across the room to return to his work. Desmond's ass was hot and sore and he was rock hard and Desmond couldn't help but notice the substantial bulge in Shaun's pants as well.
"Want me to take care of that for you?"
Shaun knew exactly what Desmond meant and without turning around from his work he said, "don't worry you will later." Desmond couldn't help but smile because he was looking forward to "later" and he was looking forward to the next time they were alone so he could lay over Shaun's lap again.