Proposition

James got up from his place at the quaint café down the street from his apartment. Shrugging into his jacket, he waved to the young guy behind the counter and left his half full coffee cup on the table. The air outside the small café was chill but not unpleasant and James sucked in a deep breath that felt sharp entering his lungs.

He hadn't been out without Gloria for a while but he had needed some time to think. She had finally brought up the big M word. James definitely loved Gloria and wanted to get married but with him studying and her only working part time, was now really the time for it?

It had ended in a cold night of excessive politeness and not really talking to each other which had made James feel terrible. The real problem was of course the massive debts he had racked up and hadn't quite found the right time to tell her about. He knew that he should have told her a couple of years ago about his financial situation, but it seemed to be so much easier to go on living off credit cards and pretend that he didn't have a big black mark against his name on every lending establishment within 100 miles.

It wasn't until James had almost walked into the man that he noticed someone standing in front of him.

"I'm sorry" Said the man once James had stopped and looked up at who was blocking his path.

The guy was about 5'5, middle aged and a bit podgy all over. He wore an old fashioned suit and looked well off although a bit fashionably challenged.

He had a strange European accent, like Dutch or German or something.

"I couldn't help but notice you inside the café. You are most thoughtful looking." Said the man in his slightly clipped but musical accent.

"Ah yeah." Said James, not really sure what the guy meant.

"I am once again sorry. The reason that I noticed you, was not in fact for your thoughtful looks, but I am very interested in seeing you." The man said.

James wasn't sure if he was losing something in translation but it didn't sound as though this guy was making any sense.

"I don't really get what you mean." James said, trying his best to hold on to his patience.

"I would like to see you." Said the man, unhelpfully. "I would pay you much, to see you."

"You're seeing me now." Said James. He was definitely getting a bit irritated by this odd guy. But if he was honest the comment about paying you much had caught his attention.

"Ah yes. What I was meaning, was seeing more of you." The man gave him a slightly embarrassed smile.

"What I mean to say is, I think you have a very nice body and I would like to see you without your clothes on."

The man smiled warmly at him as though he had just commented on his sports shoes or something.

"Whoa, hold up buddy." James stepped back and held up his hands.

"I don't know how you got the wrong idea, but I'm not gay or anything." He said defensively.

The man also raised his hand in a placating gesture

"There would not be any need for touching." He said, reassuringly.

"I would just like to look at your body. I would pay you one thousand of your dollars." He finished

James lowered his hands. As creepy as this whole situation was. A thousand bucks for just looking at him naked was nothing to be scoffed at. He would need a lot more information before he could agree to anything like that though.

"So you would want me to take my clothes off here?" James looked around as though someone might be spying on them right now waiting for him to show off some flesh.

The man smiled again, his plump face taking on an eager shine.

"No. No. I have an apartment just a block away. You would come with me, I pay you your money and then you take your clothes off so I may look at you." He smiled again but it was coming across even creepier now.

"How long do you want to look at me for?" Asked James, feeling a bit defensive or insecure already, even with his clothes on in the middle of a public street.

"For just one minute." Said the man, holding up his pudgy index finger."

"You stand, then turn around for me to look and then you can put your clothes on and go with your thousand dollars."

James was wavering. This seemed like a simple thousand dollars, but there was something about this little man that he didn't like. Quite possibly the fact that he was propositioning men in the street to put on a private strip show for him.

"Here" Said the man pulling something out of his jacket pocket. "I give you half now and then the other half when we get to my apartment."

The man opened a leather wallet that was absolutely stuffed with one hundred dollar bills. He pulled five out of the wad and handed them to James.

The look and feel of the bills in his hand made him feel good. He rubbed his fingers over the crisp bank notes. A thousand dollars wouldn't be nearly enough to clear his debts, but it would definitely be a start. All he had to do was strip off, stand for a minute while a creepy pervert checked him out and then he could get out of there a thousand dollars richer.

"Okay." Said James, feeling a bit dirty.

The apartment was only just over a block away, back past the Café. The man led him into the building up two flights of stairs and opened his door. It was an ordinary town apartment, tidy and almost bare. The windows in the living room looked out over a busy street and into a small green reserve.

The man gestured for James to go into the bedroom and he followed quietly behind him then walked over to the bedside table and placed the extra five hundred dollars down where James could clearly see it.

"Please take off your clothes." Said the man. His clipped accent making it half a question and half a demand.

The whole situation flashed through James head again but at the end of it all he could really focus on was the money. This would be over in a few minutes and he would be out of here a crisp grand richer.

He unbuttoned his shirt and took it off, revealing his long slim athletic body. Next he kicked off his shoes, then undid the button on his trousers and slid them down his legs before stepping out of them and throwing them onto the bed beside his shirt.

The man stepped forward a bit now to see more closely and James saw a hungry look in the man's eyes. If this weird little man tried to touch him he would kick his ass. The man gently picked up James' clothes and placed them almost reverently beside the five hundred dollars he had put down.

The man turned quickly back and gave James a nod to indicate that he should take off his boxer shorts.

James did. He slipped them quickly down his legs and kicked them off. The man grabbed them and added them to the clothes pile, as though he couldn't handle the scruffiness of the clothes being on the ground for a second.

"Your socks too please." Said the man and James obliged by taking off his black socks and tossing them to the man.

Now James stood completely naked in front of the man. He was a tall athletic guy with good muscles and not much fat on him. He was pretty proud of his body if he was going to be honest. He went for the natural look, no porn star shaving or even trimming for him. He loved that his dick was big when flaccid. It hung between his legs about 6.5 inches before it got hard and easily 9 when he was properly turned on. Not that there was any risk of that happening with this creepy man looking him up and down as though he wanted to eat him.

The man came a lot closer and looked closely at his dick before looking up at him.

"You truly are beautiful. It is a shame that you are so hairy." The man said.

"Turn around now please and bend over slightly." He kept his head close to James' waist as he rotated on the spot and bent down a tiny bit.

"Bend over more." The man said. James noted the lack of please, but he complied.

"Put your hands back and spread for me please." The man was back to using please, but that seemed a bit of a stretch past his initial stand here while I look at you deal.

"Are you keeping time?" James asked back over his shoulder while he bent over, not yet spreading his ass open as the man had asked.

"Once you spread yourself open for me to have a look at, it will be time up." Said the man.

James put his hands back onto his butt and parted his ass cheeks. He felt dirty and used standing there bent over while a man looked at his asshole from less than a foot away, but he just wanted to get his grand and go.

The man suddenly stood up and stepped back.

"Thank you." He said happily. Our agreement is concluded, you can take your money and leave now if you wish.

James stood up straight and let go of his butt cheeks quickly. "What the hell does he mean "if I wish?" Of course I wish" he thought.

"If however" The man continued "You wish to earn more money. I would like to see you again without your pubic hair."

James thought about it quickly but decided that once he left this apartment there wasn't much chance of him coming back even for another thousand dollars.

He started moving towards the man and the bedside table that had his clothes and money on it.

"I have everything you need in the ensuite shower." He said pointing to the open door at the back of the room. "I will pay you another thousand dollars to shave off all of your pubic hair while I watch and then let me look at you again like you just did."

The man spoke quickly, as if getting the words out before James could reach his clothes would make it seem more appealing.

James did stop then to think about it. It wasn't as though he would be showing the man anything he hadn't already seen. If one of his mates had bet him a hundred bucks to shave off his pubes he would have done it in a second, and this guy was going to pay him a thousand.

Two thousand dollars would put a much bigger dent in his debts than just one thousand. Shit. He couldn't believe he was actually considering this, more than considering it. He had stopped dead.

"Give me the money." Said James. Accepting that he was about to shave himself so a perverted middle age guy could get a proper look at his asshole.

The little man grinned widely. He took another thousand dollars out of his wallet and adding it to the $500 from the bedside he stuffed it all into James' jacket.

"Right this way!" The man exclaimed excitedly, gesturing towards the ensuite bathroom.

James walked cautiously into the small bathroom and saw that the shower was already set up with shaving foam and a brand new razor ready to go. The little man slipped past him and turned the shower on for him then waved his hand excitedly to get James in.

The next few minutes were some of the most degrading in James' life so far. He stepped into the shower and let the warm water cascade over his body before lathering up his crotch and butt with the shaving foam. He systematically shaved everything off from his upper thighs to his belly button with the little man giving him directions and suggestions throughout.

He finally finished scraping the razor around his asshole and looked up to find the little man staring at him dreamily. The man had undone his pants and had let them fall open to his thighs and he was now stroking his cock.

"Hey!" James almost shouted in outrage. "You never said anything about jerking off while you watched me!"

The man smiled widely at him. "I just couldn't help myself! Come over here so I can get a better look at you." He said, his voice getting huskier with every word.

"Put that away first!" Said James. He grabbed a towel from beside the shower and quickly started to dry himself. The man smirked at James and then walked through into the bedroom.

James followed quickly, only because that was where his money was and he didn't want to leave the little man alone with his clothes and cash for an instant longer than he had to,

When James walked into the room, the man stood beside the bed with his pants around his ankles still stroking his dick.

"Drop the towel." Said the man. Staring at James.

James dropped the towel away from himself to give the man what he had paid for, an unobstructed view of his naked body, freshly shaved.

"I have been very happy with what I have purchased so far." Said the little man

"But now I think it is time for you to make some real money. Yes?" The man asked, lifting one of his eyebrows.

James wasn't entirely sure where this was going but he thought he had a pretty good idea and he was having none of it. Before he could speak though, the little man continued.

"I want to pleasure you with my mouth. No. I need to do it." The man said, his stare intense.

"I will pay you three thousands, to let me pleasure you." The man said seemingly uncontrollable in his lust. His hand still stroking over his dick was very distracting

James' initial thought was to grab his clothes and run. He knew this creepy gremlin man was dodgy as hell and he could of guessed he would want someone to suck on something at some point.

But, an extra three grand just to get a blowjob was probably better pay than any hooker had ever been offered. James didn't grab his clothes and run, he just stood there looking back at the little European man who was still pumping his cock. There was something desperate about the little man and it both scared and excited James a bit. He suddenly felt powerful at causing this man to have such strong desire and he decided then that he was going to do it.

"Five thousand." Said James meeting the gaze of the little man and then sliding his hand over his own dick, lifting the shaft he found that he already had a semi and after a few quick pumps he made it stand to attention.

The smile that spread across the man's face was almost comical. He quickly shuffled over to the bedside table, his pants still down and counted out a stack of hundred dollar bills before stuffing them into James' jacket pocket.

"Come and sit." He said, patting the edge of the bed.

James did as instructed and sat on the edge of the bed with his feet on the ground. The man went to work immediately, pushing James back lightly he lowered his mouth eagerly over his erect cock and slid his wet lips over the tip. The man's tongue swirled around the top of James' dick while his lips pulled tight on the shaft. With a practiced skill that James' had never experienced before, the man slid his mouth down the whole length of his 9 inches and swallowed his dick into his throat. The man's lips hit the base of his cock where his bush of hair used to be and he could feel his throat contracting on the tip.

James gasped. He could feel an orgasm building. Holy shit... He was going to cum in this guys mouth. He was about to cum from 30 seconds of dick sucking from another guy!

The man suddenly slid his mouth back up James dick and the pressure released. James was breathing hard, but he could control himself now and he managed to stop himself from exploding. The man slid his tongue over James' dick again, sliding it down the shaft and onto his now completely smooth balls.

"Lift your legs." The man said, while pushing James' legs up into the air.

James held his legs up as the man's tongue slid over his balls, he took one of his nuts into his mouth and sucked on it lightly. There was something insanely hot but so wrong with this that made James' raging hard on ache even more.

It happened almost without James' knowing. One second the man was sliding his tongue all over his dick and balls, exploring his most private of places with the tip of his hard wet tongue. The next he had pushed the end of his tongue inside James' ass.

The sudden invasion made James' jump but he found the man's grip on the leg that he held up to be surprisingly strong. Once he got past the initial shock, James realised that while feeling a bit weird, it was not an unpleasant feeling. The man continued sliding his tongue over James' asshole, lapping at the outside before sliding the whole tongue as deep as he could. After a few seconds of this though, he began pumping back and forward with his tongue, fucking James' ass with his mouth, the man's tongue pushing in by an inch with each thrust.

James found himself holding both his own legs up as high as he could to give the man access. He let out a deep moan as he lay back and lifted his ass a little higher for the man to get better access. He had never felt anything like this. His whole body was tingling and his cock was throbbing against his stomach without even being touched.

Laying back into the mattress fully, James lifted his legs as high as he could. His bent knees were bent back to his chest and his feet were over his head, letting go of his grasp on his thighs James reached down to hold his butt cheeks out of the way so that the man could get his tongue even deeper.

The small man began using his finger to stroke from James' dick down over his nuts to his hole. He gradually moved his finger closer until James could feel the man slowly poking the tip of his finger into his ass along with the man's tongue.

James gasped as the man pushed his finger in to the first knuckle. He had never had anything go in there from this direction, but after the tongue fucking he had been getting it felt perfectly natural. The man pushed his finger in a bit more and James' could actually feel him start to stroke the tip against the inside of his ass. James started to sit up at the weird feeling, but then the man hit something inside him and he fell back with a loud moan.

"Holy shit!" James blurted out. He couldn't help it. That felt amazing. He started trying to push against the man's finger. He wanted to feel more. He needed to feel that again!

The man slid his finger out until it was almost completely out of James' ass and then thrust it back in again. Once inside him, the man rubbed against something again and the intense sensation made James' dick jump. Pre cum was dripping from the end of James's cock in a sticky thread that pooled on his stomach.

The man had stopped licking his ass now and focused on pumping his finger in and out of James' hole. It felt incredible. James started pushing against the rhythm to try and help the man's finger get deeper and hit that sweet spot. This must be the "P" spot people talked about. He had thought that was just a load of shit some girl made up because she wanted to fuck her boyfriend with a strapon.

A slight stretching feeling followed by more intense pleasure brought James back to the present. He sat up slightly so he could see what the small man was doing and saw that he was now sliding two fingers into him with as much ease as he had one.

The man smiled up at James when he saw him watching. He then took James' cock by the base and held it straight before dropping his head down over it and swallowing the length again.

The man wriggled his fingers inside James as he took the whole length of cock once then lifted his head off completely. James moaned again. He could barely breath, the sensations were so intense.

The man slid his fingers back out of James' ass. Much to his own surprise James let out a whimper of disappointment, sliding his ass closer to try and keep the man's fingers inside.

The man stood up and grinned at James.

"I will get lube. It will feel even better with lube. Roll over" The man turned to the night stand and James found himself obeying the instruction. That had felt amazing. James felt incredibly ashamed at the thought, but as he rolled onto his chest with his ass in the air he hoped the man would use his tongue again.

As though he had read his mind, the small man came back and immediately stuck his tongue deep into James' asshole. After only a few seconds of sliding his tongue in a circle around the James' slightly looser hole the man squirted something a bit cold over the entrance and started rubbing it in with his fingers.