The Gamble

Steven walked into Barrys home, shaking with anger and excitement at the prospect of another sexual encounter. He stood in the living room and before being asked he took off the clothes covering his ex girlfriend’s skirt and shirt, trying to convince himself that he did not enjoy the thought of what was going to happen.

Barry appeared from the kitchen with a bottle of red wine and two glasses, as the older man poured the wine out he looked Steven up and down, smirking at the younger man. “You do look very attractive, and I can see that you are very excited” he said spotting Stevens hard cock under the skirt. Steven didnt say a word, he kept his eyes locked on Barrys hard cock. It was much bigger then he remembered and thoughts rushing around his head of what was going to happen pushed Steven closer to breaking point.

“Barry, delete the video... I will do what you want but not until I see you delete it” he blurted out to the Barrys shock.

“Do what I want? Interesting, tell me boy. Every day at least four times a day I have heard you masterbating and moaning. All the time thinking about me? Tell me... what did I do to you in your depraved little fantasies”

Steven went red, he could feel the pressure of his erection against the panties

“I tell you what Steven, I’ll just sit here and listen whilst you tell me and once you finish telling me you can sit down and watch me delete the video”

Steven thought about this for a few seconds, he thought to himself that if he told Barry the truth of all the different fantasies he could easily say after this whole ordeal was over that he made it up to see what would happen.

“Well Barry” He said picking up a wine glass and taking a big mouth full. “Most of the time it was me just replaying what happened that night you came over” When he finished saying that out loud he locked eyes onto Barry's cock again, it was a monster. “But other times I was picturing myself either on all fours whilst you... made love to me or on my back whilst you did that...”

Barry signed Steven to come over ‘At least he will delete it now’ Steven thought, as he went to lower himself onto the seat Barry grabbed his waist and pulled him onto his lap. Pulling his phone out of his dressing gowns pocket Barry positioned his hands around Steven so he could show him the video in full. Both sat their watching, Steven felt sick to his stomach, everything was hitting him at the same time.

‘Oh god, what am I doing... Sitting on a grown mans lap, watching myself pleasure him... and Im going to do it all again I know it’ once again Steven turned bright red at the thought, but this time it was not because of the shame he had felt but the feeling of the older man's cock between his butt cheeks and the realization that Barry was ever so slightly rubbing himself against Steven.

Both sat there, slowly dry humping under their clothes without saying a word, once the video had stopped nothing was said as Barrys hand slowly ran up Stevens leg under the skirt he had been forced to wear, slowly inching towards the young mans rock hard cock. For a split second the older man hesitated. This wasn't the easy target he had used a few nights before, Steven was now here to get the video deleted and go.

“Please” Steven whimpered after a few seconds and went dead silent once more, slightly turning his head to Barry and once again almost tearing up “dont stop”. With that Barrys hand reached for the young mans cock and grabbed hold of it, the only thing between the skin on his hand and the sweet virgin meat was silky cum stained underwear. After a few seconds Steven, not knowing what he was doing dismounted Barry and turned to face him, pulling back the older mans dressing gown he straddled him, making sure that the older mans cock, fully erect, brushed up against his own almost lifting the skirt up.

Feeling the older cock brush up against his tight panties was intoxicating for Steven, as he kept rubbing his own cock against the other he no longer cared about holding back.

“If you delete the video, I will give you oral pleasure” Steven said cold and emotionless, leaning in towards Barrys ear and finishing with “You can have every inch of me”

Barrys cock twitched slightly at the thought “Such a shame though, I have been watching it every night and wanking myself silly” he proclaimed “I know, I will make you a bet” with that Stevens airs pricked at the thought of winning, the older man playing his addiction against him. “One game of pool, if you sink the black and win you get £30 per ball left on the table, I delete the video but you must still give me oral pleasure. Once you win and do that the video will be deleted and you never have to worry about blackmail again” he paused looking into the eyes of the young man “but you would be free to come and enjoy my thick cock if you wanted” . Steven stayed silent waiting for the catch.

“For every ball left on the table if I win they have a double meaning, they will represent one day that you must give yourself to me completely and they also will be one thing you have to do for me no questions asked. You would submit to everything... do you understand?”

Steven at this point was thinking hard, but never thought about declining; ‘I beat him, I suck his co... give him oral pleasure... he deletes the video and I get money... but on the other hand... I lose... I have to pleasure him and more’ after a few seconds Steven agreed to the rules and they headed into the games room and approached the table.

“Instead of heads or tails for rack and break we will be a bit more.... fun... bigger cock breaks and little cock racks” Barry said with a hint of dread in his own eyes now, it had only just occurred to Steven that he had never shown Barry his size and there was a reason.

Steven had always talked a big game but when it came to lights out and trousers down even fully erect he only stood at a small 5 inches long so looking down at Barry's cock he knew he had lost to what he could only size up as 7 to 7 and a half inches which was now clearly on display as the older man's gown once again parted. Steven without putting up a fight pulled the skirt up and his panties down revealing his cock. Barry let out a bellowing laugh at him “rack up needle dick” he said tieing his gown up.

Without fighting back the younger man turned to the table and bent down to pull out the balls to rack and was fully aware that he was now showing off part of his ass to the older man. Something came over him, an urge to tease rushed around his whole body. Slowly he racked up knowing full well that Barry was picturing in his own mind what he would do to him and it made Steven want to explode.

‘God, why is this so exhilarating... why do I want him so much?’ his train of thought quickly interrupted by the footsteps of his challenger walking to the other side of the table, he stood upright and looked at Barry wondering how far he could push his luck.

“Barry, are we counting fouls?”

The older man looked at him and smiled

“Yes Boy, every foul I make will be £10 to you and you can ask for a ball value, say 3 balls left if you lose and I tell you what it is you will need to do, but if I still have balls up and I pot the black then all bets are off and you get your wish, the video will be deleted and you need not do anything”

A feeling of joy and disappointment came over Steven, the joy of being free is a chance but he had convinced himself he would pleasure the older man and was enjoying the idea of doing it again

“And if I foul?” Steven said nervously, clearly aroused at what was suggested. Barry stood there for a second, not having thought this far ahead but it didn't take long for him to come up with an idea “Well Steven, if you foul you have to act more girly for me. I have plenty of things you can use and wear to make yourself look even cuter”

With that comment Steven blushed as Barry took his eyes off of the young man and bent over to break, as he pulled the cue back he quickly looked up at Steven and said cold and direct “normal rules apply, pot black off break or out of turn and its an instant loss” and with that the cue smashed the white ball into the leading red and balls flew around the table. As the controlled chaos started to slow down Steven noticed the black ball edging closer to the far side pocket. This was it, the first shot of the game and Barry was going to lose. He was free.

Silence

The ball was creeping towards the pocket, there was nothing Barry could do to stop it. He knew he had lost and he pulled out his phone to delete the video muttering under his own breath trying to work out how much he owed and contemplated all the things he would not be able to do to the young man. Then startled by a loud bang of wood on wood, looking up at Steven the black ball had stopped and was rolling the other way as Stevens cue rattled over the table.

“Sorry, I fouled” Steven said quickly with a hint of shame and excitement, but it was too late, the video was forever gone as Barry looked down sadly at the phone in his hands but then looked up smiling.

“You fouled? you could have won and been out of all bets Steven” he said quizzically.

“Sorry, I thought it was my shot and accidentally stopped the black from dropping” Steven replied.

“O..k...” Barry replied still confused but slowly catching up with what was going on “So, your first foul, we will start simple but you get to shoot again but as I almost lost I will tell you about the first few fouls if you were to make them. But your first is a new name.... something simple to remember... I know, your ex’s name Sarah!”

Steven cringed at this, knowing how much pain he had gone through with the break up could Barry really stoop this low? Making him first dress in her clothes now use her name. He opened his mouth to argue but all that came out was “Ok”

“Your next forfeits are a bit more....physical.... Wig, then make up but after that you tell me every single dirty thought you have ever had”

With that Barry gestured towards the table as the newly named Sarah picked up his cue and took aim, now thinking solely about the forfeits he could not concentrate and struck the white ball completely missing a easy shot but as soon as he stood up Barry announced “foul”. Steven looked up confused; “I merely pointed at your cue, its my shot” with that Barry walked out of the room for a few minutes and returned with a blonde wig handing it to the young man.

“Now not only are you called Sarah, you look ever more like her now” Barry chuckled as the young man put it on begrudgingly. “So Sarah, its my shot” with lightening reflexes he bent over the table and sunk 2 balls in one shot, lining up the next he looked up at his new dressed up boy and hit the white ball, no balls went down. Barry stood upright and moved away allowing Steven to bend over the table to line up a shot.

“Just think Sarah, if you miss this shot you have to put make up on. Even worse if I 7 ball you thats 7 days of being my plaything and 7 things I get to do to you on top of having you slobber on my cock and calling you a faggot”

Steven whimpered, managing to control himself from fouling again but instead of taking the shot he stood up and turned to Barry.

“You would call me what?!” Steven said, shocked at such a comment. Barry repeated the word as he could clearly see Steven’s cock twitch with excitement. All Steven did was stand there, clearly thinking about something but Barry was unsure what.

Steven looked Barry up and down then turned to the table. Standing completely still he weighed up his options and walked around the table. Without saying a word he bent down took aim and hit the white ball, a dead straight hit into the black which fell into a pocket followed by the white.

“Oh no” Steven said “You 7 balled me”