The Gamble

by Tim Bagging

17 Apr 2015 974 readers Score 7.7 (26 votes) PDF Mobi ePub Txt


Steven laid in bed, it had been days since he last saw Barry and experienced his first male interaction. The moments leading up to what happened had slipped his mind but what he actually did hung there almost for the world to see whilst all the time wondering if Barry really had recorded the blow job. ‘Blow job’ Steve thought to himself, ‘thats all it was’ safe in the knowledge that if he used his own words and made it as clinical as possible he would soon forget it but no matter what he thought it stayed in the front of his mind; and once again it was making him hard. Once again he had not noticed himself, hand on his own cock and stroking slowly ‘it was only me sucking his coc...’ quickly shaking his head and releasing the grip on his own member he stood up.

Darkness all around him, the bills had been paid but he chose to stand in his darkness to calm his mind and soul. Looking around he could see his own discarded tissues used to catch his own cum or wipe it off himself in the masterbation binge he had been having and for the first time he decided to sucumb to the thoughts and the pleasures; closing his eyes he sat down in his bed and pictured Barry next to him as it was a few nights before. For a few seconds Steven sat there, he could feel his cock getting harder. Since the one night with Barry, Steven had been watching as much straight porn as possible and wanking to try and prove something but at this moment he finally gave in to the sexual desire.

He laid upon the bed slowly tossing himself off, eyes still shut and thinking of being on his knees in front of Barry, slowly sucking his cock. Steven started to softly moan as he pumped faster remembering the cum flooding his mouth and the strange excitement that came with it. Only in his only little fantasy Barry didn't stop cumming; a warm sticky torrent coating his throat and mouth, lips, face and body. Steven could feel that he was going to explode and he began to moan loudly under his own breath he muttered “Please let me suck it” and so much more. At that very moment the intense session was interrupted with a loud shriek emanating from his phone.

Steven locked eyes on his phone and picked it up, Barrys name and face once again lit up his screen. He had been avoiding Barry for a total of 4 days, every day without fail he would call Steven 4 or 5 times and in a moment of madness, Steven answered; cock still in hand but now softly stroking.

“Hello?” Barrys voice echoed in Steven's mind forcing out a tiny whimper

“Hi Barry” Steven replied, trying to calm himself

“Im just calling to make sure you are ok, we haven't seen you in a few days and we..”

“I have been busy, doing house ... things” Steven had quickly cut Barry off without a thought out reason.... ‘house things’ he thought to himself ‘how stupid do I sound’

Silence descended for a few seconds

“Well, ok. Steven I have called for another reason” Barry smoothly let out, at this point Steven could feel himself getting tense, worried but more so aroused as he started to increase the pace of his own pleasure

“Whats up?” He replied now locked in the thought that Barry would either suggest more oral fun or apologize all the time hoping it was the first.

“Noise” He said softly down the phone to the younger man

“Huh?” Steven at this point very confused.

=====================================================================

“The last few days I have heard your headboard banging against the wall, as you know they are thin between the houses and I have heard a lot of moaning. I called this time because I heard you shouting”

At this point the pin dropped for Steven. Barrys calls had all been the same time he was wanking and almost always close or during climax.

“Its ok Steven, I don't mind but if you are going to have girls over try moving your bed away”

“I haven't had any girls over”

“Ok, if you're going to have guys over”

Steven almost snapped at him

“I HAVEN'T HAD ANY GUYS OVER”

“ok, ok... Im just saying and Im not judging you Steven. But a few minutes ago I could hear you shouting please let me suck your cock and please fuck me hard. All Im going to say is that Im fine with your sucking off other men. We never have to do it again if you dont want to but if you are going to carry on doing that in your room please either move your bed away and keep the sound down or..”

Steven hadn't thought of other men doing this to him but now Barry had put the idea in his head he was pumping faster again. He was praying the “or” would be to go over to Barrys now.

“You can be louder, I don't mind laying here thick meat in my hand beating off to the sound of you being fucked”

With that Steven let out a massive moan. He could picture Barry next door wanking over the thought of it all

“So tell me boy, do you have another man there? Or are you just playing with yourself?” Barrys tone turning dirty and almost abusive which for some reason made Steven shudder with excitement, both could hear the other tossing away; Barrys slow and methodical whereas Stevens was frantic.

“I am on my own Barry” his breathing speeding up

“Shame, tell me boy? What are you fantasizing about?”

“Girl from work Barry” some how Steven wanted to be called out on his lie

“So this girl has a thick cock you want to suck and be fucked by? I doubt it. Tell me, are you picturing my cock plowing your sweet mouth?”

Only moaning from Steven could be heard over the phone as the slapping on skin on skin carried down the phone to Barrys ears.

“Or are you picturing me taking your virginity boy, my cock deep in your sweet round ass pounding away”

With that Steven’s body arched as he exploded over his stomach, moaning deep and heavily over the thought of this older man abusing his body. With a few last strokes he laid back down flat on the bed drenched in sweat and cum and exhausted.

“Did you enjoy that Steven? Picturing me behind you fucking you like the little gay boy you are? Shooting my load deep inside you”

Only silence now from Steven, he stayed completely still; cock still throbbing and his own cum dripping down his body breathing heavily not knowing how to reply to the man who he  had given oral pleasure to, the same man who had just made him cum unlike ever before without touching him.

‘What am I doing... I can't be enjoying this can I? When it was just me laying here I was fine but his voice has made me do this’ Steven thought to himself ‘shit, hes waiting for me to reply.. think of something man and whatever you do don't say yes’

“Yes” Steven then said, the word stumbling out of his mouth and instantly slapping himself on the forehead

“Do you want to come over boy?” He quizzed Steven

‘dont say yes! DONT SAY YES!’ Stevens mind raced

“Yes”

“Its not that easy though Steven, you still really do owe me after the other night and I am feeling frisky and slightly evil” Barry grunted over the phone “Do you still have some belongings from your ex girlfriend, boy?”

“Y...Yes” Steven nervously replied

“Good good, she was a hot little thing wasn't she, always walking around in her skimpy little outfits. Showing her panties off to the world as she would never shut the curtains. Do you still have her black underwear and skirts?”

Steven had an idea what was coming next, he knew that his was stepping completely over the line and that he would never dress up for another man. Even the idea made him feel sick to his stomach which quickly showed as his once hard dick shriveled away.

“Yes” he said firmly

“Good, dress up for me and come over. I need some fun and I do like the way you shake your ass when playing pool so seeing it in panties and a skirt will surely make me a very happy man”

“No” Steven announced “I will not dress up for your sick pleasure. As I said to you that night I am not gay and I will not take part in your sick perverted games and there is nothing you can do or say to make me” with that Steven let out a silent sigh thinking ‘its done, Im free and I know I'm not gay, it was fun but thats what it was, fun’.

“Really? Thats not how I remember it, I merely suggested you get some paper towels to catch my cum. I gave you every chance to say no and walk away, you were the one who sucked my cock” Aggression building in Barry's voice was instantly recognisable to Steven, “You were the one who swallowed as much cum as you could weren't you, you little cock sucker”

Something at that moment clicked in Steven’s mind, not a violent outburst or a debate but something completely different. Acceptance, it was him that did it. Never really asked and he did do it on his own.

“Well?” Barry demanded

“Im still not going to do it Barry” Steven said softly not sure what he would do to get out of the situation

“Well Steven, thats a shame. Thought you were smarter then that, making a bet against me losing and paying for it on your knees was one thing but imagine what people would say when they see the video of it. I've watched it over and over boy, you obviously loved it”

‘Blackmail’ Steven thought ‘he wouldn't would he?’

“You have 1 hour to make up your mind Steven, think about it”. With that the phone went dead, Steven laying there in his own cum speechless. The whole weight of the situation slowly beared down on him, the fear that people would find out that he did actually enjoy a mans cock. If he had shown some restraint that night he could have claimed he was forced to but it was obvious that he did love every second. Even when Barry was on the phone to him; he knew that he was enjoying every second of it but the only thing that was in Steven’s head now was a simple question.

‘If I dont do this... will he drop it completely? We go back to just playing pool and I never get to try THAT with him again... maybe if I do this for him’

“No, Im not gay” he proudly announced to the shadows cast from the sun bearing down through the windows of an outside tree. He would never bow down to this man in this sick manner he thought. ‘And there is one way to make sure he doesnt ask again for this dressing up thing, I must get rid of what clothes she left here’.

===================================================================

Steven walked to his wardrobe and opened it, as he thought only one plain black skirt. ‘Bin’ he thought as he chucked it on the bed and turned to his bedside cabinet. Opening the bottom draw, something he hadn't done since his ex walked out on him, it was full of toys, photos of her and what was left of her underwear which ashamedly he had pleasured himself with the same night Barry used his mouth as a cum dump.

‘A cum dump.... that cum, the big cock....’ he started to think holding the knickers in one hand and a small dildo in the other ‘it wouldnt hurt, one time.... and then he might let me go back to my normal life...sometimes..doing that again...’ broken thoughts and fantasy started to shoot to the front of Stevens mind. For a few seconds he considered wearing them, how embarrassed he would be and how humiliating it would be in front of another man.

Steven looked down, a deeply empty feeling struck him as he saw his own cock rock hard feeling true humiliation when once again his world was shook by a text alert on his phone. Standing completely still for a few seconds contemplating what to do, he dropped the dildo and picked up the phone.

*********************************************************

From Barry

You have 45 minutes, Im ready to upload this video

*********************************************************

Seconds later a picture message popped up of a screen shot of Steven sucking the older mans thick meat. ‘Hes going to do it. Hes going to upload it’ Steven dropped the phone onto the bed and looked at the panties in his hand. ‘Blackmail....’ a single tear ran down his face. With that, Steven slowly put the panties on, followed by the skirt on the bed and finally managing to pull his jeans up over the skirt to hide it.

Slowly he moved from draw to draw to find the matching bra, tears now streaming down his face. After a few moments he found it, struggling to put it on, much like taking them off he was no where near an expert as he had always made out to be to the ladies. Walking back to the wardrobe he picked a white shirt and put it on. Looking into the mirror he could clearly see that his cock was rock hard.

‘This is disgusting, what the fuck am I doing’ he thought once again as he grabbed a coat and made for the front door slowly, still crying he reached for the door handle and opened it, a flood of light hit his face almost blinding him for a moment. ‘There’s no one around’ he thought quickly causing him to shut the door and run next door to Barrys house, ringing the doorbell frantically what was only a few seconds which felt to him like an eternity wondering if anyone had seen him.

The door crept open to reveal Barry standing in a dressing gown, cock clearly visible with signs of pre cum.

“Why are you crying? If you dont want to do this you can go home. If you dont like it, dont do it” he said, feigning some sort of emotion for the younger man

“Im crying because...” Steven said before stopping himself

Barry looked on at him, almost saying with his eyes ‘Go on, because...’

“Because this is sick, fucking sick. Vile. Perverted. You have me standing here wearing...THINGS.... blackmailing me into doing what you fucking want.” Steven said with deep breaths trying to calm himself down “I feel degraded, humiliated, used and sick to my stomach” he finished. Barry looking at him almost laughing at the young mans pain. Steven met eyes with Barry and said “And I want more”.

Part 3 coming soon

by Tim Bagging

Email: [email protected]

Copyright 2024