Simon's Strict Unseen Mistress

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A young man becomes a willing slave... but doing what?
2.7k words
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flash87
flash87
13 Followers

He wasn't sure how he was going to get out of this... or how he really got into it. His legs were bound tightly, his calves pushed against his thighs and tightly bound in something strong, probably plastic. His arms felt the same, his forearms to his biceps and again bound tightly unable to move. The rest of his body felt mostly bare, a chill breeze passing over his exposed buttocks and up his back. The only other things he could feel was the ball gag in his mouth, the eye mask on his face and something around his cock... all encompassing, cold and solid.

'You're awake then...' there was a short pause 'finally'.

He froze, the woman's voice measured and stern and he was suddenly aware of just how naked he thought he was. He could feel his penis retract at the thought of someone looking at him in whatever state he was in. He dared not move... even if he could.

He expected the voice to continue speaking but there was only silence. At least a minute passed... finally he tried to turn towards where he thought the voice was coming from and tried to speak a muffled meek hello through the gag.

'ha ha ha ha'

The loud, shrill laugh from the same voice made him freeze again, but this time there was a sexiness to it.

'good morning Simon. I wonder if you remember how you got here? That little cocktail can lead to some forgetfulness, but I had to have you out cold to get you here where I wanted you... and set up... like I wanted you.'

Simon vaguely thought back and his mind pieced together how he'd got here. He'd found her online, an add from someone local looking for someone 'up for anything' on craigslist. He was a slim, attractive young man of 22, mousy blonde hair, blue eyes and fairly well hung yet not overly successful with women. He wasn't that interested in the boring dating scenes or vanilla one night stands that most of his age group were which had led him to finding his kicks on the darker places of the internet. It had been a strange correspondence. He'd emailed and tried to start a friendly chat... but his only reply was a word document. In the document a questionnaire... a long detailed questionnaire asking about every fetish you could imagine and how each made him feel, would he be interested and the like. Simon was keen to try new things and although some of the ideas had scared him he'd enthusiastically answered pretty much everything... although he was now thinking this may've been a bad move.

Once he'd completed the questionnaire he replied with many questions of his own trying to find out more about this woman. In response all he received were the instructions and a picture, his questions had been ignored. The instructions had told him to meet at a bar he'd not visited before and order a 'sub potion' from the barmaid and sit in the booth at the back. The picture was low resolution and blurry but showed a tall, slim dark haired woman in a pvc body suit... the picture was sexy but it didn't say it was who he was meeting and he couldn't see her face or much more than her outline. Yet all these vague details and inherent danger had only made him more excited and he went to the bar, ordered the drink, sat in the booth, waited, drank... and now here he was here in this compromising state.

Back in the room he heard a rustle of papers.

'I enjoyed your responses Simon. And as per your instructions I have you for the entire weekend. But it's up to me what happens from now on. Hmmm, let me see. Shall I... '

There was a further pause and more rustling of papers.

'It says here you weren't that interested in watersports... maybe I'll make you my piss slave.'

Simon froze, the pee and shit questions were the only ones he'd drawn a line at. Was this going to be bad?

'Maybe I'll pee on your face, and feed you on your pee for the next few days. HA HA HA.'

The shrill almost evil laugh pierced Simon and he sat there very quietly, bound on the floor worrying what was to come.

'Luckily for you though I'm also not that interested in that. Although this isn't going to be all fun and games for you slut. I'm going to remove your gag now. Listen to my instructions carefully, this is your only warning. If you speak out of turn or without the due respect I deserve you will be punished. Do you understand?'

Simon nodded and tried to say yes through the gag, which again made the voice laugh. Simon heard the click of heels walking towards him and felt the gag firmly ripped from his mouth. He led on the ground, still, waiting for what she said next.

'For god's sakes get up... On all fours... now'

Simon scrambled to obey the voice although he wasn't sure how he was going to do this bound in the way he was. It took a couple of attempts to balance himself on his elbows and knees but finally he did it.

'Tut tut tut. A shameful display. I'm not sure if this is going to work out. Do you want to be my slut, slave? Or am I wasting my time?'

Simons cock twitched as he heard this and he realised at that moment that he was wearing a chastity cage around his cock. His penis quickly grew pressing against the sides of his plastic prison. It was a feeling he was unfamiliar with but it only made him more excited. Simon took a moment and gingerly replied:

'yes...I want to be your slut'

Suddenly he felt an intense pain as his balls were slapped hard making him let out a feminine cry. The initial pain and his balls slapping against the cage caused him to teeter and slip losing his balance and crashing back to the ground.

'MISTRESS' she said. 'You will refer to me with respect you little faggot.'

Her voice was angry, harsh. Simon was worried. He hurt.

'Get back on your knees now. But this time with some respect.'

He started to clamber back to his position quickly, trying not to anger his new mistress.

'Sorry Mistress' he gingerly said.

SLAP. Another blow to his balls and he fell again with a whimper.

'DO NOT SPEAK UNLESS SPOKEN TO.' She bellowed. 'Again, up. This time with some poise slave. Ass up, back arched. If you get it wrong this time I may have to call in the boys.'

Again Simon rose to his knees and elbows and pushed his ass into the air. He felt exposed. Helpless and a little scared, yet his cock was pushing against his cage harder than ever before. He had no idea who the boys were or what they would do... but he sadistically wanted to find out.

'Better... although it seems maybe you want to get it wrong' she said in a teasing manner.

He could hear her walking around him, heels clicking on the floor. She stopped behind him and for the first time he felt her touch as she grabbed a firm handful of his ass cheek with a PVC glove. It was taking all of his concentration to remain in position and this touch was sending his mind reeling. She loosened her grip and ran a finger playfully over his left cheek and then across to his right making swirling motions before running it over his exposed anus and down towards his balls.

'It's a shame you've been so poorly behaved. I was going to reward you for following my email so precisely. Yet your actions here must be punished.'

Her voice was driving him crazy. He wanted anything from her at this moment he told himself.

SLAP. His left ass cheek stung as she firmly spanked him, it took all of his will to not make a sound and remain in position.

SLAP. His right cheek equally stung. SLAP, SLAP. Left and right. SLAP, SLAP. He let out a whimper.

'mmmmm' he heard.

His whimper had aroused her he could tell, yet he feared making any more sounds.

SLAP SLAP SLAP SLAP. Four more blows on his ass cheeks and finally SLAP a crushing blow on his balls. Simon let out a cry and his legs and arms buckled, yet he remained on all fours only losing his poise.

'up' she said softly.

Simon quickly arched his back and pushed his ass into the air, resuming the position commanded of him. Simon heard her moving away, across the room and heard the clink of something and some other sounds he couldn't identify. This made him nervous, his cock was aching worse than ever and he longed for release. The heels clicked back towards him and he felt a cold cold feeling against his anus, she was applying a cold lube to his hole with her fingers. He wanted to say something, maybe stop, or maybe just be gentle as this was all new to him. He began to shiver as she probed inwards with a single cold finger.

'Don't worry slave... I'll really enjoy this.' She said wickedly.

Her finger probed him deeply, it was a strange feeling both uncomfortable and pleasurable. She slowly began to finger him in and out. His cock was staining now against the cage and he knew he was leaking precum. She continued to finger him very slowly and as the moments passed by Simon, almost involuntarily, started to push his hips back against the finger longing for more of this strange new feeling.

'now now, no one told you to move slave... although it is nice to see you enjoying your punishment... you're even making a little mess on the ground here. I wonder if you still will in a minute.'

Her constant teasing was becoming too much and Simon could feel his balls aching in a way that he hadn't before... almost like he was going to cum but no one had touched his cock. He was confused and frightened of what was to come but more turned on than he'd ever felt in his life. Her finger pulled out for a final time and Simon let out another involuntary whimper.

'Pathetic.' Her taunt sounded playful and only encouraged his aching penis.

She was moving around behind him and he felt both of her hands firmly grab his hips and something press against his puckered anus. He knew what was coming and wasn't sure if he wanted it. He wanted to speak so badly yet held his tongue fearing reproach. She held him there for a long time, the strap on pressed firmly against, but not, entering his anus.

'Tell me you want it.' She commanded quietly.

He took a moment and thought of how he should reply. Quietly he spoke:

'Please Mistress' he paused, not sure he could finish his own sentence 'fuck me.'

'Again.' She commanded. 'Ask for it like you mean it.'

'Please Mistress fuck my ass' He said more confidently yet as he was finishing the head of the dildo slipped into his anus and the word ass became a moan of pleasure.

The strap-on was cold and much thicker than his new Mistress's fingers. She was slow as she had been before, pushing just an inch or so in before pulling back out and repeating the motion. Slowly but surely she started to give him more of the plastic cock, Simon was now moaning continuously in a low heavy voice. As she pushed in further he felt a sudden warmness inside that he knew could only be his prostate and he ached to be able to touch his throbbing cock.

She was now firmly rocking him on his knees with her grip on his hips back onto her strap on and getting deeper and deeper, already she was as deep as her fingers had ever been, and the dildo was stretching him in a way that made it far more uncomfortable yet a million times more pleasurable. He guessed she was about six inches in when he finally felt her body pressing against his ass cheeks telling him she was as deep as it would go. The feeling was intense and Simon began to shake.

'There's a good girl' she said softly as she increased the pace.

She was fucking him hard now and he couldn't describe how wonderful it felt. He could feel an orgasm growing behind his aching cock and he was praying she would help him out. He felt her releasing his hip with her right hand and reaching around to his balls. As she gave his balls a soft squeeze he began to murmur:

'puh-puh-please mistress...'

But it was already too late. She pulled him harshly down onto the strap on and held him there as he convulsed, he could feel his cock spurting away immediately getting covered inside the cage. She held him tightly by the hips as his post orgasm embarrassment began to grow. She was silent as she let him go and slowly, carefully exited his ass. He could hear her stand.

'Bad boy' she said slowly.

He remained quiet. He didn't know what to say, or if he should say anything. He had loved every moment of his punishment... maybe more would be good.

'bad bad boy'

'Did you ask permission to cum slut?' she said, more firmly than before.

His cock was still leaking and he thought he could actually hear it dripping on the floor.

'No Mistress' He stated as confidently as he could muster... although it wasn't convincing even to his own ears.

'Well well, what will I have to do with you. You enjoyed your punishment far too much. Making a sticky little mess on my floor. Come here.' She said as she took him by the hair, leading him gently around in a circle and firmly yet gently pushing his head towards the floor. Simon knew immediately what was in front of him even with the blindfold on, he'd smelled it a million times before but never attempted what he was now sure she was going to ask of him. His cock twitched.

'Lick' She commanded.

Simon hesitated. He was going to eat his own cum for the woman who had just fucked him in the ass.

Gingerly he put out his tongue and felt the warm , stickly salty cum coating his tongue. It wasn't bad and his cock began to get hard again. He licked a few more times more enthusiastically and he felt her guiding his head around the floor to different spots.

'Good boy' she said 'who's my little cum slut?' she asked in a sickly sweet tone. Simon was too embarrassed to respond.

She pulled his head up.

'Back into position please.'

He obliged quickly arching his back and pushing out his ass. He heard a chair being pulled up behind him and presumably her sitting in it. There was silence for a minute and Simon remained in position as well as he could.

'You looked like you enjoyed your little mess there... makes me wonder what we should do with you next. Maybe you'd like some more cum in your belly... maybe straight from the source?'

She paused to observe his response. She wanted him to suck a cock? Or get fucked by a real one? He shivered again in embarrassment and his cock ached visibly against the cage.

'yes... well you look like you'd enjoy that. Or maybe I should keep you to myself. Dress you up like a sissy slut next time? But I'll have to stop that mess somehow... maybe you're not old enough to be a big girl yet... maybe you'll be my ickle little diaper girl.'

She was teasing him. All of these fetishes were in the questionnaire he'd enthusiastically agreed with and many many more. He was embarrassed... but more surprisingly he was getting totally hard again and precum was dripping from his cage.

'I think you need a rest first though dear. I'm going to go freshen up and get ready for our next session... see you shortly.'

He heard her rise from the chair and felt a firm slap on the ass followed by her walking away and a door opening and closing. He was still in his compromising position and wondered how he was to rest as his mind raced over what had happened and the possible humiliations to come.

flash87
flash87
13 Followers
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Sucker4BoobiesSucker4Boobiesabout 7 years ago
Not bad

This story fills me with anticipation! The pacing is great. I hate to be that guy, but you need to use double quotation marks when someone speaks.

AnonymousAnonymousabout 7 years ago
Good work

There's so little detail because he's blindfolded. He cant see the room hes in. Hot though.

FASfanFASfanabout 7 years ago
Now this is really promising!

Thank you for sharing your story with us and please write more -- it was very good indeed. Five stars from me -- and thanks again!

FailedscoutFailedscoutabout 7 years ago
Great Start!

This was a great start. It could have used a bit more detail and a bit more length but still a great start for a first? submission. Please continue.

Thank you for writing and posting here.

AnonymousAnonymousabout 7 years ago
Great start!

Great fantasy story!

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