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By (user no longer on site) OP
over a year ago
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She looked up into those green brown eyes a look of fear and love in them at the same time.
She had decided after a few months to test he supposed devotion to her he was 11 years her senior but he was probably the sweetest and most sincere guy she had ever met. She knew from their private camming sessions he was will to endure some pain but she had to know how far he would go even if it meant breaking the no meeting rule he just intrigued her too much.
The problem was the way he wrote and how he wrote every time she thought he couldn’t surprise he couldn’t make her think dirty delicious thoughts he would send a small message with enough to tease and seduce her brain into thinking all manner of things.
Well it was two months since he wrote to her of him tied and crying as she enjoyed his pain and so far she had managed to get him naked hands cuffed behind him spreader bar around his ankles the rubber gag in his mouth she loved its pink colour. The one toy for him she had bought to the party was a reasonably sized vibrating butt plug this had been lubed and roughly inserted before the gag went in she needed to hear him gasp.
So she had the scene set she was sitting between his bent legs her legs encompassing his ass her slim frame fit perfectly she was wearing a black and white American high school type sports sweater the kind with the big numbers on and a pair of perfectly white cotton panties with a little pink bow on the front . Well they were nearly perfect except for the small wet patch forming at the front where her moistness was beginning to show.
Just her presence and being tied up by her then the removal of everything but these items of clothing had him rock hard, maybe he did actually love her. She was impressed by his cock in the flesh it was a lot meatier than it looked on cam and so solid to the touch as she wrapped her hand around it and pulled his foreskin back over the head, she noticed the new bar with the larger balls in his piercing and couldn’t resist swiping her tongue over it to flick it causing him to groan into the gag and to seep some precum onto the top of his cock.
Smiling she reached to her right and picked up the small case which he had bought and then brought to her she unzipped it and stared at the contents all bright eyed like a young girl opening her xmas presents to find her favourite dolly inside.
Her beautiful yet dangerous nails tinkled over the stainless steel implements inside and she plucked the first and smallest rod out of the case. She bought the end to her lips and slowly slid it in coating it in saliva and warming it slightly she then played it across the head of his cock coating it in the precum, she felt his cock pulse in her firm grip.
Looking up into those beautiful eyes of his , he did have lovely eyes she slowly pushed the tip into his cock it slid in just a centimetre or two and she heard his breathing quicken then she pushed further not letting him adjust until her thumb and forefinger were against the head of his cock.
She saw the pain in his eyes and watched the trickle of the tear run own his face from the left eye one forming in the right she smiled
“ It’s OK monkey miss is liking it and monkey wants miss happy yes ?”
He nodded his agreement through blurry eyes the pain was something new to him yet his cock remained rock solid and he did want her to be happy he did truly love her .
“ Well that’s good monkey because I plan on using them all today in this first session and the very last one is as thick as my finger” she said while holding her index finger in front of him .
His face changed to that of fear but he didn’t struggle he looked at her knowing she meant it he also knew he pledged his body to her to do with what she wanted he knew she liked pain receiving it this he had seen but he did not realise how much she cherished giving it out too .
The look on his face made her shiver with excitement she felt her panties begin to soak she knew she would need to release the pressure this session would build and she knew how too but that was in the future. Leaning forward she used the very tip of her tongue to lick the tear trickling down his right cheek.
“ Now you’re going to be a good monkey for miss and not struggle feel free to scream the gag will drown most of it out and miss will like it if you scream for her “
Smiling she quickly withdrew the sound reaching into the pouch she evilly picked up not the second width one but the third and proceed to force this down his cock the pain was unbearable he was in full tears now a silent scream from behind the gag caused October to shiver again this time when she withdrew it she only did so three quarters and proceeded to force it back in like she was fucking his cock with it she repeated this motion several times loving how his cock pulsed and the silent screams form behind the gag.
By the time she reached the eighth and final sound his was dripping in sweat his eyes were blurry he had given up screaming as his throat hurt he looked as she poured some lube onto it it was easily thicker than a good fountain pen . The thing he was amazed by was all the pain she had caused him and his cock was still hard as steel .
He watched her begin pushing it in slowly like all the others what he didn’t expect was the hard quick shove she gave once just few millimetres were in she bottomed it in his cock in one going causing his whole body to jump and lurch and he found a scream from somewhere. She smiled at him and took his head in her hands to calm him gently stroking his face .
“ Shh monkey shh its nearly over then we have some fun “
She proceeded to use this new thicker sound to pump his cock hard really hard she hard gripped in her fist and was pumping so hard on the down strokes she was squashing his cockhead slightly setting off every nerve ending there like fireworks. After several minutes she kissed his cheek and withdrew the sound from his thoughly abused cock .
She wiped it clean and returned it to the case as she had done with all the others his urethra was still open a few minutes later as she stood up in front of him he could clearly see her arousal at his pain her whit panties were see through at the front where her juices had gathered and soaked the panties.
She walked over to the side of the bed slipped the panties off pulled the sweater over her head to reveal the Nike sports bra he had joked would be perfect for their strapon fucking sessions . She stepped into the plush velvety harness he had bought with him and to which there was attached one of his 12 inch black thick dildos. October popped the small but powerful bullet vibe into its pocket an cinched the harness tight to her hips feeling the vibe against her clit .
He was so exhausted when she pushed him with her foot he fell to his side she used her foot to push him onto his knees and due to the binding of his ankles and arms he found his face against the carpet. Not wanting to cause his face damage October fetched a pillow of the bed and placed it under his head .
His next sensation was the vibrating plug being yanked from its home which it had gotten very accustomed to the head of the dildo quickly nestled against his asshole , he knew the plug was a lot smaller than the monster cock she had strapped to her waist he braced himself while trying to relax his ass.
October didn’t care if he was ready or not she needed release and she was going to get fucking the life out of his ass till she too was a sweaty messy heap of pleasure . She violently thrust forward jamming half of the monster dildo into him he groaned and she paused long enough to turn the bullet vibe on and almost came instantly from the strong pulses against her already sensitive clit .
She pulled halfway out and thrust hard again pouring some lube onto the toy as it slid in . After three to four more thrust she had the big black cock’s balls against his she leant over his back and whispered into his ear .
“ You’re a good boy monkey miss is going to fuck you like a little bitch now so hold on tight baby”
She slid the massive toy out to its head and drove the whole length back inside him slamming her hips into his ass she continued this paced and ferocious use of his ass until she had her first orgasm he felt rather than saw her cum . Her thrusting became erratic and he could feel the toy shake in his ass along with her body tremors .
Thinking she was done he started to relax but as her composure returned so did the thrusting she managed to eek out another two orgasms for herself before eventually collapsing covered in sweat and her juices running down her perfect thighs she draped over his back and whispered into his ear ,
“I love you monkey and you will be my monkey forever “
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