My friend Matt had asked me if I wanted to help waiter his father's party and I jumped on the idea of some extra cash. I had saved for ages but was still stuck working minimum wage jobs at Coles and Blockbuster.

I was only at that job for about two months when Matt gave me the opportunity to waiter his dads parties for some frankly good cash. On this particular evening the party was nearly wrapped up and only a handful of men remained, they must have been some of Paolo’s (Matt's fathers) closest friends and colleagues.

I noticed their group looking at me and talking, I took no notice though as I thought they were talking about their usual banking escapades. Just as I turned around to admire the lush gardens I heard the thin glass windows open behind me, I quickly spun around to notice Paolo brandishing a half empty whiskey glass.

‘Hello Angus, how did you find tonight?’ he asked in a hushed voice.

Paolo was a sight to behold he stood slightly smaller than me at around 6 feet tall but he was much more well-built than my slender gangly self and very tanned for a Swiss-German man even after living abroad for so long he still spoke with a thick accent.
Compared to a lot of the other men at the party that night, he looked in good health for being 55, his hair was beginning to thin but was still black which was more than I could say for the thick silver curls protruding from his now loosened button up shirt.

‘Uh yeah it was fine’ I quickly replied noticing I had been silently staring for far too long.

‘I have to ask you something Angus and please don’t be taken aback.’

‘I heard you are having some problems with money and...well and I uh think I you.’ Paolo spoke quietly as he glanced behind himself making sure that no one would be joining us on the balcony.

‘Matt has told be about some of your interactions and well I know i’m older but i’m also willing to pay you for your services, Let me fuck you tonight and I will give you $500.’

My eyes widened as I tried to visualize that amount of money and as I visualized the sex with Paolo. I considered myself bi-curious and Paolo was at least an enticing prospect for my first ever sexual encounter.

‘Can I ask why you want to do this Paolo?’ I managed to croak out.

‘If you do this with me tonight I might be able to explain to you more than just why’ Paolo remarked with a wry smile.

‘Yeah fuck it, life’s to short not to enjoy it!’

Paolo turned and began walking back into the large main hall of his house and I swiftly followed him with my heart thumping in my chest. He walked me up to what must have been his master bedroom, it was an impressive sight a mostly black room with a massive bed that sprawled out and covered most of the room. The low ceiling was a large mirror and its only imperfections were 4 lights positioned above the bed, the room was dimly lit and the darkness was accentuated by the black carpet and walls in the room.

Paolo walked across the room and pulled back the frost glass window to his bathroom and entered.

‘get dressed and get ready’ he called from inside the bathroom

I began to remove my dress clothes and folded them neatly on a large leather chair positioned opposite the bed I then turned and sat naked on the edge of the huge bed with the headboard being made of a dark brown ornate wood. My ears tuned into the sound of Paolo’s belt buckle hitting the tiled floor of his bathroom. A buzzing sensation began to grow deep in my stomach a concoction of alcohol and excitement for what was to come.

The frost glass door moved again and Paolo’s naked figure emerged from behind it, he still held an athletic figure at an old age which could be attributed to his bike riding. My eyes traced up his hairy and well toned legs peaking at some deliciously thick thighs and keeping in line with the rest of his body hung is thick cock. I sat in awe as my cock began to grow at the magnificent sight of his body. Paolo was wearing a black cock ring that circled his shaft and balls, the ring was slightly obscured by the short curly grey hair around the base of his shaft.

Paolo began walking towards me, lubing up his hand and then running them along his shaft pulling his foreskin back and forth and circling the head of his now slightly erect cock. 

It was clear that even when he was only semi erect he was still bigger than me. His cock was breathtakingly thick and had many noticeable veins running the length of his shaft which lead to an incredible shiny purple head that angled slightly downwards. I judged his cock to be around 6 inches when fully erect which would be slightly larger than mine that as around 5.7 inches.

‘Are you sure your ready for this Angus?’

‘Yes Paolo I want you to fuck me now!’ I exclaimed loudly

he flipped me over so I was now laying doggy style at the edge of his bed. I lay my chest down on his black silk sheets and pushed my ass up into the air for him. His rough hands grabbed my ass and he slowly moved them up the sides of my body. The sensation of his lightly lubed hands running along my body and then down my stomach sent a quiver of pleasure down my spine. His hand moved off my body and I felt a cold stream of lube landing on my asshole, this cold sensation made me clench my hole at first but Paolo’s reassuring hands began to loosen and relax me. He slowly kneaded my ring to prepare it for his cock that I was so desperately waiting for.

His hands gripped the front of my thighs tightly and I began to feel the head of his cock pushing and probing my entrance, Paolo slowly began pushing the thick head of his cock into my hole and slowly but surely he entered my ass and was now securely anchored inside me my walls squeezed his head and as I contracted I felt a sting of pain in my asshole as his shaft twitched as it waited to enter.

‘Here we go’ Paolo said to me as he began pushing more and more of himself into me and after what seemed like a minute of slow advancing he stopped.

‘Angus push against my cock pretend you're trying to push it out and it will help’

I heeded his advice and to my surprise he quickly slid up to half his shaft inside me, this quick advance made me wince and took the wind out of me but Paolo immediately pulled his cock out to just the head,he waited a second before quickly pounded it back into me I let out a low grunt as he continually pulled back out and rammed into me, his pace increased as he continued his assault. The pain I was feeling turned to pleasure as I began to hear Paolo moans behind me.

After two minutes of his strokes increasing, without warning he pulled his cock back and rammed back into me, stretching my hole to its limits and plunging himself deep inside by bowels. I moaned loudly as I could feel his whole cock inside me and his hairy bush brushing against my asshole. His balls slapped against mine as he held his entire cock inside me, Paolo then began pounding me by pulling out and plunging the entire length of his cock into me, this combination of sensations brought me to the edge of cumming, the head of my cock began to throb and pulse and as if Paolo read my mind he reached around and placed a hand around my cock he jerked in tandem with the strokes of his cock plunging deep into my hole. After only 30 seconds I felt a churning in my balls, my cock twitched violently as I erupted into Paolo's waiting hand. he let the rest of my cum drip out of me and on to his bed. He lathered the cum in his hand on to his throbbing cock for some added lubrication. After 3 more minutes of fucking my ass raw his breathing began to quicken,he began to grunt and his strokes became shorter and faster.

‘My god i’m about to cum!’ he shouted in a gruff voice.

I felt his entire cock slip out of me leaving my hole gaping and allowing the lube to trickle down my balls giving me another wave of pleasure. Paolo moaned loudly as I felt his thick hot cum spray my ass and up my back. Paolo handed me some tissues to clean myself and as collected his cum and sucked it of my fingers he gave me a wry smile.

‘Angus if you want more I can introduce you to a whole new world but this is only if you are willing to submit to some one and truly accept who you may become.’ he said still panting from his orgasm.

I removed my fingers from my mouth and looked Paolo straight in the eyes.‘Paolo I want this, I want to please you again’

‘I knew you would be hooked, meet me at the bank tomorrow and we’ll  discuss it more over lunch’

I lay back down on the bed and watched Paolo clean the lube and cum that still dripped from his now shrinking cock. I pondered about this whole new world and what exactly it would entail. I felt that I was ready for more as I craved for more cock.

If only I knew how Paolo would change my life

Author note:
Hey this is my first story and I wrote it pretty quickly. Please leave as much feedback as possible so I can improve and let me know if you guys would like more because I have some more ideas for this story

This story was taken from one these sites, check them out to find more sex stories: won $14,000 <a href=<a href=&ifm=off&sub_res=yes&url_subed=

Pub: 07 Mar 2024 11:01 UTC
Views: 288