Closing The Deal Pt. 02

The new job was fast paced and hectic.

Plenty of opportunities to close deals and earn commission, made the summer job one of the best for saving towards final year college needs.

With the boss Matt out of town frequently the opportunity to spend some time in his office 'socialising' hadn't been available.

Though with his schedule due to have him in town the following week, a brief email exchange confirmed a meet up.

I just had one client to meet for the first time in the next few days, a VIP account and one that Matt had stressed I do my best to secure the updated contract terms.

The initial discussions with the client Tony, had been positive and with the finer details of the renewed deal settled, it was left for me to take the contracts to him when he was in town for him to sign and make the deal.

Tony suggested we meet at his hotel the following evening after he had settled his remaining appointments.

I agreed and confirming the time for 8pm, noted the hotel and room number.

The next day passed quickly at work and I updated Matt at the end of the day on active cases, closed deals and my evening meeting with Tony.

My phone rang shortly after.

Matt stressed again the importance of the deal with Tony and his company and told me to do whatever it takes.

Recalling my initial interview I knew exactly what Matt was suggesting and after showering at home made a point to select the right clothing to wear.

As it was still a work meeting I picked a pair of light grey slim fit pants, slim fit white short sleeved shirt and a pure white jockstrap (just in case the evening panned out as I expected).

Catching a glimpse of my tight slim ass in the mirror as I slipped on the jockstrap, I couldn't help but smile at the pert shape and the contrast of the white elastic of the jockstrap circling my waist and looping my thighs, on my pale white skin.

Arriving at the hotel I made my way to the lobby bar.

Just as I sat down I received a message from Tony. He was running late and let me know he should be there in about half an hour.

I decided to read through the documents one more time, and became engrossed in my work, until a light tap on the shoulder caught my attention.

I turned around and was greeted by Tony.

Tony was in his early sixties, with a full head of grey hair.

His tall frame was matched with an athletic build.

Tony apologised for being late, and before I could offer to order a drink, he suggested we head up to his suite as he had a few more calls to make, and he would order drinks to the room.

Given he was the client and I was still working, it was a straight forward decision.

We made our way to his suite and shortly after entered the spacious and well appointed room.

Three rooms actually. A master bedroom with ensuite, a large living room with sofas and tables, and a small office space.

Tony quickly picked up the phone and after a brief conversation ended the call.

Joining me in the living room area Tony informed me he had ordered some drinks, and that he would finish up his calls quickly, then join me to settle the documents.

I relaxed on the sofa while Tony excused himself to the office alcove.

A few minutes later the doorbell chimed and I let the room service staff in.

A chilled bottle of champagne and two glasses were placed on the table.

Soon after Tony returned to the room and apologising for the delay set about pouring a drink each.

Sitting next to me on the sofa, Tony passed me a drink and we soon slipped into casual conversation.

The drinks continued to flow as Tony proved to be both a charming and charismatic host.

I had to remind myself why I was there and took the opportunity while Tony poured another drink, to bring the documents out and place them on the table.

Tony settled into the sofa next to me, though this time noticeably closer, our thighs almost touching as he leaned forward and picked up the documents to read one final time.

Placing the documents on the table Tony smiled and said everything looked in order.

Passing Tony my pen, I asked him to sign, and deciding to take the initiative told him I had a surprise thank you in store for him.

The broad smile that greeted me as Tony signed was enough to know that he was looking forward to it.

I finished checking the documents and counter signing before asking Tony to lean back and relax.

Taking his drink in hand he did as requested as I stood in front of him, keeping eye contact as I slowly removed my shirt and pants.

Standing there in my jockstrap, my hard cock pushing against the confines of the material as Tony let out a whistle of approval.

He also undid his belt and pants, slipping out of his boxers as he removed his shirt, before settling back down on to the sofa.

His large athletic build was well proportioned and his eight inch cut cock was standing proudly.

Clearly turned on by the possibilities.

I dropped to my knees, all the while keeping eye contact as my mouth closed in on his glistening cock head.

I lowered my mouth on to Tony's cock head.

Swirling my tongue all over as I worked his shaft slowly down my throat.

The deep moan of approval was just the right encouragement as I continued working Tony's cock head with a real enthusiasm.

I was loving the feeling of Tony's cock in my mouth.

His large throbbing head, and thick shaft, filled my mouth completely.

My tongue and lips coated with my saliva as I worked him further down my throat.

Tony's continual words of encouragement as well as deep, primal moans were enough to know he was loving it just as much as I was.

After an extended period enjoyed my cock sucking abilities, Tony squeezed my forearm gently and lifting my head to look him in the eyes, my mouth still on his cock, he asked me to follow him.

We stood up and taking my hand Tony led me to the bedroom, where he guided me on to the bed putting me on all fours on the edge of the bed, as he crouched behind me.

His strong hands spreading my ass cheeks as his hot wet tongue and soft lips lightly touched my exposed ass hole.

I felt my body melt into a continuous wave of pleasure as Tony pushed his tongue into my ass. The firm strength of his hands on my ass cheeks and the wet warm attention from his tongue was driving me wild with lust.

I let Tony know just how good it felt as I grabbed the side of the mattress with my hands for support.

My firm grip highlighting just how good Tony was with his tongue and lips.

Opening me up and giving intense pleasure all at the same time.

I was lost in the pleasure of Tony's prolonged attention with his tongue.

My hole was wet and open as he continued to go from lightly teasing the outside of my hole, to driving his tongue inside me as deep as he could go, fucking me with his tongue as my body continued to respond to his attention.

Slowly Tony pulled his tongue out of my ass and after a gentle kiss of my hole, he climbed up on to the mattress, kneeling directly against my thighs, as he began rubbing his hard cock over my hole.

Again I let Tony know how good it felt as a wave of pleasure shuddered through my body.

The anticipation of what was to come was a delightful mix of nervous excitement and outright lust.

Tony applied some lube to his hard shaft as he returned his attention to my hole.

Pushing his cock up and over my ass, occasionally pausing to tease and probe my hole, before returning to rubbing his cock up my ass crack.

I was loving the attention Tony was giving my ass with his cock.

The lube adding another sensation of pleasure helping his cock probe and tease my ass as he continued the extended foreplay.

I was on fire and ready to be fucked.

Placing my hands behind me on my ass cheeks, I pulled them apart and pushing my hips back towards Tony, let him know exactly what I wanted.

Tony didn't miss a beat.

Right away I could feel the pressure of his raw cock head pushing against my hole.

I took a deep breath to relax my body as Tony shifted his weight forward, pushing his cock into my ass.

For a moment we held that position. His cock head inside me. My body adjusting to the size and presence of his cock.

The silence was broken when Tony asked me if I was ready for more.

I told him to keep going, and slowly but surely Tony worked his shaft into me.

Pushing past my resistance and filling me with his thick strong cock.

A long continual moan of delight from me filled the room as our most taboo of connections continued.

Tony asked me to move forward, slowly dropping from my knees until I was flat on the bed.

Lying on my stomach as he continued to slowly drill my ass nice and deep.

Tony lowered his body weight on top of me until he was lying on me. His mouth able to nibble on my ear and suck on my neck as he steadily fucked my hole.

Threading his arms under mine Tony took hold of my hands in his, the intimacy of the moment matching the sensual yet very erotic fucking I was receiving.

With his mouth so close to my ear Tony whispered asking me if I was enjoying the attention of his cock.

I replied with a soft purr and quietly whispered encouragement, asking him not to stop as I was loving the pleasure his cock was giving me.

We slipped into a comfortable semi silence.

The only sounds were grunts and moans of pleasure in unison with the rhythmic slapping of skin as our bodies met in contact.

Tony's breathing was now noticeably faster.

His grip on my hands tightening as his body also became more tense on top of me.

Tony let me know he was about to cum, and before I could reply I felt Tony lift his weight off me, pulling his rigid shaft out of my hungry ass as he did so.

Immediately my ass was greeted with the coolness of the air conditioned room before moments later the first hot spurt of cum hit the top of my ass crack.

And then another.

And more again.

Unloading his hot cum on my ass as it slowly leaked down and over my exposed and well used hole.

Tony collapsed on the bed next to me. Draping his arm around my shoulders and pulling me towards him, our lips met in a slow passionate kiss.

His tongue eagerly exploring my mouth, wrapping itself around my tongue as our lips melted into each others.

I was now lying on my side, facing him, my leg spread over his hip as his hand searched for my cock.

We continued to kiss as Tony started stroking me, working my foreskin back before pushing up with firm strong strokes.

I purred in appreciation at the pleasure I was receiving as Tony broke off our kiss, moving his mouth down to my sensitive nipples and giving them a delightful teasing before he moved back towards my neck.

Where he proceeded to suck on my neck.

Lightly at first, though soon with more suction and a lot more pressure.

The feeling of having my cock firmly stroked and receiving a sensual love bite at the same time pushed me over the edge.

Moaning loudly as I started to shoot my load over Tony's hand and on to his flat stomach.

Tony continued to milk every last drop out of me until I was spent.

I took a moment to catch my breath as the intensity of the orgasm swept through my body.

My ass coated in Tony's load, my load covering Tony and myself.

Tony was the first to break the silence.

Propping himself up next to me, he took his cum covered fingers and slowly licked my cum off his thumb, all the while holding eye contact with me.

He moved his hand towards my mouth, and without missing a beat I opened my lips and licked my cum off his finger, before our tongues danced again.

Sharing my cum between us as we continued to make out.

Eventually we stopped kissing, and I made my way to the bathroom to freshen up before dressing and collecting my work documents.

Tony, wrapped in a towel his chiseled chest on display leaned in to give me a goodbye kiss.

Just as I was about to depart Tony let me know he would be in town in a few more weeks, and asked if I would like to meet again.

Smiling at him as I headed out the door, I let him know that I would be expecting a few rounds next time.

The wink and big grin from him enough to know that there would be more next time round.