The other night a ridiculously successful silver-haired daddy contacted me. He listed his credentials, owner of several companies, a house in Mexico, even sent a pic. He was hot, suit and tie type of guy, with an obvious personal trainer. He made it very clear what he wanted from me, an erotic massage, and he would pay me triple my regular rate. How could I refuse? Intrigued I set up an appointment. After massaging a series of the boring, the fat and the ugly, I was impressed at his power and confidence.
The day of the massage, I was contacted by his Executive Assistant, she said a car would pick me up at 4pm sharp and no need to bring anything but myself. A little exposed without the comfort of my massage table and kit, I wondered what I was in store for. Was this for real? A driver knocked on my door at 4pm, and off we drove on a winding drive through downtown Toronto. We pulled up to a huge building, where we proceeded to drive through a series of secure parking below. The driver gave me a card that had the entrance details and apartment number, the penthouse.
I turn the knob and walk into a stunning condo, floor-to-ceiling windows that highlight the Toronto city skyline. Jazz is playing through BOSE speakers; a massage table is fully set-up in the middle of the main room. A sexy built man in his early-sixties sits smoking a cigar, naked with legs open, proud of his strong member.
“Take off your clothes.”
Turned on and surprised by his command of the situation, I begin to unbutton my shirt. He continues to sit, his unwavering gaze watching my striptease all the way down to my briefs. He sips a drink, looks like scotch neat, gazing at the bulge of my cock through the fabric. It pops out as I pull my briefs down.
“You have a pretty penis.”
He puts down his drink and walks over to the massage table, casually stroking his cock. I realize now that the table is at least a foot lower than how I normally massage and a worry about my back popped into my head. He lay on his back, one hand stroking his cock, the other behind his head. His abs clench as he tilts his head to look at me. I feel my throat dry and words disappearing before they reach my lips. “Massage me with that pretty penis of yours, no hands.” I walked towards him and realized the table was just below the tip of my dick. I walked towards his feet, my dick tickled his toes. I mounted the massage table as if it was my motorcycle, I grazed his shin, the hairs on his leg tickling my member. I bent forward to reach his groin with my mouth, his hand paused on his cock long enough to push my face away. “No hands, no mouth, only that, bring your pretty penis up to me.”
I walked up his body, my dick bouncing along his muscles, when I reached his dick, he took mine in his other hand and squeezed it. I gasped and clenched my butt. I dragged my burning cock up his abs, a trail of pre-cum snaked it’s way up his chest. He took some massage oil and poured it on my cock, dripping down to my ass and pooling on his chest. I realized it was flavored and smelled of caramel. He grabbed ahold of my hips, pulling me towards his mouth. His strong jaw opened, he started to lick my penis like a fucking ice cream cone. His tongue trailed down my shaft then followed the line all the way to my ass. He rubbed my ass with his oily hand, his lips never leaving my cock. His finger prodded my hole, gently and slowly entering me as his skilled tongue played a song on my cock. I shuddered as I felt waves of pleasure ripple through my body, whenever I felt that I was about to burst, he’d change direction and speed keeping me right at the edge. I felt my ass continue to open, him snaking his thick fingers through the ridges, expertly seeking out my g spot. He pulled my hard cock to the side, squeezing it tight as he started to suck my balls. From then on, the rest of the night is a blur. I think I went to a different dimension. The mix of pleasure and pain of straddling this great man, it took all my focus to simply still stand. Sensing my agony and pleasure, he stuck his fingers all the way up my ass, hooking them at the end and dragged them within me in a rhythmic motion that mirrored the deep throating of my cock. From the attention on my cock, balls, and ass all at once, I opened my lips, trying to breathe. Finding my switch, he turned on waves of orgasms, I moaned, completely uninhibited, totally in the moment. I came and came and came, my cum spurting out of his mouth, some running down his chin and throat, his scotch and caramel-flavored mouth greedily sucking me dry. He slowly took his fingers out of my ass, and when I finished he spit out my remaining cum. He pushed me off of him and I hobbled off the table, my legs sore, what just happened? He turned onto his belly, a big content grin on his face. He closed his eyes.
“I’m ready for my massage”.