The List

Ollie's eyes burned with lust. "Just relax," Goosebumps spread across Steven's thighs as Ollie kept massaging his honeypot. Steven arched his back, his legs spreading even wider. Steven braced himself for what was about to happen, he could still back out, but he didn't want to, he was far too gone. It was like an itch he NEEDED to scratch. Steven tried to hump myself against the finger, but Ollie kept his finger right on his hole, teasing him before piercing his cherry.

"Steven don't clinch or tighten up. Just try to breathe and relax your sphincter muscles," Ollie ordered as he kept circling his tight ring.

"Uh-huh," Steven panted. He had never been this aroused in his entire life, he felt as if his skin was on fire. Not even when he screwed his wife for the first time had he been this hard.

"Have you ever had anything up ass, Steven?"

"Ohmigod!" Steven exclaimed as he writhed on the table. Ollie was teasing him; he was making him wait and it was utterly frustrating. He needed something up his ass, now! "No, I-I've never done anything like this."

"Oh my...so you are a first timer, huh?" smirked Ollie, Steven saw a glint in his eyes the moment before he pressed his index finger against his little wrinkled hole.

Steven chuckled nervously; he was at Ollie's mercy.

"Relax," Ollie said softly.

Steven let out a surprised gasp as Ollie's middle finger slowly began to slide in, breaking the seal on his asshole. Regardless of what Ollie said, his natural instinct was to clench his ass on Ollie's finger, but he was already in, slowly but surely, he made his way inside. The oil making his finger glide in so smoothly, no resistance at all thanks to the specially blended substance.

"Such a tight fucking asshole,"

"There we go," crooned Ollie with a wicked smile as his finger slid all the way in. "Just breathe, Steven. The hard part is over. Now comes the fun part."

Steven almost melted on the spot, feeling his finger slowly come...inside him. He'd never experienced this before; it fell like an incredible whooshing sensation that spread out all over his body. Ollie moved his finger in and out, opening up Steven's ass, relishing the sensations of his tight anal walls around his finger. After a few seconds, Ollie curved his finger up lightly, looking for Steven's little button.

"Oh my god!" Steven gasped as jolt of electricity went up his cock.

"There it is!... I'll teach you not to be a fucking homophobe."

"Does it feel good, Steven?" His question was rhetorical. Ollie knew it felt good, but he had to maintain his professional demeanor (or at least attempt to), but he knew that by the time he was done. Steven would probably never fuck his wife ever again.

"Yes...oh my god! It feels different." Steven could feel his erection get even harder. Ollie pressed his thumb against Steven's perineum, lightly massaging it in sync with prostate massage.

"Fuck," Steven groaned "Ollie wait, I think...I think I'm gonna piss." Steven said as his hips squirmed a little.

"It's okay, Steven that is a completely normal feeling."

"You sure?" he hissed "Ollie, it really feels like I have to piss!"

Ollie smiled. "Of course, I am. You are not the first prostate massage I've given. A prostatic massage is thought to help clear the prostatic duct. This duct runs between your prostate, your reproductive and urinary system. The massage produces a spontaneous release of seminal fluid. The feeling like you have to urinate is completely normal."

Steven's cock was like a rail spike. Ollie's lust was growing as he watched in fascination as pre-cum came out of him; Like Steven, his breathing was also shallow. Ollie inhaled deeply the aroma of sex permeating the air. The musky scent emanating from the THC oil mixed with Steven's aroused state. It had a direct aphrodisiacal effect on Ollie, like smelling poppers.

Ollie continued to slowly move his finger in and out, massaging Steven's tight anal walls. "Oh, dear lord!" Steven shuddered, his legs straightening out and his hands gripping the table. It was impossible for him to keep his ass from moving. His back arched and he began to push back against Ollie's finger.

Ollie suppressed a smirk, all that macho talk, all for nothing. "You are doing great, Steven. Your tight ass is really opening up. Don't worry, sir. I'll make sure to get every last drop of...tension out of you." Ollie said, breaking character a little, but Steven was so focused on trying not moan that he didn't really pick up what Ollie said.

Ollie shifted his finger; pressing on his prostate and began massaging it in a circular motion. He made a ring with his thumb and index finger and while Ollie worked on milking his prostate, he began stroking his shaft with the ring of his fingers. The sight and the sensation was too much for him, Steven moaned loudly, he was drenched in sweat and oil, letting his desires get the best of him. His wife and daughters were nothing more than a distant memory.

"Oh my god Ollie! Don't stop!" Steven couldn't deny himself any longer. He was shamelessly pushing his ass back against Ollie's finger. He didn't even care about the consequences; his asshole was feeling the best it'd ever felt. In that moment he hoped Ollie's massage would give him the exquisite release he yearned, the release his wife had denied him for months.

A new type of pleasure -- coursed through his entire body, slowly consuming him. A warmth spread through his pelvis, slowly working its way to the tip of his cock. Like jolts of electricity going up his shaft, his body was on fire.

"Holy shit! Oh my god! Don't fucking stop Ollie! Finger my ass!" The married man whorishly moaned.

"Do you like my finger up your ass, Steven?"

"Fuck yessssss!"

Ollie loved the way Steven's anxiety and trepidations had melted away. This was the part Ollie enjoyed the most. The way Steven's abdominal muscles began to tighten, the heavy breathing, his skin glistened with oil and sweat. Ollie could see in the reflection of one of the mirrors, the way Steven's legs straightened out ad hovered over the table, the way his toes curled, his knuckles were white from desperately gripping and clawing the table.

His cum was boiling and his wife was just three doors down, none the wiser.

"It shouldn't take long now," Ollie thought. He knew Steven might try to fight the sensation, but there was no denying the fact that he was about to cum in front of another man for the first time. Even if he did try to fight the urge to cum, that battle was already lost.

Ollie wrapped his entire hand around Steven's slick shaft and began to pump in sync with the finger up his ass, it was impossible to not be hypnotized by his humongous cock, shining with oil, on top of a pair of ginormous, glistening balls. Steven gritted his teeth. For a brief moment, the images of his wife and daughters flashed into his mind. Was he betraying them? Was he gay now? This was all to get rid of the tension in his lower back, right? But these thoughts quickly faded to the back of his mind. Perhaps Steven's little voice inside his mind was right, Susan didn't have to know, as far as she was concerned, he was only getting a nice massage.

He fucking needed this, he had earned it, all of that stress, problems, work, wife, kids and pent-up desires were about to come out through his cock.

Ollie was now massaging his prostate with full pressure, pushing and caressing it in a counterclockwise motion. "Your balls have tightened. I know you're close. I can feel your prostate beginning to firm up. Don't hold anything back, Steven. Let go completely."

"Holy shit!" he writhed on the table, tightly gripping the sides.

"Are you going to cum, Steven?"

"Y-Yeah" panted Steven.

"Tell me." said Ollie, pumping faster.

Steven hissed loudly. "Fuck yes!" he panted, "Oh my god! I'm going to cum through my ass! Holy Shit! I'm going to cum so fucking hard!"

"I want you to spray all that cum for me." The ruse was up, Ollie knew Steven's life was about to change forever. "Cum for me, Steven. Forget about your fucking wife. She's not here, she will never know. I'm going to make you cum harder than any woman ever has."

"Oh yeah Ollie, don't stop. That feels fucking amazing!" moaned Steven as he thrusted into his hands.

Ollie could feel his cock getting harder and thicker in his hand, he saw the illusion of heterosexuality vanishing from Steven as his body betrayed him, quickly getting to the point of no return.

"Fucking cum for me, Steven. Do you like getting milked, hmm?" asked Ollie goading him. "I knew I was going to stick my finger up your ass the moment I saw you."

"Ollie!" Steven moaned, his body began to tense up like a violin string.

"Give me everything you got!" Ollie said with a salacious smile. "I'll milk every last drop out of you just like others!"

Steven's hands white-knuckled as he gripped the table. "Holy shit! I'm gonna cum! I'm gonna cum! I'm gonna cum!" he rattled off the words quickly through gritted teeth. Steven felt his cock grow harder than ever before from a pressure he didn't know where it came from. His eyes rolled back and his back arched hard as an enormous rope of semen shot from the tip of his cock.

"FUCK!" Steven roared as his cock flexed in Ollies hand. His hot asshole clamped down on Ollie's finger who pumped his shaft as rope after rope of thick cream spurted from him. "Keep going! Shit! Oh my god don't stop! Don't you dare fucking stop until I tell you!" Steven was like a man possessed.

Rope after rope of his cream landed on Steven's stomach. "Fuck yeah! That's it, cum for me Mr. Winslow!" Ollie smiled devilishly. "Let it all out. Give me your daddy cream."

He writhed and moaned loudly on the table. Steven's toes curled deliciously, and his legs straightened out, his feet digging into the table. Ollie's hand was covered in thick strings of white cum, his pumping movement never ceasing until Steven said otherwise.

"Yes! Fuck yes! Just like that! Keep going!" Steven groaned and growled like a bull as Ollie milked everything out if him, his legs trembled as every nerve cascaded in ecstasy. Only the sounds of heavy breathing and Ollie's hands pumping his slick, cum coated anaconda could be heard.

"He'll probably never fuck his wife again."

Steven shot at least six ropes of his pent-up heterosexuality; his cock continued to throb in Ollie's hand. "Oh my fucking god!" he shuddered. Steven's sexual ecstasy began to taper off. His clenched butt relaxed back into the table. Ollie continued to gently stroke his dick for several more minutes until he ordered otherwise.

"Goddamn," Steven said, catching his breath "Holy shit...you may stop Ollie."

Ollie gradually slowed down his stroking movement until his hand came to a complete stop. He slowly slid his finger from Steven's deflowered asshole. Steven was quiet for a minutes, his powerful chest heaved as he recovered from his climax, processing everything that just happened, he had actually went through with it. Steven thought the guilt would be horrible for convincing himself into getting his prostate milked once post-nut clarity kicked in, but the reality was, he had never felt such big satisfaction in his life, he had no regrets and was already contemplating booking another session.

"How was that for your first massage, Steven?" Ollie broke the silence.

"Wow...just...wow. I really fucking needed that." he chuckled.

"You certainly did," Ollie said with a wry smile "You really fucking needed that." Ollie's hand was coated completely. He opened his fingers, strings of thick, pearly white cum stretching between his fingers. The smell of Steven's pure manly essence was so strong it made Ollie salivate.

"Just give me a minute," Steven breathed, savoring the warm post-nut bliss as he stared at the ceiling again.

"You can have all the time you want," Ollie giggled. "Do you feel better now?"

"Oh yeah" he sighed. "I feel fantastic, that was really intense. I never realized how sore my back and legs really were."

"A prostate massage is a very powerful and...eye opening experience for a first timer and from the looks of it, it had been quite a while for you, hasn't it?"

"Oh, you have no idea," Steven chuckled.

Steven locked eyes with Ollie and stared as Ollie scooped a large dollop of his daddy cream with his tongue. Savoring its illicit, salty taste. Ollie's eyes never left Steven's. "Mmmm, you taste delicious Mr. Winslow." He said with a wicked smile. "Like I said Steven, it's not healthy for a man to hold it in for so long."

Steven gulped. "Ollie, do you always do this?"

Ollie grinned at him. "Oh no, not at all. This isn't a brothel and I'm not a prostitute. Let's just say this is a very exclusive massage that only I offer to a very, very select few."

"To whom?" asked Steven.

"I'm very sorry, Steven but that is confidential. Only I know their names, I'm sure you understand. But I believe you know one of them. I've seen you play golf with him."

Steven couldn't help but wonder who it could be. He only played golf with a handful of guys. They were all married and had children as well.

"Steven?" Ollie said snapping him from his thoughts "Just like you asked me to keep this between us. I would also like to ask to keep this to yourself."

"Of, course."

"Great," Ollie smiled.

"Just stay right there, I'll clean you up." Ollie untangled himself from Steven's leg lock. Ollie cleaned the evidence of their wicked massage, particularly focusing on his softened cock. Even soft it still looked huge.

Steven had never felt so relaxed in life; his body felt so light after such a strong orgasm. He couldn't even feel his legs.

Ollie placed a fresh robe on the table for him to change. "I'm very happy you enjoyed your very first massage, Steven. I hope to see you again very soon." he smiled, his professional tone back.

"Yeah, I think... I'll definitely be back." replied Steven.

And after a very generous tip Ollie was gone, leaving Steven to change into the robe and make his way to the next part of his spa experience. As he made his way back it just so happened his wife was also coming out of her room.

"Ollie hi!" she hugged him. "Oh my god are you guys done?" Susan asked expectantly.

"We just finished," he smiled.

"Oh my god! Tell me everything! How was it?"

"He was a little grumpy at the beginning, it was to be expected of course but I managed to get all the tension out of him. You could say he's completely...drained."

"Oh, that's so good to hear!" sighed Susan not picking up the innuendo "I was afraid Steven would be rude or say something mean to you. Hopefully he starts coming here more often."

"Oh, don't worry Ms. Winslow. I'll make sure your husband cums regularly now."

"Absolutely!" he smiled deviously "After today, I think he'll definitely start cumming more frequently."

Steven Winslow, 42 years old, became the 10^th name on Ollie's list.

The List:

• James McCoy (CEO, SVTECH Co.), 46 years old. Married, one son, one daughter.
• Alexander Grant (CEO Rothwynn Group), 44 years old. Married, three sons.
• William Donovan (CEO Blackwood Co), 47 years old. Married, two daughters.
• Joseph Erickson (Senator, Maryland), 51 years old. Married, two daughters, one son.
• Daniel Callahan (Owner of North Carolina Vipers), 59 years old. Married, two sons.
• Robert Allen Clarke (President and CEO of Boeing Company), 48 years old. Married four daughters.
• Christopher Muller (Chairman and Chief Executive Officer of Pfizer), 49 years old. Married. One son. Pregnant wife.
• Richard Caldwell (Pastor) 45 years old. Married. One son. Two daughters.
• Mike Van Riken (Senator, Georgia), 49 years old. Married. Twin daughters.
• Steven Winslow (President of Kessler Bank), 42 years old. Married. two daughters.

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Hello people, Illogical speaking.

As always, many thanks for reading my story. As always do let me know in the comments, your thoughts, suggestions, criticisms and/or feedback.

Like I said at the beginning, it's just a story, so try not to cry in the comments...but if you do feel like crying, you know where the comment section is >:)

Many thanks to Twins56 and blamed_4_bridgburning for editing my story.

Until next time,

Illogical.