Chasing Destiny – Toby’s Discovery

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This is my second stab at writing a gay male story. My hope is that you get enjoyment from reading this, and my wish is that you leave me a comment, along with giving me a vote. This story is fiction, as are all the characters involved. Any similarity of the characters to real people is simply coincidental. Also, all characters are at least 18 years old.

And now, on to the story…


The door to the school councilors office swung inward and a pretty, platinum blonde teenage girl giggled as she stepped out into the waiting area where Toby McDaniels sat waiting for his turn to see the councilor. Behind the girl stood Mr. Gerald Post, the high school guidance councilor with a smile on his face. He stood at least a foot taller than the girl, and her petite size was dwarfed by the muscular body of the councilor.

“I’ll remember that one,” Mr. Post said with a friendly laugh.

“Yeah, I’ll bet you will,” the blonde girl said laughing back.

“Alright, I’ll see you next week Kim.”

“Bye Mr. Post,” the blonde said with a flirty wave and a wink. She tossed her long hair with a flip of her head and headed toward the exit.

Mr. Post watched the girl as she walked across the room to the door, his eyes seeming to linger on her swaying ass, before he turned toward Toby and said, “Come on in Toby.”

Toby waited until the girl had left and shut the door, then he stood up and followed Mr. Post into his office. As the heavy wooden door shut, he reached back and locked it, then readjusted the mini blind covering the bullet proof glass over the window.

“Did you fuck her?” Toby asked when he finally turned around to look at Gerald, who had retreated behind his large desk.

“Now why would you ask a thing like that Toby? Do you think I fuck all the students I deal with?”

“Not all of them, only the pretty ones who dress and act like a slut.” Toby was now slowly walking across Mr. Post’s office toward the wooden desk.

Gerald sighed deeply, then shook his head and said, “No Toby, I didn’t fuck her. Why don’t you come over here and check my cock for signs of pussy juices.”

“You may have washed up already,” Toby said. He was now standing in front of Mr. Post’s desk, staring accusingly at the much larger man.

Gerald scoffed at the idea, then said, “Toby, I promise you that I didn’t fuck her. Why would you think something like that anyway?”

“Because I saw the way you stared at her ass when she walked out. Tell the truth, you like her ass, don’t you?”

Mr. Post thought for a moment before answering. He knew better than to lie, Toby was far too smart to sneak anything past him. “Well… I guess I do Toby. She’s a very pretty girl, and I did tell you more than once that I’m bisexual. You can’t fault me for looking at the sexy ass of an eighteen year old girl.”

“So, do you want to fuck her?”

“I wouldn’t be human if I didn’t want to fuck something so god damn sexy,” Gerald said, “but I’m not going to push my luck any more than I already have. I don’t want to go to prison.”

“But you fuck me,” Toby said, “you could go to prison for that.”

“Well technically I don’t fuck you Toby. We pleasure each other orally, and while that is a punishable offense, I’m more comfortable doing it with you because I trust that you won’t tell.”

“But you didn’t know that the first time.”

“Yes Toby, I took a chance, and I’m glad I did. You approached me remember? I didn’t come on to you.”

Actually, Toby had been seeing Mr. Post because he was conflicted about coming out to his dad. Toby’s father was a conservative Christian who denounced all homosexual activity, so Toby was scared to come out to him. One day while Toby was talking about his fears, Gerald confessed that he had gone through the same fears when he was in high school.

Two months earlier-

“But, you’re not gay, you’re married,” Toby had said in response to Mr. Post’s admission.

“Yes Toby, I am married, but I’m not entirely straight either. I’m bisexual, and coming to terms with that fact was very difficult for me.”

“So…you like guys and girls?”

“Yes, but I will ask you to please keep that to yourself. It’s not exactly common knowledge around school and, well, frankly it’s nobody’s business.”

Now Toby was intrigued and he wanted to know more. For an old guy, Mr. Post certainly kept himself in tip top shape, and Toby did have a thing for men with muscles. All of a sudden, he was very interested in hearing some details. “Have you been with guys?”

Gerald cleared his throat before answering, “That’s a bit personal.”

“But, I’ve never been with a guy, or a girl for that matter. I just know that I’m not interested in being with a girl. You’ve been with your wife, but if you’ve never been with a man, how do you know that you’re bisexual?”

“Okay Toby, because of your situation, I’ll answer your question on one condition. You have to promise me that you’ll never talk of this outside these four walls.”

“I gaziantep escort promise,” Toby quickly replied, sitting higher up in his seat.

“Okay, the truth is…yes, I’ve been with a few men before, and I’ve enjoyed myself. My wife does know that I’m bisexual, and she’s okay with it because she’s bisexual also.”

“Wow,” Toby exclaimed.

“Yes…wow,” Gerald repeated. “Now, we should get back on tr-.”

“What’s it like? Being with a man, I mean.” Toby interrupted.

“Perhaps you’ll find out one day, but now-“

“Will you show me? I mean like, will you…teach me how to please a man?”

“That would be highly unethical Toby, not to mention that it could get me thrown in prison. I’m afraid you’ll have to find out on you own.”

“I won’t ever tell a soul Mr. Post, I swear on my grandmothers grave. Just give me some pointers so I’ll know what to do…please.”

Another heavy sigh, followed by tapping on his desk with his pointer and ring finger, something that Gerald often did while he was thinking. Finally he said, “You just do what feels good to you Toby. The same thing that feels good to you when you masturbate will feel good to another man.”

“But what if I don’t masturbate?”

“I highly doubt that Toby. In fact I’d wager my life savings that all young men your age masturbate.”

Toby’s eyes lowered to the floor before he spoke. “Well, I tried one time. I heard some guys talking about ‘jerking off’ and they were making the motions, you know…” Toby simulated stroking his cock in the air until Gerald nodded. “So I tried later that night in bed. I was laying on the sheets naked because it was hot, and I started to stroke myself, and after like a minute it felt really good.”

Gerald wouldn’t admit it, but he was sporting a large boner at that moment listening to Toby talk about masturbation. “So what happened?” he asked, trying his best to sound clinical.

“My mom walked in with my laundry.”

“Ouch!” Gerald winced at the visual of being caught masturbating by your mother.

“Yeah, it was the most embarrassed I’ve ever been in my life.”

“What did she do?”

“She freaked out. Threw the basket of laundry at me and started bitching. The thing is, when she walked in, it jumped me so much, that I started…you know.”


“Yeah. It was my first real one and this glob of white gunk spurted up in the air just as she threw the laundry basket at me. All my clean clothes hit me square on, and I used them to cover me while my dick kept spurting all over the place. I was so shocked and…and…”

“Flustered,” Gerald offered.

“Yeah that… and she looked like she was going to have a heart attack right there. And then my dad came in, and I wanted to die.”

“Oh, that must have been bad.”

“I was grounded for a month, but worse than that was Dad took my bedroom door off the hinges. Said that if I didn’t have any privacy, I wouldn’t be able to defile myself anymore.”

“He actually used the word defile?”

“Yes sir,” Toby said, “He said that it was a sin and that “God wouldn’t approve.””

“Huh, well I’m sorry that you had to go through that embarrassment Toby,” Gerald said, “And I’m sorry that your father and mother are so strict, but you’re an adult now, school will be over in a few months and you’ll be going off to college and meeting new people and having new experiences. And you’ll make your own decisions about what is right and wrong with regards to your body.”

“I haven’t had another orgasm since that one that my mom walked in on,” Toby said, “My dick is hard all the time. Do you know how embarrassing it is to walk around the halls out there like this?” He stood up and pointed at the obvious lump in his shorts.

Gerald swallowed and licked his lips as he looked at the outline of what appeared to be a good sized cock. He cleared his throat again and forced his eyes down as his own erection threatened to burst forth from his pants. “Yeah, well I’m sorry to hear that also Toby, but ah, we shouldn’t be discussing this you know.”

“Do you think I’m ugly?”

Once more, the councilor was taken aback by the line of questioning coming from the student. “Of course not Toby, you’re a fine looking young man,” he said, increasingly aware of the student’s muscular physique and ruggedly good looks. Until now, he had never noticed how good Toby looked, but all of a sudden, he wanted him.

“Would you give me some pointers? Tell me some techniques that I could use if I’m ever with a man?”

“It wouldn’t be right Toby,” Gerald said, but his resistance was weakening.

“Please Mr. Post.”

Another loud sigh came from the guidance councilor, then he slowly nodded. “Okay, I’ll give you a few tips.”

“Awesome,” Toby said, perking right up. “so, what should I do?”

Gerald knew that he was treading on thin ice, but his sudden desire won out and he said, “Well Toby, if you are serious about learning from me, you need to prove it by coming over here and getting on your knees.”

“Okay,” Toby agreed. He was nervous but his excitement was too high to stop, so he made his way around the back of Mr. Post’s desk. Once there, he lowered himself to his knees and waited.

“I’ll ask you one last time Toby, are you sure you want this?”

“Yes sir.”

“Then undo my pants and pull my cock out.”

That day, Toby learned how to handle a cock that wasn’t his own. He learned how to tease a man, and how to prolong the anticipation, which would make the actual act more intense. Mr. Post showed him where all the usual most sensitive spots were and how to maximize pleasure from them. Toby stroked, sniffed, licked and sucked the councilor, gaining more and more confidence as Mr. Post complimented his new found talent and became more and more agitated as he got closer to orgasm.

Just before he came, Mr. Post warned Toby, “I’m going to cum very soon Toby, and I want you to experience what it’s like to have a cock cum inside your mouth. You can swallow my load if you want, or spit it out in the trash can afterward, but don’t stop sucking until I tell you, okay?”

“Mm-hm,” Toby agreed, his mouth filled with cock. A few moments later, Mr. Post gripped the top of his head and moaned loudly as his orgasm erupted. As the hot sperm squirted from the piss hole of Mr. Post’s cock, Toby’s own orgasm let loose in his pants, and he swallowed the very first of many creamy loads.

Back to Present day –

Mr. Post stood up from behind his desk and asked, “Are you going to tell me what has gotten into you Toby? You already know that I’m not exclusive with you, so even if I was fucking Tracy Myers – which I’m not – why would you be upset with that?”

Toby sighed, then dropped down into the seat. “I think my dad is having an affair,” he said sullenly.

Mr. Post’s head tilted to the side and his left eyebrow raised up. “And what makes you think that?” he asked.

“Well, he’s always leaving the house at odd times, telling my mother that his boss needs him to fix something, or that his brother wants help with something, or that he’s going to the store for something. My mom always believes him, but I don’t. He’s been acting strange lately, like he’s hiding something, and I’ve seen him come home late and rush right into the bathroom and shower, even if he showered earlier.”

“I see,” Mr. Post said. “You do realize that there could be perfectly good explanations for everything your father is doing? Without proof that he’s cheating, it’s all just speculation.”

“Yeah, I know. I was thinking that now that I have a car, I should follow him one of these times. Maybe I’ll catch him in the act.”

“Well, you could do that of course, but have you thought about what you would do if it was true?”

“No. I’d probably take pictures with my cell phone and show mom. She deserves to know. He’s such an intolerant prick, and to think that he might be fucking around on mom just makes me want to punch something.” Toby lowered his eyes to the floor then said, “I told him that I was gay.”

Mr. Post’s eyebrows came up. “How did he take it?” he asked.

“He gave me until this weekend to get out. He said, “no gay boy is going to live under my roof.” He wanted to throw me out that night, but mom stopped him. He’s such a prick.”

Mr. Post dropped back into his chair and sighed loudly. “Wow,” he said.

“Yeah, wow,” Toby mumbled. “but if I catch him in the act of fucking another woman, I’ll have him by the balls.”

“Yes I suppose you would,” Mr. Post responded.

After a few moments of silence, Toby said, “Um, I’m sorry that I accused you of fucking Tracy Myers Mr. Post. I guess I was just pissed off at my father and took it out on you.”

“It’s quite alright Toby, I understand completely, and if you’d like to skip our normal activities today, I’ll understand that also.”

Toby shook his head. “Now why would I want to skip our normal activities? It is your turn to suck me off you know.”

Mr. Post furrowed his brow and tilted his head. “Are you sure about that? Because I’m pretty sure that it’s your turn to suck my cock.”

“Oh no, I’ve been keeping track, and…”

Mr. Post waved his hand and chuckled. “I’m kidding Toby. Actually, I’ve been looking forward to sucking your delicious cock today.” He stood up and strolled around to the front of his desk until he was standing in front of the student. “You have the best tasting cum of anyone I know. I only wish you’d let me take you home to my wife so she could get a taste.” He was on his knees now un-buttoning and unzipping Toby’s pants. “She keeps begging me to talk you into it.”

“Maybe someday,” Toby said, lifting his ass up off the chair so the good councilor could tug his pants and underwear down. His thick cock, swollen erect, sprang free and pointed straight up in the air.

“Well I’ll just have to kidnap you for a few hours,” Mr. Post said as he took Toby’s seven inch cock into his hand. “And tie you down so my wife can give you her special blowjob.” He leaned in a licked a drop of pre-cum that had rolled halfway down the crown before saying, “You may be gay, but you wouldn’t be able to resist her sucking mouth.” And with that he engulfed the first three inches of Toby’s cock into his mouth.

“Ohhhh fuck,” Toby hissed and bit his bottom lip as he watched the older man wrap his lips around his shaft, and suck his way to the tip.

For the next twelve and a half minutes, Toby moaned as his cock was worked over from top to bottom. Mr. Post managed to keep Toby from cumming by backing off each time he got close. Each time, the teen would beg to be brought to orgasm, and the good councilor would smile, or say, “All in good time Toby.” He was merciless, and he had the teenager squirming all over the chair by the time he finally decided to end it.

When Toby was trembling all over and whining like a hurt dog, Mr. Post lifted off his cock and said, “Are you ready to cum Toby?”

“Oh God yes,” Toby blurted. His head, which had been lolling back, snapped back up, his eyes trying to focus. “Please finish me. You’re driving me crazy.”

“Very well Toby, enjoy,” Mr. Post said, then in one movement, he engulfed Toby’s prick in his hot mouth. He was only able to get about half of Toby’s shaft in his mouth, but it was what he did with his tongue that sealed the deal. Forming a seal around the shaft, Mr. Post sucked, while his thick tongue slid back and forth slowly on the sensitive underside. Meanwhile his left hand wrapped around Toby’s ball sack and gently stroked, while his tongue began to pick up speed. He wasn’t just sliding his tongue back and forth now, he was going in circles with it, the whole time still sucking and tickling his balls. This technique would prove too much for Toby.

“Ahhhh, Oh fuck, oh f-f-f-fuck, oh sh-sh-sh-shit, I’m cu- I’m cu- Ohhh I’m cumming!” Toby cried out as he felt the familiar pulses begin in his balls. Past the point of no return, nothing could stop him from spending his load. His hands came up and gripped the sides of Mr. Post’s head as he felt the first rope of creamy cum travel up his shaft and blast the back of his councilors throat.

Feeling the heated liquid squirt into his throat, Mr. Post’s throat began swallowing over and over, causing Toby’s cock to get squeezed and released multiple times and prolonging his orgasm. Mr. Post never let up on the sucking and swallowing, as if he was trying to suck Toby’s life force out his cock, until the feelings changed from intense pleasure to intense sensitivity.

“Oh stop – stop – stop, it’s too much,” Toby moaned, trying to push Mr. Post’s head away, but the good councilor had other ideas and doubled down, sucking and licking the teen’s hypersensitive glans. “Ohh fuuuck…please stop please stop oohhh fuck.” Normally after Toby came, his cock would droop to about half hard within about thirty seconds, but Mr. Post wasn’t allowing it to loose any rigidness.

A high pitched whine came from Toby as the sensation in his cock started to feel good again, and Mr. Post let the swollen head pop from his mouth with a loud smack to look up at the teen and say, “Keep your voice down or we’ll get caught.” He smiled as he saw the look on Toby’s face. It was an almost pained expression, but it was so sexy.

Mr. Post looked back down at the throbbing cock that he had been sucking on for about fifteen minutes. The head was purple and shiny wet, and the pee hole seemed to be winking at him. He lowered his mouth and stuck the tip of his tongue in the pee hole for a moment before dropping down and engulfing half the shaft. From above, he heard Toby suck in a deep breath, then felt the boy’s hands run through his hair. He also felt Toby’s hips starting to thrust up.

“Oh God,” Toby whined, “You’re gonna- you’re gonna- you’re gonna make me cum again.”

That’s just what Mr. Post planned, only this time, he wasn’t going to slow down for anything. He wanted to get Toby off as quickly as possible this time, to show the young man how much control a good blowjob artist could have over a man. He flattened his tongue and curled it around Toby’s shaft running it up and down the underside while his hand stroked the remaining couple of inches not inside his mouth. He could feel Toby’s balls tightening up under his hand, while the cock in his mouth seemed to swell even larger, stretching his jaw open wider.

Fearing that he would make too much noise, Toby folded his arm across his mouth and whimpered, clenching his teeth and breathing erratically through his nose while his balls began to work again, pumping more of his seed through his urethra and into Mr. Post’s sucking mouth. As his second orgasm in under five minutes began to wind down, the sensitivity in his cock quickly wound up. Knowing he wouldn’t be able to keep quiet through any more, Toby pushed on Mr. Post’s head again.

“STOP!” he blurted a bit louder than he had wanted, but he couldn’t take anymore. This time Mr. Post released Toby’s cock to the cool air, but continued to gently massage his balls.

“Not up for round three?” Mr. Post asked, a sly smile playing on his lips.

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