Black Ridge Secrets: Jack Holliday

Now that it was the weekend Jack Holliday was going to make good on his word to Tommy and take him to see the local proctologist. After hearing that his son had been sexual with the town slut, Kevin Cummings, he wanted to make sure that Tommy’s purity was still intact. Jack was driving through town with his son sitting next to him, looking a bit nervous. “You ok, Tommy?” He asked the boy, keeping his eyes on the road.

“Yeah, it’s just… this is my first visit to a proctologist…” Tommy trailed-off in response.

“Don’t worry; I trust you, son. We’re just gonna’ make sure everything is completely fine.” Jack reassured his boy, reaching a hand over and patting his thigh. 

“Thanks, Daddy.” Tommy replied, placing his hand over his parent’s for a moment. 

“Here we are.” Jack declared as he pulled-up in front of the Doctor’s office. Moments later they were inside and meeting with the town’s proctologist; Dr. Patrick Ross.

The Doctor was a handsome, middle-aged Alpha with dark brown hair and a mustache.

“Hey there, great to meet you.” Dr. Ross said, shaking Jack's hand. “I’ve heard great things about you, Mr. Holliday. And this must be young Tommy.” He added, grinning at the statuesque man and then down at his son.

“Thank you.” Jack chuckled, beaming proudly.

“Hi.” Tommy responded with a timid smile.

“Come right on in and let’s get started.” Dr. Ross welcomed them into the examination room. “Alright Tommy, you’re gonna’ get nude below the waist and hop on here.” He announced, patting the observation table.

Tommy knew that this was supposed to happen but still looked up at his Dad nervously.

Jack merely nodded at his son.

Tommy turned around and slowly lowered his pants. He could feel the Alpha mens’ gaze on him as he stripped himself below the waist.

Dr. Ross’ eyes widened in appreciation when the young man’s pale, perfectly-shaped buttocks were revealed.

Jack looked at his boy’s beautiful bum with pride but felt uneasy with having another man look at his son’s bare body. He knew this was a completely legitimate procedure that served an important purpose, but another Alpha male looking at his son’s nudity still had him feeling a bit on-edge. He cleared his throat conspicuously.

“Alright, Tommy. Up here on the table.” Dr. Ross said again before sitting in his chair. “Your rear-end facing me and your Dad.” He instructed the boy.

Tommy kept his back turned to the older men so that the Doctor wouldn’t get a frontal look at his penis and got on top of the sturdy, low-level table on all fours.

“You’re going to arch your back, with your head lowered and your behind in the air.” Dr. Ross continued his direction of his patient.

Jack stood behind the Doctor and felt his pulse quicken as he saw his son get into position. He had seen Tommy’s bum recently when he had spanked him, but it felt entirely different seeing his boy like this; in such a provocative position, with his buttocks parted ever-so-slightly.

Dr. Ross was wearing his casual clothes and started to feel himself get hot under the collar. In his line of work he had the privilege of inspecting many young Beta males’ asses and this boy’s bum was one of the best he had ever seen. If Tommy’s Dad wasn’t looming over his shoulder he wouldn’t have been able to restrain himself.

Tommy was blushing as he held his position, he could only imagine what the men were thinking as they looked at his nude backside.

The Doctor suppressed the urge to lick his lips lasciviously and instead looked back over his shoulder at Jack and said; “You must be very proud.”

Jack stood there with his arms folded in front of him and nodded his head. “Yes, I am.” He grunted quietly.

Dr. Ross turned back to the young man and placed his hands on the patient’s buttocks, gently parting them to get a good look at the anus. Tommy’s virgin bussy was just as tantalizing as his firm buttocks were and the Doctor grinned at the sight of the boy’s pink asshole. “Everything looks good so far.” He remarked.

Tommy could feel the man’s hot breath against his most sensitive skin and it sent a shiver up his spine. His cheeks turned rosy and he could feel his body temperature rising.

“Now I’m going to examine the anus with my fingers to make sure he hasn’t been penetrated in any way.” Dr. Ross declared, letting Mr. Holliday know exactly what was happening.

Jack watched as two of the Doctor’s fingers slowly traveled between his son’s buttcheeks and gingerly rubbed over his hole. Tommy let out a soft whimper when his anus was touched and that sound would have made Jack snap the neck of the man who caused it in any other situation but this one. Instead he stood there and grit his teeth while the proctologist checked his son’s virginity.

“It’s ok, I’m not going inside you. I’m just feeling you…” Dr. Ross assured his patient, delicately pressing his two fingertips against the young man’s anus with a light amount of force.

Tommy felt so embarrassed that he had made that noise when he was touched and to make matters worse, he could feel his asshole get hot and moist from the older man rubbing him.

“Well, Mr. Holliday... you’ll be happy to hear I can confirm your son has not been penetrated.” Dr. Ross told Jack while he continued lightly moving his fingertips over the boy’s quivering anus. “His hole is still nice and tight…” He added under his breath, enjoying the feel of the young man’s sensitive skin.

Tommy’s dick was becoming semi-erect as it hung between his thighs.

“Thank you, Doctor. I appreciate your help.” Jack said sternly. He had no doubt this man was having fun fondling his son but he knew he was a professional and this was his job, so he was trying not to get too angry.

Dr. Ross could tell Jack didn’t like someone touching his boy’s butt so he finally pulled his fingers back, revealing that Tommy’s anus was now glistening with sexual fluid. He couldn’t help but open his mouth at the sight of such a beautiful, wet, virgin bussy.

Jack inhaled sharply as he got an eye-full of his son’s moist boyhole for a second. “Are we, uhh… just about done here, Doc?” He barked, raising his voice.

“Of course, of course…” Dr. Ross chuckled, pushing back in his chair. “It was just a routine virginity check for today. You can go ahead and put your pants back on now, Tommy.” He said, trying to sound casual.

Tommy quickly got off the table and grabbed his discarded clothes. He felt humiliated getting wet and horny in front of his Dad for the second time.

“You can wait in the other room while your Dad and I have a chat.” Dr. Ross said to the boy.

Once Tommy had left the room Jack sat down and he and Dr. Ross faced each other. “So everything with Tommy is fine?” He asked, staring at the other men intently.

“Absolutely. His virginity is intact and his anus looks completely healthy.” The Doctor replied with a warm smile. “So, am I to understand that you’re currently looking for a suitable Alpha for your son to marry?” He inquired.

“That’s right.” Jack answered curtly.

“Well if I may say so, Mr. Holliday… I am a single man.” Dr. Ross began to explain. “And I am interested in such a…” He trailed-off trying to find an appropriate word that wouldn’t provoke the man’s defensive nature. “Such a fine young man.” He finished with a wide grin.

“Thank you, I’ll uhh… keep that in mind.” Jack replied thoughtfully.

“Please do, I’ll be more than happy to meet with you and the boy again and spend some time showing you what a good choice I’d be for your son.” Dr. Ross declared confidently.

“Thank you again for your help, Doc. I appreciate it.” Jack declared as he stood up.

“All in a day’s work.” Dr. Ross joked while he stood as well.

Tommy was sitting in the waiting room when the office door opened and the Doctor ushered his Dad out. His cheeks were still a bit pink from feeling self-conscious.

“Feel free to make an appointment again, anytime.” Dr. Ross said, smiling from Jack to Tommy.

“Thanks again, Doc. See you around.” Jack responded with a firm clap on the man’s shoulder.

“Goodbye, Dr. Ross.” Tommy spoke quietly as he stood-up to leave.

Dr. Ross grinned at the young man. “See you later, Tommy.” He told the boy as he watched him walk out of the building. The instant Tommy and his Dad were out of sight he sucked his two fingers into his mouth and tasted the young Beta’s sexual fluid. “Fuuuuck…” He muttered lustfully to himself.

Tommy remained silent as he and his Dad got back in the car and it wasn’t until they were halfway back home that he finally spoke up. “I’m sorry that I… y’know, I moaned like that.” He said, avoiding looking over at his parent.

“It’s ok, son. I know that you’re a hormonal young man and he was touching your… private area. It was natural that you’d get… physically aroused.” Jack replied stoically, keeping his eyes on the road.

“And the Doctor said everything is fine, right?” Tommy remarked, peeking over at his Dad to see his reaction.

Jack smiled and looked over at his son for a brief moment. “That’s right; everything is fine.” He reassured him, reaching a hand over to pat his boy’s thigh again. 

“I love you, big guy.” Tommy sighed, placing his hand over his Dad’s once more.

Jack chuckled happily. “I love you too, little guy.” He reciprocated, rubbing his son’s thigh.

Tommy felt like a weight had been lifted from his shoulders on the rest of the drive home.

As they approached their house Jack looked over at his son again. “I think I’ll discipline you again today, Tommy.” He told the young man before pulling-in to their driveway.

“Sounds good to me, Daddy.” Tommy replied obediently. 

They headed inside and Jack loosened his collar by undoing a few buttons on his shirt. “Alright Tommy, I’m gonna’ do it over the couch like last time.” He announced, taking a seat on the living room sofa. 

Tommy got into position, laying across his Dad’s lap with his crotch above the older man's groin.

Jack grabbed his son’s waistband and pulled his pants and underwear down to expose the boy’s bare ass. He once again couldn’t help but mentally acknowledge how undeniably attractive his own son’s ass is. “Just remember what I said last time; even good boys need to be disciplined.” Jack declared before raising his hand and bringing it down on Tommy’s buttocks.

Tommy let out a slight gasp at the hard impact and instinctively arched his back. “Daddy… what if what happened last time happens again?” He asked his parent.

“Don’t worry, I’ll be careful not to get my hand wet.” Jack replied bluntly.

Tommy was surprised by his Dad’s response. “Does that mean it’s ok if I get moist from being spanked?” He inquired. 

“I’d say it’s most likely inevitable.” Jack said as he continued to spank his son with firm, methodical strikes of his open palm. 

“Dad, can I ask you something?” Tommy spoke tentatively.

“Of course, son.” Jack reacted casually while he watched his son’s bum turn rosy red.

“I want to know more about my Father. You don’t talk about him very much.” Tommy explained. “I know that he was from another country and I know that he died giving birth to me, but I want to know more.” He proceeded cautiously.

Jack exhaled slowly. It was true that he hadn’t spoken very much about Tommy’s Father with him, the pain of the loss still resonated with him after all these years. Caring for Tommy so passionately had been his way of coping. He stopped spanking and instead gently rubbed one of Tommy's tender buttocks with his hand. “Alright, son. What do you want to know?” He questioned the boy.

Tommy smiled when his Dad caressed his bum, appreciating the loving gesture. “What was my Father like? Did you ever discipline him like this?” The young man asked, curious to know more.

Jack chuckled. “As a matter-of-fact I did, Tommy. Your Father was a bit of a troublesome boy when I first met him.” He admitted.

“Really!?” Tommy exclaimed in shock. “I guess I’m rather different from him, huh?” He commented.

“Not at all!” Jack laughed. “You remind me of him all the time. You especially remind me of what he was like after I… tamed him.” The older man declared proudly, running his hand over his boy’s reddened skin.

“Wow…” Tommy breathed out slowly, impressed with his Dad’s Alpha-male bravado. He could feel blood flow into his penis as he unwittingly became aroused.

Jack watched as his son’s anus wept a single glistening pearl of sexual fluid that slid down his supple skin and glided over the curvature of his buttock. “You remind me of him so much…” He muttered under his breath.

“How did you first meet?” Tommy asked.

Jack didn’t respond, he was staring at his son’s beautiful, shapely bum.

“Daddy?” Tommy said, confused by his parent’s silence.

“Oh, sorry… what was that, Tommy?” Jack replied, suddenly snapping back to reality.

“How did you and my Father first meet?” The young man inquired.

A smirk spread over Jack’s face. “How about I tell you the tale?” He offered.

Jack arrived at the Collington estate, he had never seen such a large, manorial home before. He walked up to the front door and grabbed one of the old brass door-knockers and banged it against the aging wood. About a minute later a butler answered the door and ushered him inside. He followed the man into the parlour where the master of the house was waiting for him.

“Mr. Jack Holliday here to see you, sir.” The butler announced.

Edward Collington Sr. dismissed his servant and invited Jack to take a seat. 

Jack sat down in one of the antique leather chairs and felt out of place in such a house. “So… what’s this all about? If you don’t mind me asking, Mr. Collington.” He inquired, his brow furrowing as he looked over at the older man.

“Thank you for coming, Mr. Holliday. It’s about my son, Edward Jr.” The wealthy, middle-aged gentleman said as he addressed the robust young teacher sitting before him. 

“Your son who got kicked out of the academy? There’s nothing I can do about that, it happened before I even started teaching there.” Jack began to reply.

“This isn’t about getting my son reinstated.” Edward Sr. interrupted the other man. “This is about my son's… behavioural issues.” He continued.

“Ahh… and you want me to do something about that?” Jack questioned the older man, scowling at him skeptically.

“Yes. In the short time that you’ve been working at the academy you have already earned yourself a reputation as a stern lecturer.” Edward Sr. explained.

“A stern lecturer?” Jack repeated, a bit confused by the man’s choice of words. “I teach physical education, Mr. Collington. And your son is a Beta, I teach Alpha students.” He clarified.

Edward Sr. cleared his throat. “I know who you are and what you do, Mr. Holliday. I invited you to come here because I hoped you could help me with my son.” He snapped in response, clearly feeling frustrated.

“And what exactly do you want me to do?” Jack asked, starting to wonder if he should simply get up and leave.

“My son… is disobedient.” Edward Sr. admitted, avoiding eye-contact with the other man when he said that. “I was hoping that a man with your reputation could discipline him.” He explained.

“Disciplining a young Beta is the responsibility of the boy’s Dad. Are you saying you need me to do your job?” Jack asked in a derisive tone.

“Yes!” Edward Sr. shouted in exasperation.

Jack was taken aback by how the other man had raised his voice, he didn’t think he had it in him based on his first impression of the man. 

“I want my son to behave and to be a proper young Beta male. But for reasons that are of no concern of yours, I am not able to correct my son’s behaviour myself. So I am asking you to do it for me and I can pay you handsomely to do so, if need be.” The older man explained.

Jack sat there and thought about the offer for a few minutes before he finally spoke. “Let me meet the boy.” He said.

“Thank you, Mr. Holliday…” Edward Sr. breathed out a sigh of relief.

“I haven’t committed to anything yet. I just said; let me meet him.” Jack reiterated. 

“Of course. His bedroom is up the staircase and down the hall, third door on the left.” Edward Sr. told Jack, sending him on his way. 

A few moments later Jack was standing in front of the boy’s bedroom door and tapped his knuckles against it twice.

“Come in.” The young man’s voice called-out from within.

Jack opened the door and found Edward Jr. lying on his bed reading a book.

The Beta male was about to say something when he looked up and saw it wasn’t his Dad standing in the doorway. “Wha– who are you?” He asked abruptly.

“Jack Holliday.” The Alpha replied as he took a few steps in the bedroom.

“You’re that instructor… from the academy…” Edward Jr. said as he stared at the imposing stranger in front of him.

Jack recognized the look of admiration and fear in the boy’s eyes and felt his lips begin to curl into a smirk. “I’m the physical education teacher.” He stated simply.

“What… why are you here?” Edward Jr. inquired nervously. 

Jack looked the young man over intently, he was wearing a casual buttoned-up shirt, a pair of blue jeans and a sports cap. He looked quite different from his Dad; like he didn’t belong in this setting, or that he didn’t want to belong here. “Your Dad wants me to discipline you.” Jack answered bluntly. 

The boy’s mouth hung open and his eyes widened at the news. Edward Sr. clearly hadn’t discussed this idea with him. “A-are… are you g-going to?” He stammered in alarm.

Jack chuckled at the young man’s response. “You want me to?” He challenged the Beta.

The young man suddenly closed his mouth and tried to look less anxious. “It doesn’t matter…” He muttered. “Won’t change nothin’ anyway.” He added, speaking in a more unsophisticated manner than his uptight parent. 

“And why is that, Edward?” Jack asked the boy.

“Eddie.” The young man replied.

“What?” Jack grunted in confusion.

“My name is Eddie!” The young man snapped at the Alpha.

“Alright, Eddie… Why do you think me disciplining you won’t change anything?” Jack inquired.

“Because nothing else has.” Eddie said, looking away from the older man.

Jack stepped right up to the bed and looked down at the boy. “Things will be different with me…” He declared ominously.

Eddie looked up at the imposing man towering over him. “Why is that?” He breathed-out timidly.

Jack grinned down at the Beta. “Because I know how to discipline boys.” He chuckled confidently.

Eddie swallowed nervously. “You… you’re going to be disciplining me from now on?” He spoke quietly, like he already knew the answer but was intimidated by the truth.

“That’s right boy. Now…” Jack began to say, unbuckling his belt and pulling it off. “Take your pants and underwear down.” He instructed the young man.

Eddie laid there for a moment with his mouth agape, staring up at the hulking figure before him in awe. “Y-yes, sir.” He stuttered nervously before he meekly complied, sliding his pants and underwear off and exposing his genitals. 

Jack’s grin widened when he saw that the young man’s penis was already semi-erect and still growing. “Alright now, let’s get you over my knee.” He growled.

“Daddy!” Tommy interrupted the story with a sharp gasp. “Did you really spank him with a leather belt the first time you met?” He asked his parent incredulously.

Jack laughed while he stroked his boy’s bare bum. “I sure did, son. I started disciplining your Father from the very start and turned him into the submissive husband that gave me my greatest gift in life…” He replied, gently patting one of Tommy’s buttocks.

The young man blushed at his Dad’s loving compliment. “Daddy, I… I think I want you to discipline me like you disciplined my Father.” He said, looking back over his shoulder at the older man. 

Jack was wearing a belt at the moment. “Are you sure, Tommy?” He questioned his son in a serious tone.

Tommy didn’t take any time to think it over. “Yes, I want to experience your discipline just like my Father did.” He answered honestly. 

Jack felt blood rush into his manhood in reaction to his son’s bold statement. “Alright, Tommy…” He muttered, slowly sliding off his belt.

Tommy looked forward and arched his back while he laid across his Dad’s lap.

Jack held the leather belt in one hand and raised it into the air before bringing it down on the boy’s exposed buttocks. 

“Ohh!” Tommy moaned out loud at the sudden sting of pain.

Jack was shocked to discover how good it felt to hear his own flesh-and-blood make that sound. He raised the strap of leather again and whipped his son’s ass a second time.

Tommy’s eyes closed and his mouth opened wide as he sucked-in air heavily. 

Jack didn’t relent, he disciplined the boy just as he did his Father years ago. He raised his arm and spanked the boy a third and fourth time with the makeshift whip. 

“Uhhh… uhhhh!” Tommy panted breathlessly. He could feel his body temperature rising and the now-familiar sensation of his anus becoming moist while he endured his Dad’s discipline. His dick had become stiff beneath him as it rubbed against one of the older man’s thighs. 

Jack listened to the undeniably erotic noises his son was making and felt his cheeks redden underneath his beard. He looked down and saw that Tommy’s butthole was now sopping wet and quivering, he knew every hormone in the young man’s body was screaming for sexual gratification. He lifted his arm up higher than before and brought the belt crashing down against his son’s tender bum harder than ever. 

“Daaad!!!” Tommy shouted as he reached climax, his erection shooting his load against the older man’s pants. 

Jack had bit his bottom lip while he watched the impact cause Tommy’s sexual fluid to spatter against his round buttocks in a multitude of droplets.

Tommy slowly turned his head to look back at his parent over his shoulder while he struggled to catch his breath. “Is… is it ok?” He asked, blushing profusely.

Jack smiled at his boy. “Yes, son. It’s fine.” He reassured him. “I told you it’d be inevitable.” He chuckled.

Tommy nodded his head in acceptance.

“Now go get cleaned-up upstairs.” The Alpha instructed his son, rubbing one hand gently on the Beta’s lower-back.

“Yes, sir.” Tommy replied obediently as he got up and grabbed his discarded clothes before heading upstairs.

Jack waited until a few minutes passed after the boy had left before he finally stood up from the couch, an obvious erection in his pants. He headed up the stairs himself and heard the shower running in Tommy’s bathroom. He walked into his bedroom and stripped nude. “Fuuuuck…” He breathed-out softly, grabbing his throbbing cock in one hand. Jack quickly got out some old photographs of himself with Edward Jr. back in the day. “Eddie…” He growled lustfully, stroking his huge erection while he looked at the images of his beloved late husband. The memory of Eddie never failed to rile-up Jack’s more aggressive sexual urges. With one hand he jerked his manhood and with the other he groped his brawny pecs and pinched his nipples. Jack's balls swung back and forth while his hand glided up-and-down his prodigious shaft. As the man masturbated to relieve his pent-up sexual frustration he couldn’t help but remember his full conversation with the elder Edward Collington and felt a pang of guilt. Jack didn’t like lying to his son, but he wasn’t comfortable telling Tommy the full truth of what exactly happened the day he met his Father. There were some things that were too personal to share with his son, too inappropriate. And one thing in particular that Edward Sr. had told him back then had stuck with him for all these years, and it had recently become uncomfortably relevant.

“I want my son to behave and to be a proper young Beta male. But for reasons that are of no concern of yours, I am not able to correct my son’s behaviour myself. So I am asking you to do it for me and I can pay you handsomely to do so, if need be.” Edward Collington Sr. had explained.

“Well, Mr. Collington…” Jack sighed. “I don’t think I can properly discipline your son if I don’t know what the problem is exactly.” He replied. “So unless you’re gonna’ tell me what it is that’s no concern of mine, I might as well be on my way.” He added, standing up from the chair. 

“No, please!” Edward Sr. pleaded abruptly. He looked down in shame for a moment. “I’ll tell you. Do you know what men often say about Beta males my son’s age? Concerning their hormones and their feelings for their Alpha parent, that is.” The older man inquired.

Jack chuckled as he realized what the other man meant. “Yeah, Beta boys are always hot for their Daddy.” He replied bluntly.

Edward Sr blushed at the remark. “I wouldn’t put it so… vulgarly. But yes, it’s true. My son struggles with his… temptations.” He admitted, still avoiding eye-contact.

Jack sat back down and thought about the offer for a few minutes before he finally spoke. “Let me meet the boy.” He said.

“Thank you, Mr. Holliday…” Edward Sr. breathed out a sigh of relief.

“I haven’t committed to anything yet. I just said; let me meet him.” Jack reiterated. 

“Of course. His bedroom is up the staircase and down the hall, third door on the left.” Edward Sr. told Jack, sending him on his way. 

Jack got up and turned to leave the room.

“And one more thing, Mr. Holliday.” Edward Sr. spoke-up, stopping Jack before he left. “It’s true what they say about Beta males desiring their Dad when they come of age. But what they don’t say as often… is that the Alpha male inevitably desires his son in return. One day you may be tempted as I have been.” He explained solemnly. 

Jack thought of Edward Sr.’s words while he continued to pleasure himself. He could no longer deny that he had begun to feel… tempted by Tommy’s burgeoning sexuality. His son had developed into an attractive young man with a beautiful body. Despite Jack’s strong traditional morals the warning he had received from Edward Sr. had come to fruition; he felt sexually attracted his own son, and there was evidence that Tommy felt the same. Jack thought about that evidence for a moment, the sweet sexual fluid from his son’s anus. The sight of Tommy’s bare, wet ass reminded him so much of Eddie back when he used to discipline him with rough spankings. The sight of Eddie’s slick, quivering hole always filled Jack with the most primal, insatiable lust. To behold that same thing with his own beloved son was almost too much to bare on Jack’s psyche. He tried to push the thoughts of Tommy away and focus on the memory of Eddie. He reminisced on the first time he had fucked that boy; the sensation of sliding his girthy cock up that tight, wet, virginal asshole, the sound of Eddie whimpering desperately as he was stretched and filled, the feel of him struggling in vain underneath his body as Jack held him down. “Ohh Eddie…” Jack moaned, closing his eyes as he kept masturbating. “Eddie…” He repeated, his muscular chest heaving while he breathed heavily. But the greatest memory of all is when he made Eddie cum the first time he fucked him and heard him call out Jack’s name in the heat of passion, not Edward Sr.’s. “Ohhh, that's my boy!” Jack grunted as he brought himself over the edge, spilling his seed onto his bedsheets. “Fuck…” He muttered, rubbing his chest hair while he tried to catch his breath. The Alpha male walked into his adjoining bathroom and started a cool shower for himself. Jack knew it was going to be difficult to find a man he considered worthy to be the husband for his son, but he was determined to try. And there was something else he was determined to do; he was going to continue disciplining Tommy just as he did with Eddie.