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On Holiday with My Dad - Extra

Background Story. Gary tells Ben about his early life.

Spankmasters
May 2, 2024
7 min read
older youngerOn Holiday with My Dad - Extragay
On Holiday with My Dad - Extra
On Holiday with My Dad - Extra

On Holiday with My Dad - Extra

During my 18th year, I commenced college in a city, and each day, I journeyed on the bus from the town. That's when I stumbled upon the bus station restrooms. These were rather dilapidated and featured an antique metal urinal lining one side of the wall.

The initial time I entered, I had genuine intentions, yet I noticed that the other two men appeared to be taking their sweet time relieving themselves and one of them kept stealing glances at me. He inched towards me, gripped my penis, and began moving his hand up and down, stroking me at a relentless tempo.

At that moment in my existence, I was naive and inexperienced. I allowed him to bring me to climax, flood the rear of the urinal with an immense amount of semen. I exited the washroom, dashed outside, and waited for the next bus, my thoughts in a chaotic mess.

Needless to say, my visits to the restroom became a daily ritual. The moment I would approach, my erection would become pronounced. There were habitual patrons, always two or three older men present, eagerly awaiting my arrival.

All I required was to aim my genitals in their direction, and they would promptly gatecrash my private affair. One would fondle my shaft, while another focused on releasing my prolific sperm deposit.

Certain men even attempted to kiss or convince me to return home with them, but I remained steadfast, keen on consummating my business and swiftly departing.

My next rendezvous involved a trip to the local pub. There, I encountered Debbie, the future mother of your children. She was chatting with two of her friends, shockingly spirited.

"Buy me a drink, Gary," she flippantly remarked.

I dimly recognized her from school, but encountered no interaction other than a few encounters in the hallway. She was appealing, strolling across the room and addressing me, implying a significant interest in me.

I spoke casually, "Why should I buy you a drink?"

She continued to smile enthusiastically and waved at her friends, who were enamored with the attention.

"They double-dog dared me to come over and seduce you."

"Well, let's get you a drink."

We savored the rest of the night together, then embarked on a romance, and eventually consummated our relationship. With the announcement of her pregnancy not too long after, I was engulfed in astonishment.

We conformed to her parents' and other community members' wishes, married, and relocated into the home of her parents, witnessing discomfort from the onset.

You promptly descended and Debbie's heart appeared to become enslaved by our child. My role appeared antiquated, and my presence became burdensome. This led me to essentially abandon our union.

Falling for a colleague, a friend of her own, I committed a clumsy mistake, resulting in our separation.

Forced to depart my home, I discovered a potential solution in the form of a job. It involved joining a tree-planting crew in the Scottish Highlands with free living quarters.

To my disappointment, the surroundings were secluded, as the nearest village was ten miles away, hampering normal activities, such as visiting a pub for leisure and company from women. My home was an ancient cottage with a large central kitchen and another spacious room featuring three bunks. The toilet and rudimentary shower (without a curtain) were located near the entrance.

The work was physically demanding yet rewarding, as my team members and I escaped up the hillside in the morning to cultivate young trees. Our crew chief, Gordon, was a 50-year-old well-built man with closely cropped gray hair and stark black eyes, who took note of every action. Two individuals from the Western islands and an old man in his late sixties rounded out our gang.

The workload was demanding, yet enjoyable under sun-kissed skies, with one member, Derek, dividing us into batches, sorting seedlings for planting, and executing the culinary duties while we were away and ensured our home ran efficiently.

However, evenings were a burden. If I was the last one to shower, I was privy to a hurried wanking session. Although this personal moment was not a guarantee, the fear of being interrupted was constant.

While leaning against a tree, I took out my penis and started stroking, closing my eyes and letting my mind wander. With no chance to masturbate in the past two days, I needed some release.

As I thrust my pelvis, imagine feeling my hand wrap around my erect member, I ejaculated explosively in the air. Once finished, I went back to my routine, relishing the release it gave me.

One evening, I thought I heard someone sneaking about in the trees, only to conclude it must be a deer.

A day later, I had just brought my penis to full erection when I heard the crinkling of leaves. Opening my eyes, I saw Gordon watching me from behind a bush. Undecided for a moment, I finally decided to carry on with my masturbation. Gordon joined his companion, getting on his knees to suck me off. This was unexpected, as he was an imposing guy.

He sucked on my length, his lips gliding up and down. It appeared he didn't have his first male encounter, so I remained unsurprised by his proficiency.

"Want to suck me once more?" I asked.

"Sure!" he replied.

He dutifully obeyed the request with content in his voice.

The two of us returned to our cottages, enjoying the bittersweet end to our togetherness.

One afternoon, I overheard Gordon's question to himself. "If Gordon wants it, I can help?" he asked, referring to me. My cock was already sparkling hard.

He came closer, expressing lust in his face. "I'm dreaming too," I said.

Gordon quickly wanked me till I reached orgasm, emptying his mouth as he swallowed every drop.

As we walked back, he offered, "Anytime you need a hand, just touch your forehead to the ground."

We decided on meeting every night in the woods.

One night, I arrived early and held my erection, eagerly anticipating the blowjob. When he arrived, he didn't kneel immediately.

"We were planning to do it tonight?"

He looked at me and proposed, "Will you fuck my asshole?"

We had never done this before, but it intrigued me.

He lowered his pants, revealing his hairy and rose-like butthole. Sweat encompassed Gordon's wrinkled, enlarged hole, hinting he may have prepared himself for this.

I pushed my hard length into his dark maw, inserting my manhood in his buttocks. He felt a virgin, tight and resilient. Groaning at the pain, I gathered my strength before spanking his buttocks, dominating his body. Feeling dormant sensations, I maneuvered my member in and out of Gordon's tight treasure. Once I came, I pulled out.

His smile told me, "It's great seeing you enjoying it. I haven't had sex for a long time."

After he dressed, he declared, "If you need some comfort, just give me a subtle, non-explicit head nod."

"How about tomorrow?" I asked.

"You can count on it," he grinned.

Every evening, we met in the woods. Sometimes, we would fuck and other times, he'd pleasure me. My eyes often wandered to his well-built behind, observing the glory of his muscular arms while planted beside me.

One night, Gordon inquired, "What about letting me fuck your hole?"

Initially, I felt uneasy, but I remembered how he accommodated me these past few weeks, and decided to agree.

With a serious face, he wiped his mouth and stood up.

"Come," he beckoned, motioning me to follow.

Back to my cottage, I found myself considering him. He was still in his underwear, looking tense and uncertain, as if he expected rejection.

I encouraged him to relieve his impulse by inviting him to fuck me. Gordon pulled down his pants. Our eyes locked as I slipped my manhood into his backside, biting my bottom lip.

After entering him, I adjusted to the tight sensations. Pain deterred me, but eventually, he stretched out my phallus into his depth. I was elated by the thought: I've scratch his backside and now my shaft fully extended inside him. Deciding to take advantage, I plunged forcefully, enjoying the tight confines of his backside.

Gordon buckled at the unbearable pain; finally, I relaxed to spare Gordon his agony.

Annoyed by my inattention, I barely spared a glance at him, getting used to the advances of Gordon's huge tool, piercing my insides. He held out till my third time, creating a cycle of pleasure and pain.

The summer came to a close, and we untimely resumed our jobs.

"I'll miss you," Gordon lamented.

He prepared me for later by providing a list of references and his own compliment about my abilities.

In the last night, I lay back as Gordon's seed filled me. This was the end to our wooded adventures.

The process of remembering it left my member aching for that thick, throbbing rod. The reality of the situation hurt, and I mourned our secret lovemaking moments.

The sun rose as I began heading back home. Gordon followed me, having packed a bag. My anxiety wore off as he wrapped his arm around me.

"Since we're returning to our separate lives," he explained, "I'd like you to snuggle with me tonight."

"I'd like it too," I answered.

As we shared another night, the end of us 'playing' was nigh. I'd miss the sound of our moans, the warmth of his touch, and the scent of his cum in my buttocks, but life went on.

I've been at home for a week before heading to the city to attend a journalism course. I managed to save up enough money during the summer to pay for a flat rental and found a job in a pub to continue earning.

Throughout this time, I've primarily dated women, but several times I've had quick encounters with good-looking men for some variety.

Currently, I'm enjoying my time with you, Ben, which surpasses all my expectations - thank you for inviting me on this vacation.

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