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Herbie's First Time

"Herbie finally has real sex in high school…"

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Herbie was as cute as hell. He was small compared to all his fellow students and from the time he started high school, a boys' boarding school to be exact, he was seen as a mascot of sorts. The boys could not keep their hands off him and he was constantly being playfully hugged.

It was never in a salacious manner, but more like an older brother ‘teasing’ a much younger sibling whom the entire family just adored. His big brown eyes and cherubic face simply induced smiles on the faces of everyone that encountered him. Herbie loved the attention and didn’t mind being ‘manhandled.’

From his first year in high school, he was always allotted a female role in all the inter-house plays that took place on an annual basis. The boys just loved participating in these twenty-minute plays, and the competition was fierce. No teachers or staff members were allowed to get involved in this tradition, and it was purely a one-night competition totally arranged by the boys at the school.

Apart from that, because of the very dynamic English mistress at the school named Mrs. Adler, the school also had an annual theatrical production. The annual play or musical was always ardently supported by the local community, and naturally, all the parents of boys attending the school. The reason that these productions were very popular was because of Mrs. Adler’s reputation. She had the ability to turn a sow’s ear into a silk purse. This ‘major’ production was staged over five nights and also included a Saturday matinee.

From the very first year that Mrs. Adler encountered Herbie, she knew that a star had been born. He was regarded as the Daniel, or maybe that should be Daniela, Day-Lewis of the school. Ms. Adler’s greatest challenge yearly was assigning him the appropriate role, because he was simply light years ahead of all the other boys as an actor and always carried the show.

This point was comprehensively demonstrated when she staged; ‘Joseph and the Amazing Technicolour Dreamcoat,’ during Herbie’s final year at school. Mrs. Adler rued the fact that she didn’t have three Herbie’s. He would also have been perfect as Potiphar or The Pharaoh, but unsurprisingly, Herbie, of course, was chosen to play the leading role as the narrator, finally acting in his first ‘male’ role.

At the start of Herbie’s final school year, shortly before he turned seventeen-years-old, Jean-Luc De Villiers became a housemaster at the school. He was attending a nearby university, studying theology. Jean-Luc’s father was a minister in a staunch United Churches of Christ community that wholeheartedly embraced the teachings of John Calvin.

Jean-Luc was obviously a believer, but he had a deep-seated secret that no one else knew about. He was attracted to men. JL, as he was generally referred to, had not attended a boy’s boarding school and therefore, had never previously been exposed to the delight of being in the abundant presence of beautiful late-teenage male nudity. In as much as the masters had their own private bathroom in the building, showering with all the final year boys in the general open-plan ablution area proved to be daily delectation for him.

For the boys in the house, the presence of JL in the showers was as intriguing as it was for JL. JL was a fairly handsome man, but he had one feature that made him stand out like a sore thumb. JL was unbelievably hairy. His entire body was covered with dark black hair. Added to this, he had also decided to grow a beard and allow the head on his head to get rather long.

Being a theology student, this gave him an almost biblical appearance. For all the boys, however, it was a source of great amusement and frequent jokes about him being the missing link were made. These jibes, of course, were only made when he was out of earshot.

Jean-Luc fell under Herbie’s spell from very early on. Of all the talent he observed around him, nobody came close to Herbie. Intuitively, JL also believed that Herbie was gay. What further impressed JL was that for such a small guy, Herbie was rather well-endowed. JL had always wondered what it would be like to be anally penetrated. In addition, the thought of Herbie’s beautiful mouth around his cock made JL crazy with lust. JL wanted to have sex in a versatile fashion and the term, ‘flip-flopping,’ had always intrigued him.

Being religious, however, JL had an old fashioned notion that abstinence from masturbation was a cross that one should try to habitually bear. In truth, JL only ever lasted four days before succumbing and manually relieving his pent-up sexual frustration. Naturally, Herbie was the illusion that always fuelled these sessions.

The advent of the annual theatrical production was heaven sent for JL. He loved any form of woodworking, which was a favourite hobby of his. He, therefore, generously agreed to help with the sets that Mrs. Adler required for the show. Given his religious background, however, he informed Mrs. Adler that he did not want any accreditation on the playbill for the production. Given the nature of the show, most people from his background would regard ‘Joseph’ as blasphemy of sorts.

In the two weeks before the first night of the production, rehearsals and stage building were in full swing. As the rehearsal for the evening ended at ten-thirty with a fortnight to go, JL still had a lot of work to do. As everybody except JL was about to depart, he looked at Herbie and asked, “Could you stay a short while longer, I just want to check out some staging logistics with you?”

This seemed like a strange request to Herbie because after all, that would be the kind of thing that Mrs. Adler and JL would normally discuss.

It soon became clear once everyone had gone and JL and Herbie were alone, that JL was grasping at straws. Breaking the mild tension that now existed, Herbie decided to throw JL a lifeline.

“May I help you out with some painting Mr. De Villiers?” Herbie then asked.

“Yeah… sure,” JL replied with a look of relief on his face. “By the way, when we’re alone like this, please call me JL,” Jean-Luc concluded.

After Herbie got stuck into his task, JL frequently stood close to Herbie to check on his progress and as he did so, the space between them kept narrowing. Finally, with JL and Herbie’s bodies touching, JL’s hand rested on Herbie’s shoulder. The excitement in JL’s breathing soon began to electrify a surge of horniness in Herbie. Herbie was completely blown-away by JL’s forwardness and wondered in something more sexually stimulating was on the horizon for him. He also pondered if he was simply misreading JL’s ‘friendliness.’

Herbie had never thought about JL sexually. After all, not only was JL a housemaster but more importantly, JL was also a student of theology. Truthfully, Herbie had admired JL in the showers and JL’s hairiness had never perturbed Herbie at all.

Herbie had never had a comprehensive sexual encounter before, and circle jerks were about as exciting as things had ever gotten in the past months. Recently, there had been one occasion when another boy had actually touched Herbie’s cock one evening when they found themselves alone, but that hadn’t developed any further. Much as Herbie had hoped for a repeat performance, it was clear from the following day that the boy had a huge dose of homo-remorse.

Herbie’s reverie was soon obliterated when JL suggested that they should call it a night.

‘Oh fuck,’ Herbie sadly pondered, ‘Nothing is going to happen, yet again.’

En-route back to the house, however, JL said, “I need a shower… are you going to join me?”

“Yeah, that’s a great idea,” Herbie enthusiastically replied.

When Herbie entered the ablution area, JL was already showering. Herbie was intrigued by the combination of the white foam on the dark hair of JL’s body. It almost looked as if JL’s body was covered in a dark grey blanket.

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With the stimulation of the evening thus far Herbie soon had to turn his body to face away from JL, as he got a monster hard-on.

“Why are you facing the other way?” JL asked.

“Umm… well, I sometimes… I get aroused, when I shower,” Herbie embarrassingly stammered.

“So, who cares? … I also frequently do.” JL replied reassuringly, before resuming, “Turn around and face me, buddy, you’re being rude.” JL‘s tone was not chastising, but playful.

As Herbie turned to face him, JL’s eyes lit up when he observed the impressive mast that the young man who had become the desire of his dreams, was sporting.

The shy look on Herbies’ face made him even more desirable. Unable to resist, JL now extended his arm and took hold of Herbie’s cock in his left hand. The jolt of adrenalin that flushed through Herbie’s body was incredible. Herbie first looked down to witness the spectacle, before he momentarily looked up into JL’s eyes.

When Herbie once more looked down, JL’s cock was as hard as his. In a reciprocal gesture, Herbie then cupped JL’s dick in his hand. Yet another jolt racked his body as he did so. Nothing this exciting had ever happened to Herbie before.

Once more, disappointment followed when JL let go of Herbie’s dick and suggested that they should dry themselves and head off to bed.

As they exited the bathroom with their towels around their hips, as Herbie was about to head off to his dormitory, JL took hold of Herbie’s arm and steered him towards his apartment. They had no sooner entered before JL had removed both their towels before embracing Herbie.

An intensive kissing session now got underway, to the mutual delight of both guys. With their bodies fused and grinding into one another, Herbie was becoming overwhelmed by lust. Shortly, JL’s hands found their way to Herbie’s shoulders before he commenced pushing Herbies’ body downward.

Once on his knees, Herbie couldn’t believe that he was about to suck his first cock. The scenario almost seemed unreal to him.

JL instantly began running his foreskin across Herbie’s lips. Unable to hold out any longer, Herbie’s lips parted in an inviting gesture. JL first lodged his dick in Herbie’s warm mouth, before his hands commenced caressing Herbie’s head. As their session blissfully ensued, both guys found themselves a state of total euphoria. JL had never felt anything more heavenly in his life. The pleasure of Herbie’s hot mouth was beyond any gratification he had ever felt before.

Their episode was regrettably cut short when JL gaspingly announced, “Jeez, buddy, I’m getting very close… Do you want me to cum in your mouth?”

Herbie signalled his approval as his hands firmly grasped JL’s furry hips.

“I must warn you that I haven’t cum in five days, so my nuts are really full,” JL lustfully warned.

Herbie once more signalled by gripping JL’s hips even tighter.

The deluge that followed stunned Herbie, as JL’s body began to shudder. Not only because of the abundance of spunk, but also the velocity with which it was delivered. Herbie spluttered and swallowed to the best of his ability as the lava just kept surging, as he hung ant JL’s hips for dear life.

With Herbie face and chest drench with cum and saliva, he looked up at JL. The smile on Herbie’s face said it all as he got to his feet. JL then leaned over and retrieved his towel from the floor. After wiping off Herbie’s face and chest, JL asked, “Do you like the taste of my spunk?”

“Definitely,” Herbie enthusiastically answered.

Herbie was overjoyed when JL once more embraced and recommenced kissing him.

After a few minutes, JL pulled his head back slightly and spoke. “Now it’s your turn.”

Herbie now presumed that JL was about to his knees to suck Herbie’s cock. Instead, when JL spoke again, Herbie got the surprise of his life. “I want you to fuck my arse,” JL said in a horny tone, before frowning and concluding, “If that’s okay with you?”

On a night of unbelievable enchantment, these words blew Herbie away completely. His sex life had gone from nada to spectacular in a matter of no time.

With a dumbfounded expression on his face, Herbie asked, “Are you sure?”

In a voice thick with lust, JL replied. “Yes. I want you to pop my cherry.”

“Okay… no problem,” Herbie replied, stammering with excitement.

“Just use your spit and don’t hold back. I don’t care how much it hurts because I want to remember this night,” JL said, as he turned and placed his torso on the bed.

Herbie watch spellbound as JL’s hairy paws pulled his cheeks apart. As Herbie scanned the hairy crack that opened in an inviting gesture, his tongue excited twirled in his mouth to encourage as much saliva as he could. After placing his hands on JL’s butt, Herbie’s thumbs commenced parting the hair in search of the oyster that awaited him.

As the pink entrance of JL’s portal came into full view, Herbie’s dick was so hard that he was afraid it might burst. Herbie was so focussed that he scarcely heard the low groans that JL was making.

Herbie now started spitting on JL’s pucker as his thumbs began to work JL’s hole. Shortly, Herbie’s thumb popped into JL’s manhole and commenced lubricating the entrance. Once the thumb began to spear in and out more easily, Herbie also started turning his digit to and fro to relax the tightness of JL’s sphincter.

Having prepared JL’s butthole, Herbie now also started applying spit to his pulsing cock. Herbie was in a sensual trance as he finally placed the head of his dick at the cavern of pleasure that beckoned him. As Herbie’s index finger began pushing his knob’s head into the portal, JL’s groans and the restriction from JL sphincter that Herbie was wrestling into submission, felt awesome. When Herbie’s victorious glans ultimately beset the combative resistance, the feeling was beyond description. With his cock-head now solidly lodged, the final onslaught into JL’s portal commenced.

To the sounds of muffled grunts, Herbie watched as inch by inch his dick raided JL’s backside. As JL began to pant, Herbie halted his incursion momentarily. After holding still for a short while, Herbie asked, “Are you okay.”

“Fuck, yeah… that is very sore but totally awesome,’ JL gasped. After a pause, JL begged Herbie to fuck him really hard.

The warmth and tightness of JL’s sheath was mesmerizing. In all his life, Herbie had never felt anything more blissful than this. Herbie now solidly began to pummel JL’s arse.

In sensual overload, Herbie soon began to feel his impending release. He wanted it to last longer, he really didn’t want to cum too quickly… ‘Fuck, slow down,’ he mentally chastised himself.

‘No, fuck no,’ he intoned in his mind. ‘Hold out, fuck… I must hold out a bit longer,’ Herbie mentally wrangled.

‘Oh, fuck, no,’ Herbie thought as he grunted, “Oh, shit, I’m cumming.”

In what looked like a display of St Vitas Dance, Herbie’s body became infused with gratification as he gyrated on top of JL. The release was more intense than anything that Herbie had ever felt before.

Drained, he collapsed and lay on top of JL once he was done.

Afterward, when they both got off the bed, JL embraced Herbie for the third time and kissed him again.

“I wish you could stay all night,” JL said as their bodies parted and Herbie was about to leave.

“Me too,” Herbie replied.

“Will you stay behind tomorrow night and help me again with the backdrops for the show?” JL then asked.

“Sure, anytime,” Herbie said with a smile.

“Maybe we can alter positions tomorrow night so I can pop your cherry,” JL concluded with an impish grin.

These words were like music to Herbie’s ears.

Published 
Written by Tuppie
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