Beginning the Journey: Part 3
NOTE:
This is the third ghostwritten instalment for a Literotica friend and fan. As with previous submissions, I received the basic outline of the experience, which I have extended and embellished for your reading pleasure.
Charles sat in the bar swirling the ice cubes in his glass of scotch. His stomach and anus had received generous deposits earlier that night from an unexpected source. He had reached a whole new level of euphoria in his journey. While a committed 'bottom' who let men do as they wished with him, earlier that day, Charles had seduced someone for the first time that, subsequently, inducted him into the world of cross-dressing.
Ken was a real find. He was a member of a local amateur dramatics group of the town where his Grandmother lived. It was Easter, and Charles drove over for Sunday lunch. Among the topics of conversation was the latest play rehearsal,
HMS Pinafore
. She mentioned how the new musical director had brought an energy to the play with his inspired interpretations. A retired high school music teacher, Ken supplemented his pension by giving piano lessons on the weekend.
Charles analysed each detail his Grandmother imparted about Ken searching for any hint about the latter's sexuality. There was nothing overtly mentioned, but his Grandmother offered to facilitate a meeting if Charles wanted to take lessons.
Hers was not a coincidental offer, thought Charles, and he wondered if his Grandmother knew about or suspected his sexual preferences. A man of Ken's vintage did not particularly appeal to Charles given that he was not yet thirty years old, but cock is cock.
With nothing to lose in a meeting with this retired piano teacher, Charles asked his Grandmother to set it up. After a quick phone call, one Saturday several weeks later, Charles was taken to meet Ken.
The initial meeting was very formal, but Charles knew when they shook hands that a definite frisson passed between them. Ken gave his guests a quick tour of his palatial home and exhibited his music studio, which showed off a mighty grand piano in the centre, an impressive library of books about musical history, theory, styles and genres. The walls were adorned with numerous awards and certificates, a testament to the man's obvious talent. The large bay windows maximised the natural lights, and they opened to a timber decking.
While they were not shown the upstairs, Charles noted the lack of feminine touches throughout the house. Before departing, Ken asked Charles if he wanted to take piano lessons. Throughout the tour, Charles was evaluating Ken and, despite his earlier ageist hesitation, was impressed. Ken looked much younger than the number on his birth certificate; he was slim, good looking with fine, sandy hair, and the intelligence and grace oozed from him. Well dressed, Ken wore a particularly tight pair of black trousers that exhibited a prominent bulge. In short, Charles found Ken mesmerising.
"What's Ken's status," Asked Charles casually as they drove back to his Grandmother's home through the small town's streets, "Is he married, widowed or single?"
"No," She laughed, heartily, "He's a 'friend of Dorothy's'."
"Oh," Charles answered, trying to hide his disappointment, "Who's she?"
Charles' Grandmother looked askance at her grandson's ignorance.
"It's a turn of phrase," She chuckled, "Use your interweb thingy and look it up."
When they arrived home, Charles excused himself, sat on the toilet and looked up the phrase on his phone. The dawning realisation of what it meant made Charles' heart soar and his earlier suspicion that his Grandmother knew of his sexuality. The meeting was not a coincidence after all, and Charles' Grandmother was playing cupid.
With Ken's business card in his back pocket, Charles made his way home and, that night, had a deliciously slow wank in bed trying to imagine every possible facet about Ken's cock. Charles came particularly hard with explosive ropes of hot sperm landing on his belly. As Charles massaged his seed across his clammy skin, imaging Ken as the masseuse, secondary bolts of pleasure rock his body.
Taking Ken up on his offer to teach Charles the piano, lessons quickly progressed because he could practice what he had been taught at his Grandmother's house and become proficient within three months. Ken taught Charles the basics of musical theory and how to read sheet music which was no mean feat for Charles' generation and limited academic interest.
When Charles moved onto set pieces, Ken would stand at his shoulder to turn the pages and point out any mistakes. Ken's teaching method was to insist that Charles played the same piece repeatedly until he nailed it. Next, Charles was instructed to play that piece of music from memory without the sheet music in front of him. Charles found this task a challenge but usually managed to play right through without any errors on the third or so attempt.
Upon one error-free play through with Ken standing by his shoulder, Charles looked up expectantly for further instructions. He saw Ken standing with his eyes closed and a faint smile on his face, swaying slightly, but his crotch was bulging with an obvious erection.
Charles knew the opportunity on offer instantly, and his pulse raced dangerously. He had never been bold enough to make the first move, allowing men to use his body as they pleased, but an insane resolve possessed Charles, and he was determined to show his intentions.
Reaching out, Charles ran his fingers lightly over the bulge. He was rationalising that the worst that would happen would be for Ken to stop the advance. Charles already had an excuse worked out if Ken resisted.
The excuse was not needed. Instead, Ken said nothing and swayed languidly with a look of contentment on his face. As a result of this tacit approval, Charles continued massaging his teacher's crotch, lightly at first but with continued pressure. Ken's breathing changed at that moment, and it became slightly faster as Charles' exploration continued. Amazed at his audacity, Charles' cock quickly became rock hard.
Emboldened, Charles found the zipper to Ken's tight trousers and gently pulled it down. Undoing the clasp, he let Ken's trousers fall to his ankles, revealing something very unexpected. Instead of encountering a pair of briefs or boxer shorts, Ken wore a tiny pair of red ladies' panties which fit snugly around his big cock. Charles also noted the wet spot where Ken had leaked pre-come.
Unable to resist, Charles ran his finger over the wet spot, then licked it tasting Ken's ooze which made him shiver with a lust not previously experienced. Next, he pulled the waistband down slightly to release his cock, and out it sprang, the head slick, shiny and purple, then he finally spoke.
"Charles, you shouldn't," But there was not much conviction in his voice.
Any resistance Ken may have had melted away when Charles lowered his head and licked off the string of precum, swallowing it audibly.
Charles took a second to admire Ken's mighty cock. Since his first encounter with Michael back in the day, Charles had played with a lot of dick, no two were the same, and each had its unique characteristics, but the slab of meat facing Charles at this moment was impressive. Ken's cock was long, thick and quivered like a spear when Charles gently blew on the tip.
Extending his jaw to its maximum extent, Charles reached forward and stuffed his mouth with Ken's offering. At first, it was a challenge to get past the helmet, but with Ken's hands on the back of Charles' head, he began rocking on the balls of his feet, pushing more length in each time until it hit the back of Charles' throat, leaving a considerable portion outside.
Struggling to breathe, Charles wrapped his lips around the sizeable intruder and throated Ken to the best of his ability, applying one hand to Ken's hip for balance and the other to massage his enormous ball sack.
