Beginning the Journey Pt. 03


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 Anadolu Yakası Escort 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 Kartal Escort his ability, applying one hand to Ken’s hip for balance and the other to massage his enormous ball sack.

Minutes later, Ken found his voice and croaked, “I’m going to come, should I pull out? “

Charles shook his head no and sucked a little harder. Ken came hard with a roar that reverberated around the music studio. His oversized testicles spat out one of the biggest loads Charles had yet experienced, five or maybe six spurts that he struggled to swallow. When the pressure was too much to bear, Charles coughed out the excess, which spilt onto the timber floor.

“Sorry about that,” Said Charles, disappointed in himself.

Ken said nothing but looked serene as Charles carefully cleaned his cock. When the last vestige of orgasm subsided, Ken seemed awkward and embarrassed at what had transpired. Replacing the panties and pulling up his trousers, Ken ushered Charles to the sofa, and the two sat down.

“We have to talk about what just happened, Charles,” Whispered Ken, barely able to look directly at his young protégé, “I’m deeply sorry, but we shouldn’t have done that.”

The apologies gushed continually from the mature piano teacher, but Charles strenuously assured Ken that he enjoyed what had happened and wanted more of the same.

“I’d hate for your Gran to find out,” Ken said quietly, “After all, Helen’s not stupid and does know about my tastes.”

She knew about Charles’ tastes too, he thought, but then told Ken that while his Grandmother had dropped a subtle hint, he feigned disinterest but admitted his wank fantasies.

As they spoke, Charles gently rubbed Ken’s crotch again, and this time he returned Charles attentions.

“Are you sure about this?” Asked a swiftly relaxing Ken.

“I’ve never been surer,” Smiled Charles, whose cock had doubled in strength.

The two of them removed their trousers and stood facing each other, naked from the waist down. Ken complimented Charles on his impressive hardon, and they began caressing each other. It had only been several minutes since Ken exploded in Charles’ mouth, but he achieved a decent erection, a tribute to his apparent recharging skill.

Using his fingers, mouth and tongue, Charles put a lot of energy into giving Ken another climax but was unsuccessful on this occasion. Ken, though, used his years of experience to quickly bring Charles off, swallowing his deposit with practised ease.


Lessons continued for several months, and they were a mixture of piano and sex. During this time, Charles quizzed Ken about his wearing of female lingerie. Beneath Ken’s shirt was a lace bra that Charles discovered during an all naked session in the garden, which matched the panties.

“What’s the attraction?” Charles asked after a steamy session.

“It’s a fetish that makes me feel like a woman,” Answered Ken, chest heaving mightily, “You should try it.”

Charles would do anything to please Ken, grabbed the discarded panties on the grass, and wiggled into them.

Ken’s eyes grew wide, and his sizeable cock revived.

“That’s so sexy,” Ken moaned, and Charles agreed.

“Come here,” Motioned Ken, and he laid Charles on the grass.

Charles watched, amazed, as Ken laid in between his legs and massaged his face all over Charles’ lacy crotch, drooling like a dog and panting hard.

The feeling of the lace and Ken’s mouth was too much for Charles. He released his balls into the panties; Ken sucked it up as a man possessed. The image of that mature gent’s action had burned itself into Charles’ memory forever.

“I need to come,” Shuddered Ken, when he knelt on his haunches, his face covered in slime.

“Come on my face,” Squeaked Charles, basking in the glow of another climax.

With Ken rapidly deflating, Charles confessed that he enjoyed wearing female panties.

“Oh,” Said Ken, pleased with that admission, “I have an extensive collection that I’m Kartal Escort Bayan happy to show you.”

He took me upstairs to a bedroom and minutely described each piece in his collection; bras, panties, stockings, suspenders that ran the whole gamut of female fashion.

“What’s in this wardrobe?” Charles asked, pointing to the corner of the room.

Ken turned a shade of crimson and said that it housed another collection, but Charles was not ready for that yet.

“You started this,” Charles chided, “Besides, I can handle myself.”

“Yes,” Ken agreed, “I can see that.”

The two naked men walked over to the second wardrobe containing a selection of rubber and latex outfits, accessories and toys.

Ken explained that he occasionally hosts sex parties for men with fetishes for lingerie and latex.

“They are exhausting events,” Ken explained, “But everyone leaves satisfied and sore.”

“What do you do with this?” Asked Charles, picking up a huge rubber dildo, thinking no arse could take it.

“You’d be surprised what some guests will do,” Ken winked.

“Your cock is quite sufficient.”

“I’m amazed you can take it,” Ken smiled, “Many can’t.”

“Their loss.”

Charles replaced the giant rubber cock and felt that he was not sufficiently advanced in his journey of discovery to explore a latex fetish. Still, he wanted to experiment with sexy lingerie and walked back to that wardrobe.

“Will you dress me up in something sexy?” He asked Ken.

“I’d love to, but there’s nothing left in the tank.”

“Next time?”



The next lesson could not come around fast enough for Charles, who had purchased some lingerie items. He wore them at night when he cruised the bars seeking cocks to blow. The feeling of lace enhanced the experience of bringing strangers to climax. Afterwards, he would wrap the panties around his cock and jerk off to a thundering climax at home.

When they met, Ken forced Charles to complete the lesson before engaging in sex. Neither could focus on the music this day, but Ken somehow mustered the drive to finish despite Charles constantly flirting with him.

“Can I try some lingerie on, now?” Asked an eager Charles, his hardon driving him crazy.

“Let’s go,” Smiled Ken, whose bulge was very pronounced.

“What would you like to try?”

Charles immediately selected a pair of sheer stockings and suspenders.

“Good choice,” Choked Ken, “Get undressed then.”

Ken helped Charles dress in the sexy combination and then walked him in front of the mirror. The look and feel of the lingerie aroused a volcano of lust within Charles, and he screamed for Ken to fuck him.

“I will,” Breathed Ken, visibly ecstatic, “But first, I want to enhance the experience.”

Charles disappointedly snorted when Ken began removing the stockings, and the two of them walked to the bathroom.

Ken shaved Charles’ legs and crotch for the next hour or so before redressing him with the stockings. Charles’ hardon did not abate for a second under Ken’s practised hand.

“Feel better?” Asked Ken as he connected the straps to the stockings and ran his nails across Charles’s thighs.

“Oh my god, I’m so fucking turned on!” Shivered Charles, eager to get into the action.

“On more finishing touch,” Said Ken, retrieving a box from under the basin, “It won’t take a second.”

Rummaging through the box, he selected a small cylindrical stick. Ken made Charles stand up and face the vanity and expertly applied a thick coat of lipstick to Charles’ lips.

“There, that’s perfect,” Exclaimed a triumphant Ken, “Shall we make love?”

Charles wanted a savage ploughing with no mercy shown, but the more experienced of the two took his time and fucked Charles slowly on his bed. When it came time for the anal penetration, Charles was so relaxed that he readily accepted Ken’s engorged cock with little lubrication and no irritation. They came together, with Ken filling Charles’ expanded shitter so much that it overflowed. Charles coated his chest with thick bolts of boiling sperm. Without prompting, Ken used his practised hands to massage the goo over Charles’ chest, just as he imagined it after their first meeting. Another fantasy fulfilled and the start of a new life as Ken’s fuck doll.

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