First Time - Ken becomes Kendra

Gay
2006-05-01

Unsure, but excited by realizing his long secret fantasy, not wanting to disappoint and captivated by the attention being paid to his crotch, Ken raised up on his tiptoes as high as he could manage. He stood that way for some time, glancing down at the darker reinforced nylon covering his toes. Momentarily the nerdy young man caressed Ken's nylon covered buttocks. Having his bottom fondled sent wave of excited embarrassment through him. He reached down to push Brent's hand away. Instead Ken found his own hand being pushed away. "That's a good girl," Brent said as Ken put his hands uncertainly in front of himself. The younger man's hand then wandered unhindered over Ken's nylon covered bottom. How could he feel so humiliated and his cock be so hard at the same time? Then then the hand wrapped fully around his cock, stretching the top of his pantyhose as it did. This time the voice was more demanding, "Time for your 'cock walk', hon. And stay up on those tiptoes. . . all the way up. "Ken's excitement overcame his uncertainty, and with Brent's hand firmly grasping his nylon covered member, he was led around the room on his tiptoes several times by the smaller man. At the man's direction he took little steps.

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  . . sissy steps. Then the young geek stopped, leaving him standing on his tip toes, dressed in pantyhose and sweater, his erection in full view. Brent Halloway was incredibly excited by what he was doing, initiating this handsome, pantyhose clad closet dresser whom he had just recently met. Ken Turner was obviously a ladies' dreamboat. This Adonis just happened to have a little 'quirky urge' in his psyche. Brent smiled as he remembered the flash of nylon covered ankle that had led to his carefully staged introduction. He had laughed off the first derogatory rebuff with a friendly smile and firm retort, "Nice ankles. " Ingoring being called a 'little runt' while seating himself on the adjacent barstool, he had begun the conversation, drawing out the larger man's secret - curosities which had shaped themselves into unfulfilled desires. Brent was used to a lifetime of being called twerp, pee wee, shrimp, pipsqueak so the thought of a 'turning of the tables' had been an objective worthy of pursuit. The slight-bodied man restrained his own pent up desire for release. Now was the time to proceed carefully. . .

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  to shape his new companion's initiation so that his surpressed feminine desires were released. He wanted the egotistical 'hunk' to learn first hand how it felt to want to please this pipsqueak. The office boy turned maestro reached down and adjusted the front of his new acquaintance's pantyhose so the front was lowered just enough to stretch under his cock and balls. Still on his nylon covered tiptoes, Ken was led by his cock to the couch and they sat side by side. Even as he rubbed the nylon covered thigh, Brent could sense the remaining uncertainties coming to the surface. Ken spoke, "I. . . I think maybe this is enough. . . for now. I-I have to. . .

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  " His voice was hoarse. "Just relax and enjoy, honey," said the smaller man as he stroked the exposed penis, still hard. There was no denying the fluid which had seeped from its tip. With his cock once again feeling that magical touch, Ken remained seated on his nylon covered bottom on the couch. His excitement overcame his uncertainty. "Just close your eyes a moment. Relax and enjoy. "He closed his eyes, his longing for sexual release overcoming his anxiety. His nylon covered legs flexed as his excitement grew. The shrimp had the big guy panting like a puppy for more. Brent smiled. . . the former 'big man on campus' had quickly become a big girly cock!"Slide forward. .

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  . put your weight on your tiptoes. " Ken slid his nylon covered bottom forward toward the front of the seat cushion and positioned his legs so only his tiptoes touched the floor. Once again he closed his eyes. Having his cock stroked while he balanced delicately on his nylon covered bottom and tiptoes was so incredibly erotic. One hand was stroking his cock while the other was fingering the slimy pre-cum on the tip of his erect penis. Then the mousey young man leaned closer and slid a finger into his mouth. Ken's eyes opened in surprise. "Just enjoy the finger," he was told. "Suck it like a good girl. You are my good girl aren't you, hon?"Feeling the urge building in his cock, Ken ignored the heat in his cheeks caused by the humiliating remark, not to mention the salty taste of his own seeping fluid. He only nodded as he let the juice coated finger slide in and out of his mouth. Watching the pantyhose clad ladies' man, balancing delicately and sucking a finger while having his cock stroked, Brent knew the time was now. He took Ken's hand and moved it so it replaced his own on the exposed cock. "Stroke yourself.

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  . . and suck my finger cock," he said. The pantyhose clad man did as he was requested. "Mmmmm. . . . look at my finger sucker stroking herself. Keep stroking yourself and suck my finger. . . my finger cock. Make it nice and juicy for me. " Brent ran his hands over Ken's nylon covered thighs and exposed front.

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  The pantyhosed man did as he was told. His mouth filled with saliva. The the smaller man slowly withdrew is finger and said, "Look at me. . . "Ken watched as the young man who he had considered a nerdy runt lowered his own zipper and exposed his own large, erect cock. "Time to go from your tiptoes to your knees my pantyhosed pretty. Slide down on your lovely nylon covered knees for me, hon," he said. The man in pantyhose slid off the couch and came to rest on his nylon covered knees. He continued stroking himself as he opened his mouth to the smaller man's newly exposed cock. His initiation had begun in earnest. As his head bobbed uncertainly on the hard cock, Ken's mind was awhirl with conflicting emotions and confused thoughts. One thing was certain though. . .

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  the cock on which he was sucking was considerably large than his own. In that department it was he who was the pipsqueak!Part TwoWhen they next met after that first night, Ken's denial and macho rebuff were met with an stinging reply. Embarrassed, he apologized and soon a package of pantyhose were given to him. Later that night he excitedly kneeled and offered oral homage to his twerpy acquaintance's large cock. . . . ********It was almost a week before Ken Turner mustered up the courage to return to his favorite night spot. The events of the prior week had left him quite uncomfortable even though he tried to erase them from his mind. Why, he had kept asking himself, had he given in to his urge and worn the pantyhose out in public? As he entered the lounge, he felt a little nervous, almost guilty inside but he had to put his mistake behind him. The lounge was quite dimly lit and not particularly crowded. Ken glanced at one of the available tables, but walked to a tall stool on the far side of the bar. A wall was close behind the short row of stools. The effect was to place him in a sort of alcove. He climbed up on the stool and ordered a beer.

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  . . and then another. He was lost in his own thoughts when he noticed movement next to him. He looked up. Brent Halloway stood next to him. He did not sit on the available stool. His position afforded him an unblocked view of Ken. He stood between him and the area where a few customers sat between a number of empty tables, each with a flickering light in the center of it. "Hi, stranger," Brent said cheerfully. Ken was ready. He turned to face the smallish man next to him. "Buzz off, shrimp," he said in a harsh tone of voice. "And hear this you little twerp. I want you to just forget about last week.

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   I already have.

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Like nothing happened. . . and if anything did. . . it was a mistake. . . liquor, whatever. You keep your nerdy mouth shut. . . or else.

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   Got it?"Brent looked momentarily taken aback, but smirked as he said, "Got it? Yes, I got it. Got it last week in fact. . . from you my princess in pantyhose. Oh, I'll keep my mouth shut. . . if you stop with the tough guy act. You just remember who the real big dick is between us! The dick you sucked. . . You and little pinkie got that?"Then it was Ken who was taken aback. He face turned red at the mention of his inferior manhood. "Okay, sorry.

 

   It's just. . . forget it. "Brent ordered a beer and the two drank in silence until Brent spoke, "Wearing tonight. . . pantyhose I mean?""No, didn't you hear what said!" Ken nearly shouted. Then he softened his tone, "Sorry. ""Sure I did, but look what I brought along just for you. . . " Ken felt something in his lap. Brent was holding a package of pantyhose. "Just the kind you like, reinforced top and toe.

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  . . . and a nice shade of taupe. "The seated man couldn't help himself as he felt his own erection forming. Brent moved his hand over Ken's crotch area and felt it, too. He smiled and gave a quick squeeze. "My, is your little dicky all excited? I'll bet it wants to feel that smooth nylon. Here, go put on your nice pantyhose. . . like a good girl. I just know that your little nubbin wants to be covered in nylon. "Ken felt the package of pantyhose being put in his hand. Given his excited state, he could not deny that his urge was real.

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   For little runt of a man, Brent Halloway seemed so forceful. And he could also not get the stinging insults of his cock size out of his mind. The effect of the beers he had consumed helped as well. Ken adjusted himself so he could walk, crammed the package into his pocket and walked to the men's room. Minutes passed and then he came walking back across the room. He climbed up on the bar stool adusting the pantyhose under his slacks as he did. He shifted on the low backed stool seeking to find a more comfortable position. He crossed one leg over the other. Brent ran his hand up Ken's pants over his nylon covered leg from just below his knee to almost his crotch. The material of his slacks slid easily on the nylon surface beneath. Ken stiffened but did not resist. Momentarily the slight-figured man rested his hand firmly on the larger man's thigh and looked deep into his eyes. Ken dropped his head and averted his piercing gaze. Satisfied, Brent indicated to him that he should listen carefully to his instructions. An hour later wearing shirt and pantyhose, Ken was on his nylon covered knees in front of the pipsqueak nerd.

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   He watched the short-statured man expose his massive sized cock. "The boss wants to see you," he smiled. After the pantyhosed Adonis acknowledged the tiny stature of his own cock, he asked dutifully for permission to suck 'the boss' while he stroked 'little pinkie'. That night marked the beginning of Ken Turner's continued 'shaping' under the exciting, though always demanding manipulations of his slight-bodied acquaintance. Every few weeks thereafter, he found himself on his pantyhose covered knees servicing the diminutive young man. He learned to verbalize the inferority of his smallish 'pinkie cock' to the large cock he regularly sucked. Pieces of lingerie were added to his wardrobe. A pair of high-heeled pumps waited in the closet. 'Kendra' became a regular form of address to him. The beginningAs he waited alone, Ken let his mind wander back over the events that had brought him to this position. . . From early on he had had an interest in women's lingerie, stockings, etc. Nothing excited him more than to see a woman dressed in her lingerie, nylons and high heels. One evening in his girlfriend's bedroom his then girlfriend had noticed Ken idly holding a pair of her pantyhose, examining the color by inserting his hand inside.

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  "Do you like my pantyhose," she had said teasingly. "Uh, yes," Ken had replied, coloring a bit. "That is the color, I mean. Isn't this called nutmeg or something?His girfriend had wondered at his remark as she continued, "I've already got a pair of pantyhose on me. Put them on your feet, then you can see the color for real. Here, let me help you. It'll be fun. "Ken had been seated on the edge of the bed dressed in his underwear, his girlfriend in her lingerie and pantyhose was trying to decide which dress to wear. Playfully, she took the pantyhose from Ken, rolled them down and then leg by leg pulled them over his feet. Ken was a little embarrassed, but went along. Together they had worked the sleek garment up Ken's legs. He stood up and the darker top portion was pulled up over his briefs, wadding them up somewhat. "I don't think your underwear is made to be worn under pantyhose," she had said as he tugged the nylon material in place. It was then that the couple made the same discovery. Ken had become erect.

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   Pre-cum seeped beneath the darker top of the pantyhose. He tried to adjust his underwear, coloring more. He had become turned on by the mere act of putting on the gauzy women's pantyhose. "My, my, it looks like little Ken likes wearing pantyhose," his girlfriend had said with a mixture of surprise, curiosity and uncertainty. She put her hand on his crotch and rubbed his cock through the front of the pantyhose. They kissed and made love on the spot. Several days later, the curious couple had repeated the activity. This time she had given Ken a pair of her own panties to wear under the hosiery. Ken was erect before the pantyhose were even pulled up. His girfriend decided that they would wait a while for any sex.

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Ken had pulled on a pair of jeans over the pantyhose and spent the evening with them on. And so it had continued. Each time seemed to take one step further. His girlfriend was filled with a sense of experimentation and a curious sense of power. Ken, although he didn't admit it, was feeling a growing sense of urge to be submissive to his girlfriend while in feminine dress.

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  "It seems to relax me," he said. It also obviously stimulated him. Having learned of Ken's 'beginnings', Brent decided that he needed to know just how far this 'feminine submissive side' of Ken extended. He continued to expand his horizons. First it was panties and pantyhose under a pair of jeans or slacks. Then a lace trimmed, nylon camisole top replaced the shirt. He bought Ken a pair of high-heeled pumps to wear. Then a delicate women's nylon blouse was added. The demaning office boy took particular delight in fondling the larger man's nylon covered buttocks. He could see the embarrassment in Ken's eyes as he endured the groping, much as he had groped many a well-rounded, skirt clad female bottom. It was particularly humiliating when he had to wiggle his pantyhose covered bottom for Brent's amusement. Ken was an average sized man, and he was significantly bigger than Brent. One day Brent happened on a skirt which had looked to be about right. That night the skirt was added to Ken's outfit. He spent the evening dressed in panties, pantyhose, camisole top, skirt and the pumps.

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  Several weeks later, another break-through. Brent showed him a lacy white brassiere with underwired and well-padded cups. Ken protested, but once he was stripped to his panties and pantyhose, he put his arms in the straps, and allowed Brent to adjust them and fasten the back clasp. Being 'brassiered' was a defining moment. The lacy bra was the first garment that had no function other than to accentuate feminity. Wearing it was an overt admission of his submissive feminine side. A nylon blouse was added and tucked into the skirt, which fit snuggly on his nylon covered hips. Ken modeled in the mirror for himself and Brent. Brent then seated him and applied a little color to his cheeks, put lipstick on his lips, fluffed up his full head of hair and added a pair of small clip on earrings. "There, that's much better!"Ken slipped the high-heeled pumps on his nylon covered feet and spent the evening fully clothed as a submissive woman for the first time. "I'm going to call you, Kendra," Brent had said matter-of-factly. Ken blushed but nodded. That night the new 'woman' did the dishes and tidied-up for the first time. Brent discovered that 'Kendra' had definite tastes in clothing - stylish yet conservative done tasteful colors. He bought Ken a pair of dark brown leather high-heeled pumps.

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   When he stepped into them. Ken's feeling of submission had never been stronger. It took several days, but he learned to walk in the heels naturally. As Brent continued to get enthralled by the power he felt when Ken gave in to his urge to become submissive, he began to take on a more demanding dominant role - at least while he had Ken in his petticoat state. Asking Kendra to address him as 'sir' seemed a natural thing to do. Ken balked at first, then dutifully mouthed, "Yes, Sir. " It became more natural as the weeks went by. Of course Kendra was required to pay homage to 'the boss' on each visit. It was the young office boy who controlled the agenda in their noctural meetings. Being allowed to dress fully in feminine apparel was reserved as a special treat - for when Ken had been an especially good 'boi'. Most of the time Brent kept Ken in the nether state of male outer ware and feminine undergarments and pantyhose. Getting himself off while being submissive as a pseudo-female seemed to be the periodic undeniable desire of the otherwise normal Ken Turner. Another Night. . .

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  A few weeks had passed and Ken's desire had returned. He had resisted it for almost a month but the lure of forbidden excitement was too much to pass up. He dressed as he had 'promised' Brent the last time they had been together. . . the last time he had been on his nylon covered knees paying homage to 'the boss'. For whatever reason, the dimunitive office clerk had his number. Big Ken was going to have another 'Kendra' night. He looked normal enough in an open collared dress shirt, blue jeans and loafers. Beneath his outer clothes, however he was wearing a pair of lace trimmed tap pants, coffee colored pantyhose and feminine camisole top. Both the tap pants and camisole were white nylon. As he walked into the club Ken was conscious of the faint swish of nylon against his jeans. He looked down quickly to make sure that his jeans were covering his nylon covered ankles above his loafers as well as possible. He had only been to this club a couple of times, with Brent, and he knew it catered to a rather avant-guarde crowd of both men and women. Walking towards the rear of the club he saw Brent motion to him from a booth.

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   He walked over and slid in. Ken really wished that they could just leave and go play in private. He did not like being out and about in public when he was dressed and vulnerable. The waitress came by and Brent ordered two beers. Then he turned to the larger man at his side and said, "Good to see you, Kendra. The boss has missed you. Tell me what you are wearing. ""Please don't call me that, in public, I mean. " Brent just smiled and patted his thigh. Ken cleared his throat and then continued, "Tap pants, pantyhose and a camisole top. White and coffee. Okay?" Even as he spoke the combination of his words and the hand now on the front of his jeans caused his excitement to grow. Just then someone slid into the booth on the other side of Ken. He looked over in surprise. A young Asian man had seated himself on the opposite side of Ken from Brent.

 

   Ken looked at the young man, Japanese he guessed. He then looked at Brent. Before the concerned larger man could speak, Brent spoke, "Hi, Toshi. Ken meet Toshi. . . Toshi this is Ken. "An hour later Ken Turner, wearing tap pants, pantyhose, a camisole top and high-heeled pumps knelt in front of Toshi's exposed yellow cock, a surprisingly large yellow cock. The Japanese youth patted his head as he teased, "That's right, pretty white man. Be on your nylon knees like good girl. Show me you can be a good sissy boy for my yellow cock!"Ken was on his nylon knees, only the top of his pantyhose had been lowered to his thighs. Toshi had threatened his virgin 'womanhood' if Ken didn't please the yellow dragon. There was no need to worry. That night Kendra sucked yellow cock, and sucked it deep. A yellow finger inserted in his rear had gained Ken's full attention.

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   Better to swallow the yellow cum than get a bottom full of it the confused Kenra had reasoned. .