Michael's Exploration Continues

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Recent divorcee embraces his feminine side.
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The contents were now strewn on his bed. Michael decided to take a bath, and while the water was filling, he undressed, his mind filled with a compulsion to express his dark, unfulfilled feminine self. Naked, he walked with purpose to the cabinet that housed his shaving supplies, picked up a razor, some shaving cream and put them on the side of the bath. The water level was now sufficient for him to submerge himself if he so wished, but tonight he had other plans.

He climbed into the tub, and looked down at his hairy body. His cleansing was about to begin, and for a moment, he contemplated what he was about to do, his hardening cock appreciating the potential move. He picked up the shaving cream and squished a palm size ball of cream into his hand, and removing one leg from the steaming water, lathered it all up. His hand was shaking slightly, certainly from the excitement, as he picked up his razor and began to strip the hair from his left leg. It was not an easy thing to do. Although Michael was not a hairy man, he was also not blessed with a light coating of man fur either, so the sexual high he had been getting subsided somewhat as he wrestled with a job that became more of a slog than he anticipated.

"I am going to buy some Nair tomorrow," he thought, frustrated at the painfully slow progress. Midnight came and went, but finally he stepped out of the bath with legs so smooth, he barely remembered his own wife's legs feeling as soft.

He padded into the bedroom, and felt a tingling in his groin when he viewed the feminine lingerie lying on his bed. He picked up the black garter belt, and with a sharp intake of breath, he removed the tag, studied it for a moment, and then slipped it around his stomach.

He felt the straps of the garter belt occasionally caress ever so gently his legs, and his cock was gratefully filling with blood after every electric touch.

With his heart beating quickly, Michael picked up a pair of coffee stockings, and carefully opened the prize. He looked at the first stocking, as it draped in his hand, and he sat down on the bed, and pulled his knee to his chest.

It was as if he was starring in his own personal porno movie. He had dreamed of wearing stockings for so long, and now was the moment when he could experience one of his strongest fantasies, totally free of any disturbance or worry of being caught. He flexed his toes and pulled the stocking over his foot slowly. Its rasp as it enveloped his shaven leg caused his cock to twitch, and he felt like the prettiest woman in the world as he gently and gradually pulled the nylon up his hairless leg.

Right then, he felt almost complete. It was an indescribable moment. It was like that first time he had experienced an orgasm as a boy, sliding down that gym rope in PE, his cock inadvertently rubbing just enough to cause him almost to let go as he slid down, when that electricity in his groin had crescendoed so incredibly. Next, Michael focused on attaching the stocking to his new garter belt. The little button secured in each hole with the skill of a man who had dressed his wife countless times in the past, he was already an expert at this, and he adjusted the tautness of the straps, so he could feel their reassuring tug when he moved.

Very much a foot man, Michael curled his toes back and studied them in the stocking. He instantly wished he had nail polish in the house, but made his mind up to remedy that the following day.

In the hazy next five minutes, he repeated the process, until he was sitting on his bed, wearing nothing but a garter belt and coffee sandaltoe stockings, the biggest hard on he had ever had, and a smile that had been missing from his face for many months.

Like any person who wears stockings for the first time, he playfully slid one foot up and down the other leg, listening to the familiar rasp. He smiled to himself, knowing that he could now hear that arousing sound whenever he wanted, and realised that after all these years, he had secretly longed to be the one wearing the lingerie, not the one insisting on trussing his lovers up that way. As epiphanies go, this was his biggest, he thought.

He walked to the light switch on the wall next to the bathroom, and turned it off, sending the room into darkness.He adored the feel of the garter straps as they tugged on the stockings. He adored the sound his legs made whenever they touched, and he adored how he felt, how liberated he felt, knowing he was wearing his first nylons.

Moving the rest of the underwear to one side, he climbed into bed, and lay there silent and motionless for a full five minutes. his alarm clock showed that the witching hour had come and gone, and the number one at the front meant he was going to be grumpy getting out of bed in the morning.

But he didn't care. His left hand voluntarily made its way down to his crotch, and he spread his legs so he could find access to the most sensitive part of his body, his inner thighs and under his ball sack. His cock was already straining for release, and eyes closed, Michael traced his fingers in that dark, silent roon, all over the places that were screaming the most for his attention.

He continually flexed his toes upwards. He again contemplated for a second why he had insisted on all his lovers arching their toes back when he was about to come, and fixating on them as he released his seed. He did not have to ask anyone again to do that, as he could now look at his own toes whenever he wanted, nails as long and perfect as he preferred, always in the most perfect colour of nail polish, always dressed in the stockings he wanted, and wearing the shoes he felt were sexiest.

As these visions raced through his mind, many at a time, all competing for his attention, his left hand had subliminally started to drag itself up and down the length of his cock, and was now beginning to draw that familiar feeling from his loins.

As Michael came, he purposely brought his knees to his chest and focussed on his flexed toes in the subtle green light of his alarm clock. His semen shot up to his face, and matted in his chest hair. He could not remember a more powerful orgasm.

At that moment, he basked in the afterglow of the act, and without even thinking about it, brought his hand to his mouth and licked it, seeking his seed desperately.

His flaccid cock stirred, as he smelled the familiar ammonia aroma. He had not expected to want to taste his own come, but it was almost like sealing the deal. Instead of getting up to clean himself, Michael lay there for a good ten minutes, deciding to drift into sleep as he was, wearing his new undergarments, his chest flecked with traces of his powerful orgasm.

Seven AM comes around way to soon, some mornings. This was one of them, and Michael was exhausted when he woke, but his morning glory hard on was straining for mercy. He looked down at his stockinged legs through bleary eyes, and smiled. He was so horny, he felt he had to masturbate before moving. That first orgasm of the day cleared his head, and little did he know , but he had just created a new ritual for himself.

He slid the garter belt over his hips and peeled the stockings down, still attached, and then prepared himself for work. Shower, shave, shirt, pants, hair, tie, socks, shoes and teeth all done, the clock was his enemy as he strode out of the house to his car. He noticed the pants felt different. He felt more aware of his legs being touched than normal, and liked it.

Morning came and went, and then hunger set in. Michael normally asked for Janet to grab him something for lunch, but today, he had errands to run.

In the blur of a moment, Shoe World, open this time, was in front of him, and he was swinging open one of the tall front doors.

Womens shoes to the right, and Mens to the left.

Shoe World is a cavernous place. Even when there are lots of people shopping there, it seems empty. But there are varying degrees of empty, as Michael was about to discover. He headed to the aisle where the stiletto sandal types shoes were. All in a row. A long row. A long row with three or four women patrolling them. This store was not only not empty, it felt packed to him.

He tried casually ambling down the row, but was acutely aware that as the only man in the part of the store which was quite obviously where the sexiest of shoes were, he felt distinctly uncomfortable.

He was finding it hard to even look at the array of high heels, when a young female voice behind him interrupted his discomfort.

"Are you looking for something in particular, Sir?"Becky asked. A plump teen, name badge proudly displayed on her shirt introduced herself as his personal assistant for the day.

"Er, yes, Becky, I am trying to find some elegant shoes for my wife. We have a couple of cocktail parties coming up, and I wanted to surprise her, " Michael stammered.

"What size does she take?" Becky asked, innocently.

Michael immediately thought his intentions would be thrown right to the surface now, but vaguely hoped that his reply of size 9 would simply lead her to think he was married to an Amazonian woman.

"They need to have a four inch heel, stiletto, not wedge, be strappy and open toe, not too glitzy," he gabbled.

"She knows what she wants, doesn't she!" the helpful assistant smiled, as she guided her guest down the row. Strangely, Michael now did not feel remotely uncomfortable. To the world, he was no longer a closet transvestite or shoe fetishist, lurking, waiting to see some woman try on a pair of sexy shoes, or even worse, picking up hot heels that were obviously big enough to fit a sissy. No, he was being ably assisted in buying some hot shoes for his loved one, and now the envy of any lady who cared to notice, wishing their husbands were as attentive, and any guy that happened to see him was probably wishing they did not feel that uncomfortable that they could boldly go and pick some slutty heels for their own lovers.

The time flew by, and half an hour later, Michael was sitting in his car with four shoe boxes on the passenger seat in front. He could not wait to get them home!

He drove a short distance to a grocery store, and walked in. Oddly, buying nail polish, cotton balls, Nair and nail polish remover was more embarrassing to him than any of the other items he had purchased, but he pushed through the discomfort and left with five colours, all of which he could not wait to try. Blazing red, neon pink, a dark plum purple, navy blue and a candy apple red that advertised itself as being the shiniest Revlon made were now in his collection.

The remainder of the day dragged by as if the hands of the clock were wading through treacle. Finally, at a minute after seven, Michael was racing home.

When he pulled up to the house, he had butterflies like a child before Christmas, and did not even notice that he once again flew past his most recent best friend, Skyy's 1.75 liter bad boy, without even giving it so much as a hello.

Boxes everywhere, he stripped his clothes off down to his boxer shorts, and delved in to his bag of nail polish.

He settled on the "Right said Red" nail polish, and with that same swarm of butterflies in his stomach, made his way into the bathroom where the light was at its most bright.

Michael made himself comfortable on the side of the bath, and put his left foot up in front of him.

Again, the thoughts racing through his head were making him shake, but at the same time, it felt so right. He opened the small bottle, and then carefully applied the bright red polish to his big toe. For somebody who was put off by a woman who had even the tiniest chip in her nail polish, his quest for a self applied perfect pedicure was always going to be a big ask, especially the first time.

But being anal has its advantages as long as you have time on your side, and Michael did. He knew what he wanted to accomplish, and over an hour later, he was sitting admiring a near perfect pedicure. His nails, which he kept longer than most, looked perfect to him. He decided to continue to grow them out, as he wanted them to be longer and sexier, but for now, they looked amazing to him.

He could not help but flex his toes over and over, and was ridiculously excited to see what they would look like encased in a pair of stockings, wearing a pair of the sexy shoes he had purchased earlier.

An amateur makes many mistakes, and Michael's transition to a feminine alter self was not going to be plain sailing. His impatience to see his toes through some barely black stockings led him to smudguing his first pedicure, and having to peel the stockings off his toes. "Damn it! How long does this shit take to dry?" he cursed, having now ruined two stockings, and having to put a new set of polish on.

Patience is a virtue though, and within an hour, his beautiful toes were flexing and arching inside a pair of nude, sandal toe nylons.

His cock was once again straining , begging for release, but the main event, his shoe modelling, was still to come. He decided on a pair of four inch stiletto mules, black, non glossy leather, with a narrow strap across the toe.

As he slid his stocking clad foot into the first slide, the leather creaked, and he found the sound unbelievably arousing.....so much so, that he removed and place his foot into the shoe another three times, slowly, admiring how his bright red toenails looked in their stockings, perfectly framed by one of the sexiest shoes he had ever seen. And he was wearing them............

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4 Comments
lingerie65lingerie65over 6 years ago
Our first explorations' are ones of wonder and beauty.

I truly enjoyed this story so full of anticipation, & personal discovery. Our first times of wearing lingerie are unforgettable, I remember what happened the day when I discovered my first set of satin & lace black panties belonging to Rosita, and just how special & pretty I felt. How I turned into a pretty girl every time when I would slip into femininity by putting on all six of my cousins lingerie on..

AnonymousAnonymousabout 10 years ago
please continue

Please continue with this story. I'd like to read about how he hooks up with hot hung hunks who feed him cock and then fuck him while dressed in his sexy clothes.

BimboBambiBimboBambiover 11 years ago
please continue

I completely love the realism. It isn't easy to transform and the writing style of complete and total description is great.

sally_spandexcdsally_spandexcdover 11 years ago
great start

my clit was swell from the time he started shaving,,,,hurry up

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