Let the Spirit Lead Ch. 01

Andrew had sunk somewhere below rock bottom he felt. Life had become miserable. Nothing in his existence was going well. Keeping with the adage of Americans hitting the open road in times of tumult, he followed suit and packed some of the belongings he still owned. During his recent divorce, he'd acquiesced and signed over much of his net worth to his now former wife and beloved children. He love did them. He was the one who had done much of the damage now responsible for his current state.

The house was quiet and still. She was gone currently. Considering his willingness to leave her and the kids as much as possible, she had allowed him to pack his things from what was now her home and leave. He never fought any demands she made. In fact, Andrew had suggested additional considerations in the divorce proceedings. The damage was done and he would do all he could to make amends for his decisions in life. Including the support of his children and his now former wife. As he silently roamed the halls of a home he longer owned, his mind remembered happier times. He threw most of his suits and business attire into trash bags for her to take to the local thrift store. He didn't need them now that he was no longer a highly paid partner of again, what was his business.

Mostly done, he took a moment to consider anything he may have missed. Walking out to the garage, he saw his car sitting there. He would not be taking that, instead encouraging her to either sell it or keep it for of their kids when they were old enough to drive. He pulled the cord to the attic fold-down stairway and then climbed the treads into the recess above where the cars were parked in the three stall garage. His heart quickened and he felt an all too common tingling within himself. So many memories of climbing these steps into the insulated, often steamy and dusty space of the storage area. The place where he hid his private past time. The boxes of lingerie, breast forms, dildos and other items used for his secret pastime. They were still there. Taped up and clearly, albeit falsely labeled in order to conceal among the other boxes in storage. She never really knew. On the rare occasions maybe, usually when he was home alone or when traveling for work. Andrew loved these times. It was usually for just a few hours at a time. Hours where he was carefree, relaxed and could unwind from the stress of his job, the family and life in general. For those hours, he was not the father, the executive, the task master, whatever he had to be. He was Andrea.

On the exterior, he presented as a manly man. Rock solid in his commitment to all things normal for a man like him. But in his head, his thoughts and his feelings he was different. From his adolescent years, his first experience of sexual arousal came from the pages of the department store catalogs. Thick, weighty catalogs filled with hundreds of pages of fashion and home goods. These books were as thick as phonebooks and held an incredible secret that seemed ludicrous to him as a young boy: glorious images of women wearing lace, nylon, satin and spandex for anyone to see. These catalogs were everywhere in the days before and leading up to the internet. His mother and grandmothers had them in their homes usually all year long. And when he could, he would sneak one, usually into the bathroom or someplace private and marvel at the exquisite lingerie from the early 1990's. Couple that with his first pornographic experience of a neighborhood friends stolen magazines taken from his Dad's stash, a hairy bush mixed with lace and nylon and he was forever mesmerized by these images.

He picked up the boxes, each filled with his secret and began to carry them down the steep stairs and load them into his new vehicle. The van held a lot and would serve him well as he drove west. After loading the four boxes, he picked up what he called his grab bag. This was a simple, non-descript black bag containing all of his favorite items. His favorite Vanity Fair bras and panties, his Rago shaper and garter belts, several pairs of nylons, a large suction cup dildo and the handful of other essential items he wanted during business trips to create Andrea. These items made up the best of the best in his collection.

Finally done loading, he texted his wife he was finished. He would be leaving soon and she could return whenever she wanted. He asked that she hug the kids and let them know he loved them. He would return once he came to terms with his new normal and she was accepting of his presence again.

Three days later, he found himself in Iowa. He was staying in a small motel just off the highway. He had little direction, just a few places he wanted to go and see. One of the things he did keep in the divorce was his severance package. The company was mad as hell, but his contract stipulated a severance regardless of the terms of his departure. His ex-wife had agreed and he had more than enough to survive for at least several years he calculated living the way he was. He was trying to find himself again. Who knows, maybe even re-invent himself. He was young enough.

Several nights later, Andrew was tired and looking for a place to sleep in Colorado. Again, little direction to guide him other than the promptings of his soul. Let the spirit lead was the motto that was taped to the now slightly dusty dash of the van. He'd actually slept in the van several nights now in an effort to conserve cash, but always felt safer sleeping in a hotel or motel. He also appreciated the privacy of the curtains and lockable door to the room, a hot shower and when it was good enough, breakfast.

The entire experience so far was made significantly more fun by underdressing round the clock, indulging in his secret stress reliever. Underneath his male clothes of jeans, a comfortable pullover and down vest he wore what made him happy whenever he felt the urge or had the opportunity. Today, he was wearing something special and every bump in the road reminded him of it. Andrew had four breastform options in his collection. He always thought of them as small, large, extra-large and huge and he loved them all. Today he was wearing his extra-large ones. He knew he could never pass in the public world as Andrea. He had never tried nor really intended to. He'd considered it, but reality always prevented it. But he always tinted the windows of every car he owned for a reason. Driving around with breast forms in the light of the day was great fun. He even made sure to buy bras with stretchy shoulder straps therefore allowing the forms to bounce and jiggle as his body did more easily. Bumpy roads were always more fun when he could feel and pretend in his mind that the silicone boobs were real. So with the tinted windows shielding his identity and modesty, he drove down the interstate in a skin-tight, ribbed, white top feeling his breasts jiggle and move the way he imagined a woman's would. But his crossdressing wasn't limited to forms and bras despite bras being his favorite items. In fact, he figured he owned close to 80 bras alone. His collection contained so much more, straight from the images of those old, thick department store catalogs.

As he drove, he considered countless things. He knew the risks of being dressed the way he was and always kept a large coat on the passenger seat in case he was pulled over by police or had to make a stop. Underneath his jeans he wore his favorites (funny how habitual we all can be): Curvation brand gold, satin panties with a large, thick maxi-pad in the gusset, a pair of cheetah-print Vanity Fair Perfectly Yours Lace Nouveau Briefs over the satin ones and his favorite Rago 6-strap heavy-control garter-belt fastened to a pair of white thigh-high nylon stockings underneath the panties to allow him to pee. As he shifted in his seat, he could feel the thickness of the incontinence pads he favored between his legs, the tight straps of the garter and one more thing: the black butt plug he had worn a thousand times in his life that caused him to pretend like he was a real girl being fucked in the ass. Another odd habit he had developed in his life was to masturbate onto the maxi pads he kept in his collection. Over time, the cum stained pads would accumulate enough jizz to stain a certain color and become saturated enough to spike his fantasy of being gang-banged by a group of men, dressed in his favorite lingerie and of course, as Andrea, a real life woman. The cum would leak out of her cunt and her ass as she was fucked in both and she would have nothing else to do but to wear a thick pad to collect the jizz to avoid ruining her panties or her clothes.

Andrew fantasized about the cum leaking down her legs, her hair messed and her makeup running. Her stomach full of the yummy cum she swallowed as she was the center of a great bukkake session. His erection was strong as he continued to drive.

Underdressing as a woman for almost a week now, he reflexively adjusted the straps on his bra to the middle of his shoulder. Thinking to himself silently, this was exactly how he'd seen a million women do it and he hadn't even realized he reflexively did it exactly the same. He ground his ass against the seat of the van, pressing the plug deeper into his hole.

The bra was a perfect choice for today. The silicone nipples of the forms were visible through the unlined Vanity Fair bras he favorited. Since the company had stopped manufacturing the Satin Solutions full-figured bra, he had purchased as many as he could on ebay in all different sizes and colors to fit his different sized forms. Today, with the extra-large forms he was easily filling out the cups of the 42DDD bra he was wearing. And despite the bra and the ribbed, white sweater he was wearing (which greatly accentuated the fake boobs) the nipples were indeed showing. He pinched one and pretended it felt good enough to make his pussy wet.

Night was falling and his body ached from being in the car all day. Andrew searched his phone to find a nearby hotel. He had stayed in so many hotels in his life and on this road trip that he started to search for unique motels instead of the always-look-and-feel-the-same type corporate ones. He found one and was soon getting off the interstate to park and check-in. The Clark Motel was nothing special, almost dead and quite retro in its appearance. He reluctantly pulled up his sweater, removed the forms from his bra and then zipped up his coat. It was freezing outside! His real nipples hardened as he walked into the tiny lobby and checked in. Walking through the door, he worried as he often did, if anyone could tell he was wearing what he was under his clothes. Was the pad too thick that you could see a bulge in seat of his pants? Was he walking strange with the long pad between his legs or the plug stuffed up his ass?

As soon as the door was locked to his room, he immediately took off his thick down coat and re-inserted the forms into his bra. They were still warm having been warmed by his natural body heat from wearing them all day. After admiring his figure in the large mirror by the door, he decided a change was needed. Opening up one of the boxes from the attic, he found the bra he was looking for, a nude colored Fantasie Nicola bra in the same 42DDD size. He quickly changed his bra and put on a tight dress he owned with polka dots and a pair of heeled shoes he liked. He checked himself in the mirror again. Cupping his fake tits, he reached a hand down into his panties and stroked his clit, licking his lips like a pornstar as he did. He felt insatiably horny. Looking in the mirror, he knew his six-foot-frame, facial hair and man's haircut would never allow to him to pass, but in the safety of his little motel room, who cared? This was fantasy time for him. He had established long ago that when the lingerie went on, he was a perverted horny female named Andrea who longed to be fucked, suck cock and swallow cum. But when the clothes came off and especially after he orgasmed, he was back to normal, responsible and of course, male, Andrew.

But this was his time well, her time. Time to find himself and recover from the failed past of his life. So he hooked up his laptop to the room's television, connected to wifi and started a porn video he always loved of a woman being gang-banged, jizzed and peed on and went into the bathroom to lay out his supplies for the next hour or so of naughty fun.

He found the perfect spot, well two perfect spots. The first was part of the porcelain tub that would allow the suction cup of the 10" veined dildo she intended to use up her ass and the other perfectly aligned about four feet apart for the other dildo that would go into her mouth and spit roast her body between two large and long, silicone cocks. She took off both pairs of her panties looking at the accumulated mess in the maxi-pad wishing it was the cum from her last sexual rendezvous having leaked from her orifices. Leaving the garter belt and stockings on she replaced the panties with a control-top black thong which could easily be pulled aside to allow entry into her rear hole. Finally, she removed the little black butt plug and lubed herself up. Getting down onto her knees, she appreciated the vantage point she had created. The television, perfectly in view, was quietly playing the almost hour long video of the woman being fucked and used as a human toilet. She reached between her legs and guided the rear dildo to the opening of her ass. She whispered to herself and the non-existent fantasy men all around her in her mind:

"Fuck me baby, come on, fuck my little girly ass! I wanna drink and suck and swallow all of your cum!"

The dildo popped past the muscles of her hole. Having worn the plug all day and having done this almost exact routine almost every night, her opening was easily willing. Andrea closed her eyes. She savored the feeling as the cock slid deep into her body. The spot, which she had just created for this little bit of fun was confined at first before the rear cock was inside her. Now it was perfect as she wrapped her lips around the cock in front of her. The one in her mouth was thinner than the one in her ass and she had chosen it for just this reason. Andrea was trying to get the dildo to slide down her throat. Hours of practice, gaging herself and causing herself to tear up and worse had finally trained her throat to allow it to slide past where her tonsils would have been. And there she was. Another day of pent up sexual frustration and mental fantasy driving around America wishing she could masturbate to release. All day the pressure building and building. Her mind was beyond the normal perversion at this point. Despite being a heterosexual cross-dressing male and currently impaled on two silicone dicks, Andrew would have literally fucked anyone for the chance to become a real woman.

As she fucked herself back and forth on the two cocks, she recalled a frequent fantasy of hers involving a genie. The magical genie would allow her to become a real female of her choosing anytime she wanted on one condition: she had to fuck at least one man a day. Considering the awkwardness of asking a stranger to fuck you, this could be no small task and therefore would require her to lower her standards of clean men in order to maintain her female form. Like an inner-city crack whore sucking any cock for $5 to keep the drug habit going, hers was to get fucked for free to maintain a female body with real boobs and a wet cunt. It was incredibly degrading and therefore at this level of sexual arousal, awesome and fun.

Snapping out of her mental fantasy, she realized she was in a semi-real fantasy—fucking herself in both ends watching porn of another woman doing the same thing. The woman is pissed on and jizzed on all while being fucked and sucking anything put in her face. Her lingerie soaked in the fluids from the men in the room. Andrea never touched her cock but could feel the pressure and the familiar feeling within her building until she finally reached a delicious and leg shaking crescendo. The jizz leaked out her clit. Her head went back along with her eyes as she reveled in the ecstasy of the orgasm. Her knees went weak and she lay on the floor of the not-so-nice Clark Motel breathing heavily and wondering what sort of sexual acts had been performed here in no-name Colorado. Without thinking, she slurped up and licked the cum from the floor she had just shot, all while never using her hands and swallowed it down. Anal orgasms always trumped ones initiated by a hand or a device. Andrew had perfected them he felt.

Coming to and removing all of her lingerie, she slid into the hot bath she had started before all of this occurred. In the warm water, her mind turned to other things as she shaved her legs and body and played with her flaccid cock.

SEVERAL DAYS LATER

Crossing the border from Idaho into Oregon, Andrew enjoyed the scenery out his window. He was still underdressing but had opted for the small forms today and black bra to match. His small tits were fun and girly and were easily hidden as he stopped at scenic areas along the highway. He had opted for a tampon and thin panty liner today instead of a thick pad and black, firm-control girdle instead of panties. He didn't fully understand the need for menstrual products, it just added to the overall femininity of cross-dressing. For him, or perhaps her, it was about being a real woman as much as possible. Dressing in lingerie that not only appealed to his younger days' first experiences but also the straps and hooks and materials that in his youth had defined and made a woman just that, a woman. Thick maxi-pads and other feminine products did that for him. It was why he shaved his legs and body, except his face. He just enjoyed and appreciated the softer things. Wearing nylons with shaved legs felt heavenly. Big bras and panties just meant extra square inches of delicious fabric against his skin. And he believed firmly that a person's first sexual experience often dictated their fetishes for the rest of their life. Growing up in the 1980's and 1990's meant these styles, although no longer in fashion, were incredibly feminine. Women today wore padded, molded bras and tiny panties. Nothing secret or pretty. Today's lingerie was too utilitarian for his tastes and especially his fetishes. He figured the only lingerie from Victoria he owned was some vintage second-skin satin panties and a few of the same line of bras. He dreamed of the women who were actually feminine in his memories of the past.

Stopping for dinner at an old diner, he ordered his meal and ate in almost complete silence. The waitress was clearly older than him and thus he could tell what she was wearing under her dress. The slightly pointy cups of her bra hinting the nipple meant she was wearing something he would probably wear himself. Finishing and paying his bill he walked back to his van and checked his phone. No messages. For the first time, he started to feel lonely.

Searching the web in a browser he saw an ad for a nearby hotel. He clicked and rented a room for the night. In one of the reviews, someone had mentioned something about requesting one of the rooms above the 7th floor. Unsure what the reviewer meant, he drove to the address and walked into the lobby. In his head, he already had plans for Andrea tonight. He had decided to possibly venture out dressed, of course after dark. But with the high rise of the hotel, maybe just the balcony, assuming they had one? He knew the spirit was willing, but when reality was actually included, the flesh was weak.

Approaching the desk, he handed over his credit card and ID. Standard operating procedure for just about every hotel in the US. As the man behind the counter was typing, Andrew said:

"Can I have a room above the 7th floor?"