Winner Takes All

Even though it was an eventual consequence of any fledgling nudist's experience, Gray never expected to be seen by any of his neighbors, especially the one whose bedroom window faced that of his office. It had only been a month since Gray began roaming around the apartment without clothing. Five years earlier, if anyone suggested such a thing, he would have called them crazy. Never in a million years would he have let it all hang out. But he couldn't be blamed. That's how Gray turned out, limited by the learned limitations of his Roman Catholic family, never very bold in his adolescent pursuit of the opposite sex, never comfortable about showering after gym class, and never having the kind of friends that had the kind of early experiences, money, and nerve it took to convince girls in school or at clubs to give up tag team blow jobs in public places, or perform sex acts to be viewed later on VHS tape.

However, there had finally occurred a shift in Gray's thinking. His confidence had grown. His trips to the gym had paid off, and thanks to the almost nightly work-out sessions he and his new fiancé' Clearice have been indulging in over the last three years, Gray had become expert in the fine art of mutually gratifying sex. He had steadily worked his way toward the freedom of sensuality he knew he deserved, introducing the tantric art to his love making, getting Clearice to involve variously sized dildos and vibrators in there foreplay, convincing Clearice to let him fuck her in the ass, and recording most of the events on their digital camera. Through one good turn deserving another, Gray had been loosened up, Clearice being the stimulus for that sensual shift in her lover's identity. Unlike Gray, she had experienced a healthy body concept formation and sensual identity, and so did not have the same sense of shame or fear. She had been comfortable enough to have driven across three states, and once played racquet ball, in the nude.

Clearice had for years, however, kept her distance from anal sex, the use of toys, and electronic exhibitionism. And just like anyone else, both Clearice and Gray either needed a special someone to help them to a new level of sensuality or they just wouldn't even tempt their personal breaking points. It had been she that Gray felt comfortable in inviting to insert multiple fingers in his anus, as detailed in the Tantric guide book he'd purchased from Barnes & Noble Online. Without Clearice, that never would have happened. Having performed the same method of orgasm extension for his fiancé', Gray decided that his next purchase, once he got Clearice's consent, would be a string of anal beads. Whether he'd entertain them being inserted up his own ass, remained to be seen.

Five weeks prior to when his neighbor had caught him beginning to enjoy his new nudist life style, Gray had begun surfing the web for answers to all his naturist questions. The very first question was how could anyone truly separate their sexuality, and understanding of sexuality, from their feelings of their own body, as well as from the bodies of others. As he linked from site to site, Gray couldn't even imagine how he would ever be able to stroll around a campsite in his birthday suit, not get an erection from studying all the women around the commune, or what he would do if some other naked guy tried to have a conversation with him. All he knew, up until that point, was that nakedness was either for sex (alone or in pairs) or bathing. What Gray learned was that anyone could be a nudist. All they had to do was get naked. You start small, local, and among friends, and then you find safe, accepting naturist communities. And if you got that far, all one needed to do was walk around with a towel, just in case you're feet got cold. Gray made his decision to start small after passing the "Do You Think You're A Nudist" quiz. Yes, he slept in the nude. Yes, he lounged in the nude with his partner. Yes, he went skinny-dipping once.

Gray took his one giant personal leap on Thursday, July 15, 2004. It was one of his days off from the head hunting job he had at Community Works. The average temperature for that month, and the lack of proper air conditioning, made it easy for him to get started. Gray made sure to lower the blinds in every room. Clearice tried to convince him that no one could see inside their apartment on bright sunny days, but he didn't buy that. On that first day, it was difficult for him to keep from getting aroused from the contours and textures of his own body. Even when his physique was less than ideal, Gray enjoyed playing with himself as much as the next person. With the nudity, his cock was always ready for the tugging. It was like a reflex, as if he was a member of that species of lower primate that have to be manipulating their own genitals or someone else's every minute of the day. By the second day, Gray had discovered that he could pump his cock to a point where he could use his pre-come as a very affective lubricant, which allowed for a generally superior jerk-off session.

Gradually, Gray gave himself more reminders to let go of his prick, and just let it be. Then there was the tingling he felt along the areas of his body that weren't normally exposed, from his shoulders, back, chest, and legs. It was strange at first, but it had gone away by the next week. In its place came another feeling. It was the first time that Gray had an understanding of why anyone would want to be naked all of the time. He began to revel in the feeling of a gentle breeze flowing against his chest, back, ass, balls, and cock. He began to especially enjoy the feeling in his sex as it bounced during his walks between rooms, and during his activity in the kitchen. Now, in a strange yet harmless way, he came to enjoy the feeling of kitchen counter edges, the backs of chairs, and the vibration of the washing machine or dishwasher against his cock. These feelings seldom led to erections, but were gratifying none the less. The new spirit Gray was adopting just plain felt good, and feeling good was enough.

It wasn't until the second week of his consistent effort that Gray began to generally ignore the parts of his body he normally tended to manipulate out of habit. This, he knew was key to any progress. By the third week, he had gone through the entire process of making Clearice dinner while wearing not even an apron. That was perhaps one of the greatest indicators of his success because the last thing Gray ever wanted near his food was anybody's exposed private parts. That evening, when Clearice came home from her job as an obstetric nurse's aid, Gray opened the door to reveal not only his nakedness, but a fully prepared meal waiting on the kitchen table. Clearice was so immediately inspired that she locked the door behind her, tossed her pocket book and keys aside, fell to her knees, and proceeded to suck Gray's cock. However, she took only his pre-seminal fluid as an appetizer. She loved Gray's cooking too much to let it get cold, and they knew he could hold out until it was time for them to share other less culinary morsels.

It was on Thursday of the fourth week that Gray got caught, or he could have perceived that he had earned himself his very own voyeur. He had been standing in the back bedroom, that he uses as his home office, and he was talking on the phone with a perspective client. Gray turned in time to realize almost instantaneously that he 1. forgot to lower the blinds, and 2. he was staring eye to eye with one of the more attractive women among the complex. She, the lady who lived in the unit across the courtyard, who was about Clearice's age of 27, stood at 5:'6, weighed around 120 pounds, wore her thick black hair long, had brown eyes, and creamy olive skin, was staring at him from her bedroom window. The woman had entered her bedroom, after having come home from work. Her routine was to feed the goldfish she kept in an enormous brandy snifter she placed on a desk that bordered her window. After tapping some flakes in the bowl, the woman peered upward, and began to smile. She had seen the man before, and had spoken to him on occasion. But she certainly never expected to see his naked body. She was warmed by his profile, the slope of his shoulders, the clear definition of his chest and abdomen, and the joyous surprise of seeing a beautiful strange man's sex as it gently swayed in the tow of his conversational gesticulations. As he turned to face her, she knew that the responsible, and respectable thing to do was meet his gaze.

Gray did not immediately move to cover himself. Upon reflection, he did not think it was because he had become bolder or more confident, but it was because she was beautifully transfixing, and because she seemed to have been viewing him from the perspective of polite spectator, rather than busy-body neighborhood spy. In that moment, Gray was as the proverbial deer caught in the headlights. As his shame urged him toward his senses, Gray began to slowly drop to his chair, and then turned to face it's back to the spectator. By the end of his phone conversation, Gray crawled from his office, into the bedroom, and proceeded to throw on some clothes. He then return to his office and drew the blinds, taking care not to make eye contact with the spectator. However, he did manage to see that she had waited around long enough to see his return.

Gray's goal ultimately was to be so comfortable with his body, that he and Clearice could go to nude beaches or colonies. However, getting caught immediately brought back past feelings of guilt and shame. He knew he deserved better than to have to struggle with such feelings, especially after coming so far. But there they were, so what they required was resolution. He was sure that he would be totally free of all the repression that had built up through the years, if he could just get passed being socially naked. Through his deliberation, Gray realized that he could also see the event of getting caught by a stranger as a learning opportunity, a stepping stone, a test of his resolve. Yet there was more to it than the turning of his and Clearice's lives into an Eden. There were his own feelings about the size of his penis in its flaccid state. If only, he thought, it was a couple inches longer,, and an inch thicker, I'd have nothing to be ashamed of. But then, when Gray thought of shame, he would recall the stigma associated with having an uncircumcised penis, and he would retreat again from his resolve. Yet now, having made such an investment in his freedom, Gray was less inclined to beat himself up, and commit entirely to a retreat from his ultimate goal.

That weekend, Gray and Clearice were in and out of the apartment, doing shopping or visiting friends and family. On the following Monday, Gray went to work, and then came home. Upon entering the apartment, he lowered all the blinds, and proceeded to undress. Inclined toward neatness, Gray hung his clothes, and tossed his socks in the hamper. He had stopped wearing underwear, having grown accustomed to the comfort fit he felt without their confinement. From the bedroom, he went to the kitchen to make his afternoon espresso. Upon its completion, Gray made his way to the back room. He placed his espresso by the computer, and then leaned toward the window, and peeked through a pair of blinds. He saw that there were no children playing in the courtyard, and that his neighbor's blinds were drawn. In that instant, he decided to allow some fresh air in.

Presently, he went about his business, checking e-mail, surfing for job hits, and taking notes for his clients. Within half an hour's time, he was so drawn into the zone of his work, that he did not notice that his neighbor had herself arrived home. Absently mindedly or purposefully, the neighbor could not tell, Gray stood from his chair, and boldly went about retrieving this or that from various places in his office. Subsequently, poised in a standing posture before the open window, Gray took a moment to retrieve the cup of coffee from his desk, and take a sip. Staring out the window, Gray saw that he was once again being seen by his neighbor. As she smiled and waved, this time with her hair tied back in a pony tail, and wearing a smart black dress suit, Gray quickly turned the back of his office chair so that it covered his sex. Not wishing to be rude, Gray waved in kind before turning his chair around, and lowering himself into its seat.

It's best not to make eye contact, he thought, firm in his resolve. Gray returned to reading his e-mails. The flush of his embarrassment gradually faded, and he was compelled to look in his neighbor's direction once more. He was mildly surprised to see that she had untied her hair, and changed into a lemon yellow tank top and tight red shorts. He wondered if she had done so with her blinds up or whether she had closed them temporarily. Gray then noticed the woman waving again, this time more insistently. Giving her his attention, Gray watched as she picked up a piece of printer paper from somewhere, and held it lengthwise in front of her chest. Upon it, written in thick black marker, were seven digits, a dash separating the first three from the last four. The woman's smile was beaming as she tilted her head slightly, and then pointed at herself. In response, Gray pointed at himself. With that, the woman shook her head in the affirmative. On his face, Gray wore an expression of mild amusement, which he tried to make more mild with what he hoped looked like indifference. However, on the inside, the message was: "Holy shit!!! I should not be calling this woman! What time is Clearice coming home!?! Okay. I've got five minutes." Gray allowed three more seconds of reluctance to pass, and then peered up at the woman's number once more before dialing it.

"Hello." she said.

"hi. Gray answered, Look, I'm really sorry about this. I just forgot to lower the blinds, and...and I have no business-"

"You know we've spoken, and I never got your name."

"Gray. What's yours?"

"who named you Gray?" She asked.

"Oh...it's just a nick name I got a long time ago. Long story. My birth name is Rudolph."

"Oh...then Gray it is. My name's Trisha."

"Yeah, look anyway, I'm sorry about-"

"Does your wife know that you run around your apartment naked all the time?"

"She's not my wife yet, and yes, she does."

"Really? Good. S...then would you do me a favor?"

"Uh...I guess. What is it?"

"Would you just like stand there, and jerk off for me?"

Up until that point, Gray and Trisha's eyes were locked. But with her question, Trisha had caused Gray to look in every other possible direction.

"uh...I don't think so." He said finally.

"why not? Trisha prodded, "It's not like your bride to be is home or as if you have company your not allowed to have over. Go ahead. Let me watch you masturbate."

"why should I?"

"Well...because it might feel good, good for different reasons than the usual."

"Good, how so?"

Gray leaned back into his chair, confident that Trisha could not see his swelling cock.

"Well...it might feel better if you do it while we stare into each other's eyes. And...if I like how it turns out, I might be inclined to do the same for you."

Gray stared into her brown eyes, and listened to her calm breathing on the phone. Who does this chick think she is, he thought. She probably thinks she's something. She definitely think she's something. She is.

"I have to go." Gray chose to say.

"Okay." Trisha answered, seeming to know that he would not yet hang up.

Still looking at Trisha with the phone cradled between his ear and left shoulder, Gray softly stroked his hard red cock with his right hand.

"I thought you were hanging up."

Trisha smiled, her eyes never leaving his.

"Tell me Gray...you've got to be pretty hard by now, huh?"

Gray released himself as his skin flushed nearly as red as his cock, and then looked away.

"Ah, I knew it."

"It was nice talking to you Trisha. Good-bye."

Gray smiled at Trisha, and returned the phone to it's cradle. He then turned around in his chair so that the back of it faced the open window. From it he then rose, and casually made his way into the bathroom, where he beat himself off to the fresh memory of Trisha's inspiring face and physique.

Gray returned, fully clothed in black jeans and a University of Massachusetts jersey, to his office on the next evening. He thought about sticking to his new mode of undress, as a show of unshaken security, to show her that he would not be intimidated. But upon second thought, he decided to keep some clothes on for the evening. If he spoke with her again, he could just explain it away by saying that he just got home from work, or he just plain felt chilly. That evening, Trisha's blinds were drawn. On the following Wednesday evening, Trisha's blinds were open, and Gray could see that she had a female guest over in her bedroom. Noticing him, Trisha smiled, and then lowered her blinds. His imagination running wild, Gray retreated to the living room, where Clearice lay naked on the couch watching TV, and proceeded to seduce her into a few hours of love making.

"Hey naked guy." Smiled Clearice as she parted her legs, "Oh, we're at half mast, are we? What dirty thoughts were you entertaining?"

Gray felt a twinge of guilt bubble in the pit of his stomach as he drew close to his lover, admiring the contours along her 5:'7 frame, the voluptuousness of her creamy white C cup breasts, her naturally copper brown hair, and alluring serpentine green eyes. Watching her, he realized the trust he felt, the honesty that inspired his proposal to marry her. she was one of his very best friends, but the only friend that was born with a vagina that fit him so like a glove that it was just plain uncanny, could suck him into such a frenzy that he would pass out from the orgasm, and take his cock in with such fervor that almost the entire apartment shook with their coupling

"I was thinking about eating some pussy." Gray whispered against Clearice's lips as they kissed.

"Well then please be my guest."

That Thursday was Gray's next day off. The sex he had the night before had certainly scratched the itch. Yet he continued to feel a remnant pang of desire radiating from his sex chokra. The desire, the craving he continued to feel, in spite of having creamed like a king through the royal, expert gripping of his queen's vaginal walls, was indicative of the yearning one might feel for what one cannot, should not, have. Gray gently caressed the shaft of his cock as he entered his office. It was after lunch, and he had made his second espresso of the day, and was drinking it as he caught up on some pleasure reading. The blinds were half drawn, and just the barest thought of Trisha being home and naked made his cock instantly swell to full capacity. Gray, while gently trailing the fingers of his right hand from his rust brown pubic hair, to his scrotum, and then up his warm shaft, peered through the blinds to see that Trisha was in deed at home.

Trisha was going about putting laundry away. Her hair was once again tied back, and she was dressed in a green blouse, and a pair of faded jeans, the knees of which were ripped and frayed. Gray wrestled with the notion of getting her attention. Trisha's blinds were open, but her window was down. He surveyed the courtyard, and saw no one. He drew back his blinds all the way, and then returned to his seat. Gray tried not to stare, but it was very difficult. It was making him crazy that Trisha had made him crazy, and that she was also home. Subsequently, after Gray had stared long enough, Trisha happened to look his way, match his gaze, and then smile warmly. They nodded an acknowledgement to one another, and Trisha resumed going about her domestic task.