Fear of the Known

Ron Worthington sat on the front porch of his newly purchased 1920s arts and crafts bungalow facing Baynard Park in the Bellemeade section of Evansville, Indiana, lonely, bored, and thinking "what now?" A handsome young man passed by on the walk out by the street and smiled at him. He thought that maybe it was a smile of interest. He smiled back, but he held back, not wanting to hold back. He wanted to respond more, but this was where he had arrived in life, based on what he himself had done. A whirlwind of activity and momentous decisions had gotten him here, and now that he was here, he had no idea where to go and what to do to get himself out of this feeling of loneliness and the fear of what others knew about him and what they would do--how they would take advantage of him or scorn him.

Ron's curse--when he was a nearly invisible insurance company actuary in a big Chicago firm, nice enough looking at twenty-seven, but just one of a crowd of people sitting in cubicles and crunching numbers all day with little to do at night--was in winning $10.2 million in the lottery. Twenty-four hours of euphoria and "I can do this and that" and the reality started to set in. Suddenly everyone around him at the Chicago firm was his friend and wanted a piece of him. Both women, and more appropriate for him, men, who hadn't seen or responded to his sexual yearnings before now wanted to seduce and bed him. And they wanted to share what the lottery had given him. He briefly went that route but never with good results. It was overwhelming and fostered the fear of what they now knew and how low they were willing to go to get at his money.

He quit his job and barricaded himself in his apartment. But it wasn't enough. Everyone wanted a piece of him; everyone did what they could to get to him. Some even discovered he'd been a "look and dream but don't touch" closeted gay--and not just gay but obsessed with the image of being a woman for a man--and had approached that vulnerability, seduced and slept with him, and broken his heart when he found out what they really were after.

He wanted to be a woman for a man--to be covered and taken in the woman bits by a man.

He had gotten a taste of what could be but beyond having shattered his trust in the motives of others, it had also shattered his fantasies of how fulfilling his desire to be the woman with a man could be while still functionally being a man.

The lottery money enabled him to be anything he wanted, though, anywhere he wanted. He wasn't stuck in the known--what others knew about him and used to fleece him. He didn't have to remain in Chicago. He could go anywhere. He could keep himself hidden.

So, he did leave Chicago. And he took the major step of going to Italy--to a sex change clinic. To a clinic that appreciated the sexual goals a guy would want to have in becoming a woman. The clinic specialized in giving what was wanted to the max in a transformation. At great cost, but of little effect on what he had won, he took the total package, the complete transformation from male to female--the perfect breasts, g-spots, and vagina for sexual satisfaction--while retaining the ability to dress male and show that persona to the world in public. He paid for the deluxe package, designed for those in the sex trade. He had no intention going into the sex trade, but he had the money and he wanted the best job of it. He wanted total satisfaction from having a handsome hunk of a man put his hands on his breasts and his thick, long shaft inside him.

Already having a slim figure and somewhat effeminate mannerisms, he acquired firm breasts that could pass as either male or female, given the clothing choices, with new, puffy, highly sensitive nipples that gave both partners an extra charge when manipulated. And he acquired lady bits below, his penis transformed into a clit at the top of the vagina, a vagina with a deep reach topped with a highly sensitive G spot and with muscles in the channel walls that would stretch and were trained to undulate over a possessing shaft. Another G-spot area was provided high up into his vaginal tract to provide him additional pleasure from a man who could reach it. He would know when a man was taking him totally.

He'd gotten the full treatment that the Italian clinic was noted for providing for professional women of the night and mistresses of billionaires.

And then what? He hadn't come back to Chicago. In seeking anonymity and in more than slight fear for how extreme he'd gone, he'd picked a dull, conservative town, nearly just by throwing a dart at a map, and had wound up in Evansville, Indiana. He hadn't thought this through. He knew no one here. He had no idea how even to meet anyone here who could make his fantasy come alive of finding a man for his newly acquired sexy female. He never was brave enough to go out on the town as a female or have any idea of how to attract a man, especially a man who would appreciate and be turned on by the androgenous person Ron, thinking of himself as Ronda in his female persona, had become at high expense.

And wouldn't it be just like Chicago? Wouldn't any man who suspected what Ron now was and what he wanted also be able to discover how much Ron was worth and would scheme to get at that for himself, falsely representing what he wanted from Ron--what he wanted them to have together?

With a sigh, he came off the porch and walked to the Nichelson's big-box grocery store a couple of blocks north on Lincoln Avenue. He only needed a few items. He lived alone--the loneliness of living alone. He needed to keep his androgenous willowy figure, so he ate like a bird. His needs were few. That, of course, was a lie. His need was great. He just didn't know how to fulfill his need. He hadn't thought this through.

He was taken aback in the grocery store as he was checking out. The checkout clerk was the handsome young man who had passed by his house earlier and smiled at him. He smiled at him now too, as he checked Ron's purchases through the scanner. It was more obvious now, from how he smiled, that the young guy had a special interest in Ron.

He was gorgeous--tall, solidly built, blond, blue eyes, great smile, sex on a stick in Ron's view. He had to be in his early twenties. Probably a student at the nearby University of Evansville, trying to put himself through college. Ron bet he'd do anything to get at Ron's money. Ron bet he'd even pretend to be Ron's special friend. He'd already been through that in Chicago, before he'd done the full transformation. It was even more unlikely, Ron thought, that such a hunk would be interested in a guy who had done the full transformation. He'd have his pick of young women--or men, if that was how he swung--at the university. That was something else Ron hadn't thought about before he did it. He'd rushed into it thinking only of what turned him on, not whether guys he wanted would be turned on to fucking a male-to-female trans.

Ron leaned over to look at the young man's name tag. It said "Billy N." The young man started to say something to Ron, but he pulled back, seeing that Ron was defensively shutting down. His smile as Ron's purchases were bagged was more reserved. Ron nodded back and left the store.

That night, longing for connection and disgusted with himself for having become a hermit and wasting what he'd paid big bucks for, he went on the Internet. He knew the possibility of hooking up with someone who wanted to do a full trans casually, with little chance of knowing more about Ron and trying to fleece him, was close to nil. But if he didn't at least check it out, it would remain less than nil. He'd remain an unfulfilled hermit in his nice bungalow facing Baynard Park in do-nothing Evansville forever.

He was shocked and trembling when he found it on a regional gay hookup site. The photo on the dating and escort site was of a great-looking dark, beefed up, and sultry-looking guy claiming to be a football player at the University of Evansville. He was offering to be a paid escort for a fully transformed T-girl in the Evansville area who was no more than thirty. Send nude photo. Casual contact only; no strings attached. A fee was listed. It was high, but it wasn't high in terms of Ron's budget--or of his need. It was a real surprise and shock to see the fully transformed T-girl element explicitly spelled out.

He'd had "a year after" photos made at the Italian clinic months after he'd had the surgery done, when the marks from that no longer showed. With trembling fingers, he sent two of them. An hour later, "Brad" had responded, suggesting a hookup, and asking Ron if he had a Paypal account.

* * * *

The session, and, although it had its moments, it was clinical enough to be called a session, with Brad was straightforward. It relieved the need Ron had for release, but it left him wanting more. In wanting more, though, it served the purpose of lessening his defenses about getting on with a trans sex life. It did make a difference that he was paying for it, but paying was no burden for him--it just took the edge off the arousal of it--it didn't include the element of the other man demonstrating wanting him. To counter that, it meant it was the other man's assignment to satisfy Ron.

He answered the door as a she, Ronda, dressed in a sky-blue wrap dress. Brad, all hunky football star, was in a droopy T-shirt, showing off bulging biceps and beefy pecs, athletic shorts, and sandals. He was showing that sex was the goal from the outset.

In the foyer, shutting the front door behind him as he followed Ronda into the house, Brad got right to it. "Let's see what we're working with--how accurate the photos you sent me were." He reached out, undid the sash of the wrap dress, and pulled it off Ronda's shoulders, letting it cascade to the floor. She was wearing red lace panties and a bra underneath, with red spike heels on her feet. She was slender but had curves where a woman should have them. The bra pushed her breasts up, puffy nipples pressing into the material.

"Very nice," Brad murmured. "You're a real cutie. I don't really understand why you need to advertise and pay for it."

"I haven't been in Evansville long," Ronda said. "I didn't have any idea how I could hook up here--for what I want. For what I am."

"We have some interest in T-girls here. These quiet towns often have a kinky underseam. I can hook you up. Let's see more of you, though. Strip down. Let's see how good the surgeon's work was. Holy moly, that's a beautiful job. Where'd you get the great tits and the puffy-folds cunt? Dressed, you can go either way and be a smash hit, can't you?"

"Italy. A clinic on Lake Como. They specialize in work for the sex trade."

"Must have cost you a fortune."

Ronda didn't respond to this. This was getting close to her fear of what guys would do when they found out she was loaded.

Brad didn't seem to need an answer. He came in close and put his left arm around Ronda, drawing her to him. He spent little time sexing her up, making her pant and moan low for him. He didn't bother to strip anything off himself yet, but he did a full search of her nakedness. Holding her with his left arm, he let his right arm roam, feeling up her small, firm breasts, gliding the hand down her trembling belly to her V, pressing the heel of his hand into her lower belly and letting his fingers play in her labia, rub at her clit, and penetrate her passage. Captured in the embrace of his strong arm, Ronda gasped at the thorough and almost clinical exploration of her vagina. She moaned and rocked on the fingers.

"When I'm hard I'll fuck you," Brad said. "You want me to stroke myself up, or do you want to do it? Or do you want to give me head? I'll eat you out when we get down to business on you. I need to be hard before we can fuck, though."

Ronda sank to her knees in front of him and stripped his shorts and jock down to his ankles. He stepped out of them and she took his cock in her mouth and gave him head.

When he was hard, he picked her up in his arms and said, "Is your bedroom down this hall or through the living room?"

"Through the living room," she managed, her voice thick with need and want.

Into the living room they went. "Hey, that's a great ottoman you have there. Big and a good height."

They didn't make it into a bedroom yet. Brad draped her over the ottoman, on her belly, knees pressing into the carpet on one end, her head dipping off the other end, and her arms dangling off to the side. She writhed and panted hard and groaned as Brad knelt behind her and ate out her cunt and ass. When he was satisfied, they both were ready, he rose, mounted her high from in back and above, pressed down on her shoulder blades, slid inside her cunt, and fucked her.

"Don't worry," Brad said. "You're paying by the hour, not the fuck. We'll make it into the bedroom eventually."

At some point he'd gotten his cock sheathed and both it and her cunt and ass lubed up. Rhonda panted and mewed as he rode her cunt. Before climaxing, which was after Ronda had, he changed holes, ending up fucking her in the ass.

"You want it here too, don't you?" he'd muttered.

"Oh, god, yes," Ronda had exclaimed and then it was more of a screamed, "Yes! Yes! Shit, YES!" as he worked his way into her ass, which was original equipment.

They held on the ottoman, Brad covering Ronda from above, for a few minutes after liftoff as they cooled down. When Brad had, with Ronda still moaning and panting low, he pulled off her and said, "The kitchen's over there? You got any beer?"

"In the refrigerator," Ronda managed. "If you need to shower, it's through the master bedroom over there."

"Honey, we've just started. You're paying big bucks and you're a real sweetheart. We've just begun." It was the first time he came anywhere close to praising her contribution to the performance. He was very much the sassy and arrogant college guy.

The really interesting part came next, after Brad finished his beer and Ronda scraped herself off the ottoman and showed him where the master bedroom was.

"Great house. This must have cost you a fortune," he said as they entered the bedroom. She didn't answer and he didn't seem to need one as he changed gears from there. "That full-length mirror on the closet door. Does it come off? Can we prop it over here facing the side of the bed?"

It did and they could.

"Thought you might like to see what my shaft can do to that lovely cunt of yours," Brad said, as he propped up the mirror against the front of a bureau facing the side of the bed. He was stroking up his cock with the other hand and brought himself to a full erection quickly. He sat, naked and magnificently muscled, on the side of the bed, facing the mirror, and drew Ronda down into his lap, facing away from him. He arranged her legs to flow back around his hips--all she was wearing now were the red spike heels--and slid her slit down on his cock. He laced his arms under her pits, locking his fists behind her neck. She was in a full Nelson, with her back arched and her shimmering tits projected out.

"See. You can see the root of the cock inside you in the mirror. You can watch it fuck your snatch, in to the root, out to the rim of the glans, in to the root... like this. In and out; in and out. Oh fuckin' A, I do love that. I'll come fast if I watch that."

Ronda almost hyperventilated watching the cock do its work in her vaginal passage. Before they both climaxed, Brad moved his hands to cupping and squeezing her tits to the rhythm of the thrusts of his cock. He was thick and long. It didn't take long before he could reach the G-spot in her passage, giving her an electric charge each time he hit it.

"Oh, Fuck, I'm going to exploded," she cried out--and then did. Brad kept pulling her on and off the cock, giving her another orgasm before he, in turn, ejaculated.

"So, is that what you wanted?" He asked afterward, as they were both sitting in the living room, having a beer.

"Yes, that was intense."

"They did a great job on you, babe. You're a real work of art. What you do with the muscles of your channel... that's something you shouldn't have to pay a guy to get. He should be paying you. Not that I'm going to pay you, of course."

"I don't know. I have found Evansville..."

"Dull. Conservative. Not someplace for a trans to thrive?"

"Yes, I guess so."

"If you want to do another session sometime, instead of me doing you--or in addition to me doing you--I could introduce you to some other guys who like to cover trans. This is a university town. There are some kinky guys here with fetishes--guys who'd like what you've got. Guys who are easy to look at, muscled up, and hung. I can hook you up with great guys who will do you more regular than casual and it wouldn't cost you much if anything."

"You can?"

"Sure. I do a party now and then. For the same fee you're paying me for this, tonight, you can come to one of my parties. There will be other T-girls there--none so well done as you. And guys who like to fuck T-girls. There will be more guys looking for a T-girl than T-girls so you won't be left out. You're too well equipped to be left out anyway. Those Italians did top-notch work. You'd find more than one guy for a regular hookup. Interested?"

"Absolutely."

Evansville was looking up a bit. That mirror thing just about sent Ronda over the moon.

"You've got a really nice place here," Brad said. "You must be one rich bitch."

The defensive gate instantly fell, Ronda cooled off, and she saw Brad out soon thereafter. Was this all just the start of a campaign to uncover her lottery win and fleece her, she wondered. The fear of what guys like Brad would know and use gripped at her once more.

* * * *

Brad's party was the first time Ronda ventured out of her house in a female persona. Even then she didn't drive east on Lincoln Avenue toward the university neighborhood until well after dark, so no one would see her out and about in her slinky red sequined shift with the same lacy lingerie and red spike heels she'd worn for her private session with Brad.

The party was in full swing when she got there. There were two other T-girls there being hit on, fondled, and fucked, but Ronda had to agree that they hadn't had the high quality of work done that she had. The almost immediate attention of the eight or so all-male men there, most of them apparently hunks from the university's athletic program, switched to Ronda when she showed up.

The surprise to her at the start was that the grocery store check-out clerk, the hunky blond guy, Billy N, was there. He gave her a broad smile when he saw her enter, but he wasn't in circulation long. He already had an arm draped around one of the other T-girls and was guiding her back to Brad's bedroom when Ronda arrived.

Ronda didn't have long to think about the blond stud, though, who Brad later told her was a junior at the university and a football star there. He didn't appear again from the bedroom before Ronda had been overwhelmed by the party setting, fucked on the sofa by two guys, and had been rushed so hard after months of isolation and loneliness that she had to withdraw.

The first guy who covered her was an assistant wrestling coach at the university and he did most of the work in tiring her out from preliminaries, pinning her, naked except for the high heels, on her back on the sofa, spreading her legs and lying between them, holding her arms over her head with a grip on her wrists, and fucking her while his mouth feasted on her nipples. When he was done, an older, more academic-type of man took advantage of the wrestling coach's total domination and exhaustion of her to slip in as the coach released and slipped away, and fucked her when she was totally docile. The academic was more interested in Ronda's new cunt than the wresting coach had been, and Ronda was more than ready for his cock after the time he'd taken to explore and finger her folds, clit, and passage. She came at the touch of his hands before he released inside her.