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Introduction:

The Nerd Starts Over
Chapter 1

All in all it was a very satisfactory operation. Setting up the hedge fund had cost him a few million dollars of his own money but it had been well worth it. Once the investment checks had come in it was too easy—wait a few months and send out payment checks with plenty of interest and dividends. Best of all was how stupid and trusting his bitch wife, her sister, and despicable mother had been—almost as stupid as he had been in trusting and loving Morgan. He rationalized that, however. She had seemed so genuine, so loving, so sexual that anyone would have succumbed to her. Ryan sometimes wondered what might have happened if he had been able to separate her from her scheming mother, but why wonder about things that weren’t to be. The real stroke of genius—yes, he had to admit it, he was a genius-was enlisting the aid of a clerk in the SEC. Hacking into their computers to get personnel lists had been a breeze. You’d think that Homeland Security would have insisted on better, but—no—he had been able to hack their system in less than fifteen minutes, less even than most major stores like Home Depot or Dick’s Sporting Goods. Once there it was child’s play to identify a clerk having big money trouble. In this case it was a woman whose husband had deserted her, leaving her with three children, a mortgage, and a pile of bills. Ryan approached her one evening after work when she was at her most bedraggled. At first she was skeptical, but when he put an envelope with $20,000 on the kitchen table things changed. She couldn’t take her eyes off the money—the solution to so many of her problems. Ryan promised her even more, another $80,000, in fact. He even told her how to avoid detection by the IRS or police. She followed his instructions, opening a safe deposit box at her bank and keeping the money there. She withdrew only what she needed to pay her bills so there were no bank records of major deposits or withdrawals. In return he wanted to know when the SEC became suspicious about his new company. When they showed no interest he fed his “friend” some information to speed the wheels of the government. Thus he was able to predict to the day when the Feds would raid his office and arrest the women.

Traveling on his new passport was just as simple and just as easy. His only real concern was remembering to sign his new name—George Martin James—on his charge bills and hotel registers. He was welcomed into the Hotel Intercontinental in Mexico City like visiting royalty. A quick hundred to the bell captain got him his first encounter with a she-male, something he had wanted to experiment with for years but never had the nerve to try for fear of exposure. Now he had no family, no job, no nothing—except the millions he had moved into numbered accounts in the Caymans. The bankers didn’t care about any of that. Their only concern was to keep those exorbitant sums in the bank where they could earn additional millions in interest for their bottom line.

The she-male was very attractive, beautiful actually, with long brown hair to her waist, large obviously man-made breasts, and gorgeous hips and ass. She was tall, almost 5 feet, 9 inches, which made him believe she was not of pure Mexican descent. She had large oval brown eyes, high cheekbones and long slender legs. If he hadn’t seen the bulge between her legs he would never have suspected. He paid her $500, a princely sum in Mexico. First, they went to dinner, then to a popular night club. When they returned to the hotel in a cab she couldn’t keep her hands off Ryan, opening his pants and taking him into her mouth, right in the back seat where the driver could see everything. And see he did, narrowly avoiding several collisions as his attention was clearly distracted. It was one of the best blow jobs Ryan had ever experienced, with lots of tongue action and deep-throating. The she-male swallowed every single drop just before they arrived at the hotel. Ryan walked her through the lobby as though he were escorting a beauty queen. Indeed, many heads were turned as they strode to the elevator. Once in the suite she went into action again, intent on earning her fee. She led Ryan to the huge bed, seated him at the edge. She knelt to remove his shoes and socks. Then, moving up, she unbuckled his belt and opened his pants. Ryan stood to accommodate her as she slid his pants and boxers to the floor. While his pants were going down his cock was going up. It changed in an instant, from a soft innocent-looking object into an instrument of steel, specially designed for hard fucking. Ryan removed his own shirt then moved to undress his companion. She wore all high-end clothes and lingerie of the finest materials. Her bra and panties were of the purest silk, as were her thigh-high stockings. Like Ryan, her cock sprung to attention as it was exposed to the cool night air. Now it was Ryan’s turn to kneel. He took his first cock in hand, examined the head closely, and stuck his tongue out to lick the head. The sensation was not unpleasant so he proceeded to engulf the hard tool in his mouth. He’d had plenty of blow jobs in his life, but those were all on the receiving end. He licked and sucked with abandon, celebrating his new-found freedom from convention. He sucked hard and bobbed his head up and down. He could feel the cock stiffen and knew from his own experience that she was about to cum. He could have removed his head, but he didn’t. He wanted to experience the whole thing so he continued sucking as he deep throated and swallowed his first cum--if women could do it, why not he? He couldn’t say it was the best thing he had ever swallowed, but it wasn’t the worst either.

When he had satisfied his partner he stood up and moved behind her. Standing, she leaned over the bed until her elbows contacted the mattress. She spread her legs to better accommodate her client. Ryan pressed his cock against her sphincter forcing it open. She reached back to apply some gel lube to Ryan’s cock and to the interior of her own ass. Then she pushed back as Ryan pushed forward. His cock head moved swiftly into her rectum. His hips bucked forward and back, plunging his cock deep into her bowel. He loved the feeling of her ass squeezing his cock. Sadly, it reminded him of Morgan and Sara, but the thought merely increased his determination to cum into her ass, and cum he did! He sent rope after rope of steaming hot cum right up into her intestine. When he pulled out he left an inch-wide hole, through which his copious cum was pouring like a waterfall. She pushed her hand into the breach and rushed to the bathroom, returning a moment later with a wash cloth firmly wedged in her ass. She dressed, said goodbye and started to leave. Ryan chased after her, but only to give her a hundred dollar tip. He slept well for the first time in months.

The next morning Ryan was at the airport for his connector flight to Rio de Janeiro. Not only was the city the home to thousands of spectacular women, it was also one of the few places where there was no extradition treaty with the U.S. Ryan accessed his Cayman Island account to purchase a three bedroom apartment with fantastic views of Rio and the beach at Ipanema. From his balcony he could see hundreds of willowy tanned women in bikinis not much bigger than three postage stamps. He picked up a computer program to learn Portuguese and settled into his new life.

Every day he stopped by a nearby news stand to buy the International Herald Tribune. He enjoyed reading about the ongoing case involving his three pregnant cunts. All their denials and claims of knowing nothing, doing nothing were countered by the mountains of his manufactured evidence. Even their statements that they had never even been to the office were countered by the plethora of fingerprints he had so painstakingly applied. The government’s case was airtight so they never went to trial. Plea bargains were finalized; all their property, including Morgan’s $80,000 diamond engagement ring, was seized for distribution to the creditors and they were to be imprisoned for a minimum of twenty years. The best of all was that their children were to be removed immediately after birth to foster care. How fitting—they conceived in deceit and carried the children with the sole intent of destroying him. Now they would have nothing; he burst out laughing at the thought. He had one other idea. He pulled out an old post card and wrote in block printing, “IT’S NEVER A GOOD IDEA TO GLOAT IN A NERD’S LIVING ROOM ABOUT HOW YOU’VE PLAYED HIM FOR A FOOL.” He sent it to an attorney in Cleveland with instructions to mail it to Morgan on a certain date. Enclosed in the envelope was a money order for $1,000. This would be Morgan’s final punishment. She would know that he was alive and that he had set her up, but there would be nothing she could do about it. Again, he laughed hysterically.

Chapter 2

Ryan experimented several times with she-males, but, though different, he realized it wasn’t for him so he set about finding some real women. In a cosmopolitan city like Rio it’s never difficult to find women, but finding the right kind of women, that was something else. He wanted to find someone who wouldn’t be so affected by his wealth. He refused to go through the same hell again, so waitresses, cocktail girls, and bar pickups were out. He decided he needed to join an exclusive country club. There would be fewer options, but those that existed would have some money, even if not as much as he did. To do this he needed introductions. After all, one does not just walk up to an exclusive club and ask to join. Eventually, he decided that charity was the right approach. He attended a snooty charity art auction and drew attention to himself by successfully bidding on several expensive paintings and sculptures. The charity sponsors were so grateful they invited him to other functions. During one cocktail party he mentioned that he missed playing golf since moving to Rio. Were there any places they might suggest? He was invited to play at several clubs. There was high interest in this stranger—not only was he rich, he was also single. He’d be a great catch for some daughter of a good family.

Soon he was the hit of Rio society, and that was how he met Wendy. He went to play golf one day with his banker. When Ryan, now known as George, went to his cart he found it was already occupied by Wendy, who was introduced as the banker’s daughter. Privately the banker whispered to George, ”…Sorry, my wife’s idea.”

“No problem,” George replied, and it wasn’t. Wendy was very pleasing to the eye—about 5 feet 10 inches tall, long brown hair and eyes, with a thin athletic body. Wendy’s exotic looks were the product of a Brazilian father and an Irish mother. She obviously knew why she was here, too. She started flirting with George even before they hit the first tee. She marveled at every shot he made, every putt. While in the cart she leaned against him whenever possible, resting her hand on his arm and thigh. On one occasion she moved her hand up toward his crotch. When he looked over at her she smiled coyly, promising more with her eyes. He was looking forward to their first date. He’d score for sure.

He asked her to dinner and took her to the finest Brazilian steakhouse in the city. They laughed over drinks before dining. She moved closer to him, placing her left hand right onto his crotch, before kissing and licking his ear. “Why don’t we skip dinner?” she suggested.

George called the waiter, paid for the drinks, and left an extremely generous tip before escorting Wendy out to his car. He wanted another Porsche but decided on a Lamborghini because it was showier, and he did want to attract attention at this point. However, to hide his true identity he had grown a short beard and changed his hairstyle, cutting it much longer than in his days with Morgan. He also fixed the nose he had damaged as a child when he peeked around his mitt just in time to be struck by a vicious line drive. Once in the car, Wendy leaned over, grabbed his head, and kissed him passionately. “Can we hurry? I’m already wet. I need you…and damned soon.” George ran through the gears as quickly as possible bringing the car to the speed limit almost instantaneously. The Lamborghini tore up the hilly streets en route to George’s apartment. He pulled quickly but carefully into the basement garage, parking in his assigned space near the rear elevator. Fortunately there were no other riders so the elevator rose quickly to the top floor. Wendy was undressing even before George had opened the door. He closed it, turning into her arms. Their lips met passionately and, an instant later, her tongue was in his mouth, twisting and dancing with his. He started to unbutton her blouse—he could never understand how women could tolerate buttons in the back of their clothes. He opened her blouse and unsnapped her bra in less than a minute. She moved her hands to his belt and soon his pants joined her clothes on the floor. They stood naked before each other, the spectacular views of the beach and ocean in the background. The view, however, was ignored at this moment. George cupped her breasts. As befitting her trim body, they were not large—probably a good B cup he decided. Her body descended in a straight vertical line from her breasts to her mons which jutted an inch forward and was decorated with a small triangle of dark pubic hair. There was a three-inch space between her long slender legs, more than ample room for his hand or cock. She was right; she was soaking wet, obviously ready for some good fucking. George’s erection stood out ninety degrees from his slender body. He hadn’t had any real sex in over a month unless you count sex with his hand.

George led her to his bedroom, the largest of the three in the apartment. The drapes were open revealing a tempered glass wall running from floor to ceiling, broken only by a sliding door leading to the balcony. The king-sized bed with the hand-carved Spanish headboard dominated the room. If one looked closely one could see several sturdy steel rings bolted through the heavy end posts. George hoped to put those rings to use tonight, and judging from Wendy’s eagerness, he thought he probably would.

Wendy wasn’t just ready to fuck, she was taking charge. She pushed George back on the bed then knelt on the floor. She tickled his balls with one hand while stroking his tool with the other. She leaned in to kiss the cock head before winding her tongue all the way around the head. “Take it all,” George commanded. She did. His seven inches went all the way into her throat before she backed out almost, but not all the way, before plunging back in. Up and down her head moved gradually increasing its speed. When George felt he could take no more of this exquisite torture, he pulled her up off his rigid dick. Lying back on the bed now, he pulled her forward until her sex was just above his erection. She took it in hand, rubbed the head slowly up and down her slit, moaning as she did. She lifted her hips, moved slightly forward and sank down, spearing herself on the rock-hard tool. She was as tight as a teenager, but her flowing juices eased the passage deep into her hot, hot cunt. Wendy placed her hands on George’s shoulders as she started to rock grinding her swollen clit into George. She threw her head back in her ecstasy as they neared their first orgasm together. George, having only masturbated this past month, couldn’t hold back against her assault. “OOOOOHHHHHH, GOD!” he exclaimed as he poured cum into her, soaking her already dripping cunt and womb with his seed. Wendy was only a few seconds behind him. Indeed, his release seemed to trigger her response. She humped forward violently as the orgasm claimed control over her body. She shook over and over before falling onto his chest, exhaling a deep breath as she collapsed into his arms.

“That was incredible—so fucking incredible,” she gasped. “Fuck, I needed that so badly.”

“Yeah, I liked it, too,” he kidded.

She gave him a playful jab in the arm. “I noticed just how much you liked it. I’ll be leaking for hours. Your bed is going to be a mess. Hell, it’s a mess now.”

She slid off him but snuggled close, her arm across his chest, her head resting on his shoulder. Her hand idly traced a circle around his nipple.

“Wendy,” he asked, I’ve been meaning to ask you something. How does a Brazilian woman get a name like Wendy? It seems a bit out of place here.”

Wendy laughed. “My mum is Irish. That’s also the source of my English. Growing up her favorite movie was ‘Peter Pan.’ The girl character is named …”

“Wendy,” he interrupted.

“Right, but you should try to grow up around here with a name like Wendy. I felt like a fish out of water all through school. Fortunately I was able to go to university in Dublin. I stayed there with my grand-parents while studying. But I felt like a fish out of water there, too.”

“Why,” he asked politely.

“Because of my skin color which is much darker than any Irish and my Brazilian clothes and habits. My food preferences are rarely found even in a cosmopolitan city like Dublin, so many things. All the same, I loved Ireland. But you probably think I’m talking too much.”

“No, I’m actually enjoying it.”

“Good, so am I, but I do have to apologize for showing up at golf the other day. That was all Mum’s idea. She thinks I should get…, no, be married. I’m almost twenty-seven, too old to be single in her world. Hell, I’m having too much fun to settle down. Why are you still single? You’re much older than I am.”
“I was married once, in the U.S., but it didn’t work out. I married for love; she married for money. It turned out badly so I’m single again.”

“I’m sorry it didn’t work out, but I’m glad you’re single again.”

“Yeah, so am I. What do you think? Want to try something else tonight?”

She smiled slyly, “Will it hurt?”

“Maybe… maybe not.”

“Oh, I hope so. I love sex when it hurts. I bet you want to fuck my ass, don’t you…unless you’re into S and M?”

George moved quickly, retrieving some lengths of rope he had hidden under the bed. He tied her wrist using an anchor bend he remembered from his scouting days. He flipped her over onto her stomach and tied off to one of the rings. He tied her other wrist to the opposite ring. Now her upper body motion was limited but he was not done. He ran another line through the ring, around her knee and back to the ring after pulling the knee up even with her chest. He tied the other leg similarly. Now she was bent kneeling with her head forced down and her butt in the air. George stood on the bed behind her, lubed his cock, and forced it into her. She whimpered in pain; she was stretched without warning or preparation. It was just what she wanted—pain that evolved into exquisite pleasure. As George entered her ass she squirmed to accommodate him until her ass adjusted to his girth. George humped her mercilessly, showing interest only in his pleasure, but in that disregard bringing her the feelings she sought so badly—it hurt so good!

Wendy moved to meet George’s thrusts, pushing back as he thrust forward, ramming his hard cock to the maximum depth possible. She also moved her ass up and down which forced him against the walls of her bowel, an action that increased his pleasure immeasurably. Even though he had just cum in her still-leaking pussy, he soon reached his limit and poured even more creamy cum into her ass. He was now totally drained. Wendy, for her part, was almost ready herself. She reacted strongly, the orgasm taking control completely. She thrashed futilely against her bonds then collapsed into a ball unconscious.

Chapter 3

She awoke the following morning, her bonds gone, her body stretched out under the duvet, George lying next to her, his head inches from her face. He was snoring lightly. She shrunk slowly beneath the blanket until her mouth lined up with George’s cock. She licked it tentatively—carefully—watching closely as it grew in length and girth. Once hard she took him completely into her mouth. She could taste the mixture of flavors—his cum, her cum, and, yes, even her own ass. She realized he was awake when he lifted the duvet to examine her oral handiwork. He spun her around so she laid atop him, her dripping pussy just above his hungry mouth. Wendy continued to suck him off while he licked her from ass to clit. He fucked her with his tongue, using his fingers to massage her clit and ass. She started to gyrate, rubbing her mound into his face; he humped her mouth and they each sought release in their own way. When it came it was like a tsunami washing over them, submerging them in pleasure. They collapsed together in a pool of their combined sweat. Neither was able to move for many minutes.

As great as the sex had been George wasn’t ready to settle down. He continued to date Wendy, enjoying the fruits of her body while remaining open to other offers. If Wendy was concerned she never mentioned it. One day, while shopping in an exclusive shop, he met Renata. Actually, he turned suddenly almost knocking her down. He apologized so profusely and sincerely he barely noticed her splendid beauty. Renata was dark, probably part Indian. She was much shorter than Wendy, no more than 5 feet, 4 inches. Her lush body was filled out much more. Her breasts were huge, DD’s at least, but firm, and her ass was broad and round. Different than Wendy to be sure, but extremely sexy and very beautiful, her face was circled by ringlets of black hair. He wondered then what her pussy looked like and was suddenly determined to find out. He offered her lunch as atonement for running into her and was surprised when she accepted.

Once seated she spoke, “You look very familiar. I know we have never met but, somehow you look very familiar.”

“I’ve had my face in the newspapers a bit recently,” George offered. “I’m very involved in charity work here in Rio.”

“That’s it. I remember now. I saw you at the annual Charity Ball. You were with a very stunning tall woman.”

“I’m sure she could not possibly have been as stunning as you are right now,” said George leaning forward so their faces were only inches apart.

“Hmmmm, you don’t waste any time, do you?” Renata licked her lips teasingly.

“I’m only being honest,” he explained.

They fenced back and forth all through lunch. She learned that he was a retired businessman from the States. She told him that she had her own shop here in Rio, financed by her millionaire stockbroker father. He vowed to himself to check all this out very carefully. After lunch they retired to his apartment. Upon entering Renata walked directly to the bedroom. “Coming?” she asked, turning around as she walked. “Isn’t this what we both want? Why waste time with silly formalities?” George had to agree so he followed her eagerly, shedding his clothes as he went. Renata was also naked by the time he entered the room. She leaned back on the bed and he marveled at the richness of her body. She reached out for his growing dick as he approached. Her hand glided easily over the loose skin, first covering the head and then moving down to the base. It was an extremely sensuous experience. She sat forward inhaling deeply. She loved the aroma his cock emitted so she licked delicately at the tip. “Yum,” she said. “Yum, yum, yum, I love the way you taste.”

“Well,” George whispered to her, “let’s see how you taste.” He leaned at the waist to examine her cunt. Like many other young Brazilian women she had a narrow strip of trimmed pubic hair which came to a point just above her clit. He stuck his tongue out to sample her wares. She was already damp--tiny droplets of nectar forming on her labia. He licked her eagerly, taking time to gingerly nibble and suck her swelling clit. She pulled his head to her as he forced his tongue into her cunt. “Oh, my God! That’s fantastic. Harder…please… harder.”

George responded by tongue fucking her as fast as he could. As much as she loved it she wanted his cock more. “Goddamn…FUCK ME…NOW!” George was happy to oblige. He leaped up spearing her cunt on his steel rod. He legs were wide apart, making his entry easy and swift. She met his lunges by wrapping her legs around his neck. Pulling George forward forced her cunt up so he would penetrate her to his maximum. Her pussy was pure velvet, not at tight as Wendy, but much more active. Her humping lifted him off the bed at times, so wild was their joining. Harder and harder they fucked; her eyes glazed; her breathing became shallow. Then… a sudden gasp was accompanied by a massive shiver as her orgasm took control of her body. She drained like an inflatable doll that had sprung a massive leak. George had not yet cum so he kept his cock where it was—deep within Renata’s cunt. He slowed his pace so he was barely moving, giving her time to recover before initiating a new assault on her body. He leaned his head down to suckle her nipple while rolling the other in his hand. Slowly she returned to life, yearning for more of the ecstasy his cock could provide. She signaled her readiness by wiggling her abdomen and gripping his cock with her vaginal muscles. She looked into his eyes with real desire as she started a slow humping motion. George matched her thrust for thrust. Faster and faster they moved together. Harder and harder their pelvises crashed into each other. No human being could long endure such sexual excitement and punishment. George stiffened as he rammed his cock home. Suddenly he EXPLODED into her; rivers of cum drenching her womb and cunt. He shot and shot into her. Over and over white cum erupted from the tip of his cock. Finally, after shooting into her ten times he was sated. He fell off her onto the bed exhausted. But what an exhaustion he felt. He realized that they had fucked and eaten each other for almost an hour yet they had never kissed. He held her head, pulled her closer, and placed his lips on hers. They were soft and full. Her meaty tongue met his with vigor and passion. Only when they broke the kiss did either relax. They lay on the bed breathing heavily until they recovered enough to stand and dress.

“Will I see you again?” George asked.

“I hope so,” she replied. “I haven’t been fucked like that in a long, long time.”

George thought to himself—I’m really going to enjoy Rio.
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