The Drifter Cums Again

The drifter sat in the bar of the Four Seasons Hotel in Dallas enjoying a glass of very nice French wine. His suit was Prada, his shoes Kenneth Cole. His hair was perfectly cut and styled. Everything about him spoke of money and power. Yeah, this was a much nicer life-style, then hitch-hiking across the country. Yes, luxury is a much better way to live. He should have done this several years ago.

He had seen and done a lot of things. He had seduced all kinds of low rent women around the country. He had forgotten how many cunts he had fucked in the past few years as he moved from town to town. That is how he had made his living, so to speak. He would use his looks; charm and intelligence to find his marks, and then his big, thick cock would seal the deal every time. It had never failed. When he was done fucking them silly, they would give him anything, and do anything to stay with him. But when the money ran out, or he got bored, or the situation soured, he just moved on. He'd had many a run-in with a mad boyfriend or husband whose mate had cheated with him. He didn't care. He had always won every fight and altercation. He had always figured out a way to escape with his hide intact, after he had reamed the pussy and taken all their money. He was cool, very calm, could be vicious and sadistic and most important, he didn't care about anyone or anything except himself. That what made him so successful at what he did. It made him the drifter.

After a very unfortunate incident in Meridian, MS., involving a very sexy young waitress and her over-protective boyfriend, he'd run to Florida to escape arrest. He had ended up in West Palm Beach. The kind of players there were a little beyond his usual fare, but he was a very fast study. Within a few weeks, he was the most sought after gigolo in West Palm. Women of all ages were after his attentions and cock. Rich wives, rich daughters, rich heiresses. Women who had money, and trust funds, and absent husbands. He took total advantage of all the gifts, money, and pussy that came his way. He would still be there laying the pipe to all the rich, high-society northern babes down for the summer, except for that matter of that pregnant under-age girl, and how he'd put her CEO father in the hospital when confronted. He left West Palm in a hurry. He had picked Dallas, and so far, it had been the right choice. He was even doing better here with the Texas women. He had stayed with that beautiful blond and very bored housewife in North Dallas as he taught her about the finer points of sucking a big cock, then he'd hooked up with the young spoiled brunette daughter of an oil zillionaire who had wanted to get wild and crazy. Well, they had accomplished that for sure. They had checked into the Houston Hilton where he had spent an entire week fucking her in the ass while Daddy's credit card paid for it. Both occasions had resulted in extremely satisfied and appreciative women, who gave generous monetary gifts for his sexual attentions.

Now he was looking for his new mark, the next meal ticket, the next woman that he would send to heaven with his huge cock, and reap the benefits of her desires and lifestyle. Finding the right woman just took time and patience. You had to know what to look for. That certain element that let you know they were available and ready to play, even if they didn't know it themselves. You just had to draw it out of them. Then before they even knew what happened, he would be between their thighs pumping his huge prick into their creaming cunts. Taking them to places they never imagined a man could take them, and they would be his. They would abandon home, husband, family, all rational thought to be with him and his magic cock. Plus they would pay for it all. It was a nice way to make a living.

As he placed his drink down on the bar, he saw her, and he immediately knew that she was the one. Her walk, the way she entered the room, the tilt of her head, and the gleam in her eye made it obvious that she was on the hunt. Well, he was just the kind of man to help her with her problem. She appeared to be in her mid to late forties. She was about 5'9" and very attractive with red hair, green eyes and a very nice figure. Her black tailored suit bespoke money, confidence, and style. While her suit was totally professional in appearance, it was very sexy and did little to conceal a pair of C-cup breasts, a flat stomach and killer legs.

Has he observed her, he could tell she wasn't waiting for anyone. She was by herself, and looking for an interesting time. Maybe not sex, but someone to keep her company and entertained for the evening. Someone attractive and interesting. She might have sex with them, but she would decide that later.

She walked up to the bar a few seats down from him, and ordered a dirty Martini. As she waited for her drink, she looked around and noticed him sitting at the bar. She flashed him a brief smile, and turned away. When her drink arrived, she charged it to her room, and moved to table in the far corner of the bar. As she sat down and crossed her superb legs, her skirt rose up showing off her taut pale thighs.

Okay, so she was available, but you had to work for it and come to her. She held the power in every conversation, because you had to go to her table to speak to her. He could tell she was used to having control, of having the power, of being in charge. That was the kind of woman he liked to break the most. The superior ones, the ones with the attitude, the ones with the feelings of power and control. Well, after he had stuck his big cock in their uptight pussies and made them cum like never before, they would crawl thru shit and broken glass to get next to him again. It happened every time.

He ordered a Martini for himself. When it arrived, he boldly crossed toward her table and introduced himself. She had watched his approach the entire way. She liked what she saw, so after a few moments of small talk when he asked if he could join her, she nodded yes.

"So Hank what is it that you do?"

"I'm a life-style consultant, mostly in the area of recreational pursuits."

"What is that?"

"Well, I figure out what people want and need, and then I get it for them. Sometimes, they don't even know they need it, but I convince them."

"So who are your clients?" she asked suspiciously.

"All kinds of people from all over the country, but most of my clients are women."

"Really," she said skeptically, "and what do you think I need?"

"Hmmmmmm, I will have to think about that for a moment. So Katherine, what are you doing in Dallas? Business or pleasure?"

"I came for a tech convention. I am headed home to tomorrow. So it was business, but tonight is for pleasure. This convention has been a lot of hard work."

"Where's home?"

"Phoenix. So what about you? Business or pleasure?"

"Pleasure, but then my business is pleasure."

"Oh, I see." She took a sip of her Martini as she looked at him. It was if she was appraising a purchase. "And how much do you charge of this service."

"How do you mean?"

"Well, it is obvious that you are a male escort, so what do you charge?"

It was Hank's turn to sit back for a moment. He had not expected to get to this point so soon. He had never been made so early, and had never been called an escort. As he contemplated his answer, she stared directly at him as if challenging him to answer her question. "She is a very demanding bitch," he thought, "I am going to enjoy taking her down a couple of pegs."

"Well, I don't have an hourly rate. I usually work on a barter type arrangement."

"How does that work?"

"I provide my service, and at the end you determine what it is worth."

"That is a very unusual way to do business, Hank."

"Let me ask a question if you don't mind?" She nodded yes. "What do you do for a living?"

She took another sip of her drink. "I own a design software business. I am very successful and very wealthy, so your fee is not a problem."

BINGO! Now it made sense. She had done this many times before. She was a successful executive and didn't have time to sit in bars chatting up used car salesmen, or fat losers at the country club. When she wanted sex, she wanted it then and was willing to pay a professional to get it. This was a whole different story. He could see a whole new possibility forming. A new future that he had never considered before, but he had to change the relationship. Change it from buyer/seller to two adults having fun. He just had to lead her there.

"Look, why don't you and I have dinner and see how we get along. No obligation, no hassle."

She considered his offer for a moment, and then nodded yes. They decided to have dinner at the hotel. As they left the bar and moved toward the restaurant, Hank gave her the once over. She was really was in wonderful shape. She had a very sexy walk as her ass swayed provocatively under her tight business skirt. He was going to enjoy fucking this beautiful executive. No doubt.

For the next two hours over a dinner of lobster and salad, two bottles of excellent California Chardonnay, and coffee and dessert, they talked about everything. He found out that she had two children, a son 23, and a girl 18. That her husband had run off her early in their marriage with the tramp next door. She had gone back to school and gotten a degree in computer design. She had started her business in her dining room, and 12 years later, she was a multi-millionaire. She worked hard, played harder, and was never going to get married again.

She asked about his life and he told her one of his patented lies. It had been so long since he told the truth; he didn't remember it any longer. But he spun a wonderful tale about danger, travel and sex. She wanted to know more about the sex. Why, when and how did he become a male escort, and how many women had he been with? He kept it light, but he knew he had her. Yet, he acted like this entire episode was not a big deal. It intrigued her, not many men could turn down a beautiful and wealthy executive. In spite of her confident demeanor, she was nervous and had a little too much to drink. Yet, he never pushed anything. He let her wonder and wait. When the bill came, she grabbed it and charged it to her room. They walked out to the lobby, and a moment of silence fell between them. She wanted him to start the conversation, but he waited for her. Finally, she asked,

"Would you like to come up?"

"Are you sure?"

"Yeah, I would like to try that service," she smiled deviously.

"Lead the way."

She turned and crossed toward the elevators. She looked back over her shoulder to make sure that he was following. While they waited for the elevator, he could feel the sexual tension mounting. He stood close to her and just barely caressed her hand, and she shuddered with excitement. He knew that her pussy was already leaking like a faucet. He was going to enjoy stretching her cunt to the limit with his massively thick cock. They were the only ones in the elevator as it rode up to the 21st floor. When the doors closed, he pulled her to him and kissed her gently on the lips. She threw her arms around his neck and kissed him back hard. As their tongues dueled passionately, he let his hands slide down her back to her ass. With a hand on each globe of her butt, he pulled her tight against him. Katherine spread her legs slightly as he pulled her pussy against his rock hard dick. As the elevator rose, they continued to kiss passionately. Hank reached up and undid the buttons on her suit coat, and slipped his hands inside to squeeze her breasts. Her breasts were full and firm and he could feel her nipples poking out against her bra.

When they reached her floor, she grabbed his hand and almost dragged him down the hallway to her suite. Once the door closed and they were inside, he pushed her up against the wall and began to kiss her hard, thrusting his tongue deep into her mouth. After several moments of heavy kissing, Hank started to kiss and lick down her neck. At the same time, he pulled her blouse from her skirt and began to undo the buttons. When the buttons were all undone, he pushed her blouse and suit coat off her shoulders exposing her black lacy bra. Her bra was one size too small and her breasts overflowed her top. As he continued to kiss her neck, he reached behind her and undid her bra. Her tits came spilling out and they were a sight to behold. They were full and round with very little sag. They were tipped with half-inch red nipples that stood erect. He slowly kissed his way to her jutting tits and began sucking and licking her hard pointy nipples. He took her right nipple between his teeth, and she groaned, "Oh fuck that feels so good."

As he worked on her breasts, he undid the zipper to her skirt and pushed it off her hips and dropped it to the floor. Katherine was naked except for a tiny, white lace thong. The drifter admired the older woman's perfect body. She had a flat stomach and narrow hips, and obviously was in great shape. He returned his mouth to her right tit and began to suck her entire succulent tit into his mouth. While he was feeding his oral fixation, he slipped his hand into her lace thong and located her excited clit hidden in a patch of red pubic hair. He traced his fingers over her bare, wet pussy lips, and then slowly pushed two fingers into her soaking, tight hole. As he drove his fingers in and out of her swollen snatch, he clamped his lips over her excited nipple and bit down with his teeth. She grabbed the back of his head, held him tight her tit and began to thrust her hips on to his fingers trying to get them deeper into her burning hole.

"Don't stop... Oh... Oh... Fuck!!!"

Hank moved his mouth from nipple to nipple biting and licking and sucking her aching nipples, driving her mad with his teasing, but her main focus was on the two finger that were sliding in and out of her cunt at a furious rate. His fingers were slick with the juice pouring out of her hole as his fingers continued to ream her pussy. Her hips were flipping at his hand trying to drive his fingers deeper into her famished cunt. She started to shake and tremble as he drove his digits into her gushing cunt, so when he felt she was just on the edge; he slipped his thumb up her tight asshole. Katherine's vibrating pussy went off like a roman candle as she exploded on his thrusting fingers. She screamed out loud as Hank drove her through her climax.

"OOOOOHHHHH....YYYYYEEEESSSS!!!!!!!"

As her orgasm crested, Hank pulled his fingers out of her smoking cunt, and kneeled down in front of her. He pulled her thong down her trembling thighs revealing a red landing strip and the wet swollen lips of her leaking pussy. Hank started to kiss and lick his way from her belly button down between her legs. The smell of her hot broached pussy was delicious as it filled the air around him. He kissed her inner thighs slowly working his way up toward her pussy. Her pussy was red, juicy and puffy. He began to lick the wet lips of her cunt. Slowly, he parted her cunt lips with his tongue. Her taste was deep and earthy. As he pushed his tongue deeper into her boiling cunt, she spread her legs slightly and held Hank's head tight against her burning snatch.

"OOOHHH, God... Fuck yes...Fuck yes...ohhhh, eat me," she moaned again and again.

Hank used his hands to caress her legs and thighs as he licked deep into her cunt. He brought his hands up to her ass and holding a cheek in each hand; he pulled her cunt to his mouth and began sucking her clit. She raised one leg and wrapped it around his neck pulling him tighter to her creaming fuck hole. He worked her clit with his lips and tongue. He moved his hands from her ass and slid two fingers into her tight pussy and began to stroke her g-spot.

"What...are...you...doing...to...me?" Kate groaned as she thrust her juicing pussy against his fingers and mouth.

When he slid a finger from his other hand up her asshole, she exploded into another mind-blowing cum.

"OOOOOOOHHHHHHHH!!!! FFFFUUUCCCKKK!!! OOOHHH GODDDD!!!"

Kate staggered backwards against the wall dazed from her over-powering climax. She slowly slid down the wall to the floor. Her breathing was shallow and labored as she tried to catch her wind. She was in another world as she sat there with her eyes closed. The drifter stood up and slowly took off his clothes and tossed them on the floor. He unbuckled his belt, popped the button on his pants, and using his thumbs he pushed his pants and boxers down his legs. When his clothes cleared his crotch, his huge cock sprang out of hiding and bounced in front of him.

"Katherine" he whispered.

She opened her eyes and saw his giant prick swinging in front of her face. She couldn't believe how huge it was. It was 11 inches of wrist-thick cock and the giant mushroom head was pointed right at her face.

"Oh my God," she mumbled. "You're so fucking big."

He smiled down at the astounded Katherine. She was clearly nervous as he reached for her and pulled her to her feet. His giant prick pointed out in front of him like a small flagpole. She was actually scared of the thick veined column of flesh that swayed in front of her.

"Turn around and lean against the wall," he commanded.

Katherine stood frozen in front of him, eyes wide and stuck on his massive manhood. Her hands nervously covered her mouth.

"Turn around and lean against the wall," he commanded again.

She slowly turned and leaned against the wall. She spread her legs and looked over her shoulder as he stepped behind her. She was breathing slowly with her eyes closed as Hank lined his cock up to her juicy cunt. Taking his huge cock in hand, he slid the giant head along her slick cunt lips and nudge against her rock hard clit.

"Oh Jesus," she squealed as he pushed the head against the mouth of her steaming cunt. "Please go slow."

He leaned against her harder and the mouth of her cunt started to open under the tremendous pressure of his steel rod of cock. Slowly, the giant head eased past the tight muscles of her cunt and popped inside.

"OOOOOOOOOHHHHHH!" she whimpered.

With just the head lodged in her over-whelmed cunt, he started to slowly fuck her. Moving ever so slowly, the drifter managed to work in the first three inches of his giant cock into her tight, pulsating cunt. She felt like a tree trunk was being crammed up her pussy. She had never had anything this big inside of her ever. The sides of her pussy felt like that they were being stretched beyond its limits. He just continued to slowly stuff cock deep into her wet burning cunt.

"OH...MY...GOD..." she cried again and again as he pushed deeper and deeper. He met his first resistance at six inches, but that wasn't going to stop him. He was going to get all 11 inches crammed up her hot tight cunt if it took all night.

"Rub your clit for me baby," the drifter ordered.

Katherine slid her hand down between her thighs and slowly began to rub her clit. As she worked herself toward an orgasm, her pussy began to relax and Hank was able to fuck deeper into her tight snatch. The pressure was building both on her clit as she rubbed it furiously and deep inside her burning, aching cunt as Hank continued his assault on her defenseless pussy. She started to have orgasms every few thrusts as the great head nudged forward deeper inside her stretched channel. Some were small, others mind-numbing. Her whole body was shaking and trembling from the strain, but after twenty minutes, he was buried to the hilt. All 11 inches were buried in her hot wet snatch and the fun was about to begin.

"OH...MY...GOD..." she cried again and again like a mantra.

Hank grabbed her hips and pulled slowly all the way out. He watched as the lips of her pussy stretched tight like a seal around his giant prick. Then suddenly, he rammed his fat, hard cock back inside her wet sleeve and the head bounced off her cervix.