Tessa the Toiler, Chapter 5  (MF, cons, light SM, anal)
By Paco Svengali
Released 03/13/2004
Updated 08/27/2007:  Format



Chapter 5 - Earning Her Money the Hard Way

	Tessa smiled to herself.  The evening had gone well.  Jerry would be happy.
	Tessa slept late this morning, making sure that she was refreshed from the romp that she had with Jack the night before.  She had taken her time getting ready, ensuring that she looked her absolute best for her evening with Helmut.  Her outfit for the night was the girl's best friend - the little black dress, the hem just above her knees and showing off her lovely legs, the top coming down low enough to give a hint of what awaited a lucky man, but not too low to become an issue.  Her shoulders were bare, her limbs long and lovely.  The whole package was topped with a face that turned heads, blue eyed, blonde and with a lovely smile that made many a man's heart skip a beat.
	Meeting Helmut had gone without a hitch.  She had joined him at the Palmer House, where they proceeded to the social affair.  Helmut was just under six foot.  He had a good body with broad shoulders.  His face was sharp, his eyes a bit hard for Tessa's taste.  With a slight hint of a German accent and a ramrod stance, he would look good in a Gestapo uniform.  
	This was unfair to him, however.  This evening he was garbed in a tuxedo, as were all the men.  He had been attentive and charming throughout the evening, their conversation flowing smoothly as if they had known each other before.
	The affair that they attended was one of those that you read about on the society page the next day.  It was held right in the Palmer House and was for the care of wounded birds or something like that.  It was attended by the city's upper crust, which proved hilarious to Tessa.
	When Tessa decided to enter the 'profession', she knew what her assets were.  She was a blue-eyed blonde with a face that would launch a thousand ships, as they say.  About 5' 4", she had a set of breasts that most women would kill for.  They were full and firm with no sag to them and topped with nipples the size of eraser tips when aroused.  Her stomach and hips slim, the whole package supported by a gorgeous pair of legs.
	One rule that Tessa set for herself was that she would only deal with the best, the best was defined as those who had the money.  No standing on street corners for her.  She knew what she had going for herself, and was going to sell it dearly.  Added to the fact that she, herself, enjoy a good romp in the sack, that it was going to be a two way party, made Tessa a very sought after woman.  
	As a result the evening proved to be unique to Tessa.  Normally the last thing that would happen to her was that she would meet the wives of her clients.  Tonight proved an exception.  With the city's snobs being on hand by the ton, she found it hilarious when she met a client who had a wife with him.  They would turn red or try to ignore her. However, knowing that these were clients and that she depended on them for her livelihood, she was careful not to embarrass any of them.
	Jerry was there with his wife as expected.  It was Jerry who was paying her to be with Helmut and she was especially careful with them.  Helmut and she joined them at their table for dinner and she made sure and that things when smoothly.
	It was Maury who cracked her up.  Maury always complained about his wife and kids, giving that as the reason for his seeing Tessa.  And who was there with is wife?  None other than Maury!  Deborah, or Debbie as Maury called her, was in her early forties and looked great for her age.  She was still slim and trim, and with a pleasing personality.  Not that Tessa cared, if Maury wanted to fuck around behind his wife's back that was his business, but one thing that Tessa knew was that Maury would have to get another excuse to cheat on his wife.  Debbie was delightful as far as Tessa was concerned.  Boy, was she going to have fun sticking it to Maury the next time she saw him.
	The drinking and dancing were over and now it was time for Tessa to earn her keep.  Jerry told her to do a number on Helmut and he backed it up with a wad of money to make sure that Tessa did her absolute best.  Helmut was a prospective client for Jerry's firm and Jerry would do anything to land him.  
	
	As the door closed behind them, Helmut reached from behind Tessa and held her by  her shoulders.  Kissing her on her back, he said with a bit of a quiver in his voice, "Now Tessa it's time for you and me.  I've been looking at you all night dreaming of you in bed with me.  Now I'm going to have my dream come true."
	Turning to face him, Tessa let her hand find his crotch.  He was already half hard.  "Helmut, I'm yours.  Tell me what it is you want.  You don't have to wait anymore."
	Inhaling, he looked down at her.  He could make out the top of her breasts.  Her hand on his growing cock made his pulse beat a little faster.
	"I want you.  I want you spread out in bed so that I can fuck you.  I want you at my mercy.  Tessa, take your clothes off, take them off now," he said in an irregular breath.
	Tessa was a little concerned about what Helmut was thinking.  What did me mean when he said that he wanted her at his mercy?  She wasn't into pain.  She wasn't into heavy kinky sex.  Yeah, sometimes up the ass, maybe a spanking or something like that, but keep it light, nothing that left her aching or with marks on her body.
	"What is it you what, Helmut?"
	"Just strip, Tessa.  Get those clothes off.  Don't worry, I won't hurt you."
	Helmut's was breathing harder yet.  His cock was pretty solid even though it was still in his pants.  His voice was getting ragged.
	Stepping back, Tessa reached behind herself and unzipped her dress.  Letting it fall to the floor, she stepped out of it, leaving her standing in just her half bra and thong.
	"Ahhhhh!  Tessa, you are beautiful.  I must complement Jerry, his tastes are exquisite.  Now the rest of your clothes, let me see all of you."
	Tessa looked at Helmut.  Usually by this point, the man was all over her, pawing her, grabbing her tits or ass.  Instead, Helmut stood there, his pants looking like a pup tent, watching her, transfixed.  This one was going to be different, she thought to herself.
	She unsnapped her bra and threw it on the chair.  Cupping her tits in her hands, she offered them to Helmut.  With her nipples caught between her thumb and forefinger, she said, "They're yours, Helmut.  Suck them.  Kiss my nipples.  They need you."
	Finally he moved, but not as she expected.  Instead of coming to her, he stepped aside and removed his jacket and then his shirt.  The rest of his clothes followed in rapid succession, until his stood before her in just his shorts.  They were distended from his swollen cock and the front of them was showing signs of stain from his leaking prick.  In one swift move, Helmut's shorts joined the rest of his clothes.  Now standing naked before Tessa, Helmut grabbed his cock and looked at her.
	Tessa made a move toward him.
	"No.  Stop.  Take your panties off.  I want to see all of you," he commanded.
	Tessa had expected that Helmut would want her to suck on his cock, play with his balls, or something like that.  But if he wanted to play 'I'll show you mine, you show me yours', and that was all right with her.
	Hooking her thumbs into the side of her thongs, she slipped out of them.  Tossing them to the side, Tessa stood before him.  While Tessa didn't shave her pussy bald, her pubic hair was light and fine, leaving her pussy for the world to admire.  Her cunt lips came up high on her mons, a sight that made most men groan.
	She put her hand over her cunt and rubbed it while looking Helmut directly in his eyes.  "Helmut, my pussy needs your love.  It needs your cock shove up it," she said with a need in her voice.  The fact that he just stood there, stroking his cock and making no move toward her, had Tessa amazed.  The guy had restraint or there was something kinky about this whole thing.
	"Get into bed, Tessa, while I get ready."
	"What is it you're going to do, Helmut.  What do you mean by 'get ready'?"
	"Don't worry, my dear.  I won't hurt you.  You my even enjoy it.  Now get into bed.  Take those covers and throw them aside."
	Tessa pulled the coverlet and blanket aside, throwing them off the foot of the bed.  She sat down on the edge and eased herself into the middle of it.  
	Helmut reached into one of his suite cases and pulled out silken ropes.  He threw them on the bed.
	"Helmut, what are you thinking?  I told you that I'm not into SM.  No pain, you hear me?"
	"Darling, I won't hurt you, I promise.  Just let me tie you up.  Let me take control when if fuck you.  Please.  I love the sight of a woman straining against the ropes and me being in charge.  I love the sight of a woman being helpless as I fuck her.  Again, trust me, I won't hurt you."
	Tessa looked at the man.  She was concerned of what he might do.  She didn't want to be hurt or be bruised so that she would be out of action for several days.  Yes, Jerry had given her a good hunk of cash, but it didn't cover being beaten black and blue by some weirdo.
	"Helmut, if you do something that leaves me showing signs of a beating, so help me God, I'm going to get even with you, you hear?"
	"Tessa, you won't be harmed.  Believe me."
	Helmut came up to the bed, his cock swaying.  He reached over to Tessa and pushed her onto her back.  Taking the ropes, he tied her wrists and ankles, each to a corner of the bed.  His knots were not tight and he didn't pull her limbs as to make her uncomfortable.
	"Tessa, you are lovely.  Your breasts, look at them.  Your nipples, they're like two ripe raspberries."
	Finally Helmut reacted to her body.  He leaned down and stuck his tongue into her navel.  He came up and kissed her breasts, first one then the other.  Placing a hand on each side of her, he proceeded to kiss and nibble at her nipples, causing them to redden and swell.
	Helmut was good at making love to her breasts.  She was becoming aroused.  Her legs strained at the ropes as her hips reacted to his ministrations.  
	His hand gently danced down her stomach, coming to her cunt.  Cupping her mons in his hand, he used it to massage her mound in a circular motion, sending additional quivers through her body.  Tessa couldn't help herself as she let a whimper escape through her lips. 
	"Ohhh, Jesus, Helmut, don't stop.  Please, don't stop," she whispered as her hips thrashed from his lips and hands working on her body.
	His fingers slithered through her cunt lips, pulling her secretions from within her, smearing them over her labia, lubricating her.  He ran his fingers into her outer lips several times before he let one of his fingers enter her pussy, followed by a second.  Running them into her love channel, Helmut slowly worked his finger into her cunt in search of her clit.  It wasn't hard to find.
	Tessa's clitoris was another one of her assets.  Like her nipples, Tessa's clit was the size of an eraser head when aroused.  There were many clients that were enthralled with sucking on it until she came in a screeching climax.  It was one of the reasons that she was so selective with her clients.  With a clit that was so easy to arouse, Tessa enjoyed fucking and loved to cum with her client.  Therefore, she wanted to make sure her clients were ones that she could enjoy sex with as a participant, and not acting as just a hole to be filled with a prick.  Sex to her was not only a business, but also a pleasure.
	As soon as Helmut touched her clit, Tessa's whole body gave a lurch as if an electric shock went through it.
	"Oh, God!  Touch me, rub me there, Helmut."
	Helmut let go of her tits with his mouth, moved down to her navel giving it a tonguing as he passed it, and proceeded to her pussy.  Using his tongue, he probed her cunt lips letting his tongue take over for his fingers.  He found her clit, and with his tongue and lips, he began to work on her, sending Tessa into seizures of ecstasy.  She thrashed and shook her hips as best she could with the ropes holding back  Her breath was becoming short and she could tell that if Helmut kept this up, he would drive her over the edge.
	Suddenly Helmut stopped.  He came up and got off the bed.
	"Now, my dear, some additional pleasure for you," he said as he left her and headed off to the bathroom.  Panting , her body heaving as she tried to catch her breath, Tessa heard water running.  She couldn't figure out what he was doing, all she knew is that he had taken her to the brink and left her crying for more.
	Looking up, Tessa saw him coming back to the bed.  His cock was rigid as a pole.  He had a towel in his hands along with something else that she couldn't make out.  She had no idea of what he was up to, she only knew that his actions thus far were wonderful, though a bit bazaar.  
	Helmut knelt on the bed again, and leaned over to kiss her, driving his tongue into her mouth.  He took his hand and placed it under her chin, his fingers and thumbs on either side of her cheek while he probed her mouth for her tongue.  Suddenly pulling back, he drove a damp washcloth into her open mouth.  It was done so quickly that Tessa couldn't do anything to stop him.  
	Pushing it into her mouth with his fingers, he smiled down to her.  "Don't worry, Tessa, I said that I wouldn't hurt you, and I'm not.  Just trust me.  I'll show you what real pleasure is, pleasure that you've never know before."
	Now Tessa was scared.  She was used to the idiosyncrasies of the male animal and their sexual proclivities, but now this was going over the line.  She was tied to a bed with a cloth stuffed in her mouth.  If there was any hope of pushing the washcloth out with her tongue, that hope quickly faded as Helmut reached over, tore off a piece of tape and slapped it over her mouth.  She couldn't scream if she wanted to.  Helmut was in total control.
	She waited for his next moves.  Much to her surprise, he began to kiss and suck on her breasts and nipples again.  His hand moved down to her pussy, his fingers entering her to resume massaging her clit until it was sticking out through the folds of her cunt.  In spite of herself, Tessa found that she was starting to react to his manipulations again.
	Helmut didn't quit.  He kept on working on he tits and pussy, making her more aroused by the minute.  With the washcloth in her mouth, she found it not as satisfying as she would otherwise, but still he was working her towards the edge of her control.
	Again, he got out of the bed.  Reaching over, he took a bath towel in his hands.  It was wet, but appeared to have been wrung dry as possible.  Holding by the ends, he pulled it taught.  Wrapping the corner of it in his hand, he looked down at her.  
	Her body was still shaking from his ministrations.  Her chest heaved as she tried to regain her breath.  Her eyes, wild, looked at him.
	"Now, my dear, it's my turn."
	Without a warning, Helmut swung the wet towel in an arc, coming down across Tessa's thighs.  The wetness in the towel gave it weight but because it was cloth, it didn't have the ability to break skin though it did cause a great deal of pain.  When it hit Tessa, her whole body reacted as if she was shot with a bolt of lightning.  The sound of the impact was sharp, a loud whack across her legs.
	"You fucking whore, now you're going to pay for it," Helmut said as reared back for a second blow.
	Again he landed the wet towel across her thighs. Whack!
	Tessa tried to struggle, but the ropes held her in place.  She could wiggle somewhat, but do nothing to really avoid the whipping or reduce the impact of the towel as it smacked across her body.  She did make sure her knees were together to reduce the chance that her labia was harmed.
	"Fucking cunt, I'll teach you, you bitch," growled Helmut as he laid into her again.  Sputtering obscenities, he hit her several more time across her thighs.  She could feel them becoming red and sore from the beating they were taking. 
	Stopping to catch his breath, Helmut grabbed his cock and stroked it.  "I'm going to shove this up you ass, bitch.  I'm going to fuck your ass until I tear you in two, whore.  You miserable fucking cunt."
	Again he reared back, but this time his aim changed.  He brought the towel across her stomach.  The next time it was across her tits.  The room echoed with the sound of the towel hitting flesh, the flesh reddening where it struck.
	Tessa breasts reacted to his beating.  Her sensitive nipples were quickly getting sore and began to ache.
	But there was something else that Tessa didn't count on.  When the towel come down on her, her body froze in preparation for the impact, her hips rolled and her thighs rubbed together.  After several of these stinging slashes with the towel, Tessa felt her pussy lips becoming more and more sensitive.  It seemed that her pussy was reacting to Helmut's beating; it was beginning to seep pre cum.  He was turning her on.
	Helmut stopped.  "You fucking bitch," he snarled and he knelt over her, his engorged cock swaying in front of her wide, pleading eyes.  He reached down with his hand and drove a finger up her pussy.  "I'm going to fuck you, cunt.  I'm going to rip you apart with my cock, you miserable slut."
	He jammed his finger in and out of her twat as he looked down at her, ranting, his chest heaving.  
	Feeling the juices leaking out of her, Helmut smiled down at her and said, "So you pussy likes what I'm doing to you, does it?  A typical whore, that's all you are, a whore."
	His cock was rigid, the shaft red with the veins distended and the knob turning to purple.  Ropy pre cum swayed out of the tip only to drip down onto her as he knelt over her.
	Again he stood up and took the towel by the corner.  "Bitch," he said through his teeth as he unleashed two, then three whacks with it across her stomach.  
	Suddenly he stopped, towel held back readying for another swing, and emitted a grunt.  His eyes widened as if in surprise and he dropped the towel.  Grabbing his cook, he came up to her on the bed and directed his prick at her.
	"Oh shit," he cried.  His knob jerked and a wad of cum erupted from his prick and splattered on Tessa's chest.  Holding his cock and rapidly pumping it, spurt after spurt of creamy cum shot out of his balls and landed on her.  Kneeling, fighting the breath, the German spewed his cum, leaving ropy streaks across her tits and stomach, some of it gathering in her navel.  
	Feeling his cum splatter on her stomach and tits, her nipples sensitive from his whipping, Tessa felt her pussy give a slight quiver.  Her hips locked as a wave passed over her.  She didn't believe it at first, but in spite of everything, she was responding to him.  She was having her own orgasm.  It wasn't her usual one.  It wasn't one that went on and on.  Instead, holding on to the ropes with her hands, she felt three or four seizures in her cunt and then a tapering off.  Her chest became pink and covered with goose bumps.
	"Ah, my little whore, so you like what I did for you, did you?" said Helmut as he knelt over her, letting the last of his cum drip out of his prick.  "Well, the night is still young yet.  Trust me, there's more to come."
	Helmut stood up and went into the bathroom taking the towel with him.  Tessa heard water running.  Apparently he wasn't done with her.  She was in for more punishment.
	Coming back to the bed, Helmut surprised her by wiping his cum off of her with a facecloth.  Usually they left it on, getting the some perverse feeling seeing a woman covered with heir own cum.  When she was clean, he climbed over and sat down on her, placing all of his weight on her.  Holding firmly, he proceeded to untie her, then cross her arms, followed by her legs, until she found herself lying on her face.  He succeeded in flipping her over, never giving her a chance to free herself.
	Tied securely, Helmut reached over to a chair, pick up a pillow and shoved it under her stomach leaving Tessa's ass as a high point.
	Because she was face down on the bed, Tessa had a harder time following what Helmut was doing.  She saw him reach over and take a tube in his hand and squire something into it.  With the greased hand, it seemed to her that he was sitting there and masturbating. 
	After a few minutes, he stood.  "Now, Tessa, let's have some more fun, shall we?"
	Looking at him as best she could, Tessa was amazed at what she saw.  His cock was erect as if nothing had happened.  He had oiled it with something and whacked off to get it hard.  He was ready to go again.
	Kneeling on the back of her thighs, Helmut forced the ass cheeks apart and squeezed some of the lubricant between them.  With his fingers, he spread it around, screwing his finger into her asshole for a second or two as he passed over it.
	"Now, my dear, lets see if I can make you cum again.  Let's see if we can wake up that pussy of yours."
	Helmut got off the bed and reached for the wet towel again.  This time without the furor that he exhibited before, he began a paced whipping of her backside with the towel, first the back of her thighs, then her back, and finally her buttocks.  Whack!  It was slow and metered. Whack!  He was controlling himself.  Whack!  And it was getting to Tessa.  Whack! 
	 Every time the towel came down on her - whack! - her body jerked in reaction to it. Whack! Her skin was beginning to redden. Whack!  Her breath was becoming shorter. Whack!  And, again, her cunt started to betray her. Whack!  She could feel it start to flex and quiver every time the towel whipped down on her body.
	The whipping stopped.  Without a word, Helmut climbed over her.  He took a buttock in each hand and spread them as far apart as they would go, leaving her butt hole exposed.  Suddenly Tessa felt something at her anal opening.  She knew what it was and what was to come next.
	With one motion of his hips that made the bed bounce slightly, Helmut drove his greased cock into Tessa's asshole in one continuous penetrating push, not caring whether or not he was hurting her.  With her ass greased the way it was, she couldn't offer any resistance.  Helmut rammed his pole into her bowel in one smooth motion, stopping only when his groin rested up against her buttocks.
	Still without a word, he began to beat his cock in and out of her, sometimes fast, other times slowing as if he were savoring the experience.
	Tessa was thankful that he had the decency to use a lubricant.  With the pounding he was giving her backside, he would have torn her up especially since she was still sore from Jerry's fucking her up the ass the day before.  The way it was, Helmut's cock was hurting her, making her feel uncomfortable, and distending her bowel more than a butt fuck usually did.  Normally to take it up the ass, Tessa would be on her knees, her ass up in the air, giving the guy easy access to her asshole.  Because she was flat on her stomach, Helmut's cock was not aligned, and it tore at the anal opening more than usual even with the lubricant.  When his cock was stuffed all the way up her shit chute, Tessa felt as though her whole gut was filled and she would burst.  She felt as though she could have fondled his cock through her stomach wall if she had a hand free to try.
	None of this bothered Helmut.  He kept banging away at Tessa's asshole, minute after minute.  He was in no hurry.  His ball had been drained once already and he could go on for some time before they exploded again.
	Before when he wiped her with the towel, Tessa's pussy began to respond, but now she felt no hint of arousal.  Her asshole was taking too much of a beating.  It was beginning to hurt too much.
	With a quiet whimper, Helmut stopped, his cock buried in her.  Tessa felt it expand, stretching her anal ring and jerking in her bowel.  
	"Uuuuuhhh!" was all that came out of his throat.  She felt his groin jerk several more time.  He was cumming in her.
	Moving his hips back, letting his cock come half was out of her asshole, Helmut began to slide in and out of her, this time leaving a load of cum in her ass.  Stroke after stroke, load after load, she knew her chute was being filled with cum.	
	Again he froze, his cock up her asshole.  He held himself for a few seconds, then collapsed on top of her.  He was done.
	For a minute, the two damp bodies just lay there, each one recovering from the fuck.  With a grunt, Helmut rolled off of Tessa, extracting his cock as he went.  He lay on his back regaining his breath.
	"You know Tessa, you're great," Helmut said between breaths.  "You okay?"
	When there was no response, he looked over to her.  
	"Oh, sorry," he said as he pulled the tape from her mouth.  "You can take the cloth out.  I hope it didn't cause you any problem."  He pulled her arms free of the ropes.
	Pulling the cloth out of her mouth, Tessa looked at Helmut.  "Helmut, you're a lousy bastard, you know that?"
	"Come on, you liked it.  Admit it."
	"You're nothing but a fucking creep.  My whole body is going to be full of welts, and I'll bet my asshole is bleeding, you piece of shit.  I hope you had your fun, because I didn't."
	Reaching over to his pants, Helmut extracted a roll of bills.  Pealing off several, he handed them to Tessa.
	"Yeah, I guess I was pretty rough on you, but damn it, you really drained me.  God damn, that ass of yours is tight.  As far as the beating, shit honey, there's enough dough there for a good massage, enough to cover your business loses for a few days, and enough to make a good profit.  Then, bingo, you're back to being your old self.  So quit bitching, you'll do fine.  And, yeah, Jerry will get his contract.  Who knows, maybe he can put you on retainer with his firm you're so fucking good."
	Tessa stood shakily and looked down at Helmut.  She could feel the blood leaking out of her asshole.  Yes, he did do damage, the fucker.
	Taking the money, she headed for the bathroom hoping to make herself presentable enough to return to her building without make the doorman's eyes widen.

	Later the next day Tessa's phone rang, the business one.  She didn't care who it was, she was shutting down for a day or two, and the john on the other end of the line would just have to settle for beating his own meat off as far as she was concerned.
	"Hello."
	"Hi, Tessa, it's me, Jerry."
	"What do you want, Jerry?"  Tessa kept her self under control though she wanted to tell him to drop dead after last night.
	"To thank you.  Helmut signed.  We did it, and I want to thank you.  You did great, honey."
	"Listen to me, Jerry.  You ever send a mutt like that to me, and I'm going to kill the both or you, you understand?"
	"Tessa, what the hell are you talking about?"
	"You want to know? Okay, I'll tell you."	Tessa related to Jerry the events of the previous evening, the whipping and the sodomizing of her ass.
	"And when I use the term 'sodomizing', I'm not talking like you and I, Jerry.  This fucker ripped my asshole until it bled.  Do you hear me?  I'm bleeding from my ass because of that bastard."
	There was a silence on the other end.  Then, in a low voice, "Tessa, I'm so sorry.  I didn't know the guy was weird in bed.  Hell, how am I supposed to know something like that?  Please forgive me."
	"Look, sweetheart, you know I think the world of you," he went on, "so I want to make it up to you.  You know that I won't do anything to harm you.  Let me send you something, we'll call it a bonus for taking care of the bastard the way you did."
	"Jerry, I know it's really not your fault, but all I got to say is that it had damn well better be a fucking big bonus if you ever want to see me again, God damn it.  I paid dearly last night."
	"And I'll pay dearly now, Tessa.  Trust me."
	Several hours later, Tessa thanked the messenger as she let him out.  True to his word, Jerry sent a 'bonus' over.  Opening it up, Tessa smiled.  
	Life was good.  Jerry's initial payment, plus Helmut's last night, and now this one, yes, life was good, very good because Jerry's bonus was in the five figures.  Whatever Helmut signed, Jerry's firm must have made out like a bandit.
	Tessa smiled as she headed back to her bedroom to continue dressing for this evening's dinner with Dan.  She'd have to wear a high-necked dress to cover her welts, but she could let her arms remain bare.  They were just fine.
	And so was life.
	
To be continued . . . 

