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Sold! One Butt Cherry.
I looked down at the woman on her knees in front of me. She was middle-aged with crow’s feet at the corners of her eyes and had short, dark hair. She had been pretty and was still attractive now but was no longer pretty. She was wearing her jeans. They were loose across her wide hips, ample butt and chubby thighs, thanks to the weight she had lost recently. Her blouse was off, as was her bra. Both were over the back of one of my dining room chairs. Her belly was not as flabby as it had been in the past but it was still soft and pudgy. Her tits were big, floppy fat girl titties with big dark areolas.
Her name was Samantha. She was a social worker with a gambling problem, an old flame of mine from years and years ago; and about this time three to five times a month she was in this position with her head in my lap sucking my dick. Her spendthrift ways and her bad luck at the slots always had her strapped for cash. She had two kids and a good for nothing husband to support and I got a kick out of giving a member of The Department of Family Services money to blow me.
Why she had stopped blowing me before I got my nut was puzzling. Sure she hated it when I came in her mouth but she had learned to live with it and took her mouthfuls of hot cum with only mild looks of disgust on her uptight face.
“What the fuck?” I asked her. “You’re not done!” I reached for her head. Every once in a while she has an attack of conscience and I have to force feed her my dick until she comes back around.
“Wait”, she said. “Please, I have something to ask you.”
“It better be good.” I put my hand on top of her head. I tilted her head back and laid my dick across her lips. It bounced on her mouth as she talked. She looked absurd which I found to be hilarious. “Speak.”
“I’ve got a bigger problem than usual. I need more money.”
“I don’t know what to tell you”, I said. “I’m not paying any more for you to suck my dick and your pussy is not worth it. I’ve been there.”
“Come on, Hal. I’m desperate.”
I shook my head and tapped the head of my dick on her lips.
“Please, Hal? We could call it down payments on future blowjobs.”
“I don’t know. Hell, I might get tired of your middle-aged mouth before they’re all used up.”
“Please, Hal. I’ll come over whenever you call. I promise. I’ll come over and blow you whenever you want me to. Come on, Hal. I’m going to lose my car.”
I put the head of my dick in her mouth. “Lick.” I considered as her tongue swirled over my sensitive tip. “How much do you need?”
When she told me I whistled.
“Oh shit! No way! No fucking way! I ain’t paying that much in advance. You ain’t fucking worth it.”
“Come on, Hal! I’m desperate! I’m going to lose my car!”
“Fuck. Get that cock back in your mouth while I think.”
Samantha’s lips slid up and down my dick. While my dick is not huge, it is an impressive eight and a half inches with a wide girth, more than a mouthful for most women. Samantha was no exception. She could not reliably deep throat me but she managed good depth and lots of head bobbing speed. Besides it was a thrill having some other guy’s wife and a mother of two on her knees pleasuring my cock.
Still, I wasn’t paying any more for her blowjobs. Why pay more for what I was already getting? Unless I could get something else I wanted. Something she wouldn’t normally give up, something she had never given up.
“There is something you’ve got that I’d pay for.”
She popped my dick out of her mouth. “What?”
“But I’m not going to pay for just one shot at it. I want a whole night.”
“What?” She was starting to sound nervous.
I bounced my dick on her mouth. “You’re desperate, right?”
“Y-yes.” Definitely nervous.
“All the money you need and I get an entire evening with you.”
“What do you want to do?” Her voice wavered.
“I want the one thing I’ve never had from you, that anyone has ever had from you.”
“Your ass cherry.”
Samantha’s face went pale. She had always been deathly afraid of anal sex. She hates the very idea of any kind of pain and, her oral skills notwithstanding, she was a prude when it came to sex. The possibility of a dick in her asshole was not even a chance with her.
Until perhaps now.
“That’s what I want. An evening with no holes barred.”
She didn’t say anything. Since she wasn’t using her mouth, I did. I pulled her head back down, slid my cock in and guided her head up and down at a leisurely pace.
“How soon do you need the money?”
“Soon, real soon. My car payment is late.” She had raised up to speak. I pressed her head back so she could continue sucking me off. She hadn’t actually agreed to do anything but I discussed the topic like it was a done deal. I mean, what else could she do? She needed the money and either she peddled her fat ass or she lost her car.
“Can you show up here tomorrow night at six?”
“I was going to dinner with my husband and kids but I could get erotik film izle out of it. But I’m not–.”
I cut her off by pushing her mouth back onto my dick. She made a slight noise of displeasure that I squashed by started her bobbing with a firm hand on her brunette head.
“Okay, here’s the deal. You show up here at six dressed for work. Skirt, heels, hose, blouse with Family Services emblem. You stay until I’m done but not longer than nine and I pay you when we’re through.”
“I’m not sure if I—.”
“In that time I get you to use as a big fuck doll, any and all holes.”
I rubbed my dick head on her lips.
“That’s the only way I’ll do it”, I told her. “Go somewhere else and see if you get a better deal. You won’t get that much all at once but if you’re willing to work that mouth for it I can put you in touch with some guys I know. They might not be as discreet as I am and it will take quite a few blowjobs to raise the kind of money you need.”
I guided her head forward and she opened her lips.
“That’s a good cocksucker. Suck it dry.”
She licked her soft tongue all over my shaft and, opening her warm, wet mouth, engulfed my dick. She pumped her head up and down using lots of tongue and making the slobbering noises I love to hear.
“Fuck yeah”, I moaned. “Suck that dick. Work for your cum. Work for your money.”
I leaned back in my seat to get a better look at the face of the married mother of two bouncing up and down in my lap. She may have been past her prime but Samantha sure looked good with my dick sliding in and out of her mouth.
“Suck it, whore. That’s what I pay you for!”
Samantha backed up until only the head of my dick was in her mouth. She sucked on it until her cheeks caved in and then she pulled it out of her mouth with a loud popping sound. She did that several times because she knows I like it and then went back to driving her mouth up and down on my cock. I thought about the husband she had at home. Did she work as hard at sucking his dick as she did on mine? I highly doubted it. I don’t think he gave her the proper incentive.
“Fuck yeah! Work that whore mouth!”
My balls had started to stir and reminding her of what she was sped up that wonderful tingle. It was almost time for Samantha to get her mouthful and her money. Back when Sam and I were a couple—way before hubbie and the two kids—she had refused to swallow my cum. She was a good cocksucker even back then but every time she tried to swallow a load she choked on it and spewed it all over the place. She would let me cum in her mouth and then run for a trashcan afterward. But when we entered into our current arrangement I wouldn’t pay unless she swallowed my load and money is a good motivator. Of course I had to refuse to pay on our first two meetings but eventually she learned to force the sperm down and keep it down.
I’m sure she didn’t do that for her husband.
“Here it comes! Earn your money, whore!”
I grabbed her head in both hands and drove my hips forward, driving my cock toward the opening of her throat. She opened it as much as she could and swallowed rapidly. She swallowed as fast as my spunk filled her mouth but as fast as she gulped it down she couldn’t prevent the taste from filling her mouth. She hated that taste and once asked me for mouthwash when we were done. I lied to her and told her I was out. I like for her to drive home with my cum on her breath.
“Swallow, whore, swallow!”
I finished cumming in her mouth and fell back in my chair. Samantha put a hand over her mouth and threw her head back. Her throat worked furiously as she forced the sticky wad down. When it was down for good she wiped her lips with a finger and looked at me expectantly.
I pulled my pants up and reached for my wallet and she went for her blouse and bra. We met at my front door. She was dressed and I had her money in my hand. “You earned it”, I said, handing her the bills. They disappeared into small black purse.
“See you tomorrow”, I said.
Samantha couldn’t look me in the eye and slipped out without saying a word.
At ten minutes to six her car pulled up in front of my house. She sat there until two minutes of and then started her car. It idled for nearly a minute before she turned the engine off and got out to fast walk to the front door. She knows I hate it when she’s late.
A precisely six she knocked on my door.
I opened it with my best I told you so grin.
I led her to the bedroom, admiring how surprisingly good she looked. Her face was made up well and her sagging middle-aged tits were cupped nicely in a good bra and her light blue blouse shirt curled under their nice curves. As per my instructions it was a state issued blouse and the Family Service logo over her left breast. Her legs were clad in black hose, looking chubby but trimmer than usual. Her ass though was still big and round. It was too big for most men—me included—but my eyes couldn’t stay off it. Her black skirt was tight across her fleshy rear and the high heels film izle she wore gave the chubby globes a seductive roll.
That big butt was virgin territory and I was about take it by storm.
That virgin ass was mine. I was paying good money to pop that big butt’s cherry.
I halted her just inside my bedroom door and sat on the bed facing her. “Let me get a look at what I’m buying”, said to her. She had lost some weight, could stand to lose some more but wouldn’t. She never did. She would always be my chubby girl. “Turn around so I can see the ass I’m paying so much to tap. That’s it. Push it out. Yeah, that’s it. Damn, that’s a big ass!”
I had her face me again and began to ask her questions, to interview her. She was too nervous to wonder why, that and she was used to strange behavior from me. She knew I liked to drag things out, to torment her. She knew this but yet she always came back. Sometimes I was not always sure it was the money she came back for. I didn’t pay her that damn much.
I started my questions for the cameras I had hidden around the room.
“What is your name?”
“Where do you work?”
“Department of Family Services, Child Welfare Division.”
“And why are you here to see me this evening?”
At that question she fidgeted and flashed me an annoyed look. “You know why I’m here.”
“Yes, but I want to hear you say it.”
“Hal, please? Can we just do it?”
“No. I’m paying so we do what I want or you can walk that fat virgin ass to somebody else and peddle it to them. Do you want to do that?”
“No”, she replied with lowered eyes.
“Then answer me. Why are you here?”
She sighed resignedly. “To sell you my anal virginity.”
“So, you’re a social worker peddling her big round virgin ass.”
“And what does that make you?”
She frowned. Hearing me call her the name was one thing but admitting it by saying it aloud was too much.
“Say it. What does that make you?”
Her tongue fumbled but got the word out. “A-a whore.”
“What are you? Say it as a sentence.”
“I’m a whore.”
“I’m a whore.”
“Is this the first time you’ve sold you body?”
“What else have you sold?”
“Blowjobs. My mouth.”
“So, you’ve been a mouth whore and now you want to be an ass whore. Is that right?”
“Then let’s get you out of those clothes and get my dick in your butt. Put down your purse and get out of that skirt.”
She put her purse on a chair and unzipped her skirt. She stepped out of it and laid it on the back of the chair. She stood, awaiting further instructions. She knew me well enough not to do anything without being told to do so.
“Lose the hose but keep your high heels on.”
She slipped out of her hose and stepped back into her heels. I glimpsed the front panel of black panties but her blouse hid them.
“Put your back to me and take off your blouse and bra.”
She did as she was told and her big panty clad butt came into view. It was wide with overfull cheeks but it was virginal and it was mine.
“Take your panties off slowly. Bend over while you’re doing it. Show me what I’m buying.”
She bent and her panties went down. She stepped out of them but stayed bent over, wearing nothing but her high heels. I stepped close and rubbed those pudgy cheeks. They wobbled under my fingers. “Too fat. I wouldn’t give you a dollar to fuck this ass if it wasn’t virgin.
I pinched a plug of flabby butt flesh between two fingers, squeezing hard and twisting. Samantha yelped and I laughed.
“Reach back and spread your ass open”, I told her. “Let me see that tight little target.”
After a pause she reached back with trembling fingers and told her butt cheeks in hand.
“Spread them, whore!”
She did, exposing her anus. She may have had a fat ass but her butthole was a tiny pink dot easily covered by a fingertip. Getting my sizable dick in there was going to take a lot of effort and she didn’t know it but I wasn’t planning on using much lube.
I wanted her to feel the pain.
I pulled her up by her dark hair and pressed her face to the wall. I rubbed her big butt. I slapped a pudgy cheek and watched it wobble. I smacked her again harder, hard enough to leave a red mark on her left butt cheek. Samantha yelped again.
“I’m going to pound my big cock up your ass”, I hissed in her ear. I tapped her butthole. “I’m going to make you scream.”
She whimpered and her little puckered anus contracted even more.
“But you need to be properly labeled first. Get me the red lipstick from your purse.”
She got it for me with a questioning expression on her face. I took the tube and put her back against the wall. “Face the wall and stand still.”
I uncapped the lipstick and wrote one word on her back in big, red letters.
In the small of her back I wrote the amount I was paying for her butt cherry. Underneath seks filmi izle it I drew an arrow pointing down. I turned her to face me and under her fat, drooping tits I again wrote: WHORE.
Above her tits I wrote the price I paid her to suck my dick and drew an arrow pointing to her mouth.
Samantha’s pubic hair is a compact triangle of very dark densely woven hair. It always looks trimmed but I’ve never known her to manicure it. Above it I wrote WORTHLESS and drew an arrow pointing into the tight curls.
I turned her to face the tall oval mirror in the corner. She let out a small gasp and her face colored when she saw her reflection. “Don’t look down”, I said to her. “Look at it.”
I pointed to the word under her tits. “What are you?”
“I’m a whore.”
I spun her around and had her look over her shoulder at her painted backside. I pointed to her back. ‘What are you?”
“I’m a whore.”
“Good girl. I’m glad that you’ve learned your place.” I undid my belt and whipped it through my belt loops. I came out with a whizzing sound and I wrapped it around my right hand. Samantha looked at it and emitted a quiet gasp. “Shush. Be quiet or I’ll make you cum while I’m spanking your fat ass.”
I reached around her with my left hand and ran a finger through the dark curls of her pubic hair. I pressed on the tender button hidden there and Samantha bit her lip to keep from gasping even louder. She rarely orgasms, can only do so after intense clitoral stimulation. For some reason this embarrasses her tremendously and she usually doesn’t cum or fakes it. As far as I know I may be the only man she has ever had an actual orgasm with. Tonight however was not about her orgasm. It was about mine, so I took my hand away and smacked her on the big butt with the belt.
Samantha yelped and her butt cheeks clenched. She clamped her mouth shut when I smacked her the second time and I hit her again and again. I lashed the belt across her butt ten times, leaving ten red stripes on her big round curves. She was trembling and holding in tears by the last one.
I paused a moment and then gave her ten more lashes. She whimpered loudly once at slap fifteen but kept quiet after that. Her butt was rosy red and radiating warmth. I dropped my belt and touched her butt. She flinched at the touch of my fingers on her pain reddened cheeks.
“The best that ass has ever looked”, I said. “Get in your knees and do what you’re good at.” I undid my pants and had my dick out as her mouth dropped and engulfed it. “Aaaahhhh.”
Her lips slid up and down my shaft. Her tongue caressed its length. She worked her whore’s mouth like the expert cocksucker she was.
“Oh my god, you missed your calling. Anybody can be a social worker but not every woman is a natural born cocksucker.”
Her head bobbed rapidly. She slobbered loudly.
“If you need some extra money after this let me know. I’m sure I can pimp that mouth out for you.”
I put my hand on her head and shoved it down on my dick as far as she could take it. There was still more dick so I pushed until her lips was pressed into my pubic hair. Samantha flexed her hands at her sides as she began to choke. She wanted up but I kept her down where I wanted her. Her face creased and her throat convulsed.
I jerked her mouth completely off my dick and spit in her face. My loogie landed on her forehead. She flinched and looked disgusted. This was the first time I had ever spit on her, but then tonight was a night of firsts in our bizarre relationship. I laughed at her discomfort and spit again, hitting her on her right cheek. I dragged up a good sized of spit blob and splattered her nose with it.
“Open your mouth, whore.”
Samantha let out one of her characteristic whines but did as she was told. I spit past her open lips. “Swallow it. Oh yeah, that’s a good bitch. Now wipe the rest of that spit on your face up and stuff it in your mouth.”
She cleaned her face as instructed and waited for further directions. I took her by her short hair and pulled her to her feet. Sammie is barely over five foot and I towered over her. “Time to give up your ass, girl.”
I bent her over the foot of my bed. She was short but her high heels made her just the right height. I moved into position behind her and she squeezed handfuls of the bed covers and pressed the side of her face to the bed. I set the saliva slick head of my dick to her tiny puckered opening. She whimpered in anticipation of the coming anal invasion.
“Don’t tense up”, I said. “Relax and it will go in easier.” If she relaxed I couldn’t tell it. I leaned in, pushing with my hips. Her butt hole was a tight little knot. I drove into it, indenting it but not getting in. “Damn it, Sammie girl, stop fighting!”
Frustrated, realizing that I was going to have to resort to lube after all, I rammed my cock at her closed hole.
“I’m no-oooottttt!” Samantha’s puckered opening finally and my cock shot up her ass. My dick plunged into her bowels in one lightning fast drive. Her tight unplumbed rear tunnel was stretched wide open in an agonizing instant. The sudden painful shock drove the air from Samantha’s lungs.
And I still a couple of inches of dick to shove up her tight ass.
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