Jill Ch. 03

Story Info
Real Estate Agent Jill crosses the line.
3.3k words
4.15
68.6k
3

Part 4 of the 11 part series

Updated 11/01/2022
Created 06/24/2011
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Jill woke up to find her husband already showered, shaved, and dressed. The three-day suitcase was packed and placed next to the door.

"I thought you had the next week home?" Jill asked.

"I thought so, too, but I got a text an hour ago. Looks like I'm going to Barbados." Brian said with a grin. "Wanna go with me?"

"You know I do, but I can't. I'm still trying to get all the party-favors together for the bachelorette party. Plus, I'm supposed to show a few houses today. I'm not sure I can even walk." Jill sighed as she pulled back the sheets.

Brian stared at her recently-shaven pussy. Last night was the first time in their marriage that she had done that. Last night was also the first time she had asked him to have anal sex with her, and the first time she had thanked him for doing it. He wasn't sure if he should be delighted or worried that she'd crossed over into some new territory.

"Have you been reading Cosmo, or something?" Brian asked timidly.

Jill smirked.

Jill's pussy and asshole were still tender from the night before. She decided to wear a blouse, bra, and skirt, but no panties.

Brian had put new sheets on the bed last night while she was in the shower. It appeared that anal sex could be a little messier than one would be led to believe from the movies. She carefully carried the laundry downstairs, started a load, and made a pot of coffee.

Jill's daughter, Andi, smelled the coffee brewing and decided to join her parents for a cup.

"I thought you were staying by your aunt's?" Brian asked nervously.

"I am, but I had to come home and get my swimsuit and clothes." Andi chirped.

"When did you get home?" Jill asked.

"Last night. It was pretty late. I was so tired; I must have passed out as soon as my head hit the pillow. I don't think an earthquake would have woken me up." Andi smiled.

Jill looked at Brian, signaling relief. Brian finished his coffee and kissed Jill deeply before walking out the door.

"Wow, that was a good kiss!" Andi commented. "Are you guys taking Viagra or something?"

"No dear," Jill was quick to respond. "That's not necessary for your father and I – yet," Jill smiled.

"So, how's the scavenger hunt going?" Andi asked.

"What are you talking about?" Jill said, defensively.

"Oh, come on. I know you're buying the party favors for the bachelorette party." Andi said shyly. "Dildos, right?"

"Nobody was supposed to know!" Jill's face reddened. "How did you find out?"

"Oh, I have my ways." Andi grinned. "Can I see what you have so far?"

"Absolutely not, Andrea!" Jill almost dropped her coffee cup. "You'll just have to wait until the party like everyone else, okay?"

"Okay, mom." Andi smiled and carried her coffee back to her bedroom.

Jill's first client was an older gentleman in his late sixties. His wife recently passed away and his house was too big without her. He wanted to sell his house and move into an apartment or condominium. Jill found several interested buyers for his house, but he couldn't seem to make up his mind on a condo.

"Mr. Roth, we've been to the best three condominiums in town." Jill pleaded. "Surely, there's something that sticks out in at least one of them?"

Mr. Roth couldn't help but stare at Jill's legs. He had behaved himself until now. He wasn't sure what it was about her, but he found himself unusually aroused sitting next to her in her car.

"Which one do you like the best?" Mr. Roth asked.

"It really doesn't matter to me. I want you to be happy. That's what you're paying me for – whenever you decide." Jill pulled the car in front of the last condominium she would show him that day. "I hope you find something you like, soon, or I'll get pulled from this job and one of the other guys from the office will take over."

"This is the most expensive of the one's you've shown me, isn't it?" Mr. Roth asked.

"Yes, Mr. Roth. It's in the nicest neighborhood, great location, and great resale value." Jill answered, turning her back on him while she turned on lights and opened doors and cabinets.

When she turned around, Mr. Roth unzipped his pants and pulled out his half-erect member.

Jill was shocked, and somewhat amazed at his... audacity.

"Mr. Roth? What are you doing?" Jill asked, already knowing the answer. So many of her colleagues had been faced with this before, she knew it was only a matter of time when it would be her turn.

"You said it yourself; I'm paying you to make me happy. You'll get $10,000 commission, easily if I buy this place, right?" Mr. North asked as his penis thickened before her eyes.

"Yes, but..." Jill stammered. She wasn't exactly sure what he had in mind.

"But nothing. Make me happy." Mr. Roth pointed his erect prick at her.

Jill hesitated. She had thought Mr. Roth to be a classy gentleman up until now.

Her phone rang.

Another agent was on his way to show the condominium and would be there with his clients in ten minutes. Jill passed the information to Mr. Roth, hoping he would put himself back in his pants. Instead, he tugged at his swollen tool.

"Guess you better hurry, if you really want me to buy this place." Mr. Roth grinned.

Jill quickly walked up to Mr. Roth, her high heels clicking on the bare floor.

The skin on his shaft was soft. She lightly caressed his testicles while stroking his cock with her other hand.

"I'm not happy, yet." Mr. Roth whispered.

Jill hiked up her skirt so it wouldn't split, and squatted on her high heels. Mr. Roth didn't seem to notice that she wasn't wearing panties. As soon as Jill placed the head of his dick in her mouth, he closed his eyes and grinned.

"Now, I'm starting to become happy." Mr. Roth smiled.

Jill had two other showings that day, and another agent was going to be there in less than five minutes. She couldn't afford to have this dirty old man come all over her face and hair. She knew she would have to swallow whatever his sixty year-old his balls produced. Her head bobbed quickly, but almost precisely.

Mr. Roth's orgasm was quick and intense. His load filled her mouth immediately, and Jill struggled to swallow the first spasm. When he realized Jill was swallowing his come, his legs became weak. Jill looked up after sucking the last of his semen from his deflating erection and her face filled with panic.

"Oh my god, tell me you're not having a heart attack!" Jill cried out. It was only after she stood back up that Mr. Roth noticed her lack of panties and her shaved pussy.

"I don't think so, but now that I've seen that pretty cunny of yours, I'm not so sure." Mr. Roth panted.

Jill pulled her skirt down and straightened her blouse. She checked her make-up in the bathroom mirror. "Not too bad." Jill thought. "Most of my lipstick is around the base of his cock, no doubt."

Mr. Roth had barely finished zipping his fly when the other real estate agent and clients walked in.

Jill walked in from the bathroom, having a little color in her face as if she had been running.

"I'm sorry, but I think you're too late on this one." Jill said to the other agent. "Mr. Roth, here, is buying this place, isn't that right?" Jill smiled at Mr. Roth.

"Ummm, well, I have to make an offer." Mr. Roth said.

"Nonsense, you just told me that I made you very happy – by finding this place – and you'd have to have it, no matter what the price." Jill smiled at Mr. Roth again, licking her lips ever so slightly. "I'm late for another showing, but the guys at the office will be able to walk you through the forms. I'll call ahead and let them know you're on your way, Mr. Roth!"

Jill walked up to Mr. Roth on the way out and kissed him quickly on the mouth. Her back was to her colleague and the other buyers. They couldn't see that she had stuck her tongue in Mr. Roth's mouth. Her breath smelled of his come.

"Remember me the next time you need a real estate agent. I really enjoyed working with you!" Jill said as she walked out the door, rubbing her thumb and fingers together making the money sign.

"How can I forget?" Mr. Roth whispered to himself.

Jill felt empowered. She had just made $10,000.00! She called her next clients and was relieved to find that they had to cancel that afternoon, but would like to schedule something next week. That gave her three hours until her next showing. She considered going back to the office, but then she would have to tease Mr. Roth again, and she wasn't sure if his heart could handle it.

Instead, Jill drove to the last of three adult bookstores in town that carried the so-called party favors for the bachelorette party.

When she had called days before, the voice on the other end of the phone was rude and crass. Jill had felt humiliated when he had hung up on her. Had she not had such a successful morning, she might have considered driving several hours out of town to find the last two dildos on her list.

The previous place she visited was rough in it's own way, but the salesperson, Sammy, was nice to her. He might even have been gentlemanly, if such a thing was possible in an adult bookstore in a bad part of town.

The last possible place in town that might have what she needed was located in a desolate area. All the other businesses had closed down, except for a coin-op laundry, a bar, and a gas station that no longer sold gas.

It was early, so there was a chance the place wouldn't even be open. To Jill's surprise, it was not only open, but also it had about ten customers.

Andi had waited until she was sure her mom would not come back to the house before she went into her parent's room. Her mom had been hiding Christmas and birthday toys under the bed for years, so it came as no surprise that Jill would put the party favors under the bed as well.

Andi pulled several of the toys from under the bed and laid them out, arranging them by size and color. "Not bad, mom. You almost found all of them." Andi smiled, removing one of the toys from its cardboard packaging.

Andi had promised her mom that she would remain a virgin until she was married, and she had kept that promise – to a degree. She was not only the smartest girl in her class, but she was the smartest girl in her high school. Her grades in college have been straight A's. As far as her parents were concerned, she was the perfect daughter.

Andi was also very attractive in her own way. Her face was pretty, but plain without makeup. Her strawberry blond hair was blonder than strawberry, and her freckles were more noticeable than on her redheaded mother.

Her breasts were small, much to her disappointment considering Jill's bosom.

Her legs, though, seemed perfectly sculpted just like her mother's. She had been on the swim team throughout high school, tanned regularly, and never smoked, drank, or experimented with drugs.

Her only vice... boys.

No penis had ever entered her vagina. Tongues, yes. Fingers, a few. But no penises.

The same could not be said for the other orifices in her body. At eighteen, she had no less than twenty dicks in her mouth, though not at the same time.

Her first "serious" boyfriend had licked her pussy so well; he could bring her to orgasm in less than three minutes. He was so consistent in satisfying her, that she felt obligated to let him put his penis in her mouth.

She had absolutely no idea what she was doing, at first. She got better, though. Within a month, she was so good at giving head; she began trying out her new skill on more casual boyfriends – the ones that normally received a kiss on the cheek after the movie and dinner.

Some of the boys wanted more, and even complained to some of her friends that she wouldn't put out. She was firm in her promise to her mom. But her mom didn't say anything about anal sex. For the boys she really liked, she offered her ass. Most of the boys gladly accepted the alternative to her pussy. A natural quick-learner, she became as comfortable with anal sex as she was giving blowjobs.

Andi's grandmother passed away years ago, but Andi bought enemas "for her grandma" at the local drugstore ever since starting college. At least, that's what she told the pharmacist. None of the boys having anal sex with Andi were very big, so her vaginal virginity remained intact – as far as she knew.

She stared at the "super-dong" in her hands.

Although tempting, Andi decided to not lose her virginity to a toy.

She put the large dildo back in its box. Her clit throbbed. "Patience," Andi consoled herself. She'd have a mouth on her pussy before the night was over.

Jill was glad that this was the last adult bookstore she was going to patronize.

Had she gone to this location first, she doubted she would have had the nerve to go to any others.

There weren't many books or magazines on the racks.

There weren't many sex toys, either.

There was very little fetish porn, outside of interracial, gangbang, and the gay versions of each.

Jill's calves flexed as she reached up for one of the toys remaining on the list.

Her legs didn't go unnoticed.

"You sho' are fine, little lady," one of the patrons complimented.

"Thanks." Jill said without looking at him. "Could you get this for me?"

"Sho, little lady." The patron effortlessly reached up and handed Jill the large dildo.

"Mine's bigger."

Jill turned and looked at him. He was easily six feet tall and 250 lbs. She could barely make out his facial features, but could see his glowing white eyes and teeth when he smiled. She accidentally rubbed his fingers when she took the toy from his hand. They were larger than any fingers she had ever seen.

"I believe you." Jill smiled, not sure what else she could have said. "Would you mind helping me find one more?"

"You don't need no toy, little lady. I gots what you need right here." The patron reached out and grabbed Jill's forearm, placing her hand on a bulge that stretched from his groin halfway down to his knee. Jill was scared, but she also couldn't help but try to get her hand around the bulge. It was as thick as a soda can.

"Thanks for the offer. Really. But I'm on my lunch break and I'm just trying to get these toys for a bachelorette party. I don't actually use these things." Jill confided.

The storeowner interrupted their conversation.

"Bitch, you either buy somethin' or go trick somewhere's else!"

Jill recognized the voice as the man that hung up on her days prior.

"You think I'm a prostitute?" Jill asked. She was almost flattered, but she also knew that if she cowered now, she would have a hard time finding the last dildo on the list. "I'm trying to buy some goddamned toys for a bachelorette party. Will you let me do that? I promise I'll never set foot in your store again. Okay?" Jill held out her hand and showed him the list.

"Awe shit, we got us a firecracker. A redheaded firecracker!" The storeowner smiled bearing several gold-capped teeth. He was skinny, and had it not been for the wrinkles in his face, he could have passed for a teenager.

He looked at the list and pretended to look concerned.

"Yes, missus, we got dat one, but only one left." He joked.

"Great. I'll take it and be on my way." Jill crossed her arms, being careful not to drop the toy she was able to find.

"I don't think so." The storeowner said. "I reserve the right to refuse service to anyone. I think you need to learn some respect."

"Are you fucking kidding me?" Jill just wanted to get out of there.

"Okay. Tell you what; you can buy these rubber dicks for $500 each today, or you can come back tomorrow with some respect and I'll sell them to you for the sale price of $50." The storeowner paused proud of himself.

"I'm not paying a thousand dollars for a couple of dildos." Jill sighed and handed the toy in her hand back to the well-hung patron.

"Then get the fuck out my store, bitch!" The storeowner tried to kick Jill in the behind, but missed and caught his foot on a magazine rack.

Jill quickly turned around. She wanted to ask why he was so angry, but decided to give him something to think about, instead. She reached down to the hem of her skirt and quickly raised it, flashing her hairless pussy for barely a second. "Respect this!"

She turned around and walked to her car.

Before the door closed behind her, the well-hung patron called out, "Hey Red, you come back tomorrow, and I'll buy those toys for you!"

The other men in the store smiled at each other while the storeowner looked at the dildos and laughed.

Jill quickly drove away, meeting her last clients of the day in front of the ranch house in the good school district. She didn't notice the police car that followed her out of the neighborhood.

Her clients were more exhausted than Jill, and didn't like the house.

"Well, the day started out well." Jill sighed as she drove home.

The house was quiet.

Andi was at Jill's sister's house.

Brian was on a plane headed for Barbados on a business trip.

Jill was exhausted.

She opened a bottle of wine, thinking she'd only have one glass before falling asleep.

She was on her third glass by the time she walked up to the bedroom.

Jill collapsed shortly after placing the glass on the nightstand.

She dreamt of the well-hung patron holding her in his large hands. Probing her with his large fingers. Fucking her with his unbelievably large cock.

Jill woke up to find her sheets wet. She quickly stood up, but soon realized she was naked – and still a little drunk. She didn't remember taking off her clothes.

"Why didn't I just pay that asshole $1000 for those two dildos?" Jill said to herself. "It's not like I didn't just make $10,000 blowing Mr. Roth."

Jill pouted. She looked at the clock on the dresser.

1:00 a.m.

Jill rummaged through her closet and found a short black leather skirt she had bought for an office "'80's" themed party, a black lace push-up bra, and a white, thin-mesh blouse. She thought about stockings and a garter, but she could only find one fishnet stocking. She didn't bother with panties – not because her pussy and asshole still hurt – but because she didn't think she needed them. Besides, she would just have to take them off, anyway, if she went through with what she was thinking.

When she stepped out of the shower, she felt more alert, but still determined. She carefully applied her make-up and fixed her hair, and then looked at herself in the full-length mirror. She thought she was "reasonably pretty" most of the time. Now, for a 38 year-old wife and mother, she was "fucking hot."

"I'm really going to give that rude, mean, gold-toothed asshole something to remember." Jill winked at herself, and then picked up the phone to call a taxi.

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3 Comments
slave_arianaslave_arianaalmost 12 years ago

I'm beginning on getting addicted to your stories :)

AnonymousAnonymousover 12 years ago

The wife will get knocked up by all her nigger lovers won't she? And then the husband can divorce the bitch and find someone that doesn't fuck around while he keeps them in lifestyle they want.

sheransheranover 12 years ago
excellent...................................

nice story keep up da good work:)

please continue jill

itz a mega hit

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Jill Ch. 04 Next Part
Jill Ch. 02 Previous Part
Jill Series Info

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