How I Became Mayor Ch. 07

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Dirty politics and Jill's first time anally.
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Part 7 of the 8 part series

Updated 11/01/2022
Created 06/07/2005
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notnaive
notnaive
122 Followers

Chapter 7 - The Countdown to Election Day

Jill turned out to be even better than I hoped. Not only was she beautiful, engaging, and fun to be around, she was very organized, savvy, and intelligent. After a week, I decided that she would be in charge of my campaign for mayor. I introduced Jill to outgoing mayor Thompson, and the two of them immediately started hatching schemes. It was exciting watching her work to make me the next mayor.

My main competition for mayor was one of the other council members, Mr. Trenton Grasso. He was an oily-looking, slick-talking schemer who had been on the council for a long time, and was only waiting for the popular Mayor Thompson to retire. He saw himself as the people's next logical choice.

He was campaigning against me as 'the insider', and labeled me as a 'know nothing.' One afternoon, 3 weeks before the election, I happened upon Mr. Grasso talking to a group of people on the sidewalk. I walked up behind him and heard him call me a "Dumbass Plumber who only knows his way around city hall by following the sewer pipes." I decided that while Jill and Mayor Thompson campaigned for me above-board, I would take Councilman Grasso down a peg or two.

Mrs. Grasso was an easy target. She was coming out of her hair salon, when I zapped her with the remote. "What do you want me to do?" she said with that faraway look in her eyes.

"Get in the backseat of the car." I told her. She obeyed of course.

I had rented a non-descript car for this mission. I told Mrs. Grasso to lie down on the seat and take a short nap. She was asleep instantly. She was not unattractive. She was in her mid-40s and was carrying a few extra pounds. Her name was Charlene, and she was about 5-5, with her hair dyed dark and an apple-shaped figure. I almost felt bad doing this to her, but her husband was a total prick, and I wasn't doing any permanent harm to her. Certainly not my type (especially since I had Jill), but she had a reputation as a nice person.

I drove about twenty minutes to a very disreputable part of what we call 'the big city' and parked the car in an alley next to a dumpster. There was a guy named Marvin who lived around the corner from this alley who was a drug dealer, known to exchange small amounts of narcotics for sexual favors. I knew about Marvin from a guy I did some plumbing jobs for, who knew a guy who knew Marvin. You know how it is.

I went up to the door and was greeted by a tall black man. "You Marvin?" I asked.

He said "Yeah. What ya need?"

I stepped in a little closer. "I have a lady in the car around the corner. I wonder if we can get a bag of pot if she sucks you off?"

He grinned, and said, "Sure, why don't you bring her in?"

I said, "One thing though. I'd like to get a couple of pictures of her face while she's blowing you. Nothing showing your face, of course. Its a digital camera, and I'll let you see the pictures before we leave. Sound like a deal?"

He said, "As long as she knows what she's doing, I won't even notice."

I went back to the car and woke up Charlene. I told her that we were going to get out of the car and walk into the house. When I spanked her ass, she was going to give Marvin a blowjob. I told her to do a very vigorous job, and get him off as soon as possible. I told her I wanted a picture of her with his dick in her hand his cum all over her face. I got the digital camera and led her into Marvin's house.

Marvin didn't even bother to get up and come to the door. He was sitting on his couch, with his pants around his ankles, stroking his long, thin cock, which was already semi-hard. I said, "Get to work," and spanked Charlene on the ass. She went over to him, kneeled down on the rug and took his dick in her hand. She did not hesitate in licking and sucking his knob, making him squirm on the sofa.

I got in close with the camera and got some really high-resolution shots of her with this long black dick going in and out of her mouth. Either he had no staying power, or she was very orally talented, because in about two minutes, four spurts of sticky white jism popped out of his dick and onto her face. I told her to hold very still, and look right into the camera. I got a great picture of her with a big black dick in her hand and cum on her face. She was even smiling a little.

Marvin was kind enough to hand her a towel so she could wipe the goo off her face, and gave her a small bag of weed before we left. When we got back to the car, I told her to put the bag in the bottom of her purse and forget it. As I drove her back to the salon, I told her that she would not remember anything, only that she had lost track of time gabbing at the salon. I dropped her off on the sidewalk outside the salon, and pushed OFF. As I drove away, I saw her hurry to her car as if she were late for something.

When I got home, I printed the three best photos - two of Charlene sucking that long black dick, and the money shot of her with jism all over her face. I also printed a note addressed to Councilman Grasso that read:

Dear Councilman,

A man whose wife will have sex with a stranger in exchange for drugs should probably not be mayor. If these pictures are not enough proof, check her purse.

Signed, A Concerned Citizen

I packaged up the photos and the note, being careful not to leave any fingerprints or other clues, and addressed them to Councilman Grasso's home address. I took the package to the drugstore a few miles away and dropped it in the big blue mailbox.

I arrived home a few minutes before Jill's big black 4X4 rumbled into the driveway. She came in the house and kissed me enthusiastically. She was carrying a bag from Victoria's Secret but would not show me what was inside. She had a wicked gleam in her eye and said she had a surprise for me.

I followed her upstairs to the master bathroom, and watched her strip out of her business suit as she told me not only about her day at work, but her discussions with Mayor Thompson about the campaign. She told me to strip and join her in the shower.

She kept telling me about her workday as she soaped up my body from neck to knees and washed me thoroughly. Her soft hands felt incredible on my body in the slick soap. Then I returned the favor, glorying in her soft, firm flesh and rubbing her skin clean. I paid special attention to her perfect breasts of course, and she bent over at the waist for me so that I could clean her beautiful ass.

We got out of the shower and dried off. She kicked me out of the bathroom so she could 'get ready'. I went out and lay down naked on the bed to await her arrival.

She opened the bathroom door wearing a bathrobe, which revealed very little. She posed for me in the doorway with the light behind her she looked like a goddess, and then she slowly sauntered over to the side of the bed.

Jill looked me in the eye with that wicked gleam again and dropped the bathrobe to the floor. She was wearing a yellow lacey demi-bra, which displayed her 36C tits as if they were resting on a shelf. The yellow fabric contrasted with her tanned skin in the low light of the bedroom, and I could see the dark outline of her nipples through the lace. She was also wearing matching yellow lace bikini panties which rode low on her hips and displayed her shaven pussy proudly.

She stood posing for me with one hand on her hip for a moment, then, without a word, she knelt next to the bed and took my semi-hard cock into her mouth. She sucked on it until it was fully hard, and then began teasing me by licking up and down the length of my shaft. She began talking to me between licks, "I want something from you tonight." I tried to respond but I couldn't make a word.

"I want you in my ass tonight." She took all of my cock in her throat with one smooth motion. When she came up for air she looked me in the eye and said, "No one has ever fucked my ass before. Can you do that for me? Will you fuck my ass? Please!?" She looked hopeful; as if there was a chance I would say no.

All I could do was nod and gurgle as she stroked my cock. She smiled and said, "Good." and sucked on me some more. She was really skilled at making my dick feel incredible without making me cum. I think if she put her mind to it, she could blow me all night and never let me climax. She was that good.

After a few more minutes, I motioned for her to stop, and switched places with her. Now she was lying on the bed on her back, and it was my turn to tease her. I got a small dildo and some lube out of the drawer in the nightstand and laid them on the bed. She watched me with great interest. I could tell she was both nervous and excited by our new adventure.

I started slowly, encouraging her to relax, and gently exploring her perfect body with my hands. I rubbed her nipples to attention through the yellow fabric of her bra, and I could feel the moisture and warmth from her shaved pussy through her lace panties. I slowly pulled the yellow bikini underwear down her legs, and set them on the bed next to us.

I decided to return her oral favors - I slowly licked her pussy lips and her clit, but only to relax her and make her body feel good, not to bring her to climax. She moaned and squirmed on the bed, her body begging for more, but I did not relent. I licked the vibrator to get it wet and slowly inserted it into her pussy without turning it on, and worked it slowly in and out of her as I licked her clit gently. Her body jumped every time my tongue touched her sensitive area.

She was very relaxed after a few minutes of this treatment. I spoke to her softly, asking her to roll over on her stomach. When she did, I rubbed and massaged her perfect ass, and planted wet kisses up and down her legs and lower back. Gently and gradually I encouraged her legs apart and rubbed her pussy and clit from behind her. Her smooth bare skin was slick with my saliva and her juices. I rubbed some or the slick juices up to her pink asshole.

She tensed when my finger pressed against the tender flesh. I spoke to her soothingly, saying to relax and promising not to do anything without warning her first. She sighed and I felt her will herself to relax. I kissed her luscious butt cheeks some more before rubbing more of her slickness up to her pucker.

This time, she did not tense or jump as I gently rubbed my finger around her tight little asshole. I gently spread her cheeks apart with my hands and licked her tangy flavor from her ass, and she giggled nervously, but did not tense.

She said aloud, "Oh my God, you just licked my butt hole," and erupted into a fit of laughing. I joined her in laughter, and that seemed to take away all of her nervousness. She kissed me on the mouth, I think just to show me she wasn't grossed out by my oral attentions, then she composed herself and got back into a comfortable position - knees apart, ass up, head down, resting on her elbows.

This time I used some of the lube on my finger and rubbed it on her asshole. I said softly, "I am going to put it inside you, very slowly. Tell me if it gets uncomfortable, and I will stop." I gradually increased the pressure until my index finger started to slide in. She gasped at first, but did not say anything, so I continued until I was in up to the first knuckle in her tight little asshole.

Once there, I stopped for a moment and asked if she was all right. She said, "Yes. Fine." I didn't press any further in just yet. Instead, I gently wriggled my finger, working it in slow circles to help loosen her sphincter muscles and prepare her for my fat cock. At the same time, I used my other index finger to trace the same gentle circles around her clit. She moaned with pleasure, and I slid my finger further into her ass.

When it was all the way inside her, I continued to wriggle it and applied more lube. She gasped when the cool wet lubricant dripped onto her hot pucker, then moaned again as I slowly worked my finger out and back into her ass.

She asked me to stop a moment, while she lowered her ass a little to get her knees farther apart. I took advantage of this break to apply some lube to the small vibrator. It was a little thicker than my finger, but only about have the width of my cock. When she was again comfortable, I gently pressed the tapered point of the dildo against her waiting asshole. There was much less resistance as the smooth surface of the vibrator worked past her sphincter and into her depths.

I spoke to her softly the whole time, telling her to relax, and describing how beautiful her ass was and how sexy it was to see the dildo inside her butt hole. After a few slow strokes in and out of her tight hole, I inserted it most of the way inside her, and turned on the vibration.

She gripped the bedspread and cried out as she came. Her orgasm took her completely by surprise. I continued to work the slender humming dildo in and out of her as her climax passed. "Wow, that was intense," she said, panting.

I worked one, then two fingers into her dripping pussy and gently massaged her G-spot until she had another orgasm that shook her whole body and left her sweating.

"Are you ready for my cock now?" I asked her when her second climax had passed.

"Yes," she said breathlessly. "I want you in me."

I switched off the vibrator and pulled it slowly from her asshole. Then I added a few more drops of lube to her and rubbed some on the head of my throbbing cock. I took up position behind her on my knees and rubbed my cock from her swollen clit all the way back to her ass. She shuddered.

She gasped and moaned loudly as I slowly worked my cock into her ass. She sounded like an animal grunting and encouraging my further inside her until finally my cock filled her completely, and my balls were pressed against her pussy from behind.

"I'm all the way in you, baby." I said.

"You feel so good. I'm so full of cock! Please start slow." She said.

I did. I slowly pulled my cock out until only the circumcised head was inside, then reversed direction until I was all the way in again. Jill was moaning and writhing on under me like a woman possessed.

"Again!" she gasped between clenched teeth. I repeated the motion, a little faster this time. She wailed and bucked her hips against me. When I was once again buried to the hilt in her ass, she wriggled her butt against me, begging for more.

I started a slow rhythm, long strokes in and out of her incredible tight asshole. She screamed and begged me to go faster, and I gradually increased speed, until I was pumping in and out of her ass like a porn star and she was screaming into yet another orgasm. I could not hold back any more as her ass spasmed around my cock and I shot stream after stream of hot cum into her bowels. She fell forward onto the bed and we lay together in a heap, my softening cock still inside her.

When we were able to catch our breath, she excused herself to the bathroom to clean up a little, and invited me back to once again shower with her. She soaped and scrubbed my cock, and then turned around and started rubbing her ass against me. My dick started to grow again. She giggled and said, "I don't want my pussy to feel left out."

Her cunt was still slippery and wet and I slid in easily from behind. She squirmed against me and groaned as I started fucking her. There was no starting slow this time, she wanted it hard and fast, and I was more than willing to give it to her. With each stroke, some water would splash up from between us and onto her back. The sight of my cock pistoning in and out of her really turned me on, as did her moans echoing in the bathroom.

She braced herself against the shower wall, but I grabbed her arms and pulled the behind her, using them for leverage so I could fuck her even harder and faster. This also allowed me to keep her upright in the slippery shower when she had another knee-wakening orgasm.

She bent all the way forward and put her hands flat on the shower floor. The hot water collected her dark hair around her face as I hammered her from behind. With her in this position I fucked her with total abandon until finally I felt that warm feeling in the backs of my calves tat spread all the way up to my ass and into my balls. They erupted with another load of hot jism, filling her cunt as I howled and struggled to keep from falling over.

Jill slipped off of my dick and sat down on the shower floor. She looked up at me through the streaming water like a mythical mermaid with her wet hair down almost to her hard nipples and a lustful but satisfied look in her eyes.

We finished showering and dried each other off with fresh fluffy towels. We climbed into bed still naked and she kissed me lightly and said, "Thank you" before snuggling her firm body against me and drifting off to sleep.

notnaive
notnaive
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