Anna Gets Rear Ended

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Anna meets a big guy for unintentional anal sex.
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Anna Gets rear Ended

Anna first shows up in a humorous story called Anna Joins a Dating Service. This story can stand on its own, however.

Anna is a beautiful buxom divorced woman who lives in Cupertino. This places her in the heart of Silicon Valley, an hour’s drive from San Francisco. Since she recently divorced her always travelling husband for ‘abandonment’, she is now in the market for a new man. The reason is simple: she is in her early 30’s , and as horny as hell. Her marriage was arranged by her parents in India, so she lacks the social skills needed to interface with most men -- she can’t dance, has never been to a drive-in, and doesn’t hang out at bars. Or if you prefer, she doesn’t understand the Friday night ‘date night’ concept. This is where presumably engaged women, along with their single girlfriends converge in hotel lounges or disco joints, ostensibly for a drink, but really to find someone to shack up with for the night. Notice, wives are not mentioned, as they should be at home caring for their kids, or maybe trying to revive their husband’s interest in fucking again.

Not being able to dance is a problem with most men. Most men would rather keep a low profile, lurking in a dark corner, but always on the alert for new ‘talent’. If a woman is truly breathtaking he will ask her to dance. This means holding her close enough to stick his tongue in her ear, and firmly grabbing both her ass cheeks. This works best if both he and his partner have had a few drinks.

Lacking these social skills, Anna is rather naive about men. This lack of intercourse has led her to consider joining a dating service. One thing can be said about dating services, that is, you don’t typically go out with prison inmates. Why? Inmates are locked up, that’s why. Their social mobility is limited. Otherwise, you are exposed to men of all types, both gentlemen (who tend to be boring) and aggressive types, commonly known as gang bangers, rapists, and privileged. It’s best to hire a body guard if your budget allows it.

She joined Miracle Match (MM), a walk-in dating service. It was like renting a car. It’s not a web site. It has a physical presence in Silicon Valley. Andy was the CEO of MM, so it was Andy’s responsibility to show her around, introduce her to the right people.

Andy went to high school with Francis, who teaches ballroom dancing. So it’s natural that Andy should funnel his applicants to Francis. People need to learn how to dance.

Larry was MM’s photographer. Larry’s job was to retouch photos so people would have some appeal to the opposite sex. Sometimes the same sex. Anna received a call from Larry, the compulsive photographer from Miracle Match. Larry has uncontrollable seizures when he sees a woman with big boobs. For a photographer, this is not good because first, it scares the shit out of the woman, and second Larry’s being spastic makes MM look bad.

Ever since he first met Anna, he’s been trying to set up a time for a photo shoot. He needed, as a minimum, a good head shot (photo) for her dating profile. Larry’s idea of a good head shot would be an upper body shot with her wearing a flimsy transparent kimono robe. It’s impossible to predict the types of men, and women this would attract. For as a certainty, you’ll get your assortment of fetishists and perverts. I doubt Anna will be getting mail from the corporate staff of Facebook. Or Google. But, in Silicon Valley, one never knows.

In Silicon Valley lots of people appear to be rich. Usually you don’t get to be rich by being honest. I remember driving through an upscale neighbor with a real estate agent. I was in the market for a new home. The homes we were looking at were beautiful Tudor homes, and French chateaus. My agent, in pointing out these homes, told me mostly drug dealers and gangsters lived there. Or maybe in the Bahamas. But you get the point.

It’s different in Silicon Valley; the average salary for an H1B worker is $98K. I was considering buying a small 3 BR home for $5 million in Los Altos. On a quarter acre plot. My agent told me to buy the house for the land, and tear down the house.

Being divorced, Anna lived in Cupertino, which is in Silicon Valley. She owns a 4,500 sq. ft. home, living alone since she divorced her husband. Her home is on the edge of a cliff, so she doesn’t entertain as much as she used to. She doesn’t want to be responsible for someone falling 300 feet into a ravine because he had too much to drink.

Andy intuitively knew he ought to call Francis. Francis is a ballroom dance instructor, usually teaching only adults. Francis was the gateway to society in Northern California. Society in NorCal is not like society on Long Island, or Westchester County. First you need to have a Twitter account. It goes without saying you need an iPhone too. If you really don’t have much of a life, you also have a Facebook account. Social media usually reduces your level of human interaction to almost zero, especially if you are planning to have sex with someone besides yourself.

In Cambridge, Massachusetts I hung out at the Harvard Boat Club. That’s where I met my ex wife. Now that I’m in Silicon Valley I work with Francis, who has a good sized studio. On Francis’ staff we also have Teresa, a lesbian; and Luke, whose primary job is to fuck women. Luke is out of place in Silicon Valley because he’s as dumb as a doorknob. But the size of his cock makes up for it.

Most of Francis’ students are couples planning to get married. Francis has a few singles, mostly men. When Anna came to the studio she was immediately popular with everyone. Especially the professional men taking lessons. Whether she would be as popular if she were a flat chested, unattractive woman is anybody’s guess.

Francis gave Anna her first lesson -- a trial lesson, usually free of charge. He introduced her to the popular dances, like Fox Trot, Waltz, Tango, and also salsa and cha-cha. Dancing tango with Anna was to die for. She attended her first studio party on a Friday. After the first dance she was nowhere to be found. Teresa was sent out to the parking lot to look for her, and discovered Anna underneath a man’s body behind a shrub. It appeared his pants were down around his knees, Anna being spread eagle beneath him. Francis did not want Anna get the reputation of being an easy lay. So Teresa disentangled the couple, who protested vigorously, and brought Anna, a bit ruffled, back into the studio.

Let me introduce you to Anna’s sensual side. By all outward appearances, she was a pleasant, intelligent woman. Inwardly, Anna would make Mother Teresa look like a whore. She would sit on her patio, overlooking the scenic valley beneath her home, rolling her nipples between her thumb and forefingers, and drinking wine. Her nipples were very sensitive so she often climaxed. Unless her phone rang, usually her mother calling from India.

Out on the patio, she sat wearing only a flimsy robe, mostly to protect herself against mosquitos. She was naked under the robe. She imagined a guy kneeling between her legs, his face buried in her bush. She was thinking about the men who were going to contact her. She’d already received two emails, both from handsome men. One guy looked like Brad Pitt and the other like Tom Cruise. It was impossible that these two Hollywood stalwarts would contact her, so she astutely assumed both men submitted photos copied off the Internet. She did not bother to respond.

When Anna was initially interviewed by Andy, she was asked about her sexual preferences -- whether she like oral, conventional Kama Sutra positions, or anal. Anna wasn’t ready for lesbian sex yet. Moreover she was horrified at the thought of someone butt fucking her. But life has a way of giving us not what we ask for, but what’s good for us. In Anna’s case she needed to be sodomized.

Her first date was with a guy named Henry. Or Hank. He was exactly the type of guy Anna wanted -- barrel chested, over 6-feet tall, with thick hairy forearms. He took her to Starbucks for a latte and suggested they go back to his place. He leered hungrily at her massive boobs while she thought about it. She could bring him to her place in Cupertino, but thought he might be intimidated by the size of her home. She agreed to go to his place. It was 9 PM.

He lived in a single bedroom apartment at the back of an alley. He could barely fit his reconditioned 1986 Ford F150 XLT truck into his parking space. This scenario was the perfect prelude to Anna’s introduction to rough house sex. Anna noted that it was about 9 AM in India and hoped her mother wouldn’t call her while she was having sex with Hank. She liked Hank a lot.

Hank spoke first. “Anna, this is where I live. Kinda basic. No frills ...” He knew his flush toilet wasn’t backed up. He had just fixed it before going out to meet Anna.

“Oh, home is where your heart is,” she said waxing poetic. “Right, Hank?”

He was getting two cold beers from the fridge. “Yeah ...” he agreed.

She sat on the sofa, which appeared to have been rejected by Goodwill. “We can stay out here, or we can go into the bedroom,” Hank suggested.

“OK,” she eagerly chirped. “It’s easier to chat lying down than sitting up. Less formal ...” she said.

Hank could not believe Anna was so agreeable. His last date fought him off, and threatened to call the police.

She moved as if she were going to remove her blouse. Three buttons had already popped open. “This blouse is a nuisance,” she said. “Do you mind if I slip it off?”

Hank’s mind was on her big behind. He didn’t care what she did with her blouse.

“Oh ... no problem”, he said.

“How long have you been with Miracle Match?” she asked. “Very long?”

“Naw ... you’re my first date. I don’t usually get involved with dating sites.”

“Where do you usually meet women?”

“At the library,” he lied. “At church ... at PTA meetings.”

“Oh, do you have children?”

“Not any more. They live with my ex. I don’t see them much ...”

He didn’t mention the restraining order against him.

He moved closer to Anna, where she was lying on her back. Her blouse was off, and her impressive boobs were almost out of her bra. Her big pink nipples were pointing at the white ceiling.

“Anna, could you please roll over? Onto your stomach?” Hank asked.

“OK, but why?”

She rolled over. Her ass was big and firm. He pushed up her skirt, past her stocking tops, to her bare behind, covered only by her underpants. He reached out and squeezed. “Ohhhhhhhhhhh ... that feels good,” she murmured. He pulled her undies off.

He continued to knead her smooth buttocks, opening and closing her ass cheeks revealing her rectal pucker. His eyes widened. He licked his lips, almost forgetting to breathe. There were wisps of dark hair along the crack to her pussy. She had no idea why he was fondling her ass. She specifically told Andy she didn’t like anal.

With one hand, Hank unbuckled his jeans, and slipped them off. She turned her head, and looked over her shoulder. She initially was shocked, but then intrigued, by the long, thick cock staring at her.

“Oh, my God,” she whispered. “What are you going to do?”

He reached under her, coating his hand with her pussy cream. Then he used it to lubricate her rectum.

Before she could say ‘anal wasn’t an option’ Hank jammed his cock up her ass. It surprisingly slid in easily.

She yelled, “Wait!! Ohhhhhhh ...” as Hank continued pumping into her.

Her cell phone was ringing now, and she feverishly grabbed it before it stopped. “Hello?”

It was her mother. It was almost 10 AM in India. “Yes ... Yes. I am busy now ... let me call you back ...”

Thus Anna was baptized into the realm of anal intercourse. She wondered if it was in the Kama Sutra. Whatever ... it was fun.


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AnonymousAnonymousover 4 years ago
Really?

Really?

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