Desperately Seeking Shemale

DSS Cover

Prologue:
The Macho Mart

Shannon Morgan waited for her pound of cheese at the deli counter at Macho Mart while her husband was off with their daughter, picking out some snacks for the week. She looked from the corner of her eye to see if the brunette with the glasses behind the counter was watching her. She had reported her to her manager the week before because of her attitude, and was surprised to see her still working here. Shannon was silently hoping for an excuse to go back to the store manager with another complaint.

Shannon pressed her hand to her pocket, hoping to feel her phone buzzing before Ron and Emily returned and she lost her chance to respond to Steve’s thus far unsent text. Steve was an old friend she knew in high school, and they had just started chatting again thanks to the two finding each other on Facebook. It was just an innocent chat, but she didn’t know if Ron would approve if he found out about it. What should he care, anyway? It wasn’t as if Ron still talked to her the way Steve did.

“We’re back!” Emily Exclaimed. Her hair was blonde like her mother’s, and she was thin thanks to playing soccer and her expensive dance classes. Shannon knew that wouldn’t last when she got older and she filled out like her mother had. She had returned ten or fifteen feet ahead Ron, who was carrying the snacks in his arms.

“Why aren’t you with your father?!” Shannon snapped, taking her attention off the girl behind the deli counter (who was now undoubtedly making some kind of rude remark to a coworker about Shannon’s parenting skills). “I thought told you to stay with him!”

“I’m right here,” Ron said in an annoyingly cool voice. Shannon supposed he thought he looked cool giving his flirting looks to the other mothers in the store. His brown hair was combed back, and his shirt was unbuttoned near the top. He had no idea how goofy he looked when he was trying to act like a hot shot. “She never left my sight. I swear.”

“I don’t suppose you got anything that’s on sale,” Shannon said, sighing. She looked at the small trove of snacks that her husband and daughter were unceremoniously dumping into the cart. “What is all that junk, anyway?”

Ron sighed in that annoying way he had. “If you knew what to get, then why did you send us off to do it?”

Shannon rolled her eyes and crossed her arms across her amble bosom. She would have to go back down the aisles and replace what Ron and Emily had picked out. The truth was, she wanted Ron and Emily gone because she was expecting a return text from Steve. He was all the way in Arizona, so he should be waking up soon to see that Shannon had sent him a good morning text.
“I’m sorry,” Ron said, not actually meaning it. “I just wish I had a list of what you actually wanted us to get.”

“I shouldn’t have to tell you!” Shannon said. “I’d hope you would surprise me and use some common sense for once in your life.”

“Here’s your cheese,” the deli guy said, butting his pimple-covered nose into her argument with her husband. “Would you like anything else?”

“A pound and a half of bologna,” Shannon said, shortly.

“It’s just a few snacks,” Ron said. “It’s not a big deal.”

“This isn’t about the snacks,” Shannon said, feeling defeated by the looks she was getting from her daughter (and also some of the ruder shoppers). “We’ll talk when we get home.”

“No we won’t,” Ron said, sighing. “We never do.”

Shannon had a retort ready, but her phone buzzed in her pocket, distracting her from her fight with Ron. She was more annoyed at Ron now, because she couldn’t let him go off again. Not after the argument they just had in front of all of those people. It would be at least an hour before she could read and respond to Steve’s text. Perfect!

“Let’s just finish up and go home,” Shannon said, taking the large package of bologna from the deli guy without thanking him or even looking him. She was so exhausted by the short exchange with her husband that she didn’t even feel like asking for the manager to talk about his interruption earlier.

Shannon led her husband and daughter back through the store (while they were probably rolling their eyes and making faces behind her back). They followed and watched silently as Shannon exchanged the snacks they picked out for the ones they should have gotten. After picking out a few more items, she rolled the cart up to the checkout counter.

On the way to checkout, Shannon and her family walked past a redhead that was slightly shorter than Shannon picking out some boxes of cereal. She was a good deal thinner than Shannon and had a brightness to her face that Shannon did not. The redhead put a box of cereal in her cart, and Shannon swore that she had given her husband a look before turning back down the aisle. Shannon couldn’t see her husband, but she was sure the redhead gave him a look before because Ron had done so first.

“Make sure your tongue’s still in your mouth,” Shannon said over her shoulder, entering the express checkout line even though she had way more than twelve items. The cashiers never said anything anyway, and Shannon didn’t care whether or not the other shoppers were annoyed by the extra wait.

Shannon was happy to be going home during the short and silent drive. There, she would have the chance to be left alone long enough to read Steve’s message and respond. Ron would be out mowing the lawn, Emily would be outside running around or watching TV, and Shannon would finally have a moments’ rest. She could picture herself now. Sitting in the air conditioned room with her feet up chatting with Steve.

Shannon ran up the stairs when they got home, leaving Ron to put away the groceries by himself. For the first time that day, she was happy.

Chapter 1:
Eli Whitney’s School of Invention

Ron Morgan sat in front of his computer on a lonely Tuesday night, exactly as he did every other night. The only signs of life in the house were the clicking of his mouse, the tapping of his keyboard, and the dull glow of his computer screen. It wasn’t always so dull around Ron’s big, empty house: When his wife and daughter were still living with him, there was always something to do. Now Ron was alone, and all he could do to pass the time was scroll through personal ads on Rickslist and beat his dick silly before passing out for a few sweet hours before he had to go back to work in the morning.

Nearly eight months prior this particular Tuesday night, Ron found himself shocked by the abrupt end of a marriage he thought was doing just fine. He knew things weren’t quite right between him and Shannon, but he hadn’t thought it was anything more than another lull they would pull themselves out of eventually. He couldn’t even count the number of times he tried to seduce his wife, only to be rejected and sent to the bathroom to “handle” himself so his erection wouldn’t plague him into the wee hours of the night. Having experienced these phases before, he figured he’d wait it out. In the past, there had always been some trivial nonsense that would set off a massive fight, and the passion would rush back in. Life would be normal again. He’d never had to wait so long before, though, and while he had been counting on that old magic, Shannon was busy reconnecting with her high school flame.

He knew he should have seen the signs, would have, had he been paying any attention. A few months later, she yanked the rug out from under him and whisked herself and their nine year old daughter, Emily, from their Connecticut home to Arizona and a new life. I hope they fucking fry on the sidewalk, he thought clicking away and trying to rid his mind of the ghost of Shannon’s bitter memory.

Ron couldn’t banish the images of his wife screaming at him from his mind’s eye. How he didn’t care. How he was lazy. How he embarrassed her. How she couldn’t have friends or family over their house. He countered with every ounce of logic he could muster through the storm erupting from his wife’s vulgar mouth. He worked forty plus hours every week and did chores on the weekend, so he relaxed at night. She found his humor embarrassing because she was uptight, and she had no friends because she alienated them all by being a huge pain in the ass. Besides, she didn’t do much of the housework and avoided spending time with him at all costs.

In the end, it was better for the both of them that she left. Ron even reflected that raising their daughter in that environment was no good for her. Whenever Ron and Shannon would go through their phases of not speaking, they’d snap at poor Emily for the smallest things. It got to the point where Emily would come home and not speak to either of them out of fear of being punished for asking the simplest of questions. Even though Ron agreed that Emily shouldn’t be raised in that environment, he silently disagreed with Shannon’s decision to take her all the way to Arizona. When it came down to it, Emily didn’t even fight that she wanted her father around. Ron hated himself for it, but he often found himself mad at Emily for not fighting a little for him. She, too, knew how nasty her mother could be.

Living alone was fun at first. Oft times when things were bad with Shannon, he would fantasize about life alone, but he never thought he’d be able to obtain such a lifestyle. Now that it was a reality, he exercised every whim he’d been denied while Shannon and Emily lived with him. He was able to watch whatever he wanted on TV, eat whatever he wanted, and not have to answer to anyone. Soon enough, he was bored with all his TV shows and movies, he had gained twenty pounds and had a whopping case of diarrhea at work after his coffee every morning, and he was more lonely than he imagined he ever could be.

It was only now, sitting in the dark, that he realized that the only person responsible for this loneliness was himself. He could have paid attention instead of constantly pawing at his phone. He could have put an arm around her shoulder when she suggested a romantic comedy instead of some Jason Statham movie. Really, he could have stopped her from leaving if he had bothered trying. He even started to accept the blame for her hateful disposition in the end. The reality was sinking in. Ron had let his wife and only child leave without a fight. Deep in his mind, he wanted this. He wanted to be rid of them. He wanted to be left alone. He wanted this life.

It took Ron too long to realize that he was wrong.

Money very quickly became an issue. Paying child support and losing the second income when his wife left took a toll on poor Ron’s wallet. It would’ve made good sense to move into a cheap apartment, but nobody wanted to buy a work-in-progress starter home. Not in this shit-house economy. Nobody that would pay enough to make it worth selling, anyway. No more pay channels. No more movies. No more fun of any kind unless it was the free kind. Soon he was moonlighting as a stockman at a local grocery store called Macho Mart for some pocket money. It was a shitty minimum wage job, but Ron was just barely squeezing by with the tiny bit of extra income. “Living is the hardest part of life” slowly became the motto that Ron would repeat silently to himself on the worst of days.

So here was Ron at thirty four years old. Getting fatter, getting poorer, getting lonelier, but most of all getting bored.

So it was Tuesday night after a brutal day at work, and Ron was creeping his favorite playground: The adult personal ads on Rickslist. Casual Encounters. Missed Connections. Misc Romance. Over and over, every night, exactly the same. Casual Encounters. Missed Connections. Misc Romance. Every time was exactly the same. There were very few postings under the F4M category, and they were few and far between (when they were real postings). Most of the female ads that popped up were obvious ploys for phone sex or escorts. When there was an ad that seemed legit, Ron would never get a response.

But that was just Ron’s luck with the fairer sex and trolling the internet for free pussy.
Whether it was out of boredom or loneliness (or even possibly desperation), Ron started checking out the T4M section. Ron wasn’t a gay man. Alright, maybe a little bi: The urge to explore sexually had been strong in high school. He’d never acted on that urge, though, and only came close to having a homosexual experience once in his life. In fact, Ron would consider himself “straightish,” but there was something about the prospect of bedding a shemale that piqued his curiosity. It started with a few quick glances at the ads on The Rickslist ads. Later, he would follow a few accounts on Twitter dedicated to shemale and transsexual photos. A little later after, Ron was on various free porn sites looking up shemale porn. Without realizing it had happened, he was beating off to shemales quite often. Sometimes pretty furiously.

The T4M personal ads ranged from silly to just plain disappointing. There was a cute “chubby Latina” tranny, but she would only post close up photos of her face. When he looked into her more he discovered she wanted two hundred dollars for an “encounter”. Fuck that, Ron mused as he deleted the email. Money was way too tight to spend that much on a fat Mexican chick with a dong. Then there was “Rhonda” who actually returned Ron’s emails. Ron was eager to trade pics and set up a date, but it turned out that Rhonda was just a fat guy in a wig and dress. He didn’t even have the decency to shave his chest hair. ”Nice try, dude,” Ron said to Rhonda’s picture on his computer monitor. “But I’m not looking for a cross-dressing loser.”

Ron sighed heavily and created his own Rickslist ad in the M4T section. He skipped the title and began typing:

Early thirties guy looking to spend some time with a woman with something extra. I’m a straight man, but have been becoming more attracted to shemales and trannies. I am in the North Haven/New Haven area and have my own home. I have a full time job and sometimes moonlight to make some extra cash. I am not looking for a one-night stand or just sex. I am looking for someone I can spend some serious time with. Message me if you’re serious and we can exchange info.

Ron looked at his creation. He thought it sounded bland, but he didn’t know what else to add without giving his life story over the internet. There were dozens of others like it as well. In a rare moment of creativity, Ron thought of a clever title:
Desperately Seeking Shemale

Ron looked at the title. “This is so fucking stupid,” he said to himself. He closed the posting without submitting it. What was he thinking anyway? What chance did he actually have that there was anyone out there who would even reply to something as dumb as that?

Just before Ron clicked the newest ad titled “Cute Redhead Shemale 4 Good Guy”, his phone rang. Blocked number? he thought, looking at the phone as it buzzed away in his hand. Here we go. Fuck my life!

“Eli Whitney’s School of Invention,” Ron said in an overly pleasant tone. “Eli speaking.”
“Don’t be a dick, Ron,” the voice of his annoyed and estranged wife said. “We need to talk.” Ron had thought it was a bill collector calling. He wished it was.

“Shannon,” Ron said losing the sarcastic pleasantness and opting for a very natural indifference to his wife’s voice. “What can I do for you tonight, honey?”

Shannon sighed annoyingly into the phone. Ron wished she was close enough to punch. “You need to send Emily ninety dollars for ballet,” she said.

Now it was Ron’s turn to sigh. His head was already starting to throb. It was late, he had to work both jobs again tomorrow, and Shannon didn’t give a fuck. “What the hell do you do with the child support checks I send you?” he asked while rubbing the bridge of his nose. He started wishing he could afford a cold bottle of vodka, even just a nip or two would work at this point.

“Food and clothes,” Shannon said quickly. “You never give us money for ballet.” Ron heard someone else say something in the background. He couldn’t quite make out what it was, but it sounded rude as hell. “It’s not fair to have Steve pay for all her ballet and school and camp and soccer stuff.”

“Oh Steve wants to talk?” Ron said raising his voice. “Put him on! He takes you and Emily away from me, but I still have to pay for her ballet stuff when I can’t even see her dance? Hell, you won’t even send me a damn video! I’ve barely even been able to talk to her lately too!” Ron’s head was really throbbing now. Chubby Latina whores and fat crossdressers were now long forgotten.

“For God sake, Ron! She’s mad at you! She’s always mad at you! You never visit. You haven’t had her to your place in months. You-”

“You took her three quarters of the way across the country,” Ron interrupted. “I can’t afford plane tickets while paying all of our bills. That’s about all you left me with! What the fuck have you been telling her?!” Now Ron’s chair was on the floor and he was on his feet.

“I’ll be telling her that her daddy’s still being a dick!” Shannon sneered.

“I wish you had a dick, you fat bitch!” Ron yelled, sure that the neighbors would hear him (not that they weren’t used to it).

“Fuck you!” Shannon screamed before she angrily hung up.

“Only if you had a dick, babe,” Ron said. He started laughing feebly as he threw the phone across the room where it landed on the couch. He half expected it to ring again with Shannon calling to either apologize or scream at him some more (the latter most likely), but it sat in the silent dark. When the light on the phone’s face died, Ron decided it was time to let it go.

Ron looked at his microwave clock. It was blinking twelve o’clock. “Fuck you too,” Ron said to the blinking clock. He hadn’t reset it after the electric company shut his power off, demanding that he pay a chunk of the overdue balance last week. He checked his cellphone (which had its bill miraculously paid on time). It was 10:45. A late night for someone whose boss graciously allowed him to work a six to two shift so he can catch his three to nine-thirty shift at the Macho Mart. “Fuck this,” Ron said to nobody.

He glanced at his computer screen one more time. “Sorry, Cute Redhead Shemale”, Ron said. “I’m sure you’ll be there next time. There aren’t many nice guys in the world.” Ron clicked his monitor off and headed to bed.

Chapter 2:
Free Sausage

Ron stretched and yawned at his desk. He liked to play a little game where he wouldn’t look at the clock and see how much of the day had passed doing paperwork and responding to customer’s emails and calls. Today, he felt as if it had to be close to lunchtime when he finally looked up from a particularly tricky work order.

It was nine-thirty.

“Shit,” Ron muttered under his breath.

Three and a half hours into his shift had felt like six hours. Maybe it was the way he slept the night before, tossing and turning for what seemed like hours after fighting with Shannon. Most of his thoughts were about his daughter and how Shannon had told him that she’d been telling their daughter that he’s a dick (he didn’t doubt for a second that she would). His mind went back and forth, deciding to be mad at Shannon or Emily. He still felt guilty about being angry at his own daughter for what happened, but she abandoned him as well. When it was all said and done, he was sure that Emily was only responding to whatever lies she was being fed by her evil mother.

Ron dropped his pencil onto his desk and put his face between his hands. He felt the scruff of his cheeks and realized that he’d forgotten to shave again. If his boss noticed, he’d be sure to have another hygiene talk with Ron. To make matters worse, his supervisor at Macho Mart would definitely notice and make some kind of comment about not appearing “tidy” to the customers, and he didn’t have the time to run home and properly groom himself. The dickhead usually made him load and unload boxes in the stockroom anyway. With luck, Ron would be able to divert his attention away from last night’s problems and to unloading the various meats and merchandise off a truck.

Unloading trucks was such sweet, unthinking bliss.

“What are you dreaming about?” a voice behind Ron said.

Ron nearly jumped and fell out of his chair. If his boss caught him nodding off it would mean the end of his six to two flex schedule. It would also mean saying bye-bye to his moonlighting job at Macho Mart. When he turned around, he was relieved to see it was only Vinny, his coworker from the cubicle across the aisle.

“Morning, Vin,” Ron said. Vin was wearing a New Haven Classic golf shirt (which wasn’t part of the dress code, but nobody seemed to bother him about it). His graying hair was slicked back, and his face was shaved clean. “I’m just trying to shake the cobwebs.”

“You look like shit,” Vin said. “You need to get out more. Go on some dates or something. Have you been looking since Shannon left?” Ron was regretting sharing his problems with Vin, but he didn’t have anyone else to talk to when Shannon first left. Vinny was a couple of decades older than Ron, so he would give him some sage-like advice whenever he felt that Ron needed some. Chances were usually good that Ron didn’t feel that he needed it, though.

Ron almost answered after the images of shemales popped into his head. Yes, he had been looking for a date, among other things, but he wasn’t about to share any of that with Vinny.

“Not really,” Ron lied. “I barely have time to take a shit, let alone take a woman out on a date.” This statement depressed him as well. He didn’t know where he’d find the time to take anyone out if he was working at Macho Mart at nights and sleeping on the few nights that he didn’t work at the store. The fantasy of dating a shemale had just gone out the window.

“Well, you can’t mope around forever,” Vin said. “You only get one life. Shit or get off the pot, right?”
Vinny left before Ron could respond in any way. He didn’t get up, but he’d put money on a short skirt having lured Vinny away. Now that Ron’s bubble about dating a shemale had been burst, his mind was calculating how on earth he’d be able to pull it all off. He had an urge to punch up Rickslist into his web browser, but then he remembered that his company monitored all of its employee’s web usage.

Ron sighed and went back to work. He once again and fought the impulse to look at the clock. He lost.

Nine forty three.

Ron decided to get another cup of coffee and go try to blast the toilet off the wall. Metaphorically, of course.

***

Cindy left her house shortly after arriving home from work that evening. She promised her best friend, Katie, that she would make a pot of jambalaya to bring over when she visited this weekend. Looking through her ads on the counter, she noticed that Macho Mart had the sausage she needed on sale, buy-one-get-one free. “BOGO!” she exclaimed to her empty kitchen. She grabbed her keys and ran out of the door.

Cindy ran through the rain back to her car. She sat in the driver’s seat, realizing she left her jacket inside and now her NY Jets shirt was all wet. It was OK, since it was her black one. Rather than ironically run through the rain again to get her coat, she put her key in the ignition and drove off.

***

Ron had finished saving the world one report at a time by two o’clock, and now he was busy cleaning it up one aisle at a time. He was trying to focus on the tedious task at hand to avoid dwelling on the “conversation” with his wife last night. Continuing the fight to dodge against the slow passage of time, he studiously avoided eye contact with any clock in his presence. On days like today, time slows to cold molasses the more you watch it tick by. The best thing to do was to let the shitty grocery store music hypnotize him as he restocked the store’s rapidly dwindling stock of BOGO sausages. Since they put it on sale, he couldn’t keep it on the shelves. The people of North Haven loved their sausage.

While punching a box he’d just emptied to flatten it, he looked up to see a mother and son walking towards him. The boy appeared to be around the same age as his daughter, and he was instantly thrown back into his earlier ruminations about the daughter too far away to see (even if she had wanted to see him). The boy had on a pajama set that made him look like a giraffe from head to toe. He was even wearing the hood of the outfit, making the transformation to Teenage Mutant Ninja Turtle reject complete. Suddenly, Ron realized he’d started at the kid too long, and his mother was leveling a dirty look at the creepy old man. They passed him without a backwards glance, taking two packages of sausage with them.

“Don’t be pissed at me,” Ron muttered under his breath as he opened a fresh box of sausages. “I’m not the one who dressed your damn kid like Silence of the Giraffes in public.” Behind him, a woman’s barely stifled giggles surprised him enough to pucker his asshole. To his delighted relief, the redhead behind him was trying to smother a brilliant smile as she faced Ron. Ron smiled back, wishing he had something to say.

“Is that the sausage that’s on sale this week?” she asked, somehow suppressing her mirth.

“Oh yeah”, Ron replied, holding a box in his hand. “I’m the guy with the sausage.” Ron’s asshole puckered once more at the conclusion of his comment. A complaint about an innocent innuendo would easily lose him the minimum wage income he so desperately needed to keep his shitty life going. He silently prayed for her to smile as the seconds began to feel like minutes. Finally, God bless him, making her smile once more.

Thank God, he thought. That comment could have gotten him fired as easily as it earned him a smile. The woman couldn’t have been older than twenty-eight or twenty-nine, with shoulder-length dark red hair and nails to match. She wore a black Jets t-shirt, and from the way the material clung to her gorgeous breasts, she’d obviously gotten rained on. Chilled by the grocery store’s air conditioning and sausage coolers, he watched as goose bumps stole up her arms, and, like magic, her nipples harden into perfect little heads under her shirt. Her breasts looked like a perfect handful. There was a stirring in Ron’s pants he usually saved for his various Internet adventures. He gulped and tried to ignore the stirring.

“Well now,” she said, blushing a bit, possibly noticing Ron looking where a gentleman should not. “You think I can take some of those sausages off your hands, or are you just going to stand there holding them all night?”

“You sure can,” Ron said smiling like a goon. He handed the woman over the package of sausage he was about to shelve. “Here you go. I like a lady with a bit of sausage.” Ron wished his over-tired brain processed that last sentence before he just blurted it out. Whether he was overworked or stressed or any number of things, Ron had just stepped in it big time if she didn’t smile at that one. Less than a second must have passed, but it felt like forever. Please smile again, he thought desperately.

She did smile (finally). “Wow,” she said with a goon-like smile of her own that Ron thought lit up her face. “I usually don’t get this kind of service here from someone handling my meat.”

“I’m only a part time meat handler when I’m not office jockeying. I’m Ron by the way.”

“Cindy,” she said, smiling widely. “It’s really nice to meet you, Ron.”

“Likewise,” Ron said. “If you ever anything else, I’ll be glad to help. I know plenty about produce too.”

“No produce tonight, Ron,” said Cindy. “I’m just a lady after a bit of sausage tonight. It was really nice meeting you. Maybe next time I’ll catch you in produce and we can talk about cucumbers.” Cindy gave Ron one last perverted smile.

—————-
Read more: Desperately Seeking Shemale on Amazon.com for Kindle or Kindle app!

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2 thoughts on “Desperately Seeking Shemale

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