Friday was winding down, and Tim watched the second hand on the clock, positioned opposite his desk, creep across the dial toward the magic number twelve. 5:00 PM was upon him, and he continued to sit and watch as staff filed past in a parade celebrating the end of the work week.
A few of his closest coworkers stopped by to ask if he was heading to Tackles, a local Sports Bar and hangout that would be the site of celebration for the retirement of his supervisor and mentor, Chuck Winters. Tim assured each of his attendances, but he felt ambivalent about being there. But Chuck deserved a great send-off, and Tim would suck up his own feelings to honor him.
Tim’s relationship with Chuck began three years ago at Midwest Marketing, where he was assigned to Chuck, who headed the National Accounts department. During that time, they partnered on the company’s most successful ad campaigns and built an award-winning creative team. As Tim’s mentor, Chuck generously shared his knowledge and gave Tim the autonomy he needed to grow. With retirement looming, everyone figured Tim would be the next man up, becoming head of national accounts. That all changed three months ago.
Per company policy, Chuck submitted his official retirement statement, and Tim was scheduled to meet with President Mark Westman, the majority owner, the following morning. Tim was looking forward to it. So was his live-in girlfriend for the past year.
Tim knew Tabitha from high school, but their social circles could not have been more opposite.
Tim was never considered a nerd. On the contrary, he was handsome, in good physical shape, and fit in with everyone. But he concentrated on academics and had little time for athletics. However, he was always in the stands for home football and basketball games, where he admired Tabitha, a cheerleader, from afar.
Being a cheerleader, Tabitha ran with the jocks and a clique of other model-type young women with blond hair and big tits whose aspirations were to be the wife of an NFL quarterback or a Playboy centerfold.
Tim and Tabitha’s paths later crossed at a sports fundraiser for their alma mater, and things took off from there. He fell under the spell of her beauty, and she was impressed by his bank account. Their sex was fun and passionate, and there was plenty of it. They made a handsome couple.
Mark Westman welcomed Tim into his office, offering him coffee and a seat. Chuck was not the only associate above Tim who provided direction; Mark was one of Tim’s biggest fans and encouraged him whenever he could.
They exchanged pleasantries as they sat across from each other in Mark’s spacious office, and Mr. Westman got right to the point.
“Tim,” he led, “You and Chuck have done incredible work together and have led the marketing departments in many accomplishments. With his retirement, it would be a natural transition to put you in place as head of national accounts.”
For some reason, Tim had an uneasy feeling about where the conversation was going.
Mr. Westman’s tone became serious.
“However, we have decided to take the division in a different direction, and as difficult as this is, I have to inform you that Andrew Westman will be transitioning his role from Vice President of Accounting to the Head of Marketing’s National Accounts. He is to begin working with Chuck Winters on stepping into his new role immediately.”
Tim’s mind spun in confusion.
What is happening? Andrew Westman, really? This can’t be real. I have worked so hard!. The thoughts raced through his brain.
“Andrew Westman, your nephew?” Tim asked, dumbfounded.
“Like it or not, Tim,” Westman retorted. “Andrew’s future is with this company, and it is an integral part of his professional development that he be exposed to all facets of its success.”
“Look,” Westman said with feigned compassion.” Why don’t you take the day off? I know it’s a big blow, but you are still an integral part of our team. I also expect you to be ready to go tomorrow and be supportive of this decision.”
Tabitha did not expect Tim to be home when she arrived at their apartment that afternoon. Tim told her the news, and instead of support, he received disappointment.
The relationship lasted another two weeks before Tabitha left him, stating, “I wasn’t in this relationship to be the girlfriend of the flunky to the owner’s nephew.”
BITCH! Tim thought as she walked.
Tim made it to Tackles. He knew he owed it to Chuck to be there. He walked straight to the bar and ordered a double Blanton’s on the rocks with the big cube. He downed it in thirty seconds before ordering a second.
Chuck, who was also unhappy with the decision, dropped by to chat and offer one last bit of support.
“I am always here for you, Tim,” he said. “We will get together when the dust settles.”
Tim couldn’t say much. His gaze swept over the happy faces of the crowd gathered to honor Chuck’s legacy. All he could do was nod as Chuck excused himself to get ready for his farewell speech.
He looked across the bar again and caught the eye of a woman in an electric-blue cocktail dress that stood out like a beacon in a sea of khaki and navy. Their eyes met, and she gave him a slight consoling grin. He had seen her around, but they had never been professionally involved. He turned to the bar for a third Blanton’s.
Turning back to the crowd, Tim noticed the woman in the blue dress walking towards him, her eyes locked on him.
He felt entranced by her erotic beauty. Her skin was the color of deep cocoa, and her cheekbones radiated a soft sun-kissed glow. Her lips were full, and her red lipstick accentuated their lusciousness.
She was thick, but not fat, and about the same height as Tim. Her strapless dress revealed her broad shoulders and the cleavage of her two round, firm breasts. The dress’s tightness held back her soft tummy and hugged her hips. The hemline stretched across her thick upper thighs.
She walked up to Tim and extended her hand. Her skin was soft, and her red nails were well-manicured
“Tim,” she said. “I am Rayshawn. I am in IT.”
“I know we have never worked together, but the whole company knows who you are,” She continued. “I wanted to say that I am sorry you did not get Chuck Winter’s position. I can tell it is weighing hard on you.”
Her diction carried a slight Caribbean accent, and Tim sensed she had once lived in the islands.
“What are you drinking?” she asked.
“Blanton’s,” Tim responded.
Rayshawn turned to the bartender. “I’ll have a Blanton’s Old Fashion. Rocks, please,” she ordered.
Turning back to Tim with her drink, she said, “It’s not good for you to drink alone. Especially when you are alone in a crowd.”
She raised her glass to him, and he reciprocated by bringing the rim of his to hers in a small toast before taking another sip.
“Thank you, Rayshawn. That is very nice of you,” he said to her. “I am just here to honor Chuck,” he added as he took another drink.
Chuck was about to say a few words, and they turned their attentions to his monologue.
Standing next to Rayshawn, Tim felt something was alluring about her. Perhaps it was her Caribbean mystic, or her brick-house body squeezed into her dress. Or maybe it was just the alcohol taking effect.
Chuck finished his speech with a round of applause and a crowd of handshakes.
Tim downed the last drop of his bourbon and turned to Rayshawn.
“It was a pleasure meeting you. Thanks for sharing a drink with me. See you around the offices,” he said with an outstretched hand.
“Where are you going?” she asked. “You are in no condition to drive. Let me take you home. You can Uber for your car in the morning.”
“Home?” he guffawed. “There’s nothing for me at home.”
“Then we will go to my place. I can feed you. You need something better than bar food.”
Tim may have been on the brink of inebriation, but he still had the sense to know that Rayshawn was right.
“Ok. We will make it your place,” he acquiesced.
“Here we are, Tim,” Rayshawn said as she opened the door to her studio apartment, which was more spacious than Tim had anticipated, given the building.
A kitchen and dining area ran the length of the apartment along the right wall, and the living area, with a couch, chair, and entertainment center, was in the middle, providing plenty of space for single living. Her bed was in the opposite corner of the kitchen, obscured by a folding room divider. Tim assumed the bump-out, with its two doors, provided room for a bathroom and a closet.
Tim felt woozy from the three bourbons he’d had, which had raised his temperature. Beads of sweat were apparent on his forehead as he took in the surroundings.
“You are hot,” Rayshawn noticed. “Let me take your jacket,” she continued, grabbing the collar and helping him remove it.
“Excuse me for a minute,” she said as she took the jacket to the closet and slipped out of sight behind the room divider.
A dim light projected her shadow against the thin fabric of the divider, and Tim watched as the shadowy image removed her dress and replaced it with a robe from the bed. For a moment, her silhouette revealed the perkiness of her breasts, the thickness of her midriff, and her wide hips.
Rayshawn returned to the living space in a silky, flowered robe that did nothing to conceal the outline of her nipples.
“You need to be more relaxed,” she said, “Standup and let me get that tie.”
Rayshawn looked Tim in the eyes as she untied his necktie and removed it from his collar.
“You have had a hard day,” she said as she gave him a pec on the cheek.
“You should let me take care of you,” she continues as she unbuttons the second button of his shirt and lightly kisses his lips.
Tim’s head was spinning from the liquor he consumed and the unexpected advances from this exotic woman from the islands with deep brown skin.
He accepted her kiss, and she promptly gave him a second, then a third. Her lips parted, and her tongue gently parted his. Their kisses became deeper, and Tim found himself becoming more aggressive in wrestling her tongue with his. His breathing became heavier as his arousal increased, and he felt his cock grow erect as he gave in to her advances.
Rayshawn unbuttoned his dress shirt and quickly removed it, along with his tee, as they made out. She pressed against his bare chest and lowered her robe, exposing her firm, round breasts. They were the same smooth cocoa color as the rest of her body and topped with near-black, hard nipples the size of Hershey’s kisses.
Tim was turned on to feel her breast press against his chest, as her finger combed through his chest hair, and massaged his pecs. Her hand continued downward past his abs and to his waistline and landed on the bulge of his crotch, where his hard-on stretched the fabric of his pants. She gave it a hard squeeze that excited Tim even more.
Tim was amazed by his reaction to her body pressed firmly against his. He was used to sex with girls who were fit and athletic, but he found the thickness of her body to be an aphrodisiac, and his hand roamed to feel every curve and settled on her ample rear end, where he gave a hard squeeze. But he wanted more. He wanted to touch and finger her pussy to match her petting of his cock.
He moved his hand from her ass to the waistband of her panties and slowly moved it around the side of her hips until he felt the smooth skin of her upper pubic area. He wanted her pussy and pushed his hand down, thinking of how he was going to finger fuck her black cunt.
His hand slithered downward, ready to go deep in her slit, but something was wrong. His hand could not find her pussy. It was obstructed by something in her panties, and in his confusion, he grabbed it and realized what he was holding. A cock!
Tim jumped back, breaking their embrace, and he looked Rayshawn straight in her eyes. He tried to say something. He was tongue-tied. One moment, he was raging in arousal over the exotic, thick-assed, black beauty that he wanted to fuck, then he was dumbfounded by the realization that he was getting turned on by a man.
Rayshawn spoke, “Oh, Tim, I can still be the woman you want.” And without hesitation, she unbuckled his pants, lowered them to his ankles, fell to her knees, and engulfed his hard cock in her mouth.
Her movements were swift and took advantage of Tim’s reaction time, which was hampered by the alcohol and testosterone surging through his system. The pleasure sensors in his brain gave in to the sensations emanating from his cock being sucked by Rayshawn.
He looked down and marveled at Rayshawn’s bright red lips surrounding his shaft as she bobbed up and down on his member, her fingers with their red nails gripped the base of his cock, stroking him as she gobbled his erection. He witnessed her beautiful, firm titties bounce as she sucked, and looking further down her body, he saw her erect penis sticking straight out between her thick thighs, and he saw her free hand grab it to jack herself off as she was going down on him.
Tim relented to the pleasure he was experiencing, and he tilted his head back and said, “Oh fuck, Rayshawn! That feels awesome.”
Rayshawn slowed her pace, and after giving his cock a few kisses on the head, she stood up.
“Step out of those pants and let’s go to my bed,” she said as she turned around completely naked and led the way.
Rayshawn climbed from the foot of the bed to the top of the mattress. Tim watched as she settled against the pillows, slightly spreading her legs. Her cock stood up four and a half inches hard, but it was on the thick side. She gripped it with her right hand and started stroking. A drop of precum emanated from the head and shimmered in the dimly lit space.
Tim was now entranced. The shock of Rayshawn being transgender had worn off, and all he saw was an exotic, deep cocoa beauty pleasuring herself. The fact that it was her cock that she was rubbing added to her sensuality, and Tim felt compelled to grab his cock and masturbate as she lay before him.
He was overcome by a short spell of vertigo from the intense sexual attraction that he was now feeling, and he wanted her. He wanted to taste her, but there was no pussy for him to eat, only cock.
Tim climbed to the top of the bed and grabbed Rayshawn’s erection from her hand. It felt different from his own, and he was mesmerized by its thickness and the vein-encircled shaft. The drop of precum became heavy enough to escape gravity and ran slowly down the small crevasse on the underside of her gland. His tongue reached out to it, and Tim licked the precum from her dick.
Tim, admittedly, had tasted his own precum in curiosity, and he was not repelled by it, but Rayshawn’s was different. Its sweetness was intoxicating. At that moment, Tim took Rayshawn into his mouth and went down on her.
Rayshawn ran her fingers through Tim’s hair as he moved up and down on her black member and moaned, “That’s it, honey, suck my cock. Mmm, it feels so good!”
Tim let all inhibitions go as he sucked her dick, and he was enjoying it.
He almost burst out in laughter as he thought to himself. I would never do this to a guy.
Tim came up for air, and Rayshawn grabbed his head before he could go back down.
“I want you to fuck me, baby,” she said to him. “I want you to fuck me hard.
Tim was beside himself. No woman had ever offered him their ass to fuck. In fact, he had never performed anal before. He had fantasized about it, and he brought it with Tabitha. A stern NO was all he received.
And now, here was Rayshawn on her back in front of him with her legs raised, hips forward, and her two hands spreading the cheeks of her ass and exposing her hole to him. Her dark, baby smooth skin gathered at the starburst entrance to her anus, and Tim stared, dumbfounded.
“It’s OK, baby. It’s ready for you. Get your cock in there and fuck me!” she demanded.
Tim scooted forward, holding his cock by the base and pointing its head at her opening. He pressed against her hole and was surprised at how easily it penetrated her.
Rayshawn let out a gasp.
“That’s it, honey. Nice and easy,” Rayshawn instructed.
Tim pushed slowly as her sphincter relaxed while keeping a firm grip on his cock. He finally made it all the way in. His crotch pressed against her ass hole. The tightness and heat were incredible. He let out a breath to keep himself from exploding.
Rayshawn squirmed from having her ass filled. She moaned and was breathing heavy, and she put her hand around her short, thick cock and started stroking.
“Oh, baby, that feels so good. “Now give it to me,” she moaned.
Tim started to grind, then he began to hump, bringing his hard cock three-quarters of the way out before pushing back in. Rayshawn’s anus was relaxing, and he found it easier to move in and out.
He looked down to watch his cock penetrate her. Then he admired her body. Her dark skin, her breasts, and her tummy were all beautiful and erotic to him. He was turned on by watching her jack off. It was all crazy, but his sex drive had taken over, and he increased the speed and aggressiveness of plowing her hole.
Tim started to feel woozy, and he felt the tightening of his groin that signaled his oncoming orgasm.
“Fuck, Rayshawn. I am going to cum soon,” he grunted.
“Do it, baby. Fill my ass with your cum,” Rayshawn demanded, just before grunting and shooting a jet stream of her jizz that landed in large droplets against the dark skin of her tummy. The iridescence of her spunk glistened in the dim light.
Tim was mesmerized by Rayshawn’s ejaculations, and he felt her ass clench his cock with each spurt, causing him to explode. He pushed in deep, and Rayshawn could feel his cock throb deep inside of her with each squirt of sperm that he expelled.
He had never orgasmed so violently or for so long as he pressed his body against Rayshawn’s to kiss her. Her cum was soaking his abs as he lay on top of her. He moved back off from on top and watched his penis flop out of her wet butt hole. A stream of his sperm escaped with it and oozed down the crack of her ass.
A sudden dizziness ascended upon Tim. The stress of the day, the alcohol, and the rigors of sex sapped his body of all its energy. He was blacking out and took in Rayshawn’s nakedness before falling forward unconscious on the empty side of the bed. He was out.
Tim smelled coffee as his eyelids barely opened. He squinted from the brightness of morning. His head pounded, and his body was sore. He was still naked but wrapped in a warm, comfortable blanket, and he could hear movement from the other side of the partition that separated the bed from the rest of the room.
“Oh my god, what did I do?” he thought, recalling the events of the night before. He felt queasy, and he knew he needed something in his stomach.
Did I really fuck a she-male? He asked himself as the sex from last night became clearer in his memory. And as they became clearer, he developed an extreme case of morning wood. His mind may have been wrestling with what happened, but his cock was all for it.
He let out a moan as a sharp pain stabbed his brain like an ice pick.
Rayshawn popped her head around the partition within seconds of hearing him stir.
“I have your pants right here,” she said as she came around the bed. “And I made coffee. I thought you would need some.”
“Yes, thank you,” he muttered, noticing that she was in a pair of workout pants and a sweatshirt. Her makeup was still intact. She was as visually stunning as she was the night before.
“C’mon,” she said with a giggle. “I have a full Saturday, and I need to get you to your car.”
She handed him his coffee as he entered the living space of her apartment, and she made herself busy until it was time to leave.
Monday morning meant it was back to the grind for Tim, and he was dreading it. It would be his first day under that flunky nephew, Andrew Westman, and he hated the thought of working under him. His drive in seemed to take longer than usual as he pulled into the parking garage and his assigned space.
As he stepped out of his car, his phone beeped, alerting him to an incoming text. It was from Mark Westman.
“Come up to my office immediately when you get here. Do not talk to anyone on the way up,” it stated with an ominous tone.
On his way to Mr. Westman’s office, he passed Andrew’s new office, but Andrew was not there. It was occupied by a man in a dark suit and two technicians with “FBI” on their jackets, who were dismantling the computers and monitors on Andrew’s desk.
“What the Fuck is going on? Tim thought as he hurried by.
Standing at the door of his office, Mark Westman was anticipating Tim’s arrival.
“Get in here!” he said tersely as he closed the door behind them.
“My fucking nephew…” Mr. Westman said without explanation.
“While setting up his office this morning, IT reported finding items of an illegal sexual nature in his cloud account.” He rambled on. “They alerted the police before anyone else! The FBI took him away in handcuffs and is confiscating everything!”
“Andrew is out!” We are putting you in place as head of national accounts, Westman continued. “Chuck is staying on another thirty days to lead the transition. I am sure you would need less than that.”
“You are to meet with Chuck immediately,” he said, opening the door for Tim to exit.
Tim kept shaking his head throughout the day over the quick turn of events. He and Chuck burst out laughing at the littlest things as they prepared for Tim to take over. They agreed to have a celebratory drink at Tackles after leaving the office.
Sitting at the bar with Chuck, enjoying his favorite Blanton’s Manhattan Rocks, Tim was still in shock! What a strange weekend it turned out to be.
Then, out of the corner of his eye, he saw Rayshawn making her way to where they were sitting.
She was more conservatively dressed than on Friday night, but she was still stunning. Tim felt his cock stir as he remembered their encounter.
Rayshawn extended her hand to Tim, and he accepted with a firm handshake.
“Tim, congratulations on your promotion. It looks like things have a way of working out, she said warmly. “If there is anything you need from my offices, please let me know.”
“Thank you, Rayshawn,” he said as their eyes briefly locked, and Tim fondly recollected the evening they spent together.
Chuck watched her walk away, then turned to Tim.
“You know her?’ he asked.
“She approached me at your retirement party to give condolences. I don’t think she liked Andrew Westman,” Tim explained.
“She reminds me of a man,” Chuck said before taking a sip of his drink.
“Naw,” Tim replied. “I think she is all women.”