A Workplace Love Story

Every day John went to the gym, he couldn’t help but notice Leslie. They were coworkers, but she worked on a different floor. She was drop dead gorgeous. About 5 foot 10, with shoulder length brown hair and blue eyes. She was tall and slender, with a figure most women would kill for. John always appreciated how beautiful she was, but he could never work up the courage to ask her out. Today, he decided he would finally at least approach her at the gym and talk to her.

As John approached Leslie at the gym, his heart was pounding in his chest, despite his attempts to remain calm. Though it may seem like a casual encounter to her, he had been waiting for this moment for a long time. His eyes were locked on her lovely locks bouncing gently around her shoulders as she worked out. He couldn’t stop himself from staring at the gorgeous brown curls and how they framed her petite face. The thought of asking her out made his mouth go dry, but he pushed through his anxiety and made small talk anyway.

“Hey, you’re Leslie right? You work on the 5th floor?” John asked.

Leslie glanced up at John from her workout and smiled politely. “Yes, that’s me. And you are…?”

John took a deep breath. The moment he had been waiting for was finally upon him. He knew he couldn’t waste this opportunity, so he gathered up his courage and continued the conversation.

“Yeah, I’m John. I work on the 4th floor. I’ve been meaning to ask you something for a while…”

John was planning on asking her out, but for some reason he just couldn’t do it. “Do you know if anyone is going out for happy hour this Friday?” He asked.

Just then, Leslie’s phone began to ring. “I’m sorry, I have to take this.” She said. “Hello?” After a minute passed, John realized that Leslie was on an important call, she mouthed “sorry” to him and walked off towards the women’s locker room. John’s chance came and went. He was crestfallen as he left the gym.

As John walked away dejectedly, he couldn’t help but feel like he had blown an opportunity with Leslie and regretted not being more persistent with his advances. However there was no point in sulking about it now. Instead, he decided to shift his attention back to his workout and forget all about the encounter for a while. This would be especially difficult though, given Leslie’s captivating presence throughout his entire workout. As he left the gym, his mind was filled with thoughts of how things could’ve gone differently, had he only said the right thing at the right time.

The next day at work, John was determined to ask Leslie out. That day, he deliberately put his lunch in the 5th floor break room so he would have an excuse to go up there and talk to Leslie. Around noon, he made the trek to the 5th floor to, hopefully, have lunch with Leslie and finally ask her out. As he was sitting in the break room, he overheard a conversation between Leslie and another coworker that took his breath away.

“I can’t wait for this appointment,” Leslie said excitedly, looking down at her phone.

John turned his attention towards Leslie, trying not to seem too suspicious or eager. Though he didn’t hear much of the conversation between Leslie and her coworker, he did catch a sentence that made his heart sink.

“I’m gonna look so different afterwards,” said Leslie.

John’s jaw dropped in shock as he began to wonder exactly what Leslie was referring to. Her lovely tresses had always been his favorite feature, but could she be referring to a haircut?

“This change is gonna be drastic Leslie. Are you sure you really want to go through with that?” “Denise, you don’t know what it’s like. I always have such bad hair days, it will be so much better with it all gone.” Leslie said. “Yeah I guess, but bald?” Denise asked. “Shhh,” Leslie said. “I don’t want people here to know. Let’s go out to lunch and talk about it there.”

John watched the two ladies walk down the hallway to the door. His heart was in his throat. Was Leslie really going to shave her head? Then she would really be his perfect girl. He loved Leslie’s luscious locks, but he had always fantasized about having a bald girlfriend. So nights he even found himself wondering what it would be like to shave Leslie’s head and watch those beautiful brown locks tumble down her perfect body, and now it might all come true. He gathered up his lunch and made his way back to his desk, wondering the whole time how he would ever work up the courage to ask out Leslie if she made his fantasy come to life and actually shaved her head.

As John walked back to his desk in the 4th floor, he had mixed feelings about Leslie’s revelation. On one hand, he would miss her lovely tresses and the way they flowed in the wind. On the other hand, he found himself being drawn in by the idea of Leslie sporting a bald head. It’s certainly not common for women to be bald by choice, but John found it to be incredibly sexy on rare occasions. Now that he found himself in a situation where he could make this dream come true, he wasn’t sure whether to be excited or anxious.

That night at the gym, he saw Leslie working out. Her shoulder length hair was still there. After what he had over heard at work, he knew he just couldn’t work up the courage to talk to her. Just thinking about her shaving her head made him too excited to think clearly, let alone say something eloquent enough that would make her go out with him. It’s no wonder why, when half way through a set, John was completely dumbfounded when he turned around and Leslie was right behind him.

John was caught off guard when Leslie suddenly appeared behind him in the middle of his workout. He looked up to find Leslie with a smile on her face, but before he could say anything, she spoke up.

“I wanted to ask you a favor before I head home.” Leslie said.

John was pleasantly surprised by this and immediately perked up. He hadn’t been expecting to speak with Leslie at the gym tonight, but he was glad that she approached him first.

“Yeah, absolutely,” John replied. “What kind of a favor do you need?”

“I was wondering if you would let me apologize for yesterday. I didn’t mean to cut you off, but that call was from my supervisor about an important meeting. Do you think you could forgive me?” She asked.

John couldn’t help but smile at Leslie’s question. Her apology came as a relief to him, as he had assumed that she simply wasn’t interested after their conversation in the gym.

“Apology accepted,” John replied, still smiling. “I understand that work sometimes comes first, even at the worst times.”

Leslie nodded in understanding.

“So, what was that important call about?” John asked curiously.

“Oh just a meeting I had to lead today, nothing special. Anyways, I talked with some people on the fifth floor and I think we are all going to Sammy’s saloon for happy hour Friday. You are welcome to join! And let all the other people on the fourth floor know too! Well, see you around John!” Leslie said as she sauntered off, leaving John no time to speak at all.

John watched Leslie walk away, relieved to be invited to the upcoming happy hour, yet disappointed that he missed another chance to further the conversation with her. He made it a point to relay the information about happy hour to his coworkers on the 4th floor. After all, that would give him yet another opportunity to see Leslie and perhaps find out if she had made the choice to go bald.

The next day at work, John steered clear of the fifth floor. He didn’t want to arouse Leslie’s suspicion that he had a crush on her. Instead he ate lunch on the fourth floor and told his work buddies about happy hour. They all seemed into the idea, which was perfect for John. This would give him a real chance to hang out with Leslie after work and maybe even see if she decided to shave her head.

As the day came to a close, John eagerly headed towards the elevator, eager to attend Happy Hour and see what Leslie’s hairstyle was like. He couldn’t help but imagine her running her hands over her newly shaved head and feeling the sensation of the air caressing her scalp. But it was pointless to get ahead of himself. He had to stay focused and keep his mind on the task at hand, which was to have a friendly and enjoyable evening out with Leslie. Nothing more, nothing less.

When he arrived at the bar, he was surprised to see that Leslie still had a full head of hair. It was shorter and a different color too. She was sporting a black blunt bon with bangs. John was amazed at how sexy she looked, but he had to stop staring so he didn’t seem like a creep. As he walked over to the bar, he noticed Denise pull Leslie to the side nearby. He slid closer so he could overhear their conversation. “So Leslie, did you do it? Did you shave your head?” Denise asked.

John’s eyes grew to the size of saucers as he watched Leslie look this way and that and slowly reach up and wrap her fingers around the edges of her hair. She was wearing a wig! She lifted the wig off of her head so imperceptibly that most people would even be the wiser, but John knew.

“Yeah girl, I just had to do it. I’ve been meaning to get rid of this hair for so long. Denise, you wouldn’t even believe how amazing it felt. The barber ran the clippers right down the middle of my head and my hair just poured onto the ground, it was fantastic and liberating. Then when he was done he lathered my scalp up and shaved my head with a razor l. “

John couldn’t believe what he just heard. Leslie was bald under that wig! All those fantasies he had been having were real, at last. He could already picture the feel of her scalp under his fingers as he ran them over her newly shorn hair.

“Oh, you’re kidding!” Denise said in disbelief as she looked at the wig in Leslie’s hands. “I can’t believe you did it. You look so different. Do you like it?”

“Yes it’s so smooth. I just love running my hands over my bald head. Plus I won’t have to worry about doing my hair for a while, I can just wear this wig!” “Wow,” Denise responded, “I’m so glad you love it!” “Yeah and my head isn’t the only thing he shaved.” Leslie added. She again looked this way and that, and then put her hand to her forehead and lifted up her bangs. John watched as Denise’s eyes grew huge and she put a hand to her mouth. “Oh my god Leslie, you eyebrows!” Leslie laughed, “yeah I know! When he was done shaving my head with the straight razor and I was looking in the mirror, the barber told me I was only two quick swipes away from being hairless. I asked him what he meant and he said you still have eyebrows, I could always get rid of those. I just decided, why not? I already had my head shave, why not get rid of my brows? So I told him to do it! Two quick swipes and now I’m bald and browless!” Leslie said excitedly.

“Bald and browless?” Denise said, still stunned by what she heard. “Do you think you went a little overboard?”

Leslie’s expression turned to one of annoyance. She had just recently cut off her long hair and shaved her head bald, and now her friend was criticizing her for removing her eyebrows? She hated how people were always telling her how she should look and what she should or shouldn’t do. Her appearance was her choice and no one else’s. “Why does it matter to you?” Leslie asked with a frustrated tone.

“I think I look beautiful Denise.” Leslie said and she headed towards the bar. No not towards the bar, towards John! He gulped, what was he supposed to say to her now that he knew her secret? He couldn’t let her know that he knew she was bald and browless. What would he say? It was too late for him to think of something clever when Leslie got to him.

“John! Hi!” Leslie said as she went in for a hug. “So glad you could make it!”

“Oh my god Leslie! Fancy seeing you here!” John said, happy that he heard Leslie chuckle. Then John proceeded to say the only thing he could think of, “I love the new look by the way! Your hair looks great!”

Leslie beamed at his compliment. Reaching up and touching the blunt banged bob. “Yeah I just got it cut today, do you really like it?” Leslie asked.

John was a bit baffled by his own response given the conversation he had just overheard between Leslie and Denise, but there was no going back now.

“Yeah, it looks amazing,” John said, trying to sound as authentic as possible. “The shorter style looks really good on you.”

Leslie smiled genuinely at John’s compliment.

“Thanks, it’s such a relief to not worry about my hair so much now,” Leslie said. “What about you? How’s work?”

“Oh work is great, but you know who wants to talk about work when we just got off? How about I buy you a drink?” He said.

“Yeah, I’m with you there,” Leslie replied, glad that John had shifted the direction of the conversation away from work.

“A drink sounds great right about now,” she said, looking over the menu for a moment before settling on a cocktail.

“Shall we sit at the bar?” Leslie asked, gesturing to the bar stool next to her. “It’ll be easier to chat from there.”

“Most definitely!” John replied, happy to get some alone time with Leslie. “So, any big plans for the weekend?” He asked her.

Leslie shrugged her shoulders as she took a sip from her cocktail.

“Not too much going on for me this weekend,” she replied. “I was thinking of treating myself to a nice manicure and maybe even a pedicure. Other than that, not much.”

She tilted her head towards John as she took a seat at the bar.

“And what about you?” she asked. “Any exciting plans for the weekend?”

“Nope, nothing on my calendar yet,” John said. At that moment, John was struck with a thought. Now was the perfect time to ask Leslie out, and he knew just what to say. It was like this whole thing was meant to be.

“Hey, you know I just thought of something.

“Yeah?” Leslie asked, sensing that John had thought of something but was hesitant to share it.

“Well, what is it, John?” she asked after a few moments of silence. She had never met someone quite like him before, so she was naturally curious about what he had on his mind.

“Since we are both free this weekend , would you like to grab dinner tomorrow night? We can go to that new restaurant, Dinnerplace, my treat!”

Leslie had to stop herself from smiling as she listened to John’s request. It was as if the universe knew what she was secretly hoping for.

“That sounds great,” Leslie replied. “I haven’t been to Dinnertime yet. It’s new, isn’t it?”

Leslie’s excitement was a bit hard to hide, though she made every effort to maintain her composure.

“Well, I’m definitely available,” she said nonchalantly.

“I’d be thrilled to spend some time with you,” Leslie added, trying to sound as casual as possible.

“Great,” said John. “It’s a date!” “Yes it is,” Leslie laughed. “Now that you’ve asked me out, there’s no need to make tomorrow night our first date,” said Leslie.

Leslie’s reply made John pause for a moment before he chuckled nervously.

“So, what does that mean?” he asked, glancing at Leslie in an amused yet puzzled expression.

Leslie laughed at his confusion.

“I mean, since we never had our first date, let’s not wait another minute,” she replied. “And if you’re free after this, we can go get some dinner or something.”

John couldn’t resist smiling at Leslie’s boldness. “I’m totally for dinner,” he told her. “I’d love to spend more time with you.”

“Great!” Leslie said, “let’s leave the coworkers here! I know a great restaurant around the corner.” John was still stunned as Leslie wrapped her arm through his and walked with him out of the bar, leaving their coworkers behind.

John and Leslie walked in silence for a moment as they made their way out of the bar and through the city streets. Leslie was deep in thought, pondering how the night would unfold.

They soon reached the small, hole-in-the-wall restaurant Leslie was talking about. It didn’t look like much from the outside, but there was a cozy vibe about it that made it look inviting. Leslie led the way inside and seated herself at a table near the window. John took a seat across from her, not sure where to start but eager to engage in some conversation.

He immediately started talking to her about all the little details that were so important to get to know someone. Asking her about where she went to college, what her family was like, and even what her favorite movie was. As they chatted, Leslie realized that John was unlike any man she had ever met. He was actually interested in her. She really liked that.

They are some great burgers, and had a few drinks more at the restaurant. They even went out for ice cream after. Both of them thought the date was going amazingly, but neither would tell the other of course!

After getting ice cream they stopped at a wine bar and shared a bottle. By this time, the night was getting late and they were both a little drunk. “So John, it’s a little late,” Leslie said. “Would you mind if we turned in for the night? My apartment is right around the corner, and you are welcome to walk me up to it if you want.” Leslie said suggestively.

“Sure,” John replied, feeling a bit light-headed from the wine but also excited at the possibility of making out with Leslie. He took a deep breath and followed Leslie down the street towards her apartment, knowing that he had to play his cards right and make a good impression if he wanted this night to go well.

They eventually arrived at her apartment building. Leslie turned towards him with a mischievous smile and a little unsteady on her feet.

“What do you say we continue our night in a more private setting?” she said, swaying ever so slightly.

“That sounds great to me!” John said. Leslie wrapped her arms around his neck and began making out with him. “Oh John this whole night was just perfect.” She said leading him into her bedroom. She playfully pushed him on the bed. As he lay there on his back, she go on top of him, straddling him seductively.

“You know John, I knew you were interested in me what before today. I’ve seen the way you watched me across the gym.”

John blushed. “Yeah, you’re just so beautiful, I couldn’t help but notice you.”

“Yeah, I also noticed you listening to me and Denise today. I think you know about my little secret.” John’s face flushed red, but Leslie kept talking. “And you know what I think, I think you like it!”

“I do,” John responded, unable to control his admiration for Leslie and her new shaved head.

Leslie kissed John’s neck and ran her fingers through his hair, a smile on her face as she enjoyed the intimate moment they were sharing. She leaned down and pressed her lips against his, kissing him deeply and passionately. She pulled away for a moment to whisper in his ear.

“I bet you want to see the rest of me,” she said in a sultry voice. John’s eyes widened as he imagined Leslie’s shaved head, her body, and the bald patches on her eyebrows.

“You’re right, I really do.” John said. “Ok mister, I’ll start with me clothes.” Leslie said as she stood up and began taking off her jeans and button down shirt she had worn that night, revealing his perfect slender body and her underwear and bra.

John was still stunned. Was this really happening? Had the girl of his dreams really shaved her head today? And was he really about to see her naked and bald?

John blinked, but it wasn’t a dream. Leslie continued undressing in front of him, taking off her bra and panties. As they slid to the floor and John could see her perfect breast, he realized she was reaching up to her head.

“Now for the last little bit.” Leslie said as she pulled the black, blunt bob and bangs wig off her head, revealing her smooth shaved head and her browless face.

John was speechless. His heart was racing as he took in Leslie’s bald head and bare body. Every man’s dream had just come true. She was perfection. He reached out a hand and touched her bald scalp, running his fingers over it and taking it all in.

Suddenly, John’s eyes widened. He looked up to Leslie’s face, her shiny bald scalp and browless face glistening in the dim light, a sly smile on her lips.

John couldn’t help but caress Leslie’s head again, the heat rising in his face, overwhelmed with desire.

“I can see you are excited.” Leslie said, glancing toward the massive erection in John’s pants. “Ok big boy, how do you like it?” Leslie asked. “Is being with a bald girl everything you fantasized about?”

“It’s even better than that,” John admitted, his eyes locked on Leslie’s bald head and smooth body. “I love your smooth skin on your face, and the feeling of your shaved scalp with my fingers…”

He took a step closer towards Leslie and leaned down toward her forehead, breathing in her scent. Then he brushed his lips across her shiny head, breathing in her sweet aroma.

“I want you,” he whispered in her ear. “Now.”

“We’ll then take what you want!” Leslie said, throwing herself on John and furiously making out with him.

John’s body shuddered as Leslie kissed him passionately. He pulled her close to him, feeling her soft, smooth skin against his body.

He took a deep breath as he felt the warmth of her head against his chest. He ran his hands down to her smooth scalp, feeling the sensations he had only imagined for so long.

He looked back at Leslie, her bare, bald head glistening with perspiration, her face flushed, her eyes closed. Everything about her seemed so genuine and authentic.

He felt her body tighten in his grip as she continued to kiss him passionately.

As they continued to kiss passionately, Leslie began to undo John’s pants. She broke away and pulled them down past his ankles and off his body. Then she did the same with his boxers, exposing his huge erection. John felt Leslie wrap her lips around his cock. He was amazed how it felt, it was the best blowjob he had ever received in his life.

John felt as if he was on top of the world, his wildest fantasies coming to life before his eyes. He couldn’t wait to explore every inch of Leslie’s bald head.

If you like this story, search my other writings under my previous username, badcaptainsmooth.