Fourth Date – Part 2

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“Ugh. Just 5 more minutes…. Please” Lana said sleepily to her alarm clock as she slapped the snooze button.

It was now three weeks since Lana had her fateful encounter with Sarah. In this short period of time, things had changed dramatically for her.

For starters, everyone absolutely adored her stylish new bob. She received compliments at work, from her friends, and even at the grocery store. Moreover, she noticed that she was attracting older and more established men as well both in person and on her online dating profile.

Immediately after Lana posted the photos that Sarah took on her Hinge dating profile and made it her default picture, she began to get dozens of new ‘likes’ from attractive men in their early 30s… the exact age group she was most attracted to.

One guy however, Alex, really stood out. He was her type physically: 5’10, middle-eastern, athletic, and bearded. In addition, he was also a successful lawyer, with his own thriving practice at the age of 32. But what really separated him from the other guys, was his way with words and his fixation on her hair.

Specifically, when he initially reached out, he told her that her bob looked amazing and that he could tell she had just gotten it cut in the photo she posted. This attention to detail was impressive, but also, the fact that a masculine looking man such as himself would correctly identify her style as a fresh cut bob both threw her off and intrigued her at the same time. It even caused her to slightly question his sexuality. Regardless, she agreed to date him.

The first three dates were spectacular. He was a perfect gentleman: well dressed, well spoken, and polite. Moreover, her fears about his sexuality were quickly alleviated when he passionately kissed her after their first date. It wasn’t that was a spectacularly amazing kisser – he was definitely above average – but rather it was the way he gripped her bare neck and ran his hands through the base of her bob that she found extremely exciting. The intensity to which he would caress her nape, evenly matched the vigor of his kisses, and this drove Lana mad. The slow and methodical rise in passion felt like he was taking her on a roller coaster ride, with a steady build-up the more heated they would get, ultimately reaching a climax of energy and affection and consequently letting their mutual exhilaration run wild. This never got old for Lana and turned her on immensely.

Lana also noticed that Alex would subtly, but very fluidly, continually tie certain conversations they had to her hair. He was always so interested about why it was so long previously, why she decided to cut it, and whether she had plans to cut it again. A month ago, she would have found this quite strange, but given her recent not-so-platonic experience with Sarah, she was very intrigued as to where this curiously of his came from. In fact, she was tempted to tell him about her experience with Sarah in more detail, but felt that it was too soon in the dating process to share something she herself did not even fully understand yet. Regardless, she was thrilled to be dating someone that was so unique and checked all her boxes.


“Okayyyyy. Okayyyyy. I’m uuuup.” She murmured to herself as she began to stumble out of her comfy bed.

It was a Friday, an off-day, for Lana. She had just worked two consecutive 12-hour shifts on Wednesday and Thursday, and was enjoying her planned sleep-in.

She slipped out of bed and pulled back the curtain of her downtown San Diego apartment, letting rays of sunshine in as she peered outside.

‘It’s perfect’ She thought to herself as she surveyed today’s weather. ‘A beautiful sunny morning, 75 degrees. Not too hot, not too cold.’

Today however was no ordinary day, it was the day of Lana’s fourth date with Alex. It had been ages since Lana went on a fourth date and she was giddy with excitement. She generally had a rule – if she did not feel serious potential after date 3, she would end it… and she was quite picky. But Alex was different. There was just something mysterious about him and the way touched her.

The plan was to meet at a new speakeasy called “Barbed Wire” at 6pm for drinks, and then go out after. Lana had never heard of it but given that Alex had flawlessly planned the previous 3 dates, she did not even bother looking the venue up.

Lana went about her usual Friday routine which consisted of a full day of “me time”. She went to cross-fit in the morning, treated herself to a massage at around lunchtime, and got her nails done in the early afternoon. Since tonight was extra special however, she also went for a blow dry at 4pm so that her hair looked absolutely perfect for her date with Alex.

Best Bob Hairstyles & Haircuts For 2020

She got home just in time to change and freshen up before her date. Given that it was a Friday night date, Lana decided to dress it up a bit by wearing her favorite black dress. It was simple, yet sexy and stylish. The lower part hugged her perfectly, showing off her athletic legs and toned butt, with the top part of the dress clinging perfectly to her perky breasts and exposing a bit of her midriff.


She completed her look by putting on just the right amount of makeup to accent her facial features and wore a couple of golden hoop earrings in each ear which looked perfect with her short bob. The entire ensemble looked amazing with her perfectly straight short jet black hair.

‘I can’t wait for Alex to rub his hands all over my neck and body’ She thought to herself as she took a look in the mirror before ordering her uber and heading out the door.


“Wow wow you look –“ Alex began to say upon noticing Lana in front of the venue, “amazing, I’m speechless”

Lana stepped forward and greeted Alex with a kiss, “Yeah? You like it?”

“Like it? I love it… and your hair…goodness.” He responded, as he continued kissing Lana, gently stroking her neck.

“I love the way you compliment me” Lana said in return. “Where is the speakeasy though, I don’t see anything here except for a Barbershop.”

Lana was correct, the street had a few small shops on it, with a classic looking barbershop in the middle, a Vape store on the left, and a liquor store on the right. She noticed that the barbershop was still open and there were two chairs, but only one barber – a female barber – working. She was extremely attractive, with long blonde hair, two full sleeves of tattoos, and sexy petite figure wearing a black dress and heavy makeup.


“Well, it wouldn’t be a speakeasy if it wasn’t hidden!” Alex exclaimed enthusiastically “We actually have to walk through the barbershop to get to it… get it… ‘BARBed Wire’”

It was now clear to her. There was some kind of obsession for Alex with hair, and instead of turning Lana off… it turned her on. ‘I’m going to ask him about it after we have a few drinks…’ She thought to herself before answering him,

“Wow. That’s so clever, I love it. I can’t wait to see it”

Lana and Alex walked through the barbershop and greeted the barberette, who seemed to pay a bit of extra attention to Lana. They went through the back of the shop and into a dark hallway, which led to the speakeasy bar in the back.

The speakeasy oozed with nostalgia.. A nice classy bar, checkered flooring, no windows, a few booths, and a small dance floor. Alex did it again, Lana loved the ambiance.

“This is amazing!” She told Alex. “How do you find such amazing places?… I’m going to go to the ladies’ room, could you order me an Old Fashioned?”

“Sure thing sweetheart, I’ll get us a nice spot in the booth and order some appetizers too” He Responded.

After a couple of stiff drinks Lana final worked up the courage and said “So…I notice you pay extra attention to my hair, I like it, but I’m just curious as to why?”

This caught Alex a bit off-guard, but while the liquor was flowing, he figured he might as well be slightly transparent, “Well, I just love short hair on women, especially if it looks good, it really turns me on…”

“Wow! Really?” Lana responded. “I just thought guys preferred long hair. I was starting to miss my long hair…”

“If you want my two cents-“ He paused, slightly hesitating to finish the sentence “You could go even shorter”

“Shorter! This is the shortest I’ve ever had it. There’s no way I’d do that willingly” Lana protested.

Alex raised his eyebrows, “Willingly huh….what about……unwillingly?

‘Fuck, he really knows what to say’ Lana thought to herself. ‘Should I tell him about Sarah? No way. I can’t’

“What do you mean?” Lana coyly responded.

Suddenly, Alex got a serious look on his face, moved in closer and began whispering in Lana’s ear, “Let’s make a bet. I bet you that I can chug two beers before you finish one. If I win, we go to the shop right outside, and you get a haircut….with the only instruction being ‘really surprise me’… if you win, I need to do the same, AND I have to pay you $100.”

Lana’s heart skipped a beat as she realized now why Alex chose this particular bar. Her bob was absolutely perfect… but the thought of not knowing what the attractive barberette outside would do to it, was making her panties wet.

With the liquid courage running through her veins she responded, “You’re on!” and yelled to the bartender, “3 beers please!”

In what felt like a blur, Alex chugged his two beers before Lana could even get half-way through hers… but secretly this is what she wanted. ‘I can’t believe I’m doing this’ She thought as it all unfolded.

“Welp…. That settles that!” Alex exclaimed, “Time for your ‘surprise haircut’”

Just the words “surprise haircut” were enough to get Lana aroused. With her inhibitions loosened, Lana confidently stood up, and began walking through the door back into the barbershop. Alex followed closely behind.

Upon entering the storefront barbershop, they noticed the female barber sweeping up.

“Are you still open?” Lana asked the barberette.

“For about another 15 minutes, yes, are you asking for your boyfriend?” She replied, looking over at Alex.

Before Lana could respond, Alex jumped in, “No, it’s for her…she just lost a bet”

“A bet? That’s always fun…Come take a seat, so I can take you before we close. I’m Carmen.” She said as she motioned for Lana to go and take a seat.

“I’m Lana…and this is Alex” Lana responded. ‘I can’t believe I’m actually doing this’ She thought to herself as she walked to the chair, looking at herself in the large mirror in front of her. ‘I really like this bob…’

The barber station was bare-bones, with a large black barber chair with chrome accents, a single mirror, and a ledge for haircutting tools. As she sat in it, Lana noticed that the chair felt huge compared to the salon chairs she was normally used to.

“So, what are we doing today? What’s the bet? I’m trained as a hairstylist too, so I can do women’s hair too.”  Carmen explained as she put a tissue around Lana’s neck and wrapped the large white barber’s cape around her. “Your bob is absolutely perfect by the way…”

There was an awkward silence and Lana’s eyes met Alex’s in the mirror. “I want you to really surprise me.” She blurted out.

Carmen clearly did not expect Lana to say this and was caught completely off guard. “really surprise you!?” She paused and rubbed her hand on her chin. “There is one cut I’ve always wanted to try…and your hair texture would be perfect for it…are you sure you want me to really surprise you?”

“Yes. Do it.” Lana responded.

By now Lana’s panties and part of her black dress were soaked completely wet. Had she been sober, she would have analyzed the situation and felt shame about why this was turning her on so much. However, given that her inhibitions were lowered and she was clearly enjoying herself, she gave in to these feelings and enjoyed the anticipation and titillation she was feeling.

“Alrighty! Let’s turn you away from this mirror to really surprise you.” Carmen said as she winked at Alex.

Carmen turned Lana away from the mirror and toward the main walkway of the barbershop – the same walkway the speakeasy patrons would use to go to the back.

“Ugh. You have such pretty hair, it’s almost a shame.” She continued as she grabbed her comb and scissors.

There it was again. A statement suggesting a big sacrifice, or loss… or better yet… humiliation. Lana’s vagina was throbbing at this point and her juices were sliding down her leg.

Carmen combed all of Lana’s hair forward so that it completely covered her eyes, placed the scissors just above her left eyebrow and began cutting directly across.

*snip* *snip* *snip*

6 inches of perfectly straight jet-black hair fell in front of Lana’s eyes to her lap.

Carmen kept cutting until she reached the end of Lana’s right eyebrow, stepped to the side, and pretended like she was all done.

“What do you think, Alex? Good enough?” Carmen said, completely ignoring Lana.

“Well—” Alex began.

“Just kidding! Bangs would not be much of a surprise! Looks cute though” She responded as she placed the scissors above Lana’s right eyebrow where she had previously stopped cutting, and began to continue snipping away at the same length toward the back of Lana’s head.

*Snip* *snip* *snip*

‘Holy shit. How short is she cutting it!?’ Lana thought to herself as before re-releasing into the ecstasy of the moment.

Mountains of hair were sliding down the cape as Carmen continued cutting all of Lana’s hair at the same level of her bangs all the way across.

People going into and out of the speakeasy stared at what was happening as they walked by, many with looks of disbelief on their faces. Every time Lana noticed this, she enjoyed it more…since it made her feel like she was receiving some kind of public degradation.

When she was done, Carmen took a step back and surveyed her work.

“Much better. Bye bye bob!” She said as she grabbed the hair clippers and began plugging them in. “Now let’s get rid of the bulk on the sides.”

‘Holy crap, she’s going to shave my head’ Lana thought to herself as she saw Carmen fidget with the clippers out of the corner of her eye.

*click* *hmmmmmmmm*

Without attaching a guard, Carmen placed the clippers at the base of Lana’s neck. The cold steel blades, coupled with the strong vibrations sent tingles all throughout Lana’s spine.

“Head down, love” Carmen commanded.

Unable to utter a single word at this point, Lana was happy to comply, as she felt herself submitting fully to the beautiful woman chopping all her hair off, whilst her date looked on.

Carmen pressed the clippers firmly against her nape and moved them up forcefully, leaving no hair in their path.

“I was going to use a guard, but, you said to really surprise you, so let’s go for skin” she explained as she continued pushing the clippers slightly above the area where she just cut, creating a bit of an undercut. Carmen repeated the motion multiple times across the back and sides of Lana’s head until nothing but the faintest stubble remained on the back and sides of her head. The sensation Lana felt as Carmen held her head down while scalping her nearly brought her to orgasm.

*click* Suddenly the clippers turned off.

Lana began to raise her head, when she heard Carmen say “not just yet, I did say skin

With that, Carmen grabbed the foil shaver and began to run it all over the area she had just clipped, reducing the back and sides of Lana’s head to bare scalp. The shaver vibrated against Lana’s head, leaving her in a trance of pure euphoria. When she finished, Carmen turned the foil shaver off, and ran her soft hands around the back and sides of Lana’s head to make sure she didn’t miss a spot. The feeling of Lana’s fingers and palm on her bare scalp made Lana feel completely naked.

“Okay, head up, let’s take a look at this masterpiece” Carmen said.

Lana raised her head and her eyes met Alex’s. His jaw had completely dropped and he mouthed the words “you look amazing” to her. This reassured her, but she was dying to know what cut she received, how short it was, and whether or not it even looked good.

“I’m just going to even it up a bit and take it off your ears” Carmen continued, as she combed and cut more of Lana’s hair evenly all around, leaving it slightly shorter than it was before, so that none of the hair she had cut was touching the top of her ears. When she finished, she turned on the blow-dryer on to blow off any loose hairs.

“Ready? Here comes the big reveal” Lana said as she slowly turned Lana around to the mirror.

Lana couldn’t didn’t even recognize the person looking back at her. The haircut had completely changed she shape of her face. Her ears and hoop earrings were completely exposed, and the back and sides of her head were completely bald. The rest of the cut looked like a bowl cut or mushroom cut a child would receive. Frankly she thought it looked atrocious but reflecting on that fact just turned her on even more. Just three weeks ago she had thick, long, beautiful black hair that almost reached her waist which everyone envied. And now, she had a humiliating and unflattering bowl cut!


“I’m….BALD!” She blurted out…”A bald mushroom!” She continued on, as she ran her hands against her completely bare scalp, which felt like a foreign object.

“Well, that’s one way to put it… You did want me to really surprise you, though… I think we accomplished that today.” Carmen said, unfazed by Lana’s clear disappointed expression. “You still look cute, don’t worry…but the bob did suit you better.”

‘mmmm…yes, tell me more’ Lana thought.

“Alex, what do you think?” Lana asked.

“I fucking love it, you look gorgeous.” He responded.

“Well, at least your man likes it, he’s a keeper” Carmen Said.

The look in Alex’s eyes said it all. He was entranced, and judging by the bulge in his pants, incredibly turned on.

“That’ll be $25, who is paying, I need to get out of here.” Carmen continued as she took the cape off Lana, sending the mound of long black hair to the floor.

Alex immediately stood up and handed Carmen two $20 bills as Lana got up and looked at herself more closely in the mirror. While the haircut was not particularly flattering, Lana still looked extremely sexy in her tight black dress.

Alex then grabbed Lana’s hand and began leading her outside.

“Where are we going next?” She asked.

“My place.” He responded as they reached the street. Alex then pushed her up against the liquor store, kissing her with more passion than he ever had before and running his hands all over her bare head and new bowl cut…

Lana knew she was about to have the best sex of her life.

…To Be Continued

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