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"I noticed your accent, what part of Ireland are you from?"
"Dublin. But I've lived in New York for five years. Have you ever been to Ireland?"
"No, I've been to London, but I never made it to Ireland. My name is Jack," he said introducing himself with and extended hand.
"Maggie," she said extending her hand for a quick shake.
"How long have you been working here?" he asked her. "I live on 73rd but we have come to O'Donnell's a few times after we close up our restaurant. I don't recall seeing you before."
"I usually work here weekend days. This is the start of football season. So, we have a few of working the bar to handle the big crowds. Where is your restaurant?"
"We own Novella on 48th Street. The walk home helps us unwind, and O'Donnell's is open late."
"I'm glad you stopped by, are you on the way to Novella?"
"No, we are closed on Monday. My wife has a meeting near here, and I'm waiting for her to finish."
"Excuse me," she said. Maggie went to serve another patron.
Jack had almost polished off his beer when Maggie returned with a menu. "Another Guinness?" she asked.
"Please. And a cheeseburger medium. Oh, and I like your buzzed nape," he uttered.
"Thank you. It was a lot cooler to have with all the summer humidity. I'll probably grow it out for the winter." Jack chuckled. "What's so funny," Maggie asked him.
"My wife, Lisa, just had her head shaved, and she will remain bald for the next few months." Maggie looked at him with her mouth agape. "She treated her friend pretty shitty, and she agreed to this penance," he explained.
"That sounds pretty harsh. It took me a while to get used to having my nape buzzed. I definitely would not be happy with a bald head."
"Well, you could pull it off well, but I'm prejudiced to the look. I think almost every woman should try it."
"Maybe, if my boyfriend really wanted me to do it, and he was willing to buy me something special."
"I offered my wife jewels, trips, but she always refused. It took this opportunity to get her shaved, and it goes on for three months," he explained.
"It sounds like you are the beneficiary of this punishment," she alleged.
Jack confessed to her, "I did suggest it to her friend, I even paid her a lot of money. But her friend wants me to tell Lisa. There is no way she can keep lying for three months."
"You better tell Lisa, or she may never forgive you."
"Yes, but I love her bald", he thought to himself. "You're right. Better sooner than later," Jack lamented to Maggie.
Lisa looked at another text from Sarah. "I see you walking towards me. I'm sitting outside of Coffee Time café." Lisa saw Sarah and sat down in the seat across from her. "You look pretty good in that dress with your shiny head."
Lisa smiled and asked, "what do you want now?"
"A little privacy for this question. Did he tell you?"
Three Weeks Ago: The Setup
Jack asked Sarah to meet him for lunch at a restaurant near Union Square. Once seated Jack spoke to her, "hi, Sarah. It's been a while. How have you been, how is your new gig going?"
"Honestly, it's boring and they don't pay me enough for all of the annoyances. I manage a few properties. All I do is answer complaints from tenants, make sure the staff shows up on time and works properly, and keep everything within budget. But it's not as exciting as helping with the hotel, the restaurants and the theater, as I did at Fox Holdings with you and Lisa. Moreover, I miss everyone there, especially Lisa."
"How about we hire you back. I can even provide you with a signing bonus and a few other goodies."
"How much? And what goodies?"
"$25,000. And you can be part of my 40th birthday gift. It is my birthday next month." Sarah shot Jack a quizzical look. "Let me explain," he continued. "Remember that bob haircut you got last year. And how much I complemented you about it."
"You kind of got creepy with all the attention."
"Sorry about that. But I want to arrange for Lisa to have an even more drastic haircut. Maybe even a head shave. I've tried to convince her to cut her hair short for years, but she won't do it... no matter how much I beg or attempt to bribe her."
"If she's resisting, I'm not sure I want to be part of this. Even though we haven't gotten together in a while, Lisa is still my friend." She paused for a moment, "but what's your plan?"
"As you know Lisa has been in operations and sales for our holding company. I have managed the investments and the accounting. So, when we made that sale of one of our buildings to the investors last year, she had no clue about the taxes. It was easy for me to pay them out of the proceeds from the profits, but she thought we spent it on opening the new restaurant."
"Ok, but where do I come in?"
"I want you to sue us for harassment and that she forced you to quit."
"Lisa never harassed me. She was just being catty. She's never going to believe this."
"Let's try. You will have your job back with a nice bonus. And I will have the birthday wish of a lifetime, my beautiful wife having her blond tresses snipped off."
All through lunch Jack and Sarah discussed what details were needed to convince Lisa of the authenticity of this plot. Moreover, they had to persuade her to have her head shaved.
After they left the restaurant Sarah walked to Union Square Park. She sat on a bench and pulled out her phone from her bag. During lunch she figured she would humor Jack by going through the plan. Maybe just talking about it would be enough to pleasure his fetish.
However, there was no way she would go through with it without telling Lisa. Sarah dialed Lisa's number and waited for her to answer. She explained the last two hours with Lisa remaining very patient on the other end of the call.
"How did he ever think he would fool me with this cockamamie story? Of course, I know about real estate proceeds and paying taxes. And we always got along."
"I suggested he write a story about shaving your head, rather than try this convoluted scheme," answered Sarah. "But he thinks he can fool you."
"So, let's let him think he has fooled me. It will be his dream 40th birthday."
"Wow, I never thought you would go through with shaving your head."
"We need to make this as real to him as possible," stressed Lisa. Sarah recounted all the details from Jack's plan. Having an attorney send letters for a deposition and meeting at Fox Holding's office. "Let's give Jack some juicy repartee and a head shaving scene worthy of all the bribes he offered me. We can pretend this will be ongoing for months. Let him decide to put an end to it."
Sarah countered, "When I meet with him, I will stress he needs to end it after the first day. I don't want to play this game for more than a day or two."
"Ok, he's got to come clean that day. We are going to California next month for his birthday. I won't be visiting a barber on vacation," conceded Lisa.
They finished up all the plans and agreed to a date for the deposition in three weeks.
Monday Evening: Lisa Move's to Phase 2
Lisa stroked her bare scalp, and she still could not feel any stubble from the morning's shave. "He has not said a word," she answered Sarah.
"After you left Dan's barber shop this morning, I spoke with Jack. He promised me he would tell you, but I knew from the woody he had there was no way."
"You can imagine the boner he had, while I gave him a blowjob this afternoon," Lisa laughed.
Sarah continued, "your performance today was amazing. I could see your emotions in the mirror: fear, anguish, helplessness, and even a little joy."
"Sarah, you can play a mean bitch with the best of them, and you mesmerized me with your sadistic madam shit."
"How are feeling now that the deed is done?"
"Actually, pretty good. I feel free. I realize I don't need this perfect blond hair to feel beautiful. And from all the stares I've gotten lots of people agree."
Sarah told Lisa, "you do look beautiful. I saw plenty of men and women checking you out."
"And I don't mind what they see. I'm not ready to be naked, but I don't mind a few upskirts and beaver shots. I already teased Jack with my naked vagina on the Citi bike ride home."
Sarah laughed, "he wasn't jealous or uncomfortable with your exhibitionism."
Lisa responded, "not until we met our friends by the café on 72nd Street. The guy, Roger, let his hand linger on my head for a bit longer than Jack cared for." She hesitated for a few seconds, "I have a great idea to make him insanely jealous. If he does not fess up, I'm going to put him through the ringer."
"How can I help," asked Sarah.
"Come to the office on Friday. I'll tell Jack that you said the two of you agreed for you to start again next week. I'll fake being upset about it. I'm going to drive him crazy all week."
"By doing what, other than being mad at me?"
"Keep acting like a bitch. Keep the terror going. But be friendly like it's going to end soon. That will also keep him on the hook for this week, knowing it's not going to last three months. Moreover, follow my lead, especially around him."
"What if he finally tells you?" asked Sarah.
"He may confess, but I bet this baldie fetish of his will overwhelm his moral judgment. He's going to keep it going for at least another week. I'll throw in a few more blowjobs to keep him on the hook."
"What's your pay off. It can't be giving him lots of head and showing off your bottom to strangers."
"I'm going to make him believe this bald head of mine has caused me to lose all of my inhibition. Not just the fifty percent it really has caused. If he got jealous from Roger touching my head, wait until he sees what I have in store for him."
"I can't wait to see your plan in action from my new desk at Fox Holdings."
"See you Friday," Lisa said as she turned to walk back uptown.
Lisa felt the vibration from a text, and she looked at her phone. Jack texted her, "I'm still at O'Donnells. I ordered a burger."
Jack was watching another baseball game when Lisa sat on the stool next to him. Maggie walked over, "you must be Jack's wife. What can I get you?"
"Yes, I'm Lisa. A pinot Grigio, please," She extended her hand.
"Maggie." She replied taking Lisa's hand for a quick shake.
"Maggie, show Lisa your buzzed nape," Jack said.
Maggie twirled around, "it's a start," joked Lisa rubbing the top of her head. She got up to go to the bathroom. On the way back she stopped at the other end of the bar, where Maggie was pouring the two men their fourth shots of Jameson. "Maggie, I'll take a shot of that, too."
"Should I bring it over to your seat?"
"No, I'll drink it right here with these fine fellows." Maggie poured another shot for herself as well. The two men and the two women drank their shots leaving Jack by himself at the other end of the bar.
"Jack told me you had your head shaved, but he did not say how beautiful you look," said Maggie. The two men banged their empty shot glasses on the bar in agreement.
"I can see you have some experience with your buzzed nape," Lisa replied. "Would you like to touch my head?"
"Yes!" expressed both men.
"Maggie first," she chided.
As Lisa bent forward, Maggie walked her fingers along Lisa's scalp. Talking loud enough for Jack to hear Maggie continued, "I remember how much I liked rubbing my own nape a few weeks ago after a fresh shave. I think I'll reshave it after I get home. And maybe I'll take off some more hair."
"Our turn," said both guys reaching for Lisa's head. Lisa positioned herself between the men, and they took full advantage to grope her head. Lisa smiled and did not betray any emotion for a full minute, until she backed away from them. "That's enough boys. Maggie, great to meet you. Please bring Jack the check. It's time for us to go home."
She walked past Jack, "pay the bill. I'm going outside."
"What was that with those guys and their dirty hands all over you?"
"Ask Sarah," she said if someone wants to feel my head on Monday, that's part of the deal. I don't think so, but it's fine."
"No, it's not. That was not part of the papers you signed. I'm going to talk with her. And it is after 6PM, so don't do that anymore off the clock."
"You can talk with her at work on Friday. She said you invited her back to work," Lisa said with fake disdain.
"I thought it might help mitigate her anger to be around you."
"I don't think it will help. And seeing her on the other days is not going to be fun."
"Let's see how it goes," Jack said.
Lisa let it go figuring there was no more reason to fake being upset. "Ok, let's go home. I'm exhausted."
Once back in their apartment, Lisa undressed and put on a pair of shorts and a tee-shirt. On the couch she started flipping through Netflix looking for something good to watch.
"Hey honey, why don't you get into bed," Jack said to her while helping Lisa off the couch. "You've been asleep for a couple of hours."
"Wow, it's dark out. I can't believe I was so tired. I've got to go the bathroom and wash up. See you in bed, and don't give me that look. I'll take care or your little friend, again." Jack did not say a word about his ploy, so she was ready to set her own plan in motion. Even if that meant a few more blowjobs to keep his head in the clouds.
After the job she gave to little Jack, Lisa crashed back to sleep and did not wake up until 6AM. She jumped out of bed ready to start the day. After ten minutes in the bathroom, she put on her Lulu's for the gym. "I'll be back in an hour or so. I'm rushing to the 6:30 spin class," she yelled to Jack before slamming the front door.
When she got back home, she joined Jack in the shower. "How was your class?"
"Amanda and Stacy thought I was nuts, but they said I'm still beautiful. And I do feel that way. Also, I'm horny a lot." With that admission she grabbed his dick and massaged it to a full erection. She kept up the pressure with a soapy hand job, until she could see some pre cum oozing from the tip. After quickly rinsing the soap, she opened her mouth. In one swallow his cock was hitting her tonsils.
Jack grabbed onto the back of her slippery dome and held her in place for the few seconds he needed to deliver a cum shot down her esophagus. "Is this going to be a daily occurrence?" he laughed.
"We'll see. But you are going to have to return the favor tonight, or I may have to find someone else," Lisa retorted.
Lisa spent some time in the bathroom with her new products to apply her foundation and eye make-up. She even looked at a few you tube videos with bald women explaining the best applications. One video reminded her to make sure to cover behind her ears and down her neck.
She walked into her closet to dress. Lisa thought about the meeting they had today with Robert Angell, their operating partner for the hotels in Miami. He also happened to be Lisa's former college sweetheart.
Rummaging through her lingerie drawer she found her taupe colored garter belt with matching nude stockings. Lisa clasped the belt around her waist. She leaned against the dresser to pull one stocking up her right leg. She reached around the back of her leg to clasp the garter. She the attached the two in the front. Satisfied the stocking would remain in place, she pulled the other stocking up her left leg and proceeded to clasp it in place.
Lisa decided there was no need for any knickers. She always liked a few British words, ever since she spent a semester in London. Almost twenty years had passed, and she still remembered leaving her knickers at Robert's flat and doing the walk of shame commando quite a few times.
She chose a black pencil skirt with a hem a few inches above her knee. Moreover, the skirt had a slit up the front that rose a few more inches. She slipped on a pair four-inch stilettos to complete her killer look.
Jack walked into the closet as she gave herself one final look. "Lisa, holy shit. You look so hot. I could return that favor right now. But that will have to wait. We are meeting Robert for breakfast at 9."
"According to the agreement with Sarah at least we can take a cab today," she said with some relief.
They arrived at the café on third avenue only a few blocks away from the office. Robert was sitting at the table waiting for them. "Hi Robert," Lisa called to get his attention.
His leering eyes looked at her from top to bottom. "I know it's Lisa from the voice and beautiful face, but something's missing. I can't put my finger on it."
She slid over in the booth next to him. "Very funny Robert. Let me have your hand." She put his hand on the top of her head. "Don't rub too hard. It took a long time to get my make-up correct."
"Is this some fashion statement you are making, or do you have a reason for being bald."
"I lost a bet to Sarah. She lost twenty pounds, and I lost my hair. She is also coming back to the office on Friday. I'm sure she will be glad to see you."
They ordered coffee and omelets. While waiting for breakfast to arrive, Lisa slid next to Robert. "Jack, take a picture of us." The first picture had both of them looking at Jack and smiling. However, for the next picture Robert had his hand on top of her head. For another one he pulled her in close, and she rested her noggin on his shoulder. "I think we took a few pictures like this in London and other places."
"But you had your beautiful blond hair on my shoulder. I have to say your bald head is not a bad substitute."
Jack put down the camera. "That's enough pictures." By then the food arrived. They ate and discussed the operations at the hotels. "When will the pool renovations at the Allegro be ready?" Jack asked.
"In three weeks. That's plenty of time before the November rush. I'm extending my stay here in New York through the weekend to see family."
Lisa got up. "Excuse me a minute." She walked to the bathroom.
"How are you doing with the divorce?" Jack asked Robert. "Any new women?"
"Nothing special. And definitely no one a great as your lovely wife. Even bald she's amazing."
Jack nodded in agreement and they both looked at her sashaying her way back to the table. Jack took a closer look at Lisa's legs. He thought he saw a couple of bulges through her skirt that looked like a bra clasp. He wasn't sure, until he saw the welt of one of the stockings through the slit in her skirt. He looked at Robert, and saw his eyes were popping out of his head.
They finished their breakfast, while discussing the operations in Miami.
"Robert, I'll see you on Friday. I'm sure Sarah wants to say hello," said Lisa as they left the café.
After breakfast Jack and Lisa walked the few blocks to the Fox Holdings office. "What's with the suspenders and stockings. Sarah doesn't control anything today. You haven't worn that garter belt in years. Now today on a warm morning. What's up?"
"I figured Sarah would get around to this lingerie in a few weeks anyways, so I took it out for a spin."
"Robert sure seemed impressed. I know he saw your stockings up that slit."
"I didn't notice, and I don't really care. As long as I'm showing off my naked head what else matters?"
Jack didn't have much of a response. He was along for the ride. Her baldness seemed to have awoken the exhibitionist in Lisa, and she readily gave him head a bunch of times in the past two days. He wanted to see, where this slutty version of Lisa would lead. Any thought of spilling the beans vacated his brain, again.
At the office Andrea, the receptionist, and the other five employees could not believe that Lisa shaved her head. "I lost a bet with Sarah. If she lost twenty pounds, I would shave my head," she told them.
On Wednesday a similar feeling flowed through to Novella, where Lisa performed her job as hostess. Both the staff and the regulars had pretty much the same reaction: you look great, but what the fuck?
