A Lesson in Humility Ch. 02

Monday Post shave: Jack's Deception

Sarah stood in the doorway of Dan's barbershop watching Lisa walk west on 14^th street towards Union Square and for her makeover at Sephora. She felt an arm wrap around her shoulder, "I almost gave it away," he whispered.

Sarah turned around to see him with a goofy smile. She glanced down to evade eye contact and saw he still had quite a bulge in his pants. "Jack, I am surprised you were able to hold out watching me shave Lisa's head," she said looking him square in the face.

"She just sent me a selfie. Look!"

Sarah took his phone and looked closely at the picture. "Hey Dan, you are right. That oil does light up her scalp with sunlight." Dan did not really hear what she said, but he nodded and continued to clean up the Lisa's blond hair shards from the floor.

"I texted her the contractor canceled the meeting due to a family emergency, and I would be back in the city by eleven," Jack said.

"Just in time for her makeover," they both said simultaneously.

Jack handed Sarah an envelope, and she asked him, "Are you going to tell her today like we agreed?"

"Maybe after we get home later today. I want to see her adjust to her bald head. How many times will she flip her imaginary hair, how many stares will she get from strangers, and how will she handle the anguish of knowing this will happen again next week?"

"Jack, I cannot keep up this revenge thing for three months. I went along with you for a few bucks and because she got out of control and too full of herself. But she is still my friend, despite how I acted towards her the past couple of days. You had me get all indignant and fake my anger over Lisa just being Lisa. How the hell she fell for this ruse, I will never know." Sarah added.

"You were so convincing, and your lawyer was great."

"She's not even a real lawyer, but she played one on Law and Order last year."

Jack laughed, "at least mine was a real lawyer I paid to sound smart. I have to get to Sephora and meet up with Lisa. I will settle this with her by tonight." With that promise he opened the door and jogged towards Union Square.

He arrived at Sephora and walked around a few of the make-up counters, until he saw Lisa sitting in the chair having her scalp powdered. "Hey Honey, I got here as soon as I could," he stammered with authenticity of seeing Lisa bald for the first time. Well at least for the first time with Lisa aware of him.

"What do you think about the loss of my blond locks. Pretty slick, but this nice young lady is muting that shine."

"I am dumbfounded. You really look more beautiful, than you did with that blond ponytail I held last night. I am sure it feels great, too."

She slapped his hand, "Jack, you can't mess up Emma's hard work with those lecherous paws. Calm down and watch her finish my makeup."

Emma had been briefed by Sarah to accentuate Lisa's eyes. She did not go overboard with smokey liner or a huge amount of mascara, but she used a blue pallet to enhance Lisa's aqua eyes. She applied more foundation to cover a few of Lisa's minor blemishes. Finally, Emma used pink hued lipstick to complete Lisa's transformation. She handed Lisa a mirror to inspect the result. The former blond now commanded the floor as a bald knockout, and Jack could not have been happier.

While a few of the young women shopping did not pay attention to Lisa, their boyfriends surely ogled her as she strutted out the door. Jack even overheard one kid try to convince his girlfriend to go to cut off her hair.

Lisa tipped Emma for her hard work, and she paid the cashier for the new make-up she needed to keep her looking great for the few months.

"Sarah texted me instead of going to the bookstore, we could walk around the outdoor market in the Square."

As they crossed the street to get to the farm stands lining the perimeter of Union Square, Jack took a long look at his wife walking just a few paces ahead of him. He glared at her feet and up along the leather boots to back of her knees. He thought this was one of the overlooked sexy parts of any women no matter how skinny or how fat the leg. Jack continued looking at her pink hued hamstrings to the bottom of her leather mini.

On the other side of the street Lisa pulled out her wallet from inside of her bag. However, it slipped from her hand, "Damn!" she muttered bending over to pick it up.

She caught Jack off guard. He loved a good upskirt like any other man, but he got a full view of his wife's naked ass. He froze in his tracks just gawking at this wonderful site, like he would if some random woman gave him a full moon. After a brief moment he realized that was Lisa, and he ran up to her to block any others from seeing her bare bottom.

"What was that?" he asked. "I thought you were going to wear boy shorts under that skirt."

"I wore them over to the barbershop, but they were soaking wet by the time Dan finished polishing my head. I am not sure, if I peed a little from nerves, or came a little from the arousal of the shaving, or if I just sweated a little from the warmth under the cape."

"So why not buy another pair?"

"I was going to before Sephora, but Sarah said to go commando the rest of the day. I thought she would let up on any upskirts, but she just texted me to give you a full view." Lisa paused for a moment to read another text.

Of course, it was Sarah, "Nice view of your ass. Don't worry about anymore forced bending, but you should be careful. That skirt is very short. I see Jack is with you. I would like you to have him take a few pictures of you comparing various types of produce to your lovely bald head."

Lisa led Jack to one of the stands with a variety of gourds and melons. She picked up a honeydew and held it on her right shoulder. "Jack, take a picture of me and twin sister." He clicked away as Lisa posed with a pumpkin, a watermelon, and some kind of round squash. When she posed with an eggplant, Jack laughed. "I think that vegetable looks more like my twin," he said pointing to his groin.

They left the Square with fresh vegetables for a pasta primavera and an apple pie for dessert. Lisa remained upright for the next half hour, so no other lucky guys and gals got another flash of her ass. However, Lisa got plenty of stares up and down her body and received many compliments on her brazen look.

They walked over to Sixth Avenue, where Jack hailed a taxi. Lisa grabbed his hand and reminded him, "No taxis allowed. We can take a subway or a bus back up to our place."

Jack replied, "how about a Citibike? We can strap the food into the baskets."

"I have on a miniskirt."

"Let's go into CVS. I am sure you can find panties."

"Or I can flash my beaver all the way up Sixth Avenue." With that declaration Lisa undocked the bike and secured her grocery bag. She straddled the bike and stood up to peddle to the bike lane on left side of sixth. Jack rode about twenty feet behind Lisa watching heads turn, as the bald goddess exposed her vagina to all the voyeurs.

As much as he loved the idea of an exhibitionist wife, Lisa was his wife and flashing for three miles through Manhattan might be too much. He consoled this thought by knowing that it would end tonight with his confession to Lisa about the gaslighting he devised.

They docked the bikes by their building on West 72nd. As they walked past a favorite café with a few open outdoor tables, Jack took Lisa's hand and led her to sit down. The waiter handed them menus poured two glasses of water. "Hi Jack, and Lisa? Is that you?" questioned the waiter.

"Yes, it's me. Roger." I donated my blond mane and decided for a fresh start. Ridding myself of my sins, so to speak."

"I think you look stunning," he replied.

"So do I," piped up from the woman sitting behind Lisa. Her male companion also gave a thumbs up.

"Jack, it seems like my bald head is a hit, today."

"Yes, it does. And according to Sarah you have at least three months for more compliments," said Jack continuing the ruse for moment.

Rather than sit at the café for lunch, they decided to walk to Central Park for a picnic. While Lisa waited for their sandwiches and spreads, Jack ran to their apartment to put away the vegetables and for a blanket and some beverages. Upon his return he saw Lisa talking with two of their friends from the neighborhood. Jack waved to Carl and Debbie.

"We walked past Lisa, then turned around realizing it was her. And we had to ask, what happened?" explained Debbie.

"I'm sticking with the fresh start story. Anything others may think is all conjecture," said Lisa with a laugh.

"Well, you can really pull it off," Carl complemented her. Jack could see the sincerity in Carl's roving eyes.

"Can I touch your head?" asked Debbie. She pointed to Carl's full head of hair, "I've haven't touched a bald scalp, since my grandpa's many years ago."

"Sure you can, but it's a little sweaty from our bike ride." Debbie paused for a second then lightly ran her fingers on the top of Lisa's head. Lisa smiled, then motioned for Carl to cop a feel.

Carl did not hesitate and went beyond a light touch. He palmed the crown of Lisa's head, and he let his hand linger on her scalp until Jack swatted it away, "Hey, that's enough," he reprimanded Carl. Before more was said, Roger returned with their food. "We are going to the park to eat, see you both later," said Jack with some disdain.

"Don't mind him," Lisa said to Carl. Jack hasn't had his turn yet. I had make-up on my scalp before our ride, and I told him to keep his hands in his off."

The couple crossed Central Park West and followed the path to the Sheep Meadow area on the south end of New York's marquis park. While this was a Monday, they saw hundreds of people walking, running, and biking on the closed roadway, and even more people enjoying lunch or a nap on this beautiful day.

They found a spot under a tree to provide some shade, and Jack spread out the blanket. Lisa reached into the bag and took out the pasta salad and the tuna sandwich, along with plates and utensils. Jack handed her a water bottle, then he opened the Chardonnay and poured some into two plastic cups.

"To my new look, may it only last three months," Lisa said with a dry tone.

"I'm sure Sarah will give in sooner than that. She's just trying to make a point and get you to understand how you treat other people."

"That doesn't help me, Jack." She wanted to add the 'ass' suffix to his name but continued to talk to him. "I don't like her controlling me. I could probably deal with being bald for three months on my own accord. I could wear a hat or even a wig if I wanted, maybe even a bright red or blue one. But having to be bald all the time. And the whole Monday thing sucks. I have to go all over the place to get a fresh shave."

Jack saw a few tears on her cheek, and he took a napkin to dry them. "I'll talk with her and tell her this is too much. Maybe she will relent a little."

"Please try, I'm not sure I can do this for too long, and I don't like those punishments. A little stud in my nose might be ok, but a big ring through my septum."

She shuddered and more tears came. Jack embraced her, and he reached his hands up her nape. He wanted to feel her head all day, and he took the opportunity to rub her smooth scalp and press on the firm skull underneath.

Lisa did not prevent him from starting a thorough massage. She always loved head rubs, even through her mass of hair. However, this time her scalp bristled with energy, as Jack ran his nails along her pate. His fingers found spots to explore. He alternated between scratching the crown to caresses on her temples. After a few minutes Lisa said, "I'm hungry and horny. Let's eat, drink the wine, then get back home before I have you fuck me right here."

He responded while looking up her skirt at her exposed vagina, "My dick is so hard right now, as well." They gobbled down the food and swigged two glasses of wine so quickly, that when they got up their head rushes almost forced them back down to the blanket.

The normal fifteen-minute walk home only took them half that. In the elevator they kissed like teens in back of a movie theater. Once inside the door of their apartment, Jack picked up Lisa and placed her on the couch. He slid up her skirt enough to bury his face into her pussy, the one that had been aroused since she sat on bench in the barber shop.

Jack grabbed both of her ass cheeks to pull her vagina in closer, so his tongue could extend as far into her nether reaches as possible. He moved his right hand to moisten it with her juices. His wet pinky probed her anus, and he inserted it up to the second knuckle. Lisa squirmed. She generally did not like anything up her ass, but this day his pinky felt much better than all the conditions Sarah had stuffed in there during the negotiation.

By this point Jack lapped at her clit and had two fingers twisting around her warm insides. He could smell her aroma becoming muskier, and he could hear her breath becoming more frantic. Then she grabbed the back of his head and howled. After a moment to ensure she needed no more stimulation, Jack pulled away to watch his beautiful bald wife wriggle and twitch. He could see the waves of pleasure release all of the stress from the morning's ordeal. This picture along with right hand brought his cock to a full erection and ready for a lot of attention.

Lisa caught him looking at her and she smiled at him. But this one was different than the smile of post orgasmic pleasure she usually bestowed. He thought he saw a more meaningful smile. The melancholy she had since the previous night had disappeared. Maybe she would be happy for a while remaining bald knowing it brought on such a heighted sexual satisfaction. Moreover, maybe she thought this penance would make her a more gracious and grateful person in the future.

He pondered this for only another few seconds because Lisa had other ideas. She stood up and removed her blouse, bra, and skirt only leaving on her black boots. She unzipped Jack's pants and drawers. He stepped out of them, and she pushed him to sit on the couch. Still quite moist she eased her way onto his erection kneeling on the couch and facing him. She looked at him and asked, "am I the girl you imagined in your dreams all these years? Not the blond whose hair you pulled last night, but one with a slick scalp for you to caress."

She did not wait for his response. Instead, she flexed her knees and rode his pole up and down about a dozen times. Her breasts heaved in rhythm with her flexes. Now, she saw his look of impending orgasm. Lisa squeezed down hard on him and brought his hands up to her head.

Jack spasmed releasing a jet of warm semen into Lisa. He twitched again and again exuding the final drops.

Lisa did not cum like before, but his warm ejaculate did send a few ripples through her like and aftershock. She leaned forward to kiss him and expressed, "I love you so much. Thank you for helping me through this day."

Jack opened his mouth to divulge his rouse to her, but the words caught in his throat. All he only mustered, "you are welcome." He could not change her mood right now. He did not want to receive her wrath for his blatant dishonesty. He would tell her tomorrow morning before work. That way she most likely would give him the cold shoulder, instead making a scene at work. By the end of the day she would realize her torment concluded, and she could grow in her hair right away. She would be angry, but not as much as right now.

Lisa got up to look at her phone. "Let's shower. I got a text from Sarah. She wants to see me by the new apartment she's renting next month with our money. It's on 54^th St."

"I want to see it. I'll come with you."

"She said to come alone, but you can walk me there. Let's shower first. I'm ripe."

Lisa started the shower and liberally soaped her privates and asshole. Jack stepped in behind her. He took the soap from her hand to wash her back. He reached around to wash under her breast. Her under boob, as Lisa joked about that spot.

She traded some shampoo for the soap he held. "Rub it in really well and give my head another wonderful massage." While Jack worked the lather from her nape to her crown, Lisa soaped his privates from his butt to the tip of his growing erection. "You must have been thinking about this moment all day, she said as she kneeled in front. Something about a bald-headed blowjob."

Lisa grabbed his cock at the base and put his head between her lips. She gradually increased the pressure with her hand and added another inch of his erection down her mouth.

Jack also increased the pressure he applied to her head. This was not the first time she got him off in the shower. However, he could not believe the difference of having her smooth head in his hands, as opposed to a mass of hair. He also could not believe he going to come again so quickly. But he could not hold back any longer.

"Wow, baby I going to blow!" he shouted over the noise from the water. With both hands on the back of her head and Lisa's hands now at her side, Jack had free reign to extend his dick into the back of her throat. He held her there for a few more seconds relishing this moment for as long as possible. All he could say was, "thank you."

After one last swallow she said, "I'm glad that was quick. I could not hold down my throat much longer."

After drying off Lisa went to her closet and pulled out a couple of dresses. "Which one of these should I wear. Sarah said something short and wispy because it got a little breezy out. And only a thong this time. No boy shorts."

Jack pointed to the pink dress with the flowers, and Lisa put on a pink thong to match. They rode the elevator to the lobby, and they walked past their doorman. "Hi Lance," said Lisa. He just waved to them with a quizzical look, not quite believing that it was Lisa walking out with Jack.

As soon as the turned through the revolving door of the building, the wind caught Lisa's dress and blew it up for all to see her tiny thong. "You should hold your dress in place, or it will be above your head the whole walk," implored Jack.

"Sarah said not to hold it in place. It's part of the deal for the rest of the day. And I thought this would turn you on. You always liked when I accidently exposed myself."

"But not with this wind. It's too much."

"I'll text her for some relief. I hope she'll be kind."

"She will. I'll call her."

"No worries. She just responded I can do what's necessary," she said grabbing the hem of her dress.

They walked to 55^th St. with no more up-skirt incidents. "Good luck with Sarah. It's almost 6 o'clock, so her power is over for the day. I'm sure it won't be anything you can't handle," Jack gave her a big hug, and he kissed her on the lips and the top of her head."

Lisa pointed to the bar on the corner and said, "I'll meet you at O'Donnell's." As Lisa walked another block to find Sarah, he stepped into the bar for a beer. "What will you have?" the bartender asked Jack.

"A Guinness. Thanks," Jack answered looking up at TV. The Yanks led the Orioles 2-0 in the bottom of the ninth with Cole looking to close out a two hitter. "Cole is having a great season," he said making eye contact with the woman pouring the beer from the tap.

"I'm not much of a baseball fan," she said. "But come next Sunday, I'll be paying close attention to the Giants and my football fantasy team."

She left his Guinness to settle behind the bar. Jack watched her pour two shots of Jameson for the customers at the other end. As she walked over to them, nice ass, he thought to himself. But what really caught his eye was her shaved nape. She had it fully exposed with her red hair up in a high ponytail. She returned to his side and placed his beer on the bar.