Using a Matchmaker

"Have you decided to bid on anything tonight?" the dark haired woman asked me.

"I put in one for the Mets package and the foursome at Winged Foot," I responded.

"Golf is not my thing, but I also bid for the Mets. Hi, my name is Patti. What did you put up for the auction?"

"Hi, Jason. And a weekend's use of my boat," I answered.

"Wow! that is some prize. I saw a few very large bids for that already."

"And you?" I asked her.

"A soul mate," she answered with a surprisingly straight face.

"Now I recognize you. Patti, from Matchmaker Millionaire. I have watched a few minutes while channel surfing."

"Just a few minutes?" she asked incredulously.

"I do recall watching the one with the train wreck girl wanting to date the young handsome guy, who really had no interest in her. Obviously, he just wanted some TV exposure. You advised her to go with the more appropriate guy, but she went ahead with her stud anyways. The audience knew what was going to happen, and it played out perfectly. The Train Wreck crashed."

Patti laughed, "That one did get good ratings. Bravo reran it many times."

"I find it hard to believe that your show actually works. I read you claim to have a 99% success rate, but outside sources discovered only 10% go on second dates. What percent of these people actually have a relationship for at least six months?"

"I will level with you here. Before the show I really did have great success with my clients. However, in television we don't want the boring couples. We are looking for some excitement. Unfortunately, that brings in the train wrecks, as you say."

We walked over to the auction table for her donation, and we found the auction card remained blank. "No one is willing to take a shot with you," I said. "I guess most of the people here are married or don't want to be embarrassed on television."

"I would make sure no one from here would be embarrassed. Bravo has actually given me the budget to film this episode with the donor getting full editing rights and the clout to kibosh the whole episode."

"That makes it a little more interesting. So, I can try the whole thing like a dress rehearsal. If it is no good, then it gets destroyed. I mean it won't show up on Youtube the next week."

"Make the minimum bid, and I promise you will have full control."

My 100k bid held up for the night, and I agreed to meet with Patti at her office the following month for the initial interview.

Four weeks later

"Hi Jason, this is my staff, Rachel and Destin. As you know we want to get some information from you about what you want from your soul mate. I looked up a bit of your background. You have a very successful private equity company, hence your generous bid. I also saw you were married once for a couple of years. Any children? "

"None that I know about."

"Do you want children? Some guys by age 40 have decided against it."

"I would still like to have some. I would not even rule out a woman with a child already, as long as the situation with the dad is not too complicated."

"What other things are you looking for."

"Athletic, adventurous, curious, likes to have fun but does not expect to party every night. Also, she must be empathetic to others. I don't want anyone one who thinks too much of herself."

"Like me?" Patti asked with feigned indigence. Rachel and Destin laughed along with both of us. "What about looks? Your type is athletic, so we can start from there.

"Not too skinny. Also, I like really short hair on women. Think Charlize Theron in Mad Max."

"Yes, she is beautiful with any style. Most men I know like long hair. Did you ex have short hair?"

"She did when we met in grad school, and she kept this beautiful pixie during the first year of our marriage. Her neck was always exposed for me to kiss. However, she said she felt more comfortable at work with longer hair, and I did not push her to keep it short. Over the next year the more we grew apart the longer she grew her hair. We finally moved on with little commotion. We had no kids and similar finances at the time, so the divorce went as smoothly as possible."

Patti brought our conversation back to the show. "We tend to get women with long stylish hair on the show, but we can arrange to have some short haired women come in."

Destin chimed in, "how about we get the women to agree to have their hair cut off on the show?"

"I like that," Patti and I said at the same time.

Everyone started to flesh out how to put the haircutting into the context of the show. Should all the prospects get their haircut after Patti screens them, or should I first meet them? That way I would know what they are like before they know about the short hair. After tossing around a few more ideas we came up with the plan.

Patti would screen about twenty potential women based on all the personality and character traits like she usually does. From the twenty she would choose a few, who agree to have their hair cut very short and edgy by a stylist friend of hers. All of these women would receive three grand for surrendering their locks on the show. We were sure some changes would occur, but the basic idea made sense.

Patti called me the next week informing me that the plan went quite well, and she had four women lined up for me to meet. I arrived at her office on Friday with some apprehension about the whole program. Did I really need to expose myself this way? I allayed my fears with the comfort of knowing I could just decide to kill the show at any time.

I sat at Patti's desk, and she showed me the profiles of the girls. They were all in their early thirties, had no children, looked athletic, and had faces that would become more beautiful with no hair to hide behind. "So, how did you bring up the haircutting to them?" I asked Patti.

"Once I knew I liked one of them as a prospect for you, I handed her a ponytail holder and asked her to put up her hair. I then had her look into the mirror behind my desk, and I asked her how she thought she would look with short hair. Most of them did not quite understand my question, until I explained what you were looking for in your new soul mate."

"Then they thought I was a freak," I joked.

"Only one. The others took the news in stride and asked how short. When I mentioned Charlize in Mad Max, they mostly gulped or blinked a lot. However, these four liked what they saw in you and are willing to undergo the transformation. Also, the $3000 does not hurt as an enticement."

"How do we proceed now?" I asked.

"I thought rather than getting to know the girls after the haircut at our usual cocktail party, you could talk with them as they are getting chopped. This way you can see how they think and act under pressure. I will also be there to guide both of you. Are you good with that?"

"Sure, sounds perfect. Who is up first?"

Patti handed me a biography, and I followed her into a makeshift hair salon. I sat down to review the information on Jamie. She spent five years after college working for a few cruise lines in almost every capacity on the ship. After that long at sea, she wanted to settle down and moved back to New York. She has been working for Ian Shrager for the past five years in his corporate office. All the while she has volunteered at an animal shelter. She likes hiking and sailing.

Jamie walked into the room, and I looked up at her. Patti did not include a picture with the profile, so I had to stifle my first thought that her long brown hair would look much better in thirty minutes. I rose to shake her hand. "Hi Jamie, Jason. How is the hotel business?" After a bit more small talk Jamie sat in the chair and began to discuss her haircut with Patti and Marcel. I listened carefully, as they all decided for a close buzz with short bangs.

Marcel began by brushing out her hair. He gathered up a ponytail and cut through it very close to her head. He showed Jamie and handed the hair to Patti for donation. Marcel took the clippers with a large guard and reduced Jamie's hair to about an inch all around. He then used the #2 to buzz her down to a quarter inch all around except in the front of her head. After using a razor and cream to shave her neck and around her ears, he took the scissors to form the bangs.

Throughout her transformation Jamie kept a straight face. She told me Ian was used to people with avante guard looks, and this would not be a problem at work or the animal shelter. Moreover, she had shaved her head one time at sea, when they crossed the equator. She really liked it, so she had kept it relatively short for the whole year after that. After thirty minutes I felt very comfortable with her. Jamie had all the characteristics I was looking for, and thought I would definitely choose her.

When Marcel finished, Jamie stood up and carefully felt every inch of her now spiky head. "I really like it, but I will surely shock some people at work tomorrow." We had a long hug and a short kiss. Patti told Jamie that a decision would be made today, and she would call her tomorrow with the news. "It was great to meet you Jason. Good luck with your search," she said to me as she left.

Patti handed me the next profile of Megan. She was a producer of some theater and television in New York and Los Angeles. She even appeared as an actress in a few roles. Right now she was taking direction classes at NYU. Megan had very wavy, unruly hair that was just meant to be hacked off. She also had a very pretty face and would handle anything that Marcel could throw at her. She sat down and told Marcel to shave it all off. "I have wanted to get rid of this wild nest for the past year. It is time to start over, and this situation could not be more opportune."

There was no way to donate any of her hair, so Marcel just put a #4 guard on the clippers and started right at the front of her head. After a few minutes Megan had a nice pelt of half inch fur. Marcel then removed the guard and shaved her head completely bald. He began to clean her off when Megan said, "all the way. Use the razor." Marcel did not hesitate. He lathered her up and shaved every inch of her head. After, he applied some oil and her scalp gleamed in the lights.

This time I was at a loss for words, and Patti actually had to prompt me ask Megan questions about her career and what she liked to do. I did learn that she ran the New York Marathon in 2015 and still enjoyed running all around NewYork. Before she left Megan had me rub my hands all over her head. "On our date you can have free run of this," she said with a big smile. She walked out seemingly relieved of her big burden.

"I don't know how the next girl can top that, but let's see," I confessed. Patti handed me the next profile. Abby was a freelance writer and contributed articles to many publications. Most of her work looked into changing social norms, and she also blogged about dating. "Patti, this girl is going to write about this experience in her blog regardless of whether I decide to move forward."

"She signed a non-disclosure."

"But she can still write something, and then we have to sue her. By that time the cat is out of the bag." I continued, "But it doesn't matter. I think one of these women will be my date."

Abby walked into the room beaming and ready to move forward. Her waist length red hair was already pulled up into a ponytail. She sat in the chair and discussed with Marcel a very tight flat top. Marcel had performed this cut many times on men and told her she would look just like a new marine. He immediately cut her pony and started to shear the remaining auburn locks. He eventually had the sides and back of her head tapered from a razor smooth shave up to crown of hair. He then meticulously formed a quarter inch flat top. We talked more about her writing, and I told her I wrote a few financial columns. I wished her well, and I told her I looked forward to reading about the experience in her blog regardless of the outcome. Patti even tore up the non-disclosure.

"I have saved the best one for last," Patti let me know as she handed me the profile. After a moment I realized it was the Train Wreck.

"You have to be kidding!" I exclaimed. "I wouldn't date her for anything."

"I know that but she has been bugging me for months to try again. I explained to her many times that she was not likely going to get picked, and that she had to get her hair cut. She agreed, anyhow. She wants the attention. Besides, I knew one of those three would be perfect for you."

"This just seems cruel. I have a better idea. Why don't you get your hair cut, and I will guarantee to go forward with the show."

"You were going to that anyhow, but I'll agree to your proposal for an additional 50k donation to the charity from the other night."

"Deal!" she exclaimed.

Patti told the Train Wreck there was a change of plans and sent her home. Patti came back into the room, and she sat in Marcel's barber chair. "Are you also going for a complete shave my dear?" he asked with a laugh.

"I don't think so, but a short pixie would work. Rachel, find a picture of Charlize after she grew out the buzz cut." With a picture in hand Marcel gave Patti a similar cut but even shorter. Patti would barely be able to comb her hair.

"You look ten years younger," I told her with sincerity.

"Not bad but it will take me two years to grow it out again. I am not sure I am going to be happy with this tomorrow. I may need a wig. Anyhow, let's sit down in my office and figure out who you want to date."

"I have to admit rubbing Megan's bald head sounds quite enticing, and Abby surely has a flare. However, I really felt a strong connection to Jamie. She exudes confidence and empathy at the same time."

"We all think that any of the three have potential to be your soul mate, but we agree with you to go for Jamie."

"What's next?"

"I will contact Jamie that you chose her. Do you have a time and a plan in mind for your date? We need to arrange the camera crew."

"I figure on Saturday I will pick her up for a hike in NJ and a picnic lunch. If things go well, we can use that Mets package I won for Saturday night."

I left Patti's office full of energy. All of that hair on the floor had my mind in the clouds and my penis trying to escape from my jeans. As I turned the corner to walk down Park Avenue I passed a café with outdoor seating. Immediately, I noticed Megan sipping a glass of wine. She was easy to spot with her bald head reflecting the sunlight.

"Hello Jason. I figured you would walk in this direction. I have been waiting around for over an hour tanning my scalp. Come join me."

I sat down and ordered a beer. Getting right to the point I told Megan, "It was a really tough choice, but I chose the Jaime for the date."

"No big deal, I really don't want to be on the show anyhow. But I did promise you the opportunity to rub my head on our date." She leaned forward offering her head for me to stroke. After one more drink and some serious flirting, we walked to her apartment on Madison Ave. I held her hand and occasionally nuzzled her neck, as many heads turned to view this bald beauty.

Megan lived on the 25th floor of one of the newer towers. She had a decent sized on bedroom, tastefully decorated with a big comfy looking couch. I sat down, while Megan opened a bottle of wine. She put on an indie rock mix, poured the wine, and sat down next to me in the couch. No small talk needed at this point. I clasped both of my hands around the back of her head and leaned forward for a deep kiss.

After what seemed like a half hour we unlocked our lips. I excused myself to the bathroom to pee and to get my erection under control. Megan entered the bathroom as soon as I flushed. "What, no knocking," I said in a startled joking tone.

"Nothing I am not going to be seeing a lot more of this night," she quipped. She opened the faucets on the oversized bath tub and poured in some bubbles. "Are you ready to soap up my scalp?" she asked rhetorically. Megan undressed in front of me in the bathroom. She pulled down her jeans revealing her a tiny thong, and that also quickly found the floor. No shaving needed down there I thought. Then with extra flare she pulled off her top and unhooked her bra revealing perky nipple on a pair of perfect B boobs.

She hopped in the bath staring at me, as I now undressed in front of her. I did not make as much of a production and quickly got in behind her. "Great tub," I said as I reached around her back and cupped her breasts. I pinched both nipples and started to lick her head behind her right ear.

"That tickles," she squeaked. She flipped over and looked at me with her blue eyes. "Stand up!" she demanded.

"But it feels so good holding you, and it is cold," I replied.

"Trust me. Stand up."

I stood shivering slightly, but that did not last long. Kneeling in front of me Megan started to lick my penis from my taint to the tip, while she fondled my balls. I cupped her head and guided her mouth onto the head of my cock. Within moments she had a rhythm going, and my dick swelled to its full girth and length. Pressing her shiny head towards my groin my penis disappeared. I held her there, and she used her throat muscles to bring me to a climax. As I started to explode, she pulled away offering for me come all over head and face. After letting me gaze at her cum covered face for a minute, Megan wiped away my semen with her hands and licked her fingers clean with a huge smile.

She turned on the shower, and I shampooed her scalp. I felt the firmness and every little bump. Amazingly, I started to get hard again before we finished a final rinsing. We patted down with a towel, and ran to her bed still quite damp. Megan laid back and pulled her legs up in the air. I buried my face into her groin alternating between her clit and her vagina. After inserting two fingers into her pussy, I put my pinky into her butt hole.

"Jason, get your finger all the way in there!" she cried. Once I got past the second knuckle she trembled as wave after wave of pleasure came over her. I stood up and watched this gorgeous bald beauty orgasm for what seemed like five minutes, while stroking myself to a full erection. Once she calmed down, Megan looked up at me. "Put that thing right in here," she said, now on all fours at the edge of the bed.

I moved in grabbing her hips and driving my cock deep inside of her. We got into a rhythm. Megan pushed back against me, as I pushed deeper inside of her with every thrust. "I am going to come right now," I told her. As I came again she felt my semen deep inside, and it triggered another wave of pleasure. It was not the same orgasm she had before, but Megan collapsed onto the bed face down fully exhausted. And I fell on top of her.

Eventually, I rolled off her, and we spooned under the covers. I am not sure how long we dozed off, but it was after 10pm by the time we ordered some Chinese delivery. "I should get going," I said. "I want to run in the morning.

"I have some of my brother's gym clothes here for when he stays over. They're clean. We can run together." I did not need any more convincing. I got back in bed, we put on a Law & Order rerun, and we fell asleep holding each other.

By 7AM we were both up ready to go. It wouldn't have mattered if Megan threw on an old tee-shirt and ripped gym shorts, she was going to look so hot with her athletic body and now hairless scalp. However, she did choose a very form-fitting razor-back top and a matching tight red bottom.

"Do you think I need a hat? I never had to worry about covering my head during the summer before."

"It is probably too early in the day to worry about a sunburn, but take it just in case. I can fold it up in my pocket for now."

We got in the elevator back to the lobby. Anthony, the doorman, said good morning, but it took him a moment to realize it was Megan. We did not indulge in further conversation with him and walked outside.