Lesbian Billionaire

by Olivia Hampshire

  The girls, including Leslie, began to cheer. The freshman boys that were planning to rush the frat were also cheering. Some were whistling and yelling "Badass!" "Wow," Leslie said, approaching Debbie, "how did you do that?" Debbie laughed and told her, "Leslie my friend, you are one hot chick. And a hot chick like you needs to learn how to defend yourself." Leslie rolled her eyes, "What-ever, Debbie," she laughed. Then she helped herself to a cup of stale, foamy keg beer.

  Debbie felt a hand on her shoulder and she turned around ready for a fight only to see a hand raised in the air in a gesture of peace. "Stop, stop, stop!" the man said, "I just want to introduce myself to you. My name is Bob… what do you say we get out of here?" Debbie looked over at Leslie who looked happy as she got chatted up by a drunk freshman. He was offering her some tequila shots, which Leslie was all too happy to accept.

  Honestly, Debbie had no clue what to think of this Bob character, but for a guy he was very handsome and not your typical Dartmouth type. He had a real hipster look to him was a trendy pair of expensive glasses, wavy brown hair, and a stubbly beard and moustache. He was wearing a plain white tee shirt over a pair of very expensive designer blue jeans, and he flashed her a smile that was just do die for, lesbian or not. Debbie decided she wanted to know more about this Bob, and besides, it had been a night of firsts anyway. Why not entertain this charming young fellow?

  It was past one in the morning at this point and most everything in Hanover shut down promptly at ten o'clock, so Debbie was not quite sure where Bob intended to take her. She hoped it wasn't back to his dorm room. He continued past the rows of frat houses and dormitories, taking her to Wheelock Street, which was Dartmouth's main drag. As they were walking, Bob took the time to tell Debbie how impressed he was with her fighting skills. "I mean, honestly, I have never seen a chick take down a whole football team before," he laughed, "that was really something!" He flashed her another one of those irresistible smiles. Debbie smiled back. "Anyway," Bob continued, "I thought after such a work out you might have worked up an appetite. How about a bite to eat and maybe a beer or a cocktail at the Hanover Inn?" Debbie looked at him with one eyebrow raised. The Hanover Inn was one of the most exclusive, fine dining restaurants in the area, and it would surely be closed at this hour.

  "How are you going to get into the Hanover Inn at this hour?" Debbie asked, genuinely curious. "I have friends, trust me," Bob said, guiding her in the direction of the establishment. Trust him? Debbie laughed to herself. Well, I might be a lesbian but dang this is one hot guy and he seems to be on the up and up, so I will give him a chance for one night. They reached the Hanover Inn, which was right on the edge of the beautiful college green and was a beautiful, sprawling historic building. It was in a beautiful vacation and it had a beautiful view. Still, Debbie was sure they would not be able to get in, and when they approached the doors of the Inn and they were all locked up she smirked. She didn't want to be the one to say told you so, but she found herself saying it anyway. "Hold on," Bob said, "don't count me out just yet. Then he gave several loud knocks on the door. Sure enough, a peephole slid open briefly, and then Debbie heard the heavy clanking sounds of the door unlocking. An older man dressed in a butler's attire greeted Bob by name and welcomed him inside the Inn. He sat the couple down at a table overlooking the green and took their order.

  "Do you like to drink martinis?" Bob asked Debbie. Debbie confessed that she had never drank a martini before, but she was all up for trying one. "We'll take two Beefeater martinis, up with a twist, very, very dry and a couple of dinner menus. Please and thank you Herbert." Herbert nodded and went off to get the couple their drinks.

  "So who are you, Bob?" Debbie asks.

  "Ah, ah, ah," Bob reprimands, "first tell me who are you? Then you are free to ask me whatever questions you want." Debbie told him her name was Debbie Brown and she was a senior in the college and was triple majoring in languages so that she could become a Navy SEAL. "Wowsa!" Bob laughed, "that is a lot of responsibility you carry on your shoulders Miss Debbie Brown. Well me, I am a frat boy, I confess. I am a member of Sigma Fu, but I need to tell you right now, before you kick my ass too, that I don't agree with the way they act and especially the way they treat women. If I had been there when that whole situation started I would have stopped it myself, but I was up in my room studying and I only came down when I heard the commotion. My father also went to Dartmouth, I am a legacy kid, and he was in the frat Sigma Fu, so it was only natural that I had to join as well. I couldn't let down the family, after all." They laughed, and their drinks arrived. Debbie enjoyed the taste of her first martini, lightened up a bit, and they continued to have a good talk.

  Debbie discovered that Bob was bright. Not your regular old Dartmouth bright, he was a sort of genius. He was also one of the most open and caring individuals she had met since she arrived on campus. Definitely the nicest of the males she had met there. Bob asked Herbert to bring them out two lobster tails with extra butter, and they continued talking as they nibbled on the delicate crustacean meat. They ordered another round of martinis, and then another. They also went through a couple orders of lobster tail. Debbie had worked up a real appetite with all of that ass kicking. They were really enjoying their chat and getting drunker by the minute. When Herbert came back to clear away some of the dirty dishes Bob was just about to order another round of drinks, but Herbert gave him the most evil eye he had ever seen the butler give, and so he stopped.

  "Hey, Debbie," Bob said, "I want to apologize for getting you so drunk. I am going to have to be a gentleman and call this round our last. So what do you say we toast this last sip?" Debbie agreed, and they raised their glasses. "A toast to new friends," Bob started. "To new friends," Debbie continued. She drank the last of her martini and then continued, "to be honest, Dartmouth can be pretty isolating and as a lesbian it makes it even worse sometimes!" Bob choked for a second on his drink. "Did you say you were a lesbian?" All of his thoughts of banging this fine red head in front of him went out the window with a little fart noise. Debbie laughed and told him yes. "Sorry, I guess you must be regretting all these fancy drinks and lobster tails right about now!" Bob shook it off. "No way, it's cool. You know my mother is a lesbian. After she divorced my dad she moved in with her partner in a mansion in South Beach, Florida. She sends a private jet over some weekends so I can fly down and visit with her."

  "Sends up the jet, eh?" Debbie asked. "Just what does your mother do exactly?" Bob told her that the family had owned coffee and banana plantations in South America for a long time, and her mother lived off of all the profits. As for her partner, she is an international business attorney. Debbie was excited by the thought of these high powered, out of the box lesbians, and when Bob suggested that she come down with him to meet them some time, she was happy to agree. It sounded like a great idea. Bob told her that he often did the cooking for big dinners his mom held, inspirational talks of a sort that she gave to promising young lesbian women. "I'm real proud of my mom. I guess some guys might be angry or even creeped out when their mom ditches their dad for a chick, but I thought it was really cool. I am so happy she can be herself and be comfortable in her skin. I support her all the way," Bob said. Debbie was really happy to hear this and she thought it was super cool.

  "You know, I do a lot of college tours giving talks to lesbian martial arts groups," she told him. Bob said it was very interesting. "You might not know it, but there are a lot of forward thinking young men at Dartmouth that I cavort with. They might be hidden behind the scenes, but they are there. I think they would be very interested to support your activities. And they have a lot of money to help." And with that, Bob and Debbie struck up a friendship cum business partnership. Bob and his friends sponsored Debbie's speaking tours and they provided excellent catering, high quality promotional pamphlets, and other goodies. They also decided to sponsor a new space on campus for Debbie to teach Wing Chun. Not only did they have a lot of great conversations about advancing lesbian rights, but
Debbie gained an even bigger following of pupils. It was a very good partnership, and Debbie was counting down the days until she would have the opportunity to meet Bob's mom and her partner.

  Finally a good weekend came up and Bob invited Debbie down to meet his mother in South Beach. It was an awesome ride on the private jet. It was stocked, of course, with tons of Beefeater vodka and lots of martini glasses. The interior was done in a really cool minimalist style, with very interesting furnishings and fixtures. Had Bob been a woman, he and Debbie probably would have joined the mile high club, getting it on hot and heavy way high in the skies, but unfortunately for Debbie he had a penis and that just wasn't her bag, baby. But they did enjoy a nice boozy chat and by the time they arrived at his mom's South Beach mansion they were feeling nice and loose and liquored up.

  The mansion was massive and sprawling. It was a beautiful white stucco and the interior was mostly marble with big, echoing hallways and beautiful thick pillars. There were golden statues scattered about, replicas of famous works of art. There were also lots of original watercolors and paintings hanging throughout the house. "Wow," Debbie said, "you can really hear a pin drop in here for days." Every step she took in her high heels made a crazy loud resounding echo amongst all the marble. Bob shrugged, "it's a bit tacky, in my opinion, but my mom likes it and she can afford it so bully for her." Then he began shouting out "Mom," letting it echo through the hallways.

  A fabulous looking older woman greeted him, "Bobby, my boy," she cried joyously. She was a rail thin woman with a short gray bob and nice skin, dressed in a very expensive looking silk dressing gown with the most intricate embroidery Debbie had ever seen. "And who is this darling girl you have brought with you?" Bob's mom asked after smothering him thoroughly in hugs and kisses. "Mom, this is Debbie Brown," he said, "Debbie, this is my mom, Miss Marylynn Legrange." Debbie shook her hand and told her she was pleased to meet her. "Oh come now honey," Marylynn told her, bringing her in for a big hug and a kiss on the cheek. "Now, let me introduce you to my partner, Lisa," Marylynn said. "Honey, you did tell your girlfriend I am a lesbian, right? I don't want to run the poor girl off." Marylynn laughed uproariously. "Mom, she isn't my girlfriend," Bob groaned, "she is a lesbian too. She is a good friend and business partner of mine. You can't assume every pretty girl I bring home is going to bed with me," he laughed.

  Marlynn started calling for Lisa, and before long a pretty young blond woman appeared. She had a short hair cut and she was wearing a lacy bikini, with a sheer cover up. "Oh hello, dear," she exclaimed, seeing Bob, "I was just about to take a dip in the pool. I am glad you caught me before I got my hair all wet." She greeted Bob with the same customary hugs and kisses, and she introduced herself to Debbie as Lisa Melander. "Debbie here is a lesbian," Marylynn whispered loudly to Lisa. "Oh, lovely," Lisa said. They all had a good laugh at Debbie's expense.

  "Well my dear, you are lucky you caught us this weekend. Usually we are down in South America working at the coffee plantation and overseeing the holding company. But, even hard working woman like us need some time to relax at home every now and again," more laughter. "Come now, shall we all take a dip?" Lisa invited. They agreed, and everyone else changed into their swim trunks and took a nice long swim in the beautiful infinity pool out back. When they were done swimming they enjoyed martinis in the hot tub until they were so red and toasty that one of the butlers had to practically drag them out of the roiling tub and bring them large, cold glasses of water.

  That evening when everyone had gotten to know each other better and cool down a little bit they had a nice talk over a lavish dinner. Bob's mother certainly lived in style. Debbie was telling Marylynn and Lisa about her experiences at Dartmouth, and at one point she brought up when she had first heard a woman named Harriet Rothchild speak, and how incredibly inspirational it had been for her. The two older women looked at each other, communicating for a few moments with their eyes before bursting into laughter.

  "Harriet Rothchild, you say?" Debbie nodded. "Well, we know her quite well, honey." Debbie was taken aback, but the women explained to her that the world of super rich lesbians was actually quite small and it should come as no surprise that they all know each other. Debbie explained that she did not come from a wealthy upbringing and even after all her time at Dartmouth she was still a bit ignorant about how these sort of things worked. Marylynn shook her head and told her that was no good. "You won't rise to be an important CIA agent knowing nothing about the world of extreme wealth and power," she told Debbie. "We will have to give you a sort of crash course in the subject."

  So for the rest of her time in South Beach, Debbie learned about the ins and out of the super wealthy. Marylynn told her about people that were Debbie's age but had spent their entire lives traveling all around the world, living in lavish apartments even when they were in third world countries. They would live in big mansions like a slave owners plantation in the midst of desolation and poverty, reaping the economic benefits a small country had to offer and then leaving once they sucked it dry. Others were not so sinister, but they still lived crazy lives of affluence that new almost no bounds. There were kids who had their own beds from home flown around the world with them. Who had forgotten a teddy bear in Australia and a servant had flown out to Dubai just to return it. Because they couldn't just buy a new teddy bear. They had to have their exact same bear. It was a tribe of opportunity and riches, but it was also a group that was extremely petty and out of touch. The problem is, they control everything. So no matter how out of touch they are, one had to be in touch with the pulse of their lives and the rhythm of their money in order to make things happen in the world.

  Marylynn told her a little bit about the plantation life. She tried to run hers ethically but a lot of them were sheer exploitation. The kids of plantation owners went everywhere by private jet. They could ask their parents for $500,000 to start a new business venture or to buy a nice piece of property when they were in high school. By college it only got worse, and they typically blew through hundreds or thousands of dollars a year just in personal expenses with nothing to show for it. It was a totally new way to look at the world for Debbie, and she was honestly a bit disgusted by it. Sure, she had felt a bit above working as a dish washer, but she could not imagine how anyone could ever feel entitled to the sort of luxury that Marylynn was describing. And yet Bob was one of those children she talked about, how much money had he spent supporting Debbie's Wing Chun lecture series? How many extravagant expenses had he okayed, even ordered? It made Debbie shudder a bit to think she had already been sucked into this world without even realizing it. She had been staying at nicer and nicer hotels on the lecture circuit, eating more and more lavish meals, getting things like hour long massages upon arrival and fancy bottles of champagne in her room. And she had let it all go without question. She had become a pampered pet. Suddenly her dream of being a Navy SEAL seemed very far away. What SEAL gets hour long massages and stays in a five star hotel on a luxury mattress? It didn't fit the type. Then she heard Harriet's voice in her head, "Don't let anyone put you in a box." She wouldn't. She was going through a special kind of education, a sort of college in itself.

  Debbie was sorry when the weekend with Marylynn and Lisa were over. On the plane ride back, she told Bob that she was going to lay off the lecture tours until she graduated. She needed to buckle down and really focus. Debbie stopped teaching students, although she continued to practice Wing Chun more intensely than ever. She did away with all luxury and began to live like an aesthete, spending all of her time studying and working out. She quickly became a lean power house and a little bit edgy.

  Before she knew it, it was finals week at Dartmouth and Debbie was in her last meeting with Prof. Donaldson. She had really grown to love the man during their time together, and she felt her heart breaking at the thought of being without him. Their weekly meetings had always been the highlight of her week, and his kind words and his sensitive ways always uplifted her spirits. It was goin
g to be a hard life without him in her life. She steeled her nerves, commanding herself not to cry, and then walked into his office for the last time.

  "Debbie, my dear, how nice to see you," Prof. Donaldson greeted her, pretending like it wasn't the last time they would speak. "I want to congratulate you on your wonderful academic record and on your success as the first triple major at Dartmouth to graduate in four years. I know it has been a long, hard road for you but you have performed just swimmingly my dear!" Debbie thanked him for his kind praise. "Now, it is time to talk about next steps. What are you planning to do once you leave our wonderful establishment?" Debbie was still planning to go into the Navy, and he knew that. She told him so. "Yes, yes, of course," he said. "Well, along those lines, I have some very good news for you. I think you may be pleasantly surprised by what I have to say." Debbie waited, eager to hear what her professor was going to tell her. "Well, my dear, I must tell you again that you have a lot of very, very hard work ahead of you but by now I am entirely convinced of your abilities and I have no concern that you will be able to perform all the tasks required of you. Now the thing is, I have a connection at the US Naval Academy. Based on my recommendation of you, I will be able to get you into a program there, I am sure. I have told my connection about your triple major and your amazing language skills. I have also informed him about your intimidating martial arts technique, including your take down of an entire football team during an incident at a frat house." Debbie winced. She was surprised Prof. Donaldson knew about that. It was not really something she wanted her esteemed professor to know about.

  "Yes, yes," he continued, ignoring her discomfort. "Anyway, he is quite impressed with the idea of having a super smart, polylingual, Wing Chun black belt at the Naval Academy. Now, you would have to leave Dartmouth immediately after graduation and begin your training. I recommend that you enroll in computer sciences at the Naval Academy. That will be the most appealing to the CIA. And of course, while doing all this nerdy stuff you will also have to engage in some quite serious physical training if you want to be admitted into the Basic Underwater Demolition training that leads to becoming a Navy SEAL. But there is one catch here, Debbie, and it is a big one. As you know, no woman has been admitted into the Navy SEALs, ever. … Officially, that is. So here is the catch. My connection says that if you really turn out to be everything I have promised him you are, which is no problem, he will be able to put you through the same training process the Navy SEALs go through, but it would through a secret training program and no one would ever know about it. Now if you can be happy with that, then you will be all set to begin after graduation." That was the end of his speech. "So what do you think, Debbie?"