Best of Both Worlds

Patty Duke sat in the elegant restaurant waiting for her guests. She was a lady in her early 40's, elegant, confident and successful. As always, Patty was elegantly dressed and made-up. Her dark blonde hair was arranged in a bob-cut style around her face exposing the diamond earring strands hanging from her ears. The beige jacket over a caramel silk blouse was artfully cut to display a very generous bust line. The copper eyeshadow, heavy mascara and rather bright lipstick ensured people would notice her. She was a very successful business lady and dressed the part. She looked many years younger.

Her red-tipped fingers held a glass of white wine and she pondered why Margie Joseph had invited her to dinner. It had something to do with the business she was told. Margie was a client to Patty as was her husband Drake, the head of a very successful financial firm. They lacked nothing and, it seemed, had independent lives and an open but discreet marriage. They enjoyed life's pleasures. Margie indicated she was bringing a friend, a new client perhaps.

Patty used an euphemistic term 'Ultimate Personal Services, or UPS' to describe her business. In reality, Patty had a small stable of escorts, both male and female, that provided very personal services to the rich and famous. Her prices were exorbitant deciding that the higher the price, the better class of customer that could afford it. This also meant that such customers were a lower health risk. Importantly, discretion was essential and factored into the price. Before hiring her escorts, they underwent a thorough background check, many tests of general knowledge, politics, the arts, geography, history and much more. They had also to be able to satisfy every sexual whim of their clients and needless to say had frequent medical checks. Grooming was also high on the list. They attended conventions, parties, gallery openings and, on occasion, even intimate dinners. These dates always ended in the bedroom. The escorts were compensated well and knew they would have to be fit and perform to high standards. Because of high compensation and generous tips, the escorts did not have to work every day. Of course, some left and tried it on their own. They didn't have Patty's client list and ability to get referrals. Patty's business was also unique in that she catered to both men and women. Her client list was almost 50:50 split between the sexes. At the upper end of society, where money was no object and attitudes to sexual freedom were open, Patty had a very good and active client base with many referrals. She assumed Margie was bringing along just such a friend.

The UPS Company had been in existence for some 7 years now. Patty had started on this path in college where she studied Business Administration. The father of her closest friend in school and roommate was coming to visit Cindy. It was unfortunate timing as Cindy had a hot date with the leading scorer of the college basketball team. She had lusted after him for some time and was determined to bed him. Her father, a businessman, was visiting and had invited Cindy and her friend Patty for dinner. At the very last minute Cindy professed an urgent and important meeting with her professor which she could not shake off and promised her father that Patty would keep him company. It hadn't taken Patty much to captivate Nick, Cindy's father. On his next visit they arranged to meet privately, unbeknown to Cindy, and Patty found an admirer that gave her a donation to help with college. Nick spread the word discreetly and Patty had to move into her own apartment to entertain such clients and maintain discretion. She was now well able to afford this.

After graduation, she kept up her hobby using her money wisely from all she learned at college. After the first few years, she was able to increase her prices and be more selective in her customers and decided she could work just two or three days a week if she hired staff. She managed to hire the right girls to work with her and needed to perform less herself and administer and network more. Two years ago she had hired her first male escort to deal with older and rich ladies who preferred a night with a more virile younger man. This suggestion had come from Drake, Margie's husband, who availed himself regularly of Patty's escort services. He wanted to give Margie a discreet, safe and unique gift for her 50th birthday. Patty had found Peter, a thirty-year-old with all that she needed in his background, to be her first male escort. Margie had the greatest time of her life and used Peter's services very regularly after that. She was also a very generous client, devoted to Drake and seemingly in a loving open marriage.

Patty looked up from her flashback and saw two beautiful women walk toward her. Margie, the older was dressed beautifully in a black skirt and jacket with a snow-white blouse underneath; she looked ten years younger. Her makeup was perfect and she carried herself well. The girl beside her looked like a model. She wasn't much taller than Patty on those tall stilettos. Her sequin-studded silver dress with broad shoulder straps was modern, the skirt midway down her thigh exposing a magnificent pair of legs. Unlike many models, her bust was a tad more prominent but in proportion to her height. It was obvious she was beautiful and classy. Her makeup was a work of art and her bright orange-red lips on her full mouth promised great oral action. For a moment, Patty wondered if she was a potential client or escort.

"Patty, how are you?" Margie greeted her with a cheek to cheek kiss in order to avoid smearing her makeup. "You look great as always."

"Margie, fabulous as always too," Patty replied returning the cheek touch. "How are you?"

"Doing great as always. Meet my good friend Celeste, a prot�g� if you will. Celeste, this is the lady I have told you so much about," Marge said with a big smile.

Patty looked closely at Celeste and shook her hand. She was definitely escort material if she had the brains. If she was a client, she'd have to find the right guy. Peter, would not fit the bill as they appeared to be of similar age. The other male in her stable was a gentleman of Latin heritage but similar in age to Peter. Most ladies in Celeste's age were looking for older men who were still virile. Older ladies, like Margie, sought younger men like Peter. It would be a challenge to find a suitable escort quickly. Celeste obviously had money judging by clothes and accessories and this would be the deciding factor.

They sat down and immediately a waiter was at their table to pour out the wine Patty had chosen. Margie was a regular here and a big tipper.

"So, Patty," Margie began. "Let's have dinner and then adjourn to the lounge where we can talk quietly. You may talk freely in front of Celeste. We have shared some things." Margie was full of smiles.

They ate their dinner chatting over mutual friends and society parties. Of course between Patty and Margie, they had many stories, some of which could not be shared in public. Patty did bring up a variety of subjects, directing most of her questions to Celeste. She answered or contributed in that sultry voice which added to her charm. Her knowledge was broad and she appeared very sophisticated.They ate sparingly, all three ladies keeping a watch on their narrow waistlines. After dinner, which Margie paid for with a handsome tip to the waiter, they adjourned to the lounge,

This was quite a large room of dark wood paneling and leather chairs grouped closely for private conversations. It was also a smoking lounge and in spite of excellent air filtration, the smell of fragrant cigar smoke was in the air. The substantial tip to the waiter had secure the group seating in the corner where they would not be disturbed nor overheard. The waiter led them there.

Margie opened her slim purse and extracted a pack of cigarettes. It was a dark package. Patty had never seen the brand Sobranie before. Margie held out a cigarette for Patty and then Celeste. Patty was a social smoker and was intrigued by the brand. Margie flicked a gold lighter and lit their cigarettes. Patty and Margie inhaled deeply savoring the full flavor of the tobacco. Celeste took some light puffs.

"I told Celeste here that she should learn to enjoy a post-prandial cigarette. Or post-coital after heavy sex, of course," Margie smiled and inhaled again. Patty observed how Celeste took the cigarette gently between her lips to that red mouth. It was erotic.

"So, Margie, how did you get on with Peter last time? You must have worn him out as he asked for some downtime," Patty said enjoying the smoke.

"As usual, Peter was a star. Did he tell you what happened?"

"Oh no, we never discuss that. It's a private thing and as long as there are no complaints, I don't get involved," Patty replied.

"That's good policy. Peter is very good at what he does and I am very happy with him. Totally." Margie inhaled thoughtfully. "Celeste knows what happened and that's why I invited her here to meet you." Another drag on her cigarette.

"I don't think I shared with you that I have some unusual sexual tastes," Margie said leaning in closer. "Over the last few months, I have given in to a pleasure I had ignored. I persuaded Peter to let me use a strap on. I let him perform, then have a short rest, he would then use his mouth to clean me up. I would finish the session by using my strap on to bring me to another enormous climax. Peter was most accommodating and indicated he had some bi-sexual leanings." Margie stubbed out her cigarette and lit another. Patty and Celeste had not yet finished theirs.

"In any event, at the last session, I had lubed Peter up intending to fuck him senseless. He had brought me to an incredible climax. He was then eating me out as he normally does. There was a sudden noise and Drake entered the room. His meeting had finished earlier and he was in an extremely good mood and horny to boot. He saw Peter's naked arse as he pleasured me orally. I saw Drake take in what was happening, shed his clothes exposing a massive hard-on. Peter was a little surprised when Drake pushed into him hard from behind. To his credit, he didn't miss a beat and continued to lap me clean. Drake was so excited, he thrust hard into Peter sending his tongue deep into me. I came again in a huge wave at the same time as Drake. I later discovered that Peter too had erupted on the bedsheets. It was incredible." Patty was now smoking her second Sobranie and was visibly excited at Margie's description. Celeste had stubbed out her cigarette and had a smile on her face as if transported into Margie's bedroom.

"Patty, it was amazing and it didn't end there. Of course, I had a short break for a post-coital cigarette. I was feeling full of energy and needed to use my strap on. I just turned to fit it and almost orgasmed again. I saw Peter with his arse exposed now sucking Drake. Of course, now I gave Drake a good view of my strap-on deep in Peter whilst he brought Drake to a climax again with his mouth. Patty, that was the most amazing night and I am not surprised Peter needed some time off. Drake raved about it the next day,"

"Amazing," was all Patty could say. She had not realized Peter was bi- sexual. Nobody had requested this service and she didn't know if Peter provided it to other clients. Most did not let their partners know about the use of escorts and participate as Margie and Drake did. She wanted to hear about the reason for this dinner. Interesting as it was, there didn't appear to be a business opportunity.

Margie appeared visibly excited. She lit another cigarette and handed it to Celeste who looked at Margie and took it with a smile. Patty could sense a closeness between the two. "As I was saying," Margie continued, "Drake and I discussed this. Obviously, we both have bi-sexual leanings but cant and don't want to bring them out into the public domain. Being seen with the opposite sex enhances our images." Margie took a deep drag and looked at Celeste. "So, Patty, let me ask you a question. If Celeste here had bi-sexual inclinations, do you have anyone who could be a partner? Celeste and I have .. well, you know, had some fun."

Patty looked at them both. This was a new and unusual request. "I don't have anybody that comes to mind. I haven't explored the idea but could ask some of my girls."

"What if Drake needed such a bi-companion? His 55th is coming up and I thought I could give him a nice experience."

"Well, except for Peter, I don't know of anyone. I didnt know about him till you just told me.When is his birthday? I can try," Patty said sensing another good opportunity.

"It's less than a month away. It would be nice to invite this person to the party and, at the end, send Drake off to the bedroom with this person. It would have to be very discreet of course. Can't make it that obvious to our friends."

"I can try to find somebody," Patty replied. "Does he have any preference?"

"Well, somebody like Peter, I guess," Margie replied. "Drake was very taken with Peter's attitude."

"Won't be so easy, but I'll get on it." Patty was sure Margie would pay handsomely for the proper escort. "How about Peter?" Patty sensed a big financial opportunity.

Margie looked at Patty. "We don't want to make it obvious to our friends that Drake has such leanings. Definitely not good for his image and business. Besides, he has experienced Peter now."

"Oh," was all Patty managed to say as she stubbed out her cigarette.

"Celeste, do you want to tell Patty or shall I?" Margie turned to Celeste who looked at Margie and then at Patty. Celeste brought the cigarette to her full lips in slow motion, drawing in and then exhaling a stream upward. Patty needed to get Celeste into her stable. Her movements were incredibly erotic. For a fleeting moment she thought about Celeste taking a cock into her mouth as erotically as the cigarette. The man would spurt before she got her mouth to the tip.

"Why don't you explain?" Celeste said in that sultry voice. "It was your idea."

"Patty, do you remember that scene where Marilyn Monroe jumped out of a cake at JFK's birthday? Before our time but you've seen the pic, right?" Patty nodded. "Well, wouldn't it be a hoot if I introduced a girl to Drake and indicated she was his birthday present for the night..."

"I have plenty of girls..." Patty interrupted.

Margie looked at Patty, took another cigarette and offered the pack around. Patty accepted and Celeste hesitated. Margie's look was enough to persuade Celeste to accept a cigarette and light. "Let me finish, Patty," Margie replied blowing out smoke.

"So this beautiful girl hangs around Drake and all our close friends will see that she is clinging to him. They would all envy Drake, of course. I'll put the word out discreetly that she is my present to Drake. Our friends know about our lifestyle. At the end of the evening, I invite Drake to take the lady to bed. Of course he is delighted. They go upstairs and, let's say, get down to business when Drake discovers that the lady has something quite big and hard tucked in her panties. This special lady has only two openings. Drake gets the boy and the girl!" Margie inhaled and blew out smoke. "What do you think?"

Patty took a deep drag and looked at Margie. "I wouldn't know where to find a girl like that so quickly," she replied.

"You know a girl like that could be very interesting for people like me. They have an opening I can fill with my strap on. And, interestingly, they will have their own natural strap on that can fill me. There will also be some juice I can enjoy."

Margie looked at Celeste. "Would you be interested in such a girl, Celeste?"

Celeste used that slow motion of the cigarette to her mouth, inhaled and blew out smoke. "Seems that would be the best of both worlds. I would like it very much."

Patty needed to take charge here. "Well, there are many in the TG community I can talk to. I'd have to be very selective, of course."

"Drake can have a beautiful girl on his arm but who has something extra between her legs," Margie added. "It will be a big and very pleasant surprise. She would need to be able to mix with our friends and be like one of your regular escorts, of course."

"This could be a new service you can provide to girls like Margie and me," Celeste added in that sexy voice. "Men like Drake would be particularly interested to explore their 'other side' discreetly."

Patty saw Dollars floating in the air. These special girls would bring in huge premiums. The only problem would be to find such an attractive and acceptable boy-girl. She knew of some who would provide perfect companionship with their mouths and holes, but not meet the cultural side to clients like Margie and Drake or even Celeste. She might need to visit some of the special clubs and ask around if there were suitable candidates.

"So, Celeste might know somebody that could fit the part well. Of course, she would have to be compensated well," Margie said.

"Well, of course," Patty replied. "I take good care of my staff. When can I meet her? Is she a TG? On hormones? Is she good looking? Convincing? I have some questions."

"No, she's not on hormones," Celeste answered. "She is not a transsexual and looks beautiful. I think the term is a transvestite. She dresses as and when she wants to. Don't you think so Margie?"

"Oh my God, Patty, you won't believe it. Celeste introduced her to me. She is truly beautiful, performs well with both men and women, and I would hire her regularly. Drake would love her. We might even try a threesome." Margie was enthusiastic. "I saw her transform with Celeste's help. She wouldn't let me take any pics or videos. It was amazing." Margie stared at Celeste for a moment and smiled.

Margie continued, "Celeste took me to this apartment where I met him. I mean it was a man in a panty. He had hidden his man bits. His body was nude of all hair. Celeste took something out of a box and two minutes later a woman was standing before me with a pair of very realistic breasts. She had glued the breasts onto his chest. I would be proud of those babies. Then a small corset, garters, stocking and Celeste chose a black mini dress for her. She sat down and began her makeup. The same stuff we do but adding false eyelashes and grey eyeshadow. The lipstick was a bright red, similar to Celeste's now. She pulled on her wig and got into 4" heels. My God. A beautiful woman stood before me. It took her almost two hours. I did not see her boy parts then but Celeste had seen them, and perhaps even played with them," Margie smiled looking at Celeste who was busy bringing the cigarette to her lips. "If I hadn't seen the change with my own eyes, I wouldn't have believed this woman was a male. Of course, I had to sample the goods later that night before I decided to give her as a present to Drake. She was everything and more I needed and wanted." Margie paused for a moment and looked at Patty. "Have you been with a girl, Patty?"

This was not a question Patty expected. Her own tastes and sexual preferences never played a role in her business. In the early days of college life, she had played around with Cindy but it was mostly in an inebriated stage. She didn't want to admit her lack of experience in this area as the owner of a successful escort agency. "Of course," she replied. "Like you, I am very selective." She had to take a deep drag to focus on her thoughts and distract from further explanation.

"So, how long have you know her?" Patty asked turning to Celeste. "Is she reliable? We don't let our valued clients down."

"I have known her for some time," Celeste answered in a way that Patty interpreted as a very personal relationship. "I think she would be perfect under the right terms."

"Terms?" Patty was alarmed.