A Sweet and Sassy Match

by Stevie MacFarlane

  “About twenty-five percent of my clients are nice normal men; well, as normal as you can be when you’re wealthy to the point of opulence. That kind of wealth comes with a price, and that price is often loneliness. When you are consistently the target of gold diggers and unscrupulous individuals, it becomes difficult to trust your own judgment. Sex isn’t the problem; you can buy sex. Love is another matter entirely. Sugar Babies does for those clients what they cannot do for themselves. We find them a woman, the right woman most of the time. Based on extensive research, communication and field work, we search the world for the right match.”

  “Where do you search?” Jo asked softly.

  “Everywhere and anywhere,” Sam replied. “We have found perfect matches in every corner of the world. Single, divorced, widowed women who are teachers, lawyers, doctors, waitresses, construction workers, bus drivers, you name it. Age is not an issue. We have matched women who were just of legal age and women in their eighties. It all depends on the client, and, of course, on the woman.”

  “How do they meet and what makes you so sure it will work out for them?”

  “Experience mostly, although I can never be completely sure. Our field workers know what physical and character traits to look for and cater to each individual client’s needs and wants. We arrange a ‘meet and greet’ with several couples and see where it takes them. Of course by that point our ladies have already gone through an orientation of sorts so they know what to expect and what the optimal outcome would be. After that, if both parties are agreeable and find there is indeed an attraction for each other, the contracts are signed.”

  “What kind of contracts? Like a purchase offer?” Jo asked, trying to hide the shiver that flowed through her body.

  “Of course not,” Sam replied firmly. “Everything that happens as a result of Sugar Babies involvement is consensual. There are as many different contracts as there are individuals. Some contracts are as short as sixty days, some as long as two years. During that time the parties have the option of extending their contracts or getting rid of them completely. We’ve had many contracts terminated upon marriage between the individuals. A good match is when there is love and respect as well as acceptance of the other person’s needs, both physically and emotionally; the more commonalities, the higher the success rate. We put a great deal of time and effort into each client and pride ourselves on promoting the best matches possible.”

  Jo sipped her wine as she thoughtfully considered the things Sam told her. This didn’t sound very much different from a regular dating service except for the extreme wealth part. She didn’t understand why Sam was so worried and decided to dig deeper.

  “What would an average contract between two such people include?”

  “As I said, the contract requirements are based on the individuals, but a standard contract would identify the length of the agreement. It would specify the living arrangements such as, is the woman willing to live with the man, or would she insist on private accommodations? Is it to be a sexual relationship or strictly platonic? Will she be expected to act as hostess at certain times, or is she a companion? As a rule the gentleman pays all expenses associated with the contract as well as depositing an agreed upon amount into her personal account each month the contract is in force. If, for some reason, the relationship doesn’t work out, we never want to leave a woman in a poor financial situation.”

  “So he is buying her?” Jo said with a self-satisfied glare. “I knew it.”

  “Not at all, Jo; they are each fulfilling a need for the other. Many times we are helping a woman leave a life-threatening situation, giving her opportunities she never imagined. Some of our women come from extreme poverty or abusive relationships. Some have health problems they can’t afford to treat; others are lonely or afraid. Believe me, Jo, we see very few unhappy clients; usually it’s the opposite. After all, the woman is actually in control, and if the client violates the contract in any way, she can walk and take her money with her, usually with a big chunk added on, as there is a fee associated with that sort of thing.”

  “What if the woman violates the contract? Does she still walk away with the money?” she asked with a smirk, thinking she knew the answer to that.

  “It depends on the violation and what clauses are in the contract. Naturally if she is abusive in any way the contract ends. If she steals from him or sleeps around, again the contract ends, and she leaves with whatever is in her personal account. But all payments stop immediately. If, on the other hand, she does something less serious, she may be punished.”

  “Punished? You’re kidding right?” Jo gasped.

  “Not at all; it’s not as common in this group of clients, but if acceptable to both parties, a clause is sometimes added.”

  “Wow, I can’t believe this. But I guess if this is what some people want, I can accept what you do, Sam,” Jo said. “I’m a little shocked right now, but give me some time. I don’t want to lose you Sam,” she told him with a blush, as she scooted closer to him.

  “Get back in your corner, Jo, there’s more,” Sam instructed, despite how much he wished he could leave it at this and take her into his arms.

  “More?” she gulped, “Shit!”

  Sam raised his eyebrow at her language and nodded. Picking up the wine, he poured some into her glass and settled back.

  Chapter Six

  Sam crossed his legs, letting his ankle rest on his knee. Other than a slight twitch of his foot, he appeared relaxed and confident. It was important to make this conversation as informative as possible, without getting upset. Johanna was sure to have a lot of questions, but if she would listen with an open mind, maybe he could save their fledgling romance.

  “I’ve already explained the basics of how Sugar Babies operates. The privacy and safety of our clients both male and female is of the upmost importance. Nothing in the history of the company has ever shaken that commitment,” he told her, watching as she nodded in understanding.

  “We serve three distinct types of clients, although it’s not unusual for some of the clients to crossover into different categories on some points, such as the punishment clause in the first group I spoke about.”

  “Our largest group of clients falls into what I’ll call the ‘Alphas’ for want of a better descriptive term. In practice, these men are referred to as Title II, for business purposes. It gives anyone working on the case a starting place in finding a good match. These men are usually much more dominant and their requirements more defined. They are more old-fashioned in their attitudes and are looking for an obedient mate. Most of them are the working rich and want a woman who is feminine and caring. Don’t get me wrong, they are loving and supportive men and usually inclined to incredible generosity. But they expect respect and obedience from their women. We have a higher rate of marriage in this group for some reason. They don’t mind women who are independent and successful in their own right, but when it comes to the relationship, they are the leaders. Punishment is almost always included in their contracts and they have no problem administering it to a misbehaving match.”

  “How enlightened; I take it whips and chains are involved somewhere in their contracts?” Jo growled, disgusted.

  “No, Jo, whips and chains are never in any contract written by Sugar Babies. If we get a client requesting those types of things, we immediately refer them to another agency. There are plenty of clubs out there that cater to those interests, especially for someone who can pay the outrageous fees these men can.”

  “Well thank God for that, at least,” she breathed out.

  “However,” Sam continued, ignoring her sarcasm, “most contracts for these clients will include spanking, paddling, anal discipline and loss of privileges. There may be more specific details regarding punishment, depending on the circumstances. As a rule, these clients are not interested in acquiring a doormat or a lapdog and quite frankly enjoy the challenge of a feisty female. On the other hand, many of our fe
male matches enjoy the idea of bringing such a man to heel. It almost never works out that way,” he laughed, “but they seem to enjoy the gamesmanship.”

  “What the hell is anal discipline?” Jo demanded as her face flushed with embarrassment. “Never mind,” she shouted, when he opened his mouth to answer. “I don’t think I want to know.”

  “I wasn’t going to tell you, Johanna. I was simply going to advise you to watch your language. That discussion can wait till we get to the last group of clients.”

  “I never want to have that discussion,” she insisted with a shiver. “Yuck!”

  “Nevertheless, we will discuss it, Jo. Now, do you have any questions regarding what I have told you so far?”

  “Yes, I do. How old are these men, generally? I can’t imagine where they would get such antiquated ideas about women, and I can’t imagine a woman agreeing to this type of relationship.”

  “The male clients in this category range anywhere from 23 to 65 at present. This isn’t something they catch, like a disease, Johanna. This is in their basic DNA as far as I can tell. The needs to love, comfort, protect and correct is part of who they are, how they see themselves as men. Frankly, I believe there are many more men who feel this way than not. Society has done everything possible to curb and destroy this in modern men. Of course having unlimited funds frees these clients to seek out exactly what they want. Are you ready to move on to the last group?”

  “I guess so. How much worse can it get?” she asked, more to herself than Sam. “Can I have some more wine?”

  “No, I don’t think so. You’ve had two glasses already and I want you paying attention. Don’t forget you still have a spanking coming for your foolishness today.”

  “Are you still harping on…never mind, continue your instruction, oh enlightened one,” she drawled, giving him a worshiping hand gesture and bowing her head.

  “Cute, Jo, real cute. I think you’ll be even cuter with your little bottom beet red, but I’ll continue. Have you ever heard of age-play?”

  That question made Jo sit up and take notice like nothing else could. Her mind scrambled for an answer, and she smiled when it came to her.

  “You mean like me wearing a short skirt, knee socks and putting my hair in pigtails while I try to turn you on? I have no problem acting out a fantasy once in a while,” she grinned. “Do you want me to be your little school girl, Sam?” she giggled.

  Sam shifted uncomfortably, just from the image she’d put in his head. Jo would look adorable and incredibly sexy with her hair in pigtails and her panties showing beneath her skirt. It was a game he was more than willing to play, just not tonight, despite the fact that he would probably have permanent zipper marks on his cock.

  “Johanna, your offer is very tempting, and I reserve the right to call you on it at another time, but for now I need you to be serious. The third and last group of clients I want to tell you about I’ll refer to as ‘Daddies.’”

  “As in Sugar Daddies, rich old men who want access to pretty young girls? That’s just sick, Sam. I can’t believe you would be involved in something like that.”

  “That’s a total stereotype, Jo, and not at all the kind of client we accept at Sugar Babies. For whatever reason, these clients are looking for a woman who is more like a child or interested in becoming that way. Of course we would never arrange any match for anyone under the legal age of consent.”

  “These matches are much more difficult to arrange and cover a broader spectrum of needs. Matches of this type can go from very simple role playing in which they have a perfectly normal relationship with occasional trips into fantasy for mutual sexual satisfaction, to a complete and total regression of the woman until she thinks and acts like a child of a certain age. She could have a closet with a few outfits for role-playing, or a complete nursery with a crib, changing table, rocker and all the paraphernalia carrying for a toddler or very young girl entails. Some men want an older child to care for, such as a teenager who needs guidance and discipline, others a baby girl to cherish. In all cases, these men want someone to parent, coddle, spoil and care for. They want to provide for any and every need their little girl has.”

  “Why would someone want this, Sam? I don’t understand the motivation.”

  “I’m not a psychologist, Jo. I imagine it runs the gamut from fetish to a genuine need to care for a child they were never able to have. For a woman, I would not be at all surprised to find she had a horrible childhood and is looking for the love of a man to replace what she never got from her own Daddy. Another explanation could be that she had a perfectly wonderful childhood and longs to return to that carefree period of her life. Many women who are interested in this type of relationship seem to have high profile positions with tremendous responsibilities and stressors. It’s possible they wish to spend their free time being carefree and taken care of by a loving mate. I don’t claim to understand it in its entirety; I do, however, know that most of the matches we make in this area last a long, long time. I can’t say forever, but I’m willing to bet most of them do. I have yet to have a client break this type of contract, and many of them marry. The people who make this type of commitment to each other are often completely under the radar, living perfectly normal lives until they walk in their front door each night. Then the woman becomes the child, and her Daddy takes over.”

  “Are all of these relationships sexual?”

  “I would say the majority are, but after the match is made, Sugar Babies doesn’t get involved unless someone wants to break a contract, so I can’t be sure. For some reason, this group never does.”

  “What about the punishment clauses? Are they in these types of contracts as well?”

  “Yes, although these vary from client to client. Remarkably most women who enter into this kind of match are more than willing to trust their Daddy to care of them in any way they see fit. What one would consider punishment, another would consider loving care. I once had a client explain to me how he kept his little girl in line. He said, ‘When my little Jenna gets out of sorts and nothing seems to work, I give her a good hard spanking and put her to bed for a nap with a stout bottom pacifier. Nine times out of ten she wakes up with a whole new attitude and we can enjoy the rest of our day.’ Jenna was actually present for this conversation, and she just smiled and hid her face against his chest.”

  “Oh my God, that’s outrageous,” Jo gasped, her hand flying to her tummy. “What other kinds of punishments are in these contracts?” she asked in horrified fascination.

  Sam hid his grin and took a sip of his wine. Little Johanna was revealing more than she knew. Despite her outward reaction, he would bet money her panties were soaking wet.

  “Most contracts are pretty straightforward. It’s up to Daddy to decide how old his little girl is at any given time. If she’s acting like a two-year old, she will be treated as such. When she’s well-behaved she may be treated to more grown-up pursuits. In reality it’s the woman who has control over how old she is by her behavior. In general, all the contracts have an extensive list of equipment and supplies that may be used to care from a little girl of any age. Some Daddies insist on feeding their little girl with a bottle when she is not eating properly and there is even a group of doctors who specifically treat these little girls and enjoy huge donations for research and improving their facilities. Of course, Daddies have the funds to fly their girls anywhere in the world for treatment. About the only thing we get as far as demands from the woman involved is the public clause. Many women are quite adamant that while they have no problem being a child within the privacy of their own homes, they absolutely insist they will not leave the house dressed in any outfit that even hints at age-play. So far this has never been a deal breaker for a client, and I suspect that many of them are able to cajole their little girls to eventually comply with Daddy’s wishes.

  “Now, do you have any questions? I know this is a lot to take in, but I hope you’ll think about it before you de
cide to kick me to the curb.”

  “Sam, I don’t really know what to say. Somehow you make it all sound so reasonable yet my head is screaming at me that it’s just plain bizarre. I’ll need to give this a lot of thought and maybe do some online research. I think you should go home now and we’ll talk tomorrow,” she suggested hopefully. Standing, she stretched and yawned dramatically. “I guess today took more out of me than I thought, and the wine, whoosh, I’m pretty tired.”

  “Aren’t you forgetting something?” Sam asked calmly, his eyes intent.

  “No, I don’t think so. Oh, thank you so much for the picnic. I really enjoyed it,” she told him breathlessly.

  Sam slid to the center of the couch and held out his hand.

  “Come here, Jo. I think you’ve forgotten you have a spanking coming. Let’s not make this any worse than it has to be.”

  “You’re not going to continue that little joke are you, Sam? I understand your point, and I promise to pay more attention to what I’m eating,” she pleaded prettily, taking a step back.

  “It’s not a joke and I’m not kidding. Now come here. Make me chase you honey and I guarantee you won’t like the consequences.”

  “I already don’t like the consequences, Sam. Please, please can’t we just forget the whole thing?”

  “Absolutely, we can, and after your spanking it will be forgotten and not brought up again unless you repeat the offense,” he replied, confident she would come to him.

  “Alright, you big jerk,” she sassed, ignoring his dark expression, “but I have to pee first.”

  It was not wasted on Sam that instead of going into her bedroom to use the master bathroom, she sprinted down the hall into the guest bath. He heard the door slam and the click of the lock. Unfortunately for Jo, Sam had used that bathroom while she was cleaning up and he knew there was a window that faced into her backyard. Quietly he walked down the hall, the thick carpet muffling the sound of his footsteps. He could hear cursing and the sound of a window that hadn’t been opened in a very long while, squeak and groan. Smiling, he went back down the hall, through the living room and let himself out the front door.