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E055: The Thirtieth Pearl  

Clairew1959 64F
95 posts
1/25/2019 5:46 am
E055: The Thirtieth Pearl


At the spa, after having her manicure and pedicure, Emma is still a bit aroused from Donald’s massage and thinking about seeing Sasha again and wonder what will happen today. She is so disappointed when there is a different woman there to trim and wax her today.
She adjusts to this disappointment realizing it is just some of the punishment from last week and Donald must have arranged the change. It is probably for the best.
This woman is so businesslike and to the point. There are no warm breaths on her; her hair is trimmed quickly and closely. Her legs and underarms are waxed and made hairless, and then the woman has her roll over, and she waxes and rips the hairs from her crack and hole.
Sasha had clipped them. This does rather hurt.
The lotion is rubbed on in a mandatory fashion, and before Emma knows it, she is told she is done. It took less than half the time of Sasha sweet administrations to her. But she is in fact waxed and clipped thoroughly, so there can be no argument.
Emma drives home a little sad but knows she brought this change on all herself. She wonders if she will ever even see Sasha again?
Home, she undresses and goes to the living room to stand to wait as Donald directed her earlier in a text message. She wonders what will be ahead now. Donald does seem to be leading her down very different paths for the last several pearls. Where else can they possibly go now?
Donald comes into the living room also undressed and smiling. He runs his hands up and down her legs and thighs checking her waxing. With her arms raised to the back of her neck, he can also check how smooth under her arms are.
Then he takes his time inspecting her mons and slit to see how well she is clipped today. It is almost like he is making up for her for not to having Sasha touch her earlier.
He turns her around and tells her to bend over. He had seen how her crack was rather pink when he came up to her. He spreads her cheeks and runs his fingers up and down her crack and around her asshole stating that she had a thorough waxing and clipping today it seems.
Emma wiggles at his touch her all over as shivers run through her.
“Emma, we are going to start something tonight, just for a while probably, to help you open yourself, in an acceptable way for me, to other men,” Donald tells her.
Emma gasps at what Donald might be suggesting, but then she sees her laptop open on the coffee table and wonders what he has in mind.
“We will talk about it over dinner which is ready, and then start,” Donald explains.
Emma follows him to the kitchen, bends to have a plug put in, and then when she stands she asks Donald if he would like to wear a plug also.
Donald replies, “Emma, that might be a good idea for us both to have our asses filled and enjoying the sensation when we commence after dinner.”
He gets another plug for himself, and Emma inserts it. They both feel the comfortable uncomfortableness up in them. It is such a mixed feeling, but overall enticing to them.
Over dinner, Donald explains what is ahead. “Emma, I have set up a secure user name and password for you so not to be traced back to who you really are and found a couple of great meetup sites for you to go to. After dinner, I am going to take a couple of discreet photos of you to add to the sites, and then I want you to start finding some men to chat with.”
Talking to strange men over the internet? And she takes it will be of a sexual nature considering what Donald is proposing. Can she do this? Well, she is sure he is going to be by her side as she does so that she can try.
After dinner they start, Donald does not show her face in any shot but takes a picture with her just holding up the afghan low on her breast from her waist down. Then a back shot where the afghan is just barely covering her ass cheeks. One of her so smooth legs and pedicured feet, and finally one of her standing covered in the afghan her head turned fully from the camera.
They all are tasteful and wonderful pictures. And no one will know it is her.
Donald then adds the pictures to the sites, all proper and acceptable for any policies they might have. Emma looks at the profile he wrote for her, on each a little different, but all saying she is there to satisfy men’s fantasies and desires. She blushes profoundly realizing what is being projected about her.
The profiles are open and viewable now. Donald tells her just to lean back and wait for messages to come in. The three sites are all open in different tabs on the browser.
Donald pulls her to him and begins to kiss and caress her. “Emma, you are going to do this wonderfully, be open and express erotic replies without suggesting too much. I will help you with this. I think this is going to be a fun evening’s entertainment.”
Emma has mixed feeling about this, but responds to his kisses and fondling.
It is not even fifteen minutes later when Emma's computer starts to ping, bing, and whistle at her, demanding attention. Multiple men on all the sites want to hook up and friend her. Emma and Donald take their time looking at each profile. If someone just gives a ‘hi’ message, they are rejected. The possible candidates must show that they have read her profile and are interested in her. And be somewhat creative and having proper grammar and spelling, which all adds to the candidate’s acceptance.
On the three sites, they choose six different men of appropriate age, background, and apparent ability to respond to. Emma now has six cyberspace friends.
She briefly replies to each after accepting their friend request, and four of them start chatting immediately. How is she going to handle chatting with four men at once? Donald laughs at her dilemma and tells her to pick the one she wants to start chatting with now, tell the others she is busy at the moment and give them distinct times for them to chat back with her this evening.
She does as Donald tells her and finds all the men agreeable to her conditions.
The first man is in his late forties, a professional. His picture is nice, but she wonders how old it is. They chat just getting to know each other, Donald telling her details to say about herself. Close to who she really is, but not enough to give herself away.
She tells the man (and the others later) that discretion is essential for her being on here and chatting. It is just some fun to have on a Friday evening home alone. The man laps it up.
Before long Emma, at Donald suggestion, asks what the man’s fantasies and desires are?
That is all it takes, and the man starts in about wanting to be with her, undress her, make love to her. Well, that is not too bad for a start. She sets up a scenario for them meeting and is soon in the thick of it telling him what she is doing to him as he undresses her and starts to cyber pleasure her.
And it does not take long; the man is telling her he is cumming hard. Even texting back and forth he lets her know by holding down a key to show he is spurting hard, and his comments after confirm it.
After getting his breath back, he thanks her over and over and tells her that he hopes they can do this again very soon.
Emma replies she enjoyed herself too, and who knows what the future will hold, but for him to keep in touch.
One down, three to go.
The next one is pinging her, after hardly enough time for Donald to get a bottle of wine and pour them some. Right to the second of when she told him she would be available.
Emma greets him warmly. She is a little concerned about the site he is on. It is more open and revealing than the first one. Men are flashing their pricks in profile pictures, and individuals check off what are their kinks and desires. Is she getting in over her head?
This guy profile says he likes to be spanked like a naughty little boy. Hmm.
Donald nods to her and tells her that she knows the other side of a spanking, she should be able to describe it to him.
He is a little younger than Emma, in his very late thirties, so perhaps she could try.
Again, it takes no time for him to get describing what he would like to happen. He knows it is in the virtual world, but to imagine being over Emma’s lap as she spanks, and perhaps jerks him some, would be a fantastic way to end his week.
Emma laughs with Donald as she asks him what he has done wrong to be such a bad boy for her. And he recites a list of things he did wrong during the week at his work. Him being late for meetings, not replying to emails, wasting time when he should have been working. Oh, he was so ready to be punished and spanked.
Emma does ask him what he wants her to spank him with and they agree on her hand, and then wooden hairbrush.
She tells him to lower his pants, and his underwear, this is going to be a bare bottom spanking. He excitedly responds that oh, to start there already. Emma replies that they are not going to waste time, considering what a bad boy he has been.
He whimpers as she tells him to lay across her lap. She says him that she is sitting in a straight back chair, so his hands and feet are on the floor over her lap.
And she begins. She tells him spank by spank as she rains down on both cheeks over and over. He is whimpering telling her he loves it all. She spanks him, telling him he must say to her why he is getting this spanking.
He goes into great detail of his each of his misbehaving at work. He is lusting for being punished for the crimes, well misdemeanors, he has committed. He even types that he is sobbing from her hard spanking.
Then she tells him he must reach and hand her the hairbrush which is sitting on the table in front of him. He gasps as he tells her ‘yes ma’am and swears that he is handing her the brush.
She states to him how spank by spank she is now using the hairbrush on him. Donald sits back in wonder as he watches her fingers fly over the keyboard responding and playing this scene out to a conclusion.
Donald does motion to the clock to remind her that the next visitor is due soon. So, she tells her 'little boy' that she can feel him hardening between her legs, so puts one hand under him and holds and jerks his cock as she explains to him how the hairbrush is spanking him again and again.
And moments later he cries out to her, telling her tears are running down his face that he is so sorry he came on her legs. He could not help himself.
Emma orders him to stand and go to the corner and press his nose against the wall. She informs him that she wants him to stand in the corner this way for the next half hour. She is leaving now, but he better do as she tells him, and perhaps they will talk again if he has been naughty.
He promises her he will, and that he had actually taken his pants and underwear down when she told him to and will leave them down for his corner time. Emma states she is giving him a kiss on his forehead before sending him to the corner.
Later that night, about an hour later, she does receive another message from him thanking her for giving him the spanking he needed, and that he had stayed in the corner thinking about what he had done wrong for over a half hour. Emma does not reply then.
The next caller is a man in his late fifties, from the same site as the last. His fetish is wearing woman’s panties and silk stockings. He loves to dress up in them under his clothing that no one knows. He is with a woman, but she has absolutely no idea about this side of him.
Emma questions him some that if this is a part of him which gives him pleasure, why can’t he share with her? These men she is meeting here tonight are truly expanding her sexual horizons.
So, she goes through the paces with him, looking at his panties and stocking pictures on his profile in which he does have rather nice legs and ass. One photo of his panties and cock sticking out from his opened jeans is rather enthralling to view.
She chats with him about him coming to see her and revealing he is wearing panties. Emma tells him she takes his pants off him and puts a garter belt, pulling it under her panties, and then rolling silk thigh high stocking up on him and buckling them to the garter belt.
She sees she say how hard he is under his panties now and takes him to the makeup table to put some on him. He goes over the wall when she says this. No one has ever suggested putting makeup on him, and he would so like it.
“Well, of course, makeup, and then a bra for you if you want to be pretty in your lingerie for me,” Emma types to him.
Then, step by step Emma outlines putting mascara, eyebrow powder, eye shadow, liner, blush and finally lipstick on him. By the time she is finished, he tells her he has the biggest hard-on ever.
“Well, then, we need to take care of that sweetie,” Emma writes as she tells him she is leaning and kissing him for their lipstick to mesh together.
She barely has him on the bed, moving his panties aside to get at his cock to suck it when he spurts hard up in her he tells her.
She and Donald start to laugh hard at this. What incredible skills Emma is displaying. How they come from her inner soul to do this?
Emma kindly leaves him in the same way she finished the conversation with the other two. She leans back on to the couch and Donald runs his fingers up and down her slit. She is soaking from these chats. He moves his fingers up in her to bring her satisfaction as his thumb polishes her clit. She moans with bliss.
And the laptop pings once more. Her fourth caller.
Now during this time, others have been trying to chat with her too, but for now, she ignores them. Perhaps, if they play this game again, but not tonight. And Emma realizes this is a rather pleasant game for her and Donald to play together. When she gets a little lost in what to say he instructs her what to type, but for the most part, Donald seems, seeing how hard he is now, to be enjoying watching her interact with these strangers.
The last caller changes things a little. His picture is only of his cock peeking out from his opened pants. He is near her age and says he lives in a nearby city. That he has a college degree and holds a prominent position in the community, so yes, discretion is so important to him.
He and Emma start chatting. He seems to want to talk more than heading right to the sexual interaction, which by now Emma is grateful for. It rather bland in many ways, just about the weather, Donald places her location about fifty miles away so while near, is not that near. Only Emma knows he is saying he is closer to her.
He tells her a bit about himself, but she is careful to be very vague about herself. He says he is looking for an ideal woman to spend his life with. He had thought he had found her, but it seems she is now involved with someone else.
Emma asked him what he was looking for, and his description rings too close to home. And when he says he works at a bank in a high position, Emma loses it.
It is her bank president she is chatting with late on a Friday night, him trying to find someone just like herself now. Tears fill her eyes, and Emma turns to Donald and asks what she should do? “It is the bank president, the one who came up to us in the restaurant. I can’t chat with him.”
Donald sees her dilemma, and knows he doesn’t want Emma chatting with that man anymore, but how to end the conversation nicely?
He tells Emma to pause between responding and pulls her to him and kisses and holds her tight. After about five minutes, he suggests that she tells him she is sorry, that she does not think she is who he is looking for, as her life right now is complicated, but to send her best wishes for his search.
Emma realizes he is crushed by his immediate response saying he hopes that isn’t true and really wants to get to know her more.
What is she to do?
Donald tells her to say she must go now, it is late, and there are things she still must do. She does and wishes him good night. He replies that he hopes they can chat again soon.
She does not reply. Instead, she turns off her laptop and falls against Donald’s shoulder sobbing. How could she do this to someone who is a very nice man? This game is not as fun anymore.
Donald comforts her and tells her it is okay. They just made a bad pick for the last one.
“But Donald, how can I face him at the bank, knowing about this conversation, I am so embarrassed,” Emma moans.
“Honey, he doesn’t know who you were, and we will take down your profile on that site, so he can’t reach out to you anymore. You did do so well tonight, and up to him I think you were enjoying yourself,” Donald tells her.
“Do it now, Donald, please, I don’t want him to try contacting me again,” Emma pleads.
“I will in the morning, Emma. Now let’s get you to bed, and you can act out some of that first scene you were in with me,” Donald replies.
“Oh, you don’t want to wear a pair of my panties and stockings to enjoy replaying that one?” Emma teases him.
“Not tonight, but who knows, maybe you will take me to that deviant dimension someday,” Donald laughs in reply as they head to bed, her thirtieth pearl and some role-playing before falling asleep.

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