E053: Donald’s request and Emma’s Twenty-eighth pearl  

Clairew1959 62F  
96 posts
1/23/2019 7:33 am
E053: Donald’s request and Emma’s Twenty-eighth pearl

When Donald wakes and sends Emma off for her morning pampering, he wonders if what he wants to ask Emma to do to him today will be more than she can handle. He must word it just right, and hopefully, she will agree. Now he will not press her to do anything more than she can endure. If she feels unable to, they will just move on to another pearl.
After their bath, as they sit at the kitchen table eating their breakfast, Donald broaches it a little. Before sitting to eat, Donald again puts a plug up in Emma’s ass which she seems to enjoy now so. This may help in what he wants to suggest to her.
“Emma, you know how I told you when I was first at the academy I was bullied by that one boy a lot?” he asks her.
“Yes, Donald I remember you mentioning it. How did he bully you?” Emma replies.
“Do you know what it means to bugger someone? That is what he did to me for the first half of my beginning year there,” Donald says in a soft voice.
“ not really sure what you mean,” Emma replies.
Oh hell, he is going to have to spell it out for her, which he knew he would have to, and what he wants her to do to him.
“Emma, he fucked me up the ass, almost every other day for months. I didn’t like it, but the remembrance of it does seem to arouse me from time to time. You know how you used the strap-on with Connie, do you think you would be able to ass fuck me with it? I to feel that again. You will be in complete control as we do this, and I want to submit to you in this way, as I did ago to him,” Donald cannot believe all that spills out from his lips.
Emma gazes at him and then is quiet thinking to herself. Finally, she replies, “Donald, I not sure how good I will be doing that for you, but if it is something you , I will try to do it for you.”
Feeling the plug up in her at the moment, helps this decision along, knowing how wonderful it can feel, and remembering when he had fucked her that way a week ago. Yes, she would try to return the pleasure.
Donald leans and kisses her deeply. “Thank you, Emma, we will try after dinner tonight. I will clean myself this afternoon in preparation. I can’t thank you enough for agreeing to this,” Donald gushes at her, “Perhaps now you could put a plug up in me to help me prepare.”
Donald goes to the special kitchen drawer and brings another large plug out. He hands it to Emma and leans over the kitchen table as she does for him. Emma fully coats the plug with lube, and so slowly and gently, stopping as she starts to enter him, so he can relax and accept this assault, she presses the plug up in him fully.
Donald moans with delight.
“I’ll wear it all day until this afternoon when I clean myself for you in preparation,” Donald solemnly tells her.
She smiles at him as he now bends her over the table so that he can remove hers. They take a moment to kiss before they head to the bedroom to dress Emma for her day.
She will spend it at her house cleaning and sorting more things. There are now, from reading her mother’s diary entries, things she wants to check out. Emma tells Donald she will return by five o’clock, will he be ready then or would he like to have dinner first?
Donald feeling a plug up in him, it has been a good while since he wore one, and in giddy anticipation of what is to come this evening wasn’t sure. “Perhaps a quick light snack before the games begin?” he suggests.
And so, the evening, a very different evening, is planned for them.
Emma spends the day at her house, first going to the attic to find the boxed away dresses from before her mother married, and she is rewarded. They all are rather mini-dresses, cut low, and rather revealing. Not like anything her mother ever wore after her marriage. They are all in fine condition still forty plus later. Emma boxes them back up to take to Donald’s to show him.
They do look like they will fit her nicely.
Then she searches more, in the extra bedroom, for signs of Susan’s and Charlotte’s dates. She remembers that when she was little, her mother would put her down for an afternoon nap when Susan came to visit on Wednesdays. And Emma vaguely remembers sounds coming from this room.
Her father never went in it; it was just a furnished room never used in his mind. And Emma understands her mother and Charlotte not to share their lustful on Charlotte’s marriage bed.
Later, she would have been in school when this afternoon took place. Wednesday her mother always did seem to have a smile on her face.
Emma remembers too that during her mother’s illness Susan would be there by her side quite often, and she had been overcome when Charlotte died. All these things whirl in Emma’s mind as she finds a locked suitcase under the bed.
She locates the key in one of the dresser drawers, and when she opens it, she sees a wide array of sex toys they must have used in their . Emma locks the suitcase and takes it to the trash. No one ever needs to know about this.
Emma considers visiting Susan in the adult living facility she is at now, but wonders what the point would be? Would Susan enjoy being able to talk about her real relationship with Emma’s mother or would it upset her too much? Time will only tell.
And what is ahead for her tonight with Donald? Emma hopes she can do this as he desires. She did enjoy the feel of him up in her ass and wanted to experience it again soon, but this is something totally different to her. Does he still have desires for a man to take him, or would this just be her up in him to pleasure him in this new way?
She hurries and puts the box of her mother’s clothes in the car and heads back to Donald’s. It is approaching five o’clock already.
He meets her in the garage when she arrives. My, he must be anticipating this so.
She tells him what is in the box, and he carries it in the house for her. He says he can’t wait to see her in some of the dresses. Even if Donald did not buy them for her, her small gift of something to amuse him does so delight him.
She sees there is an outfit for her lying on the bed. A light green blouse silk, trousers in grey, and a pair of boxer shorts. Oh my, he does want me to be a man for him is all Emma can think.
Donald seeing her look quickly explains, “I just thought you would be more relax if feeling the dildo up in you as we eat you are in a more mannish manner.”
Emma giggles and tells him if that is what he wants.
Donald slowly undresses her and first helps her press the dildo up in her and belts it around her waist. Next, the boxers cover it. He adjusts it to lay against her for now. Then the blouse, no bra, which does feel so nice against her boobs and nipples, then finally he helps her into the trousers.
He does her hair, so it is pulled back into a bun at the nape of her neck. He leans and kisses her there before adding just the slightest amount of makeup. He is dressed in khakis and a polo shirt. He tells her for this to work out how he desires she must take down his pants when they do the deed.
They go and eat a quick dinner and Emma realizes that Donald is being rather submissive to her, and the rush she felt when she was in control with Connie begins to run through her. She admonishes Donald for not finishing his vegetables and tells him that he will have to for that after dinner.
The flush of desire that comes to Donald’s face, Emma knows she is playing the role as he so wants her too.
“Come along now Donald, I think it is time for our nightly pleasure,” she says in a low voice.
Donald just meekly nods and walks with Emma from the kitchen. Tonight, she is the one with a hand on his ass cheek. She still is rather nervous unsure she will be able to do this, but she is now getting into the role rather well.
Donald leads Emma to another bedroom, which has a higher, smaller, four post bed in it. It is not his bedroom, but somewhere suitable for the game they are going to play. Emma tells Donald to get some condoms and the lubricant. He knows what he must do.
Donald scurries around getting the things and bringing them to Emma. She tells him to kneel in front of her and undo her pants. Donald quickly complies with what she commands. This is so like what had happened to him for months in his youth. His hard-on is at its utmost.
Emma says, “Now suck on my cock to get it nice and hard for you.”
There are tears of joy in Donald’s eyes as he bends to do her bidding. The cock is in his mouth about halfway up. Emma encourages him to take more in. He does until be begins to choke some.
Emma pulls out of his mouth and tells him to put a condom on her. He complies. Then she has him lube her cock thickly so to make sure she can slide up in him.
Only then, her trousers and boxers down around her knees, does she have Donald stand and she undoes his pants. They fall to his ankles.
“Now put a rubber on you too as I don’t want you cumming all over the bed,” she directs him. He does as she asks and stands before him cock covered waiting.
“Bend over the end of the bed here and hold on to the posts for support, I think that is how we will start,” Emma says with so much authority in her voice.
Never from meeting her could Donald image she could be this forceful, displaying such power over him. At this moment it is exactly what he is lusting for, so he bends and spreads his legs for her.
She comes and stands behind him. He feels her fingers wet with lube run up into his asshole, coating it well also. He moans with delight.
He then feels her press the glans of her pseudo cock into his anus, stopping at the sphincter to allow him to accept her entering him this way. He moans with the combination of pain and pleasure this is giving him.
Never back then at the academy did he ever think of this act as anything but punishment and control over him, but that had somewhat added to who he became. And now, Donald wants to remember the inner pleasure it did give him when that older boy was banging his ass.
Emma presses in more, and more, beginning to thrust in and out of him. He cries out in ecstasy. This is what he longs to feel again.
Emma leans forward putting her hands on each side of him to brace herself better as she thrusts away. Donald feels her soft breasts pressing against his back which brings the reality that it is a woman doing this to him now, and that takes him over the edge. He comes loud and hard. He fills the condom with his sperm.
“Oh, Emma, thank you, thank you so much,” Donald gushes at her.
But Emma does not let up. She knows this fun is just beginning for Donald, and he wants so much more. She rams into him faster and harder, and his anus begins to throb against the dildo.
‘What is Emma doing to him? This is the most decadent but enjoyable thing they have done together, and she seems to know what he craves even if he doesn’t fully understand,’ Donald thinks as he moans and whines.
Emma slows and pulls out of him. He is awash in sweat and desire. She tells him to get up on the bed on his back and raise his legs. Donald a little unsure of what is ahead but does as she tells him. Climbing on the bed this way his pants and shorts fall off him.
Emma steps out of her trousers too, goes and gets a damp towel and removes the condoms from them both and wipes them clean.
“Donald, did he ever suck your cock, or only had you suck him?” Emma questions him.
“Occasionally he would like to suck me until I was ready to cum. He told me then that I was not allowed to and sent me to bed. I often had a<b> wet dream </font></b>those nights and woke with soaked sheets. He would punish me further that next night for not following directions,” Donald explains.
“Well let me put another condom on us both, and I will suck you to get you hard again through the rubber. Then we will lube up again, and I will take you in this position, so you have to look at me the whole time,” Emma tells him as she lifts his polo shirt off him and unbuttons her blouse so that he can stare at her bosoms.
She rolls a condom up each of them then bends and begins to suck him. As he starts to harden, she gets a wicked thought and turns herself so her ‘cock’ is over his lips and tells him to get busy.
For the next fifteen minutes, they suck each other’s pricks, Donald getting harder and harder, the sensation of having a cock in his mouth, while someone is licking and sucking on him, never before did he experience this. And sucking and being sucked through condoms the rubber adds to this deeply different playing.
When Emma feels that he is hard enough again, she turns to situate herself between his thighs. She covers her condom, wet from Donald’s tongue, with lubricant and then fingers some up into him in preparation.
His legs are now lifting high on her shoulders. She stares in his eyes and stays locked on them as she begins the ramming into him as far as she can go. He screams out in gratification. This is even better, watching Emma as she butt fucks him. His whole body is electrified, shock wave after shock wave running through him as he accepts this attack on his most private hole.
He comes so hard again, Emma smiles at him as she glances to see him fill his condom full once more. It is only then when he is panting and trying to get his breath back does she lower herself to him and kisses him deeply.
She is still up in him, but just resting as he enjoys her soft lips on him and her sweet breasts pressing against him. They stay this way for several minutes. It is only when Donald’s breathing is again normal that Emma slowly pulls out of him.
Emma stands, removes the condoms and wipes themselves. She tells Donald to rest of a while; she is going to go clean up. She pulls a cover over him to warm him and kisses his forehead.
“Sleep my dear, when you are rested, come back to me in my room for the night. I will be waiting for you, sir,” Emma tells him.
Things are again back on the even plane for them. But it is somewhat humorous that it is Emma closing the door, leaving Donald in darkness to sleep this time.
Needless to say, the next morning, Emma gets her twenty-eighth pearl on her necklace.

RobK2006 54M
5944 posts
1/23/2019 9:20 am

That was really intense. I got a full erection reading it.

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