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The Caretaker- Rainy day enemas

Rainy day enemas

Upstairs Tim invited Kate to have a seat on the love seat where he joined her for a second glass of wine.

"So what do you think of the property Kate?"

"What an absolutely fabulous place. The old rustic camp under the pines and the little cottage across the stream is adorable. And the history of the farmhouse is fascinating. Jenn's great grandmother who painted all those wonderful pictures of her life here is a treasure. You must enjoy your time here."

"Yeah, for the most part I love it here. It can get a little stressful when Mrs. G hands me her work wish list. She expects a lot from me. But overall, a great place to be. Kate, to change the subject, Jenn told me she was retiring early. Is she ok?"

Kate smiled, "Jenn is fine. After we left your apartment we spent some time making dinner preparations. I noticed she seemed kind of antsy and asked what was up. Tim, can you keep secrets? She told me she was wound up after we gave you your enemas. Then asked if I would give her an enema, not for the first time. We have helped each other out on a number of occasions by administering enemas to one another. So I had her stripped down and on all fours for a soapy enema. We had dinner and she retired with her book and Mr. V. Mr. V being her pet name for her vibrator."

"So she left you on your own tonight with nothing to do?"

"Well, not quite. I had some ideas of how to occupy myself. But they included you."

"And the wine was part of the plan?"

"Of course, but only the beginning."

"The beginning?"

Kate placed her hand on Tim's thigh. Yes, the beginning. I want to play. With you. So are you up to it? Want to play Cowboy?"

"I guess, but I'm not sure what you want to play?"

"Oh you are so cute. I want to give you another enema. A special enema. But first, I want to have you naked and over my knee so I can give you a spanking. That is, of course, if you agree. If not, feel free to say no." Kate took his hand, "I wouldn't want you to do something you would rather not. But you would not want to disappoint a guest would you Tim?" A mischievous smile crossed her face.

"I suppose that would not be polite now would it?"

"No it would not. So it seems you're agreeable so stand up please. Now get undressed, everything off and present yourself before me."

Tim did as asked. He pulled off his Tshirt then kicked off his shoes and then while Kate observed removed his jeans to stand before naked as she had requested.

"Tim, Jenn told me you have a nice wooden spatula perfect for spanking a boy's naughty bare bottom. Get that please."

Tim complied fetching the spatula and handing it over to the attractive woman. As he stood before her looking down he could see her cleavage. Did she undo a button while I retrieved the spatula? It seemed so.

"Very good. Now I believe at this point Jenn requires you to ask for your punishment. So tell me, what do you want me to do Tim?"

Tim felt a flush of embarrassment wash over him. That never seems to go away when he found himself in this position. Embarrassed from standing naked before a beautiful woman who was fully dressed. With great cleavage. Embarrassed from knowing what happens next. Embarrassed for what he must now say.

With a deep breath Tim responded, "Kate, I have been naughty. Will you please spank me like I deserve?" He looked Kate in the eye as he answered and felt his cock began to harden. She gave him that alluring mischievous smile again.

"A naughty, nasty boy should always get what he deserves and you will." Kate stood to stand next to Tim. She leaned in close as her hand petted his bare ass and for a moment only breathed into his ear. Then in a whisper, "Tim look at yourself, Naked in front of me. Like a little boy standing before his mommy knowing Mommy is going to spank his bare little bottom until he cries. And because he knows he has been naughty? He maybe starts crying even before his mommy starts to spank him. Are you going to cry before I begin? Or be a big boy? But even big boys cry when their mommy gives them a good spanking. Now, bend over so I can begin your spanking like a mommy would do."

Tim awkwardly bent over as Kate stepped near wrapping her left arm around his waist pulling him tightly against her. Facing backward she took some time to take in the moment. This young man so obedient in allowing her to put him in such a position. The bare white of his naked bottom contrasting with deep tan above his waist.

"Spread your legs a bit. Just like that. It's time for your spanking." Her right hand landed immediately across both cheeks with a loud crack. After a pause she followed that with two dozen hard spanks given in quick succession. "Stand up please."

Again Tim complied as Kate returned to the love seat. His erection had subsided somewhat from the spanking, but as he stood exposed to Kate it began again.

"How naughty! I thought I spanked that away and here it is again. Now I want you over my knee."

Kate helped Tim to lower himself over her lap. In his mind Tim was in ecstasy. This mixture of feelings that he experienced from excitement, and aroused to a bit of fear from the pain he might experience from the spanking. And Kate? She was getting off on the excitement of having a handsome young man complying with the naughtiness of what she was doing. Having him stand naked before with a raging erection while waiting for her to take him over her knee to spank his little ass a bright red. She could feel herself becoming wet as Tim lay fully across her lap his erection pressing against her leg. She reached down to move it between her bare thighs and squeezed tightly.

The spanking began again. Kate wasted no time in counting or scolding. just a simple whisper in his ear, "Now you are going to get it good." She spanked hard from one side to the other delighting as the white skin began turning pink. After a couple of minutes Kate paused.

"Well, ,Kate thought, "Jenn said he could take a good spanking and he certainly can, barely a flinch. Time for an implement," as she picked up the wooden spatula. "OK hon, it's time to finish your spanking." She draped her right leg over his assuring he would remain in place. "You are not going to like this. But it has to be done."

The spatula connected with a sharp crack and the result was to Kate spectacular. Tim flinched as the spatula landed and cried out. "I told you you would not like this, But remember you asked me to spank you. I am only giving you what you asked for." Kate lowered her voice to a whisper, "Almost done. Can I finish? I am going to make it hurt. Are you sure?"

Tim turned to look over his shoulder, "Ok, but are we almost done?"

"Yes sweetie, almost done." Kate rubbed the wooden spatula over her hand giving herself a sharp blow. What a sting. And what a perfect spanking paddle. I wonder if that's why he bought it? And maybe when she has finished he will regret the purchase she thought.

Thoughts aside she began the spanking. The spatula soon had Tim squirming and moaning from the repeated spanks landing with such force. He found himself tearing up and Kate seemed to spank even harder forcing him from an occasional moan to out right sobbing and crying, "It hurts. Bad, Please Kate please." But Kate continued until he had gone limp over her knee, just crying as she spanked him.

"There all over. Sit up for me sweetie, stop crying, it's over." Kate helped him stand and then patted her lap. "Sit here." Tim did as told sitting himself over her lap. Kaye pulled him close. "There now, all over. Give me a hug." Tim had no problem with that, finding as he did so he held on to Kate like a frightened child.

Kate could feel the need from the young man so she willingly returned his embrace. "There now it's ok." as Tim began to cry quietly on her shoulder. "Poor boy, don't cry. It's ok. Here now just relax a minute." Kate began to caress his naked bottom. After a few minutes her hand wandered to touch that very private place. Tim gave a sigh of pleasure from the touch/

"It's time for your enema Hon. A special enema like I promised. So I want you to get a towel and go to the bedroom. I will get your enema ready and be in shortly.

Tim grabbed a clean towel and went to the bedroom. A special enema? What could that be? A different nozzle? I will soon find he thought. He set up the stand to hold the enema bag and waited for Kate.

She soon entered carrying the filled enema bag and the jar of Vaseline. "Everything is ready. Tim please lie down on your stomach so I can get you ready." Tim lay down spreading his legs for what was next. He watched as Kate lubricated the nozzle and adding more to her finger spread his cheeks a gently applied the lube to his bottom. "It's time for your enema." Just as Jenn had related at the mention of the word Tim became aroused. "Now I told you I would give you a special enema so please stand for a moment."

Tim stood, curious as to what was next. He watched as Kate propped pillows up and lay down spreading the towel by her side. Patting the towel, "Lay down right here for me." He lay down as told.

"You need to get closer sweetie, don't be afraid. Kate urged. "Slide down just a little. Now relax." Picking up the nozzle she leaned over him deftly separated his cheeks with one hand slipping the nozzle in place. "Now to make it special." Tim watched as Kate unbuttoned her blouse and removed it completely leaving her wearing only a low cut black bra. "And this too." as she undid the bra setting off to the side. Her breasts were a young man's dream come true. Tim could not believe what was happening. Kate released the clamp allowing the enema to begin and then leaned over to Tim, her breasts brought to his face. "Do you like them? I know you do, I have caught you looking. Kiss them Tim. Be a good boy. Nurse me sweetie, suck on my titty. Make me feel good. Yes, just like that." She reached down grasping his semi hardness slowing stroking. Both lay quietly blanketed by the feelings that were going through their bodies.

"Kate, that feels so good." And then as he heard the gurgle from the enema bag emptying, "Oh, I have to go. Can I please?"

"Of course sweetie go ahead." Tim rushed off to the bathroom Kate got up to clean the equipment before returning to the bedroom. She slipped off her shorts and panties and lay down to await the return of the young man. Her body seemed to be high alert. She was wet and horny as hell and hoping the man she was waiting for would take care of that.

Fifteen or twenty minutes passed. Kate heard the toilet flush several times and the shower begin. A few minutes later Tim returned. He stopped dead as he entered the doorway. Kate, naked on his bed. It was not what he thought would happen. At best he thought he might cuddle with Kate for awhile before she excused herself to leave, Maybe, if he were lucky she might finish stroking him off. But this?

"Don't be bashful Tim." Kate beckoned, "I have been waiting for you. Get your bottom over here or I will have to put you over my knee again. You don't want that do you Cowboy?"

"No Maam, I don't." Tim smiled as he he slipped into bed and into her arms.

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